Okay. So I fucked up.

As they say, “Do the crime, do the time.” So I am.

I’m not sure I deserved this, though.

It started the day I found a suitcase of money underneath the train seat as I journeyed home from work. I didn’t know it was full of money. I just tried the latches to check to see if there were any I.D. documents in it to identify the owner.

The case was packed to the brim with large denomination notes.

Yes, I know. I should have handed the case to the nearest police station. But I was tempted, you know?

This wasn’t the crime that had me sent away, though. It was what happened after.

You see, the case belonged to one of the local crime gangs.

I don’t know how they found who took the case. If I had to guess, they either bribed or coerced someone in the security room to show them the train carriage’s CCTV footage.

Someone was sent to ‘encourage’ me to hand over the case.

Now, I’m a pretty big guy. I stand 6ft. 4 in. (193 cm) and weigh a well-muscled 276 lb (125 kg). I’ve competed in Muay Thai tournaments professionally with some success.

I was able to ‘persuade’ this guy to leave me alone.

The gang sent four guys with knives, and guns, to retrieve their property.

All this did was convince me that if I could make them leave me alone, the money would be mine. It’s not like they were going to call the cops, were they?

I dealt with these four guys and sent a message back. “Leave me alone, or I will come after you!”

Didn’t work. Of course, it didn’t. There was almost a quarter of a million dollars in that case. The gang was never going to give that up.

Besides, they couldn’t have some ‘civilian’ stealing from them, now could they? What kind of message does that send?

Hey, I said I’m big and strong. I never said I was smart!

The gang sent a group to get me and retrieve their property. During this kerfuffle, I killed a man. I didn’t mean to, but bad things happen when there are knives and guns.

They got their case back.

With my other ... ummm... ‘minor indiscretions’, I faced the three-strike policy and got the mandatory 18 years.

I’ve done prison time before. It’s not pleasant, but you keep your head down, keep to yourself, and mind your own business.

You become the proverbial three monkeys all in one. You hear no evil, see no evil, speak no evil.

I got through the first three years without a problem. There were a couple of minor confrontations with members of the gang who were inside with me. But, as I had stayed shtum on what the ruckus had been about, and because I had swiftly handled any attempted retaliation, plus they had the case, the gang, mostly, left me alone.

Everything was going fine until the fateful day arrived. I was sitting on my cell bed. I don’t like heights, so I was happy to take the lower bed.

As I read my book, the cell door opened, and Sampson, one of the prison guards, came in. He was holding a computer tablet.

“Out!” The guard demanded of Jimmy, my cellmate.

My cellmate found somewhere else to be.

“Look what I found,” he crowed.

“Your wife on all fours with a cock in every hole?” I ventured.

I really didn’t like Sampson. He was a smug, pudgy bastard who mercilessly bullied the weaker prisoners but cowered around the strong ones. I was a strong one.

“That smart mouth of yours is going to get you an ‘accidental stair fall’ one day, Michael”, Sampson snarled at me.

It’s always Michael. Not Mike, nor Mikey, nor Mick. Always Michael. Got it? Don’t forget.

“Maybe, Kid Sampson (a reference to a Catch-22 character that was a small weak kid). But not today, and not by you!” I sneered back.

Sampson placed the tablet in front of me. My blood ran cold. Somehow he had found one of my Biaustralia profiles.

I have a very deeply hidden secret. I like to crossdress. It’s harmless fun. I like the pantomime of it.

When I ‘dress’, I go the whole hog. I completely shave down from head to toe. Wig on, make up. Stay-up stockings, 7 in. heels. Corset and control briefs. The briefs hide the ‘bulge’.

Somehow, Sampson had found my MarieGoodTG profile along with the many pictures on it.

I tried to bluster my way out of it. “Who’s that, Sampson? Your new girlfriend? Bit of a minger, isn’t she?”

“It’s definitely you,” Sampson said. “You know how I can tell? These two moles right here.”

He pointed to the two small moles on the right side of my nose and the two in the picture.

“Wait till I show this to the other guards and the rest of the inmates. What will they think when they find big, tough Michael is a fairy? A nancy boy? A knob gobbler?”

“I guess I’ll have to belt a few of them to settle them back down, won’t I?” I bluffed.

