Freedom from all of the scars and the sins, lest we drown in the darkness within.
I blame the tattoos that I havent gotten a lick of sleep yet this weekend. I might make more with the prison girl so I have an excuse to use them again.
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She is very tall
the fucking detail you put into these man. it’s amazing
The last one is kinda cringy but fuck that
Really outchea blessing my lesbian ass and many more
femboy that needs to be used
Kik: Gothtrap800
discord: femboy#4911
Ah dumb nigger
mark
1
I just noticed zuckerburg…
When Shad’s not drawing dicks and butts, he makes one hell of a tattoo artist
Would love to see a comic where the guard fucks the shit out of the bitch in the jumpsuit.
Wait am i the only one who saw The ZUCC man on the background?
HE CAME ALIVE THIS IS TRULY A CHRISTMAS MIRACLE
Wait the first id says 5’11 then the zoomed in one says 6’11?
Since the 5′ 11 one also lists “Sex: Yes” I think the zoomed in one would be considered the “canon” one i guess.
Love the sex:yes on the Id lol
Necesito más de esto. (?)
6’11”? Hell yea she TALL!
She looks like Volskaya’s daughter
The girl with the jacket kinda gives me a Undertale vibe and it scares me
Actually I have to agree.
Oi😍😍😍
MARK IN THE BACKGROUND I CANT ANYMORE AAAAAGAHHHHHH
what the Fuck was Zucc doing there
Hey! I’m still looking for people to do an rp with xD
Add me on kik, and you can ask for my discord there!
Kik: _X30N_
fuck off…
51
Holy shit 6″11″, that’s a tall woman right there, thats taller than me, a foot taller
machinehead lyrics, zuckerberg in the background… creative.
Freedom from all of the scars and the sins lest we drown in the darkness within.Never thought I see a machinehead reference here.
Y did prison girls eyes turn brown in the last panel even tho they were blue in all the rest?
This is Shad, got logged out, couldn’t decide if I wanted to change the eye color so I did on the last panel, didn’t think anyone would notice. Brownie points +1
Yeah extra brownie pounts
Can we have more of that jacket girl
Love it continue with these 2 ladies strapon fucking (girls only)
Why does she have to be gay?
wow awsome one right here I want to see more of this. XD
Hey dude your a great artist and i loved thicc women.
Cmon Shad plz make another story like the crossdressing boy one!
This guy’s got the right idea!
Also once the prison guard catches it, he could chain up and cock cage the femboy and fuck her right infront of her girlfriend.
Bruh Mark Zuckerberg hahaha
Glad someone else caught that too. XD
What the fuck is the inmates name? Her signature is so shit I can’t even make out the first letter.
Zuck in da bacc vibin
Less women and more cock
Um that’s kinda gay dude
No, more women, and no cock
For 6 “11, isnt she like super underweight at 195 lbs?
So glad to see I’m not the only one who noticed that 😂😂
No Slightly underweight at least when you put into a BMI calculator.
This is the best work and the best character you’ve done in a while, imo. Would love to see more of the inmate, maybe after she gets out. But honestly, I wish I could double team a girl with her.
This website dropped in quality
Fuck off retard
WRONG
https://www.youtube.com/watch?v=McAeQiLmEYU
FUCK YEAH
Why does she have brown eyes in the last picture. Didn’t she have blue eyes.
21 year old boy looking for friends :) add me on snap: rexerax
exchange nudes with women, traps add kik alef567 i will send pictures of my dick
I’m an 19 bi male who likes most things on shadbase. I have a nice feminine butt if you’re curious. Ignore the fake negative comments that look like they’re different people, there’s a no life loser who leaves edgy comments like they’re from different people. since it is all anonymous. My kik is bottomcream. I like male female femboys trans, add me and see this butt for yourself 😊
nice butt big enough
Went from 5’11 to 6’11 damn
I just focused on Mark in the background
more of this yes please
the zuck
Love your work shad
Traps/Fembois and girls wanting to rp/pics/vids, hmu!
Im kinda young but i dont mind if older guys in Huston tx hmu on my Instagram which is melanie_ann143_ and my snap which is melanie_ann143
Or hit up my friend she’s legal. Her snap pikachu_kara or on her IG _.flightless_butterfly._
Hey boys and girls, I’m looking for someone in the Boston area to free me from virginity. I’m a 15 y/o pan boi so kik me at GlacierPlayZ. I take all genders.
She lowkey looks like Ruby (RWBY) looking back at this
Is no one gonna talk about what Zuckerberg is up to?
政治不正确
Young M with nice ass
Kik
IronBoi99
6 foot 11? 😳
6’11? 😳
Love a bit of machine head
Give her dick please
Go te fuck to sleep shad
Loved the work on those tattoos! Would love to see more of the prison lady!
Question: Is there any chance we’ll see more horse/beast content in the future?
no
I’ll have to double on that one
If a centaur had a dick, where would it have it?
At some point, this is quite sweet actually … (especially that ass)
I do prefer comics with dialogue, but this is nice nonetheless.
My hope is that you’ll make another upload but with some sultry dom/sub play texts. That would be lovely Shad <3
How is she 6’11 and that thick at 195 pounds that makes no sense
Helium
Is this a Blink-182 “Feeling This” reference?
Give her a dick pls
please more of thissssss
I’m an 19 bi male who likes most things on shadbase. I have a nice feminine butt if you’re curious. Ignore the fake negative comments that look like they’re different people, there’s a no life loser who leaves edgy comments like they’re from different people. since it is all anonymous. My kik is bottomcream. I like male female femboys trans, add me and see this butt for yourself 😊
not 19 not his pic desperate
So we all here are just gonna ignore the small Mark Zuckerberg?
Ikr
Is that Mark Zuckerberg?
Please more with that brunette.
https://www.instagram.com/p/B8ORUFPHAhc/?igshid=3m7sszmj8c0n
NEW CARTOON MILF ALERT
WARNING! SCAMMER ALERT! WARNING!
THE SLAVIC SCAMMER WHO POSTS AS “Alissa”, “Alisse”, “Kikki”, “Alisher”, “Bobby” and a dozen other fake names, a “Anonymos” IS A RUSSIAN SCAMMER WHO WANTS TO STEAL YOUR FINANCIAL INFORMATION
DO NOT EVER CLICK ANY FUBARS.PW DOMAIN LINK
Facts about fubars.pw
Company data
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FUCK YOU, RUSSIAN CRIMINAL. LEAVE SHADBASE. WE WILL NEVER STOP WARNING EVERYONE HERE ABOUT YOUR PHISHING WEBSITES.
Woooow! Soo cool girls:
fubars.pw/video-8491
I like it!
Really wow!
Source?
Name?
THIS IS THE RUSSIAN CRIMINAL’S SOCKPUPPET, NOT ‘Anonymous.’
HE LIKES TO COPY-PASTE OTHER PEOPLE’S POSTS TO MAKE
HIS PHISHING LINKS STAND OUT – DO NOT BE FOOLED!
WARNING – FUBARS.PW IS A RUSSIAN SCAMMER WHO
WANTS TO 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.
You never finished the Daphne and Velma comic
The girls outside the glass looks like Joey Wheelers(?) sister from Yu-Gi-Oh
Just a silly remark but I LOOOVE the inmate’s hairstyle! And how those loose strands of hair get out of control more the further the comic progresses.
Did anyone else see zucc in the background?
Can you follow up with this?
Love the tattoos on the red head.
Yo am I the only one that noticed that she’s 6’11
Shark boy and lava girl pages please lots of 🍑 play and 👣. Would be great to see
Would it be weird to say that I actually look almost the same as that prisoner lady? The only differences are that i don’t have tattoos and my hair is lighter.
I’d like to see that honestly.
I’d love to see that honestly
I’d like to see that if you had a dick honestly.
I’d like to see that honestly
Post or gtfo
I really enjoyed this, you do you. Don’t worry about haters, I know you won’t.
Dude what is wrong in your brain, when people liked that nerdy scooby doo character (sorry forgot name) you just stop doing it completely, same with the starfire heat comic. And when you do something that people don’t like you keep doing the same stuff over and over again. Really like your style but listen to your audience it’s not hard.
Damn i just love it when you just fucking stop doing what the stuff that people like to just make generic shit that no one wants to see its really funny keep it up
Shut the fuck up and let him do what he wants, bitch. Acting like he owes you shit lmfao get the FUCK out.
Send me pics Guys or Girls im a guy willing to trade or send
Kik-Eljamesboi
Kik me pics Eljamesboi i’m a guy will trade looking for guy or girl pics
Damn, this is some hi quality stuff
Don’t forget about the next panel for Starfire in heat
Yes please
I always love when you add tattoos onto your characters. Very well done.
I’m here to stan lil Thicc Zucc, more of him!
Shut the fuck up you annoying ass “Stan”, seriously you guys are poisoning the internet.
Anonymous looked at shadbase, his hand firmly grasping his 4 inch dick instead of jerking off his disappointingly small dick for a tiny spurt of infertile semen, he decided to scroll past the featured porn and dive into the comment section. There, he saw a myriad of horny people asking for nudes, random requests for characters for Shadman to draw and autistic edgelords. None of these caught his attention until he happened upon a comment which made his erect, 4 inch dick shrivel back to 2 inches. The comment contained the word “stan” which greatly disturbed the little snowflake. His veins popped out on his forehead, his teeth began to grind and he began frothing at the mouth. He was so furious that he almost cried but didn’t because he was not a sissy even though the word “stan” hurt him a little every time he read it. It was HIS internet and the “stans” were ruining it for him and he was going to inact change. Yes, he was going to become an activist. He then plied his hands off of his dick and began to spread awareness that stans were not welcome here. He typed that they were ruining the internet. He smiled, proud of his achievement. He had ended all the “stans” by leaving a comment on shadbase. He then scrolled up, clicked on archives and went straight into the traps section to begin abusing his now hardened cock like no tomorrow.
holy shit dude this is gold
Ok, This is epic
Zuckerberg in the background just going about his everyday life, watching people from afar without them knowing
Dame, what a thick looking prisoner!!!!!
You should do a breath of the wild style Zelda post
Traps and fems
Kik me: TristanDugrayy3
Snap me: TristanDugrayy
Shad would love Dorohedoro
Thanks for the recommendation my lad
Is the inmate shitting in her hands in the last picture
Using the phone as a dildo
THAT’S A PHONE DAWG
I need a woman like this! Looking for a woman to start a long term relationship. Must be 21+ and live in or near worcester. Message Dalek333 on kik if your interested. It may take a while for me to reply. I’m lonely Xb
And neither of them has a dick? On Shadbase? This is all very scary and confusing.
I love the prison girl, hope she appears more often
Yo, love that Superjail! reference on the prisoner ID. Always thought Jackknive was a badass name
I can’t be the only one who thinks that the name on the ID is a reference to Jack from Mass Effect 2, right? Because if that is the case, this is my favorite thing.
Wtf is happening to the wanted sight in the background
Zuckerberg do be kinda thicc doe
The scar on her right buttock is missing in some frames.
Your on a roll Shad.
Yo can I request more of the prisoner? She is hot!
I love prison girl. I love her so much. I want more I need more
I love the tiny jucc in every frame
my gods the tattoo work and the way it stretches but still looks so good and accurate to the ones above it… Shad you glorious bastard. Now finish the raven and starfire comics! q.q
why tf is the girl on the other side of the window so cute
Heyyy horny boys and girls😙👅💦💦, i lost my old kik “someonesslut7” so u should cum visit my new one, someonesslut8 for whatever you wanna see, i hope i can find people i talked to before
reported someonesslut8 to Kik for illegal porn
Undeertale
Heyyy horny boys and girls, i lost my old kik “someonesslut7” so u should cum visit my new one, someonesslut8 for whatever you wanna see, i hope i can find people i talked to before
Heyyy horny boys and girls, i lost my old kik “someonesslut7” so u should cum visit my new one, someonesslut8 for whatever you wanna see, i hope i can find people i talked to before
r6
Soo cool girl:
fubars.pw/video4812
Yeeea!
WARNING – FUBARS.PW IS A RUSSIAN SCAMMER WHO
WANTS TO 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.
do spider gwen
DEGAN
This was really sweet you sick fuck
Lol i see mark
I exchange nudes with women, traps add kik alef567 I will send pictures of my cock
holy shit mark is so thicc
she’s schizophrenic which explains the officers not reacting to the sexual stuff going on
Dude the the scar is on the wrong side of the face.
This makes me happy
The fat guy with a moustache is kind of cute.
Shad I love the use of that phone. And all the details on this strip in particular, you’re really improving.
This is the Shad I love ;)
Any chances of seeing some more bestiality? You draw the best ;D
Keep up the good work my man and look after yourself.
Didn’t care for the porn, too busy laughing at Zuckerberg
Thought I was the only one lol
Shoutout to Machine Heads song, Darkness within.
Did anyone else notice the patch on the guard’s uniform?
Hey guys I’m an inbred piece of shit who likes beastiality. hmu
Prison gal is great! I’d love to see more of her
Vilma x daphne 3!!!
THICC ZUCCHINI strikes
I like the zucc
shad did you notice youre drawing way too many high res features on your higher ludy portraits/comics, usually youre saving those for pictures you can put up for sale easily.
i wanna see more inmate
please make a full pin up of the inmate
This is it
Traps and Girls, Submissives looking for fun kik me! PICS/VIDS/RP
Makes Nier Automata
Love how Zucc just gets up.
-long wang that had been buried all the way up her ass only minutes ago. Now she was finishing off Officer Garrett, and by the ecstatic expression on his face she was milking his dick with her asshole. I decided right then and there I wanted her to teach me everything: how to suck a dick that big, to have control over my ass muscles, to be able to actually do ass-to-mouth and not get all queasy.
Shortly after the CO blew his load up my tranny lover’s ass. He pulled it out, but when Rita turned around to suck it clean the warden stopped her. She told Officer Garrett to get on his feet and to face me. A hollow feeling filled the pit of my stomach because I had a strong feeling what she was about to order me to do.
“Clean off his dick, Petra,” the warden commanded.
“N-no!” I blurted.
I said it with barely a whisper but she heard. In four long strides she stood before me. “On your knees, prisoner Hartmann.”
I dropped as fast as if someone had kicked my legs out. My knees stung as they hit the carpeted floor. I was afraid to look into her face. My balls tingled with fear. Gooseflesh covered my body.
“I don’t believe I heard you correctly,” she said icily.
“I made a mistake!” I cried. “I’m sorry! I’m sorry!” I stared at the carpet.
“May I speak, Mistress?” Rita asked urgently.
