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

1. The Diary of Anne Frank.

The Diary of Anne Frank.

I mean, I obviously didn’t masturbate to all the Holocaust stuff. But it was the diary of a girl, my age (at the time), who was in the process of discovering herself, both sexually and romantically. She also includes some very detailed descriptions of her body. For a horny middle-schooler, it was a reasonable thing to fap to.”
nerdcomplex42


2. Mrs. Butterworth’s bottle.

“Mrs. Butterworth’s bottle.”
ZombieChrist


3. Aunt Jemima pancake box.

“Aunt Jemima pancake box.”
mvpmets00


4. I fapped to the ‘MMMBop’ music video because I thought Taylor Hanson was a girl.

“Am a straight guy. 12-year-old me fapped to the ‘MMMBop’ music video. Thought Taylor Hanson was a girl. Not proud of myself once I found out.”
hey0oo


5. A picture of a girl with no legs below the knees and one arm.

“The one with the picture of a girl with no legs below the knees and one arm.”
BKMurder101


6. I rubbed it on a cat that was in heat.

“The first time I ever ejaculated I was rubbing it on a cat that was in heat. God, I hated myself so much.”
vocabularian


7. In a Port-A-Potty full of stinking shit, in the middle of a freaking hot desert in Iraq.

“In a Port-A-Potty full of stinking shit, in the middle of a freaking hot desert in Iraq…multiple times…Desperate times, right?”
Spillomanen


8. I literally went to Wikipedia to figure out how guys masturbated.

“My very first…when I was eighteen. Up until then I’d been super Christian and thought it was unclean and sinful, to the point where I got to hating myself for feeling all these sexual tensions. One night I just couldn’t take it anymore (there were lots of nights lying awake thinking about it), so I went ahead and masturbated. The ‘least proud’ part of the story comes in because I didn’t know how to do it… so I had to look it up online. I literally went to Wikipedia to figure out how guys masturbated. That’s just how ill-informed I was (I honestly thought masturbation was something only a handful of perverts did). It was months before I even tried it again. Since then, I’ve grown much more comfortable with myself and my sexuality, although I think all those years of repression screwed a few things up for me.”
CaptainCyoomin


9. Sears Catalog granny panty section.

“Sears Catalog granny panty section… I mean a couple of them looked okay.”
_Mr-Skeltal_


10. “Fapped in a mosque before prayers.

“Fapped in a mosque before prayers. Not my proudest moment as a Muslim.”
BrutalMetalhead666


11. I nutted at the idea of a horse trampling a woman to death.

“My least proud fap was in a bush outside and a lady rode past on a horse, and I nutted at the idea of the horse trampling her to death. Morbid 18-year-old.”
LaimMcKenzie


12. The execution of Saddam Hussein.

“The execution of Saddam Hussein.”
RabSimpson


13. Tried shoving three mushy bananas up my ass.

“Once I was spending the night at my grandma’s house, and I was zooted out from Xanax. wanted to fap but decided I also wanted a banana up my ass while doing it. well, the bananas in the kitchen were overly ripe, and in the absence of lube, I choose olive oil. went through three bananas, spilled half the olive oil bottle onto the shag carpet, put all the evidence into a grocery bag, and left the next morning without taking the bag with me (by accident). nothing was ever spoken of it.”
Driving-You-Crazy


14. Sometimes I pretend people like me and fap to the thought of it.

“I never get any private messages from hot babes looking for a 32-year-old unemployed man so sometimes I pretend people like me and fap to the thought of it.”
yaosio


15. I have nutted in the Atlantic Ocean, Mediterranean Sea, Red Sea, Persian Gulf and Indian Ocean.

“When I was on deployment in the Navy I had to stand a one hour lookout watch on the very tail end of the ship looking at the water in case someone fell overboard. Due to watch bill rotations, you stand this watch at all different times of day. On the really late/really early in the morning watches, I would fap on watch. I have nutted in the Atlantic Ocean, Mediterranean Sea, Red Sea, Persian Gulf and Indian Ocean.”
red_rye


16. I noticed a woman in a balcony had been watching me.

“This happened some ten years ago. It was winter and I had just discovered fapping and needless to say I instantly became a great fap fan. So I was walking down a street at night bordered by houses and I got this idea of fapping while walking. It was winter so I was wearing a jacket. I snuck my right hand in leaving the jacket sleeve empty. At first I was really conscious, making sure nobody noticed. But as I began to advance to the crescendo my hand movement became more and more less subtle and almost stopped walking by the time I finished. I took out my hand put it back in the jacket and began to walk and that’s when I noticed a woman in a balcony had been watching me. She shook her head and went back in. I quietly walked away.”
liquidus08


17. I got to roleplay choking 20 cute nurses and jerked one out to it later that shift.

“I work in a hospital and had to do a sort of self-defense course. Being one of the only sizeable people in the room, they asked if I would play the attacker role. I got to roleplay choking 20 cute nurses and jerked one out to it later that shift.”
AnAbundanceOfCatPics


18. Kept masturbating even with a torn ligament in my wrist.

“I tore a ligament in my dominant wrist but I don’t have enough experience to be using my other hand to masturbate so…pushed my recovery date back two weeks. Was worth it.”
Byrnesy33


19. I got caught by my dad on a camping trip.

“When I was like 12, I got caught by my dad on a camping trip. We were sharing a tent.

