Keven Jeanne Bardot Feminine Little Bitchboi
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Miss Keven Jeanne Bardot Is SUCH A SISSY! free porn video
I have this one regular who comes in every Sunday night. He never gives me money, because for one thing, he’s just not a trick; and for another, he knows I want him probably more than he wants me. He fucks a lot of strippers at the club next door – in fact he’s even fucked my ex wife. I didn’t tell him that she’s my wife, but I asked him once if he’d ever been with Cherish - that's Dani's stage name - and he said he had. I don’t even know his name, but we’ve been having sex together for over 4 years.
The routine is always the same; he comes in usually between 5 and 6 pm. I have a booth about midway in the arcade – which I chose because anyone coming in or out has no choice but to pass me. Sometimes he comes in and walks right past me without even acknowledging my presence. He walks around the arcade for a while and then go straight for my booth. By the time he gets back I’ll be ready – meaning I’ll have stripped down totally nude – high heels only.
He’s always dressed the same - sweat shorts and a t-shirt with the sleeves cut off, to showcase his big sexy arms. I love watching in admiration, as he gets naked for sex. I play with his muscular hairy legs as he undresses. Once he’s naked he’ll kick back on the bench and I’ll crawl between his legs and start sucking his cock – which is always rock hard, by the way. He has an average size cock - like, 6 inches - and he loves being serviced. He gets the same treatment at the strip club next door, but over there, money is involved. Even if the strippers want to do him for free, you still have to pay to get in the club, pay for some kind of drink, and pay for the private booth. So normally he'll go over there, get all hard watching the nude dancers, maybe get a free nude lap dance, and then come over to the arcade to be with me. And that's not an unusual thing; lots of guys tell me they do that. I expect payment from most men I go with, but what I ask is always going to be less, because I have little overhead.
So anyway, he'll kick back while I blow him and eat him out - did I tell you how much he loooves having me eat out his asshole? Well he does! Then when he's ready, he'll stand up - which I know means he's ready to fuck. I eagerly get up on the bench, facing the wall. I wiggle my nude buttocks as he mounts me and puts his stiffy into my ass, balls deep, and then he fucks the SHIT out of me! He's a rough fuck. I mean, the whole booth is rocking, and I'm squealing like a stuck pig the whole time. He always cums inside of me, and lays on my back for a minute. Then he pulls out, I drop to my knees and suck him clean, and finish with a napkin. And all the while, his cock is still rock hard! I help him with his undershorts and socks, and even tie his shoes. He pats my cheek and then he's gone, leaving me on the floor, stars in my eyes, his semen running out of my fuck hole. He doesn't even bother closing the door when he walks out. Usually there'll be someone outside, checking me out as I sit there, applying a fresh coat of lipstick. Well, I mean, we make so much noise when we fuck that it attracts a lot of attention. Most of the time I get my next trick right away because of that.
When I was locked up I learned about a thing the inmates call "the covered wagon." Depending on the facility, this can be 2 different things. The first experience I had with had with the covered wagon was in an old county jail, where the cell blocks and cells were old school iron bars. This was about a month after I had been turned out as a prison sissy, and I was owned by an inmate everyone called Rock. Cross dressing was not new to me, as I had been doing it off an on since puberty, so I adapted to living as a woman pretty quickly, and because of my small, delicate build, I could actually pass as a female if I wanted to, and that made me very desirable among the horny inmates. I learned that as long as I made plenty of money for my man, my life in the lockup would be fairly secure.
One Saturday, the word went out on the cell block that there was to be a covered wagon in cell 3, beginning at 6 pm, right after evening chow. I asked Rock what it was and he just laughed and said, "You'll see."
There was a young white guy that had been housed on our block about a week earlier. Like me, he was a first timer and totally out of his element. The Aryans had raiped him and sold him to some blacks. They shaved his head and they were pimping him out to all comers. He wasn't any competition for me, because he was no where near as pretty as me, and had no idea how to suck cock. He was totally straight and this was not his thing. He told me he was going to hang himself, but that the blacks were watching him constantly.
Anyway, as soon as evening chow was over and all the trays collected, the guard locked the block and went downstairs to work in intake. The inmates knew that he was supposed to make rounds at least once an hour, and they also knew he probably would not. As soon as he left, they brought the white k** into cell 3. He was naked and his eyes were darting everywhere. He looked like a victim about to be executed. They put him on the bottom bunk, his ass to the bars, and they tied his thighs to the bars, so that it was impossible for him to do more than move slightly. They hung a towel from the bars near the top bunk, and they brought in the guys. I watched as one by one, men stepped up and fucked him in the ass. They had a pair of socks stuck in his mouth so that he couldn't scream, although the noise level on those cell blocks was deafening anyway. This went on for several hours, and every few guys, a black guy would take a rag and wipe the cum from his ass, because it got really sloppy. The next day the k** found his chance and use a sheet to hang himself. He just was unable to adapt. My turn as the star of the covered wagon came a couple of weeks later. And while it was really uncomfortable at times, I reveled in the thought of all those hard men up inside of me. I farted out gouts of cum!
Later, when I was in prison, the cells didn't have bars, so there a covered wagon was basically they hung a blanket from the top bunk, and the feature would go inside naked, and wait as one by one, the men would crawl in for sex. All the money went to the pimp. This type of covered wagon was more civilized than it had been in county, mainly because you weren't tied up and most of the features were hardened prostitutes, like me.
They called me Pretty Pinky in the joint, and I was the closest thing to a woman these men were going to get, and they knew it. Most inmates are not down with homosexuality, and if you suck a dick inside, you will never regain respect as a "man" again. At the same time, most of these inmates are young and in the prime of life, and they are overloaded with testosterone - they need sexual release. That's where the prison sissy comes in. Prison sissies are female substitutes. If a man fucks a sissy, or gets a blow job from a bitch, he can remain secure in his manhood - nobody will judge him. There are sissies of all races in prison, but if you are young, white, and feminine, you will be a star. You will be owned - body and soul - by another human being, make no mistake about that, but you will survive.
