* In high school: masturbating in the girls’ locker room after school hours with a pair of panties i found hanging on an open locker door, and getting caught by a couple of jock guys who heard my high-pitched gasps and moans. They kind of made fun of me, though they weren’t as mean as i would have expected them to be. But they still told their friends, and word got around school about it.
* At a theater cast party: being in the hot tub with a girl i thought was really sexy (especially because she was wearing a yellow and black BodyGlove bikini in my favorite style, with the zipper down the front of the top). We had talked backstage during the performance run, talking about a lot of things (including a pregnancy scare she had), and we were flirting a bit. i had an insistent hard-on in my trunks, and at one point she sat in my lap while i was hard. i think she felt how small my penis was, because she grinned knowingly at me when she sat down, but then she said she saw a guy she wanted to talk to by himself and excused herself. i was so aroused that while i had the hot tub to myself i masturbated inside my trunks. It didn’t take me long to cum. i never did get anywhere with her after that.
* The first time i went to a strip club. i was working at a hospital, so i was wearing my scrubs, very thin material like pajamas, and i had panties on underneath. i picked out the girl i liked and got a lap dance from her. i think she could tell that i was wearing panties, though she didn’t say anything specific – it was all in her expression. Afterward i went out to my car and masturbated in the parking lot.
* Another party with a bunch of friends from the theatrical group. This time we were at a hotel in San Diego after the party. Everyone paired off together and started making out with each other, except for me. i went back to my room, stripped down to my panties and masturbated while thinking of the girls in the group. i considered calling an escort service, but chickened out. i knew with about 95% certainty that i was the only one who didn’t have sex that night.
* One of the first times i ever called for phone sex, i asked the girl to meow for me. i had been masturbating to furry pictures lately – thinking of catgirls specifically – and wanted to imagine the woman as a catgirl. She was confused and obviously had no idea why i was asking her to do it, but she did it for me, and made it sound incredibly sexy. i came pretty quickly. i’ll bet she still tells her friends about the weird pervert who got off to the sound of her meowing like a cat.
* Masturbating at the computer, with my shorts down around my ankles and sitting on a beach towel over the seat of a wooden kitchen table. i was living in an apartment with my brother at the time. The computer was on the kitchen table, so anyone walking in the door would see you. i heard a key fitting into the lock, and all i had time to do was reduce the browser window with my porn and wrap the towel around my waist. My brother’s girlfriend, a hot redhead, walked in and sat in the living room. She didn’t say anything to me, but just sat there for about 45 minutes, reading a magazine. She must have known what i was doing, especially if she noticed my shorts around my ankles, but she didn’t say anything about it. Finally she got up and went to the bathroom, and i was able to close the browser window and pull up my shorts. i went into my bedroom and masturbated in privacy, mostly to fantasies of what might have happened if she had decided to tease me. i had a LOT of fantasies about her…
Source: (25) what’s some of your most pathetic sessions? – Onania Masturbator Forum