A Transvestite Odyssey

I like playing a girl, but it's complicated. I have always been more attracted to women than men, and had many relationships with women including two marriages. As a young man I had several sexual experiences where I played a feminine role. Wearing girly things was a real turn-on for me, and it seemed to make it less queer for us both. I would later learn that most tranny chasers identify as bi or heterosexual, while many 'girls' identify as straight.

For many years the girl inside me lay dormant. After professional school and a divorce, I moved on to a job in a different town and bought a house. Up until that time I had roommates or a wife and never had a great deal of privacy. It was at this time that my new found freedom allowed me to experiment with my fetish. It started by seeing a dress in the window of a second hand store and snowballed into buying lingerie and shoes from catalogues. Internet shopping had not happened yet, but there was a primitive internet with many 'alt dot' discussion groups where I learned that was not alone and that I could accept myself even if society did not. Many transgendered women say they were born in the wrong body. I thought I was born on the wrong planet, and that my body was just fine.

About this time I met an attractive woman and we started a relationship that was going well. We would spend the nights together, and I gave her a key to my place. I had my feminine clothes hidden in the attic, but one afternoon I was working from home wearing women's office attire and she walked in unannounced. Well she freaks - I freak - we tried to resolve it. I even dressed up for her, but she told me it made her sick to see me that way. She went on to express her disappointment, because until then she thought I was the perfect man.

Then she told me something I would internalize. "Getting fucked is the most feminine thing a woman can do and don't you want that?"

I answered honestly that I didn't want it because I was not attracted to mens masculinity. Nevertheless the relationship degenerated into her making me feel guilty and finally threatening to out me to my friends, family, and colleagues. This lasted for almost a year and I was miserable. Finally, she left town for an extended work gig and I immediately started dating other women and crossdressing more. When she came back, I broke up with her, and she did out me. I just denied it because everyone knew she had a temper and was vindictive. One of the women I dated while she was away ended up as my second wife. My ex girlfriend outed me to her and initially she was accepting since she had indulged in some kinky things with a previous boyfriend. After we were married, she even told me I could wear her clothes, some of which fit my slim frame. She had a nine-to-five job, and I worked a lot from home, where I dressed-up without fear. The indulgence was a slippery slope, and I soon wanted out of the closet.

Through the early internet, I made contact with some crossdressers using a news group. I also met a man online that wanted to meet with me. I agreed not knowing what would happen. I was just excited to be dressed up with someone accepting me or that 'admired' me. Also, I was seduced by the idea of a man being attracted to me - it seemed to affirm my feelings of femininity. By this time my crossdressing had become fairly sophisticated, and I agreed to meet this guy at my hotel room. In preparation, I shaved all over, spent a long time on makeup, and wore a cute navy dress that gave my boyish hips some breadth. He arrived with a bottle of cheap wine and he was not terribly attractive, but I was experiencing a tremendous adrenalin rush and his demeanor didn't matter. He seemed pleased with the way I looked, so I made the first move. We made out for a while, until I reached down to touch his leg and found a nice erection.

I looked at him seductively, and spoke in my best Lauren Bacall voice. "Would like me to suck your dick?"

I helped him unzip his pants, and then looked in the mirror to see a dick sliding into my mouth. I was delirious with a new found lust, and soon wanted to go further by getting fucked. He was sitting in a chair and I was on my knees if front of him when I suggested we get on the bed.

He took off his pants, lay on his back and told me. "You to do all the work."

I left my dress on, removed my panties, and joined him on the bed. He was excited and his penis was very warm and hard, and I rolled a condom on him. Then I lubed my hole with moisturizer, mounted him, and started to rub his dick against my willing anus. After a while of clumsy fumbling around, I managed to get his dick head inside me, but it really hurt. Then he just rammed it in and it hurt even more. As he started to fuck me, I rode him like a bronco to soften his deeper thrusts. I didn't enjoy the fucking as much as the affirmation from being the object of pure male desire. The next day my ass was sore, and I had to conceal a smile while in work meetings. I ended up seeing this guy a couple more times and the sex did get more enjoyable, but he did not.