“You didn’t refute being called a knob gobbler, Michael,” Sampson pointed out. “Does big tough Michael like to suck cock?”

When I’m all dressed up, I instantly become a submissive cock sucking, anal loving whore. What’s the point of getting yourself all dolled up and as feminine as possible if you’re not going to play the female part?

Sampson studied the photo intently. “You know, Marie? You make quite an attractive woman. I’d probably quite enjoy getting a blow job from you.”

“In your dreams and my nightmares, porky!” I blustered.

Sampson turned to look at me, then folded his arms across his chest. “I will come and get you around 11.00 pm tonight. I’ll have everything you’ll need to transform yourself to this,” he tapped the tablet’s screen. “Once you’ve made yourself all pretty, you can give me head and, maybe, I won’t show this to everyone.”

I may not be the sharpest tool in the shed, but I know how these things work. He was going to ask for more and more to keep my alter identity a secret until I became his owned bitch, but what choice did I have?

Once those pictures made it into prison distribution, I would be everybody’s bitch.

Desperately trying to think of a way out, I tried, “Why don’t I just belt you and take the tablet off you?”

“Do you think your profile can only be accessed from this device then, Michael? Are you really that stupid? No, go for it! Take a swing at me. I know at least 15 other officers that would love an excuse to beat your arse!”

There are always a few prison guards who like to take physical liberties with the prisoners. I had to ‘explain’ to a few of them they shouldn’t try that with me.

“I’ll see you at 11.00, Marie,” Sampson sniggered as he wandered out.

I was fucked. Proverbially, and probably literally!

“What was that about?” My cellmate asked as he re-entered the cell.

“You know Sampson,” I answered absently, still trying to think of a way out. “Does he need a reason to fuck with you?”

“He seemed pretty pleased with himself,” Jimmy said.

“Probably glad I hadn’t belted him,” I replied.

Jimmy laughed.

The day dragged interminably.

The lights went out at 9.00 pm, as usual. I lay there in the dark, dreading what was to come.

There’s no clock anywhere I can see, so it seemed an eternity had passed.

The cell door opened. “Assume the position, Michael,” Sampson said. “You are required to accompany me.”

I stood up and faced the wall, my hands going behind my back automatically. Sampson shackled my wrists and ankles. A chain stretched from my wrist cuffs to the bracelets around my ankles.

I followed Sampson out onto the dimly lit walkway. He led me down to the infirmary showers.

Before I could react, Sampson held his Taser against my balls and zapped me. I collapsed, quivering and twitching to the floor. Tears poured uncontrollably from my eyes.

“Just in case you think you can try something, Marie,” Sampson told me smugly.

Not wanting to grovel in front of this pig of a man, I forced myself to stand.

“Any shit from you in the shower, and I’ll zap your balls whilst they’re naked and wet!” Sampson said menacingly.

Sampson took the restraints off and handed me a razor with a can of shaving foam.

“Get yourself shaved off, bitch,” he told me.

“No way,” I told him. “I can’t go to the showers shaved. Everybody will know.”

“Like a give a fuck!” came Sampson’s reply. “You’re going to be sucking a lot of cock, so you may as well get used to it!”

In desperation, I said, “Listen, Sampson. I’ll dress up all pretty, I’ll even let you fuck me in the ass, but you can’t make me shave down. Everyone will see and laugh. I’ll be the prison’s bitch!”

“A good fate for you, I’d say,” Sampson answered flatly. “Make you think about how disrespectful you’ve been to the other officers and me. Besides, nobody likes a hairy crossdresser! Now get to shaving. My cock needs attention, and I have a full load for you to swallow.”

Without any other choice, I turned the shower on, lathered myself up, and shaved every inch of hair off.

I am a very hairy man, so it took a while.

Finishing, I turned to find Sampson stroking himself with his cock out. The pudgy bastard had a meagre 5 inches if that. His cock was as stiff as a board and had a thick bulbous head.

Tossing me a towel, Sampson handed me a long black wig, a corset, a pair of black stay-up stockings, and a pair of control briefs.

I donned these items and followed Sampson over to the basin mirror, where he handed me a basic makeup kit.

I was able to add some eyeliner, foundation, and blush to my face. As I’ve said, I like the pantomime of dressing, so I quite enjoyed dolling myself up. I carefully contoured my cheekbones and jawline to limit my masculinity as much as a man my size can.

