The highest of commandments dictates to copulate
I made a bright and a light version, however they are both quite a bit different, the face and outfit and position is altered in each, besides the shading/coloring, which one of these do you like overall better?
Was not entirely happy with how this one was turning out, Im not kidding when I say I repainted the head around 30 times, whenever I try to go for more realism in a face and stray further away from the cartoon faces, I keep tweaking it and changing it since the slightest little details can make everything seem off.
Here are some of the steps before the final version, I thought these where specifically interesting given the outfit changes, I originally was going to also do a full nude version, or a dickgirl one, but Id rather just move on to the next post at this point, since Im really tired of working on this one.
Did shad get covid19??????!!!!!
I sure hope not. He is a complete fucking Darwinist who would rather die than seek medical attention. Atleast thats what he said during the Sleepycabin podcasts. Would be sad to see him go.
I’m secretly in love with DFE which is why I can’t resist replying to her and posing as her.
I just realized that when I copied her Gravatar just now I made errors in spelling (“breads”), capitalization (“im” and “i”) punctuation and sentence structure that DFE would never make. That’s because instead of paying attention in school I was busy watch pedo porn and giving blowjobs to the Mexican gardeners who worked at my skool.
Is he okay
Bruh
Hey shad could you do some pinups of this girl? insta: imogendoughty
Super fucking creepy dude
Different guy but why
Can you give us some Harley Quinn (and maybe poison ivy) stuff in honor of the new show???
When the comment section is a full of people demanding more uploads or insulting the people who demand more uploads, but you just want more goth girl from the burger comic.
Dude you alive or have you been claimed by the virus
I would just want to know is he okay…he normally at least gives a quick sketch to say everything is okay.
Hope his health is holding up or nothing seriously happened.
Come on man it’s been around 2 weeks by now
Im GoiNG tO POsT atLeAsT TwicE a WeEk – shad
There are only two certainties in this world: everyone dies eventually, and shad cannot stick to a regular upload schedule.
Anybody else realize how easy it would be to respond to your own comment to make it seem like an argument
Shut the fuck up and go suck a dick you shithead
Huh neat
Cool
You could do My hero academia
shadman, where is the shadporn
Just because I laughed hard, you should see that : https://rule34.xxx/index.php?page=post&s=view&id=3795703
Are you dead ? Where is new the pictures
Show!
Hey take your time! Don’t worry about the people that are just angry in the comments. Art takes its time.
shad for the love of fuck just make a comic or something we need more porn
You are seriously starting to take too long for a single post
Friends, I ask of you to look upon the ancient archives and reminisce in the old memories of Shädmans fap material. I promise, wholeheartedly, it is worth it. Maybe you’ve seen it once before, but don’t hesitate to see it once again. Rejoice in his glory for the horn he can instill, and dispell. Thank you fellow patrons of horn, go bust a nut to one of this man’s fine works of art, a true renaissance masterpiece.
That is what i’ve been doing my humble friend the ancient nun from 2 years ago is still good enough for me
Wow these comments are fuckin nuts. Take as long as you need. I can guarantee you these guys will be complaining no matter what.
Next loba
I am a sissy femboy ready to do anything for dick. Kik is thedude420420420
Idk if you’ll ever see this Shad, but keep up the good work man. You’re pretty inactive right now but we all lose motivation at some point. Besides, though you’re my favorite artist there’s always more shit to jack it to while I wait for more uploads. Take care.
i agree wholeheartedly. Moreover there is never enough support of shad in these comments. HE really does good work!
Agreed
Agreed, but could we get any updates? its been ten days. I like the improvement ur art but set up a schedule or announce some sort of hiatus
The dude “loses motivation” like twice a month. It’s like he has a menstrual cycle or something.
Artblock is a bitch for all artist…
Shad has a ton of suggestions, how the fuck is he having “art block”. Just look at the comments.
New one please
You need to draw the nintendo princesses gang bang but theyre all futas
yes nintendo, no futas
+1
-1
So… did shad die?
You should totally do the mario princesses gangbang futa
You’re doing great Shad! Still adore your style!
Can you start picking up the pace with new drawings? I’m assuming you’re isolated with nothing to do all day. Fucking lazy
sorry he can’t sate your disgusting horny needs you clown
Shoot yourself
Shut the fuck up. when ever shad takes this long to post something it is really fucking hot or he’s testing a new art style for better content in the future
No he’s just being a perfectionist
100% agree. He needs to step the fuck up or be honest about the times he’s gonna put stuff out.
2 weeks for 1 picture? Wow. Shad, I get you stress yourself on the detail or that you want to make sure the proportions are perfect but right now, with you, Quantity is BETTER than Quality.. y’know? These pinups are great but it’s nothing to fap to I believe that’s the core problem that everyone has with this.
Jokes on you i actually fap to the details
Damn this comment section is craazy but shad idk if you gonna see this but if you ever do please at least say that you’ll stop posting for a while instead of just ghosting.
Shad in the past: I got this in a week *makes one or two in a it in a week. Sometimes it’s a comic*
Shad now: I got this this a week *makes a picture in 2 weeks* sorry guys saw its been a week.
Bruh that was two weeks. If it is going to take you more than a week just say so. Don’t keep saying it’ll be a week when it has been taking you two to two and half weeks to make something. You’re art is great just be true to yourself.
Love it
You’ve really lost what made you special. Pathetic.
He’s still got it. I can’t say too much but I think you guys should cut him some kind of slack, because I’m pretty sure being an artist isn’t just shitting out poorly drawn pictures to make a bunch of horny cunts happy. I appreciate that he acknowledges he’s behind on posting, but he probably has a life outside of this website. If you’re so fucking desperate for new content than go somewhere else. Or just look back into the archive. It’s a simple fix of basking in what the site used to be, and periodically checking what’s new. Chill the fuck out. I doubt your an artist, and even if you calling Shad pathetic is a straight fucking insult. Keep this shit up Shad. We love your work.
Shad you take 10yrs to make something these days. U used to do a whole comic in a month
When we getting the next one?
Lobo from apex legends?
We need that Lobo from apex legends
My wife need a coomic for her
lol shad got covid-19
If you like femboys or traps hit me up on KIK JGsub
very fun minecraft roleplay server for kids version 1.14.2
Nice
Like, I wouldn’t mind if he didn’t upload as often, but I do mind when he says he’ll upload at a certain time and then doesn’t.
please no more do something creative
Apex Legends Loba Shad, we’re begging you!!
Resurrection by erection!
draw loba!!! the new apex character
You need to draw Loba from the new update of Apex Legends SHAD PLEASE
This is gonna be another “samurai” situation. Gonna be seeing this nun for awhile
There is a game on Kickstarter… name is ENEFN..
Is all about a student with a gun and a lot of students dead in a school :/
Post something that’s not boring
Post something that’s not boring
Hey I know of a group I can add you to if you wanna troll/raid
My kik: Slut4AlexJones
Hey I and some trap Friends Are in this kik group: 4chanDegenerate
WARNING – “anonymous” BELOW AND HIS SOCKPUPPET “Bredly”
IS A RUSSIAN SCAMMER PUSHING A PHISHING SITE “FUBARS.PW”.
HE HOPES YOU’LL CLICK SO HE CAN STEAL YOUR FINANCIAL INFORMATION
DO NOT EVER CLICK ANY FUBARS.PW DOMAIN LINK
ACCORDING TO SCAMADVISER.COM: Very low trust review, fubars.pw may not be safe
Facts about fubars.pw
Company data
Country Likelihood Russian Federation: 59% / Netherlands: 41%
FUCK YOU, RUSSIAN CRIMINAL. LEAVE SHADBASE. WE WILL NEVER STOP WARNING EVERYONE HERE ABOUT YOUR PHISHING WEBSITES.
Sexy:
fubars.pw/video-4881.avi
I like it!
For loves of shemale and sissy erotica, here’s a slice of the novel-length THE SISSY AND THE BILLIONAIRE
It starts with Rick/Rita—recently discharged from the Army for crossdressing in the barracks and giving head—going to prison for trusting the wrong people and learning the only way for a feminine male to survive behind bars…
====
Three weeks later I was stepping off a sheriff’s bus at the Gaviota State Prison. The public defender told me I had a choice between a one-year plea bargain or a trial and a possible five-year conviction. Combined with my bad conduct discharge, what he called evidence of my “anti-social behavior,” my unsubstantiated version of the events wouldn’t sell to a jury. My plea would still be a felony but a much lesser one.
As I walked past the throng of prisoners watching the chain of new convicts being led in, it seemed all the attention was focused on me. Guys blew kisses, rubbed their crotch, wolf-whistled, and called me “honey” and “cutie” and “fish.” In that instant I knew what it felt like to be a pretty girl who’d walked into a bar full of drunken guys.
The next two hours were a blur of paperwork and a new mug shot and prints and a physical and a spray down for lice and finally a shower. I was dressed in stiff blue denim pants and a work shirt, and given a roll of cheap linen, towels, a scratchy blanket, toothbrush and a disposable razor. I followed the guard into a huge, three-story cellblock and waited in front of a cell as he called out for the door to be opened.
“Got a new cellmate, Rankin,” said the guard while we waited.
I swallowed heavily as the bars rolled to the side. A big, clean-shaven, thirtyish man, who looked like a bodybuilder lay on his side on the bottom bunk, propped up on his elbow. He eyed me with interest and grinned.
That leer from the muscled bruiser on the bunk froze me, so the guard had to prod me inside with his baton. I looked away from that hungry gaze as I heard the bars roll shut with a clang and the departing footsteps of the guard. I heard the subtle squeak of bedsprings as my cellmate moved on the bunk.
“Look at me, fishie,” he said in the kindest voice I’d heard in weeks.
I turned my head to look at the ground in front of where he’d swung his legs over the edge of the bed and sat up. The faded denim clung to his powerful legs muscles, and his boots looked to be size 13 at least. The guy was big and strong enough to be a wrestler or a football player. Also, from the little glimpse I’d gotten I knew he was ruggedly handsome.
“Don’t be afraid, darling. Look in my eyes.” Again that gentleness.
I slowly raised my eyes to meet his, confirming that he was indeed handsome. Brown haired and hazel-eyed, he was covered with the kind of tattoos I’d associated with prison movies. His teeth were a bit crooked and uneven but they weren’t rotten or missing. They were fixed in an easy grin that was as friendly as it was seductive. I imagined being a cheerleader talking to the quarterback.
“H-hi,” I almost whimpered.
“What’s your name?”
“Ri-Rick.”
“That’s a nice name, Rickie. Mine’s Bill. Folks call me Wild Bill. Wild Bill Rankin. But you can just call me Bill. Or…”
“Or… or what?” I asked, my voice quavering.
“I’ll tell you in a minute. First I want you to stop being so scared. I don’t plan on hurting you. I don’t want to hurt you. Okay, Ricky?”
I nodded my head tightly, though I relaxed a little bit.
“Look,” he said, patting the mattress next to him, “have a seat right here. Right next to me… C’mon, you’ll be okay.”
No sooner had I sat next to him he put a big muscular arm around my shoulders. I could feel his power, which was as reassuring as it was unnerving. He smelled faintly of fresh, masculine sweat, a dizzying manly aroma. It made me a bit weak-kneed.
“You’re just a kid, probably under twenty, right? And never been behind bars?”
“Yes, sir. To both.”
“Ah. ‘Sir.’ Well, that’s one of the things you can call me instead of Bill. But let me ask you something, okay, Rickie? You’ve probably heard, imagined all kinds of bad things about prison haven’t you? Rape and stuff?”
I bit my lip in fear, my gaze locked with his as I nodded again ever so slightly.
He brought his face within a foot of mine, lowering his voice while keeping it soothing. “I don’t want to rape you, Ricky. You can believe that. Okay?”
My eyes misted up in gratitude and I whispered yes.
“No, I don’t want that at all. What I want, Ricky, is for you to give yourself to me freely. Because you want to. I can see in your eyes and how you carry yourself that you’re a sissy—or you’re trying not to be one. Or maybe you’re a gay boy, but I think you’re the first… Aren’t you, Rickie?”
He finished in a tone that declared he had no patience for bullshit. After that scene in the barracks I had to admit I wasn’t a normal dude. I’d sucked my buddy’s dicks and I had enjoyed it. I enjoyed them treating me like a girl. I didn’t want to be a sissy or drag queen or gay guy or anything, but I’d had to do it then to get out of trouble, not knowing it would get me into deeper trouble. Now I was in the deepest trouble. Just because he didn’t want to rape me didn’t mean he wouldn’t.
Admit it, Rita, you loved sucking Dan’s cock and you wanted him to fuck you! And Will too. Maybe especially Will.
I shyly looked down, nodded my head. “I—I’m a girl. Sort of.”
“Look at me, Rickie,” he said, gently.
I looked timidly into his eyes, my lips parted in helpless desire as he closed the short distance between our mouths. I froze there, weak in his grasp as he kissed me with surprising tenderness, as if I were a real girl. Then his tongue pressed through my lips and I felt like I’d dived off a high board, plunging into sudden lust that came out of nowhere.
I thrust my tongue together with his, pressing my mouth more firmly to his, my excited breath snorting through my nostrils and loud, lustful whimpers issuing from my throat. Maybe it was the excitement of knowing I was fully under his power, or the loss of control, of being locked up, or maybe I really was a sissy or a tranny deep down and thus couldn’t help my attraction to a powerful man, but all that mattered was I couldn’t stop myself from giving in to him.
He pulled away, grinning like a dog tossed a succulent steak, and sent every button on my shirt flying across the cell as her tore it open and yanked it off my body. He ordered me to kick off my plastic, prison-issued shoes and lay back on his mattress. “Damn, Rickie,” he laughed. “I knew I had you figured. You’re the hottest bitch I seen in lockup in a long time. Damn, you’re a hot piece of ass!”
I swelled with a strange pride at this compliment that would have freaked me out ten minutes ago, but now turned me on. “It’s Rita,” I moaned. “My girl name is Rita.”
“Like Rita Hayworth,” he chuckled, unbuttoning my convict denims and pulling down the zipper. “I should get a trustee to get you some red hair dye! Oh, fuck, you’re a sexy little bitch, Rita.”
“Yes, sir!”
“You can call me that… or you can call me ‘Daddy,’ because that’s what I’m going to be to you in here. You’re going to be my girl and I’m going to be your daddy. You keep me happy and I keep you safe. Nobody will fuck with you because nobody fucks with Wild Bill’s girl. How do you like that, Rita?”
His words thrilled me even more, feeling his confidence and power, and knowing he was truly a man and would treat me right. How could I not want to submit my sissy ass to him? That’s what I was. I wasn’t on female hormones and I wasn’t just crossdressing for the thrill. I was a submissive, cocksucking sissy in prison, and I was going to learn to love it!
“I want to suck your dick, Daddy!” I squealed. I want to suck your big, hard dick and drink all your cum and suck you off all night long!”
“Now, you’re talking, Rita!” he chortled, unzipping his denims and reaching inside to extract a tool that was at least nine inches long.
Picking my slender naked body up with no more effort than if I were a rag doll, he sat up on the mattress and placed me between his legs, my head over his prick that shuddered on his belly in time with his beating heart. I’d only given head three times before this, all on the same night, yet I was already eager to do this.
I lowered my head and took the hunky convict’s dick into my mouth, amazed at how such soft and delicate skin could be anywhere on such a brute, even a gentle one like him. I took his cock all the way into the back of my throat, forcing myself to go down as far as I could and then pulling back until the head was barely in, licking him hard until I sucked him all the way in. It had been months since my first blowjobs but it might as well have been hours. Within minutes Bill was writhing and moaning.