In my case I was a total girl. I looked, walked, talked, and sucked cock, like a woman. My man protected me and I supported him. I didn't have to worry about v******e because my man protected me. Yes, there were times that I would receive a beating from him - for whatever reason - but it would not be life threatening. It could be anything from a bitch slapping in the hallway, to a black eye or fat lip. A lot of sissies - me included - felt that walking around with a black eye or fat lip meant that you had a man who felt for you, and it was actually a source of pride. I know it sounds twisted and sick, but in prison, things are twisted and sick. And don't look for help from the staff; they either turn a blind eye, or actively encourage this stuff, because they know that as long as the inmates are getting their freak on - getting sexual release - they are more likely to remain placid, and less threat to the staff. Yes, you could ask for PC - protective custody - but then you get a jacket put on you and you will do hard time. As a sissy I had so much freedom and even respect. Men treated me as they would a woman on the outside.
There has always been a side of me that was heterosexual. So when I reached puberty, and the creeping feelings of homosexuality began to become prominent - in my fantasies at least - it was a cause for angst. Physically puberty brought very few physical changes for me. While most of the boys my age were taking on the appearances of young men - larger jaws, deeper voices, body hair, etc. this was not happening to me. To this day the only real body hair I have is on my pubis and armpits. Honestly, I know women with more hair on their legs than I have. I don't even have to shave my legs! I am very fair skinned and have blonde hair, and even my facial hair is so sparse that all I have to do is pluck the few hairs that sprout up.
Probably the most glaring anomaly that occurred with me physically at the onset of puberty was that I began to develop breasts. This was not gynecomastia, the awkward looking man boobs that some guys have; these were nicely shaped female breasts - tits! I knew girls in my school who would have killed to have tits like mine! But for me this was a horror! My mom took me to a pediatrician who referred me to an endocrinologist. She examined me and ran some tests, and then told my mom that my body seemed to be producing an overabundance of estrogen, rather than the normal testosterone normal for a male of my age. She told us to wait a few years and hopefully the hormone levels would even out. I wanted to have breast reduction surgery but the doctor recommended waiting until I was older. She did, however, write me a note excusing me from PE, which was a blessing, because at least it saved me from the bullying that would have been unavoidable.
So, though my body was betraying me as the male I wanted to be, I was able to maintain a veneer of maleness, enough so as to not be shunned by normal guys my age. But another disconcerting factor was in play; namely, I had thoughts of being a woman sometimes. Initially these thoughts only came about during masturbation. I would find myself fantasizing doing the things to the men in the porn magazines I masturbated to, that the female models were doing! These thoughts would be banished the moment I ejaculated, only to return the next time my little penis got hard.
I hung out with a bunch of guys back then who, like me, were mostly from what they call the wrong side of the tracks. I liked them because they accepted me as a peer. My best friend in the group was a guy named Jerry. He was my age, but he came across as older - mainly due to our physical appearances. Jerry was big and athletic. He was into weight lifting and wrestling, and had recently gotten into body building. He also was going steady with a very hot girl named Darlene. I still had never even had a date with a girl. Due to my physical appearance - I still looked like I was really young - and the fact that I was extremely nervous and shy around girls, they never much went for me.
One time a few of us had been out drinking, and we passed the apartment of some girls we had known in school. They yelled out the window at us and invited us up. These girls were the female equivalent of us. They had these bad reputations as sluts. Had I been sober I would have been very uncomfortable being around them, but the alcohol had taken the edge off. I was sitting in a chair at the kitchen table, and one of them, a girl named Denise, sat on my lap. God knows what happened but - got a hard on! At first Denise didn't notice it because of all the commotion and conversation, but then she stood up for a second, and when she came back down, she landed squarely on my hard dick. She whirled around to face me, her eyes wide with surprise. I was not nervous at all, and I know she would have got my cherry if we had stayed, but for whatever reason we left soon after. Not a word had transpired between Denise and me the whole time. But she was giving me looks all the way out the door.
Jerry and I had both quit school as soon as we were of age, and in the ensuing years had developed very sketchy work histories. Mostly of the time we were unemployed, and thus always on the lookout for a buck. Jerry had developed a friendship with this older guy he had met at the gym, named Ray. He was quite a bit older than us, but he took a real liking to Jerry, and sometimes we'd go to his house and hang out. He was always finding an excuse to get physical with Jerry - like play wrestling - things like that. One day Jerry showed me a lot of money and we went drinking. As the evening progressed, Jerry confided in me that Ray had set him up on a modeling gig, at some old guy's house in the city. He told me not to think he was gay or anything like that but - the old guy - his name was Herbert - liked to photograph young naked guys. "He didn't go near me, or put a hand on me," Jerry was quick to assure me. "I would have knocked his old ass out if he did."
Hearing this news kind of gave me a queasy feeling in my stomach, but later, when I was at home and masturbating, the thought of it made me so horny that I shot 3 consecutive loads of cum! After that I could think of nothing else. Whenever Jerry and I were together I'd bring up the modeling gig - to the point where Jerry began getting pissed off. One day when we were in the city and he pointed out where Herbert lived. I acted nonchalant, but later when I was masturbating, an idea came into my head; maybe I could model for Herbert. I mean, I know I wasn't very manly, but Jerry had told me that he had seen a lot of Herbert's work, and a lot of it involved homosexuals together. Jerry had told me that he was never going back because Herbert had tried to pressure him to pose together with a skinny young guy. Jerry said he almost punched Herbert out, but that Ray had restrained him.
