How I Got My Degree In Transsexual Prostitution free porn video

How I Got My Degree in Transsexual Prostitution By Tina Crawford ([email protected]) Timing. Timing is everything these days. Some people have great timing. Those that pick just the right lotto card, or just miss a head on collision. Others have lousy timing, and I sadly find myself in that latter boat. My timing is terrible and eventually it finally took its toll on me. Let me explain. My name is Stan and I am a sophomore at a smaller Midwest college. My life was pretty normal, good grades, staying out of trouble, etc. I really had no social life, and zero friends but I was relatively happy and stayed sane be watching movies and surfing the net. This year I had a roommate named Tony. My previous roommate dropped out this summer so I found myself rooming with Tony. He was a nice guy more or less and what women would call sexy. He had a broad smooth chest, no body hair I could ever see and pretty built muscles. I've seen him naked a time or two (without his knowledge of course) and he's just as sexy. He has a good 9 inch cock and some heavy round hairless balls. He does have a nice tight ass and nice lean legs. Now I'm not gay but I do think I may have some bisexual tendencies. I also cross-dress which may explain the first statement. I've dressed off and on since the beginning of high school and I love it. The feel and look of sexy, lacey womens' underwear makes me hot. I love the way I feel when I wear some satin panties or silk stockings and a garter belt. I also love shoes. Heels, boots, Keds, tennis shoes I love them all. I try to dress whenever I can but living with another person kinda buts a damper on things so I don't get to play nearly as often as I'd like. Life in college was going along pretty normally for the first few months. I saw very little of Tony as he was always out. He would come home late each night and go straight to bed. He was a physical therapy major so I never had him in any of my biology classes. When we did see each other we talked politely. I usually spent most of my talking time with him giving him messages from a few of his friends. They were always calling for him almost all day long sometimes. Most of the calls were from guys Tony knew, but there was this one girl, Jennifer, that called almost daily. She had a very sexy voice and was always nice to me on the phone. She would ask me to tell Tony she was home and that was it. If and when Tony did come back to the room he would practically run out the door as soon as I would tell him the message. After a few weeks I started to assume that Jennifer was Tony's girlfriend. It seemed to make sense. Anyway one weekend Tony said he was going to go home and visit his folks. I wished him a safe trip and with that he was off. Finally I was alone for a few days. I practically jumped to the box under my bed that had my crossdressing stuff in it. I forced myself to wait a few hours before I began to get dressed, just in case Tony had forgotten something and came back. After 2 hours I could wait no longer and I quickly stripped out of my shorts and shirt and dove into the box. First I took out some red nail polish and proceeded to paint my toenails. While they were drying I applied the same polish to my fingernails. After waving my hands around to air dry them, I began to get dressed. First I pulled on a black lace garter belt and fastened it around my waist. Next I slowly and sensuously pulled on a pair of black silk stockings with a bit of lace on the top. I loved the feel of the nylon against my skin and instantly my cock was hard from the sensation. I secured the stockings to my garter straps and moved on to the next step. I selected a nice red and black lace bustier and put it around my chest. I wiggled and squirmed a bit but finally got the clasps to fasten. I then stuffed the empty bra cups with some pantyhose and reached for a pair of red satin panties. I slowly pulled them up my legs loving the feeling of the satin against the nylon. I stood up and pulled the panties over my ass and around my rock hard cock. Now I'm not very big, even when erect, but I made a huge bulge in those panties the instant I pulled them to my waist. I then fished out a pair of 3 inch red high heels and stepped into them. I teetered on them for a few moments before I regained my "heel legs" and began to walk around the room. I retrieved a small makeup kit from the box and walked over to the full length mirror on the back of our door. I applied a little blush and eyeliner and finished it off with a nice shade of red lipstick. I then stared into the mirror for a long while striking various poses and generally turning myself on looking at myself in drag. I then went over to my VCR and popped in a shemale tape I had recently bought. Soon the TV was filled with images of various transsexuals getting fucked up the ass as their cocks and tits bounced from the thrusts. My cock was starting to leave a little wet spot in my panties as I sat in a chair watching the ass pounding take place. I started to lightly stroke my cock through the material when the phone rang. I nearly jumped out of my skin when it rang. I quickly got up and walked over to the phone. I said hello and was rewarded with the sound of Jennifer's voice. She asked if Tony was there and I told her that he said he was going home for the weekend. She sounded a little annoyed and asked if he had left her school bag there. I looked around and spotted a blue nylon bag sitting on Tony's top bunk. I asked if it was hers and she said yes. She then asked if she could come over to get it since she was in this part of campus and really needed her Psyche book. I started to panic. Here I was dressed in drag, including makeup, and now Tony's girlfriend wants to come over. I quickly stammered that I was just about to jump into the shower, and that she could come over in like half an hour or so. She again sounded annoyed but agreed. I hung up the phone and literally tore off my clothes. I jammed all my stuff back into their box and tossed it under my bed. I then threw on my male clothes and ran down the hall to the shower with a bottle of nail polish remover. I thanked God that I didn't see anyone on the way as I turned on the water and jumped in. I quickly scrubbed my face with a washcloth trying to wash away the makeup. After several minutes of scrubbing