“Oh, Rita,” he groaned. “You give Daddy such great head. And now Daddy wants to fuck you. He wants to fuck you real bad.”
“Bill,” I said in a tiny, little-girlish voice. “I… I’ve never been fucked before.”
“A virgin! Oh my god!” His eyes shone. The gentleness returned to his expression and voice. “Don’t worry, baby. Daddy will make it good for you. That’s a promise.”
With no effort at all he threw my calves and knees over his shoulders. I could feel his steaming breath on my balls and my butt, which I’d just showered. I shuddered as much from his strong hands as from his hot, wet tongue circling my nervous asshole, slowly loosening it up with gentle moist and warm pressure until I could feel his tongue easing past my easing sphincter muscle.
He set me back to the bed and then flipped me over, encircling my waist with his powerful hands and pulling me up to my hands and knees. It thrilled me how strong he was and how weak I felt in his arms. His cock was still damp from my blowjob so he spit into his palm to give it a fresh coat.
“I’m going to touch my cockhead to your asshole, baby, so just stay loose. Breathe deep and trust me. You do what I say and it will barely hurt at all, and then it will feel like you never dreamed.”
“Yes, Daddy,” I said in my little girl voice, enjoy the perversity of that naughty endearment. Really, he was so big and strong he sort of was my daddy!
I flinched briefly when he touched the tip of his slippery tool to my anal pucker but with a deep breath I kept it loose. I kept breathing as her slowly pushed in. After a moment it hurt a little. I whined involuntarily, so he told me to bear down like I was taking a shit and that would open all of my back door muscles to him.
I pushed and it worked like a charm! Suddenly that large, throbbing dick of his slid all the way up into my rectum, made me whimper with ecstasy as it plowed past my prostate gland. I felt a drop of precum force out and run down my dickshaft. As he slid in, Bill let out a deep protracted groan.
“Oh, you’re so tight, baby. You’re so tight!”
I turned my head to the left to look over my shoulder and thank him. With his cock buried in me he leaned forward and fastened his lips to mine, giving me a deep and lengthy French kiss as he fucked me. I moaned and whimpered and cried, rippling with pleasure at being impaled on this hunky convict’s monster dick.
Five minutes later, me gibbering in delight, he wrapped his hands around my waist, rolled back so his legs were under him, and suddenly I was sitting in his lap, all of his nine inches buried up in me as he fucked me deeply. Now we were both able to turn our heads and kiss even more deeply.
Somehow he managed to free up a hand to jack me off while I was still in his lap and getting pounded so lustfully. There was a steady flow down my shaft from all the prostate juice being squeezed out by his fucking. It coated Bill’s hand and made it even slipperier. I moaned uncontrollably into his mouth, knowing my orgasm was on the verge.
The feel of Bill’s spunk jetting deep in my rectum did the trick. I lowered my head and opened my mouth, hoping to catch a good blast of my own cum, hoping my new daddy would think it was real sexy. Most of it ended on my chin but I got to enjoy the taste of a little. He lay down on the bunk, spooning with me and holding my body to his, making me feel safer than I had in a long time.
I made up my mind I’d do anything for him!
A week later the honeymoon was over. I was just now finding out that one of my duties as Bill’s sissy wife was to “entertain” his closest buddies, all five of them—and all at the same time if they wanted, which they apparently did.
“But why, Daddy?” I moaned. My face was splattered with cum from giving each of them a blowjob, and now he wanted to see me get fucked by every one of them. I only wanted his big dick in my sissy ass, but I had no say in this.
“Because I’ll slap the shit out of you if you don’t, sissy bitch.”
A tear running down my face, I took position bent over with my feet spread wide apart and bracing my hands on the bottom mattress. I heard the sound of a condom wrapper opening—Daddy was clean and so he wouldn’t let anyone fuck me without protection. As his pal Chet asked for some lube I heard the staccato rap of guards’ boot heels drumming down the corridor.
It’s 2020. You can crossdress in the barracks and give people head if you want to.
DO NOT EVER CLICK ANY FUBARS.PW DOMAIN LINK
ACCORDING TO SCAMADVISER.COM: Very low trust review, fubars.pw may not be safe
Facts about fubars.pw
Company data
Country Likelihood Russian Federation: 59% / Netherlands: 41%
FUCK YOU, RUSSIAN CRIMINAL. LEAVE SHADBASE.
Send your dick to Daelu4 on kik to get an ass pic. All dicks are welcome
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Troll him
This guy is making suicidal ppl cut his name into their arm. Do whatever you want with him his Kik: Daelu4
N0T this: specific post, but a combination of previous multiple posts, have formed together posts have made me Glen Ninham, an isolated white Native American freak😬🤷🏻♀️🤤🤪
Shad daddy went for cigs again guess we waiting till he comes back. Take your time bud all the haters will still be checking your page everyday for at least another month or so.
Anyone from North Dakota who would let me cum in there ass?
Nobody lives in North Dakota
North Dakota doesn’t exist
or ohio
That’s weird because North Dakota makes most of the countries oil and is one of the few states that could survive being its own country🤷🏼♀️🤷🏼♀️
I reside in North Dakota but decline the offer. Glad to see more of us on this hellhole.
Beastly comment
Apex legends would be epic
I am not horny but I must coom
I wouldn’t minds more sonic or just more art
.
My man a little ways down posted a full fanfic. Props to them.
you heard of the new apex legend?
A Harvard professor used the corona virus to push for the abolition of the constitution.
Hi shad man I’ve always loved your work you love been an inspiration to start a career in art yet I sadly am missing your posts please go back to at least one post a week
The first one with the face of the second. Her look is so horny! Love your work!
Please do a Labo from Apex Legends pinup
aviota State Prison. The public defender told me I had a choice between a one-year plea bargain or a trial and a possible five-year conviction. Combined with my bad conduct discharge, what he called evidence of my “anti-social behavior,” my unsubstantiated version of the events wouldn’t sell to a jury. My plea would still be a felony but a much lesser one.
As I walked past the throng of prisoners watching the chain of new convicts being led in, it seemed all the attention was focused on me. Guys blew kisses, rubbed their crotch, wolf-whistled, and called me “honey” and “cutie” and “fish.” In that instant I knew what it felt like to be a pretty girl who’d walked into a bar full of drunken guys.
The next two hours were a blur of paperwork and a new mug shot and prints and a physical and a spray down for lice and finally a shower. I was dressed in stiff blue denim pants and a work shirt, and given a roll of cheap linen, towels, a scratchy blanket, toothbrush and a disposable razor. I followed the guard into a huge, three-story cellblock and waited in front of a cell as he called out for the door to be opened.
“Got a new cellmate, Rankin,” said the guard while we waited.
I swallowed heavily as the bars rolled to the side. A big, clean-shaven, thirtyish man, who looked like a bodybuilder lay on his side on the bottom bunk, propped up on his elbow. He eyed me with interest and grinned.
That leer from the muscled bruiser on the bunk froze me, so the guard had to prod me inside with his baton. I looked away from that hungry gaze as I heard the bars roll shut with a clang and the departing footsteps of the guard. I heard the subtle squeak of bedsprings as my cellmate moved on the bunk.
“Look at me, fishie,” he said in the kindest voice I’d heard in weeks.
I turned my head to look at the ground in front of where he’d swung his legs over the edge of the bed and sat up. The faded denim clung to his powerful legs muscles, and his boots looked to be size 13 at least. The guy was big and strong enough to be a wrestler or a football player. Also, from the little glimpse I’d gotten I knew he was ruggedly handsome.
“Don’t be afraid, darling. Look in my eyes.” Again that gentleness.
I slowly raised my eyes to meet his, confirming that he was indeed handsome. Brown haired and hazel-eyed, he was covered with the kind of tattoos I’d associated with prison movies. His teeth were a bit crooked and uneven but they weren’t rotten or missing. They were fixed in an easy grin that was as friendly as it was seductive. I imagined being a cheerleader talking to the quarterback.
“H-hi,” I almost whimpered.
“What’s your name?”
“Ri-Rick.”
“That’s a nice name, Rickie. Mine’s Bill. Folks call me Wild Bill. Wild Bill Rankin. But you can just call me Bill. Or…”
“Or… or what?” I asked, my voice quavering.
“I’ll tell you in a minute. First I want you to stop being so scared. I don’t plan on hurting you. I don’t want to hurt you. Okay, Ricky?”
I nodded my head tightly, though I relaxed a little bit.
“Look,” he said, patting the mattress next to him, “have a seat right here. Right next to me… C’mon, you’ll be okay.”
No sooner had I sat next to him he put a big muscular arm around my shoulders. I could feel his power, which was as reassuring as it was unnerving. He smelled faintly of fresh, masculine sweat, a dizzying manly aroma. It made me a bit weak-kneed.
“You’re just a kid, probably under twenty, right? And never been behind bars?”
“Yes, sir. To both.”
“Ah. ‘Sir.’ Well, that’s one of the things you can call me instead of Bill. But let me ask you something, okay, Rickie? You’ve probably heard, imagined all kinds of bad things about prison haven’t you? Rape and stuff?”
I bit my lip in fear, my gaze locked with his as I nodded again ever so slightly.
He brought his face within a foot of mine, lowering his voice while keeping it soothing. “I don’t want to rape you, Ricky. You can believe that. Okay?”
My eyes misted up in gratitude and I whispered yes.
“No, I don’t want that at all. What I want, Ricky, is for you to give yourself to me freely. Because you want to. I can see in your eyes and how you carry yourself that you’re a sissy—or you’re trying not to be one. Or maybe you’re a gay boy, but I think you’re the first… Aren’t you, Rickie?”
He finished in a tone that declared he had no patience for bullshit. After that scene in the barracks I had to admit I wasn’t a normal dude. I’d sucked my buddy’s dicks and I had enjoyed it. I enjoyed them treating me like a girl. I didn’t want to be a sissy or drag queen or gay guy or anything, but I’d had to do it then to get out of trouble, not knowing it would get me into deeper trouble. Now I was in the deepest trouble. Just because he didn’t want to rape me didn’t mean he wouldn’t.
Admit it, Rita, you loved sucking Dan’s cock and you wanted him to fuck you! And Will too. Maybe especially Will.
I shyly looked down, nodded my head. “I—I’m a girl. Sort of.”
“Look at me, Rickie,” he said, gently.
I looked timidly into his eyes, my lips parted in helpless desire as he closed the short distance between our mouths. I froze there, weak in his grasp as he kissed me with surprising tenderness, as if I were a real girl. Then his tongue pressed through my lips and I felt like I’d dived off a high board, plunging into sudden lust that came out of nowhere.
I thrust my tongue together with his, pressing my mouth more firmly to his, my excited breath snorting through my nostrils and loud, lustful whimpers issuing from my throat. Maybe it was the excitement of knowing I was fully under his power, or the loss of control, of being locked up, or maybe I really was a sissy or a tranny deep down and thus couldn’t help my attraction to a powerful man, but all that mattered was I couldn’t stop myself from giving in to him.
He pulled away, grinning like a dog tossed a succulent steak, and sent every button on my shirt flying across the cell as her tore it open and yanked it off my body. He ordered me to kick off my plastic, prison-issued shoes and lay back on his mattress. “Damn, Rickie,” he laughed. “I knew I had you figured. You’re the hottest bitch I seen in lockup in a long time. Damn, you’re a hot piece of ass!”
I swelled with a strange pride at this compliment that would have freaked me out ten minutes ago, but now turned me on. “It’s Rita,” I moaned. “My girl name is Rita.”
“Like Rita Hayworth,” he chuckled, unbuttoning my convict denims and pulling down the zipper. “I should get a trustee to get you some red hair dye! Oh, fuck, you’re a sexy little bitch, Rita.”
“Yes, sir!”
“You can call me that… or you can call me ‘Daddy,’ because that’s what I’m going to be to you in here. You’re going to be my girl and I’m going to be your daddy. You keep me happy and I keep you safe. Nobody will fuck with you because nobody fucks with Wild Bill’s girl. How do you like that, Rita?”
His words thrilled me even more, feeling his confidence and power, and knowing he was truly a man and would treat me right. How could I not want to submit my sissy ass to him? That’s what I was. I wasn’t on female hormones and I wasn’t just crossdressing for the thrill. I was a submissive, cocksucking sissy in prison, and I was going to learn to love it!
“I want to suck your dick, Daddy!” I squealed. I want to suck your big, hard dick and drink all your cum and suck you off all night long!”
“Now, you’re talking, Rita!” he chortled, unzipping his denims and reaching inside to extract a tool that was at least nine inches long.
Picking my slender naked body up with no more effort than if I were a rag doll, he sat up on the mattress and placed me between his legs, my head over his prick that shuddered on his belly in time with his beating heart. I’d only given head three times before this, all on the same night, yet I was already eager to do this.
I lowered my head and took the hunky convict’s dick into my mouth, amazed at how such soft and delicate skin could be anywhere on such a brute, even a gentle one like him. I took his cock all the way into the back of my throat, forcing myself to go down as far as I could and then pulling back until the head was barely in, licking him hard until I sucked him all the way in. It had been months since my first blowjobs but it might as well have been hours. Within minutes Bill was writhing and moaning.
“Oh, Rita,” he groaned. “You give Daddy such great head. And now Daddy wants to fuck you. He wants to fuck you real bad.”
“Bill,” I said in a tiny, little-girlish voice. “I… I’ve never been fucked before.”
“A virgin! Oh my god!” His eyes shone. The gentleness returned to his expression and voice. “Don’t worry, baby. Daddy will make it good for you. That’s a promise.”
With no effort at all he threw my calves and knees over his shoulders. I could feel his steaming breath on my balls and my butt, which I’d just showered. I shuddered as much from his strong hands as from his hot, wet tongue circling my nervous asshole, slowly loosening it up with gentle moist and warm pressure until I could feel his tongue easing past my easing sphincter muscle.
He set me back to the bed and then flipped me over, encircling my waist with his powerful hands and pulling me up to my hands and knees. It thrilled me how strong he was and how weak I felt in his arms. His cock was still damp from my blowjob so he spit into his palm to give it a fresh coat.
“I’m going to touch my cockhead to your asshole, baby, so just stay loose. Breathe deep and trust me. You do what I say and it will barely hurt at all, and then it will feel like you never dreamed.”
“Yes, Daddy,” I said in my little girl voice, enjoy the perversity of that naughty endearment. Really, he was so big and strong he sort of was my daddy!
I flinched briefly when he touched the tip of his slippery tool to my anal pucker but with a deep breath I kept it loose. I kept breathing as her slowly pushed in. After a moment it hurt a little. I whined involuntarily, so he told me to bear down like I was taking a shit and that would open all of my back door muscles to him.
I pushed and it worked like a charm! Suddenly that large, throbbing dick of his slid all the way up into my rectum, made me whimper with ecstasy as it plowed past my prostate gland. I felt a drop of precum force out and run down my dickshaft. As he slid in, Bill let out a deep protracted groan.
“Oh, you’re so tight, baby. You’re so tight!”
I turned my head to the left to look over my shoulder and thank him. With his cock buried in me he leaned forward and fastened his lips to mine, giving me a deep and lengthy French kiss as he fucked me. I moaned and whimpered and cried, rippling with pleasure at being impaled on this hunky convict’s monster dick.
Five minutes later, me gibbering in delight, he wrapped his hands around my waist, rolled back so his legs were under him, and suddenly I was sitting in his lap, all of his nine inches buried up in me as he fucked me deeply. Now we were both able to turn our heads and kiss even more deeply.
