CD first time with a guy
I have been a closet crossdresser since my early teens. In my 20’s I would stead to go on webcam and let men pleasure themselves while watching me use my dildos but I never showed my face. About 10 years ago I was in a chat room and was talking to a guy who lived local who saw my pictures and wanted to hook up with me. We decided to meet the next day at a local motel. That night I shaved my entire body and painted my nails. I couldn’t sleep that night thinking about all the things this guy was going to do to me. In the morning I packed my bag and headed to the hotel room while he was at work. I spent the day getting ready, makeup, hair, I put on a cute pair of panties that said “ride me” on the asscheeks. I put in a little black bra, and proceeded to put on the sexiest little mini dress I had. Then I put on my 6” black pleaser heels. I had some time so I had a couple of glasses of wine as I admired myself in the mirror. Then the text came through….. my boy toy was out of work and on his way….he said he would be at the motel in 15 mins and asked me what room number. I began to panic as the realization was setting in that I was about to get fucked in the ass for the first time…. I texted “room 218” as I thought to myself , there’s no turning back now. I checked myself in the mirror and put on some more lipstick when I heard a knock at the door…..oh no!! This was it!! I was trembling as I opened the door facing this man who towered over me even with my 6” heels. I squeaked out a hello in my little girl voice as he came in and started to undress as I just stood there watching him. Before I knew it he was standing next to me in his underwear, I reached over and began to rub his cock through his underwear and he was already rock hard. I had never rubbed another cock before, and this one was bigger than any of my didos that I had practiced with. He pulled me closer and started rubbing my ass through my miniskirt as I reached in his underwear and started stroking his massive cock. Then he took off his underwear and lied on the bed. I bent over the side of the bed and began to kiss the head of this massive clock while I rubbed his balls, and I felt him reach behind me and pull up my skirt so he could look at my ass in the mirror while slid the head of is cock in my mouth. I was so turned on I almost came right in my panties. Soon I felt his hand slide under my panties and he stuck his finger in my little asshole. I was in heaven!!… after about 15 minutes he stood up and pulled my little dress to the floor and my hard cock was sticking straight out of my panties which were already soaked with pre cum. I knew what was next…….it was about to happen…..I reached and grabbed a condom and put it on him and slid my little panties off onto the floor. He said “get on all fours” I climbed up on the bed and felt his massive cock press against my tight asshole. Then before I realized what was happening he pushed his whole cock in me and I felt his balls hit mine….. I was in horrific pain for a split second which immediately turned to pleasure as he began fucking me slowly. As he kept thrusting faster and faster I could feel my own cock bouncing against my stomach and dripping cum all over the bed. I now felt like the bitch I always wanted to be. Then he said “ I’m going to cum” . I jumped down in front of him and he took the condom off and stroked his cock until he came all over my face and chest. It was so hot!! This is a true story!!