Kinky Confessions

Kinky Confessions: Wig Out!

Guy in Blonde Wig

Although I love the shopping factor (browsing to find exactly what you’re looking for) of online dating sites, I still like the good old fashioned bar scene for meeting men. It’s a crap shoot, for sure, but the unpredictable factor is part of the high. Sometimes I’m just hanging at a local, looking for a game of pool or sitting for a drink to take the edge off after a miserable day at work, and bang!, in walks an interesting specimen.

He sat at the other end of the bar, so I sent him a drink. Soon he was shimmying up beside me, and I knew there would be something going down. He was the greaser type, white t-shirt, tattoos, and sneakers, but older and a little worse for wear – a definite bad boy with a past.

We walked to his place, a loft apartment in a warehouse. He immediately began stripping down, saying he never wore clothes at home. He was hairless – his chest, legs, everything. I didn’t comment, but I wondered what he was going to think of my hairy bush. The bald trend never caught on with me.

We climbed up to his loft and I noticed a couple wigs, red and blonde, hanging from nails in a beam. Halloween was a few weeks earlier, so I didn’t think much of it. When I was down to my panties, he told me to close my eyes. I did – I love surprises. When he told me to open, he was wearing the blonde wig and red lipstick, and he’d pencilled a mole above his lip. I was in bed with Marilyn Monroe. Fuck! My juices were drying up fast. I laughed, nervously.

“What do you think?” He asked, his bad boy voice now a soft lilt.
“I don’t know. Was this your Halloween costume.”
“No, honey. This is my kink, my thing”
“Do you mind if I have another beer.”

I climbed down the loft’s ladder and was ready to hightail it out of there, but I was intrigued, and he appeared harmless. I fetched a brew from the fridge and downed it. If I was going to fuck with a cross-dresser, then I definitely needed to relax.

“What do you want me to do, sugar.” I said, thinking he might want me to take the lead. That’s when he pulled out a strap-on and asked if I’d ever used one.

I couldn’t. I just couldn’t. Playing along with his wig fetish was one thing, but my sexual sensibilities were all messed up. I’m still trying to figure this guy out. I left without any fuss, apologizing for being uptight, and I never saw him again.

I’ll admit, I’ve only been online dating since. Maybe the bar scene isn’t so great afterall.

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