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

[deleted4741221]

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.

 

[indyfrat79]

My step dad's jock strap after he'd go to the gym. I still remember the smell.

 

[Lee_asian_091]

I was very close with my best friend, we were sooooo close. We used to spend a lot of time together, almost 24/7. He had a girlfriend but he didn't mind me stroking his hair or kissed his forehead. I had a HUGE crush on him. One day I was in his room, using his computer while he was off to the college.
I noticed that he hasn't put his clothes to his drawer. So, I wanted to that for him..

When I opened the drawer, I found an unfolded underwear, so I thought let me fold that. When I took out that underwear I found his wet cum on it, needless to say I lick it, smell it and jerk off to it.
I even cum on it.. I felt really bad afterwards but it was such a huge turnon for me I couldn't control myself then.

 

[swordfishME]

My old straight college roommate. Dump truck ass. I used to tell him how hot he was and how horny it made me. One day I was moaning about not having jerked off in a while because of a lack of mental stimulation. He told me that if I agreed to stay on my side of the room, he’d strip naked and go about his (non-sexual) business and I could jackoff to him. He told me it was a one off and to take good mental pictures and true to his word it never happened again

 

[dante33]

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.

 

[deleted3214101]

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

 

[EvurHard7]

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.

 

[Versaillesxiv]

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.

 

[freeurmind7]

a family members jo video

 

[4202HHN]

Listening to my dad fucking his girlfriends. I was an adult, btw.

It was never intentional so I didn’t intend to get a huge stiff dick, but what’s a fellow to do when Pop is a tall, beefy Marine Corps vet with a dick as big as mine?

 

[HorseHung40's]

I make NO apologies for my sex drive or sexuality - EVER.

 

[Uknowuloveme]

I'm addicted to straight White Buddy to White buddy oral sex "overheated" sex blow job instructing car sex or any location/gloryhole oral sex footage or Rogan Hardy interracial oral sex vids.
ADDICTED TO HOOVERMOUTH OF XVIDEOS FOOTAGE OF ANONYMOUS STRAIGHT GUYS BLOWING THEIR LOADS!

 

[korewamizu]

i video of my dad jerking off

 

[cedarizzo]

my boyfriends brother :S

I used to have the biggest crush on my 1st boyfriend's younger brother. My boyfriend knew about my crush on his brother and often kidded me about it. One year, we bought a video camera at Christmas. I didn't realize how bad my crush was on his brother until I watched the video of Christmas day. Each time I used the camera, his brother was part of it. I jacked off more than a few times to the part where his brother woke up and came downstairs in nothing more than a pair of boxers that showed a nice half-hard package.

 

[minstagram]

saw my dad jerking so many times... spy him in the shower, sniff and lick his underwear...all of it.. hundreds of times LOL

 

[deleted3214101]

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.

 

[herbho]

When I had one of my first apartments, the walls were thin and I could hear a lot of what was happening in the next apt. Now that I'm older, I hate that, but that's all I could afford at that time. My neighbor was a young man just starting his first job, so he was enthusiastic about just living life on his own. He did have a boyfriend who would come over periodically. When I heard them, I knew that I was going to have a very good evening, because they were going to have sex and his bedroom and mine were right next to each other. Well, I prepared myself and, inevitably the lovemaking would start. I felt weird, but I tried the old glass against the wall and it worked. I could hear much of what they were saying, all of the sex talk and how this and that felt. When it came to the fucking, my neighbor was the bottom and, to say the least, he was very vocal, since his boyfriend was a very physical fucker. I heard the rhythm of the bed and the screams of ecstasy from my neighbor. Of course, all this time I was jacking off and trying to hold back so we could all come together. I usually was so turned on, I came before the boyfriend, but once in a while it was pretty close. I still remember it fondly and always looked at my neighbor differently. I'm sure he knew that I could hear the fucking, but we never spoke about it. Now, if someone next door was noisy during sex, I would probably be annoyed, since it would interfere with my sleep. But back then, it was enjoyable, because it was a bit dirty, listening in on something so private.

BTW, I reciprocated by making sure I was a bit loud and talked dirty as I was getting plowed on my side of the wall, so, if he did the same thing as I did while listening to the sex sessions, he could hear my cries and then he might have as good a night as I did every time I listened to him.

 

[herbho]

Years ago I went to a masseur who had an office in an old downtown building. The place consisted of a waiting room and a massage room, separated by a door. I would go in the evening when the building was deserted, yet he was open. I used to arrive a few minutes early for my 8pm appt and sit in the waiting room, which was just illuminated by a single low wattage bulb. This masseur would invariably leave the door to the massage room open a crack so he could hear those arriving, so I was always very quiet. Of course, being the voyeur I am, I used to sneak over to the crack in the door, open in slightly more, and watch him give massages. The first time was a man in his thirties, who was lying totally naked face up on the table. His face was covered and the table was situated so that the masseur's back was to me, so I was safe. I committed to memory the look of his genitals and went home and jacked off. But, one day, I peeked in and on the table was a college student whom I used to employ during the summer and on vacation to do yard work. I always lusted after his cute little ass. Anyway, he was on the table naked with a very large erection. I was in heaven, as the masseur was working on the groin area. He wasn't giving him a handjob, but was massaging all around, making his erection away back and forth. Well, I couldn't take it anymore. I whipped out my dick and started entertaining myself right there. Unfortunately, the massage ended much too soon for me, so I zipped up and sat down in the waiting room. The kid came out and we spoke for a few minutes. Then it was my turn in the massage room. I was so turned on that I was hard the moment I got naked. The masseur just said to me, " You know him? Cute kid, big dick. I saw that you enjoyed the show." I never knew that he knew I was watching, which made me even harder. I went home, pictured the naked massage I had seen, and unloaded a huge load.

 

[deleted17561691]

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.

 

[johnweek1]

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.

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: