What’s Something You’ve Masturbated To But Shouldn’t Have?

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deleted4741221

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I’ve “stumbled upon” the nudes of two different roommates over the years. The first was an actual physical photo album that my straight roommate’s girlfriend sent him to college with. Tons of pics of them naked, having sex, etc. I knew where he stored it so I took a look one day when I was alone in the room and cranked one out to a pic of his cock.

Fast forward to the second time. My gay roommate’s account was associated to our streaming device, which meant his photos were accessible. I knew he had plenty of nudes so I did some snooping. Hit the jackpot. I wanked to solo pics, jerk off and fuck vids a handful of times before I started to feel way too guilty and never looked again.
 

briacon429

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I’ve “stumbled upon” the nudes of two different roommates over the years. The first was an actual physical photo album that my straight roommate’s girlfriend sent him to college with. Tons of pics of them naked, having sex, etc. I knew where he stored it so I took a look one day when I was alone in the room and cranked one out to a pic of his cock.

Fast forward to the second time. My gay roommate’s account was associated to our streaming device, which meant his photos were accessible. I knew he had plenty of nudes so I did some snooping. Hit the jackpot. I wanked to solo pics, jerk off and fuck vids a handful of times before I started to feel way too guilty and never looked again.

Yum!!! When I was in college, one of the main dining rooms was directly across from the gym, and both buildings had plate glass windows. It was basically dinner theater: I got to sit there and watch a smorgasbord of hot guys right across from me!

I’m not sure if this meets your definition, but I’ve also fantasized about my share of guys I’ve been with. I fucking love imagining them banging away with somebody else... it doesn’t matter if they’re topping or bottoming, because it gets me off either way!
 

dante33

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A sex tape of my brother-in-law with his gf.
He's a gym trainer, so he has a smoking hot body. Nice dick and knew how to use it, as the chick was moaning like crazy and begging for more.
Video ended with him cumming all over her lower back.
Fucking hot.
 
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deleted3214101

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I used to sneak into my parents bedroom. I’d rummage around dads underwear drawers and try on pairs. My dick grew so fast feeling what he has felt on him. Countless times I jerked off wearing his underwear. Felt very guilty but continued anyhow lol
 
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deleted3214101

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I used to help at my dads car dealership growing up. I’d explore cars all by myself all the time in showroom. And for some reason lol I’d get hard and aroused and I remember stroking off in the cars. I knew people were watching me hop into the cars, but they didn’t know I was hard (maybe) fooling around with myself inside. I came several times doing this.
 

EvurHard7

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Over the years, I've definitely stolen a pair of some of my buddies' and roommates' dirty underwear and huffed on those while stroking.

I guess the thing that I have—and still—masturbate to but "shouldn't" would be fantasies I have involving my dad and brother.
 

Beanie

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I’m not sure about “shouldn’t have” because it makes me think of things I don’t want to.

however following the trend of the posts here already, I catfished a former colleague that I fancied for his nudes :rolleyes:
 

Jake88_

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I’ve “stumbled upon” the nudes of two different roommates over the years. The first was an actual physical photo album that my straight roommate’s girlfriend sent him to college with. Tons of pics of them naked, having sex, etc. I knew where he stored it so I took a look one day when I was alone in the room and cranked one out to a pic of his cock.

Fast forward to the second time. My gay roommate’s account was associated to our streaming device, which meant his photos were accessible. I knew he had plenty of nudes so I did some snooping. Hit the jackpot. I wanked to solo pics, jerk off and fuck vids a handful of times before I started to feel way too guilty and never looked again.
Hot!!!!
 

paulista_user

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A sex tape of my brother-in-law with his gf.
He's a gym trainer, so he has a smoking hot body. Nice dick and knew how to use it, as the chick was moaning like crazy and begging for more.
Video ended with him cumming all over her lower back.
Fucking hot.
Do you have any pic of your brother in law?

Where do you find the video?
 

MrAnonymousGuy

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I get off a lot to my bf's former roommate a lot. Like *A LOT.* More than I like to admit. He knows about it, and says it's fine because he also thinks his former roommate is hot. But he doesn't get it though haha. His roommate is ~18 years older than me and though he's older, he very young at heart and sorta bro-y but yet still so kind and friendly. For me, it's the idea that he's 18 years older than me. I love older men and I love how many girls he used to bring home to their apartment. My bf told me one time he went to the bathroom at like 4am, and he heard his roommate fucking a girl. That is just so hot to me. This older man, still gettin' it in with the ladies. Ugh I just melt everytime I see him. He's just so FOINE.