
How I was a woman.
I won't hide it, I really liked trying on my mother's clothes as a child. Stockings and lace panties especially excited me. I even wore them to school sometimes. What stirred up my feminine side again was an event that happened after we moved to a different neighborhood. Because I refused to take part in a group fight, they took me to the nearest tree belt and, in front of some girls, forced me to suck off one of the guys. And not just suck him off, but swallow his cum. This punishment happened several times, until we moved to another town. I won't name it—it's a small town, and I still live there. Soon it was all forgotten like a bad dream. I served
in the army. Then I got a job at a branch of a St. Petersburg company, where after a couple of years I became the deputy branch director. It was 1998. I was sent on a business trip to the head office. Since the plane arrived late at night, the boss himself met me at the airport. He offered me to stay at his place for the night, as his wife was away and there was room. Not sensing a trap, I went. We sat, drank, talked. Whether it was from the drinks or because he slipped me something, I completely lost all sense of boundaries.And then, at some point, he sat down next to me, ran his hand over my leg and asked—are you as passionate as I am? I answered—probably. I already understood where this interaction was most likely headed. Then Roman (that was the boss's name) suggested we wash up and, preferably, do an enema. In short, I understood that sex was unavoidable. Of course, I washed up, did the enema, and got into bed. First, he made me suck him, then put me on all fours, lubricated the hole with cream, and entered me. I must say, considering his size, he did it relatively carefully. It was my first anal sex, so it hurt. In the end, we tried all positions—doggy style, me on top, missionary. My gymnastics training didn't go to waste. That night, he took me three times. In the morning, it hurt to walk, and I felt a constant urge to go to the bathroom for a bowel movement. Plus a terrible hangover. Anyway, Roman told me to rest at home. And he also gave me money, told me to go buy something from women's lingerie. He went to work himself. By lunchtime, I had recovered a bit. I went to change the leftover 100 dollars, went to a store. I thought I'd die of shame. I explained to the saleswoman that I was picking out lingerie for my wife. I bought panties, black stockings, a garter belt, and a bra.
The evening started with the same program—wine, a video, small talk. Then the boss asked me to put on what I had bought. I put on the panties, garter belt, stockings, and bra. Roman said I had good taste, then made me suck him off and came in my mouth. Then we went to sleep, and I didn't take the clothes off. During the night, he took me again. My ass hurt, I moaned, but he thought it was from pleasure. In the morning, Roma said he really liked me, especially in a feminine guise. And immediately offered to do my makeup and dress me as a woman. We went to his makeup artist friend. I felt like dying, seeing how she looked at me. But they did everything—makeup, lipstick, hairstyling (I had medium-length hair back then). Then another shopping trip. We bought a dress, shoes with a small heel—I didn't know how to walk in heels then. By evening, I looked like a real girl. We even went to a cafe together. It seemed to me that everyone was looking at me sideways. And I was afraid they'd notice the erection that was tormenting me. In the evening, everything repeated, but now with stripping and dancing.
In short, it all came down to me transferring to St. Petersburg a couple of weeks later to work as Roman's secretary. He rented an apartment for me. The only condition was that I had to come to work in a feminine guise. He called me Vlada. For the first month, I felt like the whole office knew about me, that I wasn't a girl. But then everything settled down. I learned to use the toilet sitting down, started learning to wear high heels. At corporate parties, men asked me to dance, invited me to cafes. In general, I started living a woman's lifestyle. Only the small breasts were embarrassing, but a padded bra saved the day. Though, I had to decline going to the bathhouse with girlfriends. Everything seemed to suit me, especially the boss's material gratitude.
The boiling point (and the end of my relationship with Roma) was an incident when his business partners from Samara came. When everyone was sitting at the table—it was a party, not a corporate event—one of the guests told Roma he had a cute secretary, to which he replied that she also gives good head. I heard all of this. And by the end of the evening, he suggested I escort the guest, I think his name was Misha, to the apartment where he was staying. I thought he wanted to please the guest and agreed. In the end, we ended up at Misha's place, where he, right in the hallway, unzipped his pants, put me on my knees, and made me suck his unwashed member. When he finished, he took out 50 bucks and showed me the door. I felt like a real whore.
Later, there were problems with readjustment. I had surgery to remove the implants. It took a long time to get back into the male role. I even mixed up bathrooms periodically, called myself by the female name. I took up sports, got a job. Gradually, everything got better. Now I'm married, have a child. My wife—a close person—knows about my past but never reproaches me. And only two small scars from the implants remind me of the past. Though, sometimes she makes me put on her lingerie during sex, but that's just a game. Now no one would ever guess I was once a woman. But sometimes I really want to...