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My First Craig's List Threesomethis story is part of the FanClub (fm:threesomes, 1563 words)

Author: Pegging Picture in profile
Added: Jan 26 2020Views / Reads: 1592 / 939 [59%]Story vote: 9.42 (12 votes)
A sexy, passable crossdresser goes online looking for a woman to fuck and ends up with more than she planned...
 


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I met Susan on Craig's List. This was 2012. I was a recent college graduate in a new city spending most of time outside of work dressed as a woman. It was easy enough to meet people for sex in dance clubs and fetish bars, but the internet offered the chance to find people who were a little more reserved and curious.

At this point I had more women's clothes than men's. I had long dark hair. Aside from work and the gym, I lived my life en femme and nobody ever suspected a thing. I had mastered passing. I was the perfect trap.

Susan was a few years older than me and recently divorced. She'd made the mistake of marrying a "missionary with the lights off" guy and was just discovering herself sexually. She'd experimented with BDSM and learned she enjoyed the kink but not the role play. When I met her she was casually involved with a sensitive hipster named Jim who got off on her exploring her bi-curious side. She'd given it a few tries but always ended up disappointed. She just missed cock.

That's what led her to me. I wasn't shy about posting pics on my ad. I didn't want anyone to assume I was a hairy old guy stuffed into his wife's panties. I knew I was sexy and exotic. Susan said she found me attractive and was curious to experience the best of both worlds. So we exchanged a few emails and agreed to meet up for drinks.

...

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