During the winter quarter of my senior year, my fraternity was ordered by our national council to visit an interest group in Chicago. Our mission was to inspire confidence in these young men, that chartering a chapter of our fraternity at their college was a sound decision. We were to give them a 30 minute presentation, a meet and greet, and a Q&A to wrap it all up. However, the real goal of this trip was to establish good relations with a couple of the sororities on the campus. God bless our national chapter. We were to mix with the first sorority on Friday night, and the second on Saturday night. Looks like we had some solid weekend plans.
We scoped out the sororities online, and determined that the Saturday night girls were much better than the Friday night girls. We set our expectations accordingly. So I end up going out the Thursday night before the trip and partying heavily into the night. This includes a big late night munch courtesy of Rally's (you gotta eat). I wake up in a daze on Friday morning by my bro, who says that we're ready to take off. I pack my stuff and stumble into the car. We had a 6 hour drive to Chicago, so we pack some bowls and get comfy. We stop about 3-4 times for food to satisfy our hunger. We're chowing down on some of the worst that the road has to offer — onion rings, double bacon cheeseburgers, chili cheese fries, you name it. We get to our destination after about 9 hours of driving. We are already running late for the first mixer. This means that there's no time to get ready for the night.
We drop our stuff off in the hotel and rush to the restaurant where the mixer was taking place. We are the last ones there. We are pleasantly surprised because the overall aesthetic value of the sorority was MUCH higher than our online search had revealed. Coupled with our already low expectations, this raised our moods for the night. My closest bros and I are on fire this night. We're spitting some A game, and have all the girls lighting up. One particular girl catches my eye. Let's call her Whiskey. She's definitely one of the more attractive ones. She was a senior, so she was more mature than the younger sisters. She also works at the restaurant, so we are getting a great deal on food and drink. I focus all of my game on her. I give her the George Clooney charm between rounds of shots and fried appetizers for the table. My stomach is really full by this point. It doesn't matter, because we leave around 1am to go hang out at the hotel room. There's about 30 of us total in the room and we're getting rowdy. That means back to back shots.
I go outside with Whiskey, and we begin to flirt hardcore. At one point, she says, “okay, i'm tired, I guess i'm going to go home now. By myself.” Don't need to be any more clear on that one. I grab the keys to my bro's car and offer her a ride home. Once back at her place, she proceeds to change right in front of me. She's flashed me the goods, which means I'm as good as in. I notice she has a bunch of books on Hitler on her shelf. When questioned on this, she said she admires him. I took this as a sign that she was batshit crazy, but also probably a sexual deviant. She pushed me onto the bed and lays down next to me. You can imagine what's supposed to come next… HOWEVER, there is one glaring problem: There is a raging bull of a turd pushing against my sphincter, fighting for freedom. Between the Thursday night 4th meal, road food, and fried appetizers at the restaurant, i'm nursing a 6 lb. shit baby, and it was ready for delivery. I am struggling with all of my might to hold it in. She hints that she wants the D, but I can't give it to her, less I risk spewing this behemoth waste product all over her bed. So we lay in her bed and flirt all night. Every time she goes to the bathroom, I rush to her closet, and drop a heinous eye burner fart into there, to alleviate some of the pressure. She finally passes out around 8am, at which point I sneak out, back to the hotel room. When I get there, I drop a 2 footer, and clog the toilet. It was the best feeling of my life. I pass out, only to be awoken at 10am to meet the interest.
We do the deed, and mix with the Saturday night girls, who ended up sucking. What a reversal. Anyways, I got Whiskey's number, so we flirt over calls and texts for the next few weeks. She decides to visit me one weekend, to which I oblige. She stays with me, and we make up for that night of non-sex. She was indeed a freak as I originally predicted. Oh, and the reason that she was so into me? She says that because I was such a gentlemen and didn't try to have sex with her on that first night, she ended up falling for me…
I wish you could have seen her face when she opened her closet the next day. The shock of a belated dutch oven is always very gratifying. NEXT!
So last St. Paddy's day in Southie (the St. Paddy's day capital of America)I decided to invite some friends over to my place, since I live on the Parade route. Well my 'couple of friends' turned into about 50 other randos, and one who happened to be an amazing looking little Asian broad. As the night went on and we got increasingly shithoused, we started having boxing matches in my kitchen. After my bought this little Asian princess, who I hadn't really talked to all night, decided I did a good enough job in the kitchen/ring that she'd get into a make out sesh with me.
The night went on, more shit was broken, and eventually everyone was gone except her and I… and a few of my dipshit buddies who passed out on the living room floor.
So we get into my room, and within a minute we're ass naked and I'm pounding away. A little while into the slugfest she says, “You have a truck ouside right?” Obviously bitch, I'm a man. So she goes “I want to get fucking slammed in your truck.” I thought to myself, this broad is just hot enough that I'll risk getting hit with a public indecency charge, so we throw on some sweats and head out. We jump in the back seat of my truck and she starts riding me like I'm a fucking carousel at an amusement park. This girl was legit up for anything, deepthroating, fingers in de old butt (mine or hers, didn't matter to her), her only request was that I “slap her ass til it hurt to sit down.” Anyway, we finish things up and have the awkward wake up the next morning, neither of us knowing names, throw around a high 5 and she hits the old dusty trail.
We ended up having a few more months of sending nudies around after the one night stand, and we got another few rounds in when she had to fly out for Boston on a business trip, but I can say with full confidence that it was the weirdest/most fun one night stand of my career. The broad kept it real classy. “SHE WAS MY FIRST ASAIN!”
Submit your Hook Up Heroes stories here.
[Couple enjoying a dutch oven image via ShutterStock]