That’s the worst one. When I was a tween I was addicted to whacking it. I’d be constantly on the lookout for an opportunity to sneak one off. 12 was a weird time.

Now I look back on that and I find it to be really humorous but for years it hung on my shoulders as my most cringe worthy experience.”
badgers_can_be_gay


20. Repeatedly jerked off to naked Polaroids of my mom.

“These are nothing. I’m old (57). So back in the 70s there was no easy access to porn. So you’ll probably cringe when you see where this is going…. trust me, I’m full of shame and guilt still as I write this 40 years later….

My dad had a safe in his bedroom. I shoulder surfed him one day and proudly rattled off what the combo was. He freaked out like I never saw him freak before. Held me down and made me swear I had never been in that safe before. Well, I hadn’t so I didn’t lie and told him I didn’t.

Well, of course the 14-year-old me was curious and it drove me nuts wondering what was in there. So months and months of torturing myself I finally got up the nerve and I opened the safe and looked. Tucked in behind all of his coin collections was a small photo album filled with Polaroid photos of my Mom in the 50s, right after they got married, before she had me — naked.

My God was she fucking hot. And me having never seen a naked chick before, my dick went into full on nuclear meltdown mode.

So I jacked it to her — again, and again, and again. And I knew it was wrong. Very wrong. And whenever I saw my mother I felt this horrible guilt, let alone the horror of being aroused by your own mother.

Finally the neighbor next door was kind enough to throw away his collection of Playboys (or his wife did) and I found them, so I was able to stop going into that safe, thankfully. But to this day I still feel a horrible guilt and feel fucked up about it.”
SomewhatAnon


21. I’m in the bathroom trying to rub one out while she is yelling at the kids, and the kids are hitting each other.

“Got a vasectomy about 6 months ago. Finally time to get tested to see if I was shooting blanks or not. When I left the doctor’s office after the vasectomy, they told me to call ahead to the lab of my choice to make sure they could run the test, because the sample is time sensitive.

I called around to several labs, none answered. I knew they were open, and there was one that is close to home, so I just drove up there. Lady says they can do the test, and says do you have your sample for the test. I did not, since I wasn’t sure if they could do the test or not. So I said, no I will come back with it. Now I have two choices, beat off in their small bathroom in the waiting room with her literally on the other side of the door, or go back home. I decide to go back home.

So I get home and my wife asks why I’m home, and I tell her. The kids were being especially bad that day. I’m in the bathroom trying to rub one out while she is yelling at the kids, and the kids are hitting each other, etc. Could barely get it done but somehow I did. Didn’t enjoy it at all.”
twobadkidsin412


22. Girlfriend caught me scoping her mom’s thong-clad backside while ineffectually hiding a boner.

“My ex was hot, her mom was hotter, and wore skimpier swimsuits. Girlfriend caught me scoping her mom’s thong-clad backside while ineffectually hiding a boner. Argument ensued, smoothed things over, then went to bathroom to knock one out. Teenage me was ashamed, 40-year-old me gets it.”
Soopercow


23. Skipped school to jerk off in a graveyard.

“Skipped school fapped in a graveyard, fapped behind the cash register at my old job when it was quiet, fapped off a bridge on New Year’s Eve, fapped in the middle of a vineyard. pretty much fapped everywhere.”
caphello


24. Thought farting would be a turn-on.

“I was 11, first fap ever. Thought farting would be a turn-on. I ended up shitting myself and walking with a poo-ey ass to the bathroom and didn’t jack off for 2 years after that.”
AwesomeDiamond


25. Against the handle of a vibrating lawn mower, while I was actively mowing the lawn.

“Against the handle of a vibrating lawn mower, while I was actively mowing the lawn. I was about 13 and came in my pants. Quite messy.”
fascinatedone


26. As I was fapping, a gun fight broke out. I continued.

“I live in the inner city and as I was fapping, a gun fight broke out. I still continued even as I thought about the people getting killed…”
Trollassbitch


27. I beat it to this wooden African tribal sculpture of a topless village girl.

“I beat it to this wooden African tribal sculpture of a topless village girl when I was about 12-13 which my mom kept in our living room. Another top contender would be me jerking off to a nude plastic doll (one of those cheap Barbie knockoffs) by shoving it down my pants and moving it up and down along my pubescent dick. Definitely some of the worst/lowest moments in my fapping history but I turned out surprisingly non weird with regards to any sexual fetishes so I suppose it wasn’t too bad.”
the_kid_from_limbo


28. I paid a girl to record herself talking shit about me.

“I paid a girl to record herself talking shit about me. I gave her a list of my insecurities and everything. Damn it’s painful to watch at any ordinary time but when I’m horny, it’s such a turn on.”
Deadlycalculator


29. The door suddenly opened up and there’s my father.

“I was about 13yo and got the brilliant idea of quick fap while I was in the bathroom. This was before smartphones so I had to go old school and imagine stuff in my head. While I’m going at it the door suddenly opened up and there’s my father…18 years later and it’s still not one of my proudest moment.”
freakinGurka


