Caught With Their Pants Down: 49 Guys Share Their Most Humiliating Masturbation Stories

Illustration by Daniella Urdinlaiz
Illustration by Daniella Urdinlaiz
Found on AskReddit.

1. Parents walked in on me four times.

“Jerking it like crazy, parents walked in and I hid it. They left, started jerking again and they walked in again and hit repeat about 3 times till I was like fuck it ‘LEAVE ME ALONE, IM HAVING A WANK.’”


2. I got caught by my wife jerking off to pictures of my sister-in-law.

“Getting caught by my wife jerking off to pictures of my sister-in-law.”


3. The entire local village was watching me and laughing.

“13 yrs old in a beach town on the Mozambican coast, middle of nowhere. No tourists, not a soul, just miles of beach. I walk 30 mins down the shore for some alone time, climb up a sand dune and sit down to start my business facing the epic horizon.

5 mins in I hear someone snigger behind me.

About 30 people from the local village, mostly teens but also women and kids, are standing in a group just staring at me. All burst into peals of laughter when they see my face. I just bolt, trying to outrun the shame, but the village kids are running alongside up on the dunes, and they have no trouble keeping pace, just pissing themselves laughing and doing wank gestures.

Always check your surroundings.”


4. Mom caught me penetrating a sub-woofer.

“I was around 12 or 13. I just started experimenting with masturbating and was exploring all different feelings. One day, I was home alone and was watching porn on my mom’s computer. I noticed that the subwoofer to the computer speakers had a pretty nice size hole to accommodate my wiener. So I eagerly lubed it up, pants down to my ankles, knees on the floor and tried to penetrate this beautiful sub-woofer. My wiener didn’t even come close to fitting but I tried anyway and all of a sudden I hear ‘OMG WHAT ARE YOU DOING?!?’ It was my mom. She was home that whole time. I tried to cover and say that I was fixing the speakers and she just turned around and never said another word about it. DONT JUDGE ME.”


5. There was an earthquake and I couldn’t tell the room was shaking.

“There was an earthquake and I legit had no idea because I was masturbating so couldn’t tell the room was shaking.”


6. The ceiling fell down right after I came.

“I was home alone and wanted to take advantage of this rare opportunity to enjoy masturbating without having to worry about stifling my pleasure. Right after I finish, I hear a HUGE crash from downstairs. I pulled my pants on and ran down to see that the ceiling had collapsed.

Yep. The ceiling fell down right after I came.

I’ve had a few other wild masturbation experiences but this one tops them all. Slightly scarred me for a bit.”


7. He wakes up, looks over and sees his teddy bear going up and down on his friend’s dick.

“Friend’s birthday party. It was a sleepover. He wakes up, looks over and sees his teddy bear going up and down on his friend’s dick.”


8. I once fucked a jar of cooked spaghetti.

“I once fucked a jar of cooked spaghetti.”


9. My dick literally began to molt.

“Jacked off with hand soap that had tiny little beads in it. Not sure if the beads caused it or something in the soap, but the day after, my dick looked like it belonged in a burn ward. It was horrible; blood-red in most spots and pink in the other. I could pee fine, but the slightest touch would cause my body to tense up because it was so tender. I could barely walk and I was young and too embarrassed to tell my mom. After a few days of hiding and dealing with horrible pain and having a dick that looked like it belonged to Freddy Krueger, my dick literally began to molt. My dick was COVERED in dry, cracked skin that peeled off in huge chunks (like a really bad sunburn). It took a week or two to finally get better and, luckily, I didn’t have any lasting cosmetic damage.”


10. I got my dick caught in a shampoo bottle.

“One time in the shower, 13-yr-old me thought it would be a good idea to stuff my limp dick into the slippery and tight neck of a shampoo bottle.

Well, it felt good for about three seconds, Then the hard plastic rim of the shampoo bottle didn’t give despite my flesh expanding.

In panic and shame I stood in the shower, paralyzed by indecision and fear, until the hot water ran out and cold water freed me from the stalwart grip of the plastic horror.

Also, the soap burned my pee hole.”


11. Fucked a honeydew melon, ate the part I didn’t cum on.

“Got high and fucked a honeydew melon, I was 15. Proceeded to cut the part I came in off and eat the rest of the melon because I was high and had the munchies. I remember in my head saying ‘it’s like cheese, just cut the mold off.’”


