Prison Life: Step into a Woman's Shoes Chapter 2
Chapter 2
Sleeplessness plagued me that night as my petite erection throbbed and yearned for release. My roommate, Devon, lay next to me snoring loudly. Despite the internal confusion, I found comfort in his presence. I pondered over my sexuality. Was I gay? In my current situation, it hardly mattered. I had already submitted to the prison's top inmate and given him a blowjob. Stubbornly, I vowed to fulfill my role as his submissive girlfriend. I adored the feeling of desirability. For the first time in my life, I felt sexy. I lay beside Devon, taking in his masculine body - his chiseled chest and well-defined abs. I gazed at the cell's barely-there walls, contemplating my current predicament. No turning back now; I was officially in prison. The world outside loomed in darkness, evident through the tiny window on the cell door.
Suddenly, Devon's snoring ceased. My derriere was gripped by a large hand, causing my pecker to stir. Devon had awoken.
"Morning, slut" he murmured, squeezing my plump rear.
"Good morning, Daddy" I responded, rubbing against his chest. His hairy arms looped around me, his hand caressing my plump posterior again. My strained little cock twitched, leaking pre-cum onto his leg.
"When I say good morning, say good morning to your Daddy, you worthless piece of shit."
"Good morning, Daddy" I repeated, stroking his sleeve-tattooed arm. Devon relaxed his arm, moving it to my back. He pulled me closer, and his fingers tightened on my backside. My aching erection throbbed wildly.
"May I cum?" I pleaded, still in a daze.
"Not yet, sweetheart. Save it for later. But first, let me ease your morning wood," Devon teased as I traced his rod. It was massive - a polished pipe with veins twisting along it. I wondered how to satisfy such a humongous instrument.
"Go ahead, take care of my morning wood before the morning call," he commanded as I moved to his lower legs. I put my round wobbly ass above his upper thighs. Sitting on his lower legs, I held his stunning phallus before my face.
"Stroke that cock and suck!" he ordered. I gripped his dick, loving the solidity of his crisp manhood, and started to work it with my tongue. The taste was odd - a mixture of sweat and salty cum. Devon groaned with pleasure, spurring my nipples to harden.
"Now, arch your back" Devon demanded, catching a glimpse of my wobbling rear. My swaying ass captivated him. I humiliatingly obeyed.
"You look so delectable, ready to suck my cock. Arch your back more." I enthusiastically arched my spine.
"Now, take my cock into your throat" Devon instructed, his hand pushing my head down further on his enormous flesh staff. It was challenging and somewhat uncomfortable but I persisted.
"Stick your round ass up and keep sucking" he told me, pushing me down on his tool. With my derriere up, I continued to suck his dick while struggling to swallow his hefty member.
"Push your hips up more," Devon said, thrusting me down onto his dick. With my ass arched and the weight of my body pressing against him, Devon pleasured himself at my expense. The fire in my core grew as I humiliatedly served my "Daddy". Not only was I his sexual plaything, but I also yearned for a climax but knew I'd be unable to achieve it. Coincidentally, failing to satisfy Devon stimulated me.
"Arch your back more. You look so hot with your jiggly ass bobbing while you suck me off." I complied, pushing my hips upward more as my head bobbed up and down on his rod.
"Swallow my cock, the deeper the better." Inspired by his gratification, I wiggled my ass invitingly.
"You'll be an amazing woman", he extolled, and I blushed. The thought of being his concubine was terrifying but also somewhat intoxicating. A combination of guilt and excitement surged through my body like a wildfire.
"Daddy, may Icum?" I asked semi-desperately, hoping for his permission. He backhanded my face.
"No! Not yet, I've got some ideas for you", he barked, causing slight pain but also pleasure akin to sadism.
"You've got to show your worth. Today, you'll witness how my lady Dixie goes about her business, and you're gonna be the one to watch."
I thought back to the woman I spotted with Devon on my first day at the main rec area. Dixie was attractive and almost convincingly female.
"Dixie is my main girl, but she's nothing like you," Devon remarked as he squeezed my thick thighs and spanked my rounded buttocks. I felt awkward, yet stimulated.
Suddenly, the lights flickered on, and a loud bell rang out.
"ATTENTION, ALL INMATES - HEAD TO BREAKFAST NOW!"