I then practically dumped the whole bottle of polish remover on my hands and started to rub the red off my nails. After a few minutes I got as much of it off as I could and I turned off the water. I hurriedly dried myself off and ran back to my room. I got in and changed into some clothes just as I heard a knock at the door. I took a deep breath and opened the door. There before me was one of the most beautiful girls I have ever seen. She had a face like a goddess and a body that most men would kill for. She looked to be about 5'8", she had long sexy red hair, a nice 38C or D size chest and a lean and sexy body. She was wearing a really tight white shirt which came to just below her tits and showed off her belly and pierced belly button. You could see her tight black bra through the shirt and she was wearing skin tight cut off jean shorts that ended just below her ass. She had sexy smooth long legs that ended in cute little white socks and a really nice pair of white and teal Nike shoes. I did a double take before my power of speech kicked back in and I asked her in. She said that she had left her bag in Tony's car and that he was supposed to have returned it before he left town, but obviously he had forgotten. I showed her where it was. She thanked me for letting her come get it and then as she looked at me a quizzical look came over her face. I asked her what was wrong and she said that my cheeks looked flushed and was I feeling ok. Shit, Shit, Shit is all that rang through my head. I must have not gotten all the blush of my cheeks. I quickly told her that I was fighting a cold and that I did feel a little hot. She suggested that I should lie down for a nap or something and I told her I would, desperately trying to get her out of the room. Suddenly I had the feeling that she didn't want to leave as she began to walk around the room looking at everything. She said that it was the first time she had been to Tony's room, that he always went to her dorm room. She asked which bunk was his, which closet he kept his clothes it, etc. I began to really wonder what the hell she was up to when my VCR shut itself off. I have a newer model VCR and if it sits powered on not doing anything for thirty minutes it shuts itself down to save power. Well it decided now was a good time to sleep and it shut itself off, ejecting its tape and making a loud noise at the same time. Both our heads turned to the VCR and in a matter of seconds a black tape with the rather bold and easy to read words "Shemale Ass Pounders" popped into view. If my cheeks weren't red before they certainly were now as I quickly turned to see if Jennifer had seen the tape. To my dismay she was looking right at the machine and without saying a word went over to my door, shut it, and engaged the lock. My heart was beating in triple time as she slowly turned around and walked back over to me. She sat down in the chair and just stared at me. My face was on fire, my heart pounding, and my body shaking, as she looked me up and down. Finally she asked me to sit down and as I did she asked if the tape was mine. Not knowing what else to say I told her it was. She then asked if I really liked that sort of thing and again I answered yes. She then pointed to my cheeks and asked if I was wearing makeup. I just nodded. She then stared at me some more and asked me to play the tape. I reluctantly got up and turned the VCR back on. I then pressed play and again the room was filled with the sounds of shemale asses getting pounded. She asked me if I was getting hard watching this and I became aware that there was a now painfully hard bulge in my jeans. I told her that I was excited. She asked if I also liked to wear women's clothes and I lowered my head and muttered that I did. This seemed to make her very excited. She told me that in order for her not to tell Tony, or anyone for that matter, that I would have to do some things for her. I asked her like what and with that she walked over to me and smiled. She told me that she would be back in a half an hour and that I had better be dressed like a good little girl or she would tell everyone on my floor that I was a cross-dressing sissy. She then kissed me on the cheek and left the room. I stood there dumbfounded for a few minutes before the reality of it all kicked in. And to my amazement I found myself opening my box up and getting dressed again. In 20 minutes I was all fem again just as I had been a half an hour earlier, right down to the nail polish and makeup. My cock was hard and my heart was pounding. A few minutes later there was a soft knock at the door and I looked out the peephole. There was Jennifer. She was alone so I quickly opened the door and let her in. She strode inside like she owned the place and told me to stand in front of her. She spent the next few minutes looking me over from every angle before she invited me to sit down and talk to her. She told me she wanted to know more about me and asked me to tell her about my cross-dressing. I found that the longer I talked about it the easier it got and soon the words were flowing from me like a stream. I told her how it started in high school. How I love feeling like a woman. My fetish for shoes. I told her everything. She asked if I was gay and I told her no. I then added that I might be bisexual but that I still found women attractive. She then asked if I thought she was attractive and I told her yes. She smiled and with a chuckle asked if I found her or her clothes the most attractive. I blushed and didn't answer her. Finally she seemed satisfied with my story and she told me to get up. She then produced a small digital camera and before I knew it began to take pictures of me. I started to protest when she told me to behave or that she would scream. That shut me up and I let her take her photos. She then used my computer to upload them and email them to herself, for protection she said. Now I was technically hers. She said that she owned me now and unless I wanted the entire school to know, I better do what she said. I sat down bewildered from the whole thing. She sat next to me and told me that she had her suspicions about me. She said that Tony had mentioned that he thought I might be gay or something, that he had spotted me watching him change a few times. He also said that he thought I might be into wearing girls clothes based off some pics he found on my