What's your best jerk off memory?

Fuck, for me it was this one night at a “friend’s” house. My wife and I went over for drinks and she instantly locked onto one of there older work buddies. She was all over him flirting, touching his arm, laughing at everything he said, the whole bit.

Halfway through the night she snuck off with him to the kitchen for “another drink.” I waited a bit then quietly moved closer. I heard him growl, “You’re such a naughty little slut, aren’t you?” and my wife moaned softly and answered, “Yes… I’m your naughty slut tonight.”

They started making out like animals loud, sloppy, tongue-fucking kisses, her moaning into his mouth like a bitch in heat. I peeked around the corner and watched him roughly shove his hand up her dress, yanking her g-string aside and jamming two thick fingers deep into her dripping cunt while he grabbed her tits. She was grinding her soaked pussy on his hand like so hard and desperate, stroking his rock-hard cock through his pants and whimpering every time he would push his fingers deeper!

This went on for about 5 minutes before he started finger-fucking her faster and harder, while growling filthy ...... in her ear. My wife’s legs started shaking, her moans got louder and sluttier, and suddenly she came like a filthy whore, gushing all over his hand, while she bit her lip trying (and failing) to stay quiet. He kept pumping his fingers through her orgasm, smearing her cum all over her thighs and calling her a “his slut” the whole time. She was a dripping, trembling mess.

Meanwhile I stood there in the hallway , furiously rubbing my cock while another man made my wife cum on his fingers like a cheap whore in our “friends” kitchen.
 
Mine was back when my wife and I were separated. I hooked up with this chick for a one night stand and we were at her house. She was really hot.

We were supposed to have the house to ourselves for the night, however about ten minutes inside her and her mom dropped her ...... back off unexpectedly. So of course we had to stop.

We would start again, then he would wake up sick every time in the other room. Finally in the sixth time it was 7:00 in the morning, so I left. Extremely frustrated.

I get home and I barely sit my stuff down and my covk is out. I came about 5 minutes later and this was the granddaddy of edging. I literally shot my load across the room.
 
It was during my wife's first outings with another man, alone, without husband's company.

I ( husband) was traveling and received some very improvised photos of her sitting on the guy's dick in his own room.

The materialization of what I had always imagined she was capable of doing in my back, made me masturbate and cum deeply. Maybe some of the hottest orgasms I've ever had.


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When I used to listen to my roommate railing S back in college. Spying on them when they didn’t know that I knew made it so much hotter for me.
She was so loud and so multiorgasmic with him.
So many of my "jerk off memories" are from our early 20s when she was still in college. So many crazy house parties we went to where so many sexual things went down and so many first times. A lot of emotions during that time.
 
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Hot. How did you feel having his balls dragging across you face? Did you kiss and lick them? What did they smell like? When I was in that position I loved it. Kissed and licked his balls too.
I felt so weird. He had massive balls hanging low. His cock was huge. He was very clean. I kicked his cock as it went in and out of her
 