The doors burst open.
"Get dressed; we're going to have breakfast."
*******
At the common eating space, the entire prison filled with people. I sat with Devon and his gang - around 30 guys, all tall, muscular, and remarkably strong. We were undoubtedly the most powerful group within the institution. Dixie was on one side of Devon, while I sat on the other, my eyes locked on her. As I continually admired her femininity, her legs that seemed to be more womanly than masculine and her small yet curvy backside, I couldn't help but wonder how she managed to sport such a feminine appearance. She had a mini-skirt-type short made from her jumpsuit, and she'd tied her top into a crop top. The back of her head was concealed by a bandanna, with short, golden locks poking out from the front. Her eyes were lined with mascara, and her lips were painted a vibrant red. How did she get hold of such cosmetics? I pondered. And yet, she was the epitome of femininity - not only visually, but also in the mannerisms she displayed. She flirted with the other guys in the group, laughing and flashing them mysterious glances. We devoured our meals: cold grits, liquidy scrambled eggs, and a single piece of toast. Devon polished off most of my portion. I stared around and couldn't prevent myself from being the center of attention of both the gang and those around us. Their gazes made me feel like I was a tasty piece of meat, and a few even salivated over me. I couldn't help but relish the way they looked at me. The guard who had eyed me during my intake exam was among the onlookers. He offered me a sly wink as he walked away, causing me incredible fascination.
Following breakfast, we were led to the communal gymnasium, where Devon's gang started engaging in physical exercises. Devon performed pull-ups, displaying his well-defined abdominals. I envisioned the morning when I had observed his six-pack and body up close. My manhood throbbed, and I recalled how much I longed to climax. I swiveled my eyes toward Dixie, who was perched on a bench right beside me, and continued to marvel at her femininity. I felt unable to imitate her.
"Take a photograph, it'll endure longer." Dixie suggested, noticing my secret perusal.
"Um... sorry," I muttered, hastily averting my gaze.
"Don't worry about it; I find it quite appealing. I've been gazing at you too. Can't wait to see the woman you transform into here." She smiled at me, and I discovered she was speaking seriously. "Chill out, in more than one sense of the word. You're gonna require that advice."
I chuckled at her attempt at humor, but she was utterly sincere.
"So Clarissa, the name Devon bestowed upon you, right?"
"Yeah, yeah..."
"What brought you here?"
I recounted how I ended up as a prisoner, getting caught in a situation that was beyond my control.
"Ahh, the getaway driver, a cliché. The past is unchangeable now. But you're now embarking on a different adventure. Men like us don't belong in a prison, so once we arrive, we learn to be women. I used to be just like you. When I first landed here, I was a guy, yet slowly but surely I started to change. It's more than just looks; it's a new method of living." Dixie said, retrieving a tiny vial of white powder. Using her fingernail, she collected some and snorted it, jerking her head back in response to the burn. She smiled after recovering.
"Feel like trying a bump?"
"No thanks... I've never been fond of drugs."
"Suit yourself, then. Got any questions?"
"How... How do I improve at this?"
"You're only beginning your journey. This gender change will come with time and experience. How many times have you sucked Devon's knob?"
"Twice."
"Impressive! Devon said your oral skills were fantastic! It took me around four attempts to get a positive review; I had a tendency to use my teeth - I had never engaged in fellatio prior to that."
"I've had some exposure in college but I'm not homosexual."
Dixie giggled. "Well, keep telling yourself that. You've never been penetrated before?"
"Embrace the idea, that's what makes it thrilling. There's no bigger thrill than having a thick cock buried in your ass, releasing a hot load inside of you."
My sissy erection was now at full force, protruding from my jumpsuit. I tried my best to cover it up, but Dixie caught a glimpse of the wet spot of pre-cum.
"Haven't let you cum yet, have they?"
"No."
"Don't fret, you'll get there. You just need to prioritize the gang's pleasure over your own, and it'll happen."
"The gang's pleasure?"
"You'll find out," she said mysteriously. "Just wait until shower time today."
I started to feel a mixture of anxiety and excitement... Being with more than one cock at once? I wasn't certain if I could handle that... Even taking one in my mouth was a challenge.
"Calm down, you'll learn and build up your endurance. Plus, sometimes Devon rents you out to other gangs and, occasionally, the guards. You're a commodity, one meant to be used."