30. I did it to a porn video of Amber Rayne after learning she’d died that day.

“To this video, and porn star Amber Rayne had just died that day and all the comments were saying RIP. I finished, then googled to see if it was real and the shame sank in that I willingly kept going even.”
adamv123321


31. I fapped to Kari Byron crying while being subjected to Chinese water torture on Mythbusters.

“I fapped to Kari Byron crying while being subjected to Chinese water torture on Mythbusters.”
TheVegetaMonologues


32. Around me, a group of people were laughing and pointing at me.

“Sigh…It was at a music festival which took place in the woods. I took half a pill of ecstasy and took the other half about 15 minutes later because I didn’t feel anything. Huge mistake. The next 3-4 hours or so I can’t recall at all. Next thing I know is me slowly ‘waking up’ from my trip, laying on my back in the woods next to the dance floor. Around me, a group of people were laughing and pointing at me. It took me quite a few seconds to realize, I was still stroking my flaccid dick like a madman. That was the last time I took ecstasy.”
marekmorello


33. I ended up jizzing to a pic of my grandmother.

“I used my mum’s phone to watch porn (already shameful) and while I was climaxing my grandmother called, so I ended up jizzing to a pic of my gram gram.”
PM_ME_SHACO_RULE_34


34. I masturbated to a video of my parents having sex.

“I was going through old family videos when I was about 16. It was mainly just videos of my brother and I being idiots when we were young kids.

Well, one of the tapes was cut short by another recording. It turned out my parents decided to make a sex tape. Instead of turning it off and forgetting it ever happened, I de-clothed and had a great wank.

I then put the videos back in the TV cabinet and never thought about it again. That was until I came home from University a few years later and my parents were telling the story of my brother stumbling along their video and how awkward it was. I just played along and acted like that was the most awkward part of the story.”
FluffyDoDo


35. In my church on the second-floor balcony during a 10 am Sunday service.

“In my church on the second-floor balcony during a 10 am Sunday service.”
Chrollo


36. I had sex with a semi-rotten cantaloupe.

“I have beat it everywhere you can imagine except on space or on a boat. I have beat it on plane, train, and automobile. I have beat it in a church and a theater, I have beat it in a car in the parking lot at work on break. I accidentally got some nut on my black sweater, and jokingly told my coworkers it was cum and they just laughed. I’ve beat it in the middle of the forest 50 miles from civilization and I’ve beat it in school more times than I can count. I’ve beat it in a carpet cleaning van, and in a jail cell. I’ve beat it in a hospital. I’ve beat it every single place I can think of, but my least proud fap was probably in my grandparents’ backyard when I was thirteen. It was 2 AM and I was horny as can be and the night was warm. So I upped and went into the backyard and lo and behold I found a semi-rotten cantaloupe. Pushed some fingers into the melon then roused it with my Richard. Didn’t seem too shaming.”
YodasHutOnDagobah


37. When she left the room, I splooged in 20 seconds and wiped my cum inside her fish tank.

“I was about 14 and in my crush’s room. She left the room to do something and I couldn’t help my horny 14-year-old self and rubbed one out in about 20 seconds. I splooged into my other hand and didn’t know what to do with it. So, I scraped my hand onto the inside edge of her fish tank. The fish ate it up and she walked back in.”
graveyboat2276


38. Went to the school’s bathroom, locked myself in a toilet room, came and went back to class. Everybody fucking knew.

“This is a risky one…

I was at school (University) in the middle of the most boring cognitivism lecture when my teacher said something about ‘… and that’s why when we have erotic dreams we don’t actually feel the sexual act, but we do feel pretty much anything else easily in other kinds of dreams,’ which made me remember a dream I had about a classmate recently.

Went to the school’s bathroom, locked myself in a toilet room, came and went back to class. Everybody fucking knew. I was just so damn bored that I did it almost unconsciously. But yeah, they all knew.”
IceBlack88


39. Jerked off in the hospital while people were dying all around me.

“I got into hospital because of an epileptic seizure. I was there for a week. I was the only person in the room, and I had my own shower.

I couldn’t do anything for day 5. My girlfriend visited me every time, and I asked her to flash her boobs to me. She did. That night I went to the shower and I fapped.

I was so ashamed after I came. I was standing under the shower thinking: “Fucking hell dude, people are dying right now in this floor, and in this same hospital, maybe even the next room to mine”. It was absolutely horrible.”
Hunthrowaway


40. The 2004 Olympics, I fapped to the female 100-meter sprint.

“The 2004 Olympics, I fapped to the female 100-meter sprint. I was young.”
Lewi25


41. Fapping to pictures of my fiancée in the shower in jail.

“Probably fapping to pictures of my fiancée in the shower in jail. I mean it was just sad. I was the one in jail in the shower.”
SoggyNach0s


42. My most guilty was me imagining strangling my neighbor.

“I have had many, but my most guilty was me imagining strangling my neighbor.

Not because she was hot but because she like kept beating my dick.”
A_wild_penis_puncher


43. I would actually beat it with my hand.

“When I first learned about fapping I heard it called beating off.

