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Welcome to Great Moments in Drunken Hookup Failure, where we showcase five heartwarming true stories of drunken love gone horribly awry. Off we go.

Transvestites ahoy this week, men. Nothing worse than fucking up a potentially memorable evening with a sweet piece of manpussy. But first, we ease in with the hetero stuff:

Michael:

Kyle had been hooking with this girl for about a month. It was the kind of thing where they would go out on the weekends both get shit faced and eventually meet up at the end of the night to hookup. This particular night was Kyle's initiation for the frat that he was pledging. So naturally he was more fucked up than normal. He blacks out and the next thing he remembers he is making out with his girl in the common room of her dorm. She is also really drunk and eventually grabs his hand and takes him to her room. They start to mess around and eventually they are both completely naked. Kyle gets a few thrusts in when it hits him. He suddenly realizes that he has to take a piss, it is such a powerful force that there is no way that he could finish up before going to the bathroom.

So very politely Kyle tells his girl to hang on one second and exits the room. In his drunken state he neglects to put on even a single article of clothing. Walking down an all girls hall in nothing but his birthday suit, he safely makes it to the bathroom and relieves himself. Kyle stumbles back to his girl's room using the walls to support himself, only to find that when he gets there the door had locked behind him when he left the room... He brilliantly gets the idea that because its 3 in the morning and everybody else is asleep, it would be a good idea not to knock on the door but to instead sit down in the hallway butt naked and wait for his girl to eventually open the door.

However, he had failed to realize how sleepy alcohol makes you and his girl had already fallen asleep and was not going to open the door anytime soon. Experiencing the same effects, Kyle promptly falls asleep. He is now lying spread eagle in the middle of an all girls hallway with his dick sicking straight in the air. Granted at the time its still 3 am and no one is awake but someone who had done as much drinking as he had doesn't wake up very easily... Long story short he lied there until 9 am showing his junk to almost every girl in the hallway. Finally one of the girls knew him and called one of his friends describing the situation. Two of his friends then came and tried to wake him up but to no avail. They then had to carry Kyle's naked ass to his friends room where he remained til he woke up. Not only did he blow a certain hookup, but he exposed himself to all of his girl's friends and hallmates...

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Anon:

Art is kind of a maniacal guy, and following that trend decided to move to Las Vegas to further his career as a professional poker player. He doesn't play with sums like those guys on the Poker Tours but makes a good living off of it.

Art didn't know anyone in the area at all, and after a while started to get pretty sexually frustrated. After a few bad financial experiences with some of Vegas' finest call girls, he decided that he needed to meet some real women that he didn't have to pay. So he went to the Internet, eventually settling on (and paying for) "Adult Friend Finder."

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Oh, that's WAY more reliable.

He was having moderate success here, mostly meeting women in their late 30s (he was about 24) despite not being too thrilled with their profile photo-to-actual appearance ratio. Finally he is messaged by a girl that is his own age and by his own account much better looking than any of the other ones. She's Filipino (we'll call her Uno) and, in his words, had "very erotic pictures showing off her body." She lives real close to him and asks if he'd want to meet up with her and some friends later that night, which he agrees to without hesitation. He meets her, another Filipino girl (aka Dos) who he describes as being "even hotter" and a couple of guys that they are just friends with. After a few hours of drinking, the girls ask Art if he'd mind moving the party to a gay bar for the two male friends whom he now realizes are a couple. He doesn't see any harm in going to a gay bar with a couple of chicks, at least one of which he's sure he'll be banging later on.

After more drinking at the gay bar, Uno gets up to dance with the two gay guys and Dos stays with Art for more drinks. After a while, Art decides "fuck it, Dos is better looking" and starts fooling around with her. Eventually Uno comes back from the dance floor and asks Art if he wants to go back to her place. Art figures he came out to see Uno, so it would be disrespectful to ditch her for Dos, so they head out together.

In the car ride back, Uno starts making out with Art as he drives. She starts whispering into his ear "Are you ready to fuck my ass? I'm going to suck your cock and then put it in my ass." She then starts to give him road head for a few minutes until arriving at her place. As they exit the car, his libido running wild, she drops a question on him.

"Have you ever been with a Chinese before?"

"Chinese? I thought your profile said you were Filipino."

"Not Chinese, Tranny."

