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11 Of The Most Sinful Sex Stories We’ve Ever Heard

Just in time for the end of Holy Week, eh?
by Chandra Pepino | Apr 1, 2018
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Mga kaibigan, welcome to Holy Week. This week is a time for reflection, introspection, and discernment—we’re human beings, after all, which means we are sinners one and all. We’re terrible people, but we’re terrible together. So before we (hopefully) part with our wicked ways, let’s take one last look at the sins of humankind...well, at least, the most sinful we’ve ever heard. Read on. And afterwards, we suggest a cold, cold shower.

You kiss your mama with that mouth?

“My boyfriend and I managed to have intercourse while my mother was in the room. She was sleeping on the main bed, while he and I were snuggling on a mattress on the floor (so we were a bit out of my mom’s sight). He spooned me and then entered me, and because we had to be quick, he came in under three minutes.” —CJ, 22

“Have you no shame?!”

“When I was a kid back in the late '90s, I happened upon my dad’s giant stash of porn magazines and DVDs. During the afternoons when my parents would be at work, I would be in the master’s bedroom masturbating to all this content. I found a long, strange, vibrating thing, and I began to use that as well (of course, I couldn’t physically put it inside me!). One day, my mom came home from work early and realized I was using her vibrator and Dad’s porn. She had the most mortified look on her face. Then she shouted, ‘Have you no shame?!’ and grounded me for a week. Safe to say I handled my own sex ed.” —Kaithlene, 29

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...Go, Blue Eagles?

“One of my Philosophy professors from Ateneo used to be the head of our Student Affairs Department, which meant he was aware of all the big discipline cases. One day in class, he told us about a couple who was caught having sex in the Church of the Gesù, which is inside campus. A guard found them. I think they were expelled. Why in the world would you do it in a church?!” —Michelle, 22 

Share-a-condo, share-a-condom

“I used to share a condo unit with somebody who also worked in BGC. It was technically his dad’s, but he wanted to make extra money so he took me in as a roommate. The walls were pretty thin, so when his girlfriend would come over and they’d have sex in his bedroom, I would press my ear against the wall and jack off to the sound of her moans. I didn’t have much of a sex life back then, thanks to the exhausting call-center life, so this was how I used to get off.” —Jovil, 24

The Brooklyn orgy

“I spent a few years in the States for college, where I was opened up to a whole new world of sexual desires. A classmate of mine found out about my bicuriosity and invited me to a ‘gathering’ in Bushwick, Brooklyn. It turns out that’s code for ‘orgy.’ Holy shit. There must have been 15 or 20 couples in that room, all just getting it on. Naked bodies everywhere. Men, women, straight people, homosexuals, was just a feast. Everyone was using condoms, though, and there was a facilitator to make sure we were all comfortable. I was too nervous to do anything with anyone, so I stood meekly in the corner with some other newbies. But that was the craziest thing I have ever seen.” —Theo, 33

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“I once dated a guy who liked to pretend to be a cat. Yep, you read that right. His fetish involved licking himself (and me) clean, pulling away from a makeout session to lick my entire face, scratching up each other’s can probably figure out the rest. I had a pretty huge crush on him, so I was okay with all of this—but I drew the line when he said he wanted to suck on my nipples as if I were his mama cat breastfeeding him. Whoa! Hold it right there, buddy. I’m out.” —Joyce, 23

No room for the Holy Spirit, I guess

“This is the story of how I corrupted an altar boy (and soon-to-be priest). He was being forced into the seminary by his family, so he wouldn’t be going to a ‘regular’ college like the rest of us. But we had both always known that he was gay, so we would explore our bodies together, whether it was making out in the school restroom while the other boys were playing basketball, or masturbating each other during weekends when we’d have each other over ‘to play video games.’ He did end up in the seminary for one year, but last I heard, he went back to our town to study engineering. I have a boyfriend now, but I’ll always remember him as a partner in my first sexual awakening.” —Ben, 25

Notice me, senpai

“As far as ‘sinful’ sex stories go, this might be pretty lame, but there was a point in time where I could only orgasm if I was playing Persona 5, specifically with the character Futaba Sakura. I just found her so sexy. I live in a studio unit with my entire family, so there’s absolutely no privacy. I would play late at night with the volume off, put a blanket over my lap, and masturbate to completion while she appeared on my screen. The idea of getting caught really added to the thrill.” —Ellis, 23

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World’s worst best friend

“I’m the girl who slept with her best friend’s boyfriend. I know. Hate on me all you want. I know now that it was a terrible thing to do. But two years ago, I was such a different person. I felt no guilt whenever her boyfriend would send me flirty texts late at night. It kept escalating until we ended up hooking up at least once a week, always at a motel so we wouldn’t get caught at my house or his house. How did she find out? While we were out one night and I went to the restroom, she saw a notification on my phone of her boyfriend saying ‘Hey sexy.’ She opened up my phone (the passcode hadn’t activated yet), scrolled back, and saw our messages and nude photos. It was all over after that.” —Keisha, 24

Katy Perry didn’t mean this

“My first kiss...was with my sister. I wish it weren’t true, but it is. We were 11 and 10 respectively. We sleep in the same room, and one night—I don’t know what came over me—I kissed her, and she kissed me back. There was even tongue involved at one point. I repressed this memory throughout my teenage years, but later on when I remembered, I did some research and found out that a spectrum of sexual behaviors among young children, particularly siblings, have been observed and identified by psychologists. I still find it very weird and unnerving. I try to pretend it never happened.” —Jill, 22

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Teamwork makes the dream work

“I belonged to a batch of very-horny-but-very-sexually-repressed students in high school. It was a Christian school, so we were indoctrinated to believe that acting on our sexual desires was against God’s wishes. So what did we do? Like any group of good friends, we’d back each other up. There was this dark hallway in the ground floor of our school, and two of us would stand guard while a couple used the hallway to quickly make out or give each other oral sex. Teamwork was key. Luckily we never got caught.” —JM, 24

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