I'm Jimmy James and this is a story of cross dressing and sexual submission at the hands of my girlfriends father.
============================ Working On The Chain Gang
I quickly stroked my hard cock 3 or 4 times and blew my load all over the counter. I giggled, watched myself in the mirror as I licked it up. Then quickly coated my entire body with hair remover. Waited the allotted time and jumped into the shower to rinse it and any vestige of hair down the drain.
As I did all of that, I thought about how much fun it was to be a girl. How easy it was to get sex. How much I enjoyed the sex. How many times I had, had sex. How many men I had sex with. How comforting it was to know exactly what was expected of me. But most of all. How well I was getting along with Bob because of it.
When I had finished everything, I wandered back to the kitchen to find Bob dressed in a suit. He handed me a beer and ordered me to follow him to the den. We turned on the TV and watched some football. While I had become quite comfortable walking around nude as a girl. I was quite uncomfortable to be nude as a man. Especially while there was another fully dressed man in the room. While I squirmed to cover myself. Bob seemed to delight in my discomfort as he casually drank his beer.
"Get over here and suck my cock. PUSSY" he barked.
I was devastated when he said it so abruptly like that. I gave him a hurt look, but Bobs only response was to pull out his cock and laugh at me. When I hesitated, Bob got quite angry.
"Did you hear me! I said suck my cock! You fucking pussy!" he yelled.
I slowly got to my knees and obediently began sucking his cock.
"Good Girl" he said with a derisive sneer.
While still sucking his cock, I looked up at him and couldn't believe how quickly everything had changed. Bob didn't even seem to notice my distress. He just looked down at me with a smile while he continued to drink his beer. I closed my eyes and concentrated on sucking his cock. Not two seconds later, we heard a large truck pulling up in front of the house.
"Oh Fuck! I Forgot! Here put this on and follow me." he said quickly.
Bob jumped up, put his cock away and threw me a lacy women's night gown. I put it on and quickly followed him to the front door. The gown just barely covered my ass and made my half hard cock hard to hide. He looked down at it and let out a small chuckle.
"You might want to stay out of sight while I put these guys to work." he said as he opened the door and stepped out.
He left the door open, so I stepped behind it and peered through the crack to see what was going on. I was shocked to see a big police van with two cops unloading six rather large men in bright orange jump suits from the back. They all stood silently in a line as the hand cuffs were removed. Bob stood silently watching as they were released one by one.
As I peered through the crack, I could see the outline of their meaty cocks through the thin fabric of the jumpsuits. Enjoying its new found freedom, I felt my cock spring to life almost immediately as I examined the outlines. I looked down and watched as my cock grew quickly and poked out proudly from its lacy covering. It was odd watching my cock get hard after getting so used to seeing a pussy when I looked down. I smiled, gripped it firmly and reacquainted myself with my manhood. I marveled at how good it felt in my hand as I stroked it gently and peered back out the crack.
The cops loaded up and drove off without a word. Bob was giving the men a stern look as he walked down the line.
"Gentlemen! How long have you been in jail?" he said as he pointed to them.
"8 years, 5 years, 10 years, 3 years, 9 years, 15 years." they responded in turn.
"You've been coming here for three years and you've all done a good job taking care of the grounds. I think it's only fair you get a day off. How would you like to spend the day by the pool?" he asked gruffly.
"YEAH! HELL YEAH!" was the rousing response from the inmates.
"Good... Form a single file line. Walk straight through that door and straight through the house until you get to the pool. On the way don't stop. Don't touch anything. Don't fuck around or you're back outside. Once you get to the pool form another single file line and wait for more instructions." he barked.
Bob stood by the door pointing the way as the guys did as they were told. I was cowering behind the door trying not to be seen. Bob looked down at my hard cock and smiled.
"Stay behind me." he whispered as he followed the men.
I followed close behind him trying desperately to cover myself with the sexy little night gown I was wearing. When we got to the pool the men lined up as instructed. While I cowered behind Bob.
"I don't have any suits, but if you don't mind skinny dipping. You're welcome to use the pool. There's showers, soap and towels right over there. I'll cook some steaks and snacks for you a little later. As a treat, there is two beers for each of you. I wish I had a woman for you, but if you need sex. You're more than welcome to use Jimmy here for whatever you need." he said as he grabbed me by the neck and forced me out in front of him.
