Crossdressing leads to first homosexual experience - Sex Stories

Crossdressing leads to first homosexual experience

... headed home. Since I came into my neighborhood from a different direction, I didn't pass my changing spot. I could have driven past my house and to my changing spot but since I knew all my neighbors would be in bed and all the light were out, I just went home in my dress. Still in my dress, I masturbated and came in about 10 seconds. I was so excited the next day, I wanted to do the downtown drive again so I waited until 1 AM and drove back into town wearing my second dress. Unfortunately, it hat started raining and very few people where on the street. Sunday morning I knew I couldn't wait until next weekend do crossdress in public again. I decided to only do this in my hometown on Friday and Saturday nights since the locals usually stay away those nights because of all the wild students. I thought about the small neighboring town but knew I would have to step things up to top Friday night so I decided to try it in the daylight. I headed back to the neighboring town with only my panties under my jeans and tee shirt. Back to Walmart for another new dress. I picked out another dress and more panties. I was headed to the self-checkout but saw there was no one in the express line. The cashier was a woman about my age (I’m 51) and average looking. Nothing special but I would submit to her if she dominated me. My face was red and my hand were shaking but she was very nice. I decided to make eye contact but she wouldn't look up. I'm sure she knew I was a pervert. After leaving ...

... Walmart, I needed a safe place to change. I remembered an old abandoned road off the highway a few miles out of town. It was part of the original road before they put in the 4-lane highway. It come off the highway, curves and rejoins the highway a half mile further down. No one used it but it's not blocked off so I figured it would be a safe place to change. I change into my new dress and start taking pictures of myself using the camera timer. I was so focused on staying still until the timer goes off, I never heard the car coming around the curve. I scramble to grab my camera and get back into my car but it's too late. The car stops in front of me. I see a gray haired old man in the car. I have no choice but to cross in front of him to get back into my car. I get in the car and drive off. I head back into town and drive the same circuit as Friday night but this time in the broad daylight. I avoid eye contact with the guys but try to make eye contact with the girls. One girl in the passenger seat of an SUV does a double take as we sit at a red light and later on a side street a very attractive young woman waiting by the door of her car gives me a little smirk when she get the full view of me as I pass. I would have preferred her to break out in hysterical laughter when she saw my dress but I'll take the smirk. As I head out of town, I stop in the K-Mart parking lot (Walmart is on the other side of town) to take another picture. I get out of the car and take the picture with the ...