computer one time. I didn't even know he used my computer when I wasn't home! Jennifer told me that Tony wasn't all that he seemed to be himself. She said that he too was her slave of sorts. That he lived to worship her and that he would do anything she asked. She also said that he too was very bisexual almost to the point of being out and out gay. I never would have pictured Tony being gay but the thought of it started to make me hard. Jennifer noticed that and she made a point of asking me if I thought Tony was sexy. I said that I thought he had a nice body and that I liked the way he looked naked. She smiled and told me that in a few days she would arrange for me and Tony to have some fun at her direction. I started to ask her what she meant when there was another knock at the door. I started to panic but Jennifer told me to stay put as she went to answer the door. I heard her talking to someone and the next thing I know she walks in with some guy. I turned beet red and tried to cover myself the best I could. Jennifer laughed and told me to stop that. She then introduced the guy as Andy and told me that he was a raging homosexual. Andy laughed at that and then began to look me over. He turned to Jennifer and told her that I would do. He handed her a bag he was carrying and then proceeded to sit next to me on the bed. I looked at Jennifer and saw her pulling a camcorder out of the bag and pointing it at me. She then told me that I was to make out with Andy and do whatever he wanted me to do, except that he couldn't fuck me in the ass. She said she was saving that part of me for a special occasion. I was panicking inside as she started to record and Andy put his hands on me. Soon he began to feel my legs and arms which to my surprise started to make me hard. He noticed my bulge and put his hand on it. I nearly climaxed as he slowly rubbed the satin up and down my cock. He then turned to kiss me and then we were locked in a french kiss. He continued to rub me with his one hand as he explored my body with the other, all the time never breaking off his kiss. Gradually I began to respond to his manipulations and found myself really enjoying it. Soon I totally forgot Jennifer and I started to rub my hands all over him. I worked him all over and when I got to his crotch I felt a huge bulge waiting for me there. Andy smiled and told me that I had done that to him. He then laid me down on the bed and kissed his way down to my panties. In one gentle motion he started to pull them down my legs and soon my rock hard cock sprang free from its satin prison. Andy wrapped his strong hands around my hot dick and soon I felt him kissing my head. It was a wonderful feeling. Inch by inch he swallowed my cock until my entire length was enclosed in his hot mouth. Up and down he went sucking my shaft getting me hotter and hotter. In between sucks Andy began to pull his own pants down and soon his raging 8 inch cock sprang free. He began to work his meat up and down in time to his sucking of my cock. After several minutes of that and his hand caressing my balls I felt myself nearing orgasm. I told him that I was going to cum and he said he was ready. Three strokes later I erupted into his mouth in a series of milky bursts. Andy continued to suck unabated swallowing all I could give him and then sucking my cock for more. It was one of the most intense orgasms of my life. I just laid there as my cock began to go soft in his mouth. Finally he pulled away from me and started to get up. He said he was close and he quickly moved to my face. Before I knew what was happening, he grunted and I felt gobs of his hot cum hit my face. I let out a scream as more and more of his cum spurted onto my cheeks, chin, and mouth. After what seemed like days his spurts finally stopped and he slowly milked his cock for what was left. He began to rub his softening cock all over my face, smearing his cum in the process. When he finally was soft again he gave my cock a quick squeeze and then he silently got dressed, kissed Jennifer on the cheek, thanked her for the good time, and left the room. I laid there exhausted and confused as Jennifer stopped the camcorder and put it back into its bag. She then told me that I had done a very good job and she hoped I had enjoyed it because it was going to become a regular way of life for me. And with that she said she was leaving, that she would call me the next day. She kissed me goodbye and left me to sit in my afterglow and cum-bath wondering what the hell I had gotten myself into. I spent the whole next day anxiously pacing by the phone (well as much as you can pace wearing 3 inch high heels). Finally at around 3pm the phone finally rang and I pounced on it after only one beep. It was Jennifer. I found myself instantly hard the second I heard her say hello. She instructed me to come visit her at her dorm room. She told me what building and her room number and added that I should wear my male clothes over but to not get too comfortable in them. And then with an evil giggle she hung up. I quickly changed into some jeans and a shirt and found myself hurrying out the door. Jennifer lived in the more upscale dorm on campus and on the 3rd floor, which meant she had one of the single suites. Those were very expensive and big compared to my room. I had seen them on the tour I had gotten before I came here. They had a huge bedroom, a bathroom, a small kitchen and a den like room at the center. A very nice room indeed especially since it was designed for only one person. After a short shuttle bus ride I found myself in front of her dorm. I entered it and took the elevator up to the 3rd floor. Nervously I walked up to Jennifer's room and knocked on the door. My heart was pounding fast as the door opened and Jennifer appeared. My throat suddenly went dry and I could only blush at her as she gave me a wink and invited me inside. The place was huge, bigger than I remembered on the tour. She led me into the den room and told me to sit down. As I sat on a semi leather couch she handed me some pieces of paper. I glanced through them and to my surprise they were digital pictures of me! Some were from when she had taken pictures of me posing, but most were of me and Andy making out on my bed. The final picture was of my cum covered face and Andy's big cock rubbing it all over my cheeks. My face was contorted into what looked like pure