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Gay Stories
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Bi-Sexual Male / 25
Crossdresser Nightmare
I'm a bi male but at the time of this story, I'd only had GF's and had never been with another man. But I did crossdress and after a while had become very proficient at making myself look like a woman, albeit a trashy one.
One of my friends was getting married and as a sendoff for him, we all went to a small greek island for the last vacation of his single life. We had a great time, lots of alcohol and local girls. On the second to last day, the bachelor boy decided that we all dress up as women as it would be funny. I didn't know what to, do I make myself look ugly so they don't think I dress up all the time or go to town and not care. I went to town, full makeup, wig and black cocktail dress and black pantyhose I'd bought from a store.
Everyone else looked terrible and here I come looking like some hot teen looking for action. I made some excuse that I'd watched my sister getting ready that I'd learned how to do makeup, not sure they bought it but as the alcohol flowed I didn't care.
Towards the end of the night, we were all very drunk and in one bar this really handsome guy started to hit on me. To begin with, I ignored his advances and just laughed, trying to tell him that I was a guy, but he couldn't speak a word of English. He started to get a little more forward by constantly putting his hand on my thigh and stroking my leg. I kept pushing his hand away but he was very insistant. I thought i was with my friends so didn't want them seeing me with another man, but to my horror they'd left the bar without me noticing and now im on my own.
One of my friends was getting married and as a sendoff for him, we all went to a small greek island for the last vacation of his single life. We had a great time, lots of alcohol and local girls. On the second to last day, the bachelor boy decided that we all dress up as women as it would be funny. I didn't know what to, do I make myself look ugly so they don't think I dress up all the time or go to town and not care. I went to town, full makeup, wig and black cocktail dress and black pantyhose I'd bought from a store.
Everyone else looked terrible and here I come looking like some hot teen looking for action. I made some excuse that I'd watched my sister getting ready that I'd learned how to do makeup, not sure they bought it but as the alcohol flowed I didn't care.
Towards the end of the night, we were all very drunk and in one bar this really handsome guy started to hit on me. To begin with, I ignored his advances and just laughed, trying to tell him that I was a guy, but he couldn't speak a word of English. He started to get a little more forward by constantly putting his hand on my thigh and stroking my leg. I kept pushing his hand away but he was very insistant. I thought i was with my friends so didn't want them seeing me with another man, but to my horror they'd left the bar without me noticing and now im on my own.
- That's Juicy! 15
- Remove It! 3


