WLU Sex Archives: Segment 5: The Most Cringe Worthy

Stories have been edited for length, grammar and clarity.

My roommate and I lived in a really crappy apartment in third year. We threw a party and each invited our respective friend groups. What I had forgotten was that my high school friend and her 16-year-old brother were coming to tour the school, and had planned to stay the night. A few hours later, her brother was passed out in my room on an air mattress and I, in my drunken state, brought a guy from the party into my bed. My high school friend, wanting to spare her brother, came and laid next to us thinking this would be a good cock-block, but she didn't deter us. I had sex in my bed while my friend was lying next to us and her brother was asleep a couple of feet away. To top it all off, because she was blocking my bedside table, we didn't end up using any protection, so as I gave her brother a tour around campus the next morning she kept dropping hints about how reckless university students can be.

It wasn't that the sex that was bad, the sex was actually pretty decent, BUT I didn't get home from his place till 5:30am, when I realized my keys were nowhere to be found. None of my roommates woke up when I tried calling them to let me in. I was forced to try and keep myself alive in the hallway outside our apartment for HOURS until one of them woke up and checked their phone. I also thought I left them at his place so I made him check his entire house only to finally see them sitting right in the middle of the counter when one of my roommate finally let me in... FML. Seriously it was the walk (Uber) of shame (fame) from hell!

 

I was fooling around with a guy (who at the time was my boyfriend), when he started kneading my boobs like he was making bread and whispering weird things in my ear. Already uncomfortable, but not wanting to spoil the ‘mood’ I went along with it. He then starts to tap my crotch (keep in mind I was fully clothed, wearing jeans) as though he's playing an arcade game that he's about to win, while rubbing his naughty bits against my leg like a dog. Confused, I just laid there as he kept tapping my crotch slightly harder and faster in rhythm with his weird humping movements. Finally, I hear him groan and roll over. Not only did he "finish" from this, he leans over and ‘seductively’ asks, "did you orgasm?" BOI BYE.

I had been hooking up with this guy for a couple of months and he had been showing signs of being a total fuck boy. We had had sex one night, and were laying there naked when he oh-so-casually starts talking about how he really wanted to sleep with one of our mutual friends, and he was so happy I was such a bud that we could talk about this stuff. He was lucky I didn't castrate him right there.

I had been dating a guy in high school for almost a year at this point .... we were both really reserved and decided we were going to try oral for the first time. His parents were really strict so I had to pick him up at the mall, which is a good few kilometres from his house. It was like 30 degrees and he thought it was be smart to wear a sweater and black jeans. When he got to my house he was sweating so badly! When he pulled his pants down the smelled of BO was absolutely killer, and just I started gagging. It was so awkward. I didn't want to be mean so I sprayed his dick with Justin Bieber perfume and basically just couldn't breathe through my nose for the rest of the session.

 

 

When I was in high school, I was giving a blowjob to my boyfriend and I got a nose bleed. It was dark, so I thought my nose was just running, until his penis and everything else was covered in blood. To make things worse, it completely ruined his favourite white shirt. We laughed it off, but I will never forget it.

It all started one dark night at Phil’s (we already know this will be good), when the guy I had been hooking up with all night asked if he could come home with me. Me, in my drunken state of mind, thought that it would only be fair if I also brought a man home for one of my single roommates. The guy I was with took this challenge, and texted his friend to come meet us back at my apartment. By the time my guy and I had walked from Phil’s to my apartment (literally less than a 5 minute walk) the guy that would be set up with my friend was ALREADY STANDING AT THE DOOR OF OUR APARTMENT. How's that for hand-delivering a man? Flash forward a few hours, and post-romp, the guy I was with (who was twice my size) fell asleep on top of me, and started snoring. I decided that I could not bear to sleep like that, so I ran into my other roommate's bedroom, fully naked, and passed out beside her. In the morning, the man in my bed was gone and so was the other man that I had "ordered" for my roommate. What we noticed in the morning was blood SMEARED across the wall in our hallway, on the shirt I was wearing at Phil’s the night before, and in my friend's bed. We have yet to figure out where that came from, but we call it our Blood Bath of 2016.

It was my second sexual encounter with this person and we were at a hotel. Quick disclaimer - I was very very VERY drunk at the time but it was totally consensual. We arrived at the hotel and I thought it would be funny to run ahead and hide around a corner to "surprise" my lover to be. As I'm giggling to myself I hear him say "What are you doing?" and look to my right and see that the "corner" I was hiding around was actually an island of a wall. Already cringe-worthy. Once we get to the hotel room we decide that taking a shower together would be a GREAT idea. It had been a long day so we were both hot and sweaty, and what's sexier than a steamy shower together? WELL LET ME TELL YOU it can all go very wrong very quickly. I, for some stupid reason, decided that standing on the sides of the tub was a good idea - angles are everything after all - but much to my dismay, the sides of the tub were not quite wide enough for my feet. In one swift motion one leg slid down the inside of the tub, the other slid down the outside of the tub and all of my weight was thrown off balance, resulting in me hitting the lever on the toilet and a rush of cold water shooting down from the shower at my man who shrieked as he just stood in awe of me stuck between the bathtub and toilet. It was awful, I had a bruised ego and bruised legs for DAYS. Ugh.

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