Somehow he managed to free up a hand to jack me off while I was still in his lap and getting pounded so lustfully. There was a steady flow down my shaft from all the prostate juice being squeezed out by his fucking. It coated Bill’s hand and made it even slipperier. I moaned uncontrollably into his mouth, knowing my orgasm was on the verge.
The feel of Bill’s spunk jetting deep in my rectum did the trick. I lowered my head and opened my mouth, hoping to catch a good blast of my own cum, hoping my new daddy would think it was real sexy. Most of it ended on my chin but I got to enjoy the taste of a little. He lay down on the bunk, spooning with me and holding my body to his, making me feel safer than I had in a long time.
I made up my mind I’d do anything for him!
A week later the honeymoon was over. I was just now finding out that one of my duties as Bill’s sissy wife was to “entertain” his closest buddies, all five of them—and all at the same time if they wanted, which they apparently did.
“But why, Daddy?” I moaned. My face was splattered with cum from giving each of them a blowjob, and now he wanted to see me get fucked by every one of them. I only wanted his big dick in my sissy ass, but I had no say in this.
“Because I’ll slap the shit out of you if you don’t, sissy bitch.”
A tear running down my face, I took position bent over with my feet spread wide apart and bracing my hands on the bottom mattress. I heard the sound of a condom wrapper opening—Daddy was clean and so he wouldn’t let anyone fuck me without protection. As his pal Chet asked for some lube I heard the staccato rap of guards’ boot heels drumming down the corridor.
I immediately sat on the mattress and wiped the cum off my face. I reached for my pants like I was putting them on, but I knew nobody would be fooled. Everyone knew about the many daddy-sissy relationships and the loaning out of sissy wives, but because these arrangements reduced violence the guards turned a blind eye to it. They did the same with uniforms. We sissies and the trannies got to modify our uniforms into halter tops, hot pants, even miniskirts, as long as we maintained one regulation set of clothes for state official’s tours and visiting day. Still, you didn’t fuck in front of the C.O.s, the guards.
Three guards including a sergeant came to a stop at our open cell door.
“Inmate M-11428,” barked the sergeant.
“Yes sir?” I asked, fumbling with my skintight denims.
“Captain Janus wants to see you.”
Gratefully I tugged on my denim jeans, humiliated that though I wasn’t really looking forward to the gangbang, my dick was still hard from my predicament. I saw out of the corner of my eye that Bill and his chums were scowling, but defying the guards, especially the captain herself, brought down shit on everybody. As I stood to leave I turned to my cellblock husband.
“Sorry, Daddy,” I said in the little-girl voice I knew he loved.
A reluctant grin broke through his scowl and he jerked his head toward the guards. “Don’t keep the captain waiting.”
As I followed the trio off the cellblock, I recalled briefly meeting Captain Janus during my intake. She was a fairly pretty and buff but shapely blonde in her mid-thirties who had a trace of a German accent. I heard rumors she was an immigrant from Berlin who’d been a citizen for many years, and who had a love of discipline and corporal punishment. When I heard that I thought she would have made a perfect professional dominant, accent and all.
The guards marched me up to an office door, knocked and took me in. A truly breathtaking redhead sat at a receptionist desk. She looked to be in her mid-twenties with hazel brown eyes, and her silky hair flowed over soft shoulders. It was then I noticed with a start she was wearing tailored state denim, an oversize work shirt that had been taken in so it clung to her hourglass figure.
“Is this 11428?” she asked in a voice far too beautiful and demure for this place.
“That’s right, Ange,” grinned the sergeant.
“That’s Angelica,” she scolded with a toss of her head. “You and your men can wait on the sofa or come back when she calls.” She looked me up and down with a smirk of recognition. “I don’t think this one’s going to cause us any trouble.” Then she picked up the phone. “Prisoner Minius is here, Ma’am… Yes, Ma’am.” She turned back to me. “You can go in now. That door over there.” Then she gave me a knowing grin. “By the way, there’s still a little cum under your chin.”
Blushing I rubbed it away and walked to the door. I held my breath and raised my hand to knock.
“She’s already expecting you. Just
Does anybody else notice the shadow doesn’t match in the second picture.
pping off a sheriff’s bus at the Gaviota State Prison. The public defender told me I had a choice between a one-year plea bargain or a trial and a possible five-year conviction. Combined with my bad conduct discharge, what he called evidence of my “anti-social behavior,” my unsubstantiated version of the events wouldn’t sell to a jury. My plea would still be a felony but a much lesser one.
As I walked past the throng of prisoners watching the chain of new convicts being led in, it seemed all the attention was focused on me. Guys blew kisses, rubbed their crotch, wolf-whistled, and called me “honey” and “cutie” and “fish.” In that instant I knew what it felt like to be a pretty girl who’d walked into a bar full of drunken guys.
The next two hours were a blur of paperwork and a new mug shot and prints and a physical and a spray down for lice and finally a shower. I was dressed in stiff blue denim pants and a work shirt, and given a roll of cheap linen, towels, a scratchy blanket, toothbrush and a disposable razor. I followed the guard into a huge, three-story cellblock and waited in front of a cell as he called out for the door to be opened.
“Got a new cellmate, Rankin,” said the guard while we waited.
I swallowed heavily as the bars rolled to the side. A big, clean-shaven, thirtyish man, who looked like a bodybuilder lay on his side on the bottom bunk, propped up on his elbow. He eyed me with interest and grinned.
That leer from the muscled bruiser on the bunk froze me, so the guard had to prod me inside with his baton. I looked away from that hungry gaze as I heard the bars roll shut with a clang and the departing footsteps of the guard. I heard the subtle squeak of bedsprings as my cellmate moved on the bunk.
“Look at me, fishie,” he said in the kindest voice I’d heard in weeks.
I turned my head to look at the ground in front of where he’d swung his legs over the edge of the bed and sat up. The faded denim clung to his powerful legs muscles, and his boots looked to be size 13 at least. The guy was big and strong enough to be a wrestler or a football player. Also, from the little glimpse I’d gotten I knew he was ruggedly handsome.
“Don’t be afraid, darling. Look in my eyes.” Again that gentleness.
I slowly raised my eyes to meet his, confirming that he was indeed handsome. Brown haired and hazel-eyed, he was covered with the kind of tattoos I’d associated with prison movies. His teeth were a bit crooked and uneven but they weren’t rotten or missing. They were fixed in an easy grin that was as friendly as it was seductive. I imagined being a cheerleader talking to the quarterback.
“H-hi,” I almost whimpered.
“What’s your name?”
“Ri-Rick.”
“That’s a nice name, Rickie. Mine’s Bill. Folks call me Wild Bill. Wild Bill Rankin. But you can just call me Bill. Or…”
“Or… or what?” I asked, my voice quavering.
“I’ll tell you in a minute. First I want you to stop being so scared. I don’t plan on hurting you. I don’t want to hurt you. Okay, Ricky?”
I nodded my head tightly, though I relaxed a little bit.
“Look,” he said, patting the mattress next to him, “have a seat right here. Right next to me… C’mon, you’ll be okay.”
No sooner had I sat next to him he put a big muscular arm around my shoulders. I could feel his power, which was as reassuring as it was unnerving. He smelled faintly of fresh, masculine sweat, a dizzying manly aroma. It made me a bit weak-kneed.
“You’re just a kid, probably under twenty, right? And never been behind bars?”
“Yes, sir. To both.”
“Ah. ‘Sir.’ Well, that’s one of the things you can call me instead of Bill. But let me ask you something, okay, Rickie? You’ve probably heard, imagined all kinds of bad things about prison haven’t you? Rape and stuff?”
I bit my lip in fear, my gaze locked with his as I nodded again ever so slightly.
He brought his face within a foot of mine, lowering his voice while keeping it soothing. “I don’t want to rape you, Ricky. You can believe that. Okay?”
My eyes misted up in gratitude and I whispered yes.
“No, I don’t want that at all. What I want, Ricky, is for you to give yourself to me freely. Because you want to. I can see in your eyes and how you carry yourself that you’re a sissy—or you’re trying not to be one. Or maybe you’re a gay boy, but I think you’re the first… Aren’t you, Rickie?”
He finished in a tone that declared he had no patience for bullshit. After that scene in the barracks I had to admit I wasn’t a normal dude. I’d sucked my buddy’s dicks and I had enjoyed it. I enjoyed them treating me like a girl. I didn’t want to be a sissy or drag queen or gay guy or anything, but I’d had to do it then to get out of trouble, not knowing it would get me into deeper trouble. Now I was in the deepest trouble. Just because he didn’t want to rape me didn’t mean he wouldn’t.
Admit it, Rita, you loved sucking Dan’s cock and you wanted him to fuck you! And Will too. Maybe especially Will.
I shyly looked down, nodded my head. “I—I’m a girl. Sort of.”
“Look at me, Rickie,” he said, gently.
I looked timidly into his eyes, my lips parted in helpless desire as he closed the short distance between our mouths. I froze there, weak in his grasp as he kissed me with surprising tenderness, as if I were a real girl. Then his tongue pressed through my lips and I felt like I’d dived off a high board, plunging into sudden lust that came out of nowhere.
I thrust my tongue together with his, pressing my mouth more firmly to his, my excited breath snorting through my nostrils and loud, lustful whimpers issuing from my throat. Maybe it was the excitement of knowing I was fully under his power, or the loss of control, of being locked up, or maybe I really was a sissy or a tranny deep down and thus couldn’t help my attraction to a powerful man, but all that mattered was I couldn’t stop myself from giving in to him.
He pulled away, grinning like a dog tossed a succulent steak, and sent every button on my shirt flying across the cell as her tore it open and yanked it off my body. He ordered me to kick off my plastic, prison-issued shoes and lay back on his mattress. “Damn, Rickie,” he laughed. “I knew I had you figured. You’re the hottest bitch I seen in lockup in a long time. Damn, you’re a hot piece of ass!”
I swelled with a strange pride at this compliment that would have freaked me out ten minutes ago, but now turned me on. “It’s Rita,” I moaned. “My girl name is Rita.”
“Like Rita Hayworth,” he chuckled, unbuttoning my convict denims and pulling down the zipper. “I should get a trustee to get you some red hair dye! Oh, fuck, you’re a sexy little bitch, Rita.”
“Yes, sir!”
“You can call me that… or you can call me ‘Daddy,’ because that’s what I’m going to be to you in here. You’re going to be my girl and I’m going to be your daddy. You keep me happy and I keep you safe. Nobody will fuck with you because nobody fucks with Wild Bill’s girl. How do you like that, Rita?”
His words thrilled me even more, feeling his confidence and power, and knowing he was truly a man and would treat me right. How could I not want to submit my sissy ass to him? That’s what I was. I wasn’t on female hormones and I wasn’t just crossdressing for the thrill. I was a submissive, cocksucking sissy in prison, and I was going to learn to love it!
“I want to suck your dick, Daddy!” I squealed. I want to suck your big, hard dick and drink all your cum and suck you off all night long!”
“Now, you’re talking, Rita!” he chortled, unzipping his denims and reaching inside to extract a tool that was at least nine inches long.
Picking my slender naked body up with no more effort than if I were a rag doll, he sat up on the mattress and placed me between his legs, my head over his prick that shuddered on his belly in time with his beating heart. I’d only given head three times before this, all on the same night, yet I was already eager to do this.
I lowered my head and took the hunky convict’s dick into my mouth, amazed at how such soft and delicate skin could be anywhere on such a brute, even a gentle one like him. I took his cock all the way into the back of my throat, forcing myself to go down as far as I could and then pulling back until the head was barely in, licking him hard until I sucked him all the way in. It had been months since my first blowjobs but it might as well have been hours. Within minutes Bill was writhing and moaning.
“Oh, Rita,” he groaned. “You give Daddy such great head. And now Daddy wants to fuck you. He wants to fuck you real bad.”
“Bill,” I said in a tiny, little-girlish voice. “I… I’ve never been fucked before.”
“A virgin! Oh my god!” His eyes shone. The gentleness returned to his expression and voice. “Don’t worry, baby. Daddy will make it good for you. That’s a promise.”
With no effort at all he threw my calves and knees over his shoulders. I could feel his steaming breath on my balls and my butt, which I’d just showered. I shuddered as much from his strong hands as from his hot, wet tongue circling my nervous asshole, slowly loosening it up with gentle moist and warm pressure until I could feel his tongue easing past my easing sphincter muscle.
He set me back to the bed and then flipped me over, encircling my waist with his powerful hands and pulling me up to my hands and knees. It thrilled me how strong he was and how weak I felt in his arms. His cock was still damp from my blowjob so he spit into his palm to give it a fresh coat.
“I’m going to touch my cockhead to your asshole, baby, so just stay loose. Breathe deep and trust me. You do what I say and it will barely hurt at all, and then it will feel like you never dreamed.”
“Yes, Daddy,” I said in my little girl voice, enjoy the perversity of that naughty endearment. Really, he was so big and strong he sort of was my daddy!
I flinched briefly when he touched the tip of his slippery tool to my anal pucker but with a deep breath I kept it loose. I kept breathing as her slowly pushed in. After a moment it hurt a little. I whined involuntarily, so he told me to bear down like I was taking a shit and that would open all of my back door muscles to him.
I pushed and it worked like a charm! Suddenly that large, throbbing dick of his slid all the way up into my rectum, made me whimper with ecstasy as it plowed past my prostate gland. I felt a drop of precum force out and run down my dickshaft. As he slid in, Bill let out a deep protracted groan.
“Oh, you’re so tight, baby. You’re so tight!”
I turned my head to the left to look over my shoulder and thank him. With his cock buried in me he leaned forward and fastened his lips to mine, giving me a deep and lengthy French kiss as he fucked me. I moaned and whimpered and cried, rippling with pleasure at being impaled on this hunky convict’s monster dick.
Five minutes later, me gibbering in delight, he wrapped his hands around my waist, rolled back so his legs were under him, and suddenly I was sitting in his lap, all of his nine inches buried up in me as he fucked me deeply. Now we were both able to turn our heads and kiss even more deeply.
Somehow he managed to free up a hand to jack me off while I was still in his lap and getting pounded so lustfully. There was a steady flow down my shaft from all the prostate juice being squeezed out by his fucking. It coated Bill’s hand and made it even slipperier. I moaned uncontrollably into his mouth, knowing my orgasm was on the verge.
The feel of Bill’s spunk jetting deep in my rectum did the trick. I lowered my head and opened my mouth, hoping to catch a good blast of my own cum, hoping my new daddy would think it was real sexy. Most of it ended on my chin but I got to enjoy the taste of a little. He lay down on the bunk, spooning with me and holding my body to his, making me feel safer than I had in a long time.
I made up my mind I’d do anything for him!
A week later the honeymoon was over. I was just now finding out that one of my duties as Bill’s sissy wife was to “entertain” his closest buddies, all five of them—and all at the same time if they wanted, which they apparently did.
“But why, Daddy?” I moaned. My face was splattered with cum from giving each of them a blowjob, and now he wanted to see me get fucked by every one of them. I only wanted his big dick in my sissy ass, but I had no say in this.
“Because I’ll slap the shit out of you if you don’t, sissy bitch.”
A tear running down my face, I took position bent over with my feet spread wide apart and bracing my hands on the bottom mattress. I heard the sound of a condom wrapper opening—Daddy was clean and so he wouldn’t let anyone fuck me without protection. As his pal Chet asked for some lube I heard the staccato rap of guards’ boot heels drumming down the corridor.
I immediately sat on the mattress and wiped the cum off my face. I reached for my pants like I was putting them on, but I knew nobody would be fooled. Everyone knew about the many daddy-sissy relationships and the loaning out of sissy wives, but because these arrangements reduced violence the guards turned a blind eye to it. They did the same with uniforms. We sissies and the trannies got to modify our uniforms into halter tops, hot pants, even miniskirts, as long as we maintained one regulation set of clothes for state official’s tours and visiting day. Still, you didn’t fuck in front of the C.O.s, the guards.