This man told me about a gay bar in this city that was frequented by trannies, and my little tryst had given me enough confidence to go out in public. One Saturday night while away on business, I got dolled up wearing a shin length flowing a-line skirt, strappy sandals, and a midriff-bearing low-cut sweater. I looked good and felt good as I strutted my stuff into this place that would become my regular hang out. The night was a great success, as I made a number of friends, and was even picked up and taken to bed. There was no turning back now. Over the next few years I would come out completely, while spending more time on business in that city. I spent so much time there that I rented an apartment, which allowed my alternate lifestyle to flourish. I had two closets one for each of my genders. I slept with a lot of guys and am lucky not to have caught any viruses. Many of my gurl friends at this time were in the various stages of transitioning to become trans-women. My closest friends were more in your face - we owned the word transvestite - which most transsexuals see as pejorative. We wanted to act fem but to pee standing up. We had attitude and went to many straight nightclubs, and no one messed with us.

I gave my wife a G-rated version of my activities while away, which she tolerated as long as I was careful not to be seen by any of my colleagues. She, being a very feminine herself, gave me cover should anyone suspect me for my metrosexual look. She saw my personality improve as I was a nicer person in drag. I liked playing girl, because I could express myself through fashion. I was much more outgoing in drag, and even did karaoke by singing country songs - most with trans-meaningful lyrics. I was a real transvestite with emphasis on the vest, because I loved the clothes and the way I felt wearing them in public. I became obsessed with women's style and spent a lot of time shopping and working on my looks. I even got laser to remove some body hair and pierced my ears so I could wear nice earrings. I took care of my skin and nails, and learned why it takes so long for a woman to get ready. The only problem was going back to work Monday having to play what felt increasingly like a the role of a man. Our separate lives made the marriage unsustainable, so we decided to get new jobs in the same city - one known for its nightlife. After we moved, I continued going out on weekend nights until my wife became jealous. She saw my feminine side as competition for her husband, which was true.

My wife still traveled a lot, and often visited her family for extended periods of time. This gave me license to become a complete slut - sometimes having more than one man in a single day. The internet was in full bloom at this point, and Craigslist was the place to hook up. I became a tranny nymphomaniac because when they fucked me, I just wanted more. I would have had even more sex, but half the men on Craigslist want you to fuck them. I told them if they want to get fucked to do the work: pluck your brows, shave your legs, and wear uncomfortable clothes. During this period, I discovered a fetish club that rented-out a bar I frequented. I remember going to a private party where I was getting eaten out by my date, while I sucked another guy as people watched. Then I was whipped by a guy whom I told my safe word was 'ouch'. I sat on a stage next to a beautiful naked woman throating a guy with a nice dick. When she lay down, he pierced her nipple with a 4" needle, and she had an incredible shaking orgasm. I had an extended relationship with a M-F couple, and even engaged in prostitution just for the fun of it. I had a guy pay me to abuse him and to pee in his mouth. I really wanted rough multi-way sex, and tried unsuccessfully to arrange a gang bang for myself.

Eventually, our children were old enough to figure out what was going on and I had to curtail my activities for their sake. I could only fool around on the down-low while traveling. It was difficult to keep an extensive wardrobe, so I tried sex with men as a man, but didn't find it satisfying, and I had zero interest in fucking a guy. To enjoy receptive sex I had to feel like a woman, and I felt most like a woman while receiving a man's sex. I view those early years as my alter ego's teen and young adult years. Now I act like a middle age woman even though I'm older than that now. I kept telling myself I was going to quit when I'm 40, which became 50, which is now 60, but 'the force' is strong in me. I don't need the adrenalin and affirmation I would get when I was younger - just a good fuckin' from time to time to remind me of who I really am. Now I live for that sex, that sweet submission I feel when my man uses me for our pleasure.