GREAT MOMENTS IN DRUNKEN HOOKUP FAILURE: Hooker Edition!

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

Hookers. You would think dealing with them would be a relatively simple affair. You call. You pay your money. You do your business. Transaction over. But never underestimate a man's ability to screw up virtually anything hookup related. Like in our first story, which comes from a seasoned "escort hobbyist," as he calls himself.

Sam:

I was on a work-based road trip, this time to Jefferson City. Like that of many states, Jefferson City was selected as the site for the capital for its geographical centeredness, and not for any redeeming value whatsoever of the city itself as a center of commerce or culture. However, where there are politicians and lobbyists, both of whom are far from home, there will be escorts.

The trip had been in the works for a while, and I had already planned well in advance with whom I wanted to spend a portion of the evening. One thing about escorts, though, is you don't have any way of knowing most of the time who has been arrested, or decided to "retire," or go on vacation. The only way to really monitor that is to keep up on the ads. I was a little concerned because my chosen companion had shut down advertising in the weeks leading up to my trip, and I didn't really have an attractive backup plan.

The day before I left, however, she was back. So I was set. I made the call immediately after checking in to the hotel in the early afternoon, for a pre-dinnertime appointment. Given the work that these ladies perform, and the hours during which it is often conducted, I have a strong preference for late afternoon appointments. Ideally, I am getting them after they have had a decent amount of rest. And even more ideally, I will be her first appointment of the day. Quality escorts don't overschedule themselves—three, maybe four appointments a day, at most. Still, you've got to believe that there is a difference in enthusiasm and energy level between No. 1 and No. 4. This is another lesson: if a girl is advertising 30-minute, or God forbid, 15-minute specials, STAY AWAY.

Noted.

She shows up at the appointed time, and we do the verifications, and get to talking, and negotiating what is going to go down. I lay out my plan.

"Sure," she says. "But you'll have to be gentle. You're my first since the baby."

"Oh, you just had a baby?"

"Yep. My doctor just cleared me for sex this morning."

Crash. I know I can't do it. It probably sounds really bizarre to have anything resembling morals in these situations. And it probably is. But I can't be, I'm not going to be, the guy who busts her postpartum cherry. I settle for a hanj, and pay for the full freight anyway. Hey, the kid needs diapers.

This was just one of the stories Sam sent me. Sam sees LOTS of hookers. And really, who the hell is HE to be so picky at that juncture? Back to the drunkies!

TJR:

A couple years ago I make the decision to stop renting shitty apartments with roommates and start renting shitty houses by myself. I found myself a two-bedroom house with an in-ground pool and separate hot tub next to it. So, I decide to throw myself a housewarming/no-more-roommates party. My best friend's wife tells me that she's bringing her friend from work, who we will call Rachel from here on out. I'd met Rachel a few times before and found her to be very attractive. Apparently she was into me as well, but the timing had never been right before tonight.

The party is going well and I'm chatting up Rachel almost the entire night, hoping to get her upstairs to christen my new bedroom. About 1 AM the party is winding down and almost everyone has either left or pass out, save me and Rachel. Then she says that she brought her suit and we should get into the hot tub. Now, I've never been a fan of hot tubs and never had any plans of using it (it was one of the reasons I almost didn't rent the house to begin with), but at this point I'm drunk, horny and willing to do just about anything she suggests. So we change and get it, but it's only a matter of time before we're drunkenly making out and the suits come off. Then she has me sit on the edge of the tub and proceeds to give me some of the better eye-rolling back, toe-curling head I have ever received. When I am dangerously close to finishing she declares that it is time I return the favor. I wish she had waited another minute to make this decision, but whatever.

At this point she asks if we can try something she saw in a porno. While internally I'm thanking God for finally rewarding me after all those years of dating women whose idea of kinky sex was leaving the lights on, on the outside I say something drunkenly stupid like, "Why yes, yes we can."

She wants me to go down on her while she's floating on the water, which doesn't sound possible to me, but I'm willing to try it. The hot tub is one of those standard issue ones you see in hotels: about eight feet across and has a built-in benches going all the way. Basically, she will brace her feet on one edge, put the back of her knees on my shoulders and then brace her hands against the bench in a sort of crab-walk position. Why she wanted to try this I will never know, because it did not sound comfortable.

Anyways, I'm down there, doing what I do well and she's rocking her hips. The only thing is with each rock she's getting more and more into it and bringing me closer and closer to the water. As she was getting close to cumming she takes her hips back a little too far and in my attempt to keep my tongue in contact with her clit I go under the surface and water shoots up my nose. I start to cough and recoil, but she really wants me to finish her off, so she takes one hand and starts to bring it around to pull my face back in. Only between how close she was to orgasm and how many beers she had had during the party, her balance is pretty much gone and she starts to tip over, at which point her head slams right onto the edge of the hot tub and open a two-inch gash over her eye.

