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In 1988 my wife/mistress and I were invited to a closed door Toga Party like this one where everyone was tested and the shemale were hung aggressive tops. The party was sponsored by my wife’s pimp when she was hooking. I wasn’t a virgin because my wife made sure I lost my anal virginity right after we married but I’ve never had sex with a shemale. My wife knew her from the business and definitely wanted to take my ass at the party. The party had experienced hookers and rich guys. Lots of good hors d’oeuvres, food, champagne, and open sexuality. I watched my wife satisfy guys with big cocks and made huge hundreds of dollar tips. One guy pushed 10, $100 bills rolled up into her ass and she quickly retrieve the money and let him fuck it. He had a big dick and she enjoyed getting pumped up her butt. I had a sexy black shemale push me to my knees slipping her huge cock in my mouth to suck hard. I was the first guy of the night to take it in the ass everyone watched this beautifully hung shemale Fuck me into a Sweat crying out as she plunged in and out of my tight butt hole. My wife cheered me on and after she came inside of me, my wife whispered that I could take getting fucked by a shemale off my bucket list. My wife’s pimp rewarded me with his favorite hooker, who took good care of me after that.
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to bathrobe_man : true but back then AIDS was still pretty much untreatable so any one who was considered a risk had to cover up if they wanted to be hired
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