"No!" I squealed in terror as he ripped off my night gown.
"As you can see he's not much of a man. So help yourself." Bob sneered as he threw me to the floor in front of the row of inmates.
The men quickly formed a circle around me. Every time I tried to get up. They pushed me back down and jeered at me. Before I knew what was going on. One of the guys grabbed me by the head and stuffed his cock balls deep into my throat. I gagged and tried to scream, but couldn't. I felt so helpless. Within seconds, someone grabbed my hips and stabbed his cock balls deep into my ass. The two of them fucked me franticly while laughing hysterically.
As the abuse continued, the circle of men jeered at what a pussy I was and cheered the other guys on. They laughed and told the guys to hurry up so they could all take a turn. In the back ground I could hear Bob cheering them on as well. Telling them that since I was no good as a man. At least I could be of some use as a cum dump for real men.
Just as I was starting to recover from the attack, I felt my mouth flood with cum. The guy grunted, emptied his balls and laughed about how good I was at sucking cock. Then stepped away. I barely had time to swallow before a new guy immediately took his place and began ruthlessly fucking my mouth. The guy behind me drove deep emptied his balls into my ass and as soon as he was finished with me, stepped away. The next guy stuffed his cock into my cum filled ass, reached around and started stroking my cock. He immediately began to laugh.
"Hey guys... Look at how big her clit is! He must really like this!" he laughed as he continued to stroke it.
Everyone broke out laughing about what a pussy I was. That I was born to be bred like a bitch. How much they wanted to take me back to the prison with them. They laughed even harder when I began to quiver and shake as my orgasm overcame me. The guy fucking me in the ass continued to stroke my cock and fuck me hard as my cum shot out and splashed on the floor. The guys went wild as they watched in delight.
Just as my orgasm was ending, the guy that was fucking me in the ass grabbed my hips with both hands and drove his cock deep inside me. I could feel his cock throbbing hard while he emptied his balls deep in my ass. His cock throbbed so hard inside me I could hardly believe it. Even after all the guys I had been with, I had never felt anything like it before. I could only imagine the pleasure he was feeling. It made me feel so good, I wished I could see the look on his face as it happened.
When he was finished, he stepped away while the guys cheered. A second later another guy hammered his cock into my ass hard and fast. Just as he was getting started, my mouth flooded with cum. I swallowed as fast as I could before he stepped away and another guy took his place fucking my mouth. I sucked hard while squeezing my asshole as tight as possible.
Just as I was starting to enjoy myself. The guy fucking me in the ass blew his load deep inside me. Before he pulled out the guy fucking my mouth dumped his load too. Just as my mouth began to fill with cum he stuffed his cock deep into my throat and I began to gag. Tears welled up in my eyes from the abuse he was giving my mouth and throat. His cock throbbed hard in my throat and I could feel thick streams of man juice shooting down my throat. He fucked my mouth deep and hard for a few seconds before releasing his grip and stepping aside.
The next two guys didn't waste any time. They took their places and ruthlessly began fucking my mouth and ass. I tried to enjoy it, but they were fucking me so hard I could hardly breath or concentrate on squeezing my asshole tight for them. All I could do was let them have their way with me and hope they liked it. Thankfully the last two guys didn't last that long. Before I knew it, they blew their loads, I swallowed and they threw me to the ground.
As I lay there, they laughed when they noticed my cock was still hard. That it meant I liked being man handled by a bunch of stiff cocks. They jeered about how unnatural it was that I liked getting fucked like a girl. That I was sissy, not a man. That I would have been better off if I was born a woman. That way, I would be a slut instead of a cock loving faggot.
While I listened to their insults, I could feel my cock twitching with excitement. I could feel cum dripping from my chin. I could feel cum flowing freely out of my creamy, well used ass. Forming a thick white stream across my freshly shaved ass cheek.
I couldn't help but to accept the truth of what they were saying. It was one thing to have sex with men while I pretended to be a woman. It was another to do it openly as a man. Every time I got hard, the unvarnished truth was easy to see. I was a man that enjoyed being used as a meat hole/cum dump by other men. It turned me on, I loved doing it and I couldn't hide it.