So I would actually beat it. Hold the base in one hand and then basically slap it back and forth with the other. Just fucking hit my dick over and over.

Did that a few times and then one day it was sore so I was rubbing it. Hot damn that felt way better. Fuck I’m a genius.

So those first three or four are my least proud.”
not-my-real-name0404


44. She got pissed at me when I shot my load on her carpet.

“My (now ex) girlfriend when I was 18-19 insisted she get to watch me crank it before we did anything sexual, so I had to stand in the middle of her room with my pants around my ankles and crank it whilst she watched.

It was just weirdly uncomfortable, like she was scrutinizing my every movement. She seemed to be into it though, but like, when I’m cranking it, I usually just wanna get comfy, ya know?

Whereas this time, I was concentrating on not doing anything too weird, and also not having any porn on was foreign to me. And to top it all off, she got pissed at me when I shot my load on her carpet. I mean, what the fuck was I supposed to do?

In retrospect, it could’ve been a domination thing, but I feel she was just more curious about how I went about it.

Nevertheless, I’d rate it 3/10 personally, wouldn’t do again.”
TheeAJPowell


45. Upside down in the shower, water ran down my nostrils, gave me an extremely severe sinus infection.

“Upside down in the shower, water ran down my nostrils, gave me an extremely severe sinus infection. Also pulled a muscle in my neck, so I was forced to cry out in pain every time I sneezed (this also prevented my neck from healing for the next two weeks).”
Attackbear01


46. Find a nice phone booth, go at it, get a ride home from a cop.

“2am, really fucked up drunk, stumbling down a main road in the middle of a city, find a nice phone booth, go at it, get a ride home from a cop.”
KnockingDevil


47. Kellyanne Conway.

“Kellyanne Conway. I like old, leathery blondes, but this…this was too much.”
Vyzantinist


48. Drug test for my first job…gave me cup to piss in and I’m sure there was some sperm in there.

“Drug test for my first job…gave me cup to piss in and I’m sure there was some sperm in there lol…yes I got the job.”
JRocK01


49. Innocent Christian boy jerks off to the Bible.

“I grew up in a very conservative religious household, and was put through a religious school, with no sex education.

Always had very strict parental controls on our internet, and all the art and music and basically any form of media in the house was Christian in nature (Christian books, Christian music, Christian art, etc.) so being a 13-year-old, getting these weird feelings were very hard to understand.

One afternoon, I was reading my bible like a good little Christian boy, and I came across the book ‘Song of Solomon’, which, if you aren’t familiar with the Bible, is basically about a newlywed couple discovering each other for the first time.

That was pretty much the first time I’d seen or heard a description of a woman in that type of way, and it got me excited. For the next few months I used those verses shamelessly to get myself off, didn’t realize how messed up it was until years later.

TLDR: Innocent Christian boy jerks off to the Bible.”
feelthatk188


50. I went to her funeral, saw her in the casket and had to take a trip to the restroom.

“This girl at school who was super-hot died, I went to her funeral, saw her in the casket and had to take a trip to the restroom. I’m not proud of it, but I also didn’t want to walk around a funeral parlor with a boner.”
gives-out-hugs


51. I jerk myself off to completion while wearing a pair of a family member’s white women’s panties.

“I jerk myself off to completion while wearing a pair of white women’s panties. Now if that wasn’t sad enough this particular pair has a possibility of four owners, which are my grandmother, my aunt (oldest), my mom, or my other aunt (youngest).

So yea not my proudest moment.”
Justsadfappingday


52. I jerked off while smelling my aunt’s wet G-string.

“Fapping while smelling my aunt’s wet G-string.”
dankmasterflash


43. I jacked it to my sister.

“My sister….Don’t judge me! She has really nice boobs.”
jackwhite6


54. I masturbated to Ivanka Trump.

“I masturbated to Ivanka Trump once. She was in a really tight dress and I didn’t know that it was her.”
fruitclup


55. I fucked a Scooby Doo doll and then put it back into my mother’s sleeping arms.

“I was very sick. Just discovered how to milk my penis. Was violently vomiting and mother was sleeping in the same room to keep her eye on me. However this would not stop me from my mission. My lettuce WAS going to be spanked that night, NO EXCEPTIONS. I scanned the room for a quick moment. Her eyes were closed. My absolute solitude was confirmed. The pumping begins, but shortly I have a better idea. My stuffed Scooby Doo would feel much better, BUT ALAS!!!! Scooby Doo was in the clutches of my sleeping mother. This would not stop me. I spent about 3 minutes standing over my sleeping parent with a raging boner to get my fuck doll. Mission accomplished. He was mine. I spend the next 45 seconds showing Scooby who was the boss (still next to my mom by the way) and I finish. Coating Scooby’s tail region in sticky goo. I rub the good back into my balls because how else would I clean it, and thoroughly disgusted with myself I throw Scooby back onto my mom’s bed and go to sleep, afraid to look my pathetic self in the mirror.”
2glamtogiveadamn


56. I fucked the shit out of a pillow.

“My gf and I had been together for a few months, and I was back visiting my folks place for a couple weeks on vacation to go to a friend’s wedding. I hadn’t even had that much to drink, but I was all dressed up, and had come home around midnight, still in my suit, playing video games alone at home –my folks were away for the night. Then the doorbell rings.

