Flipped by a Pro

My name is Michelle. Michelle is not the name I was given at birth, even though at birth I wish I would have been named Michelle, not Michael. I have been called Michael and I am still called Miichael by everyone, except by Jack. For all intents and purpose I am a normal healthy male, on the outside, but on the inside something else burns. Inside of me burns a horney little faggot that needs to suck cock and be fucked silly like a teenage girl in heat. When i look in the mirror all I see is a horney little cunt that wants to get fucked like a dog. When I am naked I see my cock. It's very big, fat and velvety. My nipple are very small. i pull on them to try and make them bigger. They are extremely sensitive. When they are touched I drop to my knees, that is how sensitive they are. For my whole life, right up to the age of 39, no man every touched my nipples, only women. No man ever put his fingers on my tight little puckerhole either. No women ever did intentionally either; maybe a brush here and there but never intentionally. When i was about 25 my girlfriend at the time started leaving clothes at my aprtment. She left bras and panties and nylons. Yes, you know what happened. I started wearing them around the house when she was not there, but I wasn't addicted to the wearing. It wasn't until I was about 39 and she left me that I went into a deep depression, and was alone for the first time in my life. Really alone. Alone with my thoughts. With my own mind all twisted up and freaking out. I wanted nothing to do with women because they always hurt me or wanted something from me I could never totally give them. 100% of me. What always held me back? No question that deep deep inside of me was a desire for cock, but my concious mind never let that one come out that's for sure. so I was alone. Alone ina very big aparment with a very fertile brain. No one to bother me, come over or call me anytime she wanted. No one to interupt me or my fertile mind. And, then came the internet. Porno was so readily available that it was like driving down the street and seeing all of the places to shop. I turned it on and it started turning me on. I'm not sure how it happened but of course I looked at a gay sight. I started looking at mens cocks and I started jerking off hard. Every day i turned on the Net and looked at cock. Then that led to sissy sites, and transvesties and then toy sites. I bought toys. I bought a wig, nylons, dildos. Lots of dildos. I taught myself how to take one in my girlypussy. I really fucked myself hard and I fucked myself a lot. I started fantasizing about sucking a real cock, and wondering what a real cock in my cunt would feel like. And, then, one night while I was in a chat room jack popped onto my screen. "Hi" he said. oh sit I tought, how did he come up on my screen? But I said "hi" back. and then the flipper went into action. He asked me what I was on the site for. "what are you lookingfor" he said. I told him not much, just looking around. He said, "oh so your new to this site?" I said "yes". New to this whole thing and put up "lol". He told me his name was jack. That he was 57 and was gay. he said he was looking for a long term relationship and came on this site just to see what was going on and if there wasa a chnace to meet someone. he told me he was just coming out of a long term relaionship and he got hurt bad. I was amazed, we seemed to have a lot in common. He was cool and he was patient. Jack asked me about myself. He asked me for my email address and said we should chat awhile, get to know each other. I said "okay". I gave him my email address. My adrenaline was flowing fast and hard. I could not believe what I just did. What the hell was I thinking? But I did it, and that's it. I did it. I gave him my email address and then I went and fucked myslef harder and came vene harder than I have ever cum before. When I was done really giving myself a good fucking I then sucked on that hot sticky didlo and jerked myself off and came again. I feel asleep in my corset and nylons. That was afirst. two hours later I woke up thinking about Jack and beat my hard cock off again. I came on my stomach and for the first time I stuck my own cum in my mouth. For days I was just a mess. i was thinking about Jack and thinking about cock and just thinking about everything all at once. I gave him my email address but I didn't get his. I went back to the same site every dau, sometimes ten times a night hoping he would see my name and chime in and say hi. Weeks went by and nothing. Nothing! One night I came home and I found the email I had been wanted, hoping for, going crazy about. It was jack and he had included a picture. he told me he was happy he met me online but that he wanted to meet me in person. He gave me his phone number and asked if I would like to talk on the phone. No, I did not want to talk on the phone and I did not want to meet him. Was he crazy/ Was i crazy? i couldn't meet a man, a gay man for any reason