My underwear was from a catalog of lingerie for men. It enclosed and constricted my cock and balls. By the position that the material enfolded my genitals, they felt exaggerated and prominent; lifted and pushed forward. Nothing at all covered my ass. It made me feel sexy and a little feminine. Which was fine, since I was going to be fucked like a girl before long. I slipped on a pair of shorts over the silky briefs and a t-shirt above. That was all I needed, it was a warm evening in the city.After a short cab ride to his apartment I was soon being buzzed up.I was surprised, when he let me in, to find that he had a guest. He introduced us and went to fetch some drinks.This visitor was an older gentlemen. Ivan is already about ten years older than me, this guy had to be in his 50s. He said "so you're the young man I've been hearing so much about".I was shocked. This was the first time anyone else had been there and I sure as hell hadn't told anyone what I'd been getting up to.I guess. Before she got out and gave me a long kiss she said “there is an adult bookstore just down the street. We will need some lube and maybe more.Just surprise me and I will surprise you”,she then got out . I was going to ask Carol when I got back how she knew where the adult store was because it was hard for me to find.But I finally found it tucked away in another group of stores and I got a lot of lube. I also got a dildo that was the same size as me but longer .My dick in her pussy and this in her ass was what I was thinking, oh and some male enhancement pills too. I took a pill before I got back to Carol and it was a good thing I did. As I watched Carol walking out from the store I was getting hard. She sure is a beauty I said to myself watching her hair blowing in the wind. Her dress was being blown up and exposing her long thin legs and her fine pussy under it. I gave her a kiss when she got in ,then said “you look so sexy, I can't wait until I get you in the room”.Carol kissed me.
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