33 Guys Recall The Riskiest Time They Ever Masturbated

Illustration by Daniella Urdinlaiz
Found on AskReddit.

1. In a Porta Potty about three minutes before a mortar attack commenced.

“Got started in a Porta Potty about three minutes before a mortar attack commenced. Stayed to finish. I have no regrets.”


2. While on camera in the county lockup.

“While on camera (I assume) in the county lockup. Twice. In my pants, obviously, back to the camera. I am ready to be judged.”


3. In psychiatrist’s chair while he went out to make coffee.

“In psychiatrist’s chair while he went out to make coffee.”


4. While my dad was tucking me in for the night.

“My dad was tucking me in for the night when I was like 9, the exact age I started fapping. He was sitting next to me (literally touching me) with his leg propped up so it created a little tent with the sheets. Me, having no shame for my fapping at the time saw it as a perfect time to crank one out. As I write this I’m sitting in the exact same bed I was in. He never found out (I think)”


5. In the reading room of a graduate library with at least 100 people in there.

“Reading room of a graduate library at a major university, there was probably at least 100 people in there. College eh.”


6. In my church’s clergy house as an altar boy.

“In my church’s clergy house as an altar boy.”


7. In a with three other people next to me in the same Jacuzzi.

“When I was 15 I jerked off in a Jacuzzi at a swimming pool with three other people next to me in the same Jacuzzi. I was a quite perverted teenager.”


8. On the top bunk bed in the same building as 50 other boys.

“At a middle school camp, in the same building as 50 other boys, sharing a bunk with my best friend…on the top bed.”


9. In the toilet of an airport.

“In the toilet of an airport 10 minutes before the gate opened.”


10. In the middle of art class in middle school, with three other people at my table.

“In the middle of art class in middle school, with three other people at my table. I didn’t get any disgusted looks and I never heard about it from anyone so I’ll assume I got away with it.”


11. Bunk beds. Creaky ones. Little sister in the bottom.

“Bunk beds. Creaky ones. Little sister in the bottom.

She’s an adult, it’s not as creepy as it sounds. Fingers crossed she didn’t know, but it has never been discussed.

I hate myself.”


12. Driving to a job site down a winding-ass road with a cliff on one side and being followed by two other work trucks.

“Driving to a job site down a winding-ass road with a cliff on one side and being followed by two other work trucks. I came in a Ziploc.”


13. In the lake while talking to my friend and his sister.

“In the lake while talking to my friend and his sister. I’m not sure how I didn’t get caught.”


14. In the waiting room of the principal’s office.

“The year is 2001. I’m in 5th grade. Was sent to the principal’s office. Principal sits at a desk at the end of a narrow hallway. Adjacent to the principal is a waiting room I had to sit in. No one else was nearby so I pulled off a quick, 3 minute fap. Seconds later, principal comes in. I was given detention for the reason I was initially there. More school faps followed.”


15. In the middle of religion class at Catholic school.

“Okay so I’m 14 and in high school and along comes the urge while I’m in the middle of religion class (mandatory at the Catholic high school I attended).

Now you’d figure if your average testosterone-fueled kid who couldn’t control himself he’d go to the bathroom and hide that shame. Not me, no. As we are learning about the sins of mankind I slide my arm out of my school jacket. However, I leave my now empty sleeve on top of the table and rest my other hand on top of it. To everyone else it would have looked like I had both arms above the table.

Away I go right there under the table, which has my classmates directly opposite me along with the rest of the 20 students and teacher. Most covert fap ever and you bet I enjoyed it. Ended up making a royal mess on the inside of my underpants that I was able to discreetly hide and clean after class.

Wasn’t until years later I realized how different my life would have been if I got caught. I’d be the kid who fapped in religion class. I’d have had to have changed schools, even towns to hide from the deserved ridicule. Really makes a man think about the subtleties of life.”


15. In a Quonset hut-like tent with about 20 other dudes.

“I was in a Quonset hut-like tent with about 20 other dudes. When I got in the tent it was pitch black, so I figured I could beat it quietly and nobody would notice since everyone was presumably asleep. I blew my load in a happy sock, and then realized my eyes had adjusted to the dark. Anyone who had been in that tent for a length of time would have been able to see me.”


16. In the bathroom upstairs of Carnegie Hall right before the chorus I was in was supposed to perform.

“I fapped in the bathroom upstairs of Carnegie Hall right before the chorus I was in was supposed to perform. Got out and the director called for the lineup to get on stage immediately after I left the bathroom.”


17. In the Pacific Ocean.

“Had a boner that just would not go away whilst swimming in the Pacific Ocean. My friends were all tanning on the beach 20 meters away. So I jacked off into the ocean to kill the dick stick.”


18. College campus library.

“College campus library. It was late at night so hardly anyone in the building. When I turned around from the desk I was sitting at, this guy was just staring at me.”


