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

Versaillesxiv

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In high school gym class I stole a pair of underwear from the varsity football quarterback’s locker. He was the typical hot popular football guy, lean, defined muscles, handsome to look at. All the girls wanted him and all the guys wanted to be him. I was a freshman and he was a senior and we had the same gym period. My gym locker was just a few down from his and I was always checking him out as we were changing. He had a massive one too and wasn’t shy about it. One day I noticed he didn’t close his locker all the way before class started. Halfway through the class period I asked to go to the bathroom (back to the locker room). I checked to make sure no one else was in the locker room and went to his locker and opened it. All his regular clothes were in there along with his football uniform. I rummaged around and found the underwear he wore that day to school and smelled it. I got instantly rock hard and took out my dick. I jerked off and came all over his football jersey while I was sniffing his underwear. Then I put his underwear into my locker and went back to gym class. After class I watched to see if he noticed his underwear was gone, but he didn’t complain, he just put on his jeans without underwear and went on his day (so hot to know he went to school commando). I went to the football game that week and the only think I could think of was how he was getting tackled with my cum all over him. I still have his underwear to this day, 15 years later. I put them on and cum in them from time to time. He went on to play college football and he’s still sexy af and now in his mid-30s with a fiancé. Every time I see a photo of him on social media, my dick twitches a little thinking about what I did and how he never knew.
 
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I went round to a mate's flat yesterday afternoon; he lives across the road from me in a 1 bed flat. He's a couple of years younger than me & he's a fit scally lad type, he wears grey trackie/jogging bottoms & t-shirts a lot, he has a bit of a drink problem. A couple of minutes of going round he said he said he was just going to the shop at the end of the road to get some smokes. I was really horny & packing a proper boner. He went to the shop & I went into his bedroom & there was a pair of blue Ted Baker briefs on the floor. I took my cock out & started stroking it, I was already hard at this point, fuck I was horny. After stroking for about a minute I picked up the blue briefs & laid back on my mate's bed. I wrapped the briefs around my hard cock, completely covering it, fuck it felt good. I started jerking, thinking about my mate, fuck my heart was racing, I was thinking about sucking my mate's cock, making him moan. Fuck I was so horny, I felt my cock starting to tingle, I was about to cum, fuck it felt so good, I couldn't hold back. Fuck I was cumming & looked down at the briefs covering my cock seeing the cum oozing through the briefs. Fuuuuck it felt good, I blew a huge load. I slumped back on the bed & let out a heavy breath. I dried myself off with the briefs. I put the briefs back on the floor where I found them & moved the t-shirt over, slightly covering them. I zipped up my jeans & went back into the living & a couple of minutes later my mate came back. He offered me a smoke, I took it. We just relaxed watching the tv. I haven't heard anything from him yet so I don't know if he noticed the underwear, hopefully it's something I will get away with.
 

Stormcloud45

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I went round to a mate's flat yesterday afternoon; he lives across the road from me in a 1 bed flat. He's a couple of years younger than me & he's a fit scally lad type, he wears grey trackie/jogging bottoms & t-shirts a lot, he has a bit of a drink problem. A couple of minutes of going round he said he said he was just going to the shop at the end of the road to get some smokes. I was really horny & packing a proper boner. He went to the shop & I went into his bedroom & there was a pair of blue Ted Baker briefs on the floor. I took my cock out & started stroking it, I was already hard at this point, fuck I was horny. After stroking for about a minute I picked up the blue briefs & laid back on my mate's bed. I wrapped the briefs around my hard cock, completely covering it, fuck it felt good. I started jerking, thinking about my mate, fuck my heart was racing, I was thinking about sucking my mate's cock, making him moan. Fuck I was so horny, I felt my cock starting to tingle, I was about to cum, fuck it felt so good, I couldn't hold back. Fuck I was cumming & looked down at the briefs covering my cock seeing the cum oozing through the briefs. Fuuuuck it felt good, I blew a huge load. I slumped back on the bed & let out a heavy breath. I dried myself off with the briefs. I put the briefs back on the floor where I found them & moved the t-shirt over, slightly covering them. I zipped up my jeans & went back into the living & a couple of minutes later my mate came back. He offered me a smoke, I took it. We just relaxed watching the tv. I haven't heard anything from him yet so I don't know if he noticed the underwear, hopefully it's something I will get away with.
Fucking hot dude. Love a scally lad.
 

