People Reveal The Most Shameful Things They’ve Ever Masturbated To

Kids today have it so easy with the internet and all of the X-rated bounty it has to offer. Back in my day *puts on reading glasses* if a guy wanted to get his rocks off, he’d have to use a stiff-as-cardboard dirty magazine his friend found in an alley which had subsequently been passed around to half the kids at school, or pause just at the right time during a nude scene in a movie you taped off HBO.

This probably explains a lot of these answers on this recent AskReddit thread, which poses the question: “What is the most shameful thing you have ever masturbated to?” — but not all of them. While necessity is indeed the mother of invention, some of these answers were just plain inspired, and as such here are some of our favorites.


Strip club in [San Andreas] Grand Theft Auto when I was young. It was called The Pig Pen and I knew how to drive there without looking at the map. Pretty sad.

Digital strippers at a place called “The Pig Pen” must have been naaaaaasty. I approve.


Fantasy of my friend’s not hot bbw mom giving me a blowjob. I jerked off to this while on his couch. While pretending to be asleep. In a room with him and 6 of our friends. At his birthday sleepover.

Gonna go ahead and guess that’s a throwaway account.


Sigh….MTV’s “The Grind” I used to record it and play a game of “dont blam when the dudes are in focus.”

This is EXACTLY the point I was making above.


A ceiling titty

Note: this is what a ceiling titty is, for the uninformed.


The robot titty in the Leprechaun movie. It was the first or second, can’t remember now.

Wasn’t Jennifer Aniston in that? Come on, now.


An extra curvy piece of driftwood.



pictures of a girl I dated who I really, really liked. Only 1 dirty pic, the rest are pics of her trying on outfits, or nice hair day pics, or whatever random pics girls take and send to their s/o’s. I always cry after. I don’t know why I do this to myself. No wait, it’s because I hate myself.

Not sure what’s sadder. That, or smileedude’s contribution:

My wife’s facebook profile picture when I missed her.


My cousin.

It was me, my aunt and uncle, my cousin and our grandparents one summer at the beach-house. It was nice and warm, and we were sitting quietly in the living room, when she came out of her room in a clingy tank-top and athletic shorts — a fetish of mine — a size too small. She flops onto the couch by the window and sprawls out in the sun.

I couldn’t get rid of the resulting boner, so I had to pop into the downstairs bathroom and rub one out.



Jewish concentration camp movies on network t.v. I would always get a thrill when I knew one was coming on because they always have a “shower scene” where everyone has to get naked. Since it was historical the networks would relax their standards. So that meant I got to see naked people and jerk off to it later.


I have an irrational hatred of birds. There’s a video of a woodpecker eating some mourning dove baby-chick brains. But like, it pecks the heads a bunch and the chicks just sit there and get their brain juices sipped out. Just this one single video, and now when I hear mourning doves I feel a twinge of guilt in my heart and a twang of boner in my pants.

I stand corrected!

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