1. Memoirs of a Crossdresser: Chapter 1


    Date: 6/21/2016, Categories: Crossdressing, Author: vanessagrrl, Rating: 8, Source: LushStories

    to conceal myself, but once I got in the car, I took the coat off. It felt so good to feel so feminine and sexy. I drove to the city and parked. When I got out I headed towards a porn shop that I often bought videos at. I remember getting a cat call on my way, which turned me on. What turned me on more was the sound of my heels on the linoleum once I got inside the shop. I could see men in the shop looking at me, and I think some of them wanted to fuck me, which turned me on even more. I bought a new butt plug and video and went home to give myself some release, after getting a few guys off over the phone. I liked to see how far I could take things sometimes. I had one guy tell me that he wanted me to call him from a payphone, so I would have to go out dressed to call him. That turned me on but it didn't go much further. Another guy had me drive to a local parking lot and fuck myself with my dildo in the back of my car. This kind of thing went on for some more time, and then once again, I needed to go to another level. A few of the guys I was talking to sometimes asked about meeting me. I was really shy about it, and scared, but I was intrigued by it. One night, I finally worked up the courage to meet a guy who I had been talking to. He was young, and I don't think had much experience with girls like me, but he was curious. I was already dolled up as we had been talking online, and on the phone. We agreed to meet at a parking lot near where we lived and just see how it went. ...
    I pulled up in my Jeep and waited for a couple of minutes until I saw his car arrive and park. I got out and walked over to his car, and got in. We talked for a couple of minutes, but I could tell we were both so shy about this. He put his hand on my leg for a second and said, "I like your stockings," but that was it. I hoped he would kiss me, but he didn't. We both were getting nervous about being in a parking lot late at night, so we decided to leave, and see about meeting up again sometime. I remember how cute he was. He was young, athletic, and very attractive, but I needed someone a little bit more aggressive, at least who would initiate things. I went home and played with my dildo that night, fantasizing about him being inside of me. We kept in touch, and always talked about meeting up again, but it never happened. I think we were both too shy to make it so. A few months later, another guy I had talked to a lot finally sprung the question and asked about getting together. I was feeling comfortable with him since we had talked on the phone a bunch, and got to know each other. We decided to go a step further than my last experience, and we would meet at a motel parking lot. If we met, and decided to go further, he would get us a room, and we'd go from there. We met in the lot, and decided to go for it. I had some booze on me, and I made myself a drink, and he had some too. He asked me if I had ever seen a man's cock before. I told him just my own, so he pulled his pants ...
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