Of course, Sampson had gotten me ‘whore red’ lipstick. Working carefully, I outlined my lips to make them look fuller and plumper, then filled them in.

I carefully positioned the wig on my now bald head.

Satisfied, I turned to find Sampson naked, sitting on a plastic chair, pulling on his erect cock.

“On your knees, bitch. Crawl across to daddy. Daddy needs his cock sucked.” Sampson demanded of me.

Now I was dressed, my inner slut came rushing forward.

“Yes, daddy,” I said in a low sultry voice. I ignored that Sampson would have been barely five years older than me.

I got down and began to crawl across to where Sampson was sitting. It felt so natural to be back on my knees, in front of a dominant man.

“I couldn’t find any heels in your size, slut. Otherwise, I’d have you dressed like a complete whore.” Sampson told me.

“Shoes of hollywood” came out of my mouth before I could even think.

Shaking his head, Sampson said, “Not so tough now, are we, my little bitch?”

“No, daddy,” I replied meekly.

Pushing his hips to the edge of the seat, Sampson said, “Show me your oral skills, you cock sucker.”

Eagerly I dipped my head forward and tasted the precum dripping from the eye of Sampson’s cock.

Sampson was a smoker, so his secretions were bitter. I didn’t care. It had been more than three years since I had cock in my mouth, and I was going to devour it!

Effortlessly, I accepted all of Sampson’s length into my mouth. He wasn’t long enough to reach my gag reflex, so deep throating him was a cinch.

Bobbing my head back and forth, I sucked his entire length, then let all but the head out before swirling my tongue around his glans and lapping at the precum dotting the eye of his penis.

Sampson stood up, “Fuck, you suck cock well, my little cum swallower. Daddy is going to choke you, then fill you full of cum.”

Holding me by the back of my head and shoving his cock into my sucking mouth as firmly as he could, Sampson managed to force himself far enough in for his cock to brush my gag reflex.

It was more that it tickled than the pressure that caused me to retch. I’d gotten over having penises slide over my gag reflex years ago and can easily swallow up to 10 inches.

Making me retch pleased Sampson immensely. “Choke on daddy’s cock, bitch. You love my big cock, don’t you, slut?”

‘Big cock?’ I thought. ‘It’s barely a cocktail wiener!’

Two more pumps, and Sampson lost his load into my mouth.

I sucked everything up gleefully. It was still a bitter mixture, but I love cocks cumming in my mouth.

Tipping my head back so Sampson could see, I opened my mouth, swirled his cum around, and then swallowed it.

Shoving me brutally away, Sampson sneered, “Get away from me, you fucking queer. Real men don’t need faggoty queens anywhere near them!”

‘Except when they’re horny and want their cocks sucked,’ I thought and covered myself up for the beating I knew was coming.

Sure enough, Sampson sunk his prison guard issued steel cap work boot into my kidneys.

Kicking me again, Sampson demanded, “Clean the faggoty makeup off your face, and get the fuck back to your cell.”

Hunched over, I staggered back to the showers.

I would be pissing blood tomorrow.

Sampson was looking for any excuse to beat me some more, so, despite the pain, I quickly washed down and got my prison uniform back on.

With the shackles on, I stumbled after Sampson to my cell.

Moving painfully inside, I collapsed onto my bed.

“Maybe you’ll show the guards more respect, now, Michael,” Sampson said to cover why he had taken me out of the cell.

The pain was so great I didn’t sleep a wink that night.

Now I was dressed in ‘drab’ what we crossdressers call our male clothes, I felt humiliated and emasculated. It would not be a good idea to cross me today.

It started with Jimmy.

“What the fuck happened to your hair?” he asked, shocked at my appearance.

“I had chemotherapy last night. What the fuck do you think happened to my hair?” I snarled at him. “Sampson happened. That’s what happened. Now get the fuck away from me!”

Noticing my grimace, Jimmy asked, “You alright, Michael? You don’t look so well.”

“Do you want me to show you how well I am by bouncing you around this fucking cell? I growled.

Knowing when to shut up, Jimmy picked up a book, turned his back, and pretended to read.

When the bell sounded and the doors opened, I steeled myself, pulled my shoulders back and head up and forced myself to stroll down to the dining hall.