12. Dad hugged me to tell me grandpa had died…while I was jerking off.

“My grandpa was in the hospital with a brain tumor. We had visited him that day, but he didn’t have much time left. I was maybe 17 or 18 years old, and after we got home at 1 am I did what every teen does and whipped it out. Now I’m sitting on my bed, hoping to bust it into the trashcan, when I hear my dad’s door open across the hall. I jump underneath my comforter, hoping to cover myself up before he gets to my room, I can hear his footsteps coming at faster than normal speeds.

I was on my side in ‘fake sleep’ position when my dad opens the door, his face covered in tears. His voice breaks and he says ‘he’s gone.’ He walks over to me and just hugs me tight, meanwhile my deflating dong is (thank God still covered by thick Egyptian cotton comforter) right between us. After about a full 2-minute hug, he lets me go and leaves to tell my brother.

I have never felt more remorse for a simple wank than at that moment. May God have mercy on my soul.”


13. I’d been fucking a cloth representation of an orange alien for five years.

“When I was 13, my older brother bought me a pocket pussy because he was a cool guy.

So I still had a Space Jam pillowcase at the time….And it just so happened that I thought Lola bunny was fucking smoking. So, I’d fold the pillow around the pocket pussy and pretend like I was plowing Lola bunny.

One day, and I don’t know why, I flipped it to the other side. And I thought about fucking the Orange Monstar.

I stuck with that side of the pillow for the next five years.

When I left for college, I brought all my favorite stuff with me. Including my Space Jam pillowcase.

One day, my roommate asks me why I’ve still got a little kid’s pillowcase.

And then the epiphany hit me that I’ve been fucking a cloth representation of an Orange alien that stole Charles Barkley’s basketball talent for the last five years and that maybe it was weird for an 18-year-old to be doing that.”


14. Don’t masturbate, kids, you’ll burn down your home.

“Intoxicated, half asleep, threw my blanket off and went at it. Woke up to the smell of what I thought was melting plastic. Blanket was on bedside metal desk lamp just burning away. Turns out those awful comforters that come in a dorm pack melt instead of catching fire, which is apparently life saving for me.

Don’t masturbate, kids, you’ll burn down your home.”


15. In Iraq…in a Porta-Potty…when I started hearing explosions.

“I once got started in a Porta-Potty in Iraq. It was about 110 degrees outside, so inside the Porta-Potty is about 20 degrees warmer with the added humidity of piss and shit. Yes, I realize that the idea of masturbating in a Porta-Potty is disgusting, but desperate times call for desperate measure and it’s literally the only place I could go where people weren’t.

So, here’s my story….

One day I was going to town on myself while watching some porno on my iPod. I hear an explosion. It sounds a little far off, but it was common to hear explosions in al-Anbar province circa 2007, I figured it was a ‘controlled det’ (controlled detonation, Humvees with mine rollers would roam the roads intentionally setting off IEDs or EOD (explosive ordinance disposal)) would blow them up granted they were able to find them.

So I press pause and wait a few seconds to see if I hear another one. Nothing. Resume jerking off.

30 seconds later I hear another, this time a little closer. Once again, pause, listen, resume.

Shortly after, I hear another and repeat pausing, listening, and resuming.
Then one lands right in our compound and within a few seconds they start raining down on us. My worst fears are confirmed; they are walking in mortars (meaning those previous explosions were them firing some off and making corrections until they had us dialed in). I was so close to finishing I just stayed there and finished. I mean, what else should I have done? I didn’t have my body armor or helmet, just my weapon. I didn’t want to risk getting shrapnel on top of blue balls. Let’s just say I have never masturbated with such tenacity. People talk about beating their dick like it owed them money, I was beating my dick like there might not be a tomorrow.

After I finished, the gunfire started and the mortars were done. So I put on my gear and ran to the rooftop to return fire.

Obviously I survived unscathed…”


16. It’s grandma, and she’s holding a fucking knife.

“My grandma was crazy. She was visiting us and I was in my room doing the deed on myself. The room was totally dark because this was before I watched porn. I have schizophrenia (inherited from crazy grandma) and would often see shadows and stuff. Well, I was masturbating when I see I figure in my doorway. I thought oh I’m just seeing things and continue to masturbate under my blanket it the dark. The figure then starts to walk around the room. I look closer and I see the figure looks just like my grandma. Is she holding something? Yes, she’s holding a fucking knife. I just waited and she walked out the room the same she had come in.

