A gay story: Becoming a Woman in Prison Ch. 03 Chapter 3
I’m back at the glory hole in the video store off I-75 and I’ve already sucked off four cocks. Today is busy, a lot of anonymous Johns coming to get off. I can feel my throat coated in cum, almost a numb feeling that I love and crave. The first came almost instantly, his dick was so small there was no need for me to use my hands, I just took it in my throat and suctioned it, he came moments later, not even a knock. I could hear him moaning as if he himself was surprised he was cumming. The other 3 were alright, medium sized. I’m craving a monster black cock, and I’m hoping the next guy delivers.
I’m wearing a mini skirt and heels, with a half shirt with long sleeves. I chose a red wig today, curly hair. I clear my throat, thinking about how much I love the taste of a hot seed. I’m jerking my sissy clit through the thong I wear, edging myself as I wait for the next cock to arrive. My boy pussy is on fire, its been awhile since I’ve been fucked and I am craving it so bad. My mind wanders off to my time in prison and memories begin to rush into my head. I wish I had more courage to be a woman on the outside, in prison it was so much easier, I was accepted as a woman. Here in the real world, things can be different.
I hear the door open and another man has entered the opposite side of the glory hole, my sissy clit pulses as I begin to get excited, I think he is black… Yes! He is! And he’s tall! You know what that means…. I hear the unbuckle of a belt and the sound of a soft cock being flopped out of a zipper. The dick that comes through the hole looks… magnificent. It’s long, about 10 inches, and thick as a tree trunk. I stop for a second… Is this cock familiar? I tell myself no and snap out of it. A lot of cocks look the same.
My boy pussy twitches as I reposition myself to get ready to take it in my throat. I slurp it into my mouth as I hear a “Yeahhhh” from the other side. Again, a familiar voice. Am I going crazy? I have an idea of who I am thinking of but there’s no way. I begin bobbing up and down on the big black dick like a good girl and can feel it grow hard as a rock instantly. I begin using my hands to stroke the shaft. Thick veins begin breathing around the cock as the man thrusts in and out of the hole, in and out of my throat. All I can keep thinking of is two things: do I know this man? And also: I need to get fucked and this would be the cock to do it.
“Yeahhh gimme that neck” the man says, moaning. I begin twirling my tongue around the head of his cock as I stroke in my trademarked swirl, you can hear the wet friction of my hands as I work the big black cock. Suddenly, the thrusting stops, and so does his moaning. The next thing he says makes me stop dead and freeze.
“Clarissa? That you?”
*******
After Dixie serviced the gang in the showers I could think of nothing but wanting to be a woman. For Devon, and for the gang. I had always been one to rise to a challenge, and one had presented itself to me. I began waking Devon up with a blowjob every morning, and I could tell I was getting better at it. The time it took for him to cum began getting shorter and shorter. It was like I couldn’t get enough of the taste of his salty cum, and my throat begged for it every morning and throughout the day. I would ask occasionally to cum, but he wouldn’t let me. It made me frustrated but it also kept me in a state of constant horniness, constantly wet. I began wondering what it would be like to get fucked, and I would ask Devon to fuck me. He would tell me “You not ready, you not a full woman yet. I only fuck women”. He would have me suck his balls for hours on end though, which was really hot. He had gigantic black balls and I would soak them in my mouth while he read or slept. I would walk around our cell trying to bend over near him or stick my ass out, hoping he would catch a glance and want to fuck me. A week passed, and then another. Devon had Dixie begin to give me feminine training sessions at rec time, we would go to the library in the back section and she would give me pointers on how to act, talk, and walk like a woman. My hair began to grow out a bit, but it was still a work in progress. Another week passed. The gang would look at me longingly, I could tell they wanted a taste. Devon also had me start taking hormones, one pill a day. I didn’t feel much different, but my voice definitely started to get a little higher. I was already hairless and curvy but Dixie told me I would start to feel different after a month. I would walk with Devon wherever he went, clad on his arm, I was his property. The rest of the jail, and even some of the guards would look on in jealousy at his prized possession, I think they could tell I was getting feminized even more.
One day in the library, I was practicing how to walk like a woman with Dixie in one of her feminization sessions.
“Okay girl, from the top!” Dixie said, with a cute wink, propping her legs like a stallion and turning, walking in a straight line, feet almost crossing one another, her ass shaked from one side to the other as she walked. It was like watching a goddess, her ass hanging out of the back of her short shorts. She reached the end and turned, one hand on her hips, smiling and winking. I could see her tiny dick poking through the booty shorts.