“Speak!” the warden barked. I could tell she was still looking down at me.
“She’s young and scared and never been in any situation like this. I promise to teach Petra her place. Please be lenient with her.”
Gratitude filled my heart and I fell a little more in love with her right then.
“Look at me, Petra,” Warden Fordham ordered.
I timidly raised my gaze to see her glaring down at me before she looked over to Rita, her expression softening.
“That’s very sweet of you, Rita. Considering how you’ve already more than proven your worth, I might otherwise be willing to consider your request. However I think you’re a smart enough girl to know why I can’t allow you to teach this fishie her place. Can you tell me why?”
“Because it’s your job, Mistress.”
“Rita,” the warden said with a smile, “that’s three times today you’ve pleased me, so I will be a little bit more lenient than I was planning.” She looked back at me. “I gave you an order, Petra. Go suck his cock.”
I knelt in front of Officer Garrett. His dick was still hard. It glistened with lube and cum. Fortunately, it didn’t look dirty but it still smelled faintly of ass. I looked past him and into Rita’s eyes and saw her looking back at me so tenderly it was easy to imagine she did love me, which made what I was about to do so much easier.
I gave the CO’s cock a long lick. It tasted earthy and pungent, a little sharp. It was the taste from deep up inside my darling Rita. Suddenly that very thought turned me on like I never imagined it could, but only because it was the taste of her ass. Before I could think a moment longer I lowered my mouth onto his dick and began sucking greedily like a little kid with a popsicle on a hot day.
If it wasn’t Rita’s ass—my only true love in the world—I’d have been repulsed. Then I realized this would be a way to show her how much I loved her. I sucked and sucked and made mewling sounds of pleasure. After two minutes the warden ordered me to stop.
“You love the taste of Rita, don’t you?”
“Yes, Mistress!” I enthused. “I love everything about her.”
“You want to be just like her, don’t you?”
“Yes, Mistress!”
“Then you must be properly trained. Officer Hayes and Captain Grover, get the horse and bring it here.”
For a few seconds I imagined them bringing in an actual horse but the two guards went into one of the doors on the wall, which turned out to be walk-in closets. They brought out a big sawhorse-type piece of furniture with a wide padded top and legs. Each of the four legs had thick eyehooks set into them with padded leather cuffs attached to each with a rope that tied off at the bottom of the leg.
“Andie, bring the tarp,” she commanded.
One minute later our shemale guide had spread a ten-by-ten waterproof tarp. The guards set the horse in the middle of the tarp. Hayes looked me up and down and shortened the length of the top with some levers and locked it into place. All of a sudden I was frightened, realizing I was to be tied down, completely helpless. The tarp made me even more nervous.
Following the warden’s orders I lay across the top and draped my arms down the front legs. My chin rested perfectly on the far end of the horse. My legs were spread wide and cuffs attached at ankles; then the ropes were pulled until my legs were tied fully to the back legs of the bondage horse. The same was done with my arms down the front legs. I could barely move a muscle and I was fully exposed: my balls, my spread asscheeks and my mouth. My dick was trapped under my body between my tummy and the horse’s padded top.
“Mistress?” Rita asked. “Another question please?”
She looked at my lover with a charitable smile. “Let me guess: you want to be with her during her chastisement. Hold her hand and look into her eyes. Was that it?”
“My Mistress knows her girl so well,” Rita replied. It seemed to me that she was following some kind of ritual or etiquette that had to do with all this bondage and dominance and stuff.
“Again, very kind of you, but she must face her first discipline all alone. She can’t learn her lesson if it is shared. I will permit you to comfort her afterward.”
Mistress Fordham had circled behind me as she spoke. Out of nowhere came a cruel whistle of air as she swung the cane. The sound it made on my skin was oddly quiet, like a soft thud, but then my asscheeks felt scorched, like a red-hot poker had been pulled out of a fire and laid across my ass. I screamed. If I had not been tied down tightly to the “horse” I would have not been able to help jumping up.
Electric shocks fired down my legs and up my spine. What just happened to me was only beginning to register when that terrifying cut through the air repeated, and a new burning line crossed my ass. I was dizzy from the enormity of the pain. Another fell. And another. And another. The stripes of agony all added up to make me dizzy and weak. And yet my cock still tingled, halfway erect.
Without warning I felt warmness, a wet warmness under my stomach. I realized why the tarp had been put onto the floor: I had just pissed myself. In between the violent parting of the air and the blows I heard my pee dripping onto the rubberized canvas. The warden must have heard it too because she stopped beating me and tossed the cane onto her desk. She crouched down and looked into my eyes.
“Do you now grasp what punishment is? The consequences of disobedience?”
“Yes, Mistress,” I sobbed, half in pain and half in relief it might be over.
“Now grasp this: I was holding back seventy-five percent of what I can dish out. I can break your skin with that cane; I can open your asscheeks up so badly the liquid trickling down your legs will be your own blood.” She turned her back, walked to the edge of her desk and sat. “Rita, you may comfort her now.”
Naked and sweaty, Rita knelt in front of me and took my bound hands in hers. She looked into my eyes and whispered it was all going to be okay. She started planting soft kisses. In between those kisses she assured me I’d never have to feel that again as long as I obeyed without question, as long as I strove to please my owners and those I served, and as long I always kept getting better at being a sissy and a whore.
“Okay, that’s enough. Get out of there, Rita. It’s time to see if she’s even one tenth as good as you at sucking and fucking.” She looked to the trustee. “Andie, you’ve been such a good girl this week.”
“Thank you, Ma’am,” the stunning brunette said with a curtsy.
“Why don’t you be the first of our happy home to sample the girl’s cocksucking?”
“Shall a girl disrobe completely, Ma’am?” Andie asked.
“By all means. Let everyone enjoy your sexy body.”
The trustee kicked off her loafers, revealing some kind of hosiery beneath her institutional uniform. In a slow and deliberate striptease, Andie removed her prisoner top to reveal an expensive, lacy demi bra that thrust large C-cup tits with big, erect nipples out for all to see. Then came off her denims to reveal a matching garter belt and sheer, tan stockings. A big cock bulged at her lacy, French-cut panties. With sparkling brown eyes she looked hungrily at me. She sashayed up to me where I was still tied down to the horse; my mouth was level with her crotch. She was so very beautiful—every bit as much as darling Rita.
“You’re such a pretty sissy,” she said. “Eighteen and already so very feminine.” She eased down her panties a couple inches and freed up a cock maybe nine inches long and getting harder by the moment. “Suck it, baby.”
Eagerly I closed my mouth around her tranny boner, not caring how slutty my hungry slurping noises made me sound. I loved the feel of her firm, tanned dickflesh between my lips, pulsating in my mouth, the hot plump head sliding in and out. I strained to move my head forward, to try to take her into the back of my throat.
“It looks like she’s trying to deepthroat me, Ma’am,” Andie said. “She has true potential indeed… Do you think you should tell her?”
The warden chuckled darkly. “I think it would put her even more in the proper frame of mind.” I sensed the warden moving next to me, felt her hand softly stroking my ass she’d so severely whipped. “It was no accident you were arrested in that porno shop. It’s one of a dozen such places our… associates have under surveillance. For the most part they’re conducting their normal vice operations, but certain members, such as that sergeant you knew as Pat, are always on the lookout for us. They’re looking out for sissies like you who have the potential to become shemales like Rita or our lovely Andie you’re so eagerly giving a blowjob to. Pat waited for you to do what you know you wanted to, she made up a few additional charges to ensure you got into the state prison system. Another associate got you sent here.”
A deep hollow feeling opened up inside me as she described how I’d been set up, actually chosen for this place. Pat must have had her eye on me for months, assessing me. I had been all but kidnapped and brought here to be a whore for the warden and everyone who worked for her. From what she said, I was also brought here to become a shemale.
The shocking thing was how excited I was by my growing sense of helplessness. I loved the feel of my new owner possessively, fondly stroked the bottom she just beat. The notion of being enslaved as a sissy gave me a hard-on that ached deeply. I moaned over and over while I sucked Andie’s huge clit. Almost as if she understood my feelings I felt the warden’s hand reached between the piss-soaked horse and my tummy and feel my cock. She laughed with delight.
“You’re hard as a rock at your predicament,” she said smugly, wiping her hand dry on my back. “You’re home and you don’t even know it yet. Officer Lewis, welcome our newest sissy to her new home.”
I heard the rasp of a zipper and the squish of lubricant. A thick slippery finger coated my asshole and easily pushed up inside. I moaned again. Then a big dick plowed up my asshole. Soon Andie and the CO found a rhythm, taking turns burying their cocks all the way into my mouth and asshole.
“Switch!” the warden called several minutes later.
Without hesitation I sucked the dick fresh from my asshole while Andie’s nine-inch cock starting fucking deep up inside my ass. The dominatrix warden got me more and more excited as she described how I would be fully transitioned into a shemale.
“That it… if you really want to be,” she concluded.
“Mmmm-hmmm! Mmmm-hmmm!” I whined in lust, meaning it with all my heart.
I was a nasty, dirty slut and I was glad!
The third time Andie went into my mouth she blew a deep glut of thick, tangy cum all over my tongue and teeth. Gently fucking my mouth with her softening boner, she gave me a kind smile and caressed my face. “You’re going to love it here,” she assured me. “I can tell.”
Then CO Lewis stuck his cock into my face and I dove on it happily, Andie’s words tantalizing my brain. I he
shemale, a true force in and of herself when she was having sex. Even something I thought of as degrading as ass-to-mouth she made it look beautiful and wholesome. I wanted to be her so much!
Her plump red lips glistened with the black man’s cum—a foot-long wang that had been buried all the way up her ass only minutes ago. Now she was finishing off Officer Garrett, and by the ecstatic expression on his face she was milking his dick with her asshole. I decided right then and there I wanted her to teach me everything: how to suck a dick that big, to have control over my ass muscles, to be able to actually do ass-to-mouth and not get all queasy.
Shortly after the CO blew his load up my tranny lover’s ass. He pulled it out, but when Rita turned around to suck it clean the warden stopped her. She told Officer Garrett to get on his feet and to face me. A hollow feeling filled the pit of my stomach because I had a strong feeling what she was about to order me to do.
“Clean off his dick, Petra,” the warden commanded.
“N-no!” I blurted.
I said it with barely a whisper but she heard. In four long strides she stood before me. “On your knees, prisoner Hartmann.”
I dropped as fast as if someone had kicked my legs out. My knees stung as they hit the carpeted floor. I was afraid to look into her face. My balls tingled with fear. Gooseflesh covered my body.
“I don’t believe I heard you correctly,” she said icily.
“I made a mistake!” I cried. “I’m sorry! I’m sorry!” I stared at the carpet.
“May I speak, Mistress?” Rita asked urgently.
“Speak!” the warden barked. I could tell she was still looking down at me.
“She’s young and scared and never been in any situation like this. I promise to teach Petra her place. Please be lenient with her.”
Gratitude filled my heart and I fell a little more in love with her right then.
“Look at me, Petra,” Warden Fordham ordered.
I timidly raised my gaze to see her glaring down at me before she looked over to Rita, her expression softening.
“That’s very sweet of you, Rita. Considering how you’ve already more than proven your worth, I might otherwise be willing to consider your request. However I think you’re a smart enough girl to know why I can’t allow you to teach this fishie her place. Can you tell me why?”
“Because it’s your job, Mistress.”
“Rita,” the warden said with a smile, “that’s three times today you’ve pleased me, so I will be a little bit more lenient than I was planning.” She looked back at me. “I gave you an order, Petra. Go suck his cock.”
I knelt in front of Officer Garrett. His dick was still hard. It glistened with lube and cum. Fortunately, it didn’t look dirty but it still smelled faintly of ass. I looked past him and into Rita’s eyes and saw her looking back at me so tenderly it was easy to imagine she did love me, which made what I was about to do so much easier.
I gave the CO’s cock a long lick. It tasted earthy and pungent, a little sharp. It was the taste from deep up inside my darling Rita. Suddenly that very thought turned me on like I never imagined it could, but only because it was the taste of her ass. Before I could think a moment longer I lowered my mouth onto his dick and began sucking greedily like a little kid with a popsicle on a hot day.
If it wasn’t Rita’s ass—my only true love in the world—I’d have been repulsed. Then I realized this would be a way to show her how much I loved her. I sucked and sucked and made mewling sounds of pleasure. After two minutes the warden ordered me to stop.
“You love the taste of Rita, don’t you?”
“Yes, Mistress!” I enthused. “I love everything about her.”
“You want to be just like her, don’t you?”
“Yes, Mistress!”
“Then you must be properly trained. Officer Hayes and Captain Grover, get the horse and bring it here.”
For a few seconds I imagined them bringing in an actual horse but the two guards went into one of the doors on the wall, which turned out to be walk-in closets. They brought out a big sawhorse-type piece of furniture with a wide padded top and legs. Each of the four legs had thick eyehooks set into them with padded leather cuffs attached to each with a rope that tied off at the bottom of the leg.
“Andie, bring the tarp,” she commanded.
One minute later our shemale guide had spread a ten-by-ten waterproof tarp. The guards set the horse in the middle of the tarp. Hayes looked me up and down and shortened the length of the top with some levers and locked it into place. All of a sudden I was frightened, realizing I was to be tied down, completely helpless. The tarp made me even more nervous.
Following the warden’s orders I lay across the top and draped my arms down the front legs. My chin rested perfectly on the far end of the horse. My legs were spread wide and cuffs attached at ankles; then the ropes were pulled until my legs were tied fully to the back legs of the bondage horse. The same was done with my arms down the front legs. I could barely move a muscle and I was fully exposed: my balls, my spread asscheeks and my mouth. My dick was trapped under my body between my tummy and the horse’s padded top.
“Mistress?” Rita asked. “Another question please?”
She looked at my lover with a charitable smile. “Let me guess: you want to be with her during her chastisement. Hold her hand and look into her eyes. Was that it?”
“My Mistress knows her girl so well,” Rita replied. It seemed to me that she was following some kind of ritual or etiquette that had to do with all this bondage and dominance and stuff.
“Again, very kind of you, but she must face her first discipline all alone. She can’t learn her lesson if it is shared. I will permit you to comfort her afterward.”
Mistress Fordham had circled behind me as she spoke. Out of nowhere came a cruel whistle of air as she swung the cane. The sound it made on my skin was oddly quiet, like a soft thud, but then my asscheeks felt scorched, like a red-hot poker had been pulled out of a fire and laid across my ass. I screamed. If I had not been tied down tightly to the “horse” I would have not been able to help jumping up.
