My 3 Most Horrible (And Hilarious) Sexual Encounters

Here goes—my three worst sexual experiences to date. I’ve learned the hard way that sex can be good and bad. The important thing is to remember that the bad eventually becomes hilarious.

1. “I’m Not the Biggest Tool in the Shed”

St. Patrick’s Day is one of the rowdiest college drinking days in the entire year. My school was no exception. In addition to celebrating on March 17, the weekends before and after were nicknamed “St. Practice Day” by the fraternities. As a sophomore in college, I happened to love St. Patrick’s Day and its affiliated weekends because I could get free alcohol as an underage 19-year-old. In fact, much of my rebel child syndrome came throughout the years of 18-20. Most of March 17 is spent skipping classes and day drinking, but for some reason, I couldn’t get out of my class that year, so I resorted to becoming wasted around 7 PM. I had a huge crush on one of the guys who happened to be in our friends group and we ran into each other while waiting in line for a frat party.

As drunk friends often do, we decided it would be way more fun to trek all the way up back to his dorm on a bus and hang out just the two of us. When we got to his dorm room though, his roommate became the world’s best cock-block. Sigh. So we hiked it back down to my off-campus apartment and after securing the room away from my roommate, we got down to business. He immediately pulls his jeans down and says, “Sorry, I’m not the biggest tool in the shed.” I mean, to be honest, yeah, he wasn’t. BUT WHO LEADS OFF SEX THAT WAY? Way to get me in the mood, buddy. I tried to not to ignore it, but it was so small that it just kept popping out and eventually we had to call it quits. I ended up kicking him out just in time to catch the bus back to his dorm. We’re no longer friends on Facebook.

2. “That Time I Bled on the Guy Screwing Me”

Clearly, this was highly embarrassing at the time. I laugh about it to this day though. One of my best guy friends from high school was visiting me at college for the weekend during our junior year. We both used to have a thing for each other, but it was never the right time if you know what I mean. It always so happened that either one of us was involved with someone else or we were never in the same place. We were determined to have sex, though, especially since we both left high school only having fucked one person—we needed to see what tricks each had learned in three years. We started to make out, I gave him head, he fingered me, to say the foreplay was fantastic would be an understatement. Eventually, “Tom” put it inside me and began to thrust. He looks down only a few moments later and exclaims; “Oh crap, you’re bleeding.”

Normally, I’d be fine with a little blood, but this was gushing like a river. I continue to rack my brain to figure out how I bled so much (I was not a virgin), but it was everywhere—on his dick, on his fingers, staining my sheets. I ran to the bathroom in a T-shirt and underwear to attempt and clean myself up. After I mopped most of the blood up off my legs, the toilet began to overflow. Picture this: I’m banging on my roommate’s door to help me with the toilet half naked, after I started bleeding on a guy during sex. Tom decided to sleep downstairs after that and I do not blame him one bit. Apparently I became a legend in his fraternity house. Oddly enough, I’m proud of that.

3. “My Dad Walked in on Me”

Everyone has a story like this. I’d be disappointed if they didn’t. I got my first high school boyfriend in September of my senior year. It honestly made my last year of high school amazing. We also had a free lunch period, meaning we could go off campus to eat if we so wished. Thus, Mike and I used to bang each other on our lunch break instead of eating. I only lived a mile from the school and lunch was 45 minutes—perfect timing. I had AP Chem after lunch and would always walk in late, with my cheeks flushed and slightly disheveled. Could I be any more obvious? Both my parents worked full time, so Mike and I never ran into problems, until the day we did. My bed was a queen-size mattress from the 70s with a brass frame that squeaked like you might imagine in a porn movie.

Consequently, neither Mike nor I heard the garage door opening indicating my father was home for lunch. As he came up the steps, I threw Mike off me and jammed my legs through the first pajamas I could find looking like a complete fool when my dad opened the door. My dad immediately shut the door, knowing full well what was going on. Mike and I got dressed and sheepishly came downstairs, making small talk. Thank gosh my dad is pretty low key, so we agreed to never speak about it or tell my mother. The only person really hurt in all this was Mike, as he was in too much of a hurry to take off the condom while getting dressed and kept it on until we arrived back at school.