I was in my early 20s when I finally decided to tell my girlfriend at the time that I had this fantasy of having sex as woman. I was super nervous about telling her, but surprisingly she was curious. She was super open minded. I ended up sharing the fictional crossdressing erotic stories I had been reading in hopes of having her understand my desires. We didn't talk too much about it afterwards.

One night, we were messing around and she asked me if I wanted to know what cum tasted like? I was caught off guard, but was intrigued. She gave me some great head, and I came into her mouth. She took it all in, and then proceeded to come up to my face. She grabbed my head and pulled me into a deep kiss, dumping my cum into my mouth. It was warm, and had a weird taste to it, but I swallowed is right away. To this day, it was one of the most exhilarating sexual experiences I have had.

After more time talking through desires, she was curious to see how it would feel to have sex with a dick. She threw out the idea that we switch roles for a night - I was super excited. We went shopping for a few things to make this night happen. When we got back, I showered, shaved where I could, and then went to meet her in the room. She did my make up, and I put on a wig she had from halloween. I took out black lingerie that I had bought, and put it on. She wrapped her hair in a bun, and put on the 8 inch dilido we bought. The dilido also had a vibrator that went into her pussy.

We just got right into it. We started making out, she had her hands on my nipples as if they were real breasts. She grabbed my ass as she pulled me closer. I felt like she had all control. I was in heaven. She pulled away and told me to get to my knees. I obeyed. I suddenly found myself with a 8 inch dilido in front of me. She told me to put it in my mouth. I started to lick the shaft of it until I got to the head, and then took it all in my mouth. She kept pushing my head into it so I could take it all in. She then told me to get on my back. She pushed me onto the bed, and was teasing my ass with the tip of her dilido while pouring lube onto it. She slowly entered my tight ass. It was so painful at first, but the more it stayed in, the better it felt. She started slowly thrusting. We were both moaning, and my cock was rock hard. She leaned over, as she kept thrusting, and her body was rubbing my hard cock as she was in me. It felt SO good. She leaned back up, and I was about to cum. She grabbed my cock, and pointed it at my face. Cum shot to my face and chest. She licked my chest, and proceeded to kiss me.

I never had an experience quite like that again, but it was one of the best sexual experiences I've had. It was my CD sexual awakening, although I'm a closeted CD. Now I fantasize about wanting to have a real cock to play with & please. Hopefully I'll meet someone chill enough to play around with.

Let me know if you want me to share some of my fantasies! ;)