Raunchy Role Play

We want you to dish the dirt on your sexiest dress-up shag! Were you the naughty school boy being punished by the headmistress? The damsel in distress being rescued by a hunky fireman? The horny housewife needing her pipes cleaned? We're suckers for a sexy role play here at the Pie, so spill your beans and we'll spill our...cash award...for the sexiest entry!


December 2020 Submitted Sex Secrets

Overall Winner
Posted: Dec 20, 2020
My first man-on-man partner M has shown interest in my cross dressing fantasies, and encouraged me to come dressed as ‘Sarah’.



So dressed in women’s fitted jeans, heels, a push up bra and simple fitted T shirt I walked through the cool autumn air and arrived at his apartment. Whilst not ‘passing’ above the waist, I did have an ass and legs that many women were jealous of. The lift up to his level was a little awkward as a gorgeous girl in her late 20’s eyed me up and down, and smiled knowingly



I chattered with M on the couch for ages, enjoying each other’s company. He then disappeared to the toilet, and I stood to check my phone. He returned, coming up behind me, grabbing my ass with intent. I smiled, and pushed back into him, before peeling my jeans off and bending at the waist to remove... read more
"M has shown interest in my cross dressing fantasies, and encouraged me to come dressed as ‘Sarah’.."

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