Something most people probably don’t know about me is that I cross dress. Not so much anymore, though I still do on Halloween. I used to own three dresses in high school, though even if I still had them, I would never fit into them. I got a kick out of doing it just to get dirty looks from uptight Indiana natives.
I wouldn’t feel the least bit of shame in admitting I were gay if I was, but sadly, I am not. I say sadly because I would love to get away with casually throwing around a word like “fag,” but I can’t pull it off. I love tits too much to feel right doing it
I used to cross dress because it attracted the kind of girls I like: freaks. Forget well adjusted girls with good childhoods and self respect, I like ’em used and devoid of any limits, maybe even a little bit crazy. If there’s one thing that is true of a crazy girl, it’s that the sex is amazing.
So one day, my relatively liberal religious high school (Brebeuf Jesuit in Indianapolis, in case anyone is curious) allowed the students to come to school in costume for Halloween if you donate a dollar to some charity. So, I go dressed up in a slinky black slip dress. In case anyone cares, my costume was “whore.” My girlfriend at the time was dressed as my pimp. Pictures are pending (I think I have a few somewhere…). [Found them, and posted here.]
I didn’t even get through the first class before I was called to the dean’s office.
For anyone with any shame or insecurity, I imagine this would have been uncomfortable, but I was laughing with the secretary in the office while I waited. We knew each other relatively well, partially because I was always getting sent in to be punished and partly because I often finished my exams first and would be sent to the office with the class attendance schedule, so I would often linger in the office to shoot the shit rather than go back to sit quietly in the room as everyone else finished.
Things got a little heated when the former football coach saw me. Now, at the time, I was on the football team, and he was no longer the coach because of an… incident. After a game we lost, despite having a halftime lead, he flipped a table. Not a folding table, but one of those black stone-top tables I see primarily in chemistry labs. To be fair, we fucked up (though not me, because I wasn’t even good enough to take the field).
I was actually sitting in the front row during that incident. I remember looking over at another player, Chris, and he had the most strained look on his face. He was trying his hardest not to laugh hysterically, and it made me want to laugh. We definitely processed that situation differently than Matt in the back corner of the room, who was sobbing.
So anyway, the former football coach is braying, “Ohhh hell naw! No, Bret, no no no no no. No. No no no no no no.” I remember a lot of no’s. He sort of left the office shaking his head. He was still the acting Assistant Dean, because I guess they couldn’t revoke his position after he resigned as coach. He was gone the next year, however.
The actual Dean was the basketball coach. I had tried out and I had a good rapport with him, even though I didn’t make the team. I basically gave him an out: the dress didn’t meet dress code, since the straps were not two fingers width. I offered to wear a shirt over it, but he just shook his head and said he couldn’t let me do that.
So I changed. Even though there were people dressed up as devils and serial killers, I was not permitted to dress up as someone of the other gender… on Halloween.
*sticks hand out*
Oppression pity, please.
I’m kidding, I’m fine. Hopefully you had a good laugh at the whole thing.