no matter what I needed or ached for physically: or was it emotionally? I was confused, elated, happy, scared out of my wits. Oh god and I was freaking hornier than a 50 men at a bath house. So i wrote back and told him he was very handsome and that his lover lost out and that he would have no problems finding a new man when he was ready. i then told him thank you but I would not be calling and that I was straight but appreciated the interest. I was fucking lying though my teeth. I found him extremely handsome, did not want him finding another man and I wanted him to fuck me right then and there. However, that might have been what I really wanted I had no idea how to say it or even how to approach it. So I called him. We talked for about an hour. We talked about relationships and life and love and happiness, but we did not talk about sex or my ned to suck his cock. he never brought it up. Jack could tell I was a scared little boy who didn't know what the fuck he wanted. Jack was patient. Very pateint. Needless to say Jack was now in my head. He was actually deep inside my head and he was all I could concentrate on. Nothing else mattered. Friends, drinking, girls or even pron on the Net. I was dressing all the time. I was wearing nylons all the time. I was even wearing a thong to work. I was excited and I was cumming all the time. I was thinking about cock like a man in the desert thinks about water. I wanted a drink. We started talking on the phone a couple times a week. I was playing it cool and so was Jack. Jack knew he had me, he knew it but I didn't. I still believed I could just stop anytime I wanted. I was so wrong. Jack invited me to his house to talk and hang out, drink some wine. I told him I would think about it. It's all I did was think about it, and fantasize, and dream and cum on my stomach. I made plans to come by on a Friday night. After nine I said. I showed up witha bottle of wine. Scared like a little boy or an actor going onto the stage for the first time, or peeing in front of 50 people at a concert. But I went. I wore a thong under my jeans. Nylons too. But I had my socks on so no one could see them. Idid not plan on doing anything but I still wore my gilrly clothes, just in case? I showed up and there he was. older than I, but still handsome and verile. He invited me in. poured us a drink and we sat onthe couch. Jack sat right next to me, like it was a date. I was very nervous, so nervous that he sensed it and went and sat on a chir across form me. He could see me. I mean really see me. He knew what was going on. He sensed my nerves and he played it so very very chill. I looked at his critch he had a semi hard on in his jeans. I wanted him to tell me to get on my kneesa dnto come over and suck his cock. That's what I wanted to do, but I was to chicken to just do it. So we talked and talked and then I told him I had to go. The moment had passed and I didn't sieze on it. He knew not to be too agressive. He knew, I would be back. I got outof his house and went to my car. I let out a huge sigh of relief? Then I jerked myself off. It was a long ride and I stopped the car and did it again. Then when I got home I pulled out my dildo. I stuck it to the wall and put a pair of jeans around it, lettingnit stick out of the zipper. I put a pair of shoes on the floor ender the pant legs and I sucked that dildo like it was going to be my last time. I swallowed the eight inch piece of latex like it was nothing. I came so so so so hard all over my nyloned leg. I needed a real cock. i turned on my email and there was an email from Jack. He said he was happy to have met me and that he hoped I would come by again. I replied that I would like to do so. Soon. One week later I did. I went there with the full dress up. Nylons, panites and bra. I never told jack about my cross-dressing. never. I figured if something was going to happen I would have to be dressed like a woman. Maybe that was a protection for me. Dressed like a woman was not being a full man and thus it made me not gay. Weird but complex and a protection built in by 40 years of masculinity and fear . I went to his house. Poured a glass of wine. He called to me to come up stairs. He was on the couch. I did not want to be on the couch I wanted in his bed and when I saw him I told him so. He smiled and nodded and walked by me and went into his room. Candles were lit. He knew I was ready so he was ready for me. jack got undressed and laid down in his bed. I watched him, nervous but excited. He had a strong erection. I looked at it. I wasn't scared anymore. I had made up my mind, resolved it to what I wanted, needed, had to have. I looked at him and said I hope you don't get mad at me. i said since 'I'm going to go all the way I might as well do ALL the way". I stripped down to my panites, nylons and bra. jack looked me over, smiled and nodded his approval. It was done. I had completed my journey and been accepted for my cross-dressing litle fag boy looks. I jumped into his arms. He