As soon as I entered, the muttered comments started. It was like an approaching wave from behind. Every table I passed began whispering about my shaved head.

Taking my usual spot, I waited for Jimmy to bring my breakfast, as he always does. I protect him, and he acts as my valet. That’s the deal.

Alonzo, a huge black man, who was my only real challenger as the hardest man in the prison block, grabbed my wrist and inspected my arm.

“Unless you’re planning on losing a hand, I’d let the fuck go,” I told him.

Alonzo raised an eyebrow and then grinned at me.

“Sampson happened?” He asked.

I nodded.

Alonzo and I get along well. He knows I have no interest in challenging him for superiority and that I’ll back him in any confrontation.

“I’ll see what I can do, babe,” he said.

He has always called me ‘babe’, so there was no hidden meaning.

Nothing happened for almost a month. Most of my body hair had grown back.

I was hoping that Alonzo had managed to get Sampson to back off. He hadn’t.

Sampson appeared at my cell late one night.

We went through the same pretence.

When I got to the showers, there was another guard.

“What’s going on, Sampson?” I asked.

“Terry, here, needs a blow job, too. His wife won’t put out anymore.”

“Why would he think he could get one from me?” I asked, refusing to accept the inevitable.

Sampson waved the tablet, “He thinks you’re prettier than his wife,” he guffawed.

Staring at the abyss, I tried to make a stand. “Maybe I should just belt the fuck out of the pair of you to convince you otherwise,” I threatened.

“We were hoping you’d feel that way,” Sampson said, grinning.

I got two Tasers to the balls.

Convulsing and vomiting, I was slow to regain my senses.

Tossing a razor and a can of foam beside my prone form, Sampson demanded, “Hurry the fuck up and get yourself dolled up. My balls ache.”

I did as before. Sampson had provided the 7 in heels, this time. He’d gotten some breast forms for in the corset, too.

As soon as I had finished making myself up and inserted the breast forms, my inner slut raged through me.

Swinging my hips lasciviously, I swayed into the change room.

“Hello, boys,” I crooned, “Does someone in here need their cock sucked?”

Terry and Sampson were both naked on plastic chairs. Sampson was already hard, but Terry was only at ‘half-mast’, so I knelt before him first.

Placing my hands on the armrests, I formed my lips into an ‘O’, then took the head of his cock into my mouth.

Terry was only marginally bigger than Sampson, so I effortlessly swallowed him whole.

Flattening my tongue against Terry’s shaft, I sucked firmly and bobbed my head up and down, ensuring that the exquisite part, just below the eye of his penis, was in contact with my tongue the whole time.

Terry grabbed my head and began to hump at my sucking orifice. “Fuck me!” He moaned. “She’s as good as you said she was!”

“I’m going to try her ass,” Sampson stated.

That wasn’t part of our deal, but with my inner slut raging, I didn’t care. I wanted to be fucked!

Alternating deep throating with swirling my tongue around the head of Terry’s penis, I soon had him teetering on the edge of an orgasm.

Sampson had moved behind me. I felt his chubby hands on my hips as he pulled my control briefs down. My balls fell into view.

“I don’t want to see those disgusting things,” he complained. “Reach back and cup them up out of the way.”

Moaning around Terry’s cock, I complied.

Sampson spat on his hand and smeared it over the bulbous head of his cock.

Positioning himself at my ass, he found he couldn’t reach it. He was too short, and his cock was too small.

Sampson smacked my ass, “Spread your knees and lower yourself down, slut. Daddy needs to fuck your ass!”

I quickly lowered my ass. My pucker hole was clenching and opening in anticipation.

I felt Sampson’s dick at the entrance to my man cunt. Holding my hips, he brutally ripped me back and thrust his hips forward.

The bulbous head of his cock tore through my knot and into my colon.

With an almost womanly squeal, I clenched my ring down on Sampson’s cock and bucked back at him.

“You even scream like a bitch,” Sampson muttered.

Smacking my ass continuously, Sampson sawed his cock in and out of my rear fuck hole.

He wasn’t long enough to reach my prostate, but the ass smacks were delectable. Before long, I was nearing orgasm.

Cupping Terry’s balls, I bobbed my head faster and more insistently, up and down his cock. I pulled his balls gently down. This stretched the skin on that sensitive spot below the eye and added an extra dimension to the pleasure from my tongue.