19. Driving down the highway at 85MPH.

“Driving down the highway at 85MPH was pretty risky! Don’t wanna ‘jerk’ the car too much!”


20. While my significant other was having loud sex with another guy in the next room.

“The long game:

Long term, live-in SO cheated on me.

I was working and going full time to senior year at Uni so no sex life.

Agreed to move to guest room, arrangement until I graduate and lease is up and ‘stay best friends’ to keep door open.

Gave dating and sex advice to obtain details for spank bank, no time for a sex or social life. Encouraged her to explore and push envelopes sexually.

She asked me to help her setup a dating profile and take photos for a busty pinup site. I encouraged her to use dating profile photos from photoshoot.

I ask her if it’s okay to repost photos for modeling opportunities. I post them to a big breast fetish forum with statement and location looking for modeling opportunities. Questions asked I explain my situation. Local guys from forum interested in her.

Interested guys PM me. I forward them to her dating profile with likes/dislikes.

SO elated she gets several responses from dating site. I encourage her to follow up on them and let her know she can have the place to herself on weekends. I’ll be out.

Guys from forum who contacted her PM me about the follow up. They ask me questions. I ask for a play-by-play with whatever they’re open to sharing.

Hookup is arranged. She goes out. I pretend I’m away and lock the guest bedroom door. She comes back with guy and I hear sex marathon in neighboring bedroom. I fap through it while having an emotional breakdown.

I thought I was going to get caught. I get photos and pics from that night from forum guy.

I get constant stream of pics and videos from forum guys. One was a photographer and got her on some pinup sites. It was a weird triangle.

I graduated. We renewed lease and rekindled relationship on condition she doesn’t change who she is for me and we explore hotwife relationship.”


21. Stared straight into a motel security camera and did my business.

“I’ve become the master of stealthwanking and I’m not entirely sure how. A few of my feats include:
-Back seat of a full car
-In a packed hotel room so my friend and I had to share a bed
-Airplane under a blanket while everyone thought I was asleep
-Long ago, in class, while wearing sweatpants
-MANY times while sharing a room with multiple friends
-At the beach, in about 4′ deep water
-On the very top of a big playground because I was bored
-My old job many times
-My personal favorite, in some room I found in a hotel with a security camera in it. Stared straight into the camera and did my business. Did not stop staring.

And many more. Don’t think I’ve ever gotten caught.”


22. In the college cafeteria at 3:30AM.

“I’m sharing a room with another couple of dudes, and things are always loud so I try to be away from their as much as possible (except fapping, which I do in my bathroom). The internet is godawful slow though, and getting 720P streaming is a miracle.

My college is home to over 50,000 students and one of the cafeterias has an influx of over 1,000 per day. It’s also one of the few places with wired Gigabit on hand. One Saturday evening, I decide to stay in one of the meeting rooms overlooking the cafeteria (room projected from wall overlooking cafeteria; no blinds and walls are made of glass). It’s getting late, and at about 10:00PM, all the workers are winding up and going home, and I was sure that someone was going to ask me to leave… They didn’t.

After staying there for an additional hour, I realize I am all alone and have Gigabit. I start surfing Pr0nHub and after about an hour of being horny, I get a subscription to one of those pr0n siterip websites, and start downloading videos in 1080p goodness that I didn’t have access to earlier. While they’re downloading, I start opening each one up to ensure they’re “legit”, and I start getting aroused.

Cue me downloading videos for the next 3-4 hours. It’s 3:00AM, I’ve filled in over 300Gigs of storage, and am horny as all hell. I look around—the cleaners are gone. There’s no one in the cafeteria, and I can hear anything that comes. The roads overlooking the cafeteria windows are empty, and the lights in the meeting room are shut, too.

I start jerking… To be honest, it was perhaps the best fap I’ve ever had; and at around 3:30AM, I waddle back to my room. I was never caught (no cameras in that meeting room), and I did feel weird coming to get breakfast in there the next day.

10/10 would do again.”


23. While licking my friend’s mother’s dirty panties.

“Recently while alone in my friend’s house I rooted through their mother’s laundry, very hot mother that I’ve found attractive for many years, to collect her worn and dirty panties. I licked those suckers the whole weekend and at one point had them wrapped around my face with the crotch in my nose as I fapped. Best orgasms ever and I fully plan on stealing a pair next time I go over.”


24. On an interstate road trip with my dad, mum, sister, grandad, and grandma in the car.

“On an interstate road trip with my dad, mum, sister, grandad, and grandma in the car.”


25. In the back corner of Spanish class.

“Around 1998 I sat in the back corner of Spanish class by the door and a window. I was also surrounded by cheerleaders who were wearing short cheer shorts. I successfully completed a game of pocket pool while the teacher was doing what he was doing.”