Three guards including a sergeant came to a stop at our open cell door.
“Inmate M-11428,” barked the sergeant.
“Yes sir?” I asked, fumbling with my skintight denims.
“Captain Janus wants to see you.”
Gratefully I tugged on my denim jeans, humiliated that though I wasn’t really looking forward to the gangbang, my dick was still hard from my predicament. I saw out of the corner of my eye that Bill and his chums were scowling, but defying the guards, especially the captain herself, brought down shit on everybody. As I stood to leave I turned to my cellblock husband.
“Sorry, Daddy,” I said in the little-girl voice I knew he loved.
A reluctant grin broke through his scowl and he jerked his head toward the guards. “Don’t keep the captain waiting.”
As I followed the trio off the cellblock, I recalled briefly meeting Captain Janus during my intake. She was a fairly pretty and buff but shapely blonde in her mid-thirties who had a trace of a German accent. I heard rumors she was an immigrant from Berlin who’d been a citizen for many years, and who had a love of discipline and corporal punishment. When I heard that I thought she would have made a perfect professional dominant, accent and all.
The guards marched me up to an office door, knocked and took me in. A truly breathtaking redhead sat at a receptionist desk. She looked to be in her mid-twenties with hazel brown eyes, and her silky hair flowed over soft shoulders. It was then I noticed with a start she was wearing tailored state denim, an oversize work shirt that had been taken in so it clung to her hourglass figure.
“Is this 11428?” she asked in a voice far too beautiful and demure for this place.
“That’s right, Ange,” grinned the sergeant.
“That’s Angelica,” she scolded with a toss of her head. “You and your men can wait on the sofa or come back when she calls.” She looked me up and down with a smirk of recognition. “I don’t think this one’s going to cause us any trouble.” Then she picked up the phone. “Prisoner Minius is here, Ma’am… Yes, Ma’am.” She turned back to me. “You can go in now. That door over there.” Then she gave me a knowing grin. “By the way, there’s still a little cum under your chin.”
Blushing I rubbed it away and walked to the door. I held my breath and raised my hand to knock.
“She’s already expecting you. Just
pping off a sheriff’s bus at the Gaviota State Prison. The public defender told me I had a choice between a one-year plea bargain or a trial and a possible five-year conviction. Combined with my bad conduct discharge, what he called evidence of my “anti-social behavior,” my unsubstantiated version of the events wouldn’t sell to a jury. My plea would still be a felony but a much lesser one.
As I walked past the throng of prisoners watching the chain of new convicts being led in, it seemed all the attention was focused on me. Guys blew kisses, rubbed their crotch, wolf-whistled, and called me “honey” and “cutie” and “fish.” In that instant I knew what it felt like to be a pretty girl who’d walked into a bar full of drunken guys.
The next two hours were a blur of paperwork and a new mug shot and prints and a physical and a spray down for lice and finally a shower. I was dressed in stiff blue denim pants and a work shirt, and given a roll of cheap linen, towels, a scratchy blanket, toothbrush and a disposable razor. I followed the guard into a huge, three-story cellblock and waited in front of a cell as he called out for the door to be opened.
“Got a new cellmate, Rankin,” said the guard while we waited.
I swallowed heavily as the bars rolled to the side. A big, clean-shaven, thirtyish man, who looked like a bodybuilder lay on his side on the bottom bunk, propped up on his elbow. He eyed me with interest and grinned.
That leer from the muscled bruiser on the bunk froze me, so the guard had to prod me inside with his baton. I looked away from that hungry gaze as I heard the bars roll shut with a clang and the departing footsteps of the guard. I heard the subtle squeak of bedsprings as my cellmate moved on the bunk.
“Look at me, fishie,” he said in the kindest voice I’d heard in weeks.
I turned my head to look at the ground in front of where he’d swung his legs over the edge of the bed and sat up. The faded denim clung to his powerful legs muscles, and his boots looked to be size 13 at least. The guy was big and strong enough to be a wrestler or a football player. Also, from the little glimpse I’d gotten I knew he was ruggedly handsome.
“Don’t be afraid, darling. Look in my eyes.” Again that gentleness.
I slowly raised my eyes to meet his, confirming that he was indeed handsome. Brown haired and hazel-eyed, he was covered with the kind of tattoos I’d associated with prison movies. His teeth were a bit crooked and uneven but they weren’t rotten or missing. They were fixed in an easy grin that was as friendly as it was seductive. I imagined being a cheerleader talking to the quarterback.
“H-hi,” I almost whimpered.
“What’s your name?”
“Ri-Rick.”
“That’s a nice name, Rickie. Mine’s Bill. Folks call me Wild Bill. Wild Bill Rankin. But you can just call me Bill. Or…”
“Or… or what?” I asked, my voice quavering.
“I’ll tell you in a minute. First I want you to stop being so scared. I don’t plan on hurting you. I don’t want to hurt you. Okay, Ricky?”
I nodded my head tightly, though I relaxed a little bit.
“Look,” he said, patting the mattress next to him, “have a seat right here. Right next to me… C’mon, you’ll be okay.”
No sooner had I sat next to him he put a big muscular arm around my shoulders. I could feel his power, which was as reassuring as it was unnerving. He smelled faintly of fresh, masculine sweat, a dizzying manly aroma. It made me a bit weak-kneed.
“You’re just a kid, probably under twenty, right? And never been behind bars?”
“Yes, sir. To both.”
“Ah. ‘Sir.’ Well, that’s one of the things you can call me instead of Bill. But let me ask you something, okay, Rickie? You’ve probably heard, imagined all kinds of bad things about prison haven’t you? Rape and stuff?”
I bit my lip in fear, my gaze locked with his as I nodded again ever so slightly.
He brought his face within a foot of mine, lowering his voice while keeping it soothing. “I don’t want to rape you, Ricky. You can believe that. Okay?”
My eyes misted up in gratitude and I whispered yes.
“No, I don’t want that at all. What I want, Ricky, is for you to give yourself to me freely. Because you want to. I can see in your eyes and how you carry yourself that you’re a sissy—or you’re trying not to be one. Or maybe you’re a gay boy, but I think you’re the first… Aren’t you, Rickie?”
He finished in a tone that declared he had no patience for bullshit. After that scene in the barracks I had to admit I wasn’t a normal dude. I’d sucked my buddy’s dicks and I had enjoyed it. I enjoyed them treating me like a girl. I didn’t want to be a sissy or drag queen or gay guy or anything, but I’d had to do it then to get out of trouble, not knowing it would get me into deeper trouble. Now I was in the deepest trouble. Just because he didn’t want to rape me didn’t mean he wouldn’t.
Admit it, Rita, you loved sucking Dan’s cock and you wanted him to fuck you! And Will too. Maybe especially Will.
I shyly looked down, nodded my head. “I—I’m a girl. Sort of.”
“Look at me, Rickie,” he said, gently.
I looked timidly into his eyes, my lips parted in helpless desire as he closed the short distance between our mouths. I froze there, weak in his grasp as he kissed me with surprising tenderness, as if I were a real girl. Then his tongue pressed through my lips and I felt like I’d dived off a high board, plunging into sudden lust that came out of nowhere.
I thrust my tongue together with his, pressing my mouth more firmly to his, my excited breath snorting through my nostrils and loud, lustful whimpers issuing from my throat. Maybe it was the excitement of knowing I was fully under his power, or the loss of control, of being locked up, or maybe I really was a sissy or a tranny deep down and thus couldn’t help my attraction to a powerful man, but all that mattered was I couldn’t stop myself from giving in to him.
He pulled away, grinning like a dog tossed a succulent steak, and sent every button on my shirt flying across the cell as her tore it open and yanked it off my body. He ordered me to kick off my plastic, prison-issued shoes and lay back on his mattress. “Damn, Rickie,” he laughed. “I knew I had you figured. You’re the hottest bitch I seen in lockup in a long time. Damn, you’re a hot piece of ass!”
I swelled with a strange pride at this compliment that would have freaked me out ten minutes ago, but now turned me on. “It’s Rita,” I moaned. “My girl name is Rita.”
“Like Rita Hayworth,” he chuckled, unbuttoning my convict denims and pulling down the zipper. “I should get a trustee to get you some red hair dye! Oh, fuck, you’re a sexy little bitch, Rita.”
“Yes, sir!”
“You can call me that… or you can call me ‘Daddy,’ because that’s what I’m going to be to you in here. You’re going to be my girl and I’m going to be your daddy. You keep me happy and I keep you safe. Nobody will fuck with you because nobody fucks with Wild Bill’s girl. How do you like that, Rita?”
His words thrilled me even more, feeling his confidence and power, and knowing he was truly a man and would treat me right. How could I not want to submit my sissy ass to him? That’s what I was. I wasn’t on female hormones and I wasn’t just crossdressing for the thrill. I was a submissive, cocksucking sissy in prison, and I was going to learn to love it!
“I want to suck your dick, Daddy!” I squealed. I want to suck your big, hard dick and drink all your cum and suck you off all night long!”
“Now, you’re talking, Rita!” he chortled, unzipping his denims and reaching inside to extract a tool that was at least nine inches long.
Picking my slender naked body up with no more effort than if I were a rag doll, he sat up on the mattress and placed me between his legs, my head over his prick that shuddered on his belly in time with his beating heart. I’d only given head three times before this, all on the same night, yet I was already eager to do this.
I lowered my head and took the hunky convict’s dick into my mouth, amazed at how such soft and delicate skin could be anywhere on such a brute, even a gentle one like him. I took his cock all the way into the back of my throat, forcing myself to go down as far as I could and then pulling back until the head was barely in, licking him hard until I sucked him all the way in. It had been months since my first blowjobs but it might as well have been hours. Within minutes Bill was writhing and moaning.
“Oh, Rita,” he groaned. “You give Daddy such great head. And now Daddy wants to fuck you. He wants to fuck you real bad.”
“Bill,” I said in a tiny, little-girlish voice. “I… I’ve never been fucked before.”
“A virgin! Oh my god!” His eyes shone. The gentleness returned to his expression and voice. “Don’t worry, baby. Daddy will make it good for you. That’s a promise.”
With no effort at all he threw my calves and knees over his shoulders. I could feel his steaming breath on my balls and my butt, which I’d just showered. I shuddered as much from his strong hands as from his hot, wet tongue circling my nervous asshole, slowly loosening it up with gentle moist and warm pressure until I could feel his tongue easing past my easing sphincter muscle.
He set me back to the bed and then flipped me over, encircling my waist with his powerful hands and pulling me up to my hands and knees. It thrilled me how strong he was and how weak I felt in his arms. His cock was still damp from my blowjob so he spit into his palm to give it a fresh coat.
“I’m going to touch my cockhead to your asshole, baby, so just stay loose. Breathe deep and trust me. You do what I say and it will barely hurt at all, and then it will feel like you never dreamed.”
“Yes, Daddy,” I said in my little girl voice, enjoy the perversity of that naughty endearment. Really, he was so big and strong he sort of was my daddy!
I flinched briefly when he touched the tip of his slippery tool to my anal pucker but with a deep breath I kept it loose. I kept breathing as her slowly pushed in. After a moment it hurt a little. I whined involuntarily, so he told me to bear down like I was taking a shit and that would open all of my back door muscles to him.
I pushed and it worked like a charm! Suddenly that large, throbbing dick of his slid all the way up into my rectum, made me whimper with ecstasy as it plowed past my prostate gland. I felt a drop of precum force out and run down my dickshaft. As he slid in, Bill let out a deep protracted groan.
“Oh, you’re so tight, baby. You’re so tight!”
I turned my head to the left to look over my shoulder and thank him. With his cock buried in me he leaned forward and fastened his lips to mine, giving me a deep and lengthy French kiss as he fucked me. I moaned and whimpered and cried, rippling with pleasure at being impaled on this hunky convict’s monster dick.
Five minutes later, me gibbering in delight, he wrapped his hands around my waist, rolled back so his legs were under him, and suddenly I was sitting in his lap, all of his nine inches buried up in me as he fucked me deeply. Now we were both able to turn our heads and kiss even more deeply.
Somehow he managed to free up a hand to jack me off while I was still in his lap and getting pounded so lustfully. There was a steady flow down my shaft from all the prostate juice being squeezed out by his fucking. It coated Bill’s hand and made it even slipperier. I moaned uncontrollably into his mouth, knowing my orgasm was on the verge.
The feel of Bill’s spunk jetting deep in my rectum did the trick. I lowered my head and opened my mouth, hoping to catch a good blast of my own cum, hoping my new daddy would think it was real sexy. Most of it ended on my chin but I got to enjoy the taste of a little. He lay down on the bunk, spooning with me and holding my body to his, making me feel safer than I had in a long time.
I made up my mind I’d do anything for him!
A week later the honeymoon was over. I was just now finding out that one of my duties as Bill’s sissy wife was to “entertain” his closest buddies, all five of them—and all at the same time if they wanted, which they apparently did.
“But why, Daddy?” I moaned. My face was splattered with cum from giving each of them a blowjob, and now he wanted to see me get fucked by every one of them. I only wanted his big dick in my sissy ass, but I had no say in this.
“Because I’ll slap the shit out of you if you don’t, sissy bitch.”
A tear running down my face, I took position bent over with my feet spread wide apart and bracing my hands on the bottom mattress. I heard the sound of a condom wrapper opening—Daddy was clean and so he wouldn’t let anyone fuck me without protection. As his pal Chet asked for some lube I heard the staccato rap of guards’ boot heels drumming down the corridor.
I immediately sat on the mattress and wiped the cum off my face. I reached for my pants like I was putting them on, but I knew nobody would be fooled. Everyone knew about the many daddy-sissy relationships and the loaning out of sissy wives, but because these arrangements reduced violence the guards turned a blind eye to it. They did the same with uniforms. We sissies and the trannies got to modify our uniforms into halter tops, hot pants, even miniskirts, as long as we maintained one regulation set of clothes for state official’s tours and visiting day. Still, you didn’t fuck in front of the C.O.s, the guards.
Three guards including a sergeant came to a stop at our open cell door.
“Inmate M-11428,” barked the sergeant.
“Yes sir?” I asked, fumbling with my skintight denims.
“Captain Janus wants to see you.”
Gratefully I tugged on my denim jeans, humiliated that though I wasn’t really looking forward to the gangbang, my dick was still hard from my predicament. I saw out of the corner of my eye that Bill and his chums were scowling, but defying the guards, especially the captain herself, brought down shit on everybody. As I stood to leave I turned to my cellblock husband.
“Sorry, Daddy,” I said in the little-girl voice I knew he loved.
A reluctant grin broke through his scowl and he jerked his head toward the guards. “Don’t keep the captain waiting.”
As I followed the trio off the cellblock, I recalled briefly meeting Captain Janus during my intake. She was a fairly pretty and buff but shapely blonde in her mid-thirties who had a trace of a German accent. I heard rumors she was an immigrant from Berlin who’d been a citizen for many years, and who had a love of discipline and corporal punishment. When I heard that I thought she would have made a perfect professional dominant, accent and all.
The guards marched me up to an office door, knocked and took me in. A truly breathtaking redhead sat at a receptionist desk. She looked to be in her mid-twenties with hazel brown eyes, and her silky hair flowed over soft shoulders. It was then I noticed with a start she was wearing tailored state denim, an oversize work shirt that had been taken in so it clung to her hourglass figure.
“Is this 11428?” she asked in a voice far too beautiful and demure for this place.