The whole experience made me feel cheap, used and ashamed.
"Hey Pussy Boy!... Why don't you be a good girl and get the guys a beer. I think they've earned it!" Bob barked.
I gave him a hurt look. Got up, went to the fridge and gave each of the guys a beer. The whole time I did that, my half hard cock was dripping long clear threads of pre cum. While thick white streams ran out of my freshly fucked ass, dripped to the floor or ran down my long smooth legs.
As the guys talked among themselves, several of them stripped off their jump suits and jumped in the pool. I felt my cock spring to life while I watched their thick meaty cocks bounce freely. I became lost in a daze as I admired them. I couldn't take my eyes off them as I absently stroked my own hard cock.
I was snapped back to reality when Bob grabbed my ass and started fucking me from behind. Without thinking, I bent over and grabbed the arm of a chair for support. The other guys just sat and laughed as they watched.
"Hey, where did you find him? Is he just some faggot off the street, or did you train him yourself? He seems to love cock." someone asked Bob with a laugh.
Bob gave a big laugh. "This is my daughters faggot boyfriend. I always knew he was secretly a cock sucker, but my daughter swore that wasn't true. But last week she and my wife went out of town and when I went by her house, there he was walking around dressed in her clothes. I called him a pussy, threw him down and fucked the shit out of him. He came so hard, I thought he had epilepsy. After I was done, I told him he was going to give me sex until my wife got back. He giggled, said ok and here we are."
"So he's only been doing this for a week? That's fucking awesome!" the guy laughed as he sat close by and drank his beer.
"I don't know about that.... He's really good at it and he's been a cock loving fool since day one. My guess is, he's been doing it his whole life. Hell, he even told me he loved the sex and wishes he was a girl so he could do it all the time. I thought it was fucked up, but I need sex and he loves cock." Bob said with a nod.
"Yeah, we got bitches like that in prison. Once you break him in, he'll be your bitch for life." the guy chuckled.
Bob drove his cock deep and groaned with pleasure. I involuntarily arched my back and smiled real big as his cock throbbed inside me. He bumped and ground against me while groaning loudly. I couldn't help but to think of the thick white streams spurting out inside me and it made me so hard I couldn't believe it.
"Good Girl" Bob cooed as he relaxed behind me.
I felt that warm satisfied feeling wash over me as he finished relieving his lust.
"He's been a good girl so far, but I don't need a bitch for life. I just need him to put out until my wife gets back." Bob said in a matter of fact tone as he pulled out, pulled up his pants and walked off.
Leaving me bent over a chair with a flushed look on my face. The guy that was talking to Bob laughed and pulled out his hard cock with a smile.
"Awww.... Poor little bitch needs a cock. Don't worry, I got just what you need. Have a seat and take a load." he chuckled as he waved his cock around.
I instinctively straddled his lap, sat down hard and groaned with pleasure as I felt his cock plunge deep inside me. He watched with a smile as I ground my ass into his lap. When I started bouncing he watched with interest as my hard cock bounced against his belly.
"You really do like cock, don't you?" he chuckled.
"Well, um, I, um." I fumbled uncomfortably.
"Don't be shy. I've met a bunch of bitches like you. Just average guys that love cock as much as they like pussy." he smiled.
I looked down and my hard cock made it hard to deny. I sat down hard and began grinding on his cock again.
"Yeah" I admitted sheepishly while blushing brightly.
"Cool. Tell me what you like about it." he said as he caressed my chest and pinched my nipples.
"It's fun. It feels good. I like being able to do everything a girl can do for a guy. It turns me on to make men cum like that. Most of all. I like knowing I'm good at it. Bob says my ass is as good as real pussy." I said with a smile.
"Been a long time since I had any pussy, but it's better than most of the bitches in the pen. You suck dick better than most of them too." he told me while caressing my sides.
I smiled real big at him and began bouncing on his cock hard and fast. Every time I felt him plunge deep inside of me, my cock slapped against his belly. He grabbed my waist and began thrusting into me hard and fast. I groaned loudly and began pinching and playing with my own nipples. I looked around to see that everyone was walking around casually like it was an everyday thing. Bob was cooking steaks while glancing up at me with a smile. The whole thing made me feel so good, I could hardly stand it. I could feel my orgasm building fast. Just as I was about to blow my load the guy sat me down hard and blew his load hard. I had a big smile as I watched him kick and squirm under me. I jerked and quivered with pleasure as that warm satisfied feeling washed over me again.
