When I was a senior in HS, I had a gf that when her parents were out of town, at least once a month, she's had me over and it was her "fuck me day". She was on birth control so I road her bareback all the time, but there was one thing I had to do for her before she'd fuck. She always, and I do mean always on these "fuck me days", did me up with her makeup and she even used lipstick and eye shadow on me. She then dressed me in girls clothing. The whole 9 yards type of thing, heels and stockings, garter, panty, bra, and either a dress or a blouse and skirt.

She'd start by pulling my cock out of the panty and giving me a blowjob, then it was basically anything I want for the rest of the day until I was completely fucked out. Maybe it was her way of assuring I'd never tell anyone, but she was the most degenerate fuck I've ever had the pleasure of laying. I fucked her mouth, and she always swallowed. I pumped gallons of cum into her very willing c**t, and she would even let me dump my load into her tight ass when I wanted it.

One day she did something that really pissed me off, and I just looked at her and said, "I should give you a good spanking!" She looked at me and said, "You wouldn't dare." I put her over my knee and spanked her ass red. She was so excited afterward that after I was fucked out, she was still masturbating like crazy. I watched her fuck her dildo for an hour, then I climbed back on her and dumped an other load in her c**t and one more in her tight ass.

She seemed to get kinkier after that, and always wanted me to fuck her.

I did her as much as I possibly could arrange until she went off to an out of state college, and I went to a local school. The dressing up like a girl still bothers me sometimes, but then I remember how much pussy I she freely gave me and those twinges of guilt just fade into a big fat smile.