I kept quiet, pondering everything.
"Can I ask you something?"
"Sure, I'm an open book!"
"Why are you allowed to wear such short shorts and low-cut shirts? Everyone else in here is in a jumpsuit?"
"The sissies, the women... The warden allows them to break the dress code, and the makeup too. And let's not forget the hormones."
"Hormones?"
"That explains how my voice became so feminine. Thanks to Devon, I take a pill each day. The hormones help me grow big breasts. He's going to give you the same hormones too."
I became worried, but Dixie noticed.
"There's no need to panic. You now belong to the gang, so you'll learn to accept and even want it. Just like me, I'm a woman now. And soon, you will be too, Clarissa. You're already several steps ahead of me."
"How am I ahead of you?" I inquired.
"I admire your compliment, but have faith. Devon thinks highly of you. Two times he's sucked you off, and already he's talking you up. Plus, you've got a beautiful, 'perfect' body. Look at me! This was all from the hormones. I have to remove whatever they won't take care of. Your hair is just fine, you'll have a full head in no time."
I thought about how I hadn't had long hair since high school and, when I did, it was incredibly straight, sometimes mistaken for a girl because of my wide hips, thick legs, and long, straight hair.
A loud bell chimed throughout the prison.
"INMATES RETURN TO YOUR CELLS – WE WILL BE CALLING GROUPS FOR SHOWERS!"
Dixie rose from the bench, revealing her perky buttocks half-exposed through her shorts. She turned to me as she smiled, revealing her womanly self.
"Now you can witness what we do," she told me.
I followed Devon to the showers, him with an arm around me.
"You're about to witness what you'll be doing some day," he said.
I gulped, feeling very nervous. We arrived at the showers, finding the room packed with about fifteen large, muscular black men, all gang members. Dixie sat there on the shower bench, totally naked except for her bandanna, waiting for her turn. She removed her bandanna, displaying her shaved head. So elegant! Her body was stunning! Completely smooth. She uncrossed her legs, revealing a small cock. Already hard. As the men around stripped their clothes off, showcasing their impressive long, thick cocks, I stood in the back next to Devon, also stripping. He turned to me.
"Get undressed and sit on the bench," he instructed. I obliged, taking off my oversized jumpsuit and sitting on the bench. The men scanned my body, admiring it. Some began stroking their impressive penises. Hungry, they were.
"Ignore Clarissa," barked a guard, signaling the start of the showers.
Devon pushed me against the wall, hand on my throat.
"Say 'Daddy.'" I applied my throaty voice, "Yes... Daddy." Her strength aroused me, but I was also scared.
"Good girl..." said Devon, looking into my eyes. I felt so conflicted inside, yet my sissy cock burned with desire. I loved to be desirable, to be beautiful.
"Move along." the guard ordered.
Devon and I continued down the hall to the showers, where all the men had now fully disrobed.
"Remember, Clarissa! Today, Dixie!" he reminded me.
I observed as Dixie climbed onto the bench. Naked and in front of all the large blacks, her body was breathtaking, completely smooth. The men began stroking their cocks with anticipation. Time to learn.
Dixie knelt eagerly, her eyes gleaming with anticipation.
"Yup, daddy, I'm all set for action!"
"Alright, gents, let's chow down."
A horde of men swarmed around Dixie, each brandishing their huge erections. Devon stayed near me, stroking his own mammoth penis. I craved to suck it... my cock was hard and throbbing... I was ready to release.
Four guys converged on Dixie, who instantly grabbed onto any dicks she could reach. One large guy thrust his dick in her face; she took it into her mouth and began expertly deepthroating it. I was astounded! She plunged all the way down, and the dick must have been at least ten inches! She worked it with her lips as she stroked two more men on the sides.
"Aw yeah, fuck yeah!" the guys groaned as she performed fellatio. She detached her hands from the other two dicks and started concentrating solely on the one in her mouth. Her petite penis swayed back and forth as she deftly manipulated the giant black dick with both hands and her mouth.
"I'm gon' bust, dude!" the guy exclaimed as he arched his back and shot his load into Dixie's throat. On cue, she thrust deeper and swallowed the whole load. The men behind her continued stroking. Dixie jumped up and grabbed a new cock, immediately plunging her mouth back into action. The men positioned Dixie on the bench and bent her over.