Electric shocks fired down my legs and up my spine. What just happened to me was only beginning to register when that terrifying cut through the air repeated, and a new burning line crossed my ass. I was dizzy from the enormity of the pain. Another fell. And another. And another. The stripes of agony all added up to make me dizzy and weak. And yet my cock still tingled, halfway erect.
Without warning I felt warmness, a wet warmness under my stomach. I realized why the tarp had been put onto the floor: I had just pissed myself. In between the violent parting of the air and the blows I heard my pee dripping onto the rubberized canvas. The warden must have heard it too because she stopped beating me and tossed the cane onto her desk. She crouched down and looked into my eyes.
“Do you now grasp what punishment is? The consequences of disobedience?”
“Yes, Mistress,” I sobbed, half in pain and half in relief it might be over.
“Now grasp this: I was holding back seventy-five percent of what I can dish out. I can break your skin with that cane; I can open your asscheeks up so badly the liquid trickling down your legs will be your own blood.” She turned her back, walked to the edge of her desk and sat. “Rita, you may comfort her now.”
Naked and sweaty, Rita knelt in front of me and took my bound hands in hers. She looked into my eyes and whispered it was all going to be okay. She started planting soft kisses. In between those kisses she assured me I’d never have to feel that again as long as I obeyed without question, as long as I strove to please my owners and those I served, and as long I always kept getting better at being a sissy and a whore.
“Okay, that’s enough. Get out of there, Rita. It’s time to see if she’s even one tenth as good as you at sucking and fucking.” She looked to the trustee. “Andie, you’ve been such a good girl this week.”
“Thank you, Ma’am,” the stunning brunette said with a curtsy.
“Why don’t you be the first of our happy home to sample the girl’s cocksucking?”
“Shall a girl disrobe completely, Ma’am?” Andie asked.
“By all means. Let everyone enjoy your sexy body.”
The trustee kicked off her loafers, revealing some kind of hosiery beneath her institutional uniform. In a slow and deliberate striptease, Andie removed her prisoner top to reveal an expensive, lacy demi bra that thrust large C-cup tits with big, erect nipples out for all to see. Then came off her denims to reveal a matching garter belt and sheer, tan stockings. A big cock bulged at her lacy, French-cut panties. With sparkling brown eyes she looked hungrily at me. She sashayed up to me where I was still tied down to the horse; my mouth was level with her crotch. She was so very beautiful—every bit as much as darling Rita.
“You’re such a pretty sissy,” she said. “Eighteen and already so very feminine.” She eased down her panties a couple inches and freed up a cock maybe nine inches long and getting harder by the moment. “Suck it, baby.”
Eagerly I closed my mouth around her tranny boner, not caring how slutty my hungry slurping noises made me sound. I loved the feel of her firm, tanned dickflesh between my lips, pulsating in my mouth, the hot plump head sliding in and out. I strained to move my head forward, to try to take her into the back of my throat.
“It looks like she’s trying to deepthroat me, Ma’am,” Andie said. “She has true potential indeed… Do you think you should tell her?”
The warden chuckled darkly. “I think it would put her even more in the proper frame of mind.” I sensed the warden moving next to me, felt her hand softly stroking my ass she’d so severely whipped. “It was no accident you were arrested in that porno shop. It’s one of a dozen such places our… associates have under surveillance. For the most part they’re conducting their normal vice operations, but certain members, such as that sergeant you knew as Pat, are always on the lookout for us. They’re looking out for sissies like you who have the potential to become shemales like Rita or our lovely Andie you’re so eagerly giving a blowjob to. Pat waited for you to do what you know you wanted to, she made up a few additional charges to ensure you got into the state prison system. Another associate got you sent here.”
A deep hollow feeling opened up inside me as she described how I’d been set up, actually chosen for this place. Pat must have had her eye on me for months, assessing me. I had been all but kidnapped and brought here to be a whore for the warden and everyone who worked for her. From what she said, I was also brought here to become a shemale.
The shocking thing was how excited I was by my growing sense of helplessness. I loved the feel of my new owner possessively, fondly stroked the bottom she just beat. The notion of being enslaved as a sissy gave me a hard-on that ached deeply. I moaned over and over while I sucked Andie’s huge clit. Almost as if she understood my feelings I felt the warden’s hand reached between the piss-soaked horse and my tummy and feel my cock. She laughed with delight.
“You’re hard as a rock at your predicament,” she said smugly, wiping her hand dry on my back. “You’re home and you don’t even know it yet. Officer Lewis, welcome our newest sissy to her new home.”
I heard the rasp of a zipper and the squish of lubricant. A thick slippery finger coated my asshole and easily pushed up inside. I moaned again. Then a big dick plowed up my asshole. Soon Andie and the CO found a rhythm, taking turns burying their cocks all the way into my mouth and asshole.
“Switch!” the warden called several minutes later.
Without hesitation I sucked the dick fresh from my asshole while Andie’s nine-inch cock starting fucking deep up inside my ass. The dominatrix warden got me more and more excited as she described how I would be fully transitioned into a shemale.
“That it… if you really want to be,” she concluded.
“Mmmm-hmmm! Mmmm-hmmm!” I whined in lust, meaning it with all my heart.
I was a nasty, dirty slut and I was glad!
The third time Andie went into my mouth she blew a deep glut of thick, tangy cum all over my tongue and teeth. Gently fucking my mouth with her softening boner, she gave me a kind smile and caressed my face. “You’re going to love it here,” she assured me. “I can tell.”
Then CO Lewis stuck his cock into my face and I dove on it happily, Andie’s words tantalizing my brain. I he
i like, alot
her so much!
Her plump red lips glistened with the black man’s cum—a foot-long wang that had been buried all the way up her ass only minutes ago. Now she was finishing off Officer Garrett, and by the ecstatic expression on his face she was milking his dick with her asshole. I decided right then and there I wanted her to teach me everything: how to suck a dick that big, to have control over my ass muscles, to be able to actually do ass-to-mouth and not get all queasy.
Shortly after the CO blew his load up my tranny lover’s ass. He pulled it out, but when Rita turned around to suck it clean the warden stopped her. She told Officer Garrett to get on his feet and to face me. A hollow feeling filled the pit of my stomach because I had a strong feeling what she was about to order me to do.
“Clean off his dick, Petra,” the warden commanded.
“N-no!” I blurted.
I said it with barely a whisper but she heard. In four long strides she stood before me. “On your knees, prisoner Hartmann.”
I dropped as fast as if someone had kicked my legs out. My knees stung as they hit the carpeted floor. I was afraid to look into her face. My balls tingled with fear. Gooseflesh covered my body.
“I don’t believe I heard you correctly,” she said icily.
“I made a mistake!” I cried. “I’m sorry! I’m sorry!” I stared at the carpet.
“May I speak, Mistress?” Rita asked urgently.
“Speak!” the warden barked. I could tell she was still looking down at me.
“She’s young and scared and never been in any situation like this. I promise to teach Petra her place. Please be lenient with her.”
Gratitude filled my heart and I fell a little more in love with her right then.
“Look at me, Petra,” Warden Fordham ordered.
I timidly raised my gaze to see her glaring down at me before she looked over to Rita, her expression softening.
“That’s very sweet of you, Rita. Considering how you’ve already more than proven your worth, I might otherwise be willing to consider your request. However I think you’re a smart enough girl to know why I can’t allow you to teach this fishie her place. Can you tell me why?”
“Because it’s your job, Mistress.”
“Rita,” the warden said with a smile, “that’s three times today you’ve pleased me, so I will be a little bit more lenient than I was planning.” She looked back at me. “I gave you an order, Petra. Go suck his cock.”
I knelt in front of Officer Garrett. His dick was still hard. It glistened with lube and cum. Fortunately, it didn’t look dirty but it still smelled faintly of ass. I looked past him and into Rita’s eyes and saw her looking back at me so tenderly it was easy to imagine she did love me, which made what I was about to do so much easier.
I gave the CO’s cock a long lick. It tasted earthy and pungent, a little sharp. It was the taste from deep up inside my darling Rita. Suddenly that very thought turned me on like I never imagined it could, but only because it was the taste of her ass. Before I could think a moment longer I lowered my mouth onto his dick and began sucking greedily like a little kid with a popsicle on a hot day.
If it wasn’t Rita’s ass—my only true love in the world—I’d have been repulsed. Then I realized this would be a way to show her how much I loved her. I sucked and sucked and made mewling sounds of pleasure. After two minutes the warden ordered me to stop.
“You love the taste of Rita, don’t you?”
“Yes, Mistress!” I enthused. “I love everything about her.”
“You want to be just like her, don’t you?”
“Yes, Mistress!”
“Then you must be properly trained. Officer Hayes and Captain Grover, get the horse and bring it here.”
For a few seconds I imagined them bringing in an actual horse but the two guards went into one of the doors on the wall, which turned out to be walk-in closets. They brought out a big sawhorse-type piece of furniture with a wide padded top and legs. Each of the four legs had thick eyehooks set into them with padded leather cuffs attached to each with a rope that tied off at the bottom of the leg.
“Andie, bring the tarp,” she commanded.
One minute later our shemale guide had spread a ten-by-ten waterproof tarp. The guards set the horse in the middle of the tarp. Hayes looked me up and down and shortened the length of the top with some levers and locked it into place. All of a sudden I was frightened, realizing I was to be tied down, completely helpless. The tarp made me even more nervous.
Following the warden’s orders I lay across the top and draped my arms down the front legs. My chin rested perfectly on the far end of the horse. My legs were spread wide and cuffs attached at ankles; then the ropes were pulled until my legs were tied fully to the back legs of the bondage horse. The same was done with my arms down the front legs. I could barely move a muscle and I was fully exposed: my balls, my spread asscheeks and my mouth. My dick was trapped under my body between my tummy and the horse’s padded top.
“Mistress?” Rita asked. “Another question please?”
She looked at my lover with a charitable smile. “Let me guess: you want to be with her during her chastisement. Hold her hand and look into her eyes. Was that it?”
“My Mistress knows her girl so well,” Rita replied. It seemed to me that she was following some kind of ritual or etiquette that had to do with all this bondage and dominance and stuff.
“Again, very kind of you, but she must face her first discipline all alone. She can’t learn her lesson if it is shared. I will permit you to comfort her afterward.”
Mistress Fordham had circled behind me as she spoke. Out of nowhere came a cruel whistle of air as she swung the cane. The sound it made on my skin was oddly quiet, like a soft thud, but then my asscheeks felt scorched, like a red-hot poker had been pulled out of a fire and laid across my ass. I screamed. If I had not been tied down tightly to the “horse” I would have not been able to help jumping up.
Electric shocks fired down my legs and up my spine. What just happened to me was only beginning to register when that terrifying cut through the air repeated, and a new burning line crossed my ass. I was dizzy from the enormity of the pain. Another fell. And another. And another. The stripes of agony all added up to make me dizzy and weak. And yet my cock still tingled, halfway erect.
Without warning I felt warmness, a wet warmness under my stomach. I realized why the tarp had been put onto the floor: I had just pissed myself. In between the violent parting of the air and the blows I heard my pee dripping onto the rubberized canvas. The warden must have heard it too because she stopped beating me and tossed the cane onto her desk. She crouched down and looked into my eyes.
“Do you now grasp what punishment is? The consequences of disobedience?”
“Yes, Mistress,” I sobbed, half in pain and half in relief it might be over.
“Now grasp this: I was holding back seventy-five percent of what I can dish out. I can break your skin with that cane; I can open your asscheeks up so badly the liquid trickling down your legs will be your own blood.” She turned her back, walked to the edge of her desk and sat. “Rita, you may comfort her now.”
Naked and sweaty, Rita knelt in front of me and took my bound hands in hers. She looked into my eyes and whispered it was all going to be okay. She started planting soft kisses. In between those kisses she assured me I’d never have to feel that again as long as I obeyed without question, as long as I strove to please my owners and those I served, and as long I always kept getting better at being a sissy and a whore.
“Okay, that’s enough. Get out of there, Rita. It’s time to see if she’s even one tenth as good as you at sucking and fucking.” She looked to the trustee. “Andie, you’ve been such a good girl this week.”
“Thank you, Ma’am,” the stunning brunette said with a curtsy.
“Why don’t you be the first of our happy home to sample the girl’s cocksucking?”
“Shall a girl disrobe completely, Ma’am?” Andie asked.
“By all means. Let everyone enjoy your sexy body.”
The trustee kicked off her loafers, revealing some kind of hosiery beneath her institutional uniform. In a slow and deliberate striptease, Andie removed her prisoner top to reveal an expensive, lacy demi bra that thrust large C-cup tits with big, erect nipples out for all to see. Then came off her denims to reveal a matching garter belt and sheer, tan stockings. A big cock bulged at her lacy, French-cut panties. With sparkling brown eyes she looked hungrily at me. She sashayed up to me where I was still tied down to the horse; my mouth was level with her crotch. She was so very beautiful—every bit as much as darling Rita.
“You’re such a pretty sissy,” she said. “Eighteen and already so very feminine.” She eased down her panties a couple inches and freed up a cock maybe nine inches long and getting harder by the moment. “Suck it, baby.”
Eagerly I closed my mouth around her tranny boner, not caring how slutty my hungry slurping noises made me sound. I loved the feel of her firm, tanned dickflesh between my lips, pulsating in my mouth, the hot plump head sliding in and out. I strained to move my head forward, to try to take her into the back of my throat.
“It looks like she’s trying to deepthroat me, Ma’am,” Andie said. “She has true potential indeed… Do you think you should tell her?”
The warden chuckled darkly. “I think it would put her even more in the proper frame of mind.” I sensed the warden moving next to me, felt her hand softly stroking my ass she’d so severely whipped. “It was no accident you were arrested in that porno shop. It’s one of a dozen such places our… associates have under surveillance. For the most part they’re conducting their normal vice operations, but certain members, such as that sergeant you knew as Pat, are always on the lookout for us. They’re looking out for sissies like you who have the potential to become shemales like Rita or our lovely Andie you’re so eagerly giving a blowjob to. Pat waited for you to do what you know you wanted to, she made up a few additional charges to ensure you got into the state prison system. Another associate got you sent here.”
A deep hollow feeling opened up inside me as she described how I’d been set up, actually chosen for this place. Pat must have had her eye on me for months, assessing me. I had been all but kidnapped and brought here to be a whore for the warden and everyone who worked for her. From what she said, I was also brought here to become a shemale.
