So I thought I would post the story of my first time fooling around with another CD since it just happened last night. I enjoy reading so much about other people's experiences, so why shouldn't I share mine? Several months ago, I started messaging back and forth with someone on Fetlife. I'm 30, and this person is a few years younger than me. I've only been in relationships with women in the past, and only a couple have known my crossdressing (as well as experiment with it). He has only been in gay relationships, but told me about how he is curious about being with a woman. For several months we would just chat on Steam about random stuff...sometimes send each other a naughty pic, and then one day we both agreed that we would finally get together and would dress up for another CD for the first time together. We agreed that fooling around was on the table and I made a reservation at a hotel near us. I showed up around 7 pm just to relax and get comfortable with the environment. I decided that it wouldn't be a great idea to dress up before he arrived because since he would show up in boy mode it might make him feel awkward. He showed up around 8 and I invited him in. After a very nervous introduction from both of us we just sat down and watched TV. He brought a little whiskey, so we each had a couple drinks to loosen up...we definitely were not drunk, maybe slightly buzzed. Anyway, I thought maybe to ease the tension I would show him some of the various lingerie and dresses I brought, and he did the same, and then I offered to go change first if it would make him feel better, but he said he would dress up in the room while I changed in the bathroom. I took a red sweater dress, a black bra and panties, hose, my long black wig, and heels to the bathroom and got changed. I don't have makeup, but I thought I looked pretty good in the dress as far as my shape is concerned. After a couple minutes he said he was ready and he was wearing a cute short layered skirt with thigh highs and a garter belt with black panties. He was also wearing a black bra and this purple short top that exposed his midriff. I'm tall and skinny, but he's even skinnier, so he had a slight effeminate body. We both sat down on the bed together while the TV was on and chatted and slowly got closer together. I put my arm on his leg and he stared rubbing my back. Eventually we both embraced and started kissing. I had never kissed a guy before, but it seemed just like my other experiences with women. I could feel us both get hard in our panties as we rubbed together and he immediately reached down and pulled out my cock from my dress and started rubbing it. Then he went down on me and gave me a great blow job. I don't cum from blow jobs really, but it was great anyway. We moved positions a bit, and then he took off his top and showed his bra. He also removed his panties and his cock was poking out from the garter belt...it was pretty hot. I grabbed his cock and started stroking it as I made out with him. I even took both our hard cocks and rubbed them together. Eventually I decided it was time to take the plunge and suck him, so I just went down and went for it. His cock was probably about 5 or 6 inches, so it was easy to handle, and I was surprised how natural it came to me. I practiced on dildos, but this was much better. I could feel him shaking with excitement as I went down on him so I knew he liked it, which made me get super hot and hard. I pulled down my panties and started jacking off as I had him in my mouth hoping for him to cum so I could try that. I think he was having a hard time with that too. It got tiring after a while, so we decided to take a break and he asked me if I would put on just lingerie, and of course I agreed. For me it's a big turn on to be told what to wear. I grabbed this red and black bustier with garters and thigh highs and kept my black panties on and slipped back into my heels. He said he thought I looked hot and I immediately went on top of him as we kissed and he grabbed my ass and slapped it. He then turned me on my back and laid me on the bed sat up on me as our cocks rubbed together. After that he began grinding me and feeling up my body. I kept getting excited and told him I was going to cum. He said he wanted me too, and I exploded on my bustier. He got down and licked it up and shared some with me in a kiss, and then I decided to change into something a little cleaner. So I got a different pair of panties and bra and put on this short blue and black lace dress with no hose and heels and laid down with him in bed only wearing his lingerie without panties. I snuggled up next to him and started grabbing his cock and kissing his neck and could feel him getting hot especially when I started massaging his balls. I told him he made me cum so he should tell me what he wants me to do. Then he said he wanted me to suck his cock like a good little cocksucker, which immediately made me want to do it and so I did. I went down as far as I could and he loved every minute of it, which of course made me love it too. He told me to come back and kiss him more and then we both jerked him off together until he came.
At that point I think we were both pretty tired and surprised how far we went so we just calmed down, watched some tv, and got cleaned up. He left shortly and I stayed the night in the hotel since I had already paid for it anyway.
For me, it was a lot of fun, and it pretty much confirms that I'm probably bi. Although I think if he wasn't so effeminate I wouldn't be into it. I suspected beforehand that I was probably interested in some CDs when dressed, but perhaps not romantically for a serious relationship, and that's pretty much how I feel now. It was hot at the time, but I think I would prefer to be in a serious relationship with a woman where maybe I could explore on the side or with her. I'm sure a lot of you can relate. Questions? I hope I did an OK job telling my story.