That’s when I remember that family friends of ours who live outside of town had told us that their daughter was coming into town to go to another wedding (it was summer), and could she crash at our house that night, because there was lots of room? to which, of course my family said ‘sure.’

Now I’d met this girl several times before, and we were cool, but there was never any particular tension between us. This night, however, she was all dressed up, had her make up done perfectly and she was HOT AF. I’m normally a pretty honest guy, but I swear I’ve never been more tempted in my life to cheat on someone, and I was picking up definite flirtation vibes. Obviously, take my drunken recollection with a grain of salt, but I sincerely think she was as DTF as I was/wanted-to-be; neither of us was expecting a such an obvious opportunity to get laid at that stage of the night, but there we were…

So I offer her some tea (no wine) I show her the spare bedroom, how to use the weird shower we have in our house etc. Then the pause in the bedroom doorway to say “ok, goodnight… ” [crazy long awkward pause with our faces about a foot away from each other]… [turn], “all right then”.

oh man… I still have that image of her in the doorframe etched permanently into my mind. Family friend, if you ever read this…. I so badly wanted to jump your bones at that moment, I swear my turn away did not stem from lack of desire.

Anyway, at that point I was unbelievably horny, so I went back into my room and noticed that some of my gfs clothing was mixed in with my stuff so I put her skirt and blouse around a pillow, and stuffed some tissues where the breasts would be, so it kinda looked like an armless, legless replica of her, put a condom on, and then fucked the shit out of that pillow. Immediately afterwards was a feeling of post-fap shame from ‘ugh, did I just fuck a pillow,’ combined with ‘Welp, I didn’t cheat on anyone tonight”

Proud and ashamed. I guess mostly proud that I could improvise a DIY fuck-doll on the spot.”
Ibangedmypillowonce


57. All at one time, I had the electrical anal stimulator, power drill Fleshlight, Oculus fake nude device, electrical nipple stimulator, binaural beats playing in my ears, and I also wore a butt plug….

“After watching the show Dirty Jobs, I saw an episode about a device they used to electro-ejaculate bulls for semen collection. Intrigued, I did some research and actually ended up finding the patent for the device. After reading through the patent, I was ready to try to make a similar device myself. I’d just finished my electrical engineering degree, and went back through my text books to find the schematics for a sine wave generator that used operational amplifiers. I got the circuit working and added an additional amplifier stage to get a pretty stout output from the device and also purchased an anal electrode from the internet to use it with. After testing it out, it actually worked to some extent. But for some reason I didn’t stop there. I took 20 hours of online courses learning how to use Photoshop and taught myself how to Photoshop someone’s face onto a naked body. I took a picture of my friend’s face she had sent me and after about 10 hours had a decently believable nude picture. But for some reason I didn’t stop there. I figured out how to have the picture displayed on my Oculus Rift so that her fake naked figure would take up my entire field of vision. Also, for some reason I didn’t stop there. I purchased a Fleshlight online and created a mechanism using a power drill and crankshaft scheme so that the device would automatically jerk me off. I modified the trigger circuit using a potentiometer for precise speed control. I also purchased a muscle stimulator and tested it out for use on my nipples. Finally the day had come for me to put the system together – All at one time, I had the electrical anal stimulator, power drill Fleshlight, Oculus fake nude device, electrical nipple stimulator, binaural beats playing in my ears, and I also wore a butt plug around all day and taped it to my face so that when I breathed through my nose I got the heavy sweaty smell of my own asshole. While this all was happening I was also high off of 2 joints and 2 hits of acid. I’m on the fence on the experience, tilting between proud and disgusted. My therapist told me the other day ‘Don’t worry, you aren’t doing anything that everybody else isn’t also doing,’ so at least I can reassure myself that a good portion of the population (40%??) also has done the same thing.”
Mikeslemonade


58. I jacked it to a pair of silicone tits that belonged to my stepmom.

“So my dad is getting remarried, and he lives really far away, so I’m staying there for a few weeks. I’m 13.

Big house, and I basically get a big bathroom for myself, that the rest of the family don’t use much. One day looking for more soap, I strike gold. A pretty realistic pair of tits made of silicone, with nipples and all. What is this? I do not know. So I fuck them. (I remember them as being in one piece, I guess I folded them around my dick.)

Still baffled by why they even exist, feeling I’ve done something wrong, I manage to hold my hormonal hot dog holstered and stick to beating it without molesting this unexplained pair of tits…

Fast-forward a week. I’m standing behind the photographer just as he is taking my dad and my stepmom’s wedding photo, when I see her adjust them…”
KetchupGuderian


59. I made porn out of a pen, paper, and a calculator.

“I turned fapping into a game using pen, paper, and a random number generator on my calculator.

I’d create a scenario, perhaps and haunted house that I needed to escape from or an alien planet that needed exploring.

Then I’d create 10 or so varying ‘enemies’ to suit the theme. These could be anything from vampires to tentacle monsters etc.

