I had been experimenting with crossdressing with my gf for a while, enjoying her strap-on. However, I knew that I would not feel like a proper girl until I had been with a real man. So I posted an ad and got a lot of replies. I chose a 40 y/o married guy (me being in my late 20s) who said that he had a lot of experience with guys. We agreed for him to come over at lunch time. I showered and shaved and then put on my black stockings with opening at the front and rear, a black mini skirt, black lacy undies and a black tank top borrowed from my gf. When he arrived, he sat down on a chair in the bedroom. He asked me walk like a girl for him and I obliged. He undid his trousers and commanded me on my knees. Of course I went straight to sucking his dick. It was long and thick, and he enjoyed the attention of my mouth. All the time he felt me up in various places, and seemed very fond of my ass. After a while, he told me to remove my undies and grabbed the dildo I prepared to stretch my ass. I had to bend over the bed, while he was playing with my ass. Having put on a condom, he told me to sit on his cock. It was my first time with a real cock, and the strap-on had been much thinner. Despite a lot of lube, it was painful, and it took me a couple of attempts before his cock found his way into my virgin ass. After just sitting on his cock for a bit, I started to ride it. The pain was passing and I began to enjoy it. Next, he took me doggy style and started to properly thrust his cock in and out. Then, he turned me over onto my back, with my legs over his shoulders. He liked to see my open pussy and re-entered me many times. He was getting quite close to cumming, and wanted to finish doggy style. It didn't take long until he climaxed. He cleaned up and left, without even having touched my cock - treating my like a slut.