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Crossdressing Dare - Thats Embarrassing!!

Submitted By : Paul

On a senior trip to New York, all of my friends, girlfriend, and tons of other people went with me. My senior principal and history teacher were both with us as well.

Anyway, we were all in the apartment in my room late at night and I got pretty smashed. While I was drunk, we all decided to play truth or dare. It was pretty moderate for a while, (considering we were all shitfaced), some kissing, some flashing, that kind of stuff. Then when it came time for me to be dared, the girls and my girlfriend all gathered togather, whispering, trying to devise something really good. When they finished, they told me they decided to have me crossdress. I was pretty tipsy, so I said "why the hell not?"
So the girls had a great time dressing me up, getting me all ready for my "debut". I borrowed panties, tights, really slutty leather outfit, and lots of makeup, painting my nails and all. Someone even picked me up blonde wig. (I must say I looked pretty good. I know; they took lots of pictures.
So when I was all dressed up and we felt like we had finished playing, my friends and girlfriend and I decided to go get some more liqour. But when we went out to get some more, my friends dropped me off in a gay bar, all dressed up. I kept getting grabbed and harrassed and I had to call a cab. When one came, he took me in the direction the hotel, but stopped a mile away. He pulled into some lot and put his hand one my thigh. I went to get out and the dirty man put his hand farther towards my penis. I ran out and had to walk in a drunken stupor home. When I got there and passed the curious other tenents, I came to what I thought was my door. But when i tried to break it down when it didn't open, my principal came to the door.

I didn't get in trouble for drinking, being out, or crossdressing. The principal was too hysterical to punish me..

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Score Votes Rate it! 3.9 1 - Not Embarrassing 2 - Some mild blushing 3 - Red Faced for the day 4 - Paper Bag over head job 5 - Crawl into a hole and die!

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