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Gay Hookup with a Crossdresser

Crossdresser Man

I’ll try anything at least once! (Read “MMF Threesomes”). And when I’m cruising online, there are always crossdresser profiles kicking around. I had never hit one up, for what I always believed to be “logical” reasons:

  1. Too niche. I wouldn’t know what to do with a crossdresser, let alone what was expected of me.
  2. A crossdresser wouldn’t be interested in me anyway, because…well, who knows why.

But recently (again, who knows why these things happen…) a cross-dresser’s profile jumped out at me and I couldn’t keep away. Posing in full lingerie glory, he looked gorgeous, his profile was smart, and he included a cockpic that had me gasping for air. What did I have to lose, I thought — worse case scenario, he’d block me.

Not so. He fortunately dug what he found in my profile (or he was desperate that night, we’ll never know) and agreed to hook up. When I told him I’d never been with a crossdresser before and was unsure about what was involved, he stepped up to the plate as though he were slipping into silk panties.

“Meet me in an hour. Leave the rest to me,” he said.

Flash forward: the night ranked high enough to earn a post on this blog — not to mention a follow-up date this coming weekend.

I can’t speak for everyone’s experience with a crossdresser, but here’s what I learned:

  • Wearing those clothes made him feel so freakin’ sexy that it transformed him into an irresistible fuckpot. The energy was like nothing I’d ever experienced.
  • There’s a “performance” element that made me feel like I was in the room with multiple partners. How can you not love that?
  • I thought I had a vivid imagination: try taking a backseat to a guy who loves to feel sexy in women’s clothes!
  • It’s amazing how something as simple as a lace camisole ups the feeling of taboo (likely due to the raging boner popping out beneath it).
  • Hearing smutspeak whispered in your ear from the lips of a guy in silky clothes is an easy way to become painfully engorged.

It was another life-changing reminder to NEVER write off anything unfamiliar too quickly, lest you miss an opportunity for awesomeness.

Besides, at the end of the day, once the clothes are off, it’s all cockcockcock!

Be safe!

Check out: Crossdresser Dating and How to Meet Crossdressers

Tell us what you think!

Tell us what you think!

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