“Now your turn Clarissa!” she said as I gulped. I had been practicing but I was nowhere near the flow Dixie had, the gratefulness and femininity she exuded. I stood up and started walking, one foot crossing the other. I could feel my ass swaying as I walked.
“Yes girl!” Dixie cheered, clapping her hands lightly. Suddenly, I stumbled and broke my flow.
“Dammnit!” I yelled.
“Clarissa, don’t worry about it, let’s try again.”
“I’m wearing this jumpsuit, how am I supposed to feel feminine?” I said as I looked down at my baggy jumpsuit.
“Devon says you aren’t ready to wear booty shorts yet… what he says goes”
I scoffed, frustrated. Dixie could notice this.
“One second, here-”
Dixie took off her shirt, I could see her tiny bee sting breasts. She looked like a petite woman. She then slid off her booty shorts, wearing a pair of pink panties underneath. Despite the tiny bulge in her crotch, she truly looked like a woman. I was stunned, and jealous. She handed me the booty shorts and cut shirt.
“Let’s trade.”
“You sure?”
“Yeah, just while we were here. I want you to feel like the woman I know you will become.”
I took the shorts and shirt and stripped off my baggy jumpsuit, Dixie put it on but left the front open, she still looked like a woman. She looked at me standing there naked.
“Yeah. You’re gonna be a better woman than me Clarissa, look at your curves!”
I took a look at myself and was surprised to see what she meant. My hips were wide and my ass fat. I had perky bee stings myself, a little more voluptuous than her. I hid my tiny cock as I put on the booty shorts. They were a little tight on me.
“Damn Clarissa you got a fat ass.. Look at that thing!!”
I looked behind me and she wasn’t wrong. My thick white bubble looked so sexy in the shorts! So round and juicy, I wiggled my waist and watched my ass shake in the short shorts. I had been wearing the baggy jumpsuit for so long I didn’t realize how nice of an ass I was getting. The hormones were definitely doing something. I slipped the shirt on and it was also tight.
“OMG Clarissa, your chest looks amazing!” Dixie cried. My breasts were small but perky in the tight shirt, I could see my nipples through it. I turned and caught myself in the reflection and was stunned. Staring back was a curvy sissy, me. Nice thick hairless legs, juicy thighs, a round jiggly ass, tiny waits, and two decently sized breasts. Not huge breasts, but big enough to trick my mind into thinking I was staring at a woman. Plus, my hair getting slightly longer helped. I turned slightly and did a stallion stance, one leg lifted slightly and oh my god I looked sexy!! It filled me with confidence.
“Girl you look delicious” Dixie said, and I could see her slightly rubbing between her legs. “Now walk, give me your best”
Filled with confidence, I turned and tried the walk again. One foot in front of the other, slightly crossing my legs as I walked. This time, I was actually doing it! I could feel my ass and hips sway and jiggle as I walked. I reached the end of the walk and turned, striking a stallion pose, hand on my waist, smiling at Dixie. Dixie looked mesmerized, and I could see she was rubbing her boy clit through the jumpsuit.
“Wow Clarissa… that was hot, even for me…”
I blushed, I could tell Dixie was turned on. I had never thought of her like that but knowing she was turned on turned me on a little bit too. I suddenly thought about sucking a cock on my knees next to her and felt my tiny clit begin to throb. I hoped that one day we could do things together and possibly make out. Lesbians of sorts… My cheeks had become inflamed. Suddenly I noticed through the bookshelf a familiar face… The guard who had been eyeing me my whole time here. He was watching me. I looked down and could see through the lower shelf he was stroking his cock. It had been awhile since I had seen a white cock, I stared at it for a second but then looked away, pretending I didn’t notice him watching. I wanted all eyes on me in this sissy outfit. I wanted to be a woman. I turned and did the walk again, and out of the side of my eye could see the guard continue to stroke himself. It was a little creepy, but it turned me on! I was starting to really get horny thinking about the men here wanting me. I finished the walk, but this time, I bent over and popped my ass out, holding it for a second and shaking it before standing back up. I looked back and the guard was gone. I felt a little disappointed. Hmm. Guess he had to go somewhere else.
“One more time for me Clarissa” Dixie said, still rubbing her crotch. I could tell she was turned on. “I hope they make us have a threesome soon… I want to watch you in action. Me and you could make the entire gang cum easy.”
“That would be hot…” I said, my tiny cock was hard, poking through the short shorts. I did the walk one last time, nailing it perfectly. As I turned and struck a pose, I looked back, Dixie had stopped rubbing her boy clit. Behind her stood Devon, and he was stroking his massive cock looking at me. Dixie spoke quickly.
