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So, as those of you who actually do know me (since I rarely post and mostly lurk), I'm a pretty young guy (25) and I've never actually been to LOS (though it's in the cards). I've dated a few trannies long term over the years, but mostly stick to just dating gg's. Trannies are a fetish for me, so I always go back to ladies when I get tired of them or when we break up.
At any rate, the story. I've lived in Chicago my whole life and consider myself pretty street smart. I used to be a teacher and taught in an inner-city school with over 3,000 students. So nothing could have prepared me for the giant bone-headed move I pulled last night:
I managed to let a tranny steal my wallet.
My mistake. My bad. I take responsibility for it. I've never before let myself get so wasted that I couldn't handle a situation I've gotten into. I mean, I was trashed; I was totally beyond the point where I should have been.
I started out at a fairly nice-sized gay bar called Roscoe's which is dead in the center of Chicago's boys town. To find the trannies in Chi-town, you pretty much have to frequent the gay bars. I'm not into men, so if the trannies are few and far between on any particular evening, then my night will probably suck.
I ended up meeting and having some drinks with a small group of 4 trannies. I eventually make off with Mariah, a very cute half-Italian/half-Mexican tranny. I had never seen her around before. Her friend, Sasha, told me that Mariah had just moved here from Indiana to attend classes. That makes sense because the fall semester just started.
So Mariah and I are hitting it off pretty well. She's cute and funny and she seems to dig me. We're doing all the typical young person stuff like making out in the bar, dancing, groping. She just had her tits done so they're hard as a rock.
We move on to 5 or 6 different bars during the night and I just end up completely blitzed. It's eventually 3:30 am. I'm barely sitting on a bar stool, ready to be sick. I then notice, much to my horror, that my wallet's missing. I start to panic. I had just bought a drink in the bar, so I know I at least had it when I came in.
I alerted the bartender to the situation. He was very nice and cool about what happened. So he helps me check under the bar stools, in the mens room, in the ladies room, and basically everywhere in the bar.
Eventually someone comes up to me and tells me they think they saw Mariah take my wallet and put it in her purse. I didn't want to believe it, because I had been having such a good time with her. But the small crowd in the bar kept demanding she empty the contents of her purse.
Now here's one thing about gay bars: the gay guys inside are almost always the nicest people you'll ever meet. They're helpful, agreeable, and can make you laugh.
So they get her to dump her purse onto the bar, and sure enough, she has my wallet. I'm completely floored. I felt like such an idiot. I've been in the "scene" for four years and had never let anything like this happen to me before.
I thanked the bartender and the patrons, and headed out. I was so pissed off. I felt like the typical vacationer in Bangkok who believes the whore truly loves him.
Ok, so I didn't feel like that, but you can imagine how awful it was to get schooled like that. Life lessons though, am I right?
Thanks for reading. I know this was a long tale. I love these forums!
Anyone have a similar story to share?
At any rate, the story. I've lived in Chicago my whole life and consider myself pretty street smart. I used to be a teacher and taught in an inner-city school with over 3,000 students. So nothing could have prepared me for the giant bone-headed move I pulled last night:
I managed to let a tranny steal my wallet.
My mistake. My bad. I take responsibility for it. I've never before let myself get so wasted that I couldn't handle a situation I've gotten into. I mean, I was trashed; I was totally beyond the point where I should have been.
I started out at a fairly nice-sized gay bar called Roscoe's which is dead in the center of Chicago's boys town. To find the trannies in Chi-town, you pretty much have to frequent the gay bars. I'm not into men, so if the trannies are few and far between on any particular evening, then my night will probably suck.
I ended up meeting and having some drinks with a small group of 4 trannies. I eventually make off with Mariah, a very cute half-Italian/half-Mexican tranny. I had never seen her around before. Her friend, Sasha, told me that Mariah had just moved here from Indiana to attend classes. That makes sense because the fall semester just started.
So Mariah and I are hitting it off pretty well. She's cute and funny and she seems to dig me. We're doing all the typical young person stuff like making out in the bar, dancing, groping. She just had her tits done so they're hard as a rock.
We move on to 5 or 6 different bars during the night and I just end up completely blitzed. It's eventually 3:30 am. I'm barely sitting on a bar stool, ready to be sick. I then notice, much to my horror, that my wallet's missing. I start to panic. I had just bought a drink in the bar, so I know I at least had it when I came in.
I alerted the bartender to the situation. He was very nice and cool about what happened. So he helps me check under the bar stools, in the mens room, in the ladies room, and basically everywhere in the bar.
Eventually someone comes up to me and tells me they think they saw Mariah take my wallet and put it in her purse. I didn't want to believe it, because I had been having such a good time with her. But the small crowd in the bar kept demanding she empty the contents of her purse.
Now here's one thing about gay bars: the gay guys inside are almost always the nicest people you'll ever meet. They're helpful, agreeable, and can make you laugh.
So they get her to dump her purse onto the bar, and sure enough, she has my wallet. I'm completely floored. I felt like such an idiot. I've been in the "scene" for four years and had never let anything like this happen to me before.
I thanked the bartender and the patrons, and headed out. I was so pissed off. I felt like the typical vacationer in Bangkok who believes the whore truly loves him.
Ok, so I didn't feel like that, but you can imagine how awful it was to get schooled like that. Life lessons though, am I right?
Thanks for reading. I know this was a long tale. I love these forums!
Anyone have a similar story to share?
) and when she finally showed she was ok looking. By then I was on my 8 th gin Bombay Saphire martini and whe had a few drinks and me afew more. We then had a whole night planned and I took her up to my room where we got undressed. Me being the bad drinker I am excused myself to the bathroom where I got sick and yacked and I told her I am sorry but I dont feel well can we call it a night. She went ballistic and I almost had to call hotel security. She was cursing me up and down so I gave her $200.00 bucks and sent her on her way while she was banging on my door cursing. she wasnot a hooker. I then hours later and got better and walked down to Gibsons where I hung out at the bar the rest of the night. I actually saw her with friends on the way to Gibsons at Starbucks sitting outside on the patio but luckilly she didnot see me. Stick to gg's if in Chi Town--there are plenty of them and a lot safer bet.
She was not a hooker? (Maybe you were too drunk to notice but she sure acted like one. You could have gotten drunk by yourself. Next time you want to fuck stay halfway sober so you can handle the situation. She was probably a University student at Loyola of Chicago I bet!!! 
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