That's right. Uno and Dos were both Filipino males. Art then goes on to talk with Uno, trying to make her (him?) feel better about him no longer wanting to fuck. Art is probably also trying to make himself feel better about getting his dick sucked by a cross dressing dude. When he gets back to his place he checks Uno's profile and notices that it does indicate (s)he is transsexual, which he obviously made no attempt to look for earlier. He texts her apologizing again, to which (s)he replies "I bet you'll never forget this night!"

Art still lives in Vegas.

So when you go swinging online, make sure to read the Terms of Ass Use.

David:

Mid-Eighties. I am 23, just out of the service and finally back home, Atlanta. A friend from high school gets me a job at his fathers' small business running the warehouse. His father takes a liking to my work, and upon finding out I'm taking the bus to work everyday, offers to let me use the company van to commute to and from work with.

On a Friday afternoon a few of us from work decide to hit a bar that night. I should note here that I am gay. We hit a bar on Memorial drive. We drank until closing, 1230 am back then, and went our separate ways. I was driving the company van. Instead of heading home I have the bright idea of heading to a gay bar in Midtown that I knew was open after hours. I walk in and soon see the most beautiful transvestite I have ever laid eyes on. Beautiful face, delicious body, blond hair to her waist. From the moment I saw him I wanted him.

After who knows how many drinks we head to his apartment nearby. I don't really remember much that happened before sunrise but I do know that when I awoke with the sun in the window I was alone. Just me in the bed. I instinctively reached for my pants. Keys gone. Wallet empty of cash. My worst nightmare. I pants up and run to the den and his roommate is sitting there. I run by him, out the door, to the parking lot. Van gone.

I run back in and tell his roommate he took my van, my cash, WTF? "He's a cokewhore, he'll be back soon", he says. I think, what do I do? I wait. I alternate sitting on the curb of the apartment parking lot, pacing the sidewalks, wondering where this transvestite cokewhore took my boss' van, if he'd been stopped and arrested, sold it for a 100 bucks, or would ever return. Hour after hour of this nightmare continued, and the only funny thing I remember about this day is thinking I really need to be home by 3:30 for the kickoff of Miami-FSU.

Finally, about 2:30 that afternoon, I'm sitting in the den of the apartment, and he walks in. I run to him at the door, scream, "Where are the keys! You almost ruined my life!". He gave me the keys. I ran past him, down to the van, drove home and was sitting in my lazy-boy at 3:30. Miami-FSU kickoff.

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So remember, make sure your tranny is NOT a cokewhore before diving in.

Ben:

My friend, let's call him Jake, spends a lot of time at a local watering hole, as do the rest of us. During the NFL season, it's a very popular place.. There is always this one lady in a Roethlisberger jersey, lets call her Jill, that always walks around and shit talks anyone wearing anything but Steeler colors. So after a spending a few seasons frequenting the same Bar, Jake knows Jill pretty well, but they've never had interaction outside the bar.

Well Jake spots Jill at a work conference and they get to talking. Jill invites Jake over to help her "build her new grill, and a few drinks" at her new house. Now Jake's a nice young man who enjoys cooked meats and booze, and combined with an attractive, single lady, this opportunity could not be passed up.

Once the grill is constructed, and a few wine bottles have been consumed, Jake decides that he is unable to drive himself home. BADDABING! Jill is down for a party as well, but they're out of wine so they go to the liquor store and get some more. Now there is one little detail that I've left out on purpose, and that's Jill's 11 year old son. This would usually freak a guy looking to get laid out, but Jake isn't really like that. Apparently the kid is cool and they played some video games together while Jill watched real house wives of NJ or something.

By now it's getting late and Jill wants to watch a movie. Since Jill's new house isn't completely furnished, they decide to watch the movie in Jill's son's room. Jake and Jill on the bed, Little man down on the floor.

Jill has a stiff neck, Jake is "great at massages." One thing leads to another and Jake and Jill are fooling around on little Jill Jr.'s 11-year-old kid bed. I guess things were getting pretty hot and heavy cause the son woke up, and saw his Mom fooling around with Jake in his bed. That would piss any 6th grader off, so he storms out of the room. Of course, that's where the good stuff ends, because Jill had to go console her son. Now I don't know which would be worse, getting caught jerking it in the bathroom by your mom, or waking up to your mom jerking Jake off on top of your bed, but that's neither here, nor there. The story ends with Jake waking up in the kids bed, and Jill with her son leaving to go run errands. They have yet to finish what they started.

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And that young man grew up to be…. you guessed it… a tranny.

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