This isn't my story but I once read on here that when some guy was a kid, he fapped to his moms attractive best friend one night right before bed. When he woke up, his mom was crying and told him that she had committed suicide last night. He said that one still haunts him today.
I was maybe 14, and my older brother had a palm pilot, I doodled a little stick figure with big breasts on it.
Yup, ill never forget
I fapped in the bathroom of the Vatican.
There's a video on pornhub, where some girl in a pink top is obviously not enjoying it. I assume the wiener is too big, and she's holding back tears. But she has an amazing butt. Then at the end, she swallows "him" and the dude asks, "You like that?" and while she's wiping away tears, she kinda mumbles, "Mmm... Yummy..." Almost made me want to cry. Still fapped.
I worked at a concession stand when I was a teenager, and one of our events was a week long German music fest. During the weekdays it would usually be dead. I was probably 14 or 15 and found myself applying dolphin wax in a porta potty that had been sitting in the August sunshine all day.
Another time when I was a teen I was experimenting with lotions to use. My mother and sisters had various skin lotions around the bathroom with various fragrances. Unfortunately I chose the lotion that was meant for exfoliating skin. I've never immediately regretted being born like I did that moment.
I was 14 when I went with my friend to his aunts beach condo. His aunt isn't necessarily attractive but the movement of water over my hormonal, pubescent junk coupled with his aunt in a bikini got me raging a serious stiffy. Not wanting to embarrass myself by walking around with a boner, I did the only thing I could do by asking my friend to throw me a towel while I was still waist deep in water, wrapped it around myself and booked it to the condo. Hopped in the shower and spanked it while thinking about his aunt in her bikini. I regret nothing.
Fapped in my grandma's bed.
I was so stressed out at her wake, I just slipped away from the party to burn off some steam.
Caught fapping in the bathroom by my gf while thinking about her Mom while we were visiting her parents one evening. She got aroused because my gf assumed it was her I was fapping too, so she decided to "help me out". And she certainly did because she looked quite a bit like her Mother.
A couple of nuclear generating stations that sort of looked like boobs
Shameful? At the old Giants stadium during a Jets/Giants game. Upper deck. Nobody was really there. I was 13.
Step aside boys, I've been saving this one. Last year on my ex girlfriend's birthday I decided to rip it and grip it to an old voice mail she had left me of her singing the Moon song by Karen O. https://youtu.be/SU6KFnGF9M8
. I decided to add to the realism of it by dimming the lights and dawning a condom for my little hard working helmet man. After a brief and unsatisfying finish I had a quick cry followed by a nap. When I woke up I knew it was time to move on. Silver linings I guess.
There was a dude at a theatre I managed for a while who had gone into a kid's movie and started beating it in the back row. Apparently no one noticed until he finished. Upon completion his load traveled like a heat seeking missile and found the cheek of a mother who was with her husband and two kids. Apparently it was just the right consistency to grab on, stretch out and wrap around to her face when it hit. The guy high tailed it out the nearest emergency exit and I didn't hear about it until the lady and her husband came to complain about it. Of course there was not much I could do at that point.
I was more ashamed of that guy's fap that any I've ever had.
When I was 13-14ish, I searched my sister's webcam folder and saw photos of her tits...
I was 13, okay? I was so horny I would fuck my own ass if I could and my ethical judgement was not exactly pristine.
Was on a family vacation for a week on the way home put a blanket over myself and went to town while my grandmother was sitting 2ft from me.
I bunked my high-school's compulsory prayers in the hall synogogue and sneaked into the big school lecture theater where in the dark I fapped...as everyone else prayed..on a public sushion seat. Not my proudest moment
I was at a "ministry development training" camp when I was about 14 and at the end they put you on an island for 6 hours alone to be "with Jesus" so I took a nap.
Lost track of time started wandering around and found a knot in a tree that kinda looked like a vag so I shot some ropers of holy spirit onto it and afterward ate a very shameful peanut butter sandwich