II. The Guy Who Took My Anal Virginity

“I believe it was the great American painter Bob Ross who said, ‘the key to a swollen vagina is… courage'”

– Katya Zamolodchikova –

I think by now, 98% of the human population understand that your anus is a one-way street. To this day, I still can’t understand how some people enjoy getting stuff shoved up their asshole. It’s a medical mystery. Sure, there is a scientific explanation on how anal sex can feel fucking fantastic (how our asshole has gazillion sensitive nerves blah blah blah). But think about it. To those of you who enjoy sticking your eggplant inside somebody else’s peach, when did you start staring at someone’s ass and thought “Aah… I’ll insert my disco stick in there and the world is gonna be a better place”?

I, on the other hand, have always been fascinated by the one on the receiving end of anal sex. I remember watching straight porn for the first time (yikes) and had always wondered how it would feel like to have a penis inside me. This boy right here is a natural bottom, I guess.

So when the opportunity presented itself to me (re: I got a message on Grindr), I took my chance. This Caucasian guy, who was in his early 30s, was relatively good-looking with a nice toned body. I know… you are probably thinking, “damn, this guy has a severe daddy issue!”. First of all, what are the symptoms of daddy issue anyway? And why do people make it sound like a bad thing?

He decided to invite me to his place to “hang out” (that’s code for “Let’s bang!”).  His place was 10 minutes walk away from my place, and my last remaining self-worth pretty much disintegrated at this point. But I was on a mission. I said to myself, “you’re NOT gonna die a virgin.”

Warning: from this point on, the story is gonna get waayyyy more explicit. Don’t say I didn’t warn you.

I walked into his room, and I was grateful that he looked exactly like his picture (thank God!). We didn’t really waste any time and went straight to his bedroom. I did appreciate that he already put his blanket on the floor. You know, to give us more space to perform our routine. He knew exactly what he’s doing, or in his case, who he’s doing.

Things got hot and heavy very fast. Next thing I know our clothes were already on his bedroom floor and we were left with our undies on. The 18 years old virgin sported an American Eagle neon green boxer brief, and the 30 something years old sexpert was rocking a Calvin Klein dark grey brief. If you saw us doing the deed, you could immediately tell which one of us was the virgin.

Once I took off his underwear, I was immediately awestruck. Ok, I am probably exaggerating a little bit here. His penis certainly won’t win any award, but hey, from what I remember, it was nicely shaped and proportionate. Keep in mind that this was the second time I got up close and personal with another guy’s dick. But once I saw his genitalia, I had a couple things in mind:

  • How the hell am I gonna fit this thing in my ass?
  • Should I run away now before he destroys my ass and needs to take me to the hospital?
  • Ah.. so this is how a circumcised white dick looks like.. very interesting
  • It does look like a snack lol.

Next thing I know, his penis was already in my mouth, and my penis was in his mouth. The term 69 finally made sense to me, because the circle on the number 6 represents… you know what I’m talking about here.

Suddenly he lifted my legs in the air to expose my asshole. Have you ever seen one of those Chinese restaurants where they hang roasted duck on the storefront? I looked exactly like one of those ducks, ready to be devoured. Out of nowhere, he started licking my ass without any prior notice. I got immediately grossed out and wanted to scream “Ewwwww”. Hadn’t he listened to Nicki Minaj’s “Truffle Butter”? (oh wait, the song hadn’t been around at the time). Did he even know what it meant? DO YOU EVEN KNOW WHAT IT MEANS? I mean, I did take a shower before coming to his place, and I made sure that the area around my asshole was relatively hygienic. But nothing prepared me for that moment.

But holy shit… did it feel good? Abso-fucking-lutely.

He turned me around and I laid on my belly. This is it. He could have grabbed a knife and stabbed me in the back, and I wouldn’t even know. Instead, he grabbed a bottle of lube and started to generously apply some lube on my asshole. Now, I am gonna give you a very important lesson (yes, I am talking to those of you who have never done anal before). There is no such thing as too much lube. You think you put enough lube on your penis? Put some more. Your asshole will thank me later.

You can probably guess what happened after. I’ll just let this GIF (how do you pronounce it btw? Does it sound more like gift or jeef?) explains the situation.


I did notice that something smelled funky when we were having our adult slumber party. Once he pulled out and grabbed a towel, I noticed that the bed sheet under my… You know what, I’ll spare you the details. Needless to say, I felt embarrassed. Due to my lack of sex education, I wasn’t aware that a bottom needed to also clean the inside of his asshole, not just the outer part of his ass (assuming that you want to have a clean, hygienic anal sex. I mean, if you’re into playing with human feces… hey, who am I to judge? You do you).  He assured me that everything was alright and asked me if I wanted to use the bathroom. If I could read his mind at the time, he was probably thinking, “yup, this guy was definitely a virgin”.

In a way, I am happy that my first anal experience was with a stranger, so I don’t have to worry about running into this person somewhere and be reminded of this incident. I remember walking back to my place feeling ashamed yet relieved. At least I won’t die a virgin.

I hope you learn something from my experience here. When in doubt, douche it out.

4 thoughts on “II. The Guy Who Took My Anal Virginity

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