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

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this is something I regret, creepiest and most uncool thing I've done, it was in my early twenties when I was insanely horny and would wake myself up in the middle of the night stroking myself. One night this happened and without even thinking I sat up and looked out the window and saw that in the house across the street, a gorgeous, hairy, husky man was shirtless standing at his window. I watched him while I jerked off. I would never actively seek to do the "peeping tom" thing but this was like reflexive and in the middle of the night, i was stroking furiously and couldn't take my eyes off him. He must have seen me because ever since that night his blinds were drawn. I was really ashamed of that.
 
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this is something I regret, creepiest and most uncool thing I've done, it was in my early twenties when I was insanely horny and would wake myself up in the middle of the night stroking myself. One night this happened and without even thinking I sat up and looked out the window and saw that in the house across the street, a gorgeous, hairy, husky man was shirtless standing at his window. I watched him while I jerked off. I would never actively seek to do the "peeping tom" thing but this was like reflexive and in the middle of the night, i was stroking furiously and couldn't take my eyes off him. He must have seen me because ever since that night his blinds were drawn. I was really ashamed of that.
still horny like that at 36
 
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A "straight" (I'm still not convinced lol) friend of mine. I have written about him on here before. Anyways, there was a guy on Twitter in my sort of area who was posting local guys nudes.. I guess he was either a baiter or he knew girls that could get them.. Anyways, this guys nudes got posted, and I wanked to them ferociously for months. On one hand I was a little bit heartbroken that he had sent them :joy: but on the other hand I was so excited to see that his cock was just as big and thick as I had thought it was.
 
Would checking out some guy who was in the same year as me in High School, and a few classes, Facebook profile for any shirtless pictures? He was fit as fuck in High School and still is fucking hot. Had a few wanks looking at his Facebook shirtless pictures.
Done that to a few few former high school guys. Checked out their Facebook profiles, Instagram too.

Have a phone wank with a guy who had sent me a few pictures and short vids of some guys he had baited.
Looking at the pictures and watching the vids, wanking and saying a few things on the phone.
 
A few guys who follow me on Twitter, check out their Twitter media and Facebook, to see if they have any shirtless pictures.


Thought about a few footballers who are brothers. Thought about the brothers shirtless, naked and maybe doing a few things to each other in their bedroom or in a changing room. A team gangbang
 
once I came to the room drunk at night and my roommate was sleeping. I started jerking and played porn so that my roommate could hear it. he woke up and laughed but nothing more. we went to bed together for the last time. It went off. And in a few minutes I hear my roommate jerking. He was loud on purpose and you could hear him rubbing his dick. What should I do next? I'm afraid he would refuse to join or laugh.
 
once I came to the room drunk at night and my roommate was sleeping. I started jerking and played porn so that my roommate could hear it. he woke up and laughed but nothing more. we went to bed together for the last time. It went off. And in a few minutes I hear my roommate jerking. He was loud on purpose and you could hear him rubbing his dick. What should I do next? I'm afraid he would refuse to join or laugh.
Did your roommate have a big dick ?
 
Probably some ex coworkers who weren't hot at all, probably out of boredom or something else.
 
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watched a video of this guy getting his dick sucked and couldnt see the guy sucking his dick immediately---or see the guy getting sucked face until last minute when see the guy getting sucked smiling telling the cam he was about to cum--then he pointed it down to his dick and i see the person sucking his dick--and it was my nephew--- i jerked off to that video for months until i deleted it afraid someone else in family would grab my phone and see it
 
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watched a video of this guy getting his dick sucked and couldnt see the guy sucking his dick immediately---or see the guy getting sucked face until last minute when see the guy getting sucked smiling telling the cam he was about to cum--then he pointed it down to his dick and i see the person sucking his dick--and it was my nephew--- i jerked off to that video for months until i deleted it afraid someone else in family would grab my phone and see it
Another reason I’m fortunate to have gone through most of my life without cell phone cameras . The past 10-15 yrs though? no videos of me, that I know of, yet
 
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Another reason I’m fortunate to have gone through most of my life without cell phone cameras . The past 10-15 yrs though? no videos of me, that I know of, yet
I was recorded on vcr tape video recorder few times .. I didn’t care then.. not sure if the videos exist anymore .. haven’t seen them online any
 
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Another reason I’m fortunate to have gone through most of my life without cell phone cameras . The past 10-15 yrs though? no videos of me, that I know of, yet
I wished technology today was around when I was younger.. the shit I would have recorded would been awesome to watch again.. or watch what happened when I was too drunk or Sri ed to remember what happened hehe
 
Wouldn't say this is awful but a little embarassing. Mind you I was an active alcoholic at this point.

I took my car in for an oil change one day a little hungover, sober but cloudy. I was quickly pulled into reality when the guy who was the maintenance tech was a total stud. He was a thick country guy, deep accent, filled out his jumpsuit well, had it unbuttoned at the top that showed off some hair on his upper chest.

He was behind the counter and when he bent over to pick up something, I could clearly see a brief line hugging his ass and deduced he was only wearing UW under his jumpsuit. That did it. After handing them my keys I went to the mens room into a stall and jerked off thinking about him. I came pretty quickly.

Not the worst place in the world to do it but I'd never jerked off in a public space before then. He didn't take my payment or give me my keys back so no idea where he went. I also didn't see him the next time I took my car in, which was a shame.
 
Had a few pictures saved from a few guys via Badoo. Naked pictures. Had them and accidently deleted them. Saved a few pictures from Twitter and Facebook, the pics are a couple of guys who are low league football.


A few stuff that was sent to me via Wickr, deleted them after a month or 2. Legal stuff.
A guy that I've been talking to on Wickr. Telling me about himself and a few of his mates.What they have been doing. Not together.

Don't mind if something is dirty, within reason.
 
I still jerk off to a video of me slapping my ex’s fat ass. I kinda feel bad because I have a different boyfriend now but it’s so hot I just can’t bring myself to delete it. Sometimes I even fantasize about showing it to my boyfriend and him jerking off to it. And this part I actually feel really bad about but actually one time I had shared a screenshot of his ass in the video (no face or defining features) with some random person online and I got so horny thinking about someone else jerking to his ass that I came so hard afterwards. The thought of someone else jerking off to my current boyfriend’s ass makes me super horny too, never shared any of his pics though.
 
i was super horny in an amtrak train, and with the horniness lowering my intelligence for some reason I thought it would be really hot and fun and funny to just cum all over the restroom. So I jerked off in the restroom so turned on by the thought of my cum covering a public place. Right after I came, I was immediately like, "What have I done?" then nervously cleaned up what I could but it took so many paper towels that I had to wet and wipe and repeat until I could get it all off, though at first it just felt like I was spreading it when I was trying to clean it. Realized a whole bunch got on my pants too. God, what a total goon I was that morning.
 
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