She must’ve grabbed a knife from the kitchen and came up to my room with it for fuck knows what. I didn’t realize till later what actually happened but it was weird as shit.

TL:DR – crazy grandma walked around my room with a knife while I masturbated and didn’t know it was her.”


17. My neighbor caught me half-naked masturbating with a vacuum.

“When my nosy Nancy neighbor helped herself inside my house and up the stairs to my bedroom and found me half-naked masturbating with a vacuum (lol) I think I was like 13 (f) or 14 and left the front door unlocked. She said I wasn’t answering calls (family friend at the time) so she came over… it still doesn’t add up to this day. Then she sat down next to me after I put on pants about how masturbation is perfectly healthy. :/”


18. Dad had a big grin on his face.

“So I was fapping, and then I was done fapping, so I went to the bathroom to wash my hands when I suddenly hear my dad going up the stairs, towards my room. I wasn’t sure I closed the porn so I ran to my room with my hands wet. I see my dad looking into my room, he turns around to give me some fruit (he went upstairs to give it to me). He had one big grin on his face, and left. I looked into my room hoping there was nothing to see. I just looked inside my room and you could see a woman with a dick in her mouth on full screen… He definitely saw it. To my surprise, he never talked about it. I guess he was just glad I’m not gay.”


19. It wasn’t shampoo, it was after shave.

“This was shortly after I discovered masturbation. Still learning the ropes so to speak and trying to find unique ways to do it. I was having a shower when I suddenly felt the urge to have a go so I did. I hadn’t tried doing it with some sort of lubricant and shit felt absolutely amazing. Decide to keep going using what I thought was shampoo.

It was after shave.

My dick felt like the 7th ring of hell for a solid half hour.”


20. I spooged all over the remote.

“I was 14. I was in the throes of adolescent horniness. However, I could not find the key to my locked porno box. I desperately scanned my bedroom for anything resembling a boob. Then I remembered Smash Brothers Brawl and Zero Suit Samus.

I booted up my Wii and began torque-testing the crankshaft. Just as I’m about to finish, my dad walks in and asks if I want to order pizza for dinner. Eye contact was made. I’m at the point of no return, though, so I spooge all over the Wii Remote. He just kind of slowly closed the door. Still got pizza, though.”


21. I looked down to see a large cum stain in the center of my sweater.

“On my very first day of college, I took potent sedatives and ejaculated on my stomach and chest. The sedatives took hold, and I haphazardly cleaned myself with a sock, spreading it more than anything. Someone knocked on my door and invited me to the lounge area where people were playing Cards Against Humanity. I groggily threw on a sweatshirt and found the study lounge.

The students were arranged in a circle, and I sat just outside of it. I could smell myself, and every time I leaned over to place a card on the table, the people next to me jerked backwards. I was aware of my stench, yet I was too sedated to feel anxious. I kept playing, leaning forward, and I saw a guy discreetly taking a picture of my sweater with his phone. I looked down to see a large cum stain in the center of my sweater. I played some more, and the smell of cum and body odor grew in its dominance.

Still groggy and unfeeling, I excused myself from the lounge and returned to my dorm. As I arrived, I encountered someone whom I had vaguely known in high school. He talked about how much fun we would have over the semester, and I absent-mindedly said: ‘see you,’ after which I closed the door on him.
That’s how I prevented any friendships from forming during my first year of college. The stinger is that the people in my dorm were actually nice and smart for the most part. I just kept doing creepy things without knowledge of their creepiness.”


22. It looks like a Jägermeister black chicken embryo.

“It’s the day after a serious night of drinking. I’ve got the hangover to end them all. I want to spank it, but don’t want to clean up the mess. I get the bright idea to get on my knees in front of a dirty laundry basket. I shoot it there, have the wife put in a load later. Perfect.

I’m down on my knees in my boxers, I’m going at it. Phone in one hand watching something vile I’m sure. Going to town with the other. It’s about there, then I get the rumble in my gut. It can’t be contained. I’m thinking it might be a serious fart at this point. So I decide to let it out. It’s not a fart, but it’s not a lot either. My boxers are around the knees. I’m pretty sure they caught it. Fuck it. I finish up.

