Going the rest of the way
As a college freshman, a girlfriend talked me into letting her put makeup on me. When she was finished she said I could open my eyes and see. I was stunned. I was looking at a very sexy, hot-looking girl in the mirror. I was instantly turned on. For a micro second I saw a hot, sexy girl. My jaw dropped. My gf laughed so hard she fell over on her side. I was embarrassed that I got horny looking at my own sexy face. It scrambled my brain. That was MY face, eyes,....and lips. Fuck me. If a guy had seen me looking like that he would have wanted to fuck me.
Actually, I wanted to fuck me. I wished she had planned this better, had brought a skirt, pantyhose, etc and had talked me into putting them on as well. But when she laughed I knew she was laughing at me. Maybe she thought a real man wouldn't have been talked into it, or that my reaction had failed a sissy test or something. I felt busted, humiliated, and secretly turned on by it all, but I needed to hide it. It felt like I was the butt of a joke.
It's a good thing times were different back then. If I had known how many adult men and women are into young, pretty, sissy boys, and if I had known how to find women who would help me with my cross-dressing, party favor fantasies, I might have gotten heavily involved in that scene.
I really looked good, I'm not just saying that. I was still very thin and not well muscled yet. And I was pretty. I lived very near Palm Beach, FL, and those rich people like having sex parties. I probably would have become a party favor. I would have gotten used to anal, good at blowjobs, etc. and been very popular. I might have contracted HIV from all the sex. So it's a good thing I didn't find try to find someone who would help me with my feminization fantasy back then.
Still I can't help wishing I had tried getting dolled up, made-over and crossdressed back then. It would have been so fun to look hot and sexy. I have a girly boy butt that girls love. (I know some people have always wondered if I was a secret sissy just because of my butt; they think a guy with a cute butt like mine probably worked at making it look like that.) I used to twerk it and think about cross dressing wearing a short skirt for Halloween. (The thought of showing my butt turns me on, makes me feel sexy, dirty, notoriously humiliated.) The reason I never did that is that I felt sure it would start rumors. Somehow word would get back to people I knew. Guys just didn't do that back then, not unless they were fags. And I didn't want that reputation (and still don't).
But I still think about it. I'm no longer a skinny kid with a young pretty face. But I believe I could still look good. I may save up some money and take a vacation in Chicago or somewhere, hire a Mistress who specializes in feminizing and humiliating men, and 'work' as a slutty looking sissy waitress at a BDSM club, or something like that. I want people at the party to notice me, talk about me, point and giggle, tease me, and palm my ass as I wait their tables. I want women to be amused and entertained, and use soft persuasion to encourage me to 'have some fun' with the boys. I want them to watch as I eventually give in and 'act like a girl', suck dicks, get bent over, and make faces as that first dick works its way up my butt. I want them to watch me get fucked long enough that I cum from anal. I want them to tease me as I go back to serving drinks, walking funny. The aspects that turn me on about this are the embarrassment of being feminized in a slutty looking way, softly persuaded by women to give blowjobs and butt sex to horny men, then laughed at because I did, and because I had anal orgasms from their dicks stabbing and pounding deep into my ass.