Once he relaxed, he smiled up at me and told me how good it felt. I relaxed in his lap and told him thanks. We sat like that and talked for another five minute. His satisfied cock buried deep inside me. Then we got up, everyone had steak and potatoes.
Bob told me I was the serving wench. So I just served and cleaned up after they were done.
While I did that the guys called me bitch, slut or whore when they wanted something. They laughed about what an ugly girl I was. That I was so ugly, I could almost be mistaken for a man. How adorable it was that my oversized clit looked just like a cock. Adding to the illusion that I could have been a man. How nice it was that I was born a bitch instead of a man. How useless I would have been as a man. That the only thing a bitch like me was good for was giving real men sex.
After that I fell into my usual pattern as Kitty. Cheerfully sucking cock and letting them fuck me at will. Giving them whatever they wanted any time they needed it. My cock was almost always hard, no matter what I was doing. If I wasn't taking care of a cock. I was staring at the cocks in the pool while the guys went for a swim. Bob watched with a smile the whole time.
After four hours of that, I was having a real good time letting them use me as a man-bitch. It was becoming as natural to walk around naked and let men use me for sex as a man as it was for me to do it as a woman. As long as I was being used as the bitch/woman, I was happy. Judging by the bulge in Bobs pants, he was happy too.
It was just about that time I heard a big truck pull up out front.
"GUARDS!" someone yelled.
Everybody rushed to get dressed and line up. Bob led them out front in a single file line. As the guards stepped out of the truck and opened the back door, I hid behind the door and watched. The guards looked them up and down with a smile. Then he noticed me.
"Who's that behind the door!" he barked.
Bob reached in, grabbed me and threw me to the ground naked in front of the guard.
"He's nothing. He's the bitch." Bob said with a smile.
"So how was it boys? Was he any good?" the guard chuckled.
They all laughed and talked about how much fun they had. How good the sex was. Then they all jumped in the truck and headed off. I was dazed and confused by the whole thing. My mouth hung open in shock and I didn't know what to make of it. I looked up at Bob, he laughed and helped me up. Then led me back inside.
"What just happened?" I stammered.
Bob laughed, led me to a bedroom, ushered me over to and onto the bed. I laid back and spread my legs like I always did.
"Good Girl... They wanted prison sex. They wanted to man handle another man. I knew you would be perfect for it. So I had them get into costume to come over and meet you. You should have heard what they said about you. They loved you and thought you were great. You were exactly what they wanted." he explained as he pulled down his pants.
I couldn't help but to smile when I saw his rock hard cock spring free. He eyed me up and down while climbing on top of me.
"Sorry I was so rough on you at first, but..... Did you have fun?" he asked as he stuffed his cock balls deep into me with one thrust.
"Not at first. But once I got used to it, yeah. Did you like it?" I groaned as he began fucking me.
"Fuck yeah! I loved it! Seeing you do that as Jimmy instead of Kitty was the hottest thing I've seen in a long time. It really drove home all the things I get to do to you. All the things I get to watch your friends do to you. As Kitty, except for the better ass, bigger tits and red hair, you look just like Helen Hunt. Even though she's the best pussy I've ever had... it's always in the back of my mind that she's really Jimmy in disguise. Seeing you in action today made it real for me. Every time I stick it into that hot juicy pussy. I'm getting your puckered little asshole. Every time I see your friends fuck her. They're fucking you in the ass. Fucking you is every bit as good as fucking a real girl. Hell, your friend Jake fucked you for two hours straight and didn't even know it. What could be better? You were fucking GREAT!" he grunted as he fucked me hard.
I wrapped my arms and legs around him and hugged him tight while smiling at the ceiling. Bob continued to hammer his cock into me until he blew his load inside me again. Then he rolled off me with his usual indifference. I felt that warm satisfied rush as I smiled at his softening cock.
"You might want to take a nap. I hooked you up with a 9 to 5 shift later tonight." he told me as he closed his eyes and relaxed next to me.