After I’m done, I have to look at it, right? It’s what looks like a Jägermeister black chicken embryo. A little solid piece in a pool of oily water.”


23. I pulled out my Bible and started jerking it to Song of Solomon.

“Our Wi-Fi was out and I was 14, out of desperation I pulled out my Bible and started jerking it to Song of Solomon. I’m 18 now and I don’t if there is a god or heaven, but I am going to hell.”


24. I fucking came in my pants in the back of my grade 9 math class.

“Here’s the setting. I was in grade 9, so like 14 years old. Fuckin’ hormones flying, bologna bopping every fuckin time I turn around, I was just fucked. Anyways, I had this girl move near me and she was drop dead gorgeous. Like I instantly liked her. Anyways, we became friends because she didn’t know anybody else, so we’d sit together and whatnot and we had a couple of classes together. Hold on to your ass cuz shit is going sideways here.

New setting. This girl, call her Kaley. She’s wearing a striped shirt, and flattering jeans. I swear to god it was like something out of the movies, and her smile, good god, it lit up the room. Beautiful. We were in math class, and she was leaning over to write on the board, and maybe my mind distorted things as I repeatedly think about it to make it seem hotter, but I coulda sworn she had a back arch going on. So a couple things you need to know for the rest of this to make sense:

1) I hadn’t mastered the masturbating technique. I’d literally put my finger on the end of my dick a wiggle it. Wasn’t until like the following year I figured out in porn they always jacked it, so I tried it and it felt way better.

2) I was fucked.

So I decided right fuckin then I needed a wank. So I put my hand down my pants (I was in the back of the class on the far right) and put my binder over my lap. This technique only required me moving my index finger, so it really wasn’t noticeable, and because I was like right in the mood it took like 5 minutes. One girl looked at me in the middle of it, but I played it cool and she thought nothing of it (I think). So low and behold, I fucking came in my pants in the back of my grade 9 math class. Looking back on it, I don’t know whether I should be proud or ashamed, but either way it happened.



25. I once masturbated while on duty in a lifeguard chair.

“I once masturbated while on duty in a lifeguard chair….I used the tanning oil left up there by the hot lifeguards.”


26. A boatload of old people started cheering at me from about 40 feet away.

“I jerked off in front of a boat with about 40 people in it once. near my house there’s a quarry that’s basically right on the St. Lawrence River  (I live in Kingston, ON, this is the quarry off Highway 15) and I was down there smoking weed one afternoon. there’s a small secluded section that goes out onto the river itself. the way the sun sets is fucking gorgeous and gave me a nature boner so I just jacked off right there. you can very clearly see about a kilometer in either direction down the river, and I could full well see a large yacht coming down the river. but my peepee tells my brain that this is right. this is what we’re doing. so as the boat approaches, someone must see me sanding my pipe and the boat changes course so that they can get a better look. it’s a boatload of old people. and they start fucking cheering at me from about 40 feet away. slowly going by… this is how I became an exhibitionist.”


27. My sister caught me and told everyone.

“Anyways, when I was 14ish, I was in my room jacking to Shakira, when all of a sudden, the door props open and BOOM.

My sister was there.

I yelled at her to get out, which she did. But that was not the end of it.

See masturbation is very much a sin where I’m from, so she proceeds to tell my mother, who tells my big brother, and proceeds to have to talk to me while laughing the entire time.

Even the day after I got caught I wanted to take the laptop to my room and watch some shows, but my mother forbade it. So yeah, for the rest of my teens, my mother assumed I was gonna jack it when I took my laptop to my room. Which was true half the time though, not all the time.”


28. Mom placed hot chocolate and toast in front of me while I had my eyes closed.

“I was sitting in my room masturbating with my eyes closed and a headset on. After I finish there’s a plate with hot chocolate and toast in front of me. My mom must have walked into my room and placed them there.”


29. My mom read 50 pages of graphic hardcore smut I had written.

“Probably 15 years ago now, back when I first discovered the wonders of my penis, and all the fun adventures my hand could have with it. I had this pillow I would hump and jerk off on. So I’d get a little smear of Vaseline, grease up my cock and just go to town. I’d end up with a grease stained patch in the center, cum and sweat everywhere else. I’d do this all the time, till one side was too gross. So I’d just flip it over and continue, until that side was even worse… Naturally I’d flip back to the original at that point.