The shocking thing was how excited I was by my growing sense of helplessness. I loved the feel of my new owner possessively, fondly stroked the bottom she just beat. The notion of being enslaved as a sissy gave me a hard-on that ached deeply. I moaned over and over while I sucked Andie’s huge clit. Almost as if she understood my feelings I felt the warden’s hand reached between the piss-soaked horse and my tummy and feel my cock. She laughed with delight.
“You’re hard as a rock at your predicament,” she said smugly, wiping her hand dry on my back. “You’re home and you don’t even know it yet. Officer Lewis, welcome our newest sissy to her new home.”
I heard the rasp of a zipper and the squish of lubricant. A thick slippery finger coated my asshole and easily pushed up inside. I moaned again. Then a big dick plowed up my asshole. Soon Andie and the CO found a rhythm, taking turns burying their cocks all the way into my mouth and asshole.
“Switch!” the warden called several minutes later.
Without hesitation I sucked the dick fresh from my asshole while Andie’s nine-inch cock starting fucking deep up inside my ass. The dominatrix warden got me more and more excited as she described how I would be fully transitioned into a shemale.
“That it… if you really want to be,” she concluded.
“Mmmm-hmmm! Mmmm-hmmm!” I whined in lust, meaning it with all my heart.
I was a nasty, dirty slut and I was glad!
The third time Andie went into my mouth she blew a deep glut of thick, tangy cum all over my tongue and teeth. Gently fucking my mouth with her softening boner, she gave me a kind smile and caressed my face. “You’re going to love it here,” she assured me. “I can tell.”
Then CO Lewis stuck his cock into my face and I dove on it happily, Andie’s words tantalizing my brain. I he
shemale, a true force in and of herself when she was having sex. Even something I thought of as degrading as ass-to-mouth she made it look beautiful and wholesome. I wanted to be her so much!
Her plump red lips glistened with the black man’s cum—a foot-long wang that had been buried all the way up her ass only minutes ago. Now she was finishing off Officer Garrett, and by the ecstatic expression on his face she was milking his dick with her asshole. I decided right then and there I wanted her to teach me everything: how to suck a dick that big, to have control over my ass muscles, to be able to actually do ass-to-mouth and not get all queasy.
Shortly after the CO blew his load up my tranny lover’s ass. He pulled it out, but when Rita turned around to suck it clean the warden stopped her. She told Officer Garrett to get on his feet and to face me. A hollow feeling filled the pit of my stomach because I had a strong feeling what she was about to order me to do.
“Clean off his dick, Petra,” the warden commanded.
“N-no!” I blurted.
I said it with barely a whisper but she heard. In four long strides she stood before me. “On your knees, prisoner Hartmann.”
I dropped as fast as if someone had kicked my legs out. My knees stung as they hit the carpeted floor. I was afraid to look into her face. My balls tingled with fear. Gooseflesh covered my body.
“I don’t believe I heard you correctly,” she said icily.
“I made a mistake!” I cried. “I’m sorry! I’m sorry!” I stared at the carpet.
“May I speak, Mistress?” Rita asked urgently.
“Speak!” the warden barked. I could tell she was still looking down at me.
“She’s young and scared and never been in any situation like this. I promise to teach Petra her place. Please be lenient with her.”
Gratitude filled my heart and I fell a little more in love with her right then.
“Look at me, Petra,” Warden Fordham ordered.
I timidly raised my gaze to see her glaring down at me before she looked over to Rita, her expression softening.
“That’s very sweet of you, Rita. Considering how you’ve already more than proven your worth, I might otherwise be willing to consider your request. However I think you’re a smart enough girl to know why I can’t allow you to teach this fishie her place. Can you tell me why?”
“Because it’s your job, Mistress.”
“Rita,” the warden said with a smile, “that’s three times today you’ve pleased me, so I will be a little bit more lenient than I was planning.” She looked back at me. “I gave you an order, Petra. Go suck his cock.”
I knelt in front of Officer Garrett. His dick was still hard. It glistened with lube and cum. Fortunately, it didn’t look dirty but it still smelled faintly of ass. I looked past him and into Rita’s eyes and saw her looking back at me so tenderly it was easy to imagine she did love me, which made what I was about to do so much easier.
I gave the CO’s cock a long lick. It tasted earthy and pungent, a little sharp. It was the taste from deep up inside my darling Rita. Suddenly that very thought turned me on like I never imagined it could, but only because it was the taste of her ass. Before I could think a moment longer I lowered my mouth onto his dick and began sucking greedily like a little kid with a popsicle on a hot day.
If it wasn’t Rita’s ass—my only true love in the world—I’d have been repulsed. Then I realized this would be a way to show her how much I loved her. I sucked and sucked and made mewling sounds of pleasure. After two minutes the warden ordered me to stop.
“You love the taste of Rita, don’t you?”
“Yes, Mistress!” I enthused. “I love everything about her.”
“You want to be just like her, don’t you?”
“Yes, Mistress!”
“Then you must be properly trained. Officer Hayes and Captain Grover, get the horse and bring it here.”
For a few seconds I imagined them bringing in an actual horse but the two guards went into one of the doors on the wall, which turned out to be walk-in closets. They brought out a big sawhorse-type piece of furniture with a wide padded top and legs. Each of the four legs had thick eyehooks set into them with padded leather cuffs attached to each with a rope that tied off at the bottom of the leg.
“Andie, bring the tarp,” she commanded.
One minute later our shemale guide had spread a ten-by-ten waterproof tarp. The guards set the horse in the middle of the tarp. Hayes looked me up and down and shortened the length of the top with some levers and locked it into place. All of a sudden I was frightened, realizing I was to be tied down, completely helpless. The tarp made me even more nervous.
Following the warden’s orders I lay across the top and draped my arms down the front legs. My chin rested perfectly on the far end of the horse. My legs were spread wide and cuffs attached at ankles; then the ropes were pulled until my legs were tied fully to the back legs of the bondage horse. The same was done with my arms down the front legs. I could barely move a muscle and I was fully exposed: my balls, my spread asscheeks and my mouth. My dick was trapped under my body between my tummy and the horse’s padded top.
“Mistress?” Rita asked. “Another question please?”
She looked at my lover with a charitable smile. “Let me guess: you want to be with her during her chastisement. Hold her hand and look into her eyes. Was that it?”
“My Mistress knows her girl so well,” Rita replied. It seemed to me that she was following some kind of ritual or etiquette that had to do with all this bondage and dominance and stuff.
“Again, very kind of you, but she must face her first discipline all alone. She can’t learn her lesson if it is shared. I will permit you to comfort her afterward.”
Mistress Fordham had circled behind me as she spoke. Out of nowhere came a cruel whistle of air as she swung the cane. The sound it made on my skin was oddly quiet, like a soft thud, but then my asscheeks felt scorched, like a red-hot poker had been pulled out of a fire and laid across my ass. I screamed. If I had not been tied down tightly to the “horse” I would have not been able to help jumping up.
Electric shocks fired down my legs and up my spine. What just happened to me was only beginning to register when that terrifying cut through the air repeated, and a new burning line crossed my ass. I was dizzy from the enormity of the pain. Another fell. And another. And another. The stripes of agony all added up to make me dizzy and weak. And yet my cock still tingled, halfway erect.
Without warning I felt warmness, a wet warmness under my stomach. I realized why the tarp had been put onto the floor: I had just pissed myself. In between the violent parting of the air and the blows I heard my pee dripping onto the rubberized canvas. The warden must have heard it too because she stopped beating me and tossed the cane onto her desk. She crouched down and looked into my eyes.
“Do you now grasp what punishment is? The consequences of disobedience?”
“Yes, Mistress,” I sobbed, half in pain and half in relief it might be over.
“Now grasp this: I was holding back seventy-five percent of what I can dish out. I can break your skin with that cane; I can open your asscheeks up so badly the liquid trickling down your legs will be your own blood.” She turned her back, walked to the edge of her desk and sat. “Rita, you may comfort her now.”
Naked and sweaty, Rita knelt in front of me and took my bound hands in hers. She looked into my eyes and whispered it was all going to be okay. She started planting soft kisses. In between those kisses she assured me I’d never have to feel that again as long as I obeyed without question, as long as I strove to please my owners and those I served, and as long I always kept getting better at being a sissy and a whore.
“Okay, that’s enough. Get out of there, Rita. It’s time to see if she’s even one tenth as good as you at sucking and fucking.” She looked to the trustee. “Andie, you’ve been such a good girl this week.”
“Thank you, Ma’am,” the stunning brunette said with a curtsy.
“Why don’t you be the first of our happy home to sample the girl’s cocksucking?”
“Shall a girl disrobe completely, Ma’am?” Andie asked.
“By all means. Let everyone enjoy your sexy body.”
The trustee kicked off her loafers, revealing some kind of hosiery beneath her institutional uniform. In a slow and deliberate striptease, Andie removed her prisoner top to reveal an expensive, lacy demi bra that thrust large C-cup tits with big, erect nipples out for all to see. Then came off her denims to reveal a matching garter belt and sheer, tan stockings. A big cock bulged at her lacy, French-cut panties. With sparkling brown eyes she looked hungrily at me. She sashayed up to me where I was still tied down to the horse; my mouth was level with her crotch. She was so very beautiful—every bit as much as darling Rita.
“You’re such a pretty sissy,” she said. “Eighteen and already so very feminine.” She eased down her panties a couple inches and freed up a cock maybe nine inches long and getting harder by the moment. “Suck it, baby.”
Eagerly I closed my mouth around her tranny boner, not caring how slutty my hungry slurping noises made me sound. I loved the feel of her firm, tanned dickflesh between my lips, pulsating in my mouth, the hot plump head sliding in and out. I strained to move my head forward, to try to take her into the back of my throat.
“It looks like she’s trying to deepthroat me, Ma’am,” Andie said. “She has true potential indeed… Do you think you should tell her?”
The warden chuckled darkly. “I think it would put her even more in the proper frame of mind.” I sensed the warden moving next to me, felt her hand softly stroking my ass she’d so severely whipped. “It was no accident you were arrested in that porno shop. It’s one of a dozen such places our… associates have under surveillance. For the most part they’re conducting their normal vice operations, but certain members, such as that sergeant you knew as Pat, are always on the lookout for us. They’re looking out for sissies like you who have the potential to become shemales like Rita or our lovely Andie you’re so eagerly giving a blowjob to. Pat waited for you to do what you know you wanted to, she made up a few additional charges to ensure you got into the state prison system. Another associate got you sent here.”
A deep hollow feeling opened up inside me as she described how I’d been set up, actually chosen for this place. Pat must have had her eye on me for months, assessing me. I had been all but kidnapped and brought here to be a whore for the warden and everyone who worked for her. From what she said, I was also brought here to become a shemale.
The shocking thing was how excited I was by my growing sense of helplessness. I loved the feel of my new owner possessively, fondly stroked the bottom she just beat. The notion of being enslaved as a sissy gave me a hard-on that ached deeply. I moaned over and over while I sucked Andie’s huge clit. Almost as if she understood my feelings I felt the warden’s hand reached between the piss-soaked horse and my tummy and feel my cock. She laughed with delight.
“You’re hard as a rock at your predicament,” she said smugly, wiping her hand dry on my back. “You’re home and you don’t even know it yet. Officer Lewis, welcome our newest sissy to her new home.”
I heard the rasp of a zipper and the squish of lubricant. A thick slippery finger coated my asshole and easily pushed up inside. I moaned again. Then a big dick plowed up my asshole. Soon Andie and the CO found a rhythm, taking turns burying their cocks all the way into my mouth and asshole.
“Switch!” the warden called several minutes later.
Without hesitation I sucked the dick fresh from my asshole while Andie’s nine-inch cock starting fucking deep up inside my ass. The dominatrix warden got me more and more excited as she described how I would be fully transitioned into a shemale.
“That it… if you really want to be,” she concluded.
“Mmmm-hmmm! Mmmm-hmmm!” I whined in lust, meaning it with all my heart.
I was a nasty, dirty slut and I was glad!
The third time Andie went into my mouth she blew a deep glut of thick, tangy cum all over my tongue and teeth. Gently fucking my mouth with her softening boner, she gave me a kind smile and caressed my face. “You’re going to love it here,” she assured me. “I can tell.”
Then CO Lewis stuck his cock into my face and I dove on it happily, Andie’s words tantalizing my brain. I he
Meanwhile at SHEMALE PRISON in the next county over…
—
I stood at my original position in front of the desk but I had turned to the right so I could see my shemale mentor in action. I looked at Rita with complete awe, even more than before. She was so filled with sexual hunger she looked like a true nymph goddess in her fucking and sucking. She might be a sex slave—as I probably was now too—but she was also a powerful shemale, a true force in and of herself when she was having sex. Even something I thought of as degrading as ass-to-mouth she made it look beautiful and wholesome. I wanted to be her so much!
Her plump red lips glistened with the black man’s cum—a foot-long wang that had been buried all the way up her ass only minutes ago. Now she was finishing off Officer Garrett, and by the ecstatic expression on his face she was milking his dick with her asshole. I decided right then and there I wanted her to teach me everything: how to suck a dick that big, to have control over my ass muscles, to be able to actually do ass-to-mouth and not get all queasy.
Shortly after the CO blew his load up my tranny lover’s ass. He pulled it out, but when Rita turned around to suck it clean the warden stopped her. She told Officer Garrett to get on his feet and to face me. A hollow feeling filled the pit of my stomach because I had a strong feeling what she was about to order me to do.
“Clean off his dick, Petra,” the warden commanded.
“N-no!” I blurted.
I said it with barely a whisper but she heard. In four long strides she stood before me. “On your knees, prisoner Hartmann.”
I dropped as fast as if someone had kicked my legs out. My knees stung as they hit the carpeted floor. I was afraid to look into her face. My balls tingled with fear. Gooseflesh covered my body.
“I don’t believe I heard you correctly,” she said icily.
“I made a mistake!” I cried. “I’m sorry! I’m sorry!” I stared at the carpet.
“May I speak, Mistress?” Rita asked urgently.
“Speak!” the warden barked. I could tell she was still looking down at me.
“She’s young and scared and never been in any situation like this. I promise to teach Petra her place. Please be lenient with her.”
Gratitude filled my heart and I fell a little more in love with her right then.
“Look at me, Petra,” Warden Fordham ordered.
I timidly raised my gaze to see her glaring down at me before she looked over to Rita, her expression softening.
“That’s very sweet of you, Rita. Considering how you’ve already more than proven your worth, I might otherwise be willing to consider your request. However I think you’re a smart enough girl to know why I can’t allow you to teach this fishie her place. Can you tell me why?”
“Because it’s your job, Mistress.”