AlphaLion

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My friend who is an IFBB Pro Bodybuilder ended up staying with me over the weekend. He went to go to the gym and he showered and changed and left his suitcase open. I saw a pair of calvin undies sitting there and he's really attractive muscular and smelled sweet. So I started sniffing the cock/balls area and it smelled really clean and had to deep inhale to find his scent. I found it and started jerking off and blew a huge load and then put them back. I'm hard again just thinking about it but prolly shouldn't have done it.
 

herbho

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I used to go to a very small local bathhouse in town. One day, when I was checking in, I noticed that the attendant was much younger than the ones who had been at the front desk. I'd have put him in his early 20's. Looks-wise, he sort of resembled Sean Ford. Anyway, just off the small weight room, there was a tanning room, which had a door equipped with slats, so, if you were sitting on the floor, you could see into the room. I noticed that this attendant would occasionally use the tanning bed when there were few customers. Well, the temptation got to me. There was almost no one in the whole place and I was on the treadmill in the gym. Soon, that attendant, wearing only a towel, walked past me and went into the tanning room. I immediately got off the treadmill and went over an sat down on the floor, peering into the room. The attendant had just dropped his towel and in front of me was the most delicious, little tight ass I had seen in a while. He lifted up the lid of the machine, affording me a look at his cock from the side. He was about six inches, cut, with very little pubic hair. He sat down in the booth and put on his goggles, then lay down and pulled the top down. I had an unencumbered view of his cock and balls. I started entertaining myself and noticed that his dick started to move back and forth, getting a little harder. I heard a noise, so I stood up and walked over to the weights. When the person who made the noise passed, I went back to my position, just as he was getting out of the machine. it must have been exciting for him, because he was fully erect, and he was a grower ( a 45 degree grower). I went back to the treadmill when he walked past me with his towel tenting in front. He went to the shower, so I got in the hot tub to watch him in the shower. He did a thorough soaping of his body, including several soapy strokes down his erection. I was playing with myself in the water. He left, toweled off still erect, wrapped the towel around himself and left the room. I got out of the tub, used the same shower and furiously jacked off remembering where he had been just a minute before. As I was just about to cum, a guy walked out of the steam room and saw me at the very moment of orgasm. But, what could you do? He smiled and I nodded. I often was there when the young attendant would go into the tanning booth and I repeated my same actions. I hated it when they told me that he went back to college.
 

DFoster

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I got insanely horny one night, like cum without touching horny. Nobody was home, I went into my step sisters room (I know) got into her panty drawer, I sniffed them, put them in my mouth, and then I put them on, panties and bra. It was a thong too, I love the feeling of the string up my ass crack. I laid down on her bed, and jerked off furiously, it felt so good. I blew a huge load into her panties, like soaked them. I felt so bad afterwards, I threw it all away.
 

sdbg

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I had an insane attraction to a coworker when I was in my early 40s. He was a homophobic rugby player, so I knew nothing would ever happen. We became friends and would hang out after work to drink wine and smoke weed. One time he came by after stopping at his place to change. As a typical jock guy, he always wore white briefs, but this particular evening, he was sporting yellow boxers with olive green shorts (I saw the waistband). We started the evening with several bong hits of some tasty Indica that I had. While we were making food in the kitchen, he bumped into me in my one-ass kitchen. His dick pressed into my hip when we collided, and I became immediately flustered. He said "Sorry!" and we kept working on the food. (I chuckled to myself: "I'm not sorry at all!)

The meal was ready, we broke out a bottle of wine, and enjoyed. After dinner, we smoked a little more pot. He fell asleep on my living room floor on his back. He looked so cute and I could not help notice his dick was pointing down his right leg (He was about 5" limp). I could see the outline of the shaft and head of his penis through his olive shorts. I got next to him on the floor for a closer look. I was dying to touch it, but I knew that I couldn't do it unless I wanted to end our friendship. I was rock hard. I couldn't help myself. I touched my dick through my gym shorts and knew that I was seconds away from erupting. I gave it a few pulls and blasted right in my shorts.

It was one of those situations where I knew that I was flirting with danger. If he would have awoken with me next to him jerking, he would have been pissed, and it would not have ended well. I was too fired up to not finish the job. Afterward, I went into my bed and crashed. He never knew that I jerked inches away from him while gazing at his dick in his shorts.
 