passion. To say I was shocked was an understatement. Jennifer read the look on my face and before I could respond asked me if I knew what blackmail was. She told me that she had MORE than enough stuff on me to embarrass the hell out of me if I didn't do what she said. She told me that she had shown the pictures and the video to a few of Andy's gay friends and they all wanted me. My insides were shaking like a leaf and I just stared at Jennifer with a rather dumb look on my face. She walked over to me and kissed me on the lips. She then smiled and told me that if I did what she asked without any kind of trouble she would make my life very pleasurable. She then asked me if I understood what she expected of me and I found myself nodding yes. Her smile got even bigger and she pulled me off the chair and into the bathroom. She pointed at the shower and told me to lather myself up with what was in a big white bottle she handed me. She warned me not to get any of it above my neck or on my face or head. Then when I was done she said she wanted me to clean myself up and wash with the scented shampoos and soaps she had on the sink. Then I was to put on the pink fluffy robe hanging on the back of the door and meet her in her bedroom. She then patted my ass and left the room. I wondered to myself for like the hundredth time what the hell I had gotten myself into. I then stripped out of my clothes and got into the shower I opened the big white bottle and squirted some rather smelly blue liquid onto my hands. Slowly I rubbed the mystery liquid all over my body from my toes up to the top of my neck. I made sure every inch of my body, including ass and crotch were covered. I felt a rather strange but not unpleasant tingle on my skin. Finally after like five minutes I turned the shower on and began to rinse myself off. As the lather slowly flowed off me I let out a small scream. My body hair was washing off with it! In a mater of seconds I was COMPLETELY hairless from the neck down. Not a single hair remained on my legs, arms or even my balls. I almost started to hyperventilate from the shock when Jennifer knocked at the door and asked if I was ok. I eked out that I was hairless and she giggled. She told me to hurry up and wash up that she was waiting. Still shaking from my ordeal I quickly began to shampoo my hair with a pleasant apple scented soap. I then continued with an equally sweet smelling body wash and lotion. As I rubbed the soap all over my body I noticed that I really enjoyed the feeling of being hairless. I felt so smooth and sleek. My balls really felt neat being so smooth. My cock was rapidly getting hard as I made lazy circles over my body. Soon I was clean top to bottom and I got out of the shower. I dried myself off and put on the fluffy pink bathrobe. I looked around and noticed my clothes were missing. I again started to panic when I heard Jennifer call my name. I reluctantly and nervously walked out of the bathroom and down the hall to her room. I walked in and she was waiting for me with a big smile on her face. She told me to take off the robe and after a few seconds I slid it off, standing completely naked before her. She again walked around me looking at me from all angles. Then she slowly put her hands on me, feeling my ass, my legs, and finally stopping at my cock. She looked me straight in eyes as she gently squeezed and played with my now smooth cock and balls. It wasn't long before I was hard again. It felt so good as she applied steady pressure to my cock and rolled my balls around in her hand. She finally stopped staring at me and looked at my dick. She kinda giggled and told me that I wasn't very big, but that she guessed that she could live with that. She then grabbed my cock and pulled on it using it like a leash. She led me to the bed and told me to get dressed with the clothes she had laid out. She then left the room as I got dressed. On the bed were some very pretty lingerie and some downright sexy boots. I eagerly and erectly started to get dressed. I put on a fire red bustier with dangling red garter straps. After clasping it around my chest I checked the fit. It looked like it was designed for an A cup because the material fit pretty snug to my body with little room for the padding I would usually put in the cups. I then sat on the bed and drew a very sexy pair of black silk stockings up my legs. I just reeled in the feeling of the silk on my now smooth legs. It was so much better than I had ever felt before. I caressed my legs for a while before I fastened the garter straps to them both front and back. Next I picked up a pair of red satin panties and pulled them up my legs. Again the feel of the smooth slippery material against my now smooth body was wonderful. Finally I was ready for the shoes. I got harder (if that was possible) when I picked up the ankle high spiked heel boots I was to wear. They had what looked like a good 4 inch heel to them and they were very shiny. I slipped my feet into them, and after a bit of wiggling I got them on and zipped up the sides. They were a bit snug but they fit. I slowly stood up and tottered around a bit before I got used to walking in them. Soon I was wandering around the room enjoying the feel of the garter straps pulling on my stockings, the feel of the silk and satin rubbing against my body and the wonderful feminine smells coming from the room and myself. Shortly Jennifer returned and applauded my skill at getting dressed. She said I looked sexy and I blushed from the compliment. She them led me to her vanity and told me to sit down. She turned me away from the mirror and began to work me over with some makeup. I could only stare at her as she opened a bottle of this, brushed that onto my face, painted me with this, and dabbed me with that. She whispered to me that I was a pretty girl and that she was making me even prettier. She told me that she was not an evil person, and even though she had to blackmail me to get me to do this, she knew deep down that I LOVED every minute of it. She said that I probably could never admit it to myself that I was happier being a girl. Her hushed tones and insights soothed me and I found myself relaxing more and more. She said that she really was a nice person and that she only wanted me to be happy. Soon she stopped tweaking my face and told me to look in the mirror. As I turned to face myself my jaw dropped