Babysitter Hook-Ups, a Girl Pretending to Die, and Urine Coming Out at the Wrong Time

by 6 years ago

This first one involves a babysitter. More commentary to follow. 

When I was 16, and a junior in high school, I threw a small party when my parents left town. All goes well but my friend left a beer can in my parents' room. I get in trouble, yelled at, the normal routine.

A couple weeks go by and my parents are going out of town. Not trusting me at this point, they call me a babysitter. A F*CKING BABYSITTER. I'm mad for obvious reasons. I was on friendly terms with this 22-year-old babysitter but I knew she was very religious and the odds of a party are small.

The next day I text her innocently asking if I can have a couple friends over and we would be drinking. Much to my surprise, she says “yes.” I'm pumped. I call my boys and the next day they come over with a handle and dual 30s. We have a chill night of drinking beer, pong, and flip cup. Due to lack of planning it’s my 9 friends and I and one 22-year-old girl in college. After a couple hours we have been drinking too much. She starts trying to feed us Cheerios because she too is drunk as hell. Everyone’s drunk.

Next thing I know she’s pulling at me and asking me to go to my parents' room where she’s staying. I'm drunk and willing. My Bros are trying to get her attention after we get to my parents' room. I'm on the verge of passing out when she leaves the room to go downstairs. Nothing happens.

Thirty minutes later I wake up to her grinding on my passed out body. She wants it. I'm not turning it down so, I start hooking up with this chick on my parents' bed. She starts sucking me off. It’s pretty sloppy but I don’t care because I'm drunk as hell. She was positioned sideways, so naturally I take the opportunity to start fingering her. A few minutes later, her sloppy puss is dripping all over my hand. So I look down and I see red on my finger. I immediately ask “are you on your period!” She says “no” and I continue not thinking.

Well I look down at my finger 20 seconds later and I see blood EVERYWHERE. I freak the f*ck out. I start yelling at her for being on her period and getting blood on my parent’s bed. Then I ran outside the door with just my boxers on and my bloody hand held in the air. My Bros are laughing like crazy and the laughter becomes, “that is f*cking disgusting.” I wash my hands to the bone.

Proceed to go back up to the room with a bleach pen and throw it at her and yell “fix it!” I pass out around 4 a.m. disgusted. I wake up the next day around 2, all my bros are watching TV. I get reminded of the story and they all give me shit. She walks downstairs around 2:30 and if you think something is awkward think of this moment for me. My Bros get out of there faster than you can imagine. I tell her the house better be clean and I lock myself in my room the whole day until she leaves.

The worst part is whenever my friends become too drunk they bring up the time I got “raped” because she was 22 and I was 16 at the time. Oh, and since she was a family friend she came over Christmas dinner that year. I have not said a word to her since that infamous weekend.

Am I alone in thinking that sometimes you’ve got to run a few red lights in order to get where you’re going in life? You could have bagged a 22-year-old when you were only 16? I get that blood grosses some people out but you should approach random sex like it's football; you've got to play through the pain and you never call the game because of a little rain. NEXT.

This sob story doesn't even count as a hook-up but I couldn't NOT include it. 

It’s my freshmen year and my best friend and I go to a football game where he meets his girlfriend. She introduces me to one of her single friends (who was on the uglier side of the standard line, but I let it go).

So we started texting and all that other bullshit and I take her to see one of the “Twilight” movies. By “coincidence” two of her friends were there as well and they cock blocked the shit out of me after the movie. At the end of the night, I tried to lean in to give her a goodnight kiss, but the b*tch doesn't go for it.

A few days later a few of her friends texts me and tell me she died in a car crash. Needless to say, I was pretty sad for the next few days.

Well, I later find out from one of my other friends that she broke her cell phone and thought it would be funny as shit to pretend she died so she didn't have to tell me that she didn't like me. I would have been okay with her having one of her friends tell me she didn't like me to my face or through a text message, but to pull shit like that is unforgivable.

I'll leave it up to you, the readers, should I get her back for it, or should I let it be?

For the rest of this week's stories, click to page 2.


I wish this next tale ended differently. 

It all began during my first and only semester of college. Not knowing anyone at school I decided to pledge a fraternity. Every year there was a Halloween date party and, me being me, I waited till the last possible second to get a date. So I Facebook’d a girl from the floor above me (who I'd never met or spoken to before) and asked if she’d like to accompany me. To my surprise she was pumped and said she had a Victoria's Secret outfit she wanted to wear. Did I mention I had never talked to her before? A tried-and-true sl*t. 

So the party night arrives and I bring this 90-pound little girl wearing only lingerie. Well, I end up f*cking her on my fraternity brothers’ porch on the lake while they all listened and chanted (side note: she didn't even drink). After that we went back to her room, where she had no roommate so the beds were pushed together. Being that she was a freak I stayed there a few nights and railed her out again and again. This girl was certainly no keeper but she was definitely like a disposable razor: still good after one use.

Then one morning, while she was in the bathroom, I found over 30 prescriptions in one of her draws (probably why her roommate split) and I realized she was a lunatic. Yet, I still kept her around because she gave it to me whenever and she also fed me her loony pills.

A few weeks later, I'm plastered and in need of a nut so I called the “nympho,” as my frat brothers called her. She said “come up to my room when you get back.” Naturally I did just that but I skipped out on the bathroom (I had to piss like a race horse) because I knew I would last hours if I held it in. So we f*ck non-stop for 2 hours (literally, it hurt) when I finally am about to shoot my load in her. I flip her over doggy — like any real man would  — and blow a huge load, I c*m for 45 seconds. That’s when I realize I've NEVER came for 45 seconds before in my life. I take my dick out and see the condom is filled to the brim… WITH PISS. I didn’t know what to do, I just took a piss in this girl's vag*na so I tied it like a water balloon, threw it in her garbage, and run out with my clothes in hand saying I need to go to the bathroom. That was the last time I ever spoke to Nympho. To this day I still wonder if she found the piss-filled condom.