“That’s right, Ange,” grinned the sergeant.
“That’s Angelica,” she scolded with a toss of her head. “You and your men can wait on the sofa or come back when she calls.” She looked me up and down with a smirk of recognition. “I don’t think this one’s going to cause us any trouble.” Then she picked up the phone. “Prisoner Minius is here, Ma’am… Yes, Ma’am.” She turned back to me. “You can go in now. That door over there.” Then she gave me a knowing grin. “By the way, there’s still a little cum under your chin.”
Blushing I rubbed it away and walked to the door. I held my breath and raised my hand to knock.
“She’s already expecting you. Just
For loves of shemale and sissy erotica, here’s a slice of the novel-length THE SISSY AND THE BILLIONAIRE
It starts with Rick/Rita—recently discharged from the Army for crossdressing in the barracks and giving head—going to prison for trusting the wrong people and learning the only way for a feminine male to survive behind bars…
====
Three weeks later I was stepping off a sheriff’s bus at the Gaviota State Prison. The public defender told me I had a choice between a one-year plea bargain or a trial and a possible five-year conviction. Combined with my bad conduct discharge, what he called evidence of my “anti-social behavior,” my unsubstantiated version of the events wouldn’t sell to a jury. My plea would still be a felony but a much lesser one.
As I walked past the throng of prisoners watching the chain of new convicts being led in, it seemed all the attention was focused on me. Guys blew kisses, rubbed their crotch, wolf-whistled, and called me “honey” and “cutie” and “fish.” In that instant I knew what it felt like to be a pretty girl who’d walked into a bar full of drunken guys.
The next two hours were a blur of paperwork and a new mug shot and prints and a physical and a spray down for lice and finally a shower. I was dressed in stiff blue denim pants and a work shirt, and given a roll of cheap linen, towels, a scratchy blanket, toothbrush and a disposable razor. I followed the guard into a huge, three-story cellblock and waited in front of a cell as he called out for the door to be opened.
“Got a new cellmate, Rankin,” said the guard while we waited.
I swallowed heavily as the bars rolled to the side. A big, clean-shaven, thirtyish man, who looked like a bodybuilder lay on his side on the bottom bunk, propped up on his elbow. He eyed me with interest and grinned.
That leer from the muscled bruiser on the bunk froze me, so the guard had to prod me inside with his baton. I looked away from that hungry gaze as I heard the bars roll shut with a clang and the departing footsteps of the guard. I heard the subtle squeak of bedsprings as my cellmate moved on the bunk.
“Look at me, fishie,” he said in the kindest voice I’d heard in weeks.
I turned my head to look at the ground in front of where he’d swung his legs over the edge of the bed and sat up. The faded denim clung to his powerful legs muscles, and his boots looked to be size 13 at least. The guy was big and strong enough to be a wrestler or a football player. Also, from the little glimpse I’d gotten I knew he was ruggedly handsome.
“Don’t be afraid, darling. Look in my eyes.” Again that gentleness.
I slowly raised my eyes to meet his, confirming that he was indeed handsome. Brown haired and hazel-eyed, he was covered with the kind of tattoos I’d associated with prison movies. His teeth were a bit crooked and uneven but they weren’t rotten or missing. They were fixed in an easy grin that was as friendly as it was seductive. I imagined being a cheerleader talking to the quarterback.
“H-hi,” I almost whimpered.
“What’s your name?”
“Ri-Rick.”
“That’s a nice name, Rickie. Mine’s Bill. Folks call me Wild Bill. Wild Bill Rankin. But you can just call me Bill. Or…”
“Or… or what?” I asked, my voice quavering.
“I’ll tell you in a minute. First I want you to stop being so scared. I don’t plan on hurting you. I don’t want to hurt you. Okay, Ricky?”
I nodded my head tightly, though I relaxed a little bit.
“Look,” he said, patting the mattress next to him, “have a seat right here. Right next to me… C’mon, you’ll be okay.”
No sooner had I sat next to him he put a big muscular arm around my shoulders. I could feel his power, which was as reassuring as it was unnerving. He smelled faintly of fresh, masculine sweat, a dizzying manly aroma. It made me a bit weak-kneed.
“You’re just a kid, probably under twenty, right? And never been behind bars?”
“Yes, sir. To both.”
“Ah. ‘Sir.’ Well, that’s one of the things you can call me instead of Bill. But let me ask you something, okay, Rickie? You’ve probably heard, imagined all kinds of bad things about prison haven’t you? Rape and stuff?”
I bit my lip in fear, my gaze locked with his as I nodded again ever so slightly.
He brought his face within a foot of mine, lowering his voice while keeping it soothing. “I don’t want to rape you, Ricky. You can believe that. Okay?”
My eyes misted up in gratitude and I whispered yes.
“No, I don’t want that at all. What I want, Ricky, is for you to give yourself to me freely. Because you want to. I can see in your eyes and how you carry yourself that you’re a sissy—or you’re trying not to be one. Or maybe you’re a gay boy, but I think you’re the first… Aren’t you, Rickie?”
He finished in a tone that declared he had no patience for bullshit. After that scene in the barracks I had to admit I wasn’t a normal dude. I’d sucked my buddy’s dicks and I had enjoyed it. I enjoyed them treating me like a girl. I didn’t want to be a sissy or drag queen or gay guy or anything, but I’d had to do it then to get out of trouble, not knowing it would get me into deeper trouble. Now I was in the deepest trouble. Just because he didn’t want to rape me didn’t mean he wouldn’t.
Admit it, Rita, you loved sucking Dan’s cock and you wanted him to fuck you! And Will too. Maybe especially Will.
I shyly looked down, nodded my head. “I—I’m a girl. Sort of.”
“Look at me, Rickie,” he said, gently.
I looked timidly into his eyes, my lips parted in helpless desire as he closed the short distance between our mouths. I froze there, weak in his grasp as he kissed me with surprising tenderness, as if I were a real girl. Then his tongue pressed through my lips and I felt like I’d dived off a high board, plunging into sudden lust that came out of nowhere.
I thrust my tongue together with his, pressing my mouth more firmly to his, my excited breath snorting through my nostrils and loud, lustful whimpers issuing from my throat. Maybe it was the excitement of knowing I was fully under his power, or the loss of control, of being locked up, or maybe I really was a sissy or a tranny deep down and thus couldn’t help my attraction to a powerful man, but all that mattered was I couldn’t stop myself from giving in to him.
He pulled away, grinning like a dog tossed a succulent steak, and sent every button on my shirt flying across the cell as her tore it open and yanked it off my body. He ordered me to kick off my plastic, prison-issued shoes and lay back on his mattress. “Damn, Rickie,” he laughed. “I knew I had you figured. You’re the hottest bitch I seen in lockup in a long time. Damn, you’re a hot piece of ass!”
I swelled with a strange pride at this compliment that would have freaked me out ten minutes ago, but now turned me on. “It’s Rita,” I moaned. “My girl name is Rita.”
“Like Rita Hayworth,” he chuckled, unbuttoning my convict denims and pulling down the zipper. “I should get a trustee to get you some red hair dye! Oh, fuck, you’re a sexy little bitch, Rita.”
“Yes, sir!”
“You can call me that… or you can call me ‘Daddy,’ because that’s what I’m going to be to you in here. You’re going to be my girl and I’m going to be your daddy. You keep me happy and I keep you safe. Nobody will fuck with you because nobody fucks with Wild Bill’s girl. How do you like that, Rita?”
His words thrilled me even more, feeling his confidence and power, and knowing he was truly a man and would treat me right. How could I not want to submit my sissy ass to him? That’s what I was. I wasn’t on female hormones and I wasn’t just crossdressing for the thrill. I was a submissive, cocksucking sissy in prison, and I was going to learn to love it!
“I want to suck your dick, Daddy!” I squealed. I want to suck your big, hard dick and drink all your cum and suck you off all night long!”
“Now, you’re talking, Rita!” he chortled, unzipping his denims and reaching inside to extract a tool that was at least nine inches long.
Picking my slender naked body up with no more effort than if I were a rag doll, he sat up on the mattress and placed me between his legs, my head over his prick that shuddered on his belly in time with his beating heart. I’d only given head three times before this, all on the same night, yet I was already eager to do this.
I lowered my head and took the hunky convict’s dick into my mouth, amazed at how such soft and delicate skin could be anywhere on such a brute, even a gentle one like him. I took his cock all the way into the back of my throat, forcing myself to go down as far as I could and then pulling back until the head was barely in, licking him hard until I sucked him all the way in. It had been months since my first blowjobs but it might as well have been hours. Within minutes Bill was writhing and moaning.
“Oh, Rita,” he groaned. “You give Daddy such great head. And now Daddy wants to fuck you. He wants to fuck you real bad.”
“Bill,” I said in a tiny, little-girlish voice. “I… I’ve never been fucked before.”
“A virgin! Oh my god!” His eyes shone. The gentleness returned to his expression and voice. “Don’t worry, baby. Daddy will make it good for you. That’s a promise.”
With no effort at all he threw my calves and knees over his shoulders. I could feel his steaming breath on my balls and my butt, which I’d just showered. I shuddered as much from his strong hands as from his hot, wet tongue circling my nervous asshole, slowly loosening it up with gentle moist and warm pressure until I could feel his tongue easing past my easing sphincter muscle.
He set me back to the bed and then flipped me over, encircling my waist with his powerful hands and pulling me up to my hands and knees. It thrilled me how strong he was and how weak I felt in his arms. His cock was still damp from my blowjob so he spit into his palm to give it a fresh coat.
“I’m going to touch my cockhead to your asshole, baby, so just stay loose. Breathe deep and trust me. You do what I say and it will barely hurt at all, and then it will feel like you never dreamed.”
“Yes, Daddy,” I said in my little girl voice, enjoy the perversity of that naughty endearment. Really, he was so big and strong he sort of was my daddy!
I flinched briefly when he touched the tip of his slippery tool to my anal pucker but with a deep breath I kept it loose. I kept breathing as her slowly pushed in. After a moment it hurt a little. I whined involuntarily, so he told me to bear down like I was taking a shit and that would open all of my back door muscles to him.
I pushed and it worked like a charm! Suddenly that large, throbbing dick of his slid all the way up into my rectum, made me whimper with ecstasy as it plowed past my prostate gland. I felt a drop of precum force out and run down my dickshaft. As he slid in, Bill let out a deep protracted groan.
“Oh, you’re so tight, baby. You’re so tight!”
I turned my head to the left to look over my shoulder and thank him. With his cock buried in me he leaned forward and fastened his lips to mine, giving me a deep and lengthy French kiss as he fucked me. I moaned and whimpered and cried, rippling with pleasure at being impaled on this hunky convict’s monster dick.
Five minutes later, me gibbering in delight, he wrapped his hands around my waist, rolled back so his legs were under him, and suddenly I was sitting in his lap, all of his nine inches buried up in me as he fucked me deeply. Now we were both able to turn our heads and kiss even more deeply.
Somehow he managed to free up a hand to jack me off while I was still in his lap and getting pounded so lustfully. There was a steady flow down my shaft from all the prostate juice being squeezed out by his fucking. It coated Bill’s hand and made it even slipperier. I moaned uncontrollably into his mouth, knowing my orgasm was on the verge.
The feel of Bill’s spunk jetting deep in my rectum did the trick. I lowered my head and opened my mouth, hoping to catch a good blast of my own cum, hoping my new daddy would think it was real sexy. Most of it ended on my chin but I got to enjoy the taste of a little. He lay down on the bunk, spooning with me and holding my body to his, making me feel safer than I had in a long time.
I made up my mind I’d do anything for him!
A week later the honeymoon was over. I was just now finding out that one of my duties as Bill’s sissy wife was to “entertain” his closest buddies, all five of them—and all at the same time if they wanted, which they apparently did.
“But why, Daddy?” I moaned. My face was splattered with cum from giving each of them a blowjob, and now he wanted to see me get fucked by every one of them. I only wanted his big dick in my sissy ass, but I had no say in this.
“Because I’ll slap the shit out of you if you don’t, sissy bitch.”
A tear running down my face, I took position bent over with my feet spread wide apart and bracing my hands on the bottom mattress. I heard the sound of a condom wrapper opening—Daddy was clean and so he wouldn’t let anyone fuck me without protection. As his pal Chet asked for some lube I heard the staccato rap of guards’ boot heels drumming down the corridor.
I immediately sat on the mattress and wiped the cum off my face. I reached for my pants like I was putting them on, but I knew nobody would be fooled. Everyone knew about the many daddy-sissy relationships and the loaning out of sissy wives, but because these arrangements reduced violence the guards turned a blind eye to it. They did the same with uniforms. We sissies and the trannies got to modify our uniforms into halter tops, hot pants, even miniskirts, as long as we maintained one regulation set of clothes for state official’s tours and visiting day. Still, you didn’t fuck in front of the C.O.s, the guards.
Three guards including a sergeant came to a stop at our open cell door.
“Inmate M-11428,” barked the sergeant.
“Yes sir?” I asked, fumbling with my skintight denims.
“Captain Janus wants to see you.”
Gratefully I tugged on my denim jeans, humiliated that though I wasn’t really looking forward to the gangbang, my dick was still hard from my predicament. I saw out of the corner of my eye that Bill and his chums were scowling, but defying the guards, especially the captain herself, brought down shit on everybody. As I stood to leave I turned to my cellblock husband.
“Sorry, Daddy,” I said in the little-girl voice I knew he loved.
A reluctant grin broke through his scowl and he jerked his head toward the guards. “Don’t keep the captain waiting.”
As I followed the trio off the cellblock, I recalled briefly meeting Captain Janus during my intake. She was a fairly pretty and buff but shapely blonde in her mid-thirties who had a trace of a German accent. I heard rumors she was an immigrant from Berlin who’d been a citizen for many years, and who had a love of discipline and corporal punishment. When I heard that I thought she would have made a perfect professional dominant, accent and all.
The guards marched me up to an office door, knocked and took me in. A truly breathtaking redhead sat at a receptionist desk. She looked to be in her mid-twenties with hazel brown eyes, and her silky hair flowed over soft shoulders. It was then I noticed with a start she was wearing tailored state denim, an oversize work shirt that had been taken in so it clung to her hourglass figure.
“Is this 11428?” she asked in a voice far too beautiful and demure for this place.
“That’s right, Ange,” grinned the sergeant.
“That’s Angelica,” she scolded with a toss of her head. “You and your men can wait on the sofa or come back when she calls.” She looked me up and down with a smirk of recognition. “I don’t think this one’s going to cause us any trouble.” Then she picked up the phone. “Prisoner Minius is here, Ma’am… Yes, Ma’am.” She turned back to me. “You can go in now. That door over there.” Then she gave me a knowing grin. “By the way, there’s still a little cum under your chin.”
Blushing I rubbed it away and walked to the door. I held my breath and raised my hand to knock.
“She’s already expecting you. Just go in… Rita.” She winked at me and then returned to her paperwork.
[after prison “Rita” gets a job as a personal assistant to a billionaire – an heiress.]
ion. Combined with my bad conduct discharge, what he called evidence of my “anti-social behavior,” my unsubstantiated version of the events wouldn’t sell to a jury. My plea would still be a felony but a much lesser one.
As I walked past the throng of prisoners watching the chain of new convicts being led in, it seemed all the attention was focused on me. Guys blew kisses, rubbed their crotch, wolf-whistled, and called me “honey” and “cutie” and “fish.” In that instant I knew what it felt like to be a pretty girl who’d walked into a bar full of drunken guys.