“Rita,” the warden said with a smile, “that’s three times today you’ve pleased me, so I will be a little bit more lenient than I was planning.” She looked back at me. “I gave you an order, Petra. Go suck his cock.”
I knelt in front of Officer Garrett. His dick was still hard. It glistened with lube and cum. Fortunately, it didn’t look dirty but it still smelled faintly of ass. I looked past him and into Rita’s eyes and saw her looking back at me so tenderly it was easy to imagine she did love me, which made what I was about to do so much easier.
I gave the CO’s cock a long lick. It tasted earthy and pungent, a little sharp. It was the taste from deep up inside my darling Rita. Suddenly that very thought turned me on like I never imagined it could, but only because it was the taste of her ass. Before I could think a moment longer I lowered my mouth onto his dick and began sucking greedily like a little kid with a popsicle on a hot day.
If it wasn’t Rita’s ass—my only true love in the world—I’d have been repulsed. Then I realized this would be a way to show her how much I loved her. I sucked and sucked and made mewling sounds of pleasure. After two minutes the warden ordered me to stop.
“You love the taste of Rita, don’t you?”
“Yes, Mistress!” I enthused. “I love everything about her.”
“You want to be just like her, don’t you?”
“Yes, Mistress!”
“Then you must be properly trained. Officer Hayes and Captain Grover, get the horse and bring it here.”
For a few seconds I imagined them bringing in an actual horse but the two guards went into one of the doors on the wall, which turned out to be walk-in closets. They brought out a big sawhorse-type piece of furniture with a wide padded top and legs. Each of the four legs had thick eyehooks set into them with padded leather cuffs attached to each with a rope that tied off at the bottom of the leg.
“Andie, bring the tarp,” she commanded.
One minute later our shemale guide had spread a ten-by-ten waterproof tarp. The guards set the horse in the middle of the tarp. Hayes looked me up and down and shortened the length of the top with some levers and locked it into place. All of a sudden I was frightened, realizing I was to be tied down, completely helpless. The tarp made me even more nervous.
Following the warden’s orders I lay across the top and draped my arms down the front legs. My chin rested perfectly on the far end of the horse. My legs were spread wide and cuffs attached at ankles; then the ropes were pulled until my legs were tied fully to the back legs of the bondage horse. The same was done with my arms down the front legs. I could barely move a muscle and I was fully exposed: my balls, my spread asscheeks and my mouth. My dick was trapped under my body between my tummy and the horse’s padded top.
“Mistress?” Rita asked. “Another question please?”
She looked at my lover with a charitable smile. “Let me guess: you want to be with her during her chastisement. Hold her hand and look into her eyes. Was that it?”
“My Mistress knows her girl so well,” Rita replied. It seemed to me that she was following some kind of ritual or etiquette that had to do with all this bondage and dominance and stuff.
“Again, very kind of you, but she must face her first discipline all alone. She can’t learn her lesson if it is shared. I will permit you to comfort her afterward.”
Mistress Fordham had circled behind me as she spoke. Out of nowhere came a cruel whistle of air as she swung the cane. The sound it made on my skin was oddly quiet, like a soft thud, but then my asscheeks felt scorched, like a red-hot poker had been pulled out of a fire and laid across my ass. I screamed. If I had not been tied down tightly to the “horse” I would have not been able to help jumping up.
Electric shocks fired down my legs and up my spine. What just happened to me was only beginning to register when that terrifying cut through the air repeated, and a new burning line crossed my ass. I was dizzy from the enormity of the pain. Another fell. And another. And another. The stripes of agony all added up to make me dizzy and weak. And yet my cock still tingled, halfway erect.
Without warning I felt warmness, a wet warmness under my stomach. I realized why the tarp had been put onto the floor: I had just pissed myself. In between the violent parting of the air and the blows I heard my pee dripping onto the rubberized canvas. The warden must have heard it too because she stopped beating me and tossed the cane onto her desk. She crouched down and looked into my eyes.
“Do you now grasp what punishment is? The consequences of disobedience?”
“Yes, Mistress,” I sobbed, half in pain and half in relief it might be over.
“Now grasp this: I was holding back seventy-five percent of what I can dish out. I can break your skin with that cane; I can open your asscheeks up so badly the liquid trickling down your legs will be your own blood.” She turned her back, walked to the edge of her desk and sat. “Rita, you may comfort her now.”
Naked and sweaty, Rita knelt in front of me and took my bound hands in hers. She looked into my eyes and whispered it was all going to be okay. She started planting soft kisses. In between those kisses she assured me I’d never have to feel that again as long as I obeyed without question, as long as I strove to please my owners and those I served, and as long I always kept getting better at being a sissy and a whore.
“Okay, that’s enough. Get out of there, Rita. It’s time to see if she’s even one tenth as good as you at sucking and fucking.” She looked to the trustee. “Andie, you’ve been such a good girl this week.”
“Thank you, Ma’am,” the stunning brunette said with a curtsy.
“Why don’t you be the first of our happy home to sample the girl’s cocksucking?”
“Shall a girl disrobe completely, Ma’am?” Andie asked.
“By all means. Let everyone enjoy your sexy body.”
The trustee kicked off her loafers, revealing some kind of hosiery beneath her institutional uniform. In a slow and deliberate striptease, Andie removed her prisoner top to reveal an expensive, lacy demi bra that thrust large C-cup tits with big, erect nipples out for all to see. Then came off her denims to reveal a matching garter belt and sheer, tan stockings. A big cock bulged at her lacy, French-cut panties. With sparkling brown eyes she looked hungrily at me. She sashayed up to me where I was still tied down to the horse; my mouth was level with her crotch. She was so very beautiful—every bit as much as darling Rita.
“You’re such a pretty sissy,” she said. “Eighteen and already so very feminine.” She eased down her panties a couple inches and freed up a cock maybe nine inches long and getting harder by the moment. “Suck it, baby.”
Eagerly I closed my mouth around her tranny boner, not caring how slutty my hungry slurping noises made me sound. I loved the feel of her firm, tanned dickflesh between my lips, pulsating in my mouth, the hot plump head sliding in and out. I strained to move my head forward, to try to take her into the back of my throat.
“It looks like she’s trying to deepthroat me, Ma’am,” Andie said. “She has true potential indeed… Do you think you should tell her?”
The warden chuckled darkly. “I think it would put her even more in the proper frame of mind.” I sensed the warden moving next to me, felt her hand softly stroking my ass she’d so severely whipped. “It was no accident you were arrested in that porno shop. It’s one of a dozen such places our… associates have under surveillance. For the most part they’re conducting their normal vice operations, but certain members, such as that sergeant you knew as Pat, are always on the lookout for us. They’re looking out for sissies like you who have the potential to become shemales like Rita or our lovely Andie you’re so eagerly giving a blowjob to. Pat waited for you to do what you know you wanted to, she made up a few additional charges to ensure you got into the state prison system. Another associate got you sent here.”
A deep hollow feeling opened up inside me as she described how I’d been set up, actually chosen for this place. Pat must have had her eye on me for months, assessing me. I had been all but kidnapped and brought here to be a whore for the warden and everyone who worked for her. From what she said, I was also brought here to become a shemale.
The shocking thing was how excited I was by my growing sense of helplessness. I loved the feel of my new owner possessively, fondly stroked the bottom she just beat. The notion of being enslaved as a sissy gave me a hard-on that ached deeply. I moaned over and over while I sucked Andie’s huge clit. Almost as if she understood my feelings I felt the warden’s hand reached between the piss-soaked horse and my tummy and feel my cock. She laughed with delight.
“You’re hard as a rock at your predicament,” she said smugly, wiping her hand dry on my back. “You’re home and you don’t even know it yet. Officer Lewis, welcome our newest sissy to her new home.”
I heard the rasp of a zipper and the squish of lubricant. A thick slippery finger coated my asshole and easily pushed up inside. I moaned again. Then a big dick plowed up my asshole. Soon Andie and the CO found a rhythm, taking turns burying their cocks all the way into my mouth and asshole.
“Switch!” the warden called several minutes later.
Without hesitation I sucked the dick fresh from my asshole while Andie’s nine-inch cock starting fucking deep up inside my ass. The dominatrix warden got me more and more excited as she described how I would be fully transitioned into a shemale.
“That it… if you really want to be,” she concluded.
“Mmmm-hmmm! Mmmm-hmmm!” I whined in lust, meaning it with all my heart.
I was a nasty, dirty slut and I was glad!
The third time Andie went into my mouth she blew a deep glut of thick, tangy cum all over my tongue and teeth. Gently fucking my mouth with her softening boner, she gave me a kind smile and caressed my face. “You’re going to love it here,” she assured me. “I can tell.”
Then CO Lewis stuck his cock into my face and I dove on it happily, Andie’s words tantalizing my brain. I heard the warden call up the next CO to my ass, and I remembered there were still four more officers waiting to fuck, and I would be getting a good fill of prison guard cum.
SHUT UP
“No, the idea is dirty because that’s how you’ve been taught. As long as you follow the precautions I teach you, it’ll be safe. You must rise above you hang-ups, Petra.” I looked thoughtfully at her. “So you think I’m some kind of role model?”
“And I love you,” she gushed.
“Okay, then here’s a model for you. Get up on your knees, spread them wide, lay your chin on the mattress and stick your ass up in the air.”
I watched as she did so. She had such a sweet, round ass that would fill out nicely with hormones. Her pink and brown wrinkled asshole leaked cum and lube. I knelt behind her in between her parted legs, and spread those cheeks a bit more.
“What are you doing?” she asked.
“All kinds of cum and lube is coming out of your asshole. I’m going to clean it.”
“Oh, Rita!” she started to protest.
My hot tongue on her slippery, loose asshole cut off her complaints. She moaned softly while the commingled jizz of all six guards—Hayes and Grover had gotten it up again for Petra—coated my tongue. It was a heady blend of sweet, salty and masculine musk combined with the sugary flavor of KY Jelly and the earthy flavor of her asshole. I licked until her little hole glistened only with my spit.
“I love the taste of your ass, Petra,” I moaned. “I want more.”
I made my tongue stiff and thrust it deep past the relaxed ring of muscle, flooding my mouth with the taste of her asshole. I moaned with deep pleasure as if I tasted the sweetest candy in the world. After several minutes of this I pulled back and saw her cock was raging hard. Seized by inspiration I knelt next to her in the exact same position with my face on the mattress.
“Fuck my ass, Petra,” I coaxed her. “I’m still plenty lubed up. I want to feel my sweet baby’s cock fucking my tranny cunt!”
She required no further coaxing. She knelt between my legs and fed her dick into me. I groaned with abandon as she sank it deep into my rectal passage. I let her thrust in and out of me for a minute and then I got on all fours. I asked her to come around to my face. Not taking my eyes off of hers I took her cock into my mouth. I moaned in lust as I sucked the scent off her dick and got it all slippery again.
“Fuck me some more, baby!” I whined.
Panting with excitement she fed her dick back into my butthole and fucked me even harder. Again I asked her to pull out but this time I begged to suck it, begged for more from her. With relished I against sucked her clean and the wiggled my ass up in the air.
“Can you cum, baby?” I asked.
“Mmmmm, don’t know. Don’t care. All I want’s to fuck your mouth and your asshole and watch you do ass-to-mouth.”
“But I thought you loved me.”
“I do,” she said. “And you’re never so beautiful as when you’re doing that naughty thing.”
“So I guess we’re all done with feeling shame?”
“Yes, darling,” she said, smiling fondly, sheepishly.
“Okay the next—”
The door opened and Andie came in, looking harried. “Good news travels fast. The word is out we have two hot new girls here and already several high rolling regulars are on the way to try you girls out. The first one just got here” She pushed the button to make the false walls shoot up and disappear into the ceiling, revealing the mirrors, sex toys, bondage stuff and the closet doors. She plowed into one of the closets. “He likes schoolgirls,” she explained as she came out with two stripper schoolgirl costumes and white patent leather Mary Jane style shoes. “There’s special lingerie for the schoolgirl costumes in the bottom drawer over there.”
Andie helped us touch up our makeup, gave us high school girl hairstyles and told us all we needed to know as she got us ready. “He’s a really a big man. You’ll soon recognize him if you watch TV news at all. Call him, ‘Senator Fisk.’ He loves the recognition, since he knows he can trust all the girls here never to blab.”
She had us stand at the foot of our bed, facing the door. “I’ll just go get him.” She paused and then gave us a wide grin. “By the way, that was really hot sex just a little while ago. You looked so sexy.”
“How…?” I wondered.
“Camera mounted in the ceiling. Oh and, by the way, Petra you should listen to her. Shame is a useless emotion.”
Dressed in schoolgirl outfits with lacy white panties and bras, with white knee stockings and matching shoes, we stood at the edge of the bed. We held hands as we faced the door. Both of us wore exaggerated schoolgirl makeup with wide, cherry-red lips and big dots of rouge and heavily lined eyes. I gave her hand a squeeze and smiled reassuringly.
”Don’t worry, Petra. It’ll no different than fucking those guards. The only real difference is this man will be paying for it, so be sure to act extra sexy. Besides…” I leaned over and gently kissed her lips. “I love you and I’m here to protect you.”
“I love you too,” she replied with a smile, just as the door opened.
Just go kys you ugly old man.
More from SHEMALE PRISON:
I’d been charged with Prostitution, Indecent Exposure, Lewd Behavior, Sexual Battery, Oral Copulation and Sodomy. Most of it was bullshit, but when my parents heard the charges and saw Sergeant Pat lie about me on the stand at my preliminary hearing they disowned me. I was stuck with a public defender who couldn’t arrange a deal any better for me than six years, with the stipulation I wouldn’t have to register as a sex offender because no minor was involved nor was there any rape.
I was in the county jail for eleven days between the time I was dragged naked and still dripping cop piss to the booking window at the police station to the moment when they loaded me on the prison bus. My first night in County I was gang raped by five or six brutes, mostly white guys, while one big, muscled con watched. I tried to relax and enjoy it but they only wanted to cum and they weren’t very nice to me.
The next day the big guy, Greg, came up behind me in the shower and said if I wanted to avoid future rapes then I would become his bitch. He somehow saw right through me and asked my girl name. He liked my name “Petra” and promised to get me cosmetics and tight jailhouse clothing I could turn into a sexy outfit.
When I had told him there was no need to get me those things he said that I had better make myself look pretty for him. Later that second night, after lights out, he made me his. He fed me his veined, eight-inch dick and then fucked me so deeply but gently that I shot jizz all over my tummy. He called me “baby” as he fucked me and told me to call him “Daddy.” Since I had just lost my parents it was a comforting thing to me.