in astonishment. Before me sat a very pretty young girl. She had some mannish features to her, but all and all she looked very lovely. I found myself thanking Jennifer for making me look so pretty before I realized what I was saying. She laughed and kissed me on the lips. If felt strange to kiss a girl while wearing lipstick, but I liked it none the less. She told me that a pretty girl should have a more feminine name than Stan. I again blushed and told her that when I dressed I liked to call myself Tina. She smiled and said that she thought Tina was a very pretty name. She told me that I was a goddess and she then opened a drawer on her vanity and pulled out a jewelry box. She picked out a nice pair of clip on earrings, a cute gold chain with a gold heart hanging from it and a small gold ring for my hand. She then went to her desk and picked up her digital camera. We then spent the next half an hour posing me in various sexy ways and her snapping shots. I was really starting to get into it when the phone rang and she told me to sit down while she talked. I could only hear her side of the conversation but she spoke in a whisper so I couldn't really make it out. She finally hung up from whomever she was talking to and sat next to me on the bed. She said that she wanted me to trust her. And to achieve that result she wanted to tell me about her and her plans for me. She said that when she was sixteen her boyfriend raped her one night after a party and she ended up pregnant. Her daddy was a very powerful and rich lawyer for the state of Texas and he saw to it that the boy spent the next few years of his life suffering in jail. But being the god loving people they were, Jennifer was forbidden to have an abortion. Her pregnancy progressed normally over the course of the next 9 months. But at the same time she also began to develop a relationship with her best friend April. It had started with simple making out and truth or dare touches at sleep-overs but as she got bigger, April became bolder. Finally by Jennifer's fourth month, they had begun to sleep together. She told me that it was April that had helped her get through all the pain and emotion of her rape and pregnancy. And she said that she truly loved April like she had never loved anyone else. As her pregnancy progressed her breasts slowly began to produce milk. And within days April became addicted to it. Every day April would latch herself onto Jennifer's tits and suck the sweet milk from them. Combined with her expert tongue and fingers on Jennifer's pussy, it gradually became very sexually exciting to have April milk her. This continued until the day Jennifer gave birth. She didn't really want the baby and she felt she couldn't raise it properly herself. So together she and her daddy decided that she should put the baby up for adoption so some other family could take care of it and love it. After the birth and Jennifer returned home she found that she was still lactating. After a long talk with April, and some researching on the Internet, she found out that as long as the practice of milking continued, her body would keep producing milk. So ever since then Jennifer has let April, and a handful of other people, milk her wonderful tits everyday to keep them producing. She said that it has developed to such a point that she can orgasm just from milking alone. I sat there just absorbing the story when I heard someone enter the room. I looked up and saw another beautiful girl standing in the doorway. She was about the same height as Jennifer but with long light brown hair. She had an innocent face, pretty in its own way. She too had a damn sexy body and big 38 D breasts. Her legs were smooth and long as well but she had a rather pudgy belly which was emphasized by the tight white shirt she wore. I again blushed deep red as Jennifer got up and ran over to the girl. They began to embrace in a french kiss and I knew this had to be April. After several hot minutes of their tongue wrestling both girls broke it off and turned to me. Jennifer introduced the girl to me as April and soon both women were sitting next to me. Jennifer, holding April's hand, continued with her story. She told me that her daddy would do anything to make her happy so when she said she wanted to go to college he paid for her to have the most expensive room on campus. She explained that April wasn't in college but lived with her here in the room as her lover. I finally got up enough courage to ask her about Tony, and I told her that I thought he was her boyfriend. Both girls laughed and Jennifer said that boy-toy was closer to the truth than boyfriend. She said to make a long story short after her freshman year she could no longer bear to keep the truth from her daddy and she finally came out of the closet and told him she was gay and in love with April. He apparently went off the deep end, cut her off financially and did everything but disown her. She said that it's been over half a year since she's talked to him. I then asked her how she paid for this dorm room without her daddy and again both girls giggled. She told me that she whores Tony out as a gay prostitute and uses the money she makes off him to pay for college. I sat there astonished as she told me that. She went on to say that it first started off simply as a business arrangement. Tony had the hots for Jennifer and once he got used to milking her tits she began to notice she had some power over him. Gradually as she and April let Tony fuck them he fell under their spell. He would do almost anything for them, and when they asked him to have sex with a gay friend of theirs he jumped at the chance. So fast forward a bit and now Tony is their utter sex slave doing whatever and whomever they command. Jennifer then said that both she and April grew to like Tony and therefore allowed him to help April in a very special way. I asked what that meant and Jennifer proceeded to lift up April's shirt and pat her belly. She told me that she wanted April to feel the sexual pleasure of milking as she had so they allowed Tony to impregnate April. They are going to give the baby up for adoption and continue to milk April the rest of her life, just like Jennifer. She then added that you wouldn't believe what some guys, and girls, would pay just to suck your milk filled tits. I sat there a few minutes digesting what I was told as Jennifer slowly