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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. An ultra scrawny me in a swim suit. Me in a cub scout uniform. Et cetera.I stayed in the room and didn't begrudge her a moment of showing off how nice her Robbie had turned out. It was a Mom moment. I smiled at her doing all of it. I thought for a moment what Lyn's scrapbook would be like. Pictures of her winning prizes in horse jumping shows, no doubt.I excused myself at some point to use the loo, and paused to eavesdrop before coming back.Mom was saying, "You know, he's never brought a girl –. More

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