I actually cried as I boarded the bus, having fallen in love with “Daddy” Greg and his big sweet dick. Two hours later I filed off the bus with the chain of prisoners and into the Intake area of Gaviota State Prison, up north of Santa Barbara. After a strip search, a body cavity search, and a foul delousing spray, I went through a repeat of the same paperwork and crap I had at County. I was grouped with the other prisoners but an older but hot-looking woman “CO”—short for corrections officer—came up and told them to put me in a holding cell, that I was getting a special assignment.
Thinking they were going to put me someplace safe I sat in the eight-by-ten holding tank with the thin vinyl mattresses on the floor, and I waited for someone to take me to my new home. For the two-dozenth time since I’d been arrested, I cried bitter tears of self-pity. I was barely out of high school and in prison for kinky sex I never knew I had in me—much less love as much as I did—even getting gang fucked by those four cops. And now that my parents had disowned me I was totally alone in the world. I sobbed and sobbed.
I was so absorbed in my grief I barely heard he tank door open. I looked up to see who was entering—a pretty young… woman? She looked with gratitude at the CO who opened the door for her and thanked him. He was a handsome, tanned, buff man in his late twenties who looked like the surfer dudes I used to see at the beach. His nameplate read, “Perkins,” and he seemed to know this girl.
“I’m sorry to see this happen, Rita,” he said. “I don’t know why they’re putting you in here instead of general pop, but I’ll try to find out. And don’t worry, like I told Simone I’ll look out for you. Keep your chin up, okay?”
“Thank you again, Mr. Perkins.” She kissed him deeply and then stepped back so he could close and lock the steel door. She wobbled over to the bench against the wall and sat down heavily, clearly dazed. I could tell she’d been crying.
I assumed she had to be an especially pretty shemale to end up in a men’s prison. I’d seen photos and videos of transsexuals as pretty and young as her, but it was still fascinating to see one in the flesh. And what was she crying about? She and I were the only prisoners I’d seen crying this whole time since my arrest. For a moment I forgot my own troubles and sat down by her.
“You… your name’s Rita?” I asked in a low voice.
She got her tears under control and wiped her eyes before she nodded her head wearily. I decided against asking her what was wrong, other than the obvious thing of being a prisoner. I asked if she wanted a hug.
“Okay,” she said in a sweet feminine voice that made me marvel there was ever a boy under that soft, feminine skin.
She allowed me to hug her and after a moment she put her arms around me and hugged me back. It was the most tender thing I’d felt in weeks, and all of a sudden it reminded me that I might never get another hug from my parents ever again. That thought brought me right back to the look in their eyes in the courtroom: complete disgust and hostility as they turned and left the proceedings without ever looking back. I was totally alone in the world. Alone.
“Oh!” I blurted, tightening my grasp. Scalding tears and heaving sobs erupted from me with the force of that big earthquake that hit Los Angeles when I was just a little kid. I buried my face in Rita’s crisp, blue workshirt and cried my eyes out. To my relief she held me tight and stroked my back.
“Hey, now,” she said gently. “Who’s supposed to be comforting whom? It’s not that bad, baby. I promise you. I’ve been here before and you’ll be okay I promise.” She softly kissed my cheek a few times and quietly shushed me. “What’s your name, sweetie? How old are you?”
“I… I’m Petra—Peter. I-I’m eighteen,” I managed, exhausted of my sorrow.
She pulled back and gave me a warm smile. “Is Petra your girl name?”
“Uh-huh.”
“So, Petra… what’s making you so sad—besides the obvious?”
I recounted the whole story, my longtime fascination with girl things and later on shemales, my visits to the adult store and my arrest, and finally my parents giving up on me. “And now I’m here, all alone and not a friend in the world.”
She looked at me sweetly and said, “You have at least one friend now, Petra,” before she kissed my cheek near my mouth. “Do you like being called Petra?” she asked before she kissed near the other side of my mouth.
“I love being called Petra,” I sighed and then softly brought my lips full onto hers, opening my mouth and hoping.
My hopes were rewarded when she thrust her tongue into my mouth and crushed me to her boobs. We deep kissed for what seemed like an hour until she pulled back and looked me up and down, appraising me.
“I never really had a mentor,” she said. “I had born-women take me through my transition, get electrolysis for my face and body, get me my breast implants, and my Mistress is the one who found a doctor to give me special female hormones that feminize me but let me get hard. If anything the hormones make me shoot more cum than I ever had before. But there was no other sissy or shemale to guide me and teach me. Ever since I hoped to be a mentor to some girl… Would you like me to be your tranny mom?”
“Oh, yes, oh yes!” I moaned kissing her again. “I want you to be my mom!”
“Well, then, it’s time for Cocksucking 101,” she said with a grin. She quickly stripped off her clothes and sat naked on the bench with her knees spread wide. She looked at me with a salacious grin, her sorrow forgotten for the moment.
I must have Alzheimer’s because I don’t remember asking
shemale, a true force in and of herself when she was having sex. Even something I thought of as degrading as ass-to-mouth she made it look beautiful and wholesome. I wanted to be her so much!
Her plump red lips glistened with the black man’s cum—a foot-long wang that had been buried all the way up her ass only minutes ago. Now she was finishing off Officer Garrett, and by the ecstatic expression on his face she was milking his dick with her asshole. I decided right then and there I wanted her to teach me everything: how to suck a dick that big, to have control over my ass muscles, to be able to actually do ass-to-mouth and not get all queasy.
Shortly after the CO blew his load up my tranny lover’s ass. He pulled it out, but when Rita turned around to suck it clean the warden stopped her. She told Officer Garrett to get on his feet and to face me. A hollow feeling filled the pit of my stomach because I had a strong feeling what she was about to order me to do.
“Clean off his dick, Petra,” the warden commanded.
“N-no!” I blurted.
I said it with barely a whisper but she heard. In four long strides she stood before me. “On your knees, prisoner Hartmann.”
I dropped as fast as if someone had kicked my legs out. My knees stung as they hit the carpeted floor. I was afraid to look into her face. My balls tingled with fear. Gooseflesh covered my body.
“I don’t believe I heard you correctly,” she said icily.
“I made a mistake!” I cried. “I’m sorry! I’m sorry!” I stared at the carpet.
“May I speak, Mistress?” Rita asked urgently.
“Speak!” the warden barked. I could tell she was still looking down at me.
“She’s young and scared and never been in any situation like this. I promise to teach Petra her place. Please be lenient with her.”
Gratitude filled my heart and I fell a little more in love with her right then.
“Look at me, Petra,” Warden Fordham ordered.
I timidly raised my gaze to see her glaring down at me before she looked over to Rita, her expression softening.
“That’s very sweet of you, Rita. Considering how you’ve already more than proven your worth, I might otherwise be willing to consider your request. However I think you’re a smart enough girl to know why I can’t allow you to teach this fishie her place. Can you tell me why?”
“Because it’s your job, Mistress.”
“Rita,” the warden said with a smile, “that’s three times today you’ve pleased me, so I will be a little bit more lenient than I was planning.” She looked back at me. “I gave you an order, Petra. Go suck his cock.”
I knelt in front of Officer Garrett. His dick was still hard. It glistened with lube and cum. Fortunately, it didn’t look dirty but it still smelled faintly of ass. I looked past him and into Rita’s eyes and saw her looking back at me so tenderly it was easy to imagine she did love me, which made what I was about to do so much easier.
I gave the CO’s cock a long lick. It tasted earthy and pungent, a little sharp. It was the taste from deep up inside my darling Rita. Suddenly that very thought turned me on like I never imagined it could, but only because it was the taste of her ass. Before I could think a moment longer I lowered my mouth onto his dick and began sucking greedily like a little kid with a popsicle on a hot day.
If it wasn’t Rita’s ass—my only true love in the world—I’d have been repulsed. Then I realized this would be a way to show her how much I loved her. I sucked and sucked and made mewling sounds of pleasure. After two minutes the warden ordered me to stop.
“You love the taste of Rita, don’t you?”
“Yes, Mistress!” I enthused. “I love everything about her.”
“You want to be just like her, don’t you?”
“Yes, Mistress!”
“Then you must be properly trained. Officer Hayes and Captain Grover, get the horse and bring it here.”
For a few seconds I imagined them bringing in an actual horse but the two guards went into one of the doors on the wall, which turned out to be walk-in closets. They brought out a big sawhorse-type piece of furniture with a wide padded top and legs. Each of the four legs had thick eyehooks set into them with padded leather cuffs attached to each with a rope that tied off at the bottom of the leg.
“Andie, bring the tarp,” she commanded.
One minute later our shemale guide had spread a ten-by-ten waterproof tarp. The guards set the horse in the middle of the tarp. Hayes looked me up and down and shortened the length of the top with some levers and locked it into place. All of a sudden I was frightened, realizing I was to be tied down, completely helpless. The tarp made me even more nervous.
Following the warden’s orders I lay across the top and draped my arms down the front legs. My chin rested perfectly on the far end of the horse. My legs were spread wide and cuffs attached at ankles; then the ropes were pulled until my legs were tied fully to the back legs of the bondage horse. The same was done with my arms down the front legs. I could barely move a muscle and I was fully exposed: my balls, my spread asscheeks and my mouth. My dick was trapped under my body between my tummy and the horse’s padded top.
“Mistress?” Rita asked. “Another question please?”
She looked at my lover with a charitable smile. “Let me guess: you want to be with her during her chastisement. Hold her hand and look into her eyes. Was that it?”
“My Mistress knows her girl so well,” Rita replied. It seemed to me that she was following some kind of ritual or etiquette that had to do with all this bondage and dominance and stuff.
“Again, very kind of you, but she must face her first discipline all alone. She can’t learn her lesson if it is shared. I will permit you to comfort her afterward.”
Mistress Fordham had circled behind me as she spoke. Out of nowhere came a cruel whistle of air as she swung the cane. The sound it made on my skin was oddly quiet, like a soft thud, but then my asscheeks felt scorched, like a red-hot poker had been pulled out of a fire and laid across my ass. I screamed. If I had not been tied down tightly to the “horse” I would have not been able to help jumping up.
Electric shocks fired down my legs and up my spine. What just happened to me was only beginning to register when that terrifying cut through the air repeated, and a new burning line crossed my ass. I was dizzy from the enormity of the pain. Another fell. And another. And another. The stripes of agony all added up to make me dizzy and weak. And yet my cock still tingled, halfway erect.
Without warning I felt warmness, a wet warmness under my stomach. I realized why the tarp had been put onto the floor: I had just pissed myself. In between the violent parting of the air and the blows I heard my pee dripping onto the rubberized canvas. The warden must have heard it too because she stopped beating me and tossed the cane onto her desk. She crouched down and looked into my eyes.
“Do you now grasp what punishment is? The consequences of disobedience?”
“Yes, Mistress,” I sobbed, half in pain and half in relief it might be over.
“Now grasp this: I was holding back seventy-five percent of what I can dish out. I can break your skin with that cane; I can open your asscheeks up so badly the liquid trickling down your legs will be your own blood.” She turned her back, walked to the edge of her desk and sat. “Rita, you may comfort her now.”
Naked and sweaty, Rita knelt in front of me and took my bound hands in hers. She looked into my eyes and whispered it was all going to be okay. She started planting soft kisses. In between those kisses she assured me I’d never have to feel that again as long as I obeyed without question, as long as I strove to please my owners and those I served, and as long I always kept getting better at being a sissy and a whore.
“Okay, that’s enough. Get out of there, Rita. It’s time to see if she’s even one tenth as good as you at sucking and fucking.” She looked to the trustee. “Andie, you’ve been such a good girl this week.”
“Thank you, Ma’am,” the stunning brunette said with a curtsy.
“Why don’t you be the first of our happy home to sample the girl’s cocksucking?”
“Shall a girl disrobe completely, Ma’am?” Andie asked.
“By all means. Let everyone enjoy your sexy body.”
The trustee kicked off her loafers, revealing some kind of hosiery beneath her institutional uniform. In a slow and deliberate striptease, Andie removed her prisoner top to reveal an expensive, lacy demi bra that thrust large C-cup tits with big, erect nipples out for all to see. Then came off her denims to reveal a matching garter belt and sheer, tan stockings. A big cock bulged at her lacy, French-cut panties. With sparkling brown eyes she looked hungrily at me. She sashayed up to me where I was still tied down to the horse; my mouth was level with her crotch. She was so very beautiful—every bit as much as darling Rita.
“You’re such a pretty sissy,” she said. “Eighteen and already so very feminine.” She eased down her panties a couple inches and freed up a cock maybe nine inches long and getting harder by the moment. “Suck it, baby.”
Eagerly I closed my mouth around her tranny boner, not caring how slutty my hungry slurping noises made me sound. I loved the feel of her firm, tanned dickflesh between my lips, pulsating in my mouth, the hot plump head sliding in and out. I strained to move my head forward, to try to take her into the back of my throat.
“It looks like she’s trying to deepthroat me, Ma’am,” Andie said. “She has true potential indeed… Do you think you should tell her?”
The warden chuckled darkly. “I think it would put her even more in the proper frame of mind.” I sensed the warden moving next to me, felt her hand softly stroking my ass she’d so severely whipped. “It was no accident you were arrested in that porno shop. It’s one of a dozen such places our… associates have under surveillance. For the most part they’re conducting their normal vice operations, but certain members, such as that sergeant you knew as Pat, are always on the lookout for us. They’re looking out for sissies like you who have the potential to become shemales like Rita or our lovely Andie you’re so eagerly giving a blowjob to. Pat waited for you to do what you know you wanted to, she made up a few additional charges to ensure you got into the state prison system. Another associate got you sent here.”
A deep hollow feeling opened up inside me as she described how I’d been set up, actually chosen for this place. Pat must have had her eye on me for months, assessing me. I had been all but kidnapped and brought here to be a whore for the warden and everyone who worked for her. From what she said, I was also brought here to become a shemale.
The shocking thing was how excited I was by my growing sense of helplessness. I loved the feel of my new owner possessively, fondly stroked the bottom she just beat. The notion of being enslaved as a sissy gave me a hard-on that ached deeply. I moaned over and over while I sucked Andie’s huge clit. Almost as if she understood my feelings I felt the warden’s hand reached between the piss-soaked horse and my tummy and feel my cock. She laughed with delight.
“You’re hard as a rock at your predicament,” she said smugly, wiping her hand dry on my back. “You’re home and you don’t even know it yet. Officer Lewis, welcome our newest sissy to her new home.”
