I’ve (m)ade a huge mis(t)ake

So I got drunk. Really drunk… The kind of drunk you don't wanna be, because you make stupid mistakes. This mistake was the worst I've made. I just broke up with my girlfriend of a year and eight months. Why'd you break up you may ask. Well we all got drunk and fucked her best friend beside her while she was asleep. That was shitty, but it led me down a rabbit hole of whoriness I've never experienced. About a week after our breakup, I had been looking at craigslist casual encounter ads. Sure, I thought, I could fuck one of these people. I had always thought about fooling around with a guy, and I even emailed a couple guys but chickened out at the last minute. But then I saw a transexual post. I have been curious about trans girls for awhile now, and my drunkeness made me more ambitious. She was a bigger african princess it would seem. She wasn't really a princess, more of a hooker, as I paid her money to have sex with me. So I texted this chick. She seemed nice. Wanted $100 for a half hour of fun time. I told her I would get the money and meet her in a few minutes. I drive to her apartment, (this is all with me being VERY drunk btw, I probably wouldn't have done this sober) and wait for her. She shows up and we walk upstairs to her apartment. We walk in and I notice her place doesn't look too great (considering the area of town we're in). There's a black leather couch and an area rug. Random paintings are hanging on the wall. As I said before, I am very drunk, so I excuse myself to the restroom. I relieve myself and look in the mirror. "You're about to have sex with a transexual." I said excitedly. I have fantasized about this for years and never thought this would come true. I enter her bedroom and she asks for the $100 we had previously mentioned. I gave her the money and she pulls out a condom. She places it on my cock and takes off most of her clothing. I can see her sexy black cock and wish I could be playing with it, but I want her to play with me first. She begins to suck on my dick like there's no tomorrow. It feels amazing and I almost cum as she laps up my cock. She tells me to fuck her from behind. I oblige. I stand up and she assumes the position. I lick her asshole real quick and try to enter her. Something's wrong… I can't get inside of that beautiful tranny. I try and try again to no avail. She asks what's wrong and I say it's probably due to my drunkeness. She says don't worry and has me lay down and starts sucking me off again. By this point I am discouraged and can't get hard anymore. I try to fuck her sweet ass once more but cannot muster up the hardness to do her. I admit defeat and tell her I'm so sorry. She tells me she's worried I am mad her, which is the complete opposite, as I wanted to fuck her so badly. I realize that buying a transexual hooker, while it's sexy in my fantasies, is probably not what I actually want to do. She understands and we say our goodbyes. Everything in me wants to fuck the shit out of that bitch, but I can't bring myself to. Whether that's the alcohol or the straight talking is beyond me… I guess I'll understand tomorrow. Thanks for reading, this literally just happened. Sadly I'm out $100 but maybe that's a lesson learned. Don't try to fuck tranny hookers! Maybe that's the lesson…

Source: reddit.com/r/gonewildstories/comments/3b2606/ive_made_a_huge_mistake