A few days later I took a bus to the city and went to the house that Jerry had pointed out as being Herbert's. I worked up the courage and rang the bell. An old, fat guy answered. I asked him if he was the guy who was looking for models. He looked around and invited me inside. He asked me where I had heard about him and I told him that I knew Jerry. He had a pretty nice crib. He showed me around and took me to a bedroom that he said he used as his studio. It was a bare room with a photographer's backdrop covering one wall. the only furniture was a ratty turquoise old sofa. There were all sorts of lighting equipment, some with little umbrellas. There was an open closet on the right hand side, and I could see dildoes lined up on the shelves. They ranged from small to grotesquely large. One was as thick as a soda can and had rubber spikes all over it. Herbert showed me some examples of his work, ranging from naked cheesecake shots of cute guys, to shots of naked men having sex. I almost jumped when I saw the ones with Jerry, posing totally naked on the ratty sofa. In one shot he had his legs up high and he was spreading his buttocks, several dildoes beside him. "Do you still think that you're interested in modeling for me?" he asked.
Honestly I was a little scared, but also more than a little horny. I assured him that I would be willing to pose. So he suggested that I get undressed so that the could see could see what I looked like. It was with mixed emotions as I stripped naked in the adjoining bathroom. I looked at my delicate body in the mirror - the same body that I so often looked at when I jerked off. What if he didn't like my breasts? I took a small bath towel and wrapped it around my body, up high, the way a woman would do, and I came out. "Let's see what you got, honey," he told me. "Come on - drop the towel."
I did, not knowing what he was going to think, but he exclaimed: "WOW! Are you SERIOUS?? You look like a chick! I'm not into photographing broads," he said, "But one with a dick is an entirely different story! Are you on hormones?"
I shook my head. "So, those are NATURAL? God DAMN! You are cute, Keven! Turn a round, let me see that ass!" I did as he asked and he was, "Oh, KEVEN! We are gonna make some money, honey!"
I ended up staying there for a couple of hours, mainly posing for what Herbert called cheesecake. He asked me if I was a crossdresser, and when I said that I wasn't, he had me try on some lipstick and high heels. He told me that he had a condition that wouldn't allow him to get hard anymore, but that he had wealthy clients who purchased his work. "A lot of them are always asking me for tranny stuff," he said. "I have a few models who are feminine enough to do it but - jesus! Nothing like you, baby!"
He had me walk around in the high heels and lipstick. I had thick blond hair and he teased it up high and sprayed it. The funny thing is, I had no trouble walking in the high heels; it just seemed so - natural - I don't know, for me to walk in heels! "Are you active? he asked. "Do you have sex - have a boyfriend -girlfriend?" I shook my head. "No?? A fucking CHERRY?? Oh, you are just TOO precious, Keven!"
I became one of Herbert's favorite models. My first video was with another model named Carlos. He was a gorgeous black Puerto Rican. Carlos had a way better body than Jerry, and was so fuckin' CUTE too! Herbert said we made a cute couple, with Carlos' dark skin against my pale white body! He put us on the ratty blue sofa and had us make out naked together. As we kissed, Herbert directed me to put my hand around Carlos' big cock, "Squeeze it, sissy," Herbert said. Carlos groaned in pleasure and then Herbert told me to get down between Carlos' big hairy legs, and suck his cock! OMG! I had never sucked a man's cock before! Was I REALLY a queer ?? How could I NOT be??
But I was so horny from all that kissing and I sunk to my knees and took that hard black Johnson into my rouged pouty lips. This was my first blowjob! I had watched enough porn to know what a man expected, and to be honest, I had fantasized so many times about sucking a man's cock, that I knew exactly what to do. I sucked his cock and nuts, and even ate out his ass hole - something I had never even dreamed of doing before! Now here I was, like a woman, giving her hunk release. Carlos wanted to fuck me, but I was scared, so Herbert said we'd save it for next time. So it ended with Carlos slopping my face with so much cum. It was everywhere - hanging in gooey strings from my nose and chin! Herbert did a close up and asked me how I like it. I smiled broadly and gushed: "Oh I LOVE it!" Then I smiled and tinkled my fingers at the camera.
A few weeks later Herbert called me and told me he wanted me an Carlos to do another video, and this time we would fuck. I was nervous, but I knew I couldn't put it off any longer, AND, I also knew I wanted it. Making love and no fucking was getting frustrating for me. Plus, if I had to lose my cherry, why not with Carlos?
When I arrived at Herbert's for the shoot, I was surprised to see about 10 or 15 guys there. "These are our patrons," Herbert told me in answer to my questioning look. Sometimes they like to come in and see how we do it all." Anyway, the room was ready and Herbert put me on the sofa, wearing nothing but heels and red lipstick. It wasn't really uncomfortable, because, though I knew there was an audience, I couldn't really see them as they were standing behind the lights. The Herbert said, "Ready, honey?" I nodded and he said, "OK - ACTION!"
"Hi, everyone! We're here tonight with one of our newest young models, and he - or should I say, "She?" has come here to lose her cherry!" Tell us your name, honey."
"I'm Keven Jeanne," I said, smiling nervously.
"Keven JEANNE! Wow, that's a perfect name for a little bitch like you, isn't it sissy?
"Uh huh," I said.
"So, Keven Jeanne, what are you gonna do here tonight?"
"Suck cock?" I giggled.
"That's right - you're here to suck cock! And what else?"
"Ummm, and get fucked too!
"And how old are you, Keven Jeanne?"
"I'm eighteen," I lied, looking toward the bathroom, where Carlos was standing, naked, stroking his hard cock. I could feel my only little dick -clit -as Herbert called it, getting hard. I wanted him! Herbert had given me a couple of dildoes to take home, to practice with, and now I felt like I could take a real cock inside of me.