The next two hours were a blur of paperwork and a new mug shot and prints and a physical and a spray down for lice and finally a shower. I was dressed in stiff blue denim pants and a work shirt, and given a roll of cheap linen, towels, a scratchy blanket, toothbrush and a disposable razor. I followed the guard into a huge, three-story cellblock and waited in front of a cell as he called out for the door to be opened.
“Got a new cellmate, Rankin,” said the guard while we waited.
I swallowed heavily as the bars rolled to the side. A big, clean-shaven, thirtyish man, who looked like a bodybuilder lay on his side on the bottom bunk, propped up on his elbow. He eyed me with interest and grinned.
That leer from the muscled bruiser on the bunk froze me, so the guard had to prod me inside with his baton. I looked away from that hungry gaze as I heard the bars roll shut with a clang and the departing footsteps of the guard. I heard the subtle squeak of bedsprings as my cellmate moved on the bunk.
“Look at me, fishie,” he said in the kindest voice I’d heard in weeks.
I turned my head to look at the ground in front of where he’d swung his legs over the edge of the bed and sat up. The faded denim clung to his powerful legs muscles, and his boots looked to be size 13 at least. The guy was big and strong enough to be a wrestler or a football player. Also, from the little glimpse I’d gotten I knew he was ruggedly handsome.
“Don’t be afraid, darling. Look in my eyes.” Again that gentleness.
I slowly raised my eyes to meet his, confirming that he was indeed handsome. Brown haired and hazel-eyed, he was covered with the kind of tattoos I’d associated with prison movies. His teeth were a bit crooked and uneven but they weren’t rotten or missing. They were fixed in an easy grin that was as friendly as it was seductive. I imagined being a cheerleader talking to the quarterback.
“H-hi,” I almost whimpered.
“What’s your name?”
“Ri-Rick.”
“That’s a nice name, Rickie. Mine’s Bill. Folks call me Wild Bill. Wild Bill Rankin. But you can just call me Bill. Or…”
“Or… or what?” I asked, my voice quavering.
“I’ll tell you in a minute. First I want you to stop being so scared. I don’t plan on hurting you. I don’t want to hurt you. Okay, Ricky?”
I nodded my head tightly, though I relaxed a little bit.
“Look,” he said, patting the mattress next to him, “have a seat right here. Right next to me… C’mon, you’ll be okay.”
No sooner had I sat next to him he put a big muscular arm around my shoulders. I could feel his power, which was as reassuring as it was unnerving. He smelled faintly of fresh, masculine sweat, a dizzying manly aroma. It made me a bit weak-kneed.
“You’re just a kid, probably under twenty, right? And never been behind bars?”
“Yes, sir. To both.”
“Ah. ‘Sir.’ Well, that’s one of the things you can call me instead of Bill. But let me ask you something, okay, Rickie? You’ve probably heard, imagined all kinds of bad things about prison haven’t you? Rape and stuff?”
I bit my lip in fear, my gaze locked with his as I nodded again ever so slightly.
He brought his face within a foot of mine, lowering his voice while keeping it soothing. “I don’t want to rape you, Ricky. You can believe that. Okay?”
My eyes misted up in gratitude and I whispered yes.
“No, I don’t want that at all. What I want, Ricky, is for you to give yourself to me freely. Because you want to. I can see in your eyes and how you carry yourself that you’re a sissy—or you’re trying not to be one. Or maybe you’re a gay boy, but I think you’re the first… Aren’t you, Rickie?”
He finished in a tone that declared he had no patience for bullshit. After that scene in the barracks I had to admit I wasn’t a normal dude. I’d sucked my buddy’s dicks and I had enjoyed it. I enjoyed them treating me like a girl. I didn’t want to be a sissy or drag queen or gay guy or anything, but I’d had to do it then to get out of trouble, not knowing it would get me into deeper trouble. Now I was in the deepest trouble. Just because he didn’t want to rape me didn’t mean he wouldn’t.
Admit it, Rita, you loved sucking Dan’s cock and you wanted him to fuck you! And Will too. Maybe especially Will.
I shyly looked down, nodded my head. “I—I’m a girl. Sort of.”
“Look at me, Rickie,” he said, gently.
I looked timidly into his eyes, my lips parted in helpless desire as he closed the short distance between our mouths. I froze there, weak in his grasp as he kissed me with surprising tenderness, as if I were a real girl. Then his tongue pressed through my lips and I felt like I’d dived off a high board, plunging into sudden lust that came out of nowhere.
I thrust my tongue together with his, pressing my mouth more firmly to his, my excited breath snorting through my nostrils and loud, lustful whimpers issuing from my throat. Maybe it was the excitement of knowing I was fully under his power, or the loss of control, of being locked up, or maybe I really was a sissy or a tranny deep down and thus couldn’t help my attraction to a powerful man, but all that mattered was I couldn’t stop myself from giving in to him.
He pulled away, grinning like a dog tossed a succulent steak, and sent every button on my shirt flying across the cell as her tore it open and yanked it off my body. He ordered me to kick off my plastic, prison-issued shoes and lay back on his mattress. “Damn, Rickie,” he laughed. “I knew I had you figured. You’re the hottest bitch I seen in lockup in a long time. Damn, you’re a hot piece of ass!”
I swelled with a strange pride at this compliment that would have freaked me out ten minutes ago, but now turned me on. “It’s Rita,” I moaned. “My girl name is Rita.”
“Like Rita Hayworth,” he chuckled, unbuttoning my convict denims and pulling down the zipper. “I should get a trustee to get you some red hair dye! Oh, fuck, you’re a sexy little bitch, Rita.”
“Yes, sir!”
“You can call me that… or you can call me ‘Daddy,’ because that’s what I’m going to be to you in here. You’re going to be my girl and I’m going to be your daddy. You keep me happy and I keep you safe. Nobody will fuck with you because nobody fucks with Wild Bill’s girl. How do you like that, Rita?”
His words thrilled me even more, feeling his confidence and power, and knowing he was truly a man and would treat me right. How could I not want to submit my sissy ass to him? That’s what I was. I wasn’t on female hormones and I wasn’t just crossdressing for the thrill. I was a submissive, cocksucking sissy in prison, and I was going to learn to love it!
“I want to suck your dick, Daddy!” I squealed. I want to suck your big, hard dick and drink all your cum and suck you off all night long!”
“Now, you’re talking, Rita!” he chortled, unzipping his denims and reaching inside to extract a tool that was at least nine inches long.
Picking my slender naked body up with no more effort than if I were a rag doll, he sat up on the mattress and placed me between his legs, my head over his prick that shuddered on his belly in time with his beating heart. I’d only given head three times before this, all on the same night, yet I was already eager to do this.
I lowered my head and took the hunky convict’s dick into my mouth, amazed at how such soft and delicate skin could be anywhere on such a brute, even a gentle one like him. I took his cock all the way into the back of my throat, forcing myself to go down as far as I could and then pulling back until the head was barely in, licking him hard until I sucked him all the way in. It had been months since my first blowjobs but it might as well have been hours. Within minutes Bill was writhing and moaning.
“Oh, Rita,” he groaned. “You give Daddy such great head. And now Daddy wants to fuck you. He wants to fuck you real bad.”
“Bill,” I said in a tiny, little-girlish voice. “I… I’ve never been fucked before.”
“A virgin! Oh my god!” His eyes shone. The gentleness returned to his expression and voice. “Don’t worry, baby. Daddy will make it good for you. That’s a promise.”
With no effort at all he threw my calves and knees over his shoulders. I could feel his steaming breath on my balls and my butt, which I’d just showered. I shuddered as much from his strong hands as from his hot, wet tongue circling my nervous asshole, slowly loosening it up with gentle moist and warm pressure until I could feel his tongue easing past my easing sphincter muscle.
He set me back to the bed and then flipped me over, encircling my waist with his powerful hands and pulling me up to my hands and knees. It thrilled me how strong he was and how weak I felt in his arms. His cock was still damp from my blowjob so he spit into his palm to give it a fresh coat.
“I’m going to touch my cockhead to your asshole, baby, so just stay loose. Breathe deep and trust me. You do what I say and it will barely hurt at all, and then it will feel like you never dreamed.”
“Yes, Daddy,” I said in my little girl voice, enjoy the perversity of that naughty endearment. Really, he was so big and strong he sort of was my daddy!
I flinched briefly when he touched the tip of his slippery tool to my anal pucker but with a deep breath I kept it loose. I kept breathing as her slowly pushed in. After a moment it hurt a little. I whined involuntarily, so he told me to bear down like I was taking a shit and that would open all of my back door muscles to him.
I pushed and it worked like a charm! Suddenly that large, throbbing dick of his slid all the way up into my rectum, made me whimper with ecstasy as it plowed past my prostate gland. I felt a drop of precum force out and run down my dickshaft. As he slid in, Bill let out a deep protracted groan.
“Oh, you’re so tight, baby. You’re so tight!”
I turned my head to the left to look over my shoulder and thank him. With his cock buried in me he leaned forward and fastened his lips to mine, giving me a deep and lengthy French kiss as he fucked me. I moaned and whimpered and cried, rippling with pleasure at being impaled on this hunky convict’s monster dick.
Five minutes later, me gibbering in delight, he wrapped his hands around my waist, rolled back so his legs were under him, and suddenly I was sitting in his lap, all of his nine inches buried up in me as he fucked me deeply. Now we were both able to turn our heads and kiss even more deeply.
Somehow he managed to free up a hand to jack me off while I was still in his lap and getting pounded so lustfully. There was a steady flow down my shaft from all the prostate juice being squeezed out by his fucking. It coated Bill’s hand and made it even slipperier. I moaned uncontrollably into his mouth, knowing my orgasm was on the verge.
The feel of Bill’s spunk jetting deep in my rectum did the trick. I lowered my head and opened my mouth, hoping to catch a good blast of my own cum, hoping my new daddy would think it was real sexy. Most of it ended on my chin but I got to enjoy the taste of a little. He lay down on the bunk, spooning with me and holding my body to his, making me feel safer than I had in a long time.
I made up my mind I’d do anything for him!
A week later the honeymoon was over. I was just now finding out that one of my duties as Bill’s sissy wife was to “entertain” his closest buddies, all five of them—and all at the same time if they wanted, which they apparently did.
“But why, Daddy?” I moaned. My face was splattered with cum from giving each of them a blowjob, and now he wanted to see me get fucked by every one of them. I only wanted his big dick in my sissy ass, but I had no say in this.
“Because I’ll slap the shit out of you if you don’t, sissy bitch.”
A tear running down my face, I took position bent over with my feet spread wide apart and bracing my hands on the bottom mattress. I heard the sound of a condom wrapper opening—Daddy was clean and so he wouldn’t let anyone fuck me without protection. As his pal Chet asked for some lube I heard the staccato rap of guards’ boot heels drumming down the corridor.
I immediately sat on the mattress and wiped the cum off my face. I reached for my pants like I was putting them on, but I knew nobody would be fooled. Everyone knew about the many daddy-sissy relationships and the loaning out of sissy wives, but because these arrangements reduced violence the guards turned a blind eye to it. They did the same with uniforms. We sissies and the trannies got to modify our uniforms into halter tops, hot pants, even miniskirts, as long as we maintained one regulation set of clothes for state official’s tours and visiting day. Still, you didn’t fuck in front of the C.O.s, the guards.
Three guards including a sergeant came to a stop at our open cell door.
“Inmate M-11428,” barked the sergeant.
“Yes sir?” I asked, fumbling with my skintight denims.
“Captain Janus wants to see you.”
Gratefully I tugged on my denim jeans, humiliated that though I wasn’t really looking forward to the gangbang, my dick was still hard from my predicament. I saw out of the corner of my eye that Bill and his chums were scowling, but defying the guards, especially the captain herself, brought down shit on everybody. As I stood to leave I turned to my cellblock husband.
“Sorry, Daddy,” I said in the little-girl voice I knew he loved.
A reluctant grin broke through his scowl and he jerked his head toward the guards. “Don’t keep the captain waiting.”
As I followed the trio off the cellblock, I recalled briefly meeting Captain Janus during my intake. She was a fairly pretty and buff but shapely blonde in her mid-thirties who had a trace of a German accent. I heard rumors she was an immigrant from Berlin who’d been a citizen for many years, and who had a love of discipline and corporal punishment. When I heard that I thought she would have made a perfect professional dominant, accent and all.
The guards marched me up to an office door, knocked and took me in. A truly breathtaking redhead sat at a receptionist desk. She looked to be in her mid-twenties with hazel brown eyes, and her silky hair flowed over soft shoulders. It was then I noticed with a start she was wearing tailored state denim, an oversize work shirt that had been taken in so it clung to her hourglass figure.
“Is this 11428?” she asked in a voice far too beautiful and demure for this place.
“That’s right, Ange,” grinned the sergeant.
“That’s Angelica,” she scolded with a toss of her head. “You and your men can wait on the sofa or come back when she calls.” She looked me up and down with a smirk of recognition. “I don’t think this one’s going to cause us any trouble.” Then she picked up the phone. “Prisoner Minius is here, Ma’am… Yes, Ma’am.” She turned back to me. “You can go in now. That door over there.” Then she gave me a knowing grin. “By the way, there’s still a little cum under your chin.”
Blushing I rubbed it away and walked to the door. I held my breath and raised my hand to knock.
“She’s already expecting you. Just
pping off a sheriff’s bus at the Gaviota State Prison. The public defender told me I had a choice between a one-year plea bargain or a trial and a possible five-year conviction. Combined with my bad conduct discharge, what he called evidence of my “anti-social behavior,” my unsubstantiated version of the events wouldn’t sell to a jury. My plea would still be a felony but a much lesser one.
As I walked past the throng of prisoners watching the chain of new convicts being led in, it seemed all the attention was focused on me. Guys blew kisses, rubbed their crotch, wolf-whistled, and called me “honey” and “cutie” and “fish.” In that instant I knew what it felt like to be a pretty girl who’d walked into a bar full of drunken guys.
The next two hours were a blur of paperwork and a new mug shot and prints and a physical and a spray down for lice and finally a shower. I was dressed in stiff blue denim pants and a work shirt, and given a roll of cheap linen, towels, a scratchy blanket, toothbrush and a disposable razor. I followed the guard into a huge, three-story cellblock and waited in front of a cell as he called out for the door to be opened.
“Got a new cellmate, Rankin,” said the guard while we waited.
I swallowed heavily as the bars rolled to the side. A big, clean-shaven, thirtyish man, who looked like a bodybuilder lay on his side on the bottom bunk, propped up on his elbow. He eyed me with interest and grinned.
That leer from the muscled bruiser on the bunk froze me, so the guard had to prod me inside with his baton. I looked away from that hungry gaze as I heard the bars roll shut with a clang and the departing footsteps of the guard. I heard the subtle squeak of bedsprings as my cellmate moved on the bunk.
“Look at me, fishie,” he said in the kindest voice I’d heard in weeks.
I turned my head to look at the ground in front of where he’d swung his legs over the edge of the bed and sat up. The faded denim clung to his powerful legs muscles, and his boots looked to be size 13 at least. The guy was big and strong enough to be a wrestler or a football player. Also, from the little glimpse I’d gotten I knew he was ruggedly handsome.
“Don’t be afraid, darling. Look in my eyes.” Again that gentleness.
I slowly raised my eyes to meet his, confirming that he was indeed handsome. Brown haired and hazel-eyed, he was covered with the kind of tattoos I’d associated with prison movies. His teeth were a bit crooked and uneven but they weren’t rotten or missing. They were fixed in an easy grin that was as friendly as it was seductive. I imagined being a cheerleader talking to the quarterback.
“H-hi,” I almost whimpered.
“What’s your name?”
“Ri-Rick.”