During this period of masturbation, I was into writing some really graphic Pokémon fanfics, staring girls in my class… I’m talking real cringy stuff… Matt finds Beth in veridian forest, has his caterpie string shot her to a tree, so his other Pokémon could attack and rape her… I believe there was a scene with a hitmonchan using fire/ice/thunder punch on her junk over and over…

Now when this stuff wasn’t in use, I kept it in my dresser drawers. Porn mags and spiral notebooks full of Pokémon rape bestiality stories in the bottom drawer, pillow stuffed in the one above it.

This was all fine until I went to camp with a friend for a week, and my mom decided to do some of my laundry, and I wasn’t home to put it away, so she had to. Now it is worth mentioning again, the state of this pillow… It had about 6 months to a years’ worth of build-up… It was slate grey. Started off white. I get home, go to have a fap, and the pillow is gone. Check my porn stash- it is also gone. The only thing that was left were my notebooks. I opened them up as a knot of disgust filled my stomach…

She went through them, all 50+ pages with a highlighter and red pen, and edited them. Fixed my spelling errors, had to highlight things she thought were redundant or confusing, and offered some tips…

We have never spoken of this, thank god… I guess knowing my mom read 50 pages of graphic hardcore smut I had written was punishment enough…



30. I finished in my pants during a church sermon.

“I was 15 or 16, and I was surreptitiously grooming the bishop during a church sermon because I was bored. I didn’t plan it taking it very far…until I finished. In my pants. Managed to conceal it until I got home (I think, because nobody said anything).”


31. My first impression on a bunch of classmates was me on my knees in a bathtub masturbating.

“The scene: Second year of college abroad, on a ski trip to Switzerland with 3 friends, 4 or 5 acquaintances and another 15 or so people I sort of knew from school.

First night in the huge chalet we rented for the week. Everyone’s settling in, getting to know each other, having drinks, etc. I’m taking a shower in the second-floor bathroom and feeling a little wound up (some of those German girls were smoking hot) so I decide to have a wank. The ‘shower’ is actually just a tub with no curtain or anything, and it’s slippery and awkward, so I kneel down for stability, which has me facing a window, also curtainless, but I’m on the second floor, it’s night time, and there are no other houses around so fuck it.

After a nice, long wank, I finish showering, get dressed and walk downstairs to start mingling, but as soon as I do, everyone sort of quiets down and I get the distinct impression everyone’s looking at me and the girls are whispering to each other and giggling and so on. Even my friends are acting kind of strange and withdrawn. I immediately think the obvious, that they caught me masturbating, but how is that even possible? I chalk it up to paranoia (I often feel like everyone’s judging me/laughing at me,) but after a while it becomes obvious that something is actually going on.

Suddenly, I remember hearing a lot of activity and talking and laughing out on the balcony during my shower, and in a flash I realize what happened. I run upstairs to confirm my worst fears: the balcony is huge, and reaches all the way to the bathroom window, which for a good 5-10 minutes became a close-up, lighted exhibit of a naked man on his knees in a tub whacking off with his eyes closed while making a variety of o-faces. And 25 people who I had to spend not only the rest of the week-long trip with, but also the rest of the year with, had seen. And you know there’s no chance the whole school didn’t find out once we got back. I bet there’s even a picture or two of it floating around somewhere.

TL;DR: My first impression on a bunch of classmates was me on my knees in a bathtub masturbating.”


32. It’s dripping drops of blood.

“I was at my desk churning the flesh butter. I noticed at some point there was a spot of smeared blood on my forearm. I check my arm and don’t see a cut. I check my hand thinking I have a cut on a finger or something and there’s nothing. I go back rolling craps at the casino. It’s a relaxing wank, a slow deep burn, in no rush. Few minutes later and I notice some blood on my hand. Just a very small amount. So I inspect both arms and hands. Thinking I must have a cut or something somewhere. Then in horror I suspect it’s my dick. So I Sherlock Holmes that shit because obviously it’s a big concern. Nothing. My dicks perfect like always. Not a blemish on the dude piston. I sigh in relief and just figure it maybe was from a pimple or something on my body I must have brushed. Either way I cannot find the source of blood after a few minutes. So again I go back to throttling the cobra. It’s going good. I’m into it. I’m about to cum, in the heat of the moment lost in most thoughts when it finally dawns on me my dick is all lubed up. I wasn’t using lube. I look down and my cock, hand, balls are just covered in blood. I freak the fuck out. Luckily no room mates are home because I’m running through my hall now with my blood cock in my hand heading to the bathroom. Sink is perfect height for me to lob my cock and balls into it and it’s dripping drops of blood. I turn on the water and start washing. Looking to see what’s damaged my Lance of Longinus and feeing like I’m about to faint. Nothing. I don’t have a gaping wound. Nothing to explain this. So I comb every inch of me till I find it. The top of my dick has the smallest little cut. Nearly invisible from my now flaccid terrified cock. I check it out. It’s no longer bleeding because it’s not pumped full of my boiling lust blood. I go back and inspect my desk and there’s like a tiny little imperfection on the underside of my desk at the very front. I must have flicked the tip up into it at the start when I was moving in my chair or something and nicked it.”