rubbed April's belly up and down. Finally I asked what role I was to play in all this. Jennifer stopped teasing April and took both my hands in hers. Looking me straight in the eyes she told me that I was also to become their prostitute. That they were going to charge guys a shit load of money to allow them the chance to have sex with me. I just sat there pale and unblinking. Jennifer then continued by telling me she could get a lot more money off me than she ever could from Tony. She explained that even though Tony was hot, he still was just a normal guy. But me, I was a sissy cross-dresser. Gay men would pay a fortune to have a night with my small cock and tight ass all dressed up in sexy female clothes. She then told me that Andy had paid her $200 dollars just to suck me off and blow his load all over my face. And that his friends, the ones she showed my picture too, all wanted a chance to fuck me. I was to be their little cash cow ringing up assets in a very literal sense of the word. As this news began to sink in Jennifer also told me that besides whoreing Tony out, and letting people pay to suck her tits, they also sold amateur lesbian sex tapes and pictures to underground porn dealers as well as Tony's gay vids and pics. All this turned them quite a tidy profit allowing them to live very well off. And now by adding a cross-dresser to their arsenal they were going to make a mint. She told me that she had emailed a few of the pics of me to one of her dealers and he jumped all over it. He wanted to pay her big money for more "real action" pictures and videos, with the eventual option for magazine spreads and professional video productions. My head was spinning from all this and I told the girls I didn't feel so well. They told me to lay down on the bed and take a nap, that they had some errands to run. I remember falling asleep recounting everything I had learned over the past two days. I must have slept for a few hours because when I woke up it was getting dark out. I got up and walked into the kitchen where Jennifer and April were having dinner. They offered me some but I still felt a little queasy. I sat down next to them and asked Jennifer if I could talk to her seriously for a moment. She nodded yes and taking a deep breath I began to talk. I told her that this was all going very fast for me and it scared me to no end. But it also excited me so much that I was willing to go through with it. But I told her that I didn't want to end up being hit or abused in any way. I don't like pain or S&M, and I was afraid that she would end up being a cruel mistress like you read about in porno books and stories. I said that I loved feeling like a woman, that I felt more like a girl in the past few days than I ever have in my whole life. But I told her I was nervous, very nervous about the whole thing. Jennifer reached over and took my hand and told me that she didn't believe in pain and abuse. She said that never had she hit Tony or allowed him to be hurt. She said she only dealt with people she trusted and who had taken blood tests to prove they were disease free. She said that she would expect me to do my job, but that she would be fair and gentle with me. In fact she said that I would grow to like it. Being adored by these men. Having sex all the time, feeling like a real girl, and that I would be allowed to keep some of the profits I made. She said that even though I really didn't have a choice in this, she was still going to make the whole thing a pleasant experience. I didn't quite know what to say but I thanked her for listening to me. She told me that I should probably eat something since tonight was going to be a BIG night. I asked her what she meant and she said that Tony was coming over tonight and that he and I were going to have sex for her and April's enjoyment. I again grew nervous but excited and my cock began to grow in my panties. April spotted it and reached over and began to stroke me up and down. Jennifer continued by telling me that Tony was going to take my ass cherry and that, if I was lucky, I would be able to suck her tits to consummate our business deal. Then her and April left to get cleaned up for the night and I tried to eat a little of the pizza they left me for dinner. Now that I knew what I had gotten myself into, I was both nervous and excited about the whole thing and I knew from the bulge and wet spot in my panties that I would enjoy this new class I was about to take. About a half and hour later I hear Jennifer calling me and I wandered into the bedroom. There I found April and her both wearing some really sexy lingerie and lighting some candles. April spotted me and walked over to me. She took hold of my hand and led me out of the room and down the hall to the bathroom. She told me to take off my boots and stand over by the toilet. I asked her what she was going to do as I stepped out of my shoes and walked to my assigned spot. She opened a door under the sink and produced an enema bag. My mouth kinda dropped as she began to fill it with warm soapy water. She continued to ignore my questions as she finished filling it and attached the long flexible hose. She then turned to me and asked if I was going to be a good girl for her. I told her that I was and she smiled. She then shut the door and locked it. Before I could ask her why, she began to pull off her top and unhook her bra from her big tits. Once she was naked from the waist up she asked me if I liked them. I told her that they were very sexy. She said she was glad, that she was afraid they were getting too big, now that she was pregnant. I told her that they looked yummy and she giggled. She produced some KY from a drawer and began to lube up the end of the enema hose. She asked me if I had ever had one before and I said no. She told me that I would be getting used to them very quickly as Jennifer believed in clean sexual hygiene for all her prostitutes. She told me to bend over and grab the back of the toilet. As I did she lowered my panties and began to rub the lubed hose against my asshole. Much to my surprise my cock started to grow and April made a point of telling me. "So I see you enjoy anal stimulation. That's good, because after tonight you are going to be getting tons of it." She said as she slowly began to push the hose into my ass. I let out a small grunt as I felt the hose begin to press up against my tight