So I guess before I start I should say that this is explicit at points. I don’t know if that is OK or not.
It has been over a year since the first and only time I've been sexual with a man and it was not a pleasant experience, but I don't entirely regret trying it and want to try again; I've just been hesitating because of last time. I am hoping that sharing the experience will encourage me to try again.
So I had finally decided to try having sex with a man and, since I can't leave my house dressed and try getting picked up a gay bar, I went online. I posted an ad and started looking through other ads and replies and after sharing pick it was mostly no takers. I knew I would have a hard time finding someone because I am not a very effeminate looking crossdresser, but even when replying back to people saying the wanted a big ass they wouldn't respond back. Finally, I had someone message that they were interested and sent me their stats. He wasn't that well hung and was shorter than me, but he was ok with how I looked and was fine with me not getting dressed till I got there. He even suggested for me to bring multiple outfits and pieces of lingerie to try on for him. That sealed it for me so I left for his apt.
I got there with a bag filled with my favorite panties, stockings, and outfits. I knew exactly what I wanted to put on first; this short teal baby doll with garter belt, black stockings with a floral design, and a black thong that held everything place perfectly. I knocked on his door and he quickly opened it and pulled me inside. I was barely even in yet and he already had his dick out, stroking it, as he told me to hurry and get undressed. Since he gave me no room to move down the hall, I stared to take off my shirt. Then he used his free hand and undid my pants and pulled them down to my ankles taking my panties with them. I squatted down to open my bag and take my stuff and said "slow down let me change first please," but he took that to move his cock into my mouth. He had my back to wall and I had to grab his legs to keep my balance, he took that to mean that I was enjoying and ready. He pushed his shaft deeper into my mouth till his balls were slapping my chin (I would say it was difficult to take but his tip barely reached to the back of my throat). He was enjoying himself though as he moved his hips back in forth and said "you better get it nice and wet, I'm out of lube." He then pulled out and took my hand and pulled me down the hall to a bed in the middle of a room. I nearly tripped with my pants still around my feet, but I had managed to pull my panties back up. He told me to lay down on the bed and I asked to get dressed and dolled up first. He reached into my bag and tossed me a blouse and said that would be enough. I put in on and hoped that he was just too hard and that after I pleased him some he would let me get all dressed for him and lied down. He got on top and stared kissing and feeling me up when he asked if I cleaned and flushed out before coming over. I told him of course and he replied good "I don't want you to complain when I put it back in your mouth." He then quickly rolled me over, yanked my thong out of the way, and pushed himself into me. It didn't hurt but it wasn't enjoyable. He liked it though as he got faster and louder. He still had the back of my thong in his hand as he stretched it out more and more, calling me slut and that I should let him know how much I enjoy it. I started "moaning" and he didn't get the clue. He pulled out and said it was getting dry and moved it back to my mouth for "lube" (I had already been practicing ass to mouth so I was fine with it) hoping pleasing him would let me get into something that made me feel sexy. Seeing me suck his cock more made him really turn on and he undid the blouse and started playing with my tits, then pull out so he could start sucking on them. I was now lying here undressed with the only female clothes being a stretched out thong at my ankles and now he was starting to play with my dick. This threw me out of feeling anything like a girl, feeling fem, and I was completely turned off. I started to get up and push him off when his phone rang.
He said his girlfriend was coming back early and pushed me and my bag of clothes into the bathroom and closed door, the blouse was left at the side of the bed. He said he would get rid of her and we could get back to it and closed the door. She came in and starting taking about something, I started to get dressed back in my male clothes. I was rising out my mouth when I heard them go outside in the back. I started to leave but took my now ruined thong and left it somewhere out of sight with a sexy note written in pink lipstick and left quickly and quietly. By the time I was back in my car I got a message saying she was gone and to come back. I ignored it. He then said that it was fun and to do it again. I blocked him. Since then I've looked at other personals, flirted around online, and even had other offers; but I haven't tried again. While my time with him wasn't enjoyable, I didn't hate the taste of a real cock in my mouth and the sex might have been good with someone that took their time. I did enjoy the idea of submitting control to someone, but the clothes are a part of that. Thank you for letting me get through all that. Maybe I'll try again, but try to find someone in person instead of the internet.