"Well, I don't want to keep you waiting honey," Herbert said. "Come on out, Carlos - Keven Jeanne's waiting!" Carlos entered the shot and took my little hand in his big one and I rose up off of the sofa, as we had rehearsed. He pulled me close to him, took me in his big muscles and we kissed deeply - LOTS of tongue and saliva! I sank to my knees and began sucking his cock. He went to the sofa and sat down and I got on the sofa beside him to blow him, in a position that the audience could see. He was feeling of my tits and had a finger in my ass. "You want to get fucked now, don't you Sissy?" Herbert said. "You want that sausage up inside you - huh? Ok. Go to the bathroom and get the tub of Vaseline, I have a feeling you're gonna need it."
I got up and headed toward the bathroom. "Yeah, that's right, girl - sexy, walk sexy, honey - put some wiggle in it!" I wiggled my ass as I went to fetch the grease, holding in delicately in my hand as I returned to the sofa, where Carlos was waiting, stroking his thick hard Johnson. When I got there I leaned over and took his kiss, as he took two fingers and scooped out a generous gob of the grease. As we made out I had my legs spread and Carlos was fingering my cunt, while I played with his hard cock. He got up and pushed me back on the sofa, and raised my skinny white legs up over his broad shoulders. I whimpered in fear as I felt the head of his cock up firmly against the mouth of my anus. Carlos was so big and strong that he had me pinned to the sofa. I screamed in pain as he silently worked his cock up inside of me - and the audience loved it! They were witnessing a young Caucasian twink paying his dues for the first time - getting raiped by a Negro male! If I had been a real woman, I'm sure Carlos would have made me pregnant that night!
I spent the night with Tom! He came by the arcade again on Friday, around 8 p.m. I was busy with a man in the booth, but he waited. When the trick left, Tom came in and we had sex again – twice. He stayed a long time, mainly because we were making love. When I say, "making love," I mean, as opposed to just having sex. Tom is a kisser, and so am I!
When he came in the booth and locked the door behind him, I watched excitedly as he took off all of his clothes. He has such a beautiful body! I was already naked from my last trick, so I sat there and watched him strip off with admiring eyes. I couldn’t keep my hands off his hairy legs! He sat next to me on the bench and took me in those big muscley arms and we began making out. After awhile I straddled facing him and we made out like that, as he teased my cunt with his cock. Finally I got up into a squat, grabbed his hard penis in my hand and lowered myself onto it. Believe it or not, but I am very tight, despite what a lot of people might think. So it took a second to get the head in, but then it just popped in beyond the hard ridge of rectal muscle and slid balls deep up into me.
I began slowly raising up and down and fucking him good. Every time I raised up I squeezed down hard with my ass muscles and milked him. He was groaning in pleasure, his big hands cupping my bare ass, my soft tits in his hungry mouth. And then, on a down stroke he groaned and grabbed my hips, clamping me down on his balls, and I could feel his semen pumping into my fuck hole. I lay on him, my head on his buff chest as we came down from our sex high. We were covered in sweat. Finally I raised up and his semi flopped out of my ass hole. I jumped down onto the floor and got between his hairy legs and took his messy cock into my mouth, bathing it with my saliva and using my tongue to clean him up. After sex we sat around talking and we started kissing again and the next thing I knew, he stood up, took my ankles in his hand, raising my legs up high, and he fucked me again. Afterwards I put on my bikini and walked him to the door. He got me to promise to go with him the next night after work. He told me he’d pick me up at 2 a.m., after his shift.
On Saturday I went to the arcade early, just after noon time. I spent the next 14 hours sucking as much cock and getting fucked by as many men as I could, all the while thinking of Tom. I had been in love before, with my man in prison, and this was a lot like that. Part of me knew I shouldn’t be going out with him, because I was reluctant to start something I couldn’t control. But I REALLY wanted to go to bed with him, and be with him like a wife - even if it was just for one night. When I left the arcade at 2, the strip club next door was letting out, and all the dancers were out there, getting picked up by their boyfriends. I was wearing a cute little frilly short skirt, a halter top, and a pair of high heels. I looked like any other whore out there. Suddenly I saw Tom’s pick up roll up. He jumped out and ran around to where I was and kissed me right there on the street! Then he opened the door for me and took my hand as I got into the passenger seat.
The motel Tom took me to was definitely a step down from Motel 6. It was squalid actually, and run by Indians. Looked like a lot of junkies and street people around there. He reassured me it was necessary because he didn’t want to leave a credit card trail, and that these people would accept cash and no I.D. The room was dirty and had a weird smell, but I’m not particular about things like that. My Filipina ex wife Dani would have walked out on the spot, but not me. Once inside Tom got naked and lay on the bed and asked me to strip dance for him. I watched his dick get hard as I danced and removed my clothes. When I was naked, Tom crooked his finger at me and I got into bed with him. I won’t bore you with the details, but we made hot passionate love all night, several times, and then again in the morning. I woke up around 11 a.m. to feel Tom’s rigid cock up against my crack. When we had been making love Tom told me that he loved me. I felt so sexy and feminine underneath his big body that I sobbed and told him that I loved him too. And I begged him to give me a baby. I know, that’s impossible, of course, but that’s how intense our sex was. We lay in bed, my bare back up against his chest, his big muscley arms around me, so secure, and we talked in the dark. He told me he was in love and wanted to leave his wife. “And what?” I asked. “And marry me?”
He said he did want to marry me, and that if I said yes, he would tell his wife the next day that he wanted a divorce. “But you have to be with me alone, Keven Jeanne,” he said. “No more going to the arcade.” I bit the corner of my lip in the darkness, pretending to be asleep.
So that’s it. I don’t know what to do! I really like my freedom, and Tom wants me to be his exclusively and stay home and be a housewife! Part of me wants that, but another part of me knows I couldn’t stay true to him, and that I’d want to sneak off to be with other men. Tom is really nice, and he treats me like a queen, but I can see that he has a hard side that I’d be afraid to cross once we were married. Our sex life is great, he gives me all the cock I want, but, who knows once we’re married? And I’m a real whore with a capital W! As you can see I’m really conflicted. I called my ex wife Danii to see what she thought, and she said, “If you love him honey, than you should be his wife. But if it’s just an infatuation, than give it time before making a decision.” What do you think sweeties – should I or shouldn’t I?
