My True Story

Chapter 1:

 I was a kid when I first discovered women's underwear. I loved the way it made me feel. I had a friend who I'd play the normal games that kids play with, and I would always be the girl character. We were children, so nothing out of line went on, but even at a very young age, I had felt an attraction to femininity. There was something that made me feel like I should be the damsel in distress, waiting to be rescued. I remember wanting to feel girly.

As I got older, my interests in anything female seemed to slow down. I don't think I touched a bra or pair of panties for many years, until middle school and puberty arrived. I often waited for my mother to be away so I could rummage through her panty drawers to find things to wear. Some days I would cut school so I could stay home while she was at work. I found all sorts of fun items, and loved playing dress up. I tried all of them on, enjoying the pleasure of the silk and lace. This went on for several years. I loved dressing up, and looking at myself in the mirror. Eventually, I would go into some of her make-up and perfume too.

All this time I still was attracted to girls, though. I did end up dating a few, and after high school, when I was about 18, I had a long relationship with a girl who would introduce me to a new love: sex toys. We played around with vibrators and dildos a lot, and we experimented with putting them in both her holes. But what pushed me further into becoming Vanessa was when we broke up. She left all of the toys and some of her lingerie at my house, so now they were mine. It was a new level, owning my own lingerie, being able to dress up in my room whenever I wanted to, and being able to fuck myself with a big dildo.

Eventually, I began buying things for myself. I found that I really enjoyed the feeling of a medium sized buttplug. My choice of lingerie was always garters, thongs, silk stockings, and a bra. I really loved the feeling of the garters and stockings on my legs while the thong crept up between my ass. There were times when I would go to Victoria's Secret after work, buy a new thong, bra, garter, and stockings, and then change into them in the bathroom. Then I could feel them under my clothes as I drove home.

I would often play online in chat rooms, watching porn, and masturbating. I would make friends in the chat rooms, and I got so turned on talking to men who were interested in being with me. I played around with some men over the phone, and I got so turned on making men cum for me, hearing them moan as they blew their load.

 It got to a point where just dressing up wasn't enough. I began wearing makeup, and I got pretty good at applying it. Finally I decided that I needed to get out of the house. I remember the first time that I went out dressed. I was wearing a black thong, bra, and garter belt from Victoria's Secret, with lacy stockings, 4" high heeled ankle boots, a plaid skirt, and a black top. I wore a long coat when I walked to my car 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 down, revealing his semi-hard dick. I was a little shocked, but decided that I had gone this far so it was time to go further. I started rubbing his cock, which he enjoyed a lot before suggesting we move to the bed.

We laid down next to each other, as I continued to stroke his hard cock. I was surprised how much I enjoyed the feeling. I liked feeling a man's hard dick in my hand, hearing him moan for me while I gave him pleasure. He reached up my skirt and began to rub my dick too. I was loving this feeling, but I decided I wanted to go a step further. With my other hand, I began to reach for a condom in my purse, so I could blow him. Just as I reached over, I felt his cock explode in my hand. It was a sexy feeling, but I was a little disappointed that I didn't get to taste my first dick.

He apologized and went down to my dick and started to suck it. I stopped him, as I realized that this wasn't for me. Girls don't get their dicks sucked. He asked me what I would normally do to myself, so I took out the dildo that I brought with me. His eyes lit up, and he asked me to show him. I started to fuck myself with my big 8" dildo, and I almost thought he was going to get hard again. He grabbed the dildo and started to fuck me with it. I was excited, but I decide that this wasn't the way I wanted to go. Besides, I knew that if I came, I might start to feel the guilt that I often felt after dressing, so I stopped him. We talked a bit, said goodnight, and I went home.

I know he was engaged at the time, and I think he was looking to get something out of his system. I was still left feeling a little confused and unsatisfied, but I went on for a while just playing on the phone, and taking little trips en femme. Sometimes I'd go and buy some magazines at a 7-11. Other times, I'd have phone sex partners lead me around over the phone while I drove or walked to wherever they would tell me. I enjoyed it all, and I would look forward to new ways to experiment, and new experiences to come.