Doublelist encounter, I did something I have not done in years!
I am a married man in my 50's, prior to marriage I experimented with many facets of sex to include dealings with CD's and T-girls. Recently I was out of state for work (Arizona) and being bored one night I decided to jump on Doublelist to check out the activity, not really looking for action. Long story short, I responded to an ad by a CD calling herself "Doris".
We ended up having a nice phone conversation, she telling me her life experiences and me telling her mine. We ended up setting up a coffee date the next day, "Doris" looked absolutely average as a man, about 5'-2" thin and somewhat pale (34 yers old/White). Doris was however lively and an absolutely incredible conversationalist, I really enjoyed hanging out with her for the 30 minutes we spent at the coffee shop. I extended an invitation for dinner that night )I had to get to work) she accepted and we ended up having a nice meal, hanging out for a drink. I really was not looking for action, I was perfectly content with having someone to hang out with while I was there for the week.
We kept in contact and the Thursday prior to me leaving she called me and told me she wanted to get together for a drink. Of course I said yes and decided on a location not far from the hotel I was staying at. We met, had a few drinks. She smelled really good and I complimented her on her scent and she said it was her favorite perfume (Paloma Picasso). She was obviously dressed as a boy, wearing a nice set of sweat pants and sweatshirt. I was in shorts and flip flops. It got late and she offered to give me a ride so I said yes, We got to the hotel and I asked her if she wanted to hang out (honestly I was horny as fuck but like I said I was not looking for action) to my surprise she said yes and sounded really excited. We parked, got out and then she went to the trunk of her car and grabbed a back pack. We went to my room and she immediately asked to use the restroom and went inside. She was in there for a long ass time but when she came out, she came out as Doris and oh my god was I surprised! She was wearing a wig, she had done her make up and was wearing a bra with matching panties (black with red accents).
I did not say anything, I took her hand and brought her close to me and I kissed her, she responded in kind. It was a great kiss, she was really into it. I could feel her cock getting hard, I was already hard as a rock. She asked me if I wanted to fuck her, I answered her with a question of my own..."do you want me to fuck you?" She whispered yes, gave me a kiss and walked across the room to her back pack. She took out a condom and a bottle of lube and placed it on the night stand, she then sat me down on the bed, took a pillow and got on her knees in front of me. She quickly took my cock out and without a word started sucking my cock. It was a slow and methodical blow job, absolutely mind bending!!! She complimented me for having a "beautiful" cock. Now I do not have a huge cock length-wise but I am fairly thick. Long story short She rode me, I took her in as many positions I could take her, we fucked the night away and spent the next morning fucking some more. I've never had a CD make me cum as many times as she did, she left my room, tired sore, gaping but with a look of satisfaction. I have asked my boss to give me more projects in Arizona