The routine is always the same; he comes in usually between 5 and 6 pm. I have a booth about midway in the arcade – which I chose because anyone coming in or out has no choice but to pass me. Sometimes he comes in and walks right past me without even acknowledging my presence. He walks around the arcade for a while and then go straight for my booth. By the time he gets back I’ll be ready – meaning I’ll have stripped down totally nude – high heels only.
He’s always dressed the same - sweat shorts and a t-shirt with the sleeves cut off, to showcase his big sexy arms. I love watching in admiration, as he gets naked for sex. I play with his muscular hairy legs as he undresses. Once he’s naked he’ll kick back on the bench and I’ll crawl between his legs and start sucking his cock – which is always rock hard, by the way. He has an average size cock - like, 6 inches - and he loves being serviced. He gets the same treatment at the strip club next door, but over there, money is involved. Even if the strippers want to do him for free, you still have to pay to get in the club, pay for some kind of drink, and pay for the private booth. So normally he'll go over there, get all hard watching the nude dancers, maybe get a free nude lap dance, and then come over to the arcade to be with me. And that's not an unusual thing; lots of guys tell me they do that. I expect payment from most men I go with, but what I ask is always going to be less, because I have little overhead.
So anyway, he'll kick back while I blow him and eat him out - did I tell you how much he loooves having me eat out his asshole? Well he does! Then when he's ready, he'll stand up - which I know means he's ready to fuck. I eagerly get up on the bench, facing the wall. I wiggle my nude buttocks as he mounts me and puts his stiffy into my ass, balls deep, and then he fucks the SHIT out of me! He's a rough fuck. I mean, the whole booth is rocking, and I'm squealing like a stuck pig the whole time. He always cums inside of me, and lays on my back for a minute. Then he pulls out, I drop to my knees and suck him clean, and finish with a napkin. And all the while, his cock is still rock hard! I help him with his undershorts and socks, and even tie his shoes. He pats my cheek and then he's gone, leaving me on the floor, stars in my eyes, his semen running out of my fuck hole. He doesn't even bother closing the door when he walks out. Usually there'll be someone outside, checking me out as I sit there, applying a fresh coat of lipstick. Well, I mean, we make so much noise when we fuck that it attracts a lot of attention. Most of the time I get my next trick right away because of that.
When I was locked up I learned about a thing the inmates call "the covered wagon." Depending on the facility, this can be 2 different things. The first experience I had with had with the covered wagon was in an old county jail, where the cell blocks and cells were old school iron bars. This was about a month after I had been turned out as a prison sissy, and I was owned by an inmate everyone called Rock. Cross dressing was not new to me, as I had been doing it off an on since puberty, so I adapted to living as a woman pretty quickly, and because of my small, delicate build, I could actually pass as a female if I wanted to, and that made me very desirable among the horny inmates. I learned that as long as I made plenty of money for my man, my life in the lockup would be fairly secure.
One Saturday, the word went out on the cell block that there was to be a covered wagon in cell 3, beginning at 6 pm, right after evening chow. I asked Rock what it was and he just laughed and said, "You'll see."
There was a young white guy that had been housed on our block about a week earlier. Like me, he was a first timer and totally out of his element. The Aryans had raiped him and sold him to some blacks. They shaved his head and they were pimping him out to all comers. He wasn't any competition for me, because he was no where near as pretty as me, and had no idea how to suck cock. He was totally straight and this was not his thing. He told me he was going to hang himself, but that the blacks were watching him constantly.
Anyway, as soon as evening chow was over and all the trays collected, the guard locked the block and went downstairs to work in intake. The inmates knew that he was supposed to make rounds at least once an hour, and they also knew he probably would not. As soon as he left, they brought the white k** into cell 3. He was naked and his eyes were darting everywhere. He looked like a victim about to be executed. They put him on the bottom bunk, his ass to the bars, and they tied his thighs to the bars, so that it was impossible for him to do more than move slightly. They hung a towel from the bars near the top bunk, and they brought in the guys. I watched as one by one, men stepped up and fucked him in the ass. They had a pair of socks stuck in his mouth so that he couldn't scream, although the noise level on those cell blocks was deafening anyway. This went on for several hours, and every few guys, a black guy would take a rag and wipe the cum from his ass, because it got really sloppy. The next day the k** found his chance and use a sheet to hang himself. He just was unable to adapt. My turn as the star of the covered wagon came a couple of weeks later. And while it was really uncomfortable at times, I reveled in the thought of all those hard men up inside of me. I farted out gouts of cum!
Later, when I was in prison, the cells didn't have bars, so there a covered wagon was basically they hung a blanket from the top bunk, and the feature would go inside naked, and wait as one by one, the men would crawl in for sex. All the money went to the pimp. This type of covered wagon was more civilized than it had been in county, mainly because you weren't tied up and most of the features were hardened prostitutes, like me.
They called me Pretty Pinky in the joint, and I was the closest thing to a woman these men were going to get, and they knew it. Most inmates are not down with homosexuality, and if you suck a dick inside, you will never regain respect as a "man" again. At the same time, most of these inmates are young and in the prime of life, and they are overloaded with testosterone - they need sexual release. That's where the prison sissy comes in. Prison sissies are female substitutes. If a man fucks a sissy, or gets a blow job from a bitch, he can remain secure in his manhood - nobody will judge him. There are sissies of all races in prison, but if you are young, white, and feminine, you will be a star. You will be owned - body and soul - by another human being, make no mistake about that, but you will survive.