26. In church. During mass.

“In church. During mass. Sitting in a full pew up front. I was really young having discovered masturbation at an early age. I went to a Catholic school and this one teacher occasionally wore this red skirt that came slightly above her knees, but when she sat down it came up really high. So, I was sitting there with an erection and I pushed it to the side. In doing so, I discovered that rubbing the head through my pants felt nice. I started playing with my tie and using the tie to rub my tip through the pants. All of this while the priest is giving his service. Not sure if anyone noticed, but no one stopped me.”


27. Doing 80 down an interstate in Alabama.

“Probably doing 80 down an interstate in Alabama. I missed my exit.”


28. In the women’s shower of my office building.

“My office building has two private bathrooms they call ‘joggers’ bathrooms’ because they have a shower in them. They are rarely used by employees of the company I work for but are used a lot by the building security staff. There are a few lockers in there and I think that is where they keep their personal belongings while working.

(It’s also a place for people to secretly hook up—but that’s another story.)

I personally like taking showers on company time so I use them a lot.

Like I said…there are two bathrooms, one men’s and one women’s.

One night I’m meeting some friends for some drinks after work and I decide to take a quick shower beforehand. I had some time to kill anyway. I grab my shower stuff and go to the Men’s bathroom. It’s locked. And I can hear someone in there talking on a phone or something. I kinda had my heart set on a shower so I try the women’s door. If it’s locked no harm no foul…if it’s open I can just use it and lock the door behind me and it won’t matter it’s a women’s restroom…I’ll be the only one in there.

The door is open and I lock the door behind me and turn the water on. I strip down…suck in my gut and pretend there are some abs in there somewhere…then hop in the shower.

I’m in there a few mins and get all soapy and decide now is as good a time as any to rub one out. One thing you guys should know about me is…I am a lazy cummer. I can’t cum standing up. There is a little fold down seat in the shower so I flip it down and get comfortable.

I get so comfortable in fact, I don’t hear the door to the bathroom open.

You see…I locked the bathroom behind me. I know I did. I checked it twice. I didn’t want an unsuspecting woman to walk in on my shower. What I didn’t know…the security staff has a master key to the doors.

I hear a woman’s voice say…‘sorry don’t mind me I have to leave for the day and I’m just grabbing my purse.’

The shower only has a thin I’ll-fitting shower curtain blocking the view to the shower itself and I can clearly see through the gap that it’s a young black girl that works the front desk.

Something inside me got super turned on by the fact I was jerking off 5 feet away from this woman and she had no idea. I should have stopped but I was rock hard and I came right as she said ‘Sorry about that. Have a good night!’

If she had turned to her left when she walked out we would have been eye to eye. But she turned right and never saw me.

Pretty risky when you think how bad that could have gone.”


29. Middle-school health class and sitting next to my crush.

“Middle-school health class and sitting next to my crush at the time. Was able to roll my dick between my jeans and thigh by rocking my leg back and forth. Came and teacher asked if I was ok and I asked to go to bathroom. 10/10 would do again.”


30. Ten feet away from my girlfriend’s dad with the door open.

“When I was 16, I was at my gf’s house and her dad, who HATED me, made us keep the door to her room open. We were in her bed in spoon position watching TV. She gave me a handy with her dad less than 10ft from us in the next room.”


31. In my boss’s car to purposely make a mess.

“Driving through the mountains in New Mexico at night. Not that it makes what I did right, but my boss at the time was a jerk. He did something that upset my coworker enough to quit on the spot a few days beforehand. Since my buddy quit, I was charged with driving the boss’ car. I had been driving his vehicles around that state all summer with no problems but he got in my face and made a big deal about not spilling anything in the car. I was pissed and trying to figure out how to stick it to the man when I came up with my brilliant plan of rubbing one out and making a bit of a mess. I would not recommend trying to drive a car at night on a windy and curvy mountain road while masturbating.”


32. On the bus ride home after a high school football game with fifty other dudes.

“On the bus ride home after a high school football game with fifty other dudes. My girlfriend at the time sent me a naked photo on my old Nokia (the photo was about 3 pixels total). I could barely make out what it was, but it was still enough to bring on the urge to fap. I couldn’t wait. I had to fap. It was late at night, and everyone seemed to be asleep, so I just put my football bag over my lap and fapped away.”


33. At a Southern Baptist church during their Christmas program—twice.

“My family is all very strictly conservative and Baptist. My grandfather is a pastor at a Southern Baptist church. You see where this is going.

They had me in charge of the sound system for their Christmas program. The booth was at the very back of the chapel, behind all of the pews. It was around the second or third song in the program’s soundtrack that I suddenly and inexplicably got the hardest boner I had ever had. Naturally, I couldn’t let this monstrosity go to waste. I ended up cumming twice behind that booth, while managing to keep the music going, and no one ever knew. Thank god for tissues, btw.”

fappingbaptist Thought Catalog Logo Mark

More From Thought Catalog