Finally, I created a female character for me to play as.

All of the monsters, of course, tried to fuck/have their way with the girl and make her cum.

By the time I’d filled an A6 booklet with ideas, scenarios, and characters I realized how deep down the rabbit hole I’d gone. Haha

On the bright side two of my ex-girlfriends enjoyed the games. One of them absolutely loved them and we stayed friends with benefits for a long time.
So yeah, tell a horny 14-year-old that he can’t use the internet and he’ll make smut out of a pen, paper, and a calculator.”
Onyxdime


60. I jacked it to the Chyna porno on the day she died.

“I jacked it to the Chyna porno on the day she died. I told my girlfriend and she mocks me mercilessly for it.”
birdslice


61. Mom caught me while leafing through Glamour magazine.

“My mother caught me.

I was alone…

I stopped by the house to drop the car off, and I went inside for a few minutes…Nobody was there – they’re supposed to be working. My mother had a Glamour magazine. I started leafing through it…”
I_am_oneiros


62. After my drunk stepmom passed out on top of me.

“One time when I was 13 my stepmom and dad got drunk. When it was time for bed my stepmum decided to collapse on top of me on my bed. This was the closest I’d ever gotten to a female so I waited for them both to pass out and fapped myself raw to the memory. So, so shameful, and even more shameful to say that that’s not the only fap I’ve had involving fantasizing about my stepmother.”
harveyhersey


63. The scene in Star Wars where Padme is screaming in agony.

“I used to fap to that scene in Star Wars Episode III: Revenge of the Sith where Anakin dreams Padme is giving childbirth and she’s screaming in agony and begging for help. Yep.”
Noodlesyes


64. I jerked it to a KFC toy of Halle Berry.

“I jerked it to a KFC toy of Halle Berry from X2. This one.
FireTigerThrowdown


65. Jerked it to the sight of a guy sucking another guy’s dick.

“Was watching a 3-way porno. guy started sucking other guy’s dick. I kept going…”
Call_me_Thor


66. Gave my meat a good ol’ beat while sniffing my crush’s jacket.

“My crush left her jacket with me because I was dropping her off to meet her friend at a mall and her bag was full. Went home and gave my meat a good ol’ beat while smelling her sweet-scented jacket.”
cheese2x


67. On an international flight under the cover of a blanket.

“I was fifteen and on an international flight. The flight attendant was hot as fuck, and I rubbed one out on my seat under the cover of a blanket.”
dijitaq


68. Science-book vagina.

“Science-book vagina.”
Headown998


69. Used my Mom’s underwear multiple times.

“Fapped with my Mom’s underwear multiple times. Not proud of that one.”
OkArmordillo


70. I fapped to a GTA 4 prostitute with my turtle beaches on and two of my friends having a conversation.

“I fapped to a GTA 4 prostitute with my turtle beaches on and two of my friends having a conversation in an Xbox party. I had my mic muted, but I still can’t believe I did that.”
Moonkeyman120


71. National Geographic.

“Let me tell you about a dirty little novel called National Geographic.”
mygeorgeiscurious


72. I loved fucking grandma’s Electrolux when I was a teenager.

“Somehow my mother ended up with my grandmother’s old Electrolux canister vacuum.

It gave the most incredible blow job ever.

I have no shame, and tell the story of my love affair with the Electrolux quite often.

Anyway, one day I’m on the road and we pass through Augusta, Georgia….I wanted to see if I could buy a souvenir shot glass at their gift shop (closed to the public of course) but we end up driving past a big Electrolux factory with the name on the side of the building and I stopped to take a photo which baffled the 4 co-workers on this road trip.

I proceeded to tell them the story of how I loved fucking grandma’s Electrolux when I was a teenager.”
Bojackson16


73. I tugged one out after putting the used gum of a girl I liked into my mouth.

“A girl I liked spit out her gum, and me being a stupid weird kid, I picked it up and put it in my mouth. I got an insta-boner thinking about it being in her mouth and went to the nearest restroom and tugged one out.”
frenchtoastwizard


74. Half-hour gas-station meth jack.

“Drove 22 hours to go to a concert with some friends (Foo Fighters). My friends were all straight-edge; no drugs, no cigs, no alcohol. No nothing. But me? Well, if you’ve read my most upvoted comment, you’ll know that I’m gonna tell a meth story.

So here’s the thing. Meth makes you orgasm in ways you shouldn’t. It makes flail and flop like a fish. It makes you convulse head to toe as your whole body is electrified with pleasure that you’ve never felt before.

After 20 hours on the road, we stop at a small gas station. I sneak into the bathroom with my pipe and smoke hit after fatty hit until my dome is tingling. Okay, now I’m ready.

But oh shit! It’s 2000-something and smart phones don’t exist yet. So how do I fap?

I go out of the bathroom and go to the counter and buy a copy of Hustler and Penthouse. Oh shit, my buddies are in the car outside waiting for me! I told them I just had to piss real quick (actually had to smoke a couple fat bowls of meth in the restroom). So what do I do?

I go outside, nudie mags in hand and tell my buddies that I have to take a shit really bad (can’t admit I’m fapping).