In my case I was a total girl. I looked, walked, talked, and sucked cock, like a woman. My man protected me and I supported him. I didn't have to worry about v******e because my man protected me. Yes, there were times that I would receive a beating from him - for whatever reason - but it would not be life threatening. It could be anything from a bitch slapping in the hallway, to a black eye or fat lip. A lot of sissies - me included - felt that walking around with a black eye or fat lip meant that you had a man who felt for you, and it was actually a source of pride. I know it sounds twisted and sick, but in prison, things are twisted and sick. And don't look for help from the staff; they either turn a blind eye, or actively encourage this stuff, because they know that as long as the inmates are getting their freak on - getting sexual release - they are more likely to remain placid, and less threat to the staff. Yes, you could ask for PC - protective custody - but then you get a jacket put on you and you will do hard time. As a sissy I had so much freedom and even respect. Men treated me as they would a woman on the outside.
There has always been a side of me that was heterosexual. So when I reached puberty, and the creeping feelings of homosexuality began to become prominent - in my fantasies at least - it was a cause for angst. Physically puberty brought very few physical changes for me. While most of the boys my age were taking on the appearances of young men - larger jaws, deeper voices, body hair, etc. this was not happening to me. To this day the only real body hair I have is on my pubis and armpits. Honestly, I know women with more hair on their legs than I have. I don't even have to shave my legs! I am very fair skinned and have blonde hair, and even my facial hair is so sparse that all I have to do is pluck the few hairs that sprout up.
Probably the most glaring anomaly that occurred with me physically at the onset of puberty was that I began to develop breasts. This was not gynecomastia, the awkward looking man boobs that some guys have; these were nicely shaped female breasts - tits! I knew girls in my school who would have killed to have tits like mine! But for me this was a horror! My mom took me to a pediatrician who referred me to an endocrinologist. She examined me and ran some tests, and then told my mom that my body seemed to be producing an overabundance of estrogen, rather than the normal testosterone normal for a male of my age. She told us to wait a few years and hopefully the hormone levels would even out. I wanted to have breast reduction surgery but the doctor recommended waiting until I was older. She did, however, write me a note excusing me from PE, which was a blessing, because at least it saved me from the bullying that would have been unavoidable.
So, though my body was betraying me as the male I wanted to be, I was able to maintain a veneer of maleness, enough so as to not be shunned by normal guys my age. But another disconcerting factor was in play; namely, I had thoughts of being a woman sometimes. Initially these thoughts only came about during masturbation. I would find myself fantasizing doing the things to the men in the porn magazines I masturbated to, that the female models were doing! These thoughts would be banished the moment I ejaculated, only to return the next time my little penis got hard.
I hung out with a bunch of guys back then who, like me, were mostly from what they call the wrong side of the tracks. I liked them because they accepted me as a peer. My best friend in the group was a guy named Jerry. He was my age, but he came across as older - mainly due to our physical appearances. Jerry was big and athletic. He was into weight lifting and wrestling, and had recently gotten into body building. He also was going steady with a very hot girl named Darlene. I still had never even had a date with a girl. Due to my physical appearance - I still looked like I was really young - and the fact that I was extremely nervous and shy around girls, they never much went for me.
One time a few of us had been out drinking, and we passed the apartment of some girls we had known in school. They yelled out the window at us and invited us up. These girls were the female equivalent of us. They had these bad reputations as sluts. Had I been sober I would have been very uncomfortable being around them, but the alcohol had taken the edge off. I was sitting in a chair at the kitchen table, and one of them, a girl named Denise, sat on my lap. God knows what happened but - got a hard on! At first Denise didn't notice it because of all the commotion and conversation, but then she stood up for a second, and when she came back down, she landed squarely on my hard dick. She whirled around to face me, her eyes wide with surprise. I was not nervous at all, and I know she would have got my cherry if we had stayed, but for whatever reason we left soon after. Not a word had transpired between Denise and me the whole time. But she was giving me looks all the way out the door.
Jerry and I had both quit school as soon as we were of age, and in the ensuing years had developed very sketchy work histories. Mostly of the time we were unemployed, and thus always on the lookout for a buck. Jerry had developed a friendship with this older guy he had met at the gym, named Ray. He was quite a bit older than us, but he took a real liking to Jerry, and sometimes we'd go to his house and hang out. He was always finding an excuse to get physical with Jerry - like play wrestling - things like that. One day Jerry showed me a lot of money and we went drinking. As the evening progressed, Jerry confided in me that Ray had set him up on a modeling gig, at some old guy's house in the city. He told me not to think he was gay or anything like that but - the old guy - his name was Herbert - liked to photograph young naked guys. "He didn't go near me, or put a hand on me," Jerry was quick to assure me. "I would have knocked his old ass out if he did."
Hearing this news kind of gave me a queasy feeling in my stomach, but later, when I was at home and masturbating, the thought of it made me so horny that I shot 3 consecutive loads of cum! After that I could think of nothing else. Whenever Jerry and I were together I'd bring up the modeling gig - to the point where Jerry began getting pissed off. One day when we were in the city and he pointed out where Herbert lived. I acted nonchalant, but later when I was masturbating, an idea came into my head; maybe I could model for Herbert. I mean, I know I wasn't very manly, but Jerry had told me that he had seen a lot of Herbert's work, and a lot of it involved homosexuals together. Jerry had told me that he was never going back because Herbert had tried to pressure him to pose together with a skinny young guy. Jerry said he almost punched Herbert out, but that Ray had restrained him.