Sampson was panting and grunting at my ass. I could tell he was about to cum. Wanting to be filled from both ends simultaneously, I furiously worked my tongue around Terry’s glans.

With a stifled grunt from Terry, his cock spat into my greedily sucking mouth. Spurt after spurt was welcomed down my throat. It was a little salty with a pleasant, sweet aftertaste.

With another, extra hard, smack to my ass, Sampson unloaded inside my colon.

Feeling his cum splashing inside my bowel sent me over the edge. With another high pitched squeal, I came, my dick shooting cum onto the floor.

Both men stormed to their feet.

I quickly covered my head and scrunched up into a ball.

“That fucking faggot squirted on my boots, Sampson! Make the queer lick it off!”

Sinking a boot into my exposed balls, causing me to retch and almost vomit, Sampson demanded, “Crawl over and lick his boots clean, you fucking queerbo!”

I quickly complied, hoping to avoid further beatings. It was a forlorn hope. As soon as Terry’s boots were cleaned to his satisfaction, he and Sampson whaled into me. I was punched and kicked repeatedly.

I don’t know how long I survived before I passed out.

Geoffrey, the morning nurse, found me naked but still made up.

Helping me onto a trolley, he rolled me into the infirmary. With surprising gentleness, Geoffrey cleaned my makeup off. He cleaned the blood from the various cuts and scrapes and rubbed soothing ointment into my bruises.

Geoffrey handed me a cup of water and two painkillers, “If you’re going to make yourself up like a girl and bring men in here, you need to pick your johns more carefully. I can probably cover this one up for you, for a price, but I won’t be able to too often.”

Groaning, I knew what the price would be. “Can you please wait until I can breathe without pain before getting your blow job?” I begged.

“Only if I can bring the outfit I want you to wear,” Geoffrey stated.

I nodded painfully.

“Good girl,” he told me as he patted my shoulder.

The painkillers kicked in, and I drifted off to la-la land.

I spent two days in the infirmary as my body recuperated from its beating.

I had been lucky. Either that, or neither Sampson nor Terry wanted to mess my face up. Who wants to get a blow job from a deformed crossdresser?

I didn’t see, nor hear from, either Sampson or Terry, but I’m sure word was spreading.

It may have only been paranoia, but I’m sure that more and more of the guards looked at me with knowing eyes every day.

A week passed without incident. Only Jimmy noticed that I was even more quiet and aloof than usual.

“You doing okay, Michael?” He asked.

“18 years is a long time, is all,” I told him.

Another of the prison guards fetched me after lunch one day. “The infirmary nurse says you need to come in for a follow-up check on your injury,” he said.

Sighing, I replied, “I don’t suppose I could just say I feel fine, and you’d leave it at that, would you, Boss?”

The guard shrugged, “I couldn’t give a fuck if you live or die, but I don’t want to have to do the paperwork if you die, so off we go, boyo!”

I followed him down to the infirmary. Geoffrey was waiting for me.

He slipped the guard $50, “If you’d like to wait outside, I’d appreciate it,” he said.

The guard looked at the $50, shrugged his shoulders, and replied, “On your head.”

“We’ve got about an hour,” Geoffrey said. “Don’t worry about shaving your body. It is close enough. Shave your face and get yourself made up.”

He handed me a more extensive makeup kit than I had used for Sampson.

It didn’t take me long to do a full makeup job.

I saw Geoffrey’s hand appear from behind the ajar door in the mirror. He held a skimpy bright yellow dress, a black sheer bra and thong set, some filled water balloons to use as breasts, and a long blonde wig.

The door closed momentarily before it reopened, and a pair of thigh-high 7 in. heeled boots appeared.

Dressing quickly, I tucked my cock and balls behind my thighs and then minced out into the infirmary.

Fuck me. There were three people out there. Geoffrey, another male, and one of the female nurses. A bigger buxom girl about 50 years old.

“I invited some friends to the party,” Geoffrey smiled.

My inner slut ignited. Licking my lips salaciously, I said, “I will let you all fuck me as long as you promise to cum inside me.”

“Deal!” Geoffrey exalted.