33. I apologized to my guardian angel.

“I grew up Southern Baptist. So every masturbation story is kind of fucked up. I literally thought my guardian angel was in the room watching me as I masturbated, and I’d even apologize to them afterwards and ask Jesus to forgive me and come into my heart for the thousandth time just to be sure. How fucking sad is that?”


34. I broke a toilet seat.

“Okay, so a couple of months ago I’m at home, lounging around on my day off. I have to go to the bathroom, so I unhook my laptop and bring it in with me, scrolling through Reddit while I take care of my business. Because I’m single, and a pervert, I have far too many nsfw subs on my front page and I start to develop the urge to masturbate. This presents me a problem, as I shortly realize that I’m out of toilet paper. This would not necessarily be a big deal, I could just hop in the shower, but I’m too horny to wait till after, and obviously I can’t just plop down on the floor or the couch because I don’t particularly want to smear poo all around. The toilet seat is placed far, far too close to the wall, making it difficult to really enjoy myself, but it’s the best option I have at the time, so fuck it. While working I start to twist around, the toilet seat is cheap and plastic and protests, but I’m getting very into it and pay no attention. I start getting close, I twist around more, the seat is getting contorted but I’m really close, almost there I scoot forward, just about to explode… and the toilet seat snaps completely into. Fuck. Luckily, doesn’t interfere with my orgasm.

Bonus: I’m an American living in china, there’s no Lowes type store you can walk into and buy a new toilet seat. Had to go to a store that sells full bathroom setups to order a new one, when showing the sales lady pictures of the toilet she started swiping on my phone and found pictures of my dick.”


35. Syrup on my sweatpants.

“When I was 14 or 15 I had an old pair of sweatpants that didn’t fit me anymore. Being as horny as any teen is I needed a place to shoot my load and not have to worry about cleanup. So for nothing short of a year when I beat it I would shoot the juice onto the pant leg of this pair of sweatpants, and when one side got covered I’d flip to the other side. And then I’d throw it in the bottom of my closet under some clothes. There was a lot of memories on that pair of sweatpants.

One day I came home from school and wanted to give these sweatpants another memory. But when I went to my closet… they were gone. Maybe my parents found it! I can come up with something… I can deal with that. I wasn’t prepared for what actually happened.

My sister gets home. My little sister. Who is 11 or 12 at the time. She got home from middle school that day wearing what resembles my nightmare. She had my fucking yearlong cum-filled escapade sweatpants on. My heart sank.

Before I even said anything, she told me she didn’t have anything warm to wear to school so she went in my closet looking for anything. She found my sweatpants… ;There was some kind of syrup on them that was really hard to get off. What was that?’ ‘A syrup… what are you talking about?’ I walked away. I couldn’t do it.

I imagine she through them under the sink and scrubbed my cum off these sweatpants for a good 20 minutes and then threw them in the drier to dry. And then wore them to school like nothing ever happened.

I’ve never told this story. And I’m still disgusted by the memory.”


