XIII. The Guy Who Was Into Roleplay

“You’ll think you just graduated magnum cum loudly”

– Cecily Strong –

I have always been weirded out by the idea of roleplaying in bed. First of all, how do you bring up the topic to your sexual partner(s) without sounding like a creepy sex addict? “Hey, do you wanna pretend to be my step-dad and fuck me? Don’t worry, I obviously have zero daddy issue!(I got goosebumps just from typing this). I can’t even begin to understand how porn stars can say those cringy dialogues without contemplating their life decisions that led them to star in a Pokémon Go inspired gay porno (appropriately titled Fuckémon Go). However, I have to admit that a few of those sexual fantasies intrigue me (I won’t mention them because some of you shady bitches are super judgmental) and I won’t mind trying them out at least once. But I will tell you this. I’m definitely not into any incest-related roleplay; it creeps the fuck out of me.

To be perfectly honest, I did not know what I was thinking when I agreed to invite this guy over to my place. Have you had one of those moments when you don’t want something to happen but the other person somehow manages to psychologically trick you (commonly used technique: guilt trip) into wanting to do the exact thing you refused doing five minutes earlier? This was one of those moments. He’s not exactly my type: he’s a bald Caucasian guy in his late 30s with thick facial hair. I really don’t know why but bald guys don’t really do it for me. I mean… please make up your mind. If you want to have zero hair on your head, don’t have hair anywhere else on your face except for your eyebrows and eyelashes (ok, a short beard is acceptable but it has to be proportional and aesthetically pleasing). Our conversation went like this:

“So you go to school around here?” he asked after sending me a few dick pics (who says romance is dead?)

“Yeah, my school is 10 minutes away from my place”, I hesitantly replied.

Out of nowhere, he asked me, “Are you into roleplaying?”

At the time, I didn’t know what roleplaying was. In retrospect, it’s kinda obvious what it meant but I thought it’s just about taking turns playing the role of a top and a bottom. You don’t know what tops and bottoms are? I’ll teach you with the help of the visual below; basically, the guy with the banana is a top and the guy with the Nutella jar is a bottom. I apologize in advance for the slightly graphic visual lol.


I didn’t really know what I got myself into but it sounded like a fun idea at the moment, so I just went along with it. After a minute long discussion, we came to the agreement that we were going to roleplay as a professor and student, since I was still, in fact, a college student. In my mind, that was the least creepy and age-appropriate option for our roleplaying session. You can blame PornHub for my sickening fantasy, and I’m not talking about the empowering “yass gurl, you look sickening!” interpretation of the word sickening. We didn’t really talk about the background of the story (because honestly, who watches porn for the coherence and legitimacy of the storyline?), but I imagined it was centered around a college student trying to gain extra credits for his Human Anatomy assignment and his professor tried to help him by giving him “extracurricular activities” so his student could graduate.

tenor (2)

To say that the sex was an awkward mess is a HUGE understatement. I guess the only good thing about the sex is how we kept one fact to be super realistic: 99.98% of my professors in college did not sexually attract me. He’s by no means hideous, but he’s definitely not my type (ok… he might be my type after four tequila shots?). Now, I apologize in advance if I’m offending anyone with this, but I have one thing I need to confess: hairy back grosses the fuck out of me, and I’m talking about fully-grown back hair that makes a guy looks like an ape from behind.  Just. Eww. Gross. Again, to my readers who are feeling very attacked by my strong hatred for hairy backs, I’m sorry. You are still beautiful and I’m sure there is someone out there who finds your hairy back attractive, but unfortunately, it won’t be me.

At some points during our “extracurricular” activity, he whispered to me the following questionable statements:

  • “You really want to get an A, huh?”
  • “Do you like your professor’s dick?” 
  • “You’re definitely getting an A for your assignment”

I couldn’t help to chuckle when he quietly whispered the above sentences to me on my tiny-sized bed. I honestly don’t know how I could facilitate the manifestation of the “forbidden student-teacher affair” fantasy better, but my boner had never disappeared faster when he said those things to me passionately. Fortunately, I am a fairly decent actor with a mislaid moral compass, so I decided to channel my inner ambitious high school student persona and finished my “extracurricular activity” with no complains. At the moment, I finally realized how and why most women fake their orgasm when they are clearly not enjoying the sex, because most men are egotistical human beings who are raised in an era of toxic masculinity. Seriously though, how could he be so oblivious to the fact that I didn’t look like I was enjoying the sex?

We said our goodbyes to each other after we were done with our “office hour”, and I immediately blocked him on Grindr right after I closed my apartment door. Idk, I guess I was traumatized? But at that moment, I solemnly swore to myself that I wouldn’t try roleplaying ever again. Well… unless it’s Matt Bomer and he wants to reenact his Magic Mike scenes with me. I mean, who am I to say no to Matt Bomer?

2 thoughts on “XIII. The Guy Who Was Into Roleplay

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