“That’s a nice name, Rickie. Mine’s Bill. Folks call me Wild Bill. Wild Bill Rankin. But you can just call me Bill. Or…”
“Or… or what?” I asked, my voice quavering.
“I’ll tell you in a minute. First I want you to stop being so scared. I don’t plan on hurting you. I don’t want to hurt you. Okay, Ricky?”
I nodded my head tightly, though I relaxed a little bit.
“Look,” he said, patting the mattress next to him, “have a seat right here. Right next to me… C’mon, you’ll be okay.”
No sooner had I sat next to him he put a big muscular arm around my shoulders. I could feel his power, which was as reassuring as it was unnerving. He smelled faintly of fresh, masculine sweat, a dizzying manly aroma. It made me a bit weak-kneed.
“You’re just a kid, probably under twenty, right? And never been behind bars?”
“Yes, sir. To both.”
“Ah. ‘Sir.’ Well, that’s one of the things you can call me instead of Bill. But let me ask you something, okay, Rickie? You’ve probably heard, imagined all kinds of bad things about prison haven’t you? Rape and stuff?”
I bit my lip in fear, my gaze locked with his as I nodded again ever so slightly.
He brought his face within a foot of mine, lowering his voice while keeping it soothing. “I don’t want to rape you, Ricky. You can believe that. Okay?”
My eyes misted up in gratitude and I whispered yes.
“No, I don’t want that at all. What I want, Ricky, is for you to give yourself to me freely. Because you want to. I can see in your eyes and how you carry yourself that you’re a sissy—or you’re trying not to be one. Or maybe you’re a gay boy, but I think you’re the first… Aren’t you, Rickie?”
He finished in a tone that declared he had no patience for bullshit. After that scene in the barracks I had to admit I wasn’t a normal dude. I’d sucked my buddy’s dicks and I had enjoyed it. I enjoyed them treating me like a girl. I didn’t want to be a sissy or drag queen or gay guy or anything, but I’d had to do it then to get out of trouble, not knowing it would get me into deeper trouble. Now I was in the deepest trouble. Just because he didn’t want to rape me didn’t mean he wouldn’t.
Admit it, Rita, you loved sucking Dan’s cock and you wanted him to fuck you! And Will too. Maybe especially Will.
I shyly looked down, nodded my head. “I—I’m a girl. Sort of.”
“Look at me, Rickie,” he said, gently.
I looked timidly into his eyes, my lips parted in helpless desire as he closed the short distance between our mouths. I froze there, weak in his grasp as he kissed me with surprising tenderness, as if I were a real girl. Then his tongue pressed through my lips and I felt like I’d dived off a high board, plunging into sudden lust that came out of nowhere.
I thrust my tongue together with his, pressing my mouth more firmly to his, my excited breath snorting through my nostrils and loud, lustful whimpers issuing from my throat. Maybe it was the excitement of knowing I was fully under his power, or the loss of control, of being locked up, or maybe I really was a sissy or a tranny deep down and thus couldn’t help my attraction to a powerful man, but all that mattered was I couldn’t stop myself from giving in to him.
He pulled away, grinning like a dog tossed a succulent steak, and sent every button on my shirt flying across the cell as her tore it open and yanked it off my body. He ordered me to kick off my plastic, prison-issued shoes and lay back on his mattress. “Damn, Rickie,” he laughed. “I knew I had you figured. You’re the hottest bitch I seen in lockup in a long time. Damn, you’re a hot piece of ass!”
I swelled with a strange pride at this compliment that would have freaked me out ten minutes ago, but now turned me on. “It’s Rita,” I moaned. “My girl name is Rita.”
“Like Rita Hayworth,” he chuckled, unbuttoning my convict denims and pulling down the zipper. “I should get a trustee to get you some red hair dye! Oh, fuck, you’re a sexy little bitch, Rita.”
“Yes, sir!”
“You can call me that… or you can call me ‘Daddy,’ because that’s what I’m going to be to you in here. You’re going to be my girl and I’m going to be your daddy. You keep me happy and I keep you safe. Nobody will fuck with you because nobody fucks with Wild Bill’s girl. How do you like that, Rita?”
His words thrilled me even more, feeling his confidence and power, and knowing he was truly a man and would treat me right. How could I not want to submit my sissy ass to him? That’s what I was. I wasn’t on female hormones and I wasn’t just crossdressing for the thrill. I was a submissive, cocksucking sissy in prison, and I was going to learn to love it!
“I want to suck your dick, Daddy!” I squealed. I want to suck your big, hard dick and drink all your cum and suck you off all night long!”
“Now, you’re talking, Rita!” he chortled, unzipping his denims and reaching inside to extract a tool that was at least nine inches long.
Picking my slender naked body up with no more effort than if I were a rag doll, he sat up on the mattress and placed me between his legs, my head over his prick that shuddered on his belly in time with his beating heart. I’d only given head three times before this, all on the same night, yet I was already eager to do this.
I lowered my head and took the hunky convict’s dick into my mouth, amazed at how such soft and delicate skin could be anywhere on such a brute, even a gentle one like him. I took his cock all the way into the back of my throat, forcing myself to go down as far as I could and then pulling back until the head was barely in, licking him hard until I sucked him all the way in. It had been months since my first blowjobs but it might as well have been hours. Within minutes Bill was writhing and moaning.
“Oh, Rita,” he groaned. “You give Daddy such great head. And now Daddy wants to fuck you. He wants to fuck you real bad.”
“Bill,” I said in a tiny, little-girlish voice. “I… I’ve never been fucked before.”
“A virgin! Oh my god!” His eyes shone. The gentleness returned to his expression and voice. “Don’t worry, baby. Daddy will make it good for you. That’s a promise.”
With no effort at all he threw my calves and knees over his shoulders. I could feel his steaming breath on my balls and my butt, which I’d just showered. I shuddered as much from his strong hands as from his hot, wet tongue circling my nervous asshole, slowly loosening it up with gentle moist and warm pressure until I could feel his tongue easing past my easing sphincter muscle.
He set me back to the bed and then flipped me over, encircling my waist with his powerful hands and pulling me up to my hands and knees. It thrilled me how strong he was and how weak I felt in his arms. His cock was still damp from my blowjob so he spit into his palm to give it a fresh coat.
“I’m going to touch my cockhead to your asshole, baby, so just stay loose. Breathe deep and trust me. You do what I say and it will barely hurt at all, and then it will feel like you never dreamed.”
“Yes, Daddy,” I said in my little girl voice, enjoy the perversity of that naughty endearment. Really, he was so big and strong he sort of was my daddy!
I flinched briefly when he touched the tip of his slippery tool to my anal pucker but with a deep breath I kept it loose. I kept breathing as her slowly pushed in. After a moment it hurt a little. I whined involuntarily, so he told me to bear down like I was taking a shit and that would open all of my back door muscles to him.
I pushed and it worked like a charm! Suddenly that large, throbbing dick of his slid all the way up into my rectum, made me whimper with ecstasy as it plowed past my prostate gland. I felt a drop of precum force out and run down my dickshaft. As he slid in, Bill let out a deep protracted groan.
“Oh, you’re so tight, baby. You’re so tight!”
I turned my head to the left to look over my shoulder and thank him. With his cock buried in me he leaned forward and fastened his lips to mine, giving me a deep and lengthy French kiss as he fucked me. I moaned and whimpered and cried, rippling with pleasure at being impaled on this hunky convict’s monster dick.
Five minutes later, me gibbering in delight, he wrapped his hands around my waist, rolled back so his legs were under him, and suddenly I was sitting in his lap, all of his nine inches buried up in me as he fucked me deeply. Now we were both able to turn our heads and kiss even more deeply.
Somehow he managed to free up a hand to jack me off while I was still in his lap and getting pounded so lustfully. There was a steady flow down my shaft from all the prostate juice being squeezed out by his fucking. It coated Bill’s hand and made it even slipperier. I moaned uncontrollably into his mouth, knowing my orgasm was on the verge.
The feel of Bill’s spunk jetting deep in my rectum did the trick. I lowered my head and opened my mouth, hoping to catch a good blast of my own cum, hoping my new daddy would think it was real sexy. Most of it ended on my chin but I got to enjoy the taste of a little. He lay down on the bunk, spooning with me and holding my body to his, making me feel safer than I had in a long time.
I made up my mind I’d do anything for him!
A week later the honeymoon was over. I was just now finding out that one of my duties as Bill’s sissy wife was to “entertain” his closest buddies, all five of them—and all at the same time if they wanted, which they apparently did.
“But why, Daddy?” I moaned. My face was splattered with cum from giving each of them a blowjob, and now he wanted to see me get fucked by every one of them. I only wanted his big dick in my sissy ass, but I had no say in this.
“Because I’ll slap the shit out of you if you don’t, sissy bitch.”
A tear running down my face, I took position bent over with my feet spread wide apart and bracing my hands on the bottom mattress. I heard the sound of a condom wrapper opening—Daddy was clean and so he wouldn’t let anyone fuck me without protection. As his pal Chet asked for some lube I heard the staccato rap of guards’ boot heels drumming down the corridor.
I immediately sat on the mattress and wiped the cum off my face. I reached for my pants like I was putting them on, but I knew nobody would be fooled. Everyone knew about the many daddy-sissy relationships and the loaning out of sissy wives, but because these arrangements reduced violence the guards turned a blind eye to it. They did the same with uniforms. We sissies and the trannies got to modify our uniforms into halter tops, hot pants, even miniskirts, as long as we maintained one regulation set of clothes for state official’s tours and visiting day. Still, you didn’t fuck in front of the C.O.s, the guards.
Three guards including a sergeant came to a stop at our open cell door.
“Inmate M-11428,” barked the sergeant.
“Yes sir?” I asked, fumbling with my skintight denims.
“Captain Janus wants to see you.”
Gratefully I tugged on my denim jeans, humiliated that though I wasn’t really looking forward to the gangbang, my dick was still hard from my predicament. I saw out of the corner of my eye that Bill and his chums were scowling, but defying the guards, especially the captain herself, brought down shit on everybody. As I stood to leave I turned to my cellblock husband.
“Sorry, Daddy,” I said in the little-girl voice I knew he loved.
A reluctant grin broke through his scowl and he jerked his head toward the guards. “Don’t keep the captain waiting.”
As I followed the trio off the cellblock, I recalled briefly meeting Captain Janus during my intake. She was a fairly pretty and buff but shapely blonde in her mid-thirties who had a trace of a German accent. I heard rumors she was an immigrant from Berlin who’d been a citizen for many years, and who had a love of discipline and corporal punishment. When I heard that I thought she would have made a perfect professional dominant, accent and all.
The guards marched me up to an office door, knocked and took me in. A truly breathtaking redhead sat at a receptionist desk. She looked to be in her mid-twenties with hazel brown eyes, and her silky hair flowed over soft shoulders. It was then I noticed with a start she was wearing tailored state denim, an oversize work shirt that had been taken in so it clung to her hourglass figure.
“Is this 11428?” she asked in a voice far too beautiful and demure for this place.
“That’s right, Ange,” grinned the sergeant.
“That’s Angelica,” she scolded with a toss of her head. “You and your men can wait on the sofa or come back when she calls.” She looked me up and down with a smirk of recognition. “I don’t think this one’s going to cause us any trouble.” Then she picked up the phone. “Prisoner Minius is here, Ma’am… Yes, Ma’am.” She turned back to me. “You can go in now. That door over there.” Then she gave me a knowing grin. “By the way, there’s still a little cum under your chin.”
Blushing I rubbed it away and walked to the door. I held my breath and raised my hand to knock.
“She’s already expecting you. Just
You said you had a lot of content on the way and we have got pretty much nothing worth while so far
Can you do misty from black ops 2
I understand why you might need a break,, Shad. Thanks for the art, it’s great and I’m always looking forward to more of it from you. Take it easy chief.
Can you do a Loba piece plzzz
Can we get some action with Loba? She’s the newest character from apex legends and she’s the number one search result on pornhub but there isn’t any content on her yet so you could be the hero of the people
Do what you want shadman. We are all here to see you and what you can do.
Respect Shad brethren
Who else expecting the girl from ps5 demo to be on here
man belle nun is sooo fukin hot
sorry god
yeah i agree, except that pedo shit, thats fucked up
The people who go out of their way to attack people who criticize shad are losers. The guy has literally posted pedo porn on here, idc if he deleted it, it was still willingly posted by him and as far as that goes it kinda makes him immune to having sympathy from others just like the people who orgasmed to those pictures are too. And sorry for this catch-22 but if you reply positively or negatively you’re kinda proving my point.
Half of you stand on some fucked moral high ground yet you’re in the comments section of the most depraved Surface web website outside of efukt and heavy-R. Please shut up and look at the art and leave like a “normal” person on here.
The only thing I attack him for is when he dies for a really long time. I don’t know about the pedo stuff lol
You just broke your own “rule” about moral high ground, you dumbfuck.
I think I hear your daddy calling you for more butthole. Better not disappoint him.
back at it again huh dumb fuck still being a worthless troll begging people for attention
Never said anything about a rule but you got baited
Tl;dr don’t use comment section. K.
I diagnose you with autism.
im sorry for being mean to you i want is to rim you while Shadman breads me
And I’m secretly in love with DFE which is why I can’t resist replying to her and posing as her.
I just realized that when I copied her Gravatar just now I made errors in spelling (“breads”), capitalization (“im” and “i”) punctuation and sentence structure that DFE would never make. That’s because instead of paying attention in school I was busy watch pedo porn and giving blowjobs to the Mexican gardeners who worked at my skool.
You all replied to me :( retards baited
We’re all in quarantine what the hell else is he using all this time for! Fucking make something Shad!
shad you lazy fuck lmao “im gonna give u guys a lot of content” and he proceeds to make 1 shitty drawing with 3 crappy variations
kys entitled cunt
You mean 2 godly variations
Calm down son, it’s just a drawing
no we mean low effort variations, it’s like a YCH, it’s mainly already done
Super edgy, bro
“Super edgy bro” either redditors or women have taken over shadbase. Neither is ideal…
I would Love to see you do a Game of Thrones Chair but instead of Swords it’s just Guns and Knives
This comment section is actual garbage.There s only 2 types of people:those who demand more uploads like this guy s their fucking slave or some shit(who are probably underage teenagers desperate to bust their 15th load for today) and those who blindlessly defend him like he s the second coming of Christ,thinking you can’t criticise without being a hater.There s no in-between either
you could let me be in between your cheeks bro
no homo
You forgot the third kind: the spastic incels who attack the comment section itself… like you just did.
Now go fuck your mother some more; I hear she loves your little pinky-sized weenie.
Fuck off back to your klan meeting your worthless old cunt and fuck your dog like the used up whore you are.
And now we have officially gone full circle. Good job.
The replies to this are perfect btw
nice powerwolf quote there shad, looking forward to your next work, but make it at your own pace, dont let yourself be pressured by the other commentors
Are you fucking dead
draw something new you piece of shit
Fuck you dude it’s not all about porn
Stfu yes it is
It’s literally the only thing we’re here for.
Great work Shad! Fuck all these retards telling you to post more, you do you. I just appreciate that I’ve been able to enjoy your fantastic for over six years now, all without paying one cent.
Post something good this is shit
Everyone’s a critic
its fokin free
Bruh y’all are getting way too worked up over his posting schedual, like really ever heard the saying “you can’t rush art”
But have you heard the saying dont write a check your ass cant cash?