Side note: My roommate thought his dick was huge so I would steal his Magnums so I didn't have to pay for condoms. If it wasn't for the golden ticket, this loony would have gotten a golden shower…

Imagine the hilarity if he tied-off the piss balloon and spiked it off her face? Guy would be a living legend, like R. Kelly.

We've seen this next movie before. 

Back in high school I had just started dating this girl and one night we decided to sneak out and meet up. I picked her up in the Ram and we found a nice little cul-de-sac to indulge in a late-night session.

Her and I had hooked up before, but that consisted of just making out and a little b**bie touching. So naturally I was excited to see where the night was going to lead. We started hooking up and as things were getting hot I moved over to the passenger seat so she could start blowing me. This night was headed in the right direction. Until, about 30 seconds into sucking me off, she comes up and tells me she’s got to go home now.

I tried to get her to stay and finish the job but she insisted she has to leave and off she goes into the night leaving my balls blue. Driving home I'm trying to figure out what could have possibly happened that made her sketchily leave but can’t find any answers? I figured she was about shit herself or something.

When I got back to my house I was going to finish what she started and go to bed. But when I pulled down my pants to start stoking it what do I see? There, in my junk hair, was a nicely chewed piece of orbit gum.

After about 10 minutes of just trying to get a grip on the whole situation I give myself an unexpected haircut and call it a night. As much as the experience sucked, it made one hell of a story and hopefully taught her a valuable lesson.

In the event any ladies in the crowd failed to pick up on that “lesson” it’s SPIT OUT THE F*CKING GUM before you blow us. Our dicks taste like gym socks, deal with it.

Our final story is about the perils of finding lust on public transportation.

I go to a liberal arts college in Philadelphia and play lacrosse. Because of snow last year in March a Saturday lacrosse game was canceled and we got the weekend off for the first time since the season started in February. I decided that instead of spending the weekend at school and relaxing I would go visit some friends on Spring Break in NYC. I decided to take the MegaBus instead of Amtrak, possibly the best bad decision of my life.

My bus was supposed to leave at 9 p.m., but if you’ve ever taken the MegaBus you’d know it leaves no sooner than an hour after the expected departure time. So I’m waiting outside in the bus line and like I said before it’s snowing and f*cking freezing. I see this cute girl a couple of people in front of me in a skirt, pea coat, and a scarf obviously freezing her ass off. I can’t muster up the courage to talk to her so I keep standing in line, listening to music, and waiting for her to make eye contact with me so I can go up and talk to her. Well, an hour or so goes by and I don’t know what came over me — maybe the hypothermia setting in or I just got bored of being a p*ssy — and I finally went and talked to her. It turns out she was an aspiring actress that was in Philly for an audition or some shit like that. She was actually pretty nice too so I keep talking to her and asked if she wants a pair of pants to keep her warm. She takes the pants and we flirt until the bus comes and she asks if she can just sit next to me on the bus because she doesn’t want to strip in the cold Philly streets. I told her of course she can sit with me and I would rather have her strip for me than everyone else in line.

When we get to the city, she asks where I live. I told her the Upper West Side and she says she was actually going to visit a friend up there (it’s 2 a.m. so… pretty odd time to visit a friend) and asks if I want to split a cab. I obviously do this. When we pull up to my apartment and she asks if she can come up and pee. We are greeted by the doorman, she is thoroughly impressed. I take her up and give her the “grand tour,” she uses the bathroom and says she thinks she should go see her friend. I told her she should stay and have a glass of wine with me so I open up my parent’s cheapest bottle (I should mention that no one is in the apartment except me because my parents live in West Virginia and rarely use the NYC apartment). After half of a bottle, her panties hit the floor and we defile every room in the house.

I wake up the next morning and bus girl isn’t there. Naturally, I think she is paying me back for the best night of her life by getting breakfast for me. Well, 30 minutes go by and she still hasn’t come back so I go to my phone and look for her name… Not in the phone anymore. I FREAK OUT. I check the jewelry boxes, my wallet, the humidor, everything valuable to make sure that nothing was missing. Everything was in still there so I just got on with my life.

A few minutes later I called the friends that were in the city for Spring Break and met up with them for lunch. I had liked one of the girls in the group for most of high school but nothing even happened. I planned to change that this weekend, it was her birthday and I had the hook up at RdV for the night. I took them all out to dinner and then took the girl I liked out to get a birthday present. I bought her a book in Union Square and we walked around, things were going well.

As we walked out of Max Brenner’s for dessert I hear a familiar voice calling my name. I turn around and out of nowhere, Maura, the girl from the night before tackles me. I make the introduction between her and Megan, the girl I liked, and try to get Maura away. When Maura realizes that I want to get with Megan she pulls the b*tchiest cock blocking-est move ever. She says, “Sam is such a good guy, you don’t even know! It was amazing to get in his pants last night! He is just too generous.” Well, f*ck me Maura… she starts to leave and then tells me to call her sometime, knowing damn well that she deleted her number from my phone. I’m dumbfounded.

I try to tell Megan that I let her use my pants in the cold the night before but she wouldn’t hear it. My night ended with walking an angry girl back to her hotel and not going out to the clubs because I had no girls to bring to help get me in. Moral of the story, I am taking the f*cking Amtrak from now on.

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