My First Experience with a Cross Dr

Back ground. I had started enjoying anal sex with a early girl friend at 19 and later, when I met my future wife, I introduced her to it and we both really got into it and it was our favorite sex act. We were both very open minded and did some swinging. I was fairly dominate and she was pretty submissive and really got off on me setting her up for a threesome and I got off on how hot she got during them, She would come time after time. She would sometimes rim my ass and use a vibrator on me so I knew how hot your ass could be. She never minded that I had a girl friend here and there. Unfortunately, she got a brain tumor and passed away.

After that I had several short term lady fiends and although a couple of them would have anal sex with me, but it wasn't as hot.

Then, I was out of state running a construction job and started browsing Craigs list for a hook up and after not having much luck finding a woman, and thinking a hot ass is a hot ass, thought what the hell and checked out the Cross dresser TV ads. One by a 22 year old college student who wanted to find a mature man to feminize and dominate him sexually sounded hot. We emailed back and forth then started texting. I was making some great money, so I agreed to get him some clothes and make up. At a Lovers shop, I bought some panties, a corset with garters, some lacy nylons. Then went to a department store and bought some black high heels, lips stick, eye make up etc.

I go a different motel room and had him meet me there Saturday evening. He was short and just a bit stocky, but, from our text I knew he was very willing and excited about doing it. First thing I did was have him strip, put on the frilly panties, then the nylons and corset and hooked the garter straps too the nylons. He had a hard on before he was even dressed up. LOL so did I, but I still had my pants on. First I put lip stick and then started putting make up on his eye lids and using the eye line to trace under them. I would let him look in a small mirror as I did that. He definitely looked more feminine with makeup and as I used darker colors kind of slutty. When I was done I told him from now on he would be Missy and to stand in the heels and turn around. Then, I took her in my arms and gave her a deep kiss, sticking my tongue to her throat, Missy kissed back and we kissed and tongued each other for quite a while while I ran my hands on Missy's body. Then I broke the kiss and had Missy kneel. I told Missy to take off my pants and once she did I told her to kiss the head of my cock. I then I started telling her how to use her mouth and tongue on me as I held her head. I almost came, I had her stand beside the bed with her hands on it, I went being her and started licking and tonging her ass. I could tell she really got off on my tongue in her and moaning and her ass was more and more relaxed and wet from my tongue opening it. I finally stood up told her it was time for her to learn how to fuck. I put some lube on my cock and ran the shaft up and down the crack of her sweet ass, then placed the head against her and said, press your ass on me and she did with an oh moan as she felt me go in. I went in and out a couple times then started going deeper, then sliding back till just the head was in then forward deeper than before. After about the 3rd time she was pressing back wanting more and trying to keep me from moving back. I said you like to feel my cock in you don't you and she moaned yes. I pulled back to so just the head of my cock was inside and said do you want my cock and she said yes and I slid my self all the way inside and she bucked on my cock and said oh my god and started trembling. I finally came hard deep in her ass and she said she could feel it in her. After resting a while and having her clean up. I washed my cock and had her suck me hard again and then fucked her a second time.

I was on that job 2 months. Missy started wearing panties full time and would come over every Saturday night get dressed and put on made up and I would have her suck and fuck me. I have been over there and seen Missy twice since and fucked her both times. She regularly spends time as a feminized sex slut now