“Sorry Daddy, Clarissa wanted to try on my clothes-”
“Shut up bitch.” Dixie went silent. Devon kept stroking his cock as he looked at me, and my sissy dick pulsed with pleasure during it.
“Damn Clarissa, you lookin real good. Almost like a woman. You makin good progress.” He turned to Dixie. “Dixie get yo ass back to Shaun’s cell and get some new clothes on, Clarissa keeping these.”
“Yes Daddy!” Dixie said as she got up, gave Devon a kiss, and left the back of the library, she smiled at me and winked on her way out as if to say “Good job”.
Devon, still stroking his dick, smiled at me.
“You like what you see, Daddy?” I said, trying to sound as feminine as I could. I was getting more confident.
“Yeah bitch I do. Now walk towards me.” Devon commanded. I didn’t hesitate. I was ready. I strutted over as best as I could, feeling my ass sway and thighs jiggle as I walked. When I reached Devon, he towered over me, almost seven feet tall. He looked down on me like the Daddy he was, checking out my body in the short shorts and low cut shirt. I was almost breathless, all I could smell was his manliness. I went on my tippy toes and tried to kiss his big lips, but he smacked me across the face suddenly, almost making me spin.
“You looking like a female, but you ain’t there yet faggot. You got some work to do.”
I held my face, almost in tears, feeling horrible about myself. Devon came up and wrapped an arm around me.
“I didn’t say you are doing a bad job, but you ain’t there yet. I only kiss women, and you not a woman… not yet.”
I felt another burst of needing to be Devon’s woman, I wanted him to accept me like he accepted Dixie.
“Should we go back?” I said, looking at Devon.
“Not yet. I wanna cum on that ass.” Devon then lifted me and placed me on one of the reading tables. “On all fours, ass up, back arched” he commanded, and I did just that. My face on the wood surface of the table, I lifted my ass and arched my back, slightly wiggling my ass. He continued to stroke his meat as he towered over me. I could hear the friction of his hand on his dick.
“Yeah…. This ass baby… So fat… Can’t wait to fuck you.” Devon said as he slapped his cock on my ass and rubbed it all over, on top then between my legs. He was rock hard now. My tiny dick throbbed and my ass pussy ached.
“I want it Daddy, please, I need to cum”
“I bet you do. And you will soon if you’re a good girl.” I could hear Devon stroking over my ass, and the tip of his massive meat pressed firmly against my boy pussy, his cock pulsing. I had never felt so hot before, I could see a little wet spot forming from my precum on the tight short shorts. Everything in my body ached to cum. I wiggled my ass lightly against his cock head as Devon began to moan louder. He grabbed my ass with his other hand and squeezed, just one hand could grab the entirety of one of my ass cheeks.
“Oh yeahhhhh” Devon moaned, and I could feel warm wetness through my booty shorts, right on my ass cheek. Devon was unloading his cock onto my ass. Electricity shot between my legs, and I almost came hands free just from Dixie’s tight shorts. Devon finished and put his cock back inside his jumpsuit. A loud buzz rang out.
“INMATES RETURN TO YOUR CELLS, REC TIME IS OVER”
“Get up bitch. Let’s go.”
I got up, Devon’s warm seed all over my ass cheek, forming a huge wet spot on the ass of my shorts. It was so much!! I felt slightly sad that it wasn’t in my throat. We began walking out of the library. I looked behind the bookshelf the guard had been peeping from and saw on the floor a puddle of cum. He must have busted a nut and then left. It made me feel super sexy.
When we got to the edge of the library Devon turned to me. “I want you to walk like you were walking in there.”
“Yes Daddy” I said without pause. I took a deep breath. We walked out of the library and I realized this would be the first time I was walking through the prison in anything but the baggy jumpsuit. As I walked, one foot crossing in front of the other, I turned heads, literally. My ass swayed side to side as I went. Almost every prisoner we walked by turned and gawked at me as I clung to Devon’s arm. I was his property, what he said was law. Even most of the guards did a double take, probably thinking I was a real woman. I also had a large wet stain on my ass cheek, clear to most that it was Devon’s seed.
I couldn’t wait to grow my hair out longer and start wearing makeup, I couldn’t wait to be a woman.
That night I sucked off Devon three times in a row. I could get him to cum in less than three minutes, and could feel my skills getting better. The entire time he would grab at my ass and thighs, and play with my nipples. After, we lay next to each other. Devon, almost asleep, muttered “Soon you gonna suck off my right hand man, Lex. Ima slowly start letting the gang get a taste of you.”
“Yes Daddy.”
“Goodnight bitch.”
“Goodnight Daddy”