12 Embarrassing Masturbation Stories That Could Have Been Prevented

Masturbation is a natural part of life, but if you're not prepared for surprises, wanking your willie can lead to some awkward situations.

Embarrassing Masturbation Stories That Could Have Been Prevented

Need a good laugh? Here are our 12 favorite stories of masturbation gone horribly wrong: 

1. The Awkward Family Gathering

Embarrassing family photo
Photo by Sheri Hooley

Redditor ENDofZERO shares this awkward tale of a lie being taken seriously:

I was jerking off and my sister walked in. I tried to hide under my covers and she was like, what are you doing. I feigned that I was checking something out on my penis, thinking she would just leave me alone. 
Nope. She got concerned and got my dad involved, so now they are all in my room trying to figure out what's wrong with my penis. Fucking awkward.

2. The Cucumber Fleshlight Incident

Penis-shaped cucumber
Photo by Charles Deluvio

Redditor NaquadahEOD shares this story of a horny male, a homemade Fleshlight, and a microwave:

One time, when I was about 12 or 13, I had the sweet idea of taking the seeds out of a cucumber, putting it in the microwave, and humping it. I was super excited about my new cucumber Fleshlight. I start humping it, but instead of pleasure, I felt burning. I had put the cucumber in the microwave for too long, and I had blisters on my shaft for several days. They were excruciating, and gym class was a new level of hell for me.


3. The Earthquake

Embarrassed man wrapped in sheet
Photo by Larm Rmah

Reddit user TheMarso recalls the time he learned a valuable lesson about earthquake preparedness:

Still remember this day. Five years ago I was just starting to get into porn and not giving a damn about the fact that I shared my room with my brother. One night at 4 AM I was under the blanket watching some weird porn and while I was doing my thing, it happened.
I kid you not, a fucking earthquake struck. Out of all the times, it decided to strike JUST when I was masturbating. I live in a religious family, i use a big tablet to watch porn AND my brother's bed is two feet away from mine. I thought I was doomed. 
So now I was crying "Oh Lord, please forgive me oh Lord!", one hand still on my penis, the other raised to the sky. I was SHITTING myself.
My dad came in and I hid myself under the blankets because I was half ass naked and the video was still playing. Scariest 30 seconds of my life 0/10 would not recommend.
TL;DR: Earthquake struck while I was masturbating.


4. The Spider Attack

Brown and black striped Huntsmen Spider
Photo by Max Kleinen

Reddit user Soracaz shared this hilarious story of a teenage boy’s life Down Under:

True story. I was chilling in the bathroom, taking one of those procrastinating poops. You know, the ones where you finished 20 minutes ago but you're really invested in this YLYL thread on /b/. So, as things normally go on that site, the thread quickly devolved into a "porn YLYL". 
So, after seeing some fresh tiddies I'm half-mast. I figure it's time to scoot on over to /gif/ and make use of my swiftly stiffening ham rocket before it ends up touching the inside of the bowl and I lose it. I load up a tried-and-true creampie thread, and go to grab my meat...
... living in Australia definitely has its ups and downs. Free healthcare, check. Chill cops who don't shoot you as soon as they get a widdle fwightened, check. Huntsman spiders the size of a medium plate at your local Chinese joint, check.
I ended up grabbing the thin hairy leg of one very angry hairy boy. In an effort to escape, he leapt from the underside of the bowl onto my now drastically deflating member. I stood up and helicopter dick'd harder than I think anyone ever has. This didn't affect our eight legged antagonist, though. 
So with a hearty blow I slapped my salami so hard that one of his legs came off and he went flying into the wall, skittering off behind the washing machine, never to be seen again.
Right then, my old man, hearing the commotion, gets up out of bed and slides open the unlocked bathroom door. There I am, pants at my ankles, meat redder than the devil’s dick, panting, staring him down. I didn't even wipe my arse. Your boy's not here to fuck spiders.

5. The Short-Sighted Stroker

Teeage boy with headphones watching porn on iphone
Photo by NeONBRAND

Reddit user Drifter74 shares this awkward masturbation story from his teen years:

When I was 14 or 15, this one time I was jacking off with my eyes closed and a pair of headphones on.
I opened my eyes and there was a stack of folded laundry on my desk that wasn't there when I started. 
Didn’t think it through...There was some avoidance in the house for a while afterwards (me avoiding mom at all cost.)

6. The Surprise Attack

Young boy looking hiding looking for secret
Photo by Dmitry Ratushny

Reddit user BagelsAreStaleDonuts shared this story of being caught off guard: 

In my house growing up, my brother's and my room both had attic access through our closets and they were connected via a small channel over the roof. 
I locked my door and, thinking I was safe, started to do my thing. A couple minutes in, my brother and his best friend burst through my closet door to try and scare me, catching me in the act. 
The bastards crawled through the cramped crawl space for like 20 minutes to be quiet as possible so I wouldn't hear them and ended up getting more than they bargained for. 
After that, I learned to tie a rope around my closet door handle before using the ole joystick. Very glad I live on my own now.

7. The Masturbator Who Drank Too Much

Teenage boy alone in bedroom
Photo by Christian Erfurt

KnowItAll811 shared this story from his college days about coming home drunk:

Back in college I was really drunk and horny after a night out drinking. I got back to my room and since I knew my roommate was gone for the night, I fired up the laptop, found my porn of choice, and started going to town. That is literally the last thing I remember.
I woke up in the morning hungover and noticed something was off immediately. I had a blanket thrown across me, one that wasn’t mine, and my laptop was closed and sitting on the nightstand. It didn’t take long for me to figure out that my roommate must have been in the room and that I had passed out while jerking off.
I texted him right away and just said “sorry.” He said “no worries but just so you know, I had Jess (his gf) and her friend with me.” So the three of them walked in and saw me sprawled out naked, dick in hand, passed out. Passes out and limp is definitely not the look I was going for. Everything was fine but it was awkward around those girls for a while.