"Yeah, I need to be fucked! I desperately need to be fucked," Dixie pleaded; her face and mannerisms seemed possessed. Lying on all fours on the bench, Dixie raised her luscious butt toward the sky, arching her back in provocative fashion. She looked amazing. I wanted to be her, on the bench with all those cocks.
I gingerly rubbed my own minuscule member, but not too hard; I was seconds away from explosion.
Noticing this, Devon grinned at me.
Dixie took another cock in her mouth while another gang member got behind her, spreading her ass cheeks.
"This ass is so fine!" he declared as he inhaled her scent and then buried his face in, feasting on her boy pussy.
"Oh, please eat me eat me!" Dixie begged. As she swallowed another dick, another guy tucked himself behind her and planted both hands on her ass cheeks.
"Damn, this ass is spot on," he said, indulging in her fragrance before shoving his face in, licking her boy pussy.
"Yes please, eat it, eat it!" she exclaimed, taking a new dick into her mouth.
She deepthroated that one as well while the other guy continued fondling her ass. The man shoving his penis into her mouth suddenly ejaculated, and I observed the thick streams of cum pouring from her mouth.
"Fu--ck yeah, fuck--king yes!" he yelled as she continued deep-throating his penis. Two men accounted for.
The guy dining on Dixie's ass moved away, and another guy moved in. Dixie began another round of deepthroating, followed by the guy shoving his penis into her ass. Dixie loved every minute of the whole ordeal. She thoroughly bathed in cum by the time the final cock splashed into her. She swallowed that too, never missing a beat. Her mouth and ass were caked in cum. The way she sucked dicks was mind-blowing, precise and efficient; she knew how to make a man come uncontrollably within minutes. With every ounce of strength, I refrained from cumming. I started pressing my ass against the bench, imagining a cock entering me and filling me with cum. The sensation played in my head over and over, desired my desire to become a woman combining with the fear of losing control. Devon understood.
"Soon, Clarissa, you'll have your turn."
"I crave for it, Daddy. I yearn to become a woman."
"I know you do. Good girl." Devon soothed as he patted my head.
Before long, only Devon's penis remained untouched. Dixie lay drenched in cum, panting and fingering herself. Her small penis twitched as she touched her anus. Devon, having reached the height of arousal, approached Dixie. She dropped onto her knees, prepared for more.
"Come on, Daddy, make me finish," she pleaded. Devon sat on the bench, picking her up and placing her on his lap. His enormous cock stood between her thighs, and she moaned as she rubbed it. She slightly rose and sat on Devon's cock, her eyes glazed over as she started moving up and down on his rod.
"MMMMM YES DADDY" She repeated, and Devon put his hands on her buttocks, pushing her up and down onto his tool.
"Girl, yeah, take that cock," he said, as I watched other men covered in cum. Devon's cock was unquestionably the biggest. I jerked off my microcock, envying Dixie. I imagined what it would be like to be Dixie. Everybody could hear Dixie moaning and "fwap fwap fwap fwap" repeated, as Devon fucked her relentlessly.
"Yeah, yeah... I'm about to cum... are you ready, Dixie?" Devon asked as he grabbed Dixie's small dick and started jerking it while fucking her.
"Yes, Daddy please please pleaseee," Dixie responded, and I witnessed the scene. I was envious as I wanted to ejaculate with everything I had.
"I'M GONNA CUMMMMM" Devon bellowed as Dixie moaned loudly. Her little dick squirted as Devon pushed her all the way down onto his mega-dick, climaxing inside of her. Dixie's eyes rolled back, and she trembled, jerking. Devon groaned out loud, and everyone observed him unloading into her. The entire group witnessed it. Dixie's dick ceased spurting cum, and Devon's thrusts lessened.
"Yeahhhh bitch... so fucking good," he groaned.
Dixie fell off Devon, facing me, with her face covered in a puddle of cum. Her boy pussy was bright pink and loosened, after being fucked by many cocks. It leaked cum. Her make-up had run down her face, and she lay there smirking at me.
"You're going to do this soon; be ready."
Everyone in the room faced me, revealing their naked black bodies and cocks. Dixie looked at me, smiling.
"Yes, Daddy, I want it," I said.
And I meant it.
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