I heard the rasp of a zipper and the squish of lubricant. A thick slippery finger coated my asshole and easily pushed up inside. I moaned again. Then a big dick plowed up my asshole. Soon Andie and the CO found a rhythm, taking turns burying their cocks all the way into my mouth and asshole.
“Switch!” the warden called several minutes later.
Without hesitation I sucked the dick fresh from my asshole while Andie’s nine-inch cock starting fucking deep up inside my ass. The dominatrix warden got me more and more excited as she described how I would be fully transitioned into a shemale.
“That it… if you really want to be,” she concluded.
“Mmmm-hmmm! Mmmm-hmmm!” I whined in lust, meaning it with all my heart.
I was a nasty, dirty slut and I was glad!
The third time Andie went into my mouth she blew a deep glut of thick, tangy cum all over my tongue and teeth. Gently fucking my mouth with her softening boner, she gave me a kind smile and caressed my face. “You’re going to love it here,” she assured me. “I can tell.”
Then CO Lewis stuck his cock into my face and I dove on it happily, Andie’s words tantalizing my brain. I he
shemale, a true force in and of herself when she was having sex. Even something I thought of as degrading as ass-to-mouth she made it look beautiful and wholesome. I wanted to be her so much!
Her plump red lips glistened with the black man’s cum—a foot-long wang that had been buried all the way up her ass only minutes ago. Now she was finishing off Officer Garrett, and by the ecstatic expression on his face she was milking his dick with her asshole. I decided right then and there I wanted her to teach me everything: how to suck a dick that big, to have control over my ass muscles, to be able to actually do ass-to-mouth and not get all queasy.
Shortly after the CO blew his load up my tranny lover’s ass. He pulled it out, but when Rita turned around to suck it clean the warden stopped her. She told Officer Garrett to get on his feet and to face me. A hollow feeling filled the pit of my stomach because I had a strong feeling what she was about to order me to do.
“Clean off his dick, Petra,” the warden commanded.
“N-no!” I blurted.
I said it with barely a whisper but she heard. In four long strides she stood before me. “On your knees, prisoner Hartmann.”
I dropped as fast as if someone had kicked my legs out. My knees stung as they hit the carpeted floor. I was afraid to look into her face. My balls tingled with fear. Gooseflesh covered my body.
“I don’t believe I heard you correctly,” she said icily.
“I made a mistake!” I cried. “I’m sorry! I’m sorry!” I stared at the carpet.
“May I speak, Mistress?” Rita asked urgently.
“Speak!” the warden barked. I could tell she was still looking down at me.
“She’s young and scared and never been in any situation like this. I promise to teach Petra her place. Please be lenient with her.”
Gratitude filled my heart and I fell a little more in love with her right then.
“Look at me, Petra,” Warden Fordham ordered.
I timidly raised my gaze to see her glaring down at me before she looked over to Rita, her expression softening.
“That’s very sweet of you, Rita. Considering how you’ve already more than proven your worth, I might otherwise be willing to consider your request. However I think you’re a smart enough girl to know why I can’t allow you to teach this fishie her place. Can you tell me why?”
“Because it’s your job, Mistress.”
“Rita,” the warden said with a smile, “that’s three times today you’ve pleased me, so I will be a little bit more lenient than I was planning.” She looked back at me. “I gave you an order, Petra. Go suck his cock.”
I knelt in front of Officer Garrett. His dick was still hard. It glistened with lube and cum. Fortunately, it didn’t look dirty but it still smelled faintly of ass. I looked past him and into Rita’s eyes and saw her looking back at me so tenderly it was easy to imagine she did love me, which made what I was about to do so much easier.
I gave the CO’s cock a long lick. It tasted earthy and pungent, a little sharp. It was the taste from deep up inside my darling Rita. Suddenly that very thought turned me on like I never imagined it could, but only because it was the taste of her ass. Before I could think a moment longer I lowered my mouth onto his dick and began sucking greedily like a little kid with a popsicle on a hot day.
If it wasn’t Rita’s ass—my only true love in the world—I’d have been repulsed. Then I realized this would be a way to show her how much I loved her. I sucked and sucked and made mewling sounds of pleasure. After two minutes the warden ordered me to stop.
“You love the taste of Rita, don’t you?”
“Yes, Mistress!” I enthused. “I love everything about her.”
“You want to be just like her, don’t you?”
“Yes, Mistress!”
“Then you must be properly trained. Officer Hayes and Captain Grover, get the horse and bring it here.”
For a few seconds I imagined them bringing in an actual horse but the two guards went into one of the doors on the wall, which turned out to be walk-in closets. They brought out a big sawhorse-type piece of furniture with a wide padded top and legs. Each of the four legs had thick eyehooks set into them with padded leather cuffs attached to each with a rope that tied off at the bottom of the leg.
“Andie, bring the tarp,” she commanded.
One minute later our shemale guide had spread a ten-by-ten waterproof tarp. The guards set the horse in the middle of the tarp. Hayes looked me up and down and shortened the length of the top with some levers and locked it into place. All of a sudden I was frightened, realizing I was to be tied down, completely helpless. The tarp made me even more nervous.
Following the warden’s orders I lay across the top and draped my arms down the front legs. My chin rested perfectly on the far end of the horse. My legs were spread wide and cuffs attached at ankles; then the ropes were pulled until my legs were tied fully to the back legs of the bondage horse. The same was done with my arms down the front legs. I could barely move a muscle and I was fully exposed: my balls, my spread asscheeks and my mouth. My dick was trapped under my body between my tummy and the horse’s padded top.
“Mistress?” Rita asked. “Another question please?”
She looked at my lover with a charitable smile. “Let me guess: you want to be with her during her chastisement. Hold her hand and look into her eyes. Was that it?”
“My Mistress knows her girl so well,” Rita replied. It seemed to me that she was following some kind of ritual or etiquette that had to do with all this bondage and dominance and stuff.
“Again, very kind of you, but she must face her first discipline all alone. She can’t learn her lesson if it is shared. I will permit you to comfort her afterward.”
Mistress Fordham had circled behind me as she spoke. Out of nowhere came a cruel whistle of air as she swung the cane. The sound it made on my skin was oddly quiet, like a soft thud, but then my asscheeks felt scorched, like a red-hot poker had been pulled out of a fire and laid across my ass. I screamed. If I had not been tied down tightly to the “horse” I would have not been able to help jumping up.
Electric shocks fired down my legs and up my spine. What just happened to me was only beginning to register when that terrifying cut through the air repeated, and a new burning line crossed my ass. I was dizzy from the enormity of the pain. Another fell. And another. And another. The stripes of agony all added up to make me dizzy and weak. And yet my cock still tingled, halfway erect.
Without warning I felt warmness, a wet warmness under my stomach. I realized why the tarp had been put onto the floor: I had just pissed myself. In between the violent parting of the air and the blows I heard my pee dripping onto the rubberized canvas. The warden must have heard it too because she stopped beating me and tossed the cane onto her desk. She crouched down and looked into my eyes.
“Do you now grasp what punishment is? The consequences of disobedience?”
“Yes, Mistress,” I sobbed, half in pain and half in relief it might be over.
“Now grasp this: I was holding back seventy-five percent of what I can dish out. I can break your skin with that cane; I can open your asscheeks up so badly the liquid trickling down your legs will be your own blood.” She turned her back, walked to the edge of her desk and sat. “Rita, you may comfort her now.”
Naked and sweaty, Rita knelt in front of me and took my bound hands in hers. She looked into my eyes and whispered it was all going to be okay. She started planting soft kisses. In between those kisses she assured me I’d never have to feel that again as long as I obeyed without question, as long as I strove to please my owners and those I served, and as long I always kept getting better at being a sissy and a whore.
“Okay, that’s enough. Get out of there, Rita. It’s time to see if she’s even one tenth as good as you at sucking and fucking.” She looked to the trustee. “Andie, you’ve been such a good girl this week.”
“Thank you, Ma’am,” the stunning brunette said with a curtsy.
“Why don’t you be the first of our happy home to sample the girl’s cocksucking?”
“Shall a girl disrobe completely, Ma’am?” Andie asked.
“By all means. Let everyone enjoy your sexy body.”
The trustee kicked off her loafers, revealing some kind of hosiery beneath her institutional uniform. In a slow and deliberate striptease, Andie removed her prisoner top to reveal an expensive, lacy demi bra that thrust large C-cup tits with big, erect nipples out for all to see. Then came off her denims to reveal a matching garter belt and sheer, tan stockings. A big cock bulged at her lacy, French-cut panties. With sparkling brown eyes she looked hungrily at me. She sashayed up to me where I was still tied down to the horse; my mouth was level with her crotch. She was so very beautiful—every bit as much as darling Rita.
“You’re such a pretty sissy,” she said. “Eighteen and already so very feminine.” She eased down her panties a couple inches and freed up a cock maybe nine inches long and getting harder by the moment. “Suck it, baby.”
Eagerly I closed my mouth around her tranny boner, not caring how slutty my hungry slurping noises made me sound. I loved the feel of her firm, tanned dickflesh between my lips, pulsating in my mouth, the hot plump head sliding in and out. I strained to move my head forward, to try to take her into the back of my throat.
“It looks like she’s trying to deepthroat me, Ma’am,” Andie said. “She has true potential indeed… Do you think you should tell her?”
The warden chuckled darkly. “I think it would put her even more in the proper frame of mind.” I sensed the warden moving next to me, felt her hand softly stroking my ass she’d so severely whipped. “It was no accident you were arrested in that porno shop. It’s one of a dozen such places our… associates have under surveillance. For the most part they’re conducting their normal vice operations, but certain members, such as that sergeant you knew as Pat, are always on the lookout for us. They’re looking out for sissies like you who have the potential to become shemales like Rita or our lovely Andie you’re so eagerly giving a blowjob to. Pat waited for you to do what you know you wanted to, she made up a few additional charges to ensure you got into the state prison system. Another associate got you sent here.”
A deep hollow feeling opened up inside me as she described how I’d been set up, actually chosen for this place. Pat must have had her eye on me for months, assessing me. I had been all but kidnapped and brought here to be a whore for the warden and everyone who worked for her. From what she said, I was also brought here to become a shemale.
The shocking thing was how excited I was by my growing sense of helplessness. I loved the feel of my new owner possessively, fondly stroked the bottom she just beat. The notion of being enslaved as a sissy gave me a hard-on that ached deeply. I moaned over and over while I sucked Andie’s huge clit. Almost as if she understood my feelings I felt the warden’s hand reached between the piss-soaked horse and my tummy and feel my cock. She laughed with delight.
“You’re hard as a rock at your predicament,” she said smugly, wiping her hand dry on my back. “You’re home and you don’t even know it yet. Officer Lewis, welcome our newest sissy to her new home.”
I heard the rasp of a zipper and the squish of lubricant. A thick slippery finger coated my asshole and easily pushed up inside. I moaned again. Then a big dick plowed up my asshole. Soon Andie and the CO found a rhythm, taking turns burying their cocks all the way into my mouth and asshole.
“Switch!” the warden called several minutes later.
Without hesitation I sucked the dick fresh from my asshole while Andie’s nine-inch cock starting fucking deep up inside my ass. The dominatrix warden got me more and more excited as she described how I would be fully transitioned into a shemale.
“That it… if you really want to be,” she concluded.
“Mmmm-hmmm! Mmmm-hmmm!” I whined in lust, meaning it with all my heart.
I was a nasty, dirty slut and I was glad!
The third time Andie went into my mouth she blew a deep glut of thick, tangy cum all over my tongue and teeth. Gently fucking my mouth with her softening boner, she gave me a kind smile and caressed my face. “You’re going to love it here,” she assured me. “I can tell.”
Then CO Lewis stuck his cock into my face and I dove on it happily, Andie’s words tantalizing my brain. I he
Fuck off sam hill
How Petra ended up in an all shemale/sissy prison…
From SHEMALE PRISON, Chapter 1:
—
Halfway down was booth 18, the one showing my movie. Before I even reached its door I knew I would go inside. Moments later I was sitting on a plastic bench in an even dimmer cubicle that smelled of cum, which fortunately was on the floor instead of the bench. There was just enough light to find the narrow shelf to set my tokens and the coin box that ran the video and made it play on the twenty-inch screen. I fed in a token right away.
The video picked up somewhere past the beginning, starting up in a sex scene with the young, light-skinned Latina tranny on the cover sucking on a nine-inch shemale cock while a black guy fucked her ass doggy-style with what looked like a ten inches of thick dick. Globs of white stickiness covered her face and large silicone tits. I couldn’t take my eyes off the cock in her mouth. My boner strained at my pants.
I didn’t think of who might come in or anything; I immediately took my dick out and started whacking off. Within two minutes I was ready to cum but then I looked at that stack of tokens and realized I could draw this out. Besides, part of me desperately wanted someone to come in here. A moment later, maybe three minutes from starting the loop, the video shut off and returned the booth to partial darkness.
I fed in a new quarter and was treated to the sex scene continuing. The shemale pulled out of the young tranny’s mouth and spattered jizz all over her lips and tongue, which she lapped up like a treat. I wondered what it must be like to do that. Would I get a chance to find out tonight? I glanced at the door and realized I had instinctually pushed in the button to lock it. I took a deep breath and gave the knob a slight twist. The click of it unlocking was loud, even louder than the film. Fifteen seconds later the knob turned and she walked in.
She was about six-foot but slender. She wore a hooker dress that showed off long, smooth legs and smallish feet in high heels. I don’t know if it was really a she, as in a shemale, or just a really beautiful crossdresser, but I had seen her in the store and seen her go back here many times. All the clerks seemed to know her; they all called her Kim. Her voice was androgynous, like some of those raspy actresses in Hollywood. Right now she looked at me with a desire that almost unnerved me.
“I’d hoped you’d come back here someday,” she said.
“You did?” I asked nervously.
“You’re one of the most beautiful boys ever to come in this store,” she cooed, stroking my face with a soft, feminine hand. “I bet you’d make an even more beautiful girl.”
I shivered with lust at hearing that. She looked down to my throbbing cock still in my hand, then to the video where the young shemale was now sucking a new cock.
“Is that what you want?” she asked.
I bit my lip and nodded my head, as shaky as I was excited.
“Do you want to do what she’s doing? Sucking a shemale dick?”
I nodded again, dizzy with anticipation.
“You have to say it, beautiful.”
“I want to suck a shemale’s dick,” I moaned.
Kim smiled at me. “I’m not exactly a shemale,” she said.
“I don’t care.” I leaned back as she straddled me and pulled up the hem. At least eight inches of cock strained at see-through, French cut white panties. “Oh my god,” I moaned, my mouth hanging open and my lower lip quivering in anticipation.