8. The Apple Store Porn Incident

Apple store at night
Photo by Harry Cunningham

Reddit user whoaamann shared this story of accidental over-sharing at the Apple Genius Bar:

At the time I had an iPhone 4 and it was the first phone I bought on my own. Being 18 or 19 naturally a lot of porn was watched. Well one day it decided to not unlock after a fap session. I wasn't able to close tabs, clear history etc., so I make an appointment at the Apple store that day and head in. The 'genius' happened to be this kid I was somewhat friends with. He was super religious, very judgmental and liked to gossip.
Anyways, we talk for a minute and catch up. Then I tell him what's going on with my phone (leaving out the porn part of course). 
So he takes it and turns it on and of fucking course it works perfect for him! And of course as soon as he unlocks it the browser is still up and all you can see is a girl's face absolutely covered in cum! lol Haven't seen him since.

9. The Boy Who Talked Too Much

Teenage boy covering eyes from shame and embarrassment
Photo by Francisco Gonzalez

Reddit user nipplemuffins shared this story of almost getting away with it:

When I was about 11 or 12, my friend and I had figured out what masturbating was and didn't think anything of doing it in front of each other or for each other. So one time we were in the upstairs part of my house and we had just finished and my friend was going to go downstairs to get some food and he walked out of the door just as my mom was about to come in (and before I knew she was upstairs). I said "I accidentally got some of your cum on my pillow." She then walked in a split second later and said she was going to bed, hugged me and didn't make eye contact with me for at least 3 days. She has never said anything about it to this day…

10. The Light Sleeper

Man with beard sitting on sofa surfing the internet on laptop
Photo by LinkedIn Sales Navigator

Married dad naninog shared this embarrassing masturbation story that prompted him to ask Reddit for advice:

So this just happened earlier tonight. My wife was out with friends. Thought the kids were asleep and figured I'd have some solo time. Just as I'm getting a rhythm going, my 8-year-old son suddenly appears at the doorway and asks "when is mummy coming home... And what are you doing? That looks weird".
I've never felt so guilty and embarrassed in all my life. I told him to go back to bed and quickly put my hands over my lap.

11. The Wet Spot And The Awkward Conversation

Teenage male covering face with hands
Photo by Christian Erfurt

ThickPotato shared this tale of a near-miss and the awkward situation that resulted:

I once was in my room going at it like teenagers do when I could hear my mom about to come in right as I was at the point of no return. 
I jammed my dick back in my pants and it exploded all over my boxers. I then proceeded to have a 10 minute discussion with my mom about school or something while I sat there in jizz-soaked pants. I remember she asked if I wasn't feeling well cause I was acting a little off. It was almost enough to keep me from masturbating ever again. Almost.


12. The Teenage Toilet Bomber

Bathroom with pedestal sink, toilet, and shower
Photo by Filios Sazeides

Reddit user Pharasula shares this story of a time he didn’t know his own strength:

When I was 15 I completely broke a toilet masturbating. We lived in a duplex that had two bathrooms connected to a mutual bath. I used to go into one of the bathrooms and jerk off on the toilet. On either side of me was a doorway. While doing this I would brace my legs in the doorway placing one feet on one side of the door jamb and my knees on the other side. This particular time I came pretty hard which caused me to slide back and forth on the toilet slamming into the tank and shattering it. 
I told my mother that it was caused by the cold outside busting one of the pipes bursting. It wasn’t plausible at all, but I felt like she would rather believe that than know what actually happened.


Masturbation is a natural and normal part of life, but it’s still embarrassing if you’re caught in the act-especially by family members.

When you feel like playing with yourself, remember to check your surroundings, come up with a decent cover story and learn from these guys’ mistakes!

Harry D Somers

Harry D. Somers

Harry D. Somers is the editor and founder of Fresh Materials. Based in Miami Florida, he's the kinky, bisexual, horny, sex-positive blogger behind FM's articles, tutorials, and toy reviews.

Today's Fleshlight Deals

All deals
Quickshot Vantage Sleeve, Clear case, Sleeve Caps, 4 oz Fleshlube Water, 4 oz Fleshwash Toy CleanerQuickshot Vantage Pack
What's included:
  • Quickshot Vantage Sleeve
  • Clear case
  • 2 Sleeve Caps
  • 4 oz Fleshlube Water
  • 4 oz Fleshwash Toy Cleaner
Clear Pulse sleeve, Clear case, Sleeve caps, 4 oz Fleshlube Water, 4 oz Fleshwash Toy CleanerQuickshot Pulse Pack
What's included:
  • Clear Pulse sleeve
  • Clear case
  • 2 Sleeve caps
  • 4 oz Fleshlube Water
  • 4 oz Fleshwash Toy Cleaner
Black Fleshlight case, light colored FleshSack sleeve with attached scrotum and butt orifice, 4 oz Fleshlube Water, FleshWash toy cleanerFleshSack Essentials Pack
What's included:
  • Black Fleshlight case
  • Light colored FleshSack sleeve w/ attached scrotum and butt orifice
  • 4 oz Fleshlube Water
  • FleshWash toy cleaner
Pink Lady Classic Fleshlight, 8 oz Fleshlube Water, FleshWash cleanser, Renewing PowderClassic Pink Lady Essential Pack
What's included:

Further Reading

Join the Conversation