A few days later I took a bus to the city and went to the house that Jerry had pointed out as being Herbert's. I worked up the courage and rang the bell. An old, fat guy answered. I asked him if he was the guy who was looking for models. He looked around and invited me inside. He asked me where I had heard about him and I told him that I knew Jerry. He had a pretty nice crib. He showed me around and took me to a bedroom that he said he used as his studio. It was a bare room with a photographer's backdrop covering one wall. the only furniture was a ratty turquoise old sofa. There were all sorts of lighting equipment, some with little umbrellas. There was an open closet on the right hand side, and I could see dildoes lined up on the shelves. They ranged from small to grotesquely large. One was as thick as a soda can and had rubber spikes all over it. Herbert showed me some examples of his work, ranging from naked cheesecake shots of cute guys, to shots of naked men having sex. I almost jumped when I saw the ones with Jerry, posing totally naked on the ratty sofa. In one shot he had his legs up high and he was spreading his buttocks, several dildoes beside him. "Do you still think that you're interested in modeling for me?" he asked.
Honestly I was a little scared, but also more than a little horny. I assured him that I would be willing to pose. So he suggested that I get undressed so that the could see could see what I looked like. It was with mixed emotions as I stripped naked in the adjoining bathroom. I looked at my delicate body in the mirror - the same body that I so often looked at when I jerked off. What if he didn't like my breasts? I took a small bath towel and wrapped it around my body, up high, the way a woman would do, and I came out. "Let's see what you got, honey," he told me. "Come on - drop the towel."
I did, not knowing what he was going to think, but he exclaimed: "WOW! Are you SERIOUS?? You look like a chick! I'm not into photographing broads," he said, "But one with a dick is an entirely different story! Are you on hormones?"
I shook my head. "So, those are NATURAL? God DAMN! You are cute, Keven! Turn a round, let me see that ass!" I did as he asked and he was, "Oh, KEVEN! We are gonna make some money, honey!"
I ended up staying there for a couple of hours, mainly posing for what Herbert called cheesecake. He asked me if I was a crossdresser, and when I said that I wasn't, he had me try on some lipstick and high heels. He told me that he had a condition that wouldn't allow him to get hard anymore, but that he had wealthy clients who purchased his work. "A lot of them are always asking me for tranny stuff," he said. "I have a few models who are feminine enough to do it but - jesus! Nothing like you, baby!"
He had me walk around in the high heels and lipstick. I had thick blond hair and he teased it up high and sprayed it. The funny thing is, I had no trouble walking in the high heels; it just seemed so - natural - I don't know, for me to walk in heels! "Are you active? he asked. "Do you have sex - have a boyfriend -girlfriend?" I shook my head. "No?? A fucking CHERRY?? Oh, you are just TOO precious, Keven!"
I became one of Herbert's favorite models. My first video was with another model named Carlos. He was a gorgeous black Puerto Rican. Carlos had a way better body than Jerry, and was so fuckin' CUTE too! Herbert said we made a cute couple, with Carlos' dark skin against my pale white body! He put us on the ratty blue sofa and had us make out naked together. As we kissed, Herbert directed me to put my hand around Carlos' big cock, "Squeeze it, sissy," Herbert said. Carlos groaned in pleasure and then Herbert told me to get down between Carlos' big hairy legs, and suck his cock! OMG! I had never sucked a man's cock before! Was I REALLY a queer ?? How could I NOT be??
But I was so horny from all that kissing and I sunk to my knees and took that hard black Johnson into my rouged pouty lips. This was my first blowjob! I had watched enough porn to know what a man expected, and to be honest, I had fantasized so many times about sucking a man's cock, that I knew exactly what to do. I sucked his cock and nuts, and even ate out his ass hole - something I had never even dreamed of doing before! Now here I was, like a woman, giving her hunk release. Carlos wanted to fuck me, but I was scared, so Herbert said we'd save it for next time. So it ended with Carlos slopping my face with so much cum. It was everywhere - hanging in gooey strings from my nose and chin! Herbert did a close up and asked me how I like it. I smiled broadly and gushed: "Oh I LOVE it!" Then I smiled and tinkled my fingers at the camera.
A few weeks later Herbert called me and told me he wanted me an Carlos to do another video, and this time we would fuck. I was nervous, but I knew I couldn't put it off any longer, AND, I also knew I wanted it. Making love and no fucking was getting frustrating for me. Plus, if I had to lose my cherry, why not with Carlos?
When I arrived at Herbert's for the shoot, I was surprised to see about 10 or 15 guys there. "These are our patrons," Herbert told me in answer to my questioning look. Sometimes they like to come in and see how we do it all." Anyway, the room was ready and Herbert put me on the sofa, wearing nothing but heels and red lipstick. It wasn't really uncomfortable, because, though I knew there was an audience, I couldn't really see them as they were standing behind the lights. The Herbert said, "Ready, honey?" I nodded and he said, "OK - ACTION!"
"Hi, everyone! We're here tonight with one of our newest young models, and he - or should I say, "She?" has come here to lose her cherry!" Tell us your name, honey."
"I'm Keven Jeanne," I said, smiling nervously.
"Keven JEANNE! Wow, that's a perfect name for a little bitch like you, isn't it sissy?
"Uh huh," I said.
"So, Keven Jeanne, what are you gonna do here tonight?"
"Suck cock?" I giggled.
"That's right - you're here to suck cock! And what else?"
"Ummm, and get fucked too!
"And how old are you, Keven Jeanne?"
"I'm eighteen," I lied, looking toward the bathroom, where Carlos was standing, naked, stroking his hard cock. I could feel my only little dick -clit -as Herbert called it, getting hard. I wanted him! Herbert had given me a couple of dildoes to take home, to practice with, and now I felt like I could take a real cock inside of me.
"Well, I don't want to keep you waiting honey," Herbert said. "Come on out, Carlos - Keven Jeanne's waiting!" Carlos entered the shot and took my little hand in his big one and I rose up off of the sofa, as we had rehearsed. He pulled me close to him, took me in his big muscles and we kissed deeply - LOTS of tongue and saliva! I sank to my knees and began sucking his cock. He went to the sofa and sat down and I got on the sofa beside him to blow him, in a position that the audience could see. He was feeling of my tits and had a finger in my ass. "You want to get fucked now, don't you Sissy?" Herbert said. "You want that sausage up inside you - huh? Ok. Go to the bathroom and get the tub of Vaseline, I have a feeling you're gonna need it."