36. I accidentally jammed a battery up my ass.

“My most fucked-up story is more embarrassing than it is fucked up. I was maybe 13 years old and I was in my experimental stage. Anyway, I wanted to try what it’s like to have stuff in my butt while I jerked it. Since it was the first time I’d ever done something like that, my butthole had no experience so I had to start with something small. My mistake is that I started with something too small. I took an AAA battery and put it about 3/4 of the way in and started jerking it. Before I knew what had happened, the battery accidentally slipped all the way in. Shit hit the fucking fan real fast. I’m fully erect, staring at my spread butthole in the mirror whilst praying to every single god in history. I tried every way of getting it out, but it wasn’t working. Evetually I had to face defeat and call my mom and ask her to take me to the emergency room, because I had ‘sat on the couch too fast while naked and accidentally lodged a battery in my ass.’ Needless to say, panic ensued. My mother and brother drove me to the ER as quickly as possible, where I had to face multiple doctors and nurses and lie to their face. Needless to say, nobody believed my lie. However, it seems that some god answered my prayer. While I was butt naked in a fetal position on a hospital bed with a doctor’s fingers deep in my most private of regions, the doctor discovered something that proved my lie true. The battery was in sideways, meaning that there was no way that I could’ve put it in myself.

TL;DR: It seems that my 13-year-old butt hole wasn’t as tight as I had thought.”


37. Hot applesauce burned my dick.

“Was a young kid, I used up all the Vaseline from the hall closet, so I went in search of something new. Opened the refrigerator to look for something to use as lube. Decided the applesauce would feel good if I warned it up in the microwave. So I put quite a lot of applesauce in a tall glass and put it in the microwave. Touched the top of the applesauce with my finger to check the temperature… Still cold. Nuked it again. Checked the top with my finger and holy shit was it hot. Waiting for it to cool off but so ready to go shove my dick in this applesauce. Checked the top of the applesauce again. Nice and warm…. Horny as fuck I shove my dick in the warm applesauce and press it against myself so it doesn’t spill. It feels so good the first second. Then fire. Holy shit I’m burning my dick. The inside was fucking hot as shit and only the top cooled down a little. I drop the glass of applesauce on the floor and sprint to the bath tub flinging applesauce down the hallway to put my dick under cold running water and pick a couple bits of apple that seemed to have seared to my skin off. Must have squatted under the bath nozzle with ice cold water on my junk for 20 minutes wondering how I thought that was a good idea. Then cleaned up the mess leading to the bathroom and in the kitchen. I have a couple dark spots on my skin because of this still, but the story usually gets a good laugh.”


38. I noticed my neighbors were working on their roof.

“Holy shit okay so one time in 6th grade I was locked out my house after school so I just jerked it in the back yard to pass some time. Anyways about 5-10 mins after I finished I noticed my neighbors were working on their roof. By far the worst experience of my life.”


39. My brother and I made eye contact and immediately we both knew what we just did.

“I was jacking it. My brother was apparently also jacking it in the other room. We both ran into each other doing the waddle to the bathroom to clean up. We made eye contact and immediately we both knew what we just did. Kinda awkward.”


40. I had accidentally hit ‘record’ on the video camera.

“Ok so while I was about 16-17 living with my mother… I was alone one day and decided that it would be fun to hook our video camera up to the TV and watch a live feed of myself jerking it from a different angle (yea I know, weird)… well I put the camera on the TV and pointed it at the couch at a crotch position and then got in position and did the deal… I then unplugged the camera and put it back… well, about 4-5 days later we went to my little cousin’s soccer game… Of course my mother brings the camera… She takes it and wants to be sure she isn’t going to start recording over anything ‘important’… To my horror, I see the video playing and it’s at the portion where I was aiming it at the couch to get ready for my spank-o-vision session! Turns out I had accidentally hit record :-O I didn’t know what to do so I grabbed the camera and ran. I ran around like a lunatic filming over my fappage and then returned. My mother was like ‘what has gotten into you?’ and I had nothing…just shrugged.

TLDR: was literally 1 second away from having my mom watch a closeup video of me skinning the lizard.”


41. I’m shooting this massive load into the sink, and she’s just standing there watching.

“I was the IT guy for a design firm, and we were opening a second office one street over from the other. It wasn’t populated yet, but had all the desks and tech in.

I went in on a Saturday to hook-up and test the gear to connect the two offices, and it was one of those times when you either get release or you’re not going to get anything done.

I’m in the bathroom standing in front of the sink jerking-off and the door opens, and it’s my boss/owner of the company. I was right in middle of cumming, and it was one of those orgasms so intense there’s no stopping. So I’m shooting this massive load into the sink, and she’s just standing there watching.

She closes the door, and I’m all: Fuck… I wish that hadn’t happened. I knew the best way to handle it was head on, so I cleaned up, walked out and simply said: Sorry about that. Just one of those times you can’t wait. What the hell else are you gonna say?

