Chapter 1
I hear footsteps enter the room on the opposite side of the wall of the dark room I'm in. I'm on my knees staring at a hole, and my mouth is watering. My heels are anxiously shifting as I adjust my mini skirt, my smooth and chunky ass and thighs popping out of it, my tiny dick starting to pulse. I run my fingers through my long straight wig. Yeah, I'm not a woman, at least not full time. But it's where I feel the most comfortable. However I spend most of my time as a man except for when I come here to this video store off the I-75 exit. Here I am comfortable enough to dress up and take dick through a gloryhole. I've been out of prison for about three years but to be honest I miss it a lot! That's where I became and was accepted as a woman. It wasn't overnight, for the most part I thought I was straight, except for a few dicks I had sucked in college before I dropped out. I liked it but always imagined having a wife and kids. That ship has sailed though.
I can hear a man approach the gloryhole, and my mouth is now dripping as I hear a zipper unzip. Yes! This guy is big, but perfect for me! He inserts his big black cock (my favorite) through the gloryhole, its soft and drooping down far below where the hole ends. That's my cue, and I get to work. I use the suction of my lips to slurp his big tool into my mouth and down my throat like a noodle. I hear a small grunt as the cock twitches, slowly becoming full of life and hardening. I'm a pro, and I start guzzling his cock, using one hand, then two as he becomes fully erect.
"God damn..." I hear through the hole as I bob up and down on his dick like the good sissy I am. I use both hands and my mouth in a circular motion as I slurp his dick up and down. His cock head is big, just how I like it! He thrusts into my hands and throat now and I begin feeling erratic movements, realizing he is getting close. I speed up, not breaking rhythm. Then I hear a knocking on the wall, my favorite part. I shove the entire cock into my throat, my lips to his groin as he cums.
"Oh fuck ohhhhh fuckkkkk" he exclaims as I feel spurts of cum fire in my throat, I drink it straight down, not to be wasted! His groaning becomes quieter as he slows his thrusts. The cock leaves the hole as I swallow my sticky throat. I want more. He leaves the room and after a minute I hear another guy enter. Perfect!
*******
Throughout my life I've always been in the wrong place at the wrong time. And when I was arrested, it was no different. I was in a robbery gone wrong, one that I should have never agreed to. I was the getaway driver and was told the guns they were using were fake. Things went south and I found myself facing 10 years in prison. I was scared shitless, being a short white guy that had always been called 'soft'. My voice was high pitched and I'm pretty sure I had an imbalance of hormones, since I never grew hair on most of my body. My dick was small and for some reason God gave me thick legs, birthing hips, and a nice hairless round booty. I even had little bee-sting man-boobs and was easy on the eyes. I was done for!
I remember when the corrections officer who did my strip down almost laughed when I undressed.
"What's so funny?" I asked.
"Boy you got a woman's body. I give it an hour before you become someone's punk."
"Ain't that the truth." Another voice said, I turned to see a different CO looking at me like I was a piece of meat. I could see a slight bulge in his pants forming.
I blushed, and felt awkward but a little turned on for some reason.
"Easy Mendez, this one's gonna get claimed quickly by the top dog."
"A man can dream can't he?" The other CO said as he shuffled his pants to hide his boner.
"Alright inmate 3962, you are good to go. Put these on." He handed me an orange jumpsuit, one way too big for me.
"This isn't my size." I said.
"Trust me, you're gonna wanna hide those curves," he said. I again blushed and felt oddly turned on. I had never felt 'wanted' in my life, women never liked me, probably because I was so petite and curvy. I had sucked off a couple of jocks in college before dropping out, but never considered myself gay. I didn't necessarily not enjoy it though, but always thought of it as a phase.
"Follow me, we will take you to the floor where you'll be assigned a cell."
Ten minutes later I entered a large communal area filled with other prisoners. From the moment I walked in, all eyes were on me. I heard several comments and barks as I walked to find a seat on a bench.
"God damn!"
"He look like a woman!"
"Wassup mama?"
"Oh shit we got a new lady!"
I felt a lot of anxiety but also was kind of turned on... This is the first time in my life I had all eyes on me, even if they were men. Most were jacked and muscular, shaved heads. Here I was this little smooth white boy. Apparently the oversized jumpsuit didn't hide much, these guys had a sixth sense. I also spotted a few feminine guys, one of which was blonde with short shorts, and wore a bandanna. He, or she, I should say, I couldn't tell, she looked like a woman! She winked at me, almost saying her own welcome. Her legs were thick and ass round, her shirt tied up halfway to emulate a belly shirt. She was next to a large black man working out, surrounded by other men. He looked at me with a smile, like I was a piece of meat. He was hands down the biggest man in here, and the way the others gathered around him I could tell he was top dog. And the femboy with the bandanna next to him was his, guaranteed. A voice came over the intercom.
"Rec time is over, all prisoners make your way to your cells."
"Inmate 3962!" I heard, taking a second to realize it was my name being called. "You've been assigned a cell. Come with me."
