Regrets are overrated, but awkwardness is real

Occasionally, I get it into my head that “something” will be a good idea. That “something” could be anything  —  getting my nipples pierced, going ice-skating, asking a near stranger out to coffee  —  but I usually end up being wrong. In fact, I would go so far as to call most of my spontaneous blunders bad ideas.

And one of those “somethings” happened one evening over the summer following my senior year of high school, when I became very bored. Boredom and I do not get along. It is in the throes of ennui that I’ve conceived the majority of my “good ideas”, and that night was no exception. I was struck with an epiphany.

“I should have sex with a boy,” I thought to myself. “I should have sex with Landon. This is a good idea.”

Let me take a moment to clear the air: I am a lesbian. I was a lesbian then, too. This evening was not a lapse in my sexuality but rather a brief fit of insanity. I have no excuses.

I had only met Landon once, when my friend, Lex, dragged me to his apartment about a week prior to my bright idea. Our first meeting had ended in a fantastic back rub and in yours truly cramming his iPad full of inane games and pointless apps.

So why Landon, out of all the boys I knew? For one, the majority of my male friends were homosexual. I also didn’t want to sleep with someone I knew particularly well and thus confound our platonic relationship. Aside from that, I’d been impressed by Landon’s skills as an impromptu masseuse, and he wasn’t that unattractive  —  for a boy. He had no scratchy facial hair or beer gut or empty cans of Red Bull littering the floor of his room. His carpet even seemed to be recently vacuumed. In the end, I had sex with Landon because he gave decent back rubs and had a clean apartment. I obviously have good priorities.

I was in the car with Lex when I had my profound revelation. I informed her of my burgeoning plan, and she immediately whipped out her cell phone to dial Landon’s number. When she relayed my intentions to him, he expressed firm disbelief, probably due to the fact that  I’m a lesbian. She coerced him into inviting us over anyway.

Upon arrival at his decently neat apartment, Lex and I spent a few awkward minutes socializing with Landon and his roommate, but before long, Landon pulled out his iPad in exchange for another back massage. Of course I agreed. Not only could a back rub lead to further intimacy, but I also got to screw around with his expensive electronics.  With the iPad propped up in front of me and my head cradled in the crook of one arm, he went to work.

After a few minutes, Landon leaned down and asked, “Can I pull your shirt up?” I didn’t need convincing. He tugged up the hem of my blouse until the flat plane of my back was bared, as well as a little bit of side-boob. He continued his Herculean effort, dragging callused palms down ridged vertebrae and rubbing circles into my shoulder blades. Let me tell you, there is little better than dedicated hands on a sore spine.

Finally, he seemed convinced. He bent close again, this time with a request, “Come up to my room?” And that’s how, ten minutes later, I found myself shirtless and thoroughly doubting my decisions in a strange boy’s neatly made bed.

Honestly, it wasn’t that horrible of an experience. The poor boy pulled out all the stops. He went down on me —  which was my first experience with oral sex  —  introduced me to the beauty that is biting and scratching, and even used a vibrator on me before he moved in for the kill. Objectively, he did a respectable job, but without that key sexual attraction, it all just felt awkward and distinctly wrong.

As such, a certain biological process was lacking without that same attraction: lubrication. I’m so sorry for those who can sympathize with me; being penetrated without being wet or using lube is like being split apart.

He thrust into me for at least five minutes with no sign of stopping. I was detachedly impressed; he had significantly more stamina, it seemed, than boys in the stories that my friends told. However, my vagina couldn’t keep up with him, and after a particularly agonizing thrust, I asked him to stop. He promptly rolled off of me and asked if I was okay. I confirmed that I was, and he scooted away for a few moments to presumably remove his condom. I couldn’t see his actions very well in the dark, or even really see his dick. At least I preserved my eyesight, if not my virginity.

Afterward, Landon tried to cuddle. Bless that boy. I left him with blue balls and deprived him of my excellent cuddling skills. Instead, I quickly dressed, bid him farewell, and dragged Lex out of the apartment to drive me home.

Needless to say, that final part of sex  — what some might call the act of sex —  was extremely unpleasant. I got home later that night, aching and wincing every time my thighs brushed together, and I scrubbed myself in the shower until I could no longer smell him on me. Then I ran a bath to soak my sore lady bits. The water stung. The realization that my good idea was not a good idea stung even more.

I regretted my actions for months afterward. I avoided Landon and kept tight-lipped about the whole shindig. However, now that I have the benefit of hindsight, I’m glad I went through with it. It was a valuable life experience, if not a particularly exciting one, and it left me with a hilarious story. Regrets are overrated, anyway.

Kalyn H is a Behind Closed Door columnist and likes to try new things. 



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