asshole. After a few seconds of twisting and steady pressure it began to slip inside me and I let out a moan of a different type. My cock as rock hard as April began to push more and more of the hose inside me. I felt like I was totally full as the hose worked its way deeper and deeper into my virgin ass. Finally she stopped and told me to clench down on the hose with my asshole. I did and soon I felt a very strange but not unpleasant warmth flow into me. April told me that I had to fight the urge to go as I began to fill up with warm water. After a few minutes I guess the water had all drained into me and the feeling was beginning to become unpleasant. It felt like I really had to go BAD, but April told me to hold it for a few minutes longer. Finally after three more minutes the pressure was unbearable and I begged for her to let me go. She agreed and I made a quick turn and sat myself down. In one jerk she pulled the enema out of me and I let out another moan as what felt like Niagara Falls came out of me. I won't go into anymore of the details but suffice to say after a couple of minutes and some towel drying I was clean both inside and out. As April made sure I looked alright, I slid my panties and shoes back on and we walked back to the bedroom. As I entered I noticed that Tony was now standing there. He was wearing only a very VERY tight pair of black jockey shorts and that's it. He turned to look at me and let out a whistle. He came up to me and asked if it was really me. I told him that it was and he again whistled. He said I made a sexy girl, and that once Jennifer and April were through with me that I'd be even sexier. I asked him what that meant but he suddenly shut up as Jennifer flashed him an evil look. She motioned for Tony and me to sit on the bed. We both crossed over to it and sat next to each other. As I sat there I noticed that there were three video cameras set up in the room. One on each side of the bed and at the foot of the bed. They were all on tripods and set up to tape any action on the bed. I asked Jennifer what those were for and she told me that we were to be videotaped as Tony took my ass cherry. She said that afterward the tapes would be edited into my first anal porn film and mailed to one of the dealers she had mentioned earlier. I started to ask her some more questions but she raised one hand and told me to be quiet. I shut up as she told Tony that he could start. April quickly ran around the room starting each camera before she returned to a small couch where she and Jennifer sat down to watch the action. Tony and I hadn't even started before Jennifer had a hand down April's pants and April was nibbling on her ear. She pointed at the bed and told me to start. I looked at Tony and suddenly he grabbed my head and began to kiss me. I resisted for like two seconds before I said fuck it and started to kiss him back. I really began to get into kissing this stud. I felt his tongue dance inside my mouth and soon we were tongue wrestling as he began to feel me up. His hands went all over me as I started to return the favor. I felt his big broad chest, his tight back and strong arms. He rubbed me all over and soon his hands felt my hardening cock. I too found his erect dick and began to lightly stroke it though his underwear as we continued to kiss. Then Tony wrapped his arms around me and grabbed my ass. He twisted us around so he was lying on the bed and I was on top of him. He continued to kneed my ass as I wiggled around on top of him. I kept kissing him as I began to bump and grind my crotch into his. It was great to feel his big hard cock pressing into mine as we continued to kiss. Gradually I broke off our french kiss and started to lick my way down his body. I lightly kissed and nibbled at his chest, stopping to suck on his nipples. He moved his hands to the top of my head and gently pushed it down to above his bulge. I took my cue and slowly began to lick his cock through his underwear. I lightly nibbled and licked his shaft for a few minutes before I stopped and started to peel his shorts off. Once they were off I had complete access to this cock and balls and strangely it felt so right. I wasn't in the least turned off or sicken by the thought of putting this huge chunk of man meat into my mouth and making him cum inside. In fact just thinking about it made me even hornier. I quickly descended onto his cock, licking and sucking away. Tony let out a moan as I began to slowly suck the head of his cock into my mouth. I bathed his thick shaft with my tongue as I started to gradually take more of it into my mouth. I really started to get into it as I started wiggling my ass around and inhaling this stud's prick. His hands continued to guide my movements as finally I engulfed his dick all the way into my mouth. I was surprised I could deep throat it so well without gagging. My cock was on fire by this point and as I began to move my mouth up and down Tony's cock I started to worm out of my panties. Once I kicked them free I used one of my free hands to slowly stroke my own dick as my tongue stroked Tony's. Up and down I glided totally loving the feel, taste, and experience of my first blowjob. Tony was panting up a storm and calling me his little bitch. He told me to keep sucking him like the slut that I was and I found his words to be really exciting. I liked hearing him call me a slut. I kept blowing him when I noticed a strange new taste on his cock. I quickly figured it was precum and that made me go even crazier. really started to suck him off and I took my other hand and began to roll his heavy balls around. This got him even hotter and I heard him say he was close. Another minute later I felt his balls tighten up and suddenly my mouth was filled with his hot and creamy cum. Again I was amazed that I wasn't completely repulsed as I began to swallow his load. In fact it made me feel like I was going to cum as I sucked his down. Load after load he shot into my eager mouth and I did my best to swallow every drop. It was a new taste for me, something hard to describe but intoxicating none the less. I felt like a hot little slut as I sucked on his erupting fuck pole. Gradually his cum began to stop flowing and his cock began to grow softer. I found myself slurping and sucking his shrinking manhood trying to get every last drop out. When I could produce no more I slowly started