Some years ago I cross-dressed as a hot, pirate wench and my girlfriend liked my look at least as much I did, so we had incredible after-the-Halloween-party sex!
We put the outfit together from bits of both our wardrobes and she really seemed to enjoy helping with my hair & makeup.
Even people who knew me didn't know I was the sexy, buccaneer-babe-in-boots who almost won the costume contest that night.
In time, she and I parted ways, but we did replay some role-exchanging after that Halloween and it was not the cause of our break-up. In fact, I miss those days now.
It's been a long time since I got dressed-up for Halloween, but this year I happened to notice an odd shop in the mall and thought I'd like to see what costumes they'd have.
The guy said he was out of costumes, but he'd give me some clothes if I bought the monkey that was hopping around the shop.
"If the little animal gets out of hand all you have to do is spank it. But put on the antique pirate clothes first," he told me.
I dressed in the wench attire as the furry-little-beast jumped & squealed all-around.
Now that I have it in-hand, I'm going out so my furry-little-beast can get spanked!