Alanjenkhoe

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I jerk off sniffing my dad's underwear or spying on him in the shower. I also jerk off to pics of my cousins/uncles. Getting off while I imagine myself being their cum slut...
I always jerk off to my uncles and cousins
 

Ryan2017

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My mum having sex with a younger man whilst I was in bed upstairs. Woke up to the sound of her getting pounded, it sounded really good.

I pulled my shorts down and started wanking.
 

Dan259

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I once had a wank using my sleeping straight mate's sock with his cock in my mouth. I didn't move my mouth I just lifted his cock up so I could put my lips around it and tried to keep my head still as I jerked off into one of his socks. I must have got away with it as things were totally normal the next day. The icing on the cake was he wore that sock the next day when we went into town
 

AJ20

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I've used some sneaky photos of my roommate and his clothes before. The first were semi nudes he had deleted on his icloud that I could access from his iPod he left hanging around (not password protected) and just airdropped them to myself before deleting them again. Then he fell asleep a few times after taking a shower and left the door open with just a towel covering him. I didn't get to see everything but got some nice shots of him still, especially his big feet and hairy chest.
The holy grail though was when he had a girl over and had covered the dog camera I have in our living room. At some point the cover fell off so I got two short clips of him fully nude. I've used his musky underwear and socks before to jerk off but that night I got the nude videos I came harder than I ever have.
 

charlie59horse

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I'm glad I found this thread...
My freshman year in college I came home for the Thanksgiving holiday on Tuesday. When I arrived my Aunt and Uncle were there for the week. They had been married for just 5 years....she was my moms younger sister.
I went into the house and greeted everyone. Where is Uncle Larry? He is taking a bath...we didn't have a shower just a tub. Oh ok.
So I am talking to my mom and aunt when I hear my uncle yell to my aunt that my lil cousin Johnny who just started walking was in the bathroom. The bathroom door was not a regular door as it would slide open. Uncle forgot to lock it and john forced it open. My aunt tells me to go get him. In my head I was all excited because my uncle was taking a bath so he would be naked.
I entered and there is Johnny splashing by the tub and Larry is on his knees with water covering him from the waste down and full of bubbles. I grabbed Johnny and he fought me and Larry grabbed him and i picked him up. That's when Uncle Larry adjusted himself and I got to see his semi erect dick...it was long, uncut because the head was sticking out from the skin and had a beautiful bush. He didn't cover himself at all. He said thanks and I said no problem.
I went to the car and got some of my stuff down and told them I was going to my room. I closed the door, got on the bed, pulled my dick out and with my uncles image in my head I jerked off with gusto like I had never jerked off before. I came all over my hand and stomach. I ate every drop of cum pretending it was my uncles.
After this day I'd always see him in a different light. Ten years later they divorced...Larry moved out of State and we hardly hear from him. I would love to give him a divorced blow job.
I can still close my eyes and picture his great cock. Im thinking that his bush was the reason that I love a good bush on a guy.
I LOVE a thick bush on a guy!
 

johnweek1

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Oh this thread, haha. What did I jerk off to when I was younger to something I should not have? I am so ashamed and embarrassed! Horse porn. :confounded:

Both a guy fucking a mare, and a horse fucking a woman and she literally took it to a creampie. I am not even remotely close to being into bestiality, but the size of an actual horse cock is insane.. and the camera angels of that hung twink fucking that mare and how wet and juicy and the noises it's pussy was making...I can still hear those slushes and whooshes and slosh noises in my head. Dear lord for whatever reason, in that moment, I did awful, terrible things to my dick while watching those videos.

I have never felt so gross in my life after. It still haunts me. Like literally me than and still me today 20 or so years later:

star-wars-anakin-skywalker.gif
 

tnman

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Oh this thread, haha. What did I jerk off to when I was younger to something I should not have? I am so ashamed and embarrassed! Horse porn. :confounded:

Both a guy fucking a mare, and a horse fucking a woman and she literally took it to a creampie. I am not even remotely close to being into bestiality, but the size of an actual horse cock is insane.. and the camera angels of that hung twink fucking that mare and how wet and juicy and the noises it's pussy was making...I can still hear those slushes and whooshes and slosh noises in my head. Dear lord for whatever reason, in that moment, I did awful, terrible things to my dick while watching those videos.

I have never felt so gross in my life after. It still haunts me. Like literally me than and still me today 20 or so years later:

star-wars-anakin-skywalker.gif
That is sooooo fuckin funny! I am laughing my ass off right now but the truth is I have done the same lol