Crossdressing leads to first homosexual experience - Sex Stories

Crossdressing leads to first homosexual experience

I've been wearing panties for over ten years, ever since my former Mistress made me switch from my mens' boxers to womens' panties. She gave up the BDSM lifestyle years ago when she met a man who was not into it. She was going to f***e me to have sex with a man but we never got that far. I have not had a real time Mistress since but I continued to wear the panties. A few months ago, I bought a couple of night gowns and sl**p in them occasionally. I've been wanting to buy a dress for awhile now. I was too afraid to buy it at my local Walmart since I often see people I know shopping there. I finally worked up the nerve to drive to a town about 20-25 minutes away to buy a dress at Walmart. I figured it was a small town and the Walmart would be easy to find so I didn’t look up the directions before I left. I was wrong. I spent about 30 minutes driving around town. I found a K-Mart and decided to try that. I chickened out when I saw there was no self checkout. I always use the self checkout to buy my panties since I have a hard time working up the nerve just to browse the womens department. Dealing with a live person at the checkout would be too difficult for me. I finally found the Walmart. All the extra driving around town was not a total loss since I saw a lot of really hot women walking around the downtown area. I head into the store and start browsing the womens department. I find two dresses I like and pickup a pack of panties and go to through the self checkout. As soon as ...

... I get home, I setup my camera and take several photos modeling my new dresses and post them on xhamster.com. A few days later, it's Friday night and I was thinking about all the hot women I saw while driving around the neighboring town. I thought about how exciting it would be to put on a dress and drive around town. I know I could never to that in my own town. I live in a small town with a large university. The risk of seeing someone I know is just too great. The reason I like to crossdress is the humiliation factor. Being laughed at by a bunch of college girls would be great, but much too risky in my own hometown. About 11 pm Friday night, I leave the house wearing pink panties, a tee shirt and a pair of gym shorts. I know of a spot about a half mile from my house where I can pull off the road. I can still see the main road but I figure in the dark I won't be seen. I quickly change into my dress and drive to the neighboring town. Since most towns in the area have cruising laws that limit you to 3 trips up and down the main drag, I choose a route that takes me down the main street and around some of residential streets to make my time last longer. I make two trips around town and see a few girls out (most of them are with guys). I think a few see me but I don't know for sure. I'm too scared to make eye contact but I roll the windows down so I can hear if anybody comments about the old man in a dress. I hear nothing. I decide to drive to the Walmart. I plan to get out of my ...