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I love to crossdress, I am gay and a Bottom. I also have a huge latex fetish and, at the time this story took place, was not new to having rubber sex...and being fucked by other Rubbermen, However, I had never had sex while crossdressed. This is about the first time that I was fucked as a Sissy in full drag.I was reading the dating page in one of those local add papers. There were sections for men looking for women, women looking for men and 'others'. I saw a listing by a CD who lived about. Mark grabbed the edge of the blankets and pulled. I spun like a top on the bed and ended up on my stomach with my head and upper body off the edge of the bed. I shot forward between Mark’s legs but Mark grabbed the back of my bikini bottoms. I pulled at the fastening ties on each hip and my bikini bottoms popped off. I tried to crawl away but Mark grabbed my ankles. Mark bent over and easily picked me up. He turned around and lowered me down to my feet. “We can do this the easy way or the hard. He got a fresh, large speculum was removed from the drawer and rinsed it before handing it to Dave to insert. Dave reached over and parted my lips, confidently inserting the instrument deep. Expertly, it was turned and opened wide. Dave was living his dream, and his smile could be seen plainly through his mask. Then, Dave took a fresh anal speculum from the drawer, lubed it, and slid it right in. He opened it as far as he could, then stood back for the doctor to check. I heard the soft click of. "Equi... ?" Equitador," Evelyn said gravely. "Master of the horses." She seemed to consider her explanation for a moment, and then: "Maybe it's easier to show you."Turning to one of the pairs of legs around the table, she held out her hand and with a look of concentration on her face, she made a beckoning gesture, like a stage magician drawing some object across the table.After everything that had happened so far, I didn't think that I could be surprised anymore; but my jaw fell as I watched.
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