Straight Male / 23
Last week, Halloween weekend, was a blast for me. I'm SWM, 23 who LOVES crossdressing. I got to spend from Fri night thru Monday dressed in drag. No body hair, wigs, makeup, and 20 polished nails. And my mom is totally cool with it! Friday night I lounged around in on of my mom's bathing suits, fully made up and in spike heel sandals. Saturday I helped out with the neighborhood Halloween party for the kids dressed as a cheerleader, but with hi heel pumps instead of sneakers. Sunday, a grownup Halloween party where I dressed in one of my mom's cocktail dresses and sling back spike heels. And to top it off, on Halloween, Mom and I walked in the Greenwich Village parade.
I was a French maid, in a micro short maid dress and 5" peep toe spike heel pumps, and mom dressed in a man's tuxedo. She's 5'10" and I'm 5'5", so visually we looked pretty cool. And to push the visual, I wore a black dog collar and mom had me on a leash!! This is when tucking your junk back between your legs is important, because I was very aroused by this scenario. When I wasn't doing these events, I still wore womens clothes and heels. (I love heels... DUH! LOL!). My feet had already felt it by Monday, but somehow the pain was pleasure! And I then walked/stood in heels for over 6 hours without sitting Monday night. My feet were killing me and my back was stiff, but I enjoyed every second of it. Today I'll put on the French maids outfit and clean the house.
I was a French maid, in a micro short maid dress and 5" peep toe spike heel pumps, and mom dressed in a man's tuxedo. She's 5'10" and I'm 5'5", so visually we looked pretty cool. And to push the visual, I wore a black dog collar and mom had me on a leash!! This is when tucking your junk back between your legs is important, because I was very aroused by this scenario. When I wasn't doing these events, I still wore womens clothes and heels. (I love heels... DUH! LOL!). My feet had already felt it by Monday, but somehow the pain was pleasure! And I then walked/stood in heels for over 6 hours without sitting Monday night. My feet were killing me and my back was stiff, but I enjoyed every second of it. Today I'll put on the French maids outfit and clean the house.