So I go in the bathroom and get to it. It’s a good issue of Hustler. You know the Beaver Hunt section? If you don’t know, Beaver Hunt is basically what we had before /r/GoneWild became a thing. Anyway, it takes a while to cum when you’re on meth. Maybe 20-30 minutes? I wasn’t keeping track of time. But I jerked for a looooong time, and I’m out of breath, drenched in sweat and exhausted. And I finally cum. And it was amazing, like it always is when you’ve just recently put a shit load of meth into your brain. I flop around and flail off the toilet, smacking my elbow on the toilet paper dispenser on the way down, as I shoot what feels like gallons of semen all over the restroom. It seriously kept coming. Meth does that to you. Makes you pump like the god damn Deepwater Horizon underwater footage.

So I clean up my mess, and open the door to find a line of 3 guys waiting for the rest room. It smells like meth and semen. And I’m soaked in sweat. And I’m still breathing heavy. And I’m carrying nudie mags. Why didn’t I throw them away? Because they cost me, like, $15.

I go out to the car and my friends all look at me. They know what I did. Well, they know I jerked off. But they don’t know about the meth. Thankfully, they’re kind enough to not call me out and we just continue driving along like I didn’t just unleash a firehose of semen in a public restroom.

I still have those porno mags too. I don’t know why. Even in this age of internet porn, I still have the porno mags I jerked off to when I was 14. I can’t bring myself to throw away the ladies who took care of me for so many years. Or the dirty whores who got me off in that gas station bathroom. I love them and I will keep them hidden in my house until my wife finds them and throws them away.”
Ramza_Claus


75. I came in my teddy bear.

“When I was about 12 I had a teddy bear and it had an opening in its back from wear and tear I was horny and one thing led to another and I came in my teddy bear. I threw it out that day.”
TheCerealKillar


76. Jerked off to a boarding-school clerk’s thigh gap while she consoled my roommate.

“Wow, I have so many that it’s hard to choose one. I guess the least proud would be around age 13. I was in a private boarding school and slept in a dorm for 6 with three bunk beds. I had the bottom bunk and convinced my bunk mate to fake being homesick so the female staff member on duty would console him. He put on a great show with tears and all, while her tight 1980s jeans put her gap inches from my face. The other four roommates looked on in astonishment while I wanked and came in less than three minutes.”
fapalotte


77. Jerked off to the idea that my girlfriend might have syphilis.

“Installing insulation in the crawlspace of a client’s house

• my (now ex) gf had just called me letting me know one of her exes called her to tell her he had syphilis so she was gonna go get checked.

• so I started thinking about the fact that we had recently had sex and I could be infected too.

• then I started thinking about sex in general.

• so I unzipped the coveralls and there I was slapping ham while covered in dirt and fiberglass insulation debris, staring off into the cramped, dusty crawlspace and still wearing my respirator and goggles.

• because my gf might have syphilis.”
Prince_Edward_IV


78. In the hospital bathroom surrounded by family as my grandfather was on his death bed.

“In the hospital bathroom surrounded by family as my grandfather was on his death bed.”
postALEXpress


79. Spied on a girl sitting in a hot tub.

“I worked at a hotel over the summer in a busy tourist town. I was a front desk agent, and a family checked in, their oldest daughter being an absolute goddess, chiseled by the gods. There was an empty room overlooking the hot tub and I was on a 30 minute break.

So I notice she went into the hot tub outside, so I book it up to the empty room, proceed to close the shuttered blinds, and peer through the bottom of one and jerk off to her sitting in the hot tub.

One year and a half years later, we are dating for a year, I moved from Canada to Texas, and she still brings it up to this day. Because I told her.

Least Proud/Most Proud moment.”
adoway


80. Jerked continuously for eight hours on Adderall.

“Well, long story short I was on Adderall and jerked continuously for 8 hours to a stream on Chaturbate…Let’s just say I could’ve filled an 8oz cup. No regrets.”
DeepInItAustin


81. I banged a toy monkey.

“My brother had this monkey that you could put your hand into and move the hands around and squeeze the thing inside to make noise. Well the hole to put your hand in was at the bottom and me being a young horny idiot thought why not bang the monkey… So I did. Not proud of this one.”
ItsAViciousCircle


82. I had my way with a cheese pizza.

“Cheese pizza. I have to admit it; I was in a dark place and ordered a Domino’s cheese pizza and had my way with it.”
WeakStreamZ


83. Jerked off underwater while snorkeling—the fish ate my cum.

“Young and horny on a snorkel trip. Had the urge so I took a big breath and dove down. Wedged myself underneath a rock to do the deed while I thought about all of the bikinis topside. Fish ate it. On second thought this is both my most and my least proud fap.”
inantbh


84. A girl killed herself after being bullied for a porn video—I jerked off to that video.

“A girl near my school got bullied for a porn video she did for casting couch. She killed herself. I found the video and it was so hot. Guilty as hell fap :(”
djpapamidnite