kissing my way back up Tony's chest and back to his mouth. We again locked lips as his hands began to feel my ass again. He gently traced my asscrack before rubbing his finger against my asshole. This caused me to shutter and my hard cock began to twitch. I found myself begging for Tony to fuck my ass, to take my cherry. This got him hard again, as I felt his cock start to rub against mine. He started to get up and position himself behind me. I helped him out by getting on all fours, facing the headboard. He gently spread my legs out and got in between them. He reached over and grabbed some KY from a nightstand and started to grease up his cock. I felt mine dripping with anticipation as Tony then sifted his lubing to my asshole. I felt the cool gel being applied to my ass in a gentle circular pattern. Slowly Tony rubbed the gel in, making my backside very slick. Finally he wormed one of his fingers inside and began to spread the KY around inside me. This was making me so hot and again I heard me ask him to fuck me, please fuck me. Tony was more than willing to oblige. I felt him grab my hips as he positioned himself over my asshole. With a small thrust I began to feel the head of his cock press against my puckered ass. I let out a moan as he began to apply pressure to my ass with his cock. My hole wouldn't budge as the pressure increased. Finally as I moaning again Tony gained access and his head slipped inside me. I let out a small scream as I was penetrated for the first time. I yelled for him to continue and he started to press more of his 9 inch cock into me. Slowly, but steadily Tony continued to plow into my ass until I felt his hips press against my ass. I've never felt so full or contented in my whole life. At that instant I knew this is what I wanted to feel all the time. I knew that I would only be truly happy dressed as a woman having a big stud shoving his cock deep into my ass. As I grew accustomed to Tony's invading member he slowly began to withdraw till only his head remained in me. Then with one shift thrust he shoved himself all the way inside me smacking his hips into my ass. I screamed again as he began to really fuck me good. In and out he went. The sound of my moaning and our flesh slapping filled the room. It was the best feeling in my life to have Tony's cock sliding in and out of me, filling me up. I screamed out that I was his slut. That I loved being fucked. This made Tony go even faster. He kept calling me his bitch, and asked me if I liked a real man filling my ass. I yelled that I did. Suddenly Tony pulled himself out and I cried out. What a horrible empty feeling I now felt. My asshole literally screamed out for the lack of something inside it and again I was confronted with an entirely new sensation. The feeling of loss and emptiness. I felt like a part of me was missing, but before I could beg for Tony to continue to fuck me he started to flip me over and soon I was on my back. He slung my stocking covered legs over his shoulders and pressed then down into my chest. I felt him position his cock back over my ass and again in one thrust he was back inside me where he belonged. I let out a moan of fulfillment and that terrible feeling of emptiness was replaced by the glorious feeling of Tony's hot cock. He pressed down on top of me and I got turned on even more by seeing my high heels and legs dangling in front of my face. Tony bent down as he continued to pound my ass and again we started kissing. In and out, in and out he went. I could spend my whole life this way. began to play with myself when Tony yelled out that he was going to cum. In a heartbeat I felt his cock start to twitch and then my insides were bathed in his hot cum. Wave after wave of hot stickiness coated the inside of my ass. This was too much and I too screamed out as my cock erupted all over Tony and me. As he filled my insides I covered our smacking bellies with my cum. Tony was letting out a series of moans causing me to spurt even harder. Finally after what seemed like days I felt Tony began to go soft. With a small pop he withdrew himself from me. He collapsed on top of me and inched his way up my body. We started to kiss again as I wrapped my arms around him. We continued to lay there as I felt his hot cum slowly begin to drip out my ass and onto the bed. It was a fantastic feeling to be filled up with hot cum and feel it slowly drip out of you. This must be how a woman feels after letting her man fuck her. I again felt that empty feeling, although not as bad as before. I knew that I was going to try to have a cock inside me as often as I could as I held Tony tight to my chest. Suddenly I heard a burst of clapping and I held my head up to look at Jennifer and April. April was up turning off the cameras and Jennifer was walking around to the side of the bed. "That was fucking awesome," she said. "I've never seen two guys fucking with that much intensity. That totally blows away any other gay porno, or shemale video I've ever seen. I am SO proud of you Tina. I was afraid you would be so shy on camera and with Tony, that I would be constantly telling you what to do. But damn girl you were such a hoe. I mean slut doesn't even cover how you acted. It was as if you really wanted to be fucked by Tony." I looked up at her and told her that I did. Tony started to get up and looked back down at me. I told her that up until the moment before Tony began kissing me I was very much against it. I was scared and nervous. But once he started to kiss me and feel me up my feelings changed and I very much wanted to feel and act like a girl with her man. I told both Tony and Jennifer that I really REALLY loved being fucked up the ass and giving Tony a blowjob. Jennifer smiled at me as she told Tony to go take a shower. As he left the room she looked at me and sat down next to me on the bed. She took one of my hands and said that if I loved the feeling of cock inside me than I was REALLY going to enjoy working for her. She said that she would keep me filled with cock as often as she could. I smiled and told her that as long as she kept me feeling like a girl, that I was hers forever. She got up and told me that I had just earned some "Extra Credit". I looked up and saw April and her beginning to strip out of their clothes and climb onto the bed with me. Should I Continue? ( I know I want to ) Comments? Email me at [email protected]