kissed me with so much passion and I returned his kisses with wanton pleasure. I sucked on his toungue and he french kissed me with abandon. he found me handsome, pretty and hard. My cock/clitty was bigger than it had ever been. he touched it, grabbed it, stroked it, but only for a few seconds. Jack wanted my mouth on his. My lover, my mentor, my stud wanted to be kissed, and I did not let him down. I so wanted to suck on his cock. He let me slide down and put his velvet stick into my mouth. My very first time and I still remember it, the taste, the musky clean soapy scent. The hairs playing on my nose as i swallowed it down my throat. Jack took a finger and rubbed my little cunt. I jumped with excitemnet. jack told me, i know whay your really here. i know what you need little girl. You need to be fucked and that what i intend to do. "I am your first and I will always be your first." "You will always remember me and you will remember this moment. He relished taking his virgin boy/girl. I saw it in him. he had patiently waited to devirginize me. he knew what he was doign and he knew what he wanted. he wanted to flip me. he wanted me to be a gay little boy unafraid to suck cock and be his little bitch. I was ready for that moment. It was all I dreamed about and wanted. I got on my hands and knees and stuck my white panties ass in the air for him. He got on my back. he wrapped his forearm around my neck, making it hard to breathe. All of his weight was on me. He took his manhood and rubbed it on my lubricated asshole. He put his tip into my my open bud. Slowly, but without fear. He knew i was ready. He knew I ahd taken large dildo in my ass. He knew everything about me and everything I needed. I slid hisprick into my body. Into my cunt. It went all the way in. I could feel his balls slapping up against mine. I was in ecstacy. Pure unadulterated acstacy. he got up off my back. Placed his hands on my hips and proceeded to fuck me. Fuck me with a real cock, not some plastic lifeless pice of latex. his hands were strong, his grunts weer loud and real. His sweat was on me. I could not believe this was happening to me. I didn't move at first. i jsut stayed there and felt the movement inside me. the incredible feeling of a mushroom headed cock sling in and out of me. Slowly at first, the a bit quicker, then faster. the he stopped and let it stay there. i squeezed on it and felt his hardness more fully. Realized I knew it was in me and just let go of myself. I started pushing back against him. He stayed there and let me slide on his cock. let me control the movement for a minute. Then, he took over and started to give it to me so hard the bed shook. My head was going back and forth. Noises of an animal in heat emanated from my throat. This was really happening. I was being fucked like a girl. I was dressed like one, felt like was. I was a woman now. I was a woman finally. Suddenly I felt something very hot, almost burning going on in my cunt. I did not know what it was. I had never felt that sensation before, but it felt really good. hot, but good. Jack had cummed inside my cunt and when he did, I felt something I never felt beofre. his cock was sliding in and out with such ease. It was so lubricated and hot. I felt something happen inside me. A small trmoer in my body, then a building sensation that I never felt before. I was cumming. Cum was gushing out of my clitty. Jack grabbed my cock and jerked it. My god I never felt anything like it. no orgasm had ever been like this. Nothing had ever been like this. I screamed. I screamed loud from the orgasm. jack took a hnadlful of my cum and stuck it in my mouth. I sucked on his fingers like a baby on a nipple. I ate my own cum and I enjoyed it so very very much. Jack pulle dout of me and his cum slipped out of my once tight pussy. His cum leaked down my nyloned leg. It smelled so good. thenJack took his cock and put it in my mouth. he said I made him so hot. that i was so pretty and smooth adnsexy. he took his cock, shoved it in my mouth and told me to suck him off. i would have sucked of a gorrlla at atht moment. I was comepletely under his command. I would have done anything for him. I sucked on his still swollen member, willingly, lovingly and desperately. It didn't tkae long and he came in my mouth. I felt it explode. It was a weird sensation, but it tasted good. I let his cum swirl around on my mouth and let some drip onto my chin. I wanted it there to lick it up later. I swallowed his cum willingly, fearlessly, desperately. I would have eaten shit if he told me too. I was not myslef. I was someone from deep inside of myself. I had no shame or fear. All I was was a bundle of girl. It all came out in that one span of time. All of it happened in that bedroom in that one monet. it has happened again many times and it will happen again tonight. i need to go put on my wig and make-up. jack is taking me out to meet a few of his friends. He wants them to meet Michelle his little nyphomaniac cuntslave.