These are the kinds of cuts that bleed a ton and within a couple seconds the hot tub water is turning red. I will say this though: sitting in what is literally a pool of blood sobers you up quickly. I find my bathing suit, her bathing suit and my keys in about two minutes, then toss her into my car even as she's bleeding through her towel. Now, I don't know if you've ever brought a woman to an emergency room with what appears to be a violent injury, but it is not fun. At least three cops come around to ask her if I got drunk and hit her. Several hours later she gets released with a possible concussion and a nice large cut over her eye she will have to explain at work for the next couple of weeks. I get to go home to drain and then scrub the hot tub that I never wanted to use in the first place. This is why porn positions should be left to the professionals.

Indeed they should. At least you didn't drown, though. I totally thought your were about to be drowned by a vagina. Not a bad way to go.

Mike:

This past year was my freshman year at the University of Delaware. One night early in the fall semester, one of my friends Joe from high school came over to my room to pregame before we ventured out to find a party. It was just the two of us because my roommate was staying in to watch a movie with his girlfriend (now ex), and we didn't know many other people on the campus. So the entire pregame consisted of us doing shots of Peach Burnett's and watching the Phillies.

We started taking more and more shots as it got later. This is how it would go..."Joe! Take another shot!" "Naa man. I'm good." "Really? This handle of Burnett's just called you a bitch!"

I don't think peach vodka is allowed to call ANYONE a bitch.

So we would do more shots. Eventually we got pretty hammered and we had heard about a party on N. Chapel St., so we made the walk there.

Since this was before rush week, it wasn't that hard for two freshman guys to get into the party. We got some beer from the keg and started hanging out. Before I knew it, I was absolutely hammered and Joe was nowhere in sight. I sat down on the couch to relax for a second and as it turns out, a girl was sitting next to me. The next thing I remember is us hooking up on the couch, and then us standing up and hooking up, with no memory of anything in between.

At this point, I thought the night was going awesome. I thought this was the first chance I was be able to bring a girl back to my DORM ROOM! It was something I always dreamed of. But the Peach Burnett's and Natty Light had other plans. As we were making out, I started to feel it. Even with my eyes closed, I could feel the room spinning. I held on for another second, but I never stood a chance. I broke the kiss and fell flat on my ass. I heard some people laughing and variations of "What an idiot!!"

I didn't know what to do. As I look up, I see my friend Joe on the couch, who has no idea what's going on, and I see the girl, still standing there with her face in her hands. I guess she was embarrassed. I got up and shook it off. I kept saying, "Somebody pushed me! Who would do that?"

Either she was just as drunk as I was, or I'm very charming because we start making out for another second. But it happened again. Fell flat on my ass. She didn't believe me that somebody would push me twice, so she walked away and I never saw her again.

The fact that you randomly fell instead of puking is what makes it so charming.

Colin:

My friend Dan had a huge crush on this girl, but couldn't work up the courage to ask her on a date. After months of nerves and sexual tension, he finally worked up the courage. She said yes and he was ecstatic. He planned out this dinner at a nice restaurant just a short train ride from South Bend, made reservations, the whole deal.

The date night comes around and the two walk to the station. The kid really needed to fart but he's tried like hell to hold it in. Try as he might to clench and do the stilt walk, Dan finally reached his breaking point and tried to apply the silencer. He managed to silence it. Unfortunately, what he failed to prevent was a Class A shart that not even his briefs could contain.

Keeping a cool head, the Dan told the girl that he just remembered his brother's b-day was in a few days and he needed to pick up a shirt for him at the nearby Banana Republic. The girl agreed to let him do that.

Inside the store, he grabbed a shirt and a pair of pants. Dan told her that his brother and him wore the same sizes and he bowed into the dressing room to try on the clothes. Seeing that the pants fit, he went to the register quickly while the girl was looking at clothes, bought the shirt and pants. Immediately, he told the lady at the register that he changed his mind and only wanted the pants. She said that it was okay, made the exchange, and handed him the bag. He quickly took it, found the girl, and they continued to head to the train.

They caught the train, with his original stank pants still on, and they headed off on the train. After a few minutes, he told her that he needed to go to the bathroom. He took the bag with him. Immediately, he locked the door to the room and rips off his literally destroyed pants/undies. He throws open the train and throws them out.

He opened the Banana Republic bag to pull out his fresh pair and he finds… the shirt. Folded up with tags and all. He frantically looked under it to find nothing but the empty bottom of the bag.

Dan waited for the train to reach its next stop. With no other alternative, he wrapped the shirt around his naked lower body, gets off the train, and hopped into town in search of a retail store. Meanwhile the girl continued on the saddest train ride ever alone. Never talks to her again. Girl of his dreams. How about that for shit luck.

Yeah, but that's what you get for asking someone on an actual DATE in college, and needing to take a goddamn train to where you're going.

(Ed. note: Come on, Drew — snopes.)