Ever heard of “ARTBLOCK”?
ellie the last of us 2
Why does shadman die at least once a month? What is this “dying” habit he’s developed? I don’t like it one bit. All in good fun lul. Plz post ass.
get a new job you slack way too hard
You say slack but if you look back a few months he’s doing a completely different style that’s more detailed personally find the wait worth it if he puts out stuff this detailed even if it’s not straight up porn it’s just better has a lot more work put in it
I love that face, I like the way you draw the faces and bodies they look so real
Bruh all I gotta say to this is…good job! I love the art and that’s what I always come back for; you never cease to amaze me with the different art types you draw and overall keep doing what you’re doing! You have no “schedule” and no rules to hold you back. Art is art and keep doing what you do best as long as you don’t represent kids actually fucking their moms and shit
If the only complaint here is “Give me more art, faster” I’d say shad’s in a pretty great place as an artist.
how do I upvote
rip shad
shad should totally make decals or stickers of his art
You should stick with posting nothing, it’s what you’re good at (and for).
NICE TRY, FUCKFACE. BUT SHAD CAN SEE IP ADDRESSES.
HE KNOWS YOU AREN’T ME. BORING LITTLE BABY YOU ARE.
You are such a cuck dude lmao get help
Is your cap locks broken? And why are you replying to literally everyone? Fucking looser
Y’all need to stop suckin Shad’s dick and understand that when you have a job, you gotta fuckin do it. Assuming most of you work, what happens if you don’t do or take to long to do what you’re being payed to do? you lose that job.
Shad should bring back JL, at least we would have stuff to look at while Shad’s on his month long heroin binges.
DRAWING IS SHAD’S HOBBY NOT HIS JOB, YOU STUPID MOTHERFUCKER.
IF YOU PAID MONEY TO ACCESS SHADBASE, ONLY THEN COULD YOU CALL IT A JOB.
IF YOU WEREN’T SO FUCKING STUPID YOU’D KNOW JLULLABY IS RETIRED.
If that’s how you usually reply to kids you’re probably a bit shit at reaching out to the youth.
So I understand drawing isn’t easy, but you constantly say you’re going to set up a consistent upload schedule, like I’m pretty sure you’ve said it 6 or 7 times over the past few years. Can you just stop saying that if you’re not actually going to? I’m like 90% sure that’s why everyone gets so angry when you just vanish like this.
Also before you guys shit on me like you do with everyone else, I realize he doesn’t owe us anything, but he’s still creating expectations when he says that and it’s reasonable to get annoyed when a literal month goes by and I open the site to the same set of cock and balls every day
I’M 100% CERTAIN YOU’RE RETARDED. EVEN WHEN SHAD POSTS REGULARLY, TROLLS (LIKE YOU) STILL SHIT HERE.
HERE’S A CLUE: THIS PLACE IS FREE. DRAWING IS SHAD’S >>>HOBBY<<< AND NOT HIS JOB. HE OWES ALL OF US NOTHING.
I find it amusing how you just completely disregarded the message he was trying to convey.
You’re literally retarded and ignored everything I said good job faggot, btw all caps makes you look like a sped
Hur dur someone criticized my god so I’m going to have a tantrum on a tranny fan art website
OP is exactly right. Shad is a little cry baby faggot that makes bullshit up so he can be a lazy piece of worthless shit.
Beep boop
Leave the man alone at least he draws for us hell it doesn’t fuckin matter how long he takes at least he’s drawing for us
Draw you lazy fuck! You have ONE job.
shut your fuckin gob you sweaty cunt hes got other shit in his life just like you go beat your tiny fucking cock to other shit while shad does his thing
Amen
HOW DO YOU KNOW SO MUCH ABOUT SHAD’S LIFE AND HIS WORK?
HERE’S A CLUE, YOU DUMB FUCKING MORON: YOU KNOW NOTHING.
Lmao this guy is dickriding shad harder than anyone I have ever seen. Lmfao.
Keep riding his dick. It doesn’t matter that he’s lied about uploading 2X a week for all of 2020
Bish neither do you
can you draw mewtwo again that shit was hot
Yeee
Please make some more straight porn, I don’t have anything against gay/lesbian porn, it’s just that I’m not into that kind of thing. throw my meat a bone shad ;~;
Nah I have something against em alright. I hate em cos they breathe. Fucking faggots dare think they can take up time that would otherwise be allotted to my interests. That would normally be acceptable, but it’s faggots were talking about so its an extra layer of grievance
Need doja cat
Shad, i suggest you check out android 21(from dragonball fighterz). I believe you’ll have alot of ideas of her
yoo my guy
this nigga really be makin mediocre content and expects us to be grateful
Mediocre my ass brush it’s not like you are a professional artist and can judge him on his drawings so yeah be grateful pussy ass bitch
his art is very mediocre retard if not below average
i agree, i miss his old artstyle
I appreciate it man, my effort is definately there, but Im really not satisfied with my delivery speed, Ive become more fixated and self conscious on certain details where its never good enough and by attempting to fix it it over and over again I sometimes make it worse, if I can figure out a way to cut down on that process I could put stuff out at a much quicker pace, its hard to describe the feeling of seeing things differently depending on your brain chemistry at the time and how long you have been looking at something. By trying to make everything seem more alive and life like, the more it starts to reveal all of its flaws.
-Shadman
For anyone who is curious as to why it takes him a bit longer for new art and might have missed this in the comments. (He was responding to a guy who was complimenting the this nun)
Come on man
i’M gOiNg To StArT pOsTiNg TwIcE a WeEk
Bro takes 9 days to draw a picture nigga why you doing
Don’t mind me, I’m still waiting for that mother’s day post……
I can Fuxk her for Infinity.
Lobaaaa de apeeeex. El mundo lo reclamaaaaaa……. pero cuando puedas xd
Request: Can you by any chance do one on Loba from Apex she is just super thicc and I never see much R34 apex legends stuff that often and would love if you could provide some.
Si amigo totalmente de acuerdo no soy fan de apex pero realmente ese personaje es ideal esta buenarda.
Can u do some art for misty in call of duty black ops 2?
Hey can u do misty from black ops 2
Where’s the muslim at?
Needs more hijabi…
Needs more muslim…
I love your art and I’m wondering if you could make some from Paladins.
Preferably Maeve.
LOBA!!! PLEASE LORD SHAD
He died from corona(
Yea probably
i know this has prolly been said before but,
shad-*bea*
Shad do a James Charles one
I really like the ass on this one, it’s hard to explain but it feels more solid and natural than the basketball butts you used to draw
god i love this as a possiblwe poste rfor future prints, but i wish she was smoking a long 120 menthol. so badass.
LOBA from Apex Legends
PLS makes It!
We Need LOBA porn from Apex Legends
Siiiiiiiii
Send your dick to RSFM23 on kik to get an ass pic. All dicks are welcome (pussys too)
If anyone tries this out, tell me the results pls
shadman made a mistake in the second picture. the nipple shadow is visible dispite her nipple being covered.
No he didn’t
Dude’s right, I’m sorry
Stop taking so long to upload
Do this but with the new bitch from apex
Agreed MAKE LOBA
Amen
No Raven’s mom for Mother’s Day? Would have been glorious.
Shad fix the shadows in the second picture because the nipple still visible
No it’s not u dumb
lol yes pls
You should draw Loba from Apex Legends as she is thicccc. Love your art
Return to the Marco Diaz comic
Ied tap that 💀
Where are the balls? I need to see a lady’s cock and balls.
Agreed
You have autism
That be a guy not no female
In denial faggots be like: “Yeah I want that girl right there. She’s so fine! With those big hairy arms and that giant cock”
Mothers day?
Nun delphine. Tought you changed the faces or is it intentional this time ?
Instead of telling us you hope to get multiple posts done in a set period of time, how about you reasonably set expectations like “I’ll try to do one piece of art per week” so we don’t feel let down when updates take forever
You mean the free high quality art? This stuff takes time. He dosen’t owe us shit though
I’ve never seen a retard as stupid as you. Kill yourself for simping over a porn artist, you pathetic cunt
Yeah I’d also prefer less art with a set schedule over more put out sporadically, but that’s just the way Shad has always been and (probably) always will be. I think he’s just too dedicated to making things perfect that he can’t consistently get out work w/ out being disappointed in himself (we all love your work Shad, there’s no need to worry!).
No penis equals bad
Do somd fucking porn already you lazy piece of shit !!!
Be patient dude, jeez.
Its his own fucking site he Will do whatever he fucking wants
Its his own fucking website scrub, he Will do whatever he feels like to
Text me on kik: Meltygummy
I’m a 19 year old sub femboy that needs a cock to worship and send nudes to
Hey ShadBro! Nice Nun dude!
Soooo…. are you planning to finish “Plain Ol’ Wife”?
Two years man…
Wrong guy. Plain Ol Wife was Jlullaby’s work and for some reason he quit. If you REALLY want it completed go commission that hary96/harydraws guy to make an ending. He kind of took over a lot of JL’s projects. Does nice art too, all without being a chickenshit like some people.
Shut up LaPedofag, no one cares what you have to say, you baby raping piece of shit. Cure the world of your existence, drink bleach.
Shut up already you fucking reddit faggot
Who are you again?
Something new when?
No Mother’s Day post ? Disappointing
id love to see a dildo/buttplug held in place by her thong.
facts. but shad is trash now and only draw boring shit he wont give her a butt plug or anything. JUST boring trash = shad lmao
We need a few Loba drawings bro
Draw some cock and ball torture.
Draw some cock and ball torture.
Draw some cock and ball torture.
Draw some cock and ball torture.
Draw some cock and ball torture.
Draw some cock and ball torture.
trap version when?
fuck off faggot
fuck off bigot
Homo
READING THESE COMMENTS MAKES ME THINK COVID19 WIPING OUT 50% OF THE WORLD WOULDN’T BE BAD
yeah including a soyboy apologist like yourself.
Sinning with your naked bod is evil and bad
Shad I would on god buy this if you make it a pinup. I love all your work porn and nonporn alike and I think its dumb that people give you shit for your hardworking. I appreciate you man. 👍
Raise your bone up to the sky!
FUCK YOU SHADMAN, YOU LAZY FAGGOT !!!!!!!
edgy as a pig turd but even less pleasant to be around
How is a big turn pleasant? Did you think your reply was badass or something? 💀
lmfso posted @ 7:38 and replied at 7:39
this retard’s replying to himself
It’s cool, you do really cool pin up style girls
loba content pls
‘Im gonna try to get a couple more out this week since i missed last week’ *proceeds to not post for a week*
He said try if you’re gonna quote something he said, read it right
Discord: Corsa#5275
Thanks for putting so much time into your work! It really is admirable, also love the shading on the second pic!
Anyone wanna cum for me My snap is travishoppe2020
This is definitely poster material
One would think that during the lockdown you will upload more, not less :|
But also upload a shitty non-porn pinups
BECAUSE OF COURSE YOU HAVE 100% INSIGHT INTO SHAD’S PRIVATE LIFE
No, I don’t have 100% insight into Shad’s life. My comment didn’t imply that. If you don’t understand the implications of one simple sentence, I really pity you.
I prefer the darker one
Shadman should add a community section to his site
you going to pay for a site designer to add it for him?
the last thing he needs is to encourage more trolls
I’d bury my face in that
omg yes
Yes
Ok this style but with Mewtwo
Clappinglights2 on kik hmu for bbc
Can you make some cyberpunk 77 things
YES but not until after the game is out
SHADBASE HAS BECOME SO TRASH PROBABLY THAT SPAZKID MF BRAINWASHED HIM
I agree lol
its fuckwits like u who make it trash
Gotta disagree. I give that to the faggot jews
we broke a new record! THE MOST OFFENSIVE WRONG PERSON.
another “edgy” teenage incel taking out his virgin frustration
heres a clue, junior, you have ZERO chance of ever getting laid
(molesting your baby sister doesn’t count as that, sorry to tell u)
and deep down you know that which is why you’re a lame-ass troll
Jokes on you, you haven’t a single fucking clue about my life and what I have and haven’t done. But please, by all means, continue wasting time and energy on incorrectly painting a canvas about the life of an anonymous user in a pornography comment section
new poster maybe
SHAD is DEAD DDDD’:
That’s what your dad used to say about your mom because she used to just lay there with her eyes closed. (Mom was fantasizing about BBCs.)
Bruh i’m Black
You’re so pathetic dumbfuckkk, you keep changing your name but you always use the same sad old insults, you’re such a sad, old racist loser.
There are so many cartoons, comics, etc, that haven’t been touched by your magic pen yet. Just out the top of my head I can think of Hot Wheels Battle Force 5, Total Drama, Futurama (although I can see Bender on the right there ->). These 3 cartoons have a lot of characters to work with.
Total Drama Island would be perfect for this site
do gamoraa
Just wanna say that your work is incredible. You are a very very talented. Take care
Man, as much as I enjoy your art and appreciate the time you take on all this, having an update every like 8 days after you promise multiple weekly uploads is just frustrating. I didn’t visit this site for about 3 months and I saw about 12 new images. That’s ridiculous
Imagine complaining about not getting FREE porn, lmao.
You sound like such a fucking worthless bimbo
Hihi
Alter Shad, richtig geiler Scheiß pass auf das du dich nicht komplett verausgabst.
Noone gives a shit shad! We just here for the porn
Girls with braces ang big asses are hot any color
Do Billie eilish
Where’d the other one go?
Such a shame only degenerates visit this site.. This guy has great skill and unique style
Ummmmm, you’re here…
Shad is the biggest degenerate of all TF r u talking about? Are you new to this site?
Dude check out Ellie Leen!
Ive always liked the mix of cartoony and realistic
no 2 is more my style i like the use of the darker red also the bits on the arms and legs go very well with the skin tone
Amazing
Kim Yo-Jong
When did shad change his twitter pic, i’m just realizing it now
RAVEN
Make a ruby gloom comic next
Yo ahad ik you prob wont see this but can you make a comic of this girl i REALLY wanna smash. Her insta is welp_2005. Thnx!
…shes 14, shad doesn’t do loli anymore because he isn’t really into children
She’s 14…
She accepted it
Fucking elijah
Bitch thinks shes depressed.
Then go and talk to her you fuckin incel fag, stop jacking off to anime and make a move you cuck, also shes literally 14, how useless of a human being are you to be horny enough to try and ask somebody to make a shitty lol hentaii of her
Bro if you wanna fuck a 14 year old at least find a better looking one.
peepee
Doms hmu on Kik JGsub
more chastity cage please
I know nobody will read this, but I prefer your older posts simply because you are way overdoing the details and end up with some really weird looking anatomy as a result. Part of that is that you try to go for realistic proportions and a cartoony style all at once which just doesnt work imo. Another thing that plenty of people already said is that you never finish what you started, so thats always disappointing.
if you really believe his proportions are off and “really weird looking” then go draw some better art, fucknut. shad has been doing nothing but improving his art and he literally STUDIES anatomy and muscles to implement that knowledge into his work. shut the fuck up lol
im with you one that one
NOBODY CARES WHAT YOU PREFER
Fucking whiteknights
ok so he does do futa and no it is not gay it is still a frmale and you are attracted to the females body its just a fetish it doesnt mean you want it the same from a man. so stfu
Shut up gay jew
Pathetic faggot
No Mother’s Day post? This makes me sad.
Let me guess… Her name’s Eda?
Happy mother’s day! I wish my mom was getting her fat ass fucked by a thick black dick while my faggot ass watched :)
is that a powerwolf referance
Nope. Great band although…
yup resurrection by erection if im not mistaken
if u want to trade pics with a big Dick add me on kik: MoshiMoshiM8
Only Women/Cute Traps
I thought he’d post more on quarantine. Guess not. Whatever happened to the raven starfire art he was going to finish?
it is finished you’re just in denial that it’s over
Less of these soon, hopefully :)