He led me over to an examination table. Pushing on my shoulders, he had me lying face down, with my hips and upper body on the table. My feet, in the 7 in. heels, were splayed and on the floor.

The female nurse climbed onto the examination table, hoisted her uniform up, and shoved her hairy cunt into my face. Grabbing me by the back of the head, Sylvia, by her name tag, ground her twat against my mouth and tongue.

It was a nice change from cock!

Sylvia was controlling the action. I couldn’t see nor move with my face pressed tightly against her pussy, so I licked everything I could reach feverishly. I was rewarded with a long, drawn-out moan.

Someone took my hand and wrapped it around their cock. I eagerly stroked it. Gripping the skin below the head firmly, I tugged gently on it.

The hem of the dress, which didn’t even go close to covering my ass cheeks, was lifted, and my thong was moved aside. I felt a warm breath on my ass before a tongue delved between my ass cheeks.

Now that was fucking good!

The invading tongue probed around my rosebud and tried to force itself inside.

Taking a deep breath before sighing it out, I relaxed my sphincter and welcomed the moist warm tongue into my ass.

The exhaled sigh blew across Sylvia’s clitoris. With a groan, Sylvia pressed me more firmly against her twat. My mouth was over her clitoris. Sucking that delicious pleasure nub into my mouth, I swirled my tongue over and around it.

Sylvia stiffened, then exploded into the first of many orgasms she would have that afternoon.

Sylvia was a squirter. Her juices flowed over my tongue and down my chin. I eagerly lapped up as much of her sweet nectar as I could.

The tongue in my ass was replaced with a finger, quickly followed by another when the owner found my ass readily accepted the first one. The fingers probed into my ass and found my prostate.

A surprised grunt escaped my mouth.

The sharp exhalation of breath from my grunt blew across Sylvia’s clit. She popped, then squirted again.

Having my prostate fingered soon had me dripping precum. The cock in my hand was removed, and a mouth found my turgid member.

I have a solid 7 inches of cock. The mouth’s owner was able to swallow it all.

It was my turn to moan, but the fingers and mouth were removed just as I was about to blow.

“No cumming just yet, pretty girl,” Geoffrey admonished me.

Sylvia climbed off the table. The other male took her place.

He shoved his cock rudely into my mouth. I did not mind one bit! I sucked as much of his shaft into my mouth as I could reach. Realising I could easily accept more, the cock’s owner scooted forward on the table.

Revelling in my ability to swallow even huge cocks, I allowed the cock deeper and deeper until my lips were pressed against the owner’s abdomen.

“Fuck, you’ve found a top-notch cocksucker here, Geoffrey,” the man groaned.

“Prison is always the best place to find gifted cocksuckers,” Geoffrey told him.

Geoffrey had Sylvia bent over one of the other tables and was pounding her ass just as hard as he could. Sylvia was obviously an experienced anal exponent as she hadn’t twitched or moaned as Geoffrey rammed his dick into her ass.

Watching Geoffrey’s long thin dick vigorously shafting Sylvia’s anal passage had my mouth watering in anticipation. I wanted that cock!

The man I was sucking pushed me off his cock.

“Time to try your boy pussy,” he told me.

“Yes, please, Sir,” I begged him. “Fill this slut girl with cock!”

Sylvia groaned at my words and pushed back harder at the cock in her arse.

Holding his cock in his hand, Geoffrey’s friend rubbed the head across my still wet rosebud. Homing in on the centre, he held my hip and then gently but firmly pushed the head of his cock through my sphincter.

I moaned with delight as his cock slid through my knot and deep into my shithole.

This man was bigger than Sampson and Terry but not as long as Geoffrey. He had a wider circumference than Geoffrey, though. As his hips came in contact with my ass cheeks, the tip of his cock scraped across my prostate.

Jumping in ecstasy, I moved my hips forward as far as the table would allow me, then slammed back at him. Geoffrey’s friend got the hint. Gripping my ass cheeks firmly, he began to fuck me.

Whenever his pelvis hit my ass, his cock scraped across my prostate, and I would jump, then hump back at him.

The head of my rampantly hard cock banged against the examination table as Geoffrey’s friend drove into me. Added to the prostate scraping, this stimulation had me back on the edge of cumming.

Geoffrey noticed that I was about to blow, “Hurry up and cum in her ass before she loses her load,” he instructed his friend.