“Put the rest of the tokens into the box,” she said. “That will give us half an hour of light and a sexy soundtrack.”
With trembling hands I fed the remaining tokens into the coin box. Kim looked down into my eyes with a gentle smile as she pulled down the hem of her panties to expose a cock as big as the one the young tranny had been sucking. With no delay I opened wide and took it into my mouth.
The flesh of her dick was so very soft and delicate yet so very hot. I could actually feel the blood pumping through it with my lips and tongue. As salty-sweet flavor filled my mouth that I was afraid might gag me but instead I swallowed greedily. I was drinking down her pre-ejaculate and loving it as much as I was the feel of her big sissy tool in my mouth.
I’d watched enough cocks being sucked in my small porn video collection to know what to do, but I’d never given any thought to what this moment would really be like. I had been afraid I’d be grossed out. Instead my worst fear had been realized: I loved it. I was a natural born cocksucker, and I knew I was definitely going to be coming to places like this for the rest of my life.
“Oh, honey,” Kim moaned. “That feels so good! You’re such a good baby!”
Spurred by her words I took her dick as deep into my mouth as I could. I was so high on giving this blowjob I was barely aware that someone else had just come in. I stiffened but then I heard Kim greet whoever it was as “Tina.” A moment later a hot, wet mouth closed over my boner. It was a good thing my mouth was full of Kim’s erection because my groan would have been heard all the way out to the cash register!
I felt large, soft hands with long nails expertly unbutton my pants and tug them down, followed by my tight jockey shorts. Somehow Tina managed to keep sucking my cock while she removed my shoes, socks and everything else until I was naked from the waist down. Meanwhile I sucked Kim with such a passion I never knew I had, praying she’d fill my mouth with her cum. Then the door opened again.
I looked up to see two guys standing to either side of me, their dicks jutting out their zippers. They guided my hands to their boners. Now I was sucking a sissy’s big cock, getting a blowjob and jacking off two guys. One of them took off my shirt, making me completely naked, which I was ready for. I wanted to feel as sexy as possible. If there had been lingerie to change me into I’d have done it.
I eagerly put myself into their hands, so that when Kim said she was going to fuck me I allowed myself to be fully stripped and bent over the shelf that’d held the video tokens. A clean-shaven face burrowed between my spread asscheeks and licked my asshole while Kim unwrapped a condom and rolled it over her boner, then squeezed a foil envelope of lube on it.
“You want me to fully make you a sissy girl?” Kim asked me.
“Oh please, yes!” I moaned. “Fuck me!”
She started with one lubed finger, and then added another. I couldn’t believe how easily my ass opened up to her. By the time she had in a third finger I was throwing my ass back against her hand. I begged her to fuck me.
Tina, who I could see was a well-hung black shemale had leaned against the shelf in front of me and guided my hands around her waist, putting her uncut, foot-long tool right in my face. While I waited for Kim to penetrate me, I sucked on Tina’s ebony cock. It was the most beautiful thing I’d ever seen and I wanted to suck down every drop of her cum.
“Little sister is an eager cocksucker,” Tina sighed. “What a natural!”
I started to moan my thanks when Kim slowly slid her entire big dick all the way into me. I groaned like I’d never felt anything so pleasurable. Meanwhile one of the guys took over sucking my thrumming cock. The other one rubbed his dick all over my face, leaving drips of precum. Just then another guy entered and started jacking off on the other side of my face.
Part of me wondered if they’d all been hanging out and waiting for an orgy to get started in one of the booths but I was too horny and overwhelmed with erotic rapture to give it much thought. So many firsts all at once, starting with Kim’s massive boner filling me up and setting my asshole tingling with an exposed, vulnerable, dirty feeling that made me feel like a big slut because I loved it so much. I wanted to get fucked up my ass every day and every night forever!
Tina’s made the second dick I’d ever had in my mouth. Her tranny cock oozed salty precum that made me want to taste the real thing. Like Kim’s cock, the flesh was so delicate and yet hot and hard at the same time. Finally, I’d never gotten a blowjob, either. The guy sucking me off had his hand cupped around my balls. Whenever I felt like I was going to spurt into his mouth he pulled off me and tightened his thumb and forefinger around the base of my shaft, stopping me from cumming. Then he began sucking again.
Soft little moans came from Tina’s mouth. “I don’t know what’s sexier: watching this baby sissy love sucking my dick or love getting fucked.”
“What’s sexy to me is I’m pretty sure she’s a cherry,” Kim panted, fucking me harder to my delight.
I moaned deeply and begged her to fuck me harder still.
“Is that right, honey?” Tina said. “Are you a virgin?”
I looked up into her face as I sucked her cock and nodded.
“Oh fuck that’s so sexy. It… Damn, all of a sudden I’m close to popping. Anyone wanna cum in her mouth first?”
“Go for it, girlfriend,” Kim urged.
“Open your mouth wide, darling,” Tina said kindly.
I did as she asked, my eyes squeezed shut but my lips parted wide. I was a little afraid of how it was taste but most of me was thrilled I was going to be a cum-drinking sissy like all the porn I’d watched.
“Open your eyes and look at me, darling,” Tina coaxed.
I looked and saw her big, spit-shiny brown dick pumping through her soft fist, angry purple head dripping clear, sticky fluid pointed at my tongue. It looked so sexy!
“You’ve never tasted cum before, either.” She said it as a statement.
“No,” I admitted in a tiny voice. “I haven’t. Not even my own.”
“Oh, fuck, that’s hot!” Tina enthused. “Her mouth is cherry too! I… I… oh fuck!”
A thick white, sticky cord arced from her cockhead and into my mouth, splashing onto my tongue and front teeth, and then another until shat felt like a shotglass full over cum was in my mouth. Without thinking I swallowed it just in time to catch a smaller spurt that partly coated my lips.
Tina’s spunk was tangy-salty, almost sweet. I loved the feel of it on my tongue. Instead of swallowing I pushed it around my mouth with my tongue, spreading it on my lips and teeth while I looked up at the grinning shemale with adoring eyes. That was when I heard the guy to my right groan.
“Gonna cum!” he gasped.
I turned my open mouth to his direction while Tina wiped the remaining drops of her cum on my cheek. The guy on my other side began beating off furiously. Hot gasps and moans tore from my mouth as Kim battered my asshole with her huge dick and the guy sucking my dick went for broke, not trying prolong my orgasm any more. I was barely conscious of the guy who’d been on my left stand next to the guy who was about to blow his load into my open mouth.
A tiny part of me was aghast at what I had put myself into— having public sex where anybody could walk in and catch me, swallowing strangers’ cum and eagerly preparing to drink down more semen, while I was getting a blowjob. This was crazy! This was dangerous! Yet I was way too horny to care.
Both of the men came at the same time, their thick hot cum splattering all over my lips and nose and cheeks and my chin, covering my tongue with bittersweet, salty jizz that I swallowed without thinking. I cried out as my own throbbing dick pumped my load into the man sucking me off, on fire with the feeling of sissy Kim’s dick sliding in and out of my asshole.
“Get out of the way, guys,” Kim panted. “One more load for our little slut. Sit on the bench, honey.” She pulled out of my ass.
My asshole twitching and aching exquisitely, my cock tingling and my balls throbbing, I plopped into the seat. I looked up into Kim’s eyes as she stripped off the condom and stuck her boner into my face. I licked the biggest globs of cum from my lips and took her re-pink glistening boner in my mouth, sucking it hard. Moments later I was rewarded with a deep groan and spunk flooding my mouth. Kim pulled back just far enough to give her last thick full spurt onto my lips.
“Welcome to the sissy life, Petra,” Kim said. She grinned at me with a sad smile, while she tucked her dick back into her panties.
All of a sudden I realized she used the name that Pat out in the store had called me. All of a sudden I got a sinking feeling. “Wh-what did you say?”
Tina and the two guys had stowed their cocks into their clothes, leaving me the only one in the booth naked—and dripping cum. When Kim coughed exaggeratedly toward the door, that’s when I knew I was fucked. There was no point in trying to put my clothes on.
Five seconds later, four uniformed cops rushed in. I’m guessing they sent in so many in case I resisted, but one cop was able to put my hands behind and cuff me as I knelt in the middle of the booth. I looked numbly up at the four grinning officers and allowed them to set me on my feet.
Stark naked and streaked with jizz I was marched out of the store while all of the patrons stared at me, some snickering and some leering and saying how they’d fuck me if they got a chance. What worried me was being seen this way out on the sidewalk, being led naked and degraded out of a porno shop.
I was relieved I hadn’t far to go as a paddy wagon was parked right outside. There was a creak as the back door opened. The cops led me to the door. I heard the click-clack of high heels coming up behind us, so I turned my head to see Kim following. A hunky, young cop poked his head out of the back of the paddy wagon and smiled at me. Seeing Kim he reached out and handed her a hundred dollar bill. She took it and walked away. I had been set up.
The young cop pulled me into the back of the wagon where three other cops sat on the benches, stroking erect dicks that jutted out of their uniforms. Standing in the very back of the wagon was Pat, who now wore a police uniform with sergeant stripes. She looked at me with approval as I stood before her naked and covered with jism.
“Petra, I knew you wouldn’t disappoint me,” she purred, making her way to me.
“P-Pat?” I gasped.
“Sergeant Patricia Dunston,” she said. “And your name is now Petra.” She nodded to the other cops. “Men, let’s show this sissy what we do with a sex offender.”
For half an hour the four male cops took turns fucking my asshole and my mouth, pumping more cum into my asshole and down my throat. All the while Pat had taken off her police trousers and was fingering her clit, bringing herself to several orgasms by the time her cops were done fucking me.
It looks like it says 5’11” in the panels and 145lbs in the 7th panel…
Kik: ValianTtD
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Hello, I looked in deviant art an alternative and sensual story of serleena of MIB and it’s a good story. https://www.deviantart.com/paladingear8/art/Serleena-Succeeds-Alternative-Story-805309445 its the best and detailed story that i read. And i thought if perhaps it deserves a comic book.
holy shit please do more of these characters
GOD DAMN.
Red Head Jack is 6 FUCKIN ’11!
She is a GIANT.
Like, Shaq is only 2 inches taller then her.
She could square up on Shaq without a sweat!
DAMN
Genio sos dios dibujando
jah
Really good. Girl in glass window is hot! Do you do request?
Anyone in Cornelius want to have fun?
Nice machine head reference
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stop being horny and do your homework
Oi, your too young to be doing this to yourself.
I hope some sick pedo gets stung
Your not fooling anyone Cris Hanson.
Not, Chris Handsome. I am actually here to FUCK
A. Love the brown haired girl, cute and hot asf, and lil ass zuck is dope
you added the zuck in, thats the best, and anal with a phone head thats cool too
YOOOOO MACHINE HEAD IS AMAZINGGGG
Damn those tattoos are very good. Would love to see a image of the lesbian tattoos drawn that were drawn the inmate
Red head girl looks so fucking awesome
Would be hot seeing her being abused by the guards.
What is the prison girl’s name?
Amazing as Always shad. You should do more of these girls
Is there a version without Zuccy and the prison guards
Is there a version without Zuccy and the prison guards?
Where’s the one without Zuccy and the prison guards?
How is she 6’11” but only weighs 195 pounds
6’11”?? Jesus Christ
MORE SCAT CARTOONS PLEASE
downvote this
Love your work but the girls faces still look similar even if the eye color is different
Hey Shad! Fucking nice as always. What are their names?
Jolyne
Mark the Facebook CEO got a fat ass.
This is actually very well done
I’d say it’s the best comic piece you’d done so far Artistically that is;)
Z U C C
Der Rücken ist so verdammt gut geworde
That Mark Zucc’d fucking killed me
She looks like max claufield
Make a dick girl version of both of them shad
be honest, you just wanted a reason to draw all those tattoos
i wonder what it sounds like on the other side, when she had the phone in her ass
I really love how you have evolved your drawings over the years and still kept your original style. Thanks Shäd.
i thought would guard fall off his chair in last frame
This is so fucking good. Thanks Shad
Look like Quiet? 🤷♂️🤷♂️🤷♂️🙄. Very sexy story 🤷♂️
MORE PRISON GIRLS PLEASE!!!!
A 6’11” person that only weighs 195lbs would actually look grossly thin.
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She has blue eyes in all the other panels, on her inmate card, but on the final one she has brown eyes…
THANK YOU! I thought that was weird too
Haha! Great expressions on the last panel
Your art fucking sucks now man what happened
Shad I been looking at your art for years dude and this might be the most impressive piece yet. The detailing on those tats plus the perfect placements in every frame. This is why im proud to be a fan
Very hot pls do a followup comic of this
Her being 6’11 is a really big turn on for me
More of prison girl
The tatts remind me of OG Shad. This shit is pretty nice too though
YES MORE OF THIS SHAD!! LESS FAGGOT DICK SHIT
Dude just let him do the things he wants to do
Wish he’d just make both versions of most pictures tbh. Prolly a lot less work than the whole drawing is.
Lesbians are boring but keep making what you wanna make shad!
Hey can you do a comic of joe biden and his granddaughter? She is 19 by the way, so perfectly legal.
wow that kiss.
I think he can battle Trump for who bang harder their own daughter/granddaughter.
The winner will be POTUS, forget the votes, democracy is forged anyway.
Didn’t figure Shadbase to be a Machine head follower.
These correctional patches are pretty fucking great. Might need to get this in a decal.
Shad you’re a fucking idiot, the knuckle tattoos are backwards and upside down. Knuckle tattoos are designed so when you make two fists and put them side by side it reads a word. So all the letters should be flipped upside down, and the D for degenerate should be on the pinky and read left to right. What’s even more retarded is you put a letter on the knuckles of the thumb, so you wouldn’t even so the letters when you do the fist show off combo
get your life together you trap loving, nigger cock sucking, bad vidya playing asshole
Zuckerberg in the background lmao
I enjoyed this thank you shad
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as lewd as this is
i love it when you do the little romantic aspects like this,
then pair with extreme lewdity
but seriously speaking, your good at it when you do it. please more like this, maybe continue these characters
I love the orginal charaters! I want to see more of this storyline!
Shadman, for the love of god do some yugioh shit man, you just remenbered me of Téa Gardner
She remmenbers me of Téa Gardner, man do some yu gi oh stuff
This bitch really do be 6’11”
No one’s going to mention the Machine Head lyrics? Fucking hell. “Darkness Inside” may not be their heaviest song by far, but it’s a masterpiece.
Why in the first panel zucc so damn thicc
S’il vous plait…
Please do more of this!!
more
YES MORE BEEFY TONED GIRLS!