The Most Shameful Jerking Off Stories

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Get ready for nasty…

Once you’ve hit (at least) your 20s, spanking it ain’t no thang. It’s natural, healthy, and just about everyone does it. However, when people are at an age where they are still learning about their bodies and what pleasures them, they often feel guilty and embarrassed… especially when they are still living with their parents and could get caught at any moment.

Health classes usually don’t touch on the subject of self-pleasure, so teens are forced to fend for themselves. Lots of young adults are clever and experiment with household items and/or jerk off to weird things when they don’t have access to the internet. Of course awkward things happen to adults when they are playing with themselves, too, but there’s nothing like a good, old fashioned “my mom walked in on me” story. Or is there…?

Read on as people dish out their really messed up stories of self-love.

Sweet, juicy, multipurpose honeydew

Got high and f**ked 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 “its like cheese just cut the mold off” (myfirstthrowaway9183)

Spider Woman

Masturbating in the shower at age 14 (female) when I thought I had the house to myself. I decided to try to moan more and experiment with that. It got loud and ridiculous because that’s just who I am sometimes. My dad came home and I didn’t notice until after I got out of the shower. He was all “I heard some really weird noises from the bathroom. Are you okay?” “There was a spider in there and it scared me.” Nooooo. Pretty sure I experienced my first orgasm, and my dad heard it. (Waitwhatdidijustsay)

Life and Death

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 dads 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) but right between us. After about a full 2 minute hug, he let’s 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. (thebachmann)

Smashing Samus

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 Wiimote. He just kind of slowly closed the door.

Still got pizza, though. (Heavy_Cheese_Gunner)

Missing the Mark

One time I dreamt that I was wanking, yet I couldn’t cum. When I woke up my hand was jerking up and down with one of my rolls of fat. (Swiss_Army_Cheese)

Not enough hands

Chick here. Pretty much always ready for some action, don’t get enough so I take care of it myself. I don’t like anal sex with guys because they want to do that pumping action and sorry but that hurts. I do, however, enjoy anal if I do it to myself with a finger or dildo.

Anyway, I had this little finger vibrator and I was short on hands (got three things to deal with now) so I thought, I’ll just put the small vibrator halfway into my ass and leave it so I can rock this dildo and rub myself. I finished up just fine, until I realized my butt had swallowed the small vibrator. It was unreachable. Had to give myself an oily enema to get it out (and it was vibrating the whole 20 minutes it was stuck in there).

Mistakes were made. Time to invest in more appropriate equipment. (littlebirdbones)

Cumming of Age

When I was 13, my older brother bought me a pocket p**sy 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 f**king smokin. 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 f**king 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 f**king 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. (HonoredPeoples)

Damn, Solider

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

One day I was going to town on myself while watching some pornog 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… (dirk_diggler17)

A Family Affair

Getting caught by my wife jerking off to pictures of my sister-in-law. (sbashe5)

DIY Lover

I was doing an intensive Russian summer program at the University of Chicago. My roommate had bailed halfway through the ‘semester’ so I had the whole room to myself. I’d always been… self exploratory, and after a normal evening of watching porn, and flicking the bean, I still was unsatisfied. I realized I needed more than my fingers to get the feeling I REALLY wanted, so frantically looked around my room to see what I could MacGyver into something resembling a dildo. I found my condoms (good, on the right track) and started to look for anything cylindrical.

Then, I noticed it. The sunscreen spray can. It would be perfect. I cleaned off the can in the sink, unrolled the condom onto it, and got started. The only problem was that it was TOO WIDE. It didn’t matter though. I was past the point of no return with caring, and just kept going even though it hurt. I knew I couldn’t just masturbate to empty air too, so I put on the TV show I was currently watching: Hannibal. I came right as Hannibal was ripping this guy’s jaw from his head. (OhLordyMe)

Mama’s Girl

I came on my mom’s dildo at the home computer in full view of the front door to late 2000’s Brazzer balloon-boob, double-dildo lesbian porn as my mom herself burst in the front door.

It was in the years of high school when my little brother was in after-school care and I had roughly 50 minutes of golden lusty alone time between coming home from school and my mom arriving home from work, but she came home early that day. My moaning was too loud to hear an SUV roll up the gravel the driveway just outside the office area.

My tab count was higher than the white blood cells in a leukemia patient, and I’m pretty sure I was utilizing the induced gang bang effect of having multiple tabs playing videos at once. I always found real gang bang noises to be too forced, so I’d play several videos at once with good audio of real orgasms and coitus pleasures…

I was a little fortunate to have been in my silent-orgasm-deep-breathing-experimenting stage following another f**ked up over-hearing incident from me in the shower and thinking I was the only one home.

So though my face was contorted, lower half naked with an immensely-cut borrowed purple dildo gripped in my pulsing cervix, in a matter of milliseconds I managed to cum, guide my pleasure-induced claw hand to mouse-click the browser ‘X’, pull my blanket up around my wobbly lower half as I stood, and give a big, enthusiastic, “Hey Ma what are YOU doing HOME!?<3?!” faux greeting without her ever being aware of what was happening just before and as she entered the premise. I also managed to clean the dildo, dry it, and return it before she noticed that day, too.

Yes I was desperate enough to share that s**t. It breaks every safety rule I now uphold for toy sharing and sex. Also, yeah, no more family dildos. That was f***ed up. (valuethemargin)

Gravy Master

Pretty standard masturbation stories for me. When I was 18, my mom caught me watching porn and using a vibrator several times. 8 years later my mum still brings it up to me.

Gets better. When I was 19 I brought a guy home because my parents were out of town. My parents got home early and my Mum knocked but due to the music and the fact I was had a dick in my mouth I didn’t hear. So she opens the door, looks at us and said “Well now. Thats a nice one. I will tell your father to set another spot at the table for dinner”

That was an awkward dinner for him…my mum just stared this guy for a whole 5 min and finally said “Could you be a dear and pass the gravy?” (Drunk_Tavern_Wench)

Putting aside what a nice mental image that set up, how exactly does having a dick in your mouth stop your ears from picking up sound? (chubimaster343)

How do you like them apples?!

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 f**k 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 f**king 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. (thedarksentry)

Early Kinks

Ohh boy… 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 cousins soccer game… Of course my mother brings the camera… She takes it and and wants to be sure she isnt going to start recording over anything “important”… To my horror, I see the video playing and its 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. (Austinswill)

Want more tales of masturbating woe? There are plenty more on this Reddit thread.

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Original by Chewy Boese