I got up and headed toward the bathroom. "Yeah, that's right, girl - sexy, walk sexy, honey - put some wiggle in it!" I wiggled my ass as I went to fetch the grease, holding in delicately in my hand as I returned to the sofa, where Carlos was waiting, stroking his thick hard Johnson. When I got there I leaned over and took his kiss, as he took two fingers and scooped out a generous gob of the grease. As we made out I had my legs spread and Carlos was fingering my cunt, while I played with his hard cock. He got up and pushed me back on the sofa, and raised my skinny white legs up over his broad shoulders. I whimpered in fear as I felt the head of his cock up firmly against the mouth of my anus. Carlos was so big and strong that he had me pinned to the sofa. I screamed in pain as he silently worked his cock up inside of me - and the audience loved it! They were witnessing a young Caucasian twink paying his dues for the first time - getting raiped by a Negro male! If I had been a real woman, I'm sure Carlos would have made me pregnant that night!
I spent the night with Tom! He came by the arcade again on Friday, around 8 p.m. I was busy with a man in the booth, but he waited. When the trick left, Tom came in and we had sex again – twice. He stayed a long time, mainly because we were making love. When I say, "making love," I mean, as opposed to just having sex. Tom is a kisser, and so am I!
When he came in the booth and locked the door behind him, I watched excitedly as he took off all of his clothes. He has such a beautiful body! I was already naked from my last trick, so I sat there and watched him strip off with admiring eyes. I couldn’t keep my hands off his hairy legs! He sat next to me on the bench and took me in those big muscley arms and we began making out. After awhile I straddled facing him and we made out like that, as he teased my cunt with his cock. Finally I got up into a squat, grabbed his hard penis in my hand and lowered myself onto it. Believe it or not, but I am very tight, despite what a lot of people might think. So it took a second to get the head in, but then it just popped in beyond the hard ridge of rectal muscle and slid balls deep up into me.
I began slowly raising up and down and fucking him good. Every time I raised up I squeezed down hard with my ass muscles and milked him. He was groaning in pleasure, his big hands cupping my bare ass, my soft tits in his hungry mouth. And then, on a down stroke he groaned and grabbed my hips, clamping me down on his balls, and I could feel his semen pumping into my fuck hole. I lay on him, my head on his buff chest as we came down from our sex high. We were covered in sweat. Finally I raised up and his semi flopped out of my ass hole. I jumped down onto the floor and got between his hairy legs and took his messy cock into my mouth, bathing it with my saliva and using my tongue to clean him up. After sex we sat around talking and we started kissing again and the next thing I knew, he stood up, took my ankles in his hand, raising my legs up high, and he fucked me again. Afterwards I put on my bikini and walked him to the door. He got me to promise to go with him the next night after work. He told me he’d pick me up at 2 a.m., after his shift.
On Saturday I went to the arcade early, just after noon time. I spent the next 14 hours sucking as much cock and getting fucked by as many men as I could, all the while thinking of Tom. I had been in love before, with my man in prison, and this was a lot like that. Part of me knew I shouldn’t be going out with him, because I was reluctant to start something I couldn’t control. But I REALLY wanted to go to bed with him, and be with him like a wife - even if it was just for one night. When I left the arcade at 2, the strip club next door was letting out, and all the dancers were out there, getting picked up by their boyfriends. I was wearing a cute little frilly short skirt, a halter top, and a pair of high heels. I looked like any other whore out there. Suddenly I saw Tom’s pick up roll up. He jumped out and ran around to where I was and kissed me right there on the street! Then he opened the door for me and took my hand as I got into the passenger seat.
The motel Tom took me to was definitely a step down from Motel 6. It was squalid actually, and run by Indians. Looked like a lot of junkies and street people around there. He reassured me it was necessary because he didn’t want to leave a credit card trail, and that these people would accept cash and no I.D. The room was dirty and had a weird smell, but I’m not particular about things like that. My Filipina ex wife Dani would have walked out on the spot, but not me. Once inside Tom got naked and lay on the bed and asked me to strip dance for him. I watched his dick get hard as I danced and removed my clothes. When I was naked, Tom crooked his finger at me and I got into bed with him. I won’t bore you with the details, but we made hot passionate love all night, several times, and then again in the morning. I woke up around 11 a.m. to feel Tom’s rigid cock up against my crack. When we had been making love Tom told me that he loved me. I felt so sexy and feminine underneath his big body that I sobbed and told him that I loved him too. And I begged him to give me a baby. I know, that’s impossible, of course, but that’s how intense our sex was. We lay in bed, my bare back up against his chest, his big muscley arms around me, so secure, and we talked in the dark. He told me he was in love and wanted to leave his wife. “And what?” I asked. “And marry me?”
He said he did want to marry me, and that if I said yes, he would tell his wife the next day that he wanted a divorce. “But you have to be with me alone, Keven Jeanne,” he said. “No more going to the arcade.” I bit the corner of my lip in the darkness, pretending to be asleep.
So that’s it. I don’t know what to do! I really like my freedom, and Tom wants me to be his exclusively and stay home and be a housewife! Part of me wants that, but another part of me knows I couldn’t stay true to him, and that I’d want to sneak off to be with other men. Tom is really nice, and he treats me like a queen, but I can see that he has a hard side that I’d be afraid to cross once we were married. Our sex life is great, he gives me all the cock I want, but, who knows once we’re married? And I’m a real whore with a capital W! As you can see I’m really conflicted. I called my ex wife Danii to see what she thought, and she said, “If you love him honey, than you should be his wife. But if it’s just an infatuation, than give it time before making a decision.” What do you think sweeties – should I or shouldn’t I?
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