85. Cousin’s wife’s boobs, even though I hated her.

“Cousin’s wife fucked over my credit, hated her guts. I remembered a while back I accidentally saw her big bouncy juicy bewbs by accident. It really was an accident but she did that ‘AHHHH!!! Jiggle jiggle’ move. Went into the deep recesses of my mind and forced a temporary photographic memory retrieval. It was fueled by anger. I fapped hard and splooged super hard. Felt bad later when I forgave her lol.”
AIwaysSaIty


86. Jerked off to an article about a girl bullying someone, to the point she eventually beat them to death.

“Jerked off to an article about a girl bullying someone, to the point she eventually beat them to death. I kinda pretended I was her victim.”
WhimsicalTastes


87. Thinking about a dead ex.

“Thinking about a dead ex.”
I_Am_NOT_The_Titan


88. Cut a hole into back of one of the stuffed animals and proceeded to fuck it.

“Snuck into theater classroom during lunch, cut a hole into back of one of the stuffed animals on the top shelves, and proceeded to fuck it.

Someone walked in and I tried to make it look like I wasn’t doing anything. No idea if anyone found out or they did and never said anything about it.

Now I have a Fleshlight.”
IAmTheNight2014


89. Fucked wet sand.

“Actual least proud fap. I was at a sandbar when I was 14 or something. Found this little pond in the back. Took off my shorts and fucked the wet sand.”
TheGuyWhoLikesThings


90. Hand-drawn crappy picture I hid under my bed.

“Hand-drawn crappy picture I hid under my bed. My artistic skills were…not good. I drew these different shitty characters with different breast types. They had names based on their breast types. One was named Gap. One day I couldn’t find the picture under my bed. I still shudder to think if my parents found it and what their thoughts were.”
50Centrifuge


91. On an airplane, surrounded by people.

“On an airplane. Not in the bathroom. After everyone had boarded and we were still at the gate. No I was not the only person in my row of seats.”
fonzie90tx


92. While driving—hit a mailbox and tore off my car mirror.

“I was driving to work one day and decided to fap. I was paying more attention to fapping than driving and hit a mailbox with my mirror and tore my mirror off of my car…”
ed900036


93. With my dick covered by a hat in the lunchroom.

“At primary school (grade 6 and below) we would get this wide brim hats to be protected from the sun, during lunch time I would sit in the cafeteria or where other people were (literally with 100s of people and many teachers around me) and masturbate in the middle of everybody with only the hat over my dick being the only cover. no one ever noticed it (or at least no one ever mentioned it if they saw anything). I would do this like every lunch time for 6 months. this one time a girl, who I had this massive crush, came to talk to me because she would always see me sitting by myself (big fucking surprise I was a fucking loner), but at that moment I was in the middle of a wank, so I took my hand out from underneath the hat and had a conversation with her basically with my dick out and only covered by a hat.”
restlessly_injected


94. YouTube videos of women teaching how to play euphoniums and bassoons.

“Even though I’ve watched a lot of weird porn, what I’m most ashamed of is probably the YouTube videos of women teaching how to play euphoniums and bassoons.

I know they aren’t meant to be sexual, but there’s just something about a woman holding a big instrument and lecturing you about going down on it and covering all the holes… I’m sorry.”
sleif


95. I cut a hole in the ass of my teddy bear I had as a kid and fucked the stuffing out of it.

“I cut a hole in the ass of my teddy bear I had as a kid and fucked the stuffing out of it. I cried in shame as I threw it in the trash afterwards.”
nitemike


96. At the hospital while my nuts were watermelon-sized from being crushed by a horse.

“I had recently been crushed by my horse when he reared and lost his balance and the horn of the saddle landed on my nuts. I was taken to the hospital and my balls were literally swollen to the size of a watermelon. Here’s the other thing I’m gonna throw out there. I’m a rubber not a stroker, when I had the accident I was still rubbing my dick on soft blankets to cum. I was in so much pain the first time I went at it, I was rubbing my blue watermelon blood sack against a blanket. It got even worse when the blood hardened inside my nuts, it felt like a million daggers jabbing at my nuts when I’d do it.”
RenownedShark


97. I’ve fapped to the thought of getting pegged and pissed on by some rather unattractive triplets.

“I’ve fapped to the thought of getting pegged and pissed on by some rather unattractive triplets I knew in high school.”
LightningEdge756


98. God save me for what I did in a nun’s bathroom.

“I was 13, and working in Ft. Wayne, IN for my neighbor installing church pews. We were far from home, so the church had us stay in the convent while we were there.

The nun loaned me some movies to watch while I rested after work each day. One of the was That Thing You Do with Liv Tyler.

Turns out 13-year-old me had a crush on Liv Tyler.

God save me for what I did in a nun’s bathroom.”
Antyok


99. At church choir underneath my robe.

“I was in a choir for 5 years as a kid, not just a local church one, but a big one, went on tours and stuff like that.

Anyway, we wore robes and stuff which were quite loose, and 13-year-old me decided it would be a good idea to fap in them…in the middle of a morning service…in the middle of the choir seats.

Got away with it, totally worth going to hell for.”
IDLEJACK


100. A video from China about a dog getting boiled alive because a woman was making BDSM screams in the background.

“Once did the deed to a video from China about a dog getting boiled alive because there was a topless woman making BDSM type screams in the background.”
jackblackhappytimeTC mark

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