Fortunately, we were both adults and she shrugged it off, gave me an admonishment about keeping that sort of thing at home, and that was the last we spoke of it. That’s not to say she didn’t use it to needle me now and then. Still, she wasn’t very pleased about it.”


42. Mom walked in on me with some hardcore anal porn on my screen and my dick out.

“Nothing special, my mom was buying groceries and I jacked it (I was like 14 or 15). Mom came unexpected home and wanted to ask me if I knew where her phone was. She walked in on me with some hardcore anal porn on my screen and my dick out. I said ‘oh shit, not again, these pop-ups.’ Despite that the room was completely dark and my dick was out. I stood in that room for like 20 hours not daring to go out. We never talked about it.”


43. I keep going until I hear, ‘are you fucking kidding me?’

“This one happened to me when I was about 16 years old. I was at my buddy’s house and I was sleeping over. The next morning I wake up on the top bunk of my friend’s bed with a huge boner. So I decide to start beating my meat under the covers, careful as can be not to rock the bed. Eventually I get to the point where I’m like, fuck it and start going a little harder to the point where it’s shaking the bed a bit. I think nothing of it and keep going until I hear, ‘are you fucking kidding me?’ I’m in complete shock and immediately stop everything. I could feel my face turn red and all I could say was ‘shit man.’ Got a call back later that day saying I was no longer welcome back for jizzing on his pillow.”


44. My parents saw their brilliantly stupid son with his dick out.

“It began by coming home after a very physically demanding rugby practice at 10:30. when I walked in the door everyone was asleep so like a normal teenage boy I decided to watch porn. Ten minutes into a good session I decided to go super Saiyan mode and jack it. that’s when I caught a Charlie horse in my leg. I tried to power through it causing me to fall out of my bed screaming in pain. this woke up my parents and when they walked into my room to make sure I wasn’t being murdered they saw the brilliantly stupid son with his dick out. which caused my mom to turn to my dad and say ‘where did we fuck up’ so this moment turned into a TIL that you need pre-masturbation stretch.”


45. Gave myself a white Hitler mustache.

“Had a 4-day load go off in my face once while masturbating, gave myself a white Hitler mustache.”


46. A pool of blood gushed out of my dick, tainting the snow dark red.

“Ok. So I was away on holiday in the Alps, getting shitfaced with my mates, when my gf back home started sending frisky pics and texts. It had been some days since I had had some action so I quickly became horny as a motherfucker. So I decided to walk away and rub one off. Since I was living with 4 mates in a room the hostel was a no go though, so I walked to the outskirts of town and hid myself behind a stone wall in the freezing cold and started going for it. Half way through I got a bit bored with only texts to entertain me since I had no Internet abroad so I decided to spice things up. So I took a small icicle and shoved it up my urethra. The cold tingling feeling was quite fun so I continued rubbing it with the icicle up there until warm water which I assumed was the melted ice started trickling down my dick.

I took up another spicy text to read and accidently flashed my nethers with my phone only to see a pool of blood gushing out of my dick tainting the snow dark red and my hand already covered in the scarlet liquid. Since I had nothing to stop the bleeding with I screamed and threw myself down in the snow dick first to absorb the blood head on.

After about 10 minutes of laying with my dick in the snow the bleeding stopped and I used more snow to clean the blood off and went home without finishing what I had started but with considerable less amount of blood than I came with. Went to bed and never spoke of it again until now.”


47. I didn’t realize the house was burning down.

“Maybe the time I was jacking off and I didn’t realize the house was burning down.”


48. I let my cousin’s Yorkie lick me.

“I mentioned this elsewhere, but in the peak of my tween horniness, I desperately wanted a blow job to some degree. My cousin’s Yorkie was around during a sleep over at one point so I let her lick my cack. Instead, she sniffed it for a second, then head-butt my balls. That’s the first time I came.”


49. The teacher’s aide passed me a note that said ‘keep your hands on the table.’

“In 8th grade I never learned how to control my hormones. I ended up jerking it through my pockets to any hot chick in a class I would be in. It was working pretty well until the teacher aide in my science class saw me one day and passed me a note that said ‘keep your hands on the table.’ I still cringe about it to this day. ”

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Read this: Caught With Their Panties Down: 23 Girls Share Their Most Humiliating Masturbation Stories

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