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Best jerk off memory...
Years ago, I was just starting college. Went to a nearby nude beach about 30 min from my house. It was a Saturday about 11. Everyone knew about this place but it was my first time. I paid the fifty cents to park then walked the maybe ½ mile trail down to the beach. Beach was not crowded at all. I put my towel down and sat in my shorts. People started showing up. I'd never seen that many naked people. Most were older, 40s 50s. Several male gay couples a few single guys but mostly couples.
This older couple 45-ish asked if they could sit near me, it was getting crowded, beach wasn't all that big. They were super cool and friendly. We chatted about how far we drove, the weather, how cold the water was, etc.
She took off her shirt and had nice tits. He slipped off his shorts then she did same. I didn't want to look like a tard so I took off my shorts. I got hard instantly, I sat there with my knees against my chest. We continued to visit, my dick went down pretty quick.
They were so chill, offered me a coke and some chips. It was pretty relaxing. They were sitting kinda across and in front of me. She moved to sitting indian style, her pussy was in full view and about 4 feet away. We were taking about my classes. I kept looking at her puss and I got full hard. The husband said it's no big deal and not to worry and just don't walk around like that. It went down in about a minute.
Lots of people were walking ankle deep in the water. My friends asked I wanted to try the water, he said they walk around and watch people. We walked the 2 minutes to the end of the beach and they showed me where people go p.e,e in the wet sand at waters edge. Guys stand facing the rocks and wizz into the sand. He did then I did then his wife just squatted and pe.e.d right next to me like it was nothing. We stood there for a minute looking out at the ocean. Another couple walked over and did same thing. It was secluded from others seeing, maybe 10 people could fit back there, it wasn't big. I had a pretty good semi going on for a min.
We walked back to our spot and just chatted. They were so cool.
A bit later we all walked to the other end of the beach, another pretty secluded place about same as bathroom spot. He explained this is where couples might go for a little fun. This couple showed up, hugged and kissed then she leaned against a big rock and he slid into her and fucked her. While they were doing it a gay couple arrived and one guy started sucking his friend. I was friggin rock hard as was my friend. His wife stroked his dick. The couple, he let it go in his girl, she squatted in the shallow water and splashed herself off. The gay guys he swallowed it then they walked off. I couldn't believe what was going on.
We started to walk back to our spot, he was about half hard I was full hard. We got to our spot, sat down and talked like nothing happened.
They were both in good shape, she had nice natural tits that sagged just right, he had a big dick.
They said they had to leave, we stood up, he and I shook hands, she hugged me tight with her tits against my chest and her stomach against dick.
They left and I went home soon after.
At home I got in the shower and beat off like normal but I shot the biggest load ever, it slammed against the shower wall.
I jacked off to that for years.
 
Best jerk off memory...
Years ago, I was just starting college. Went to a nearby nude beach about 30 min from my house. It was a Saturday about 11. Everyone knew about this place but it was my first time. I paid the fifty cents to park then walked the maybe ½ mile trail down to the beach. Beach was not crowded at all. I put my towel down and sat in my shorts. People started showing up. I'd never seen that many naked people. Most were older, 40s 50s. Several male gay couples a few single guys but mostly couples.
This older couple 45-ish asked if they could sit near me, it was getting crowded, beach wasn't all that big. They were super cool and friendly. We chatted about how far we drove, the weather, how cold the water was, etc.
She took off her shirt and had nice tits. He slipped off his shorts then she did same. I didn't want to look like a tard so I took off my shorts. I got hard instantly, I sat there with my knees against my chest. We continued to visit, my dick went down pretty quick.
They were so chill, offered me a coke and some chips. It was pretty relaxing. They were sitting kinda across and in front of me. She moved to sitting indian style, her pussy was in full view and about 4 feet away. We were taking about my classes. I kept looking at her puss and I got full hard. The husband said it's no big deal and not to worry and just don't walk around like that. It went down in about a minute.
Lots of people were walking ankle deep in the water. My friends asked I wanted to try the water, he said they walk around and watch people. We walked the 2 minutes to the end of the beach and they showed me where people go p.e,e in the wet sand at waters edge. Guys stand facing the rocks and wizz into the sand. He did then I did then his wife just squatted and pe.e.d right next to me like it was nothing. We stood there for a minute looking out at the ocean. Another couple walked over and did same thing. It was secluded from others seeing, maybe 10 people could fit back there, it wasn't big. I had a pretty good semi going on for a min.
We walked back to our spot and just chatted. They were so cool.
A bit later we all walked to the other end of the beach, another pretty secluded place about same as bathroom spot. He explained this is where couples might go for a little fun. This couple showed up, hugged and kissed then she leaned against a big rock and he slid into her and fucked her. While they were doing it a gay couple arrived and one guy started sucking his friend. I was friggin rock hard as was my friend. His wife stroked his dick. The couple, he let it go in his girl, she squatted in the shallow water and splashed herself off. The gay guys he swallowed it then they walked off. I couldn't believe what was going on.
We started to walk back to our spot, he was about half hard I was full hard. We got to our spot, sat down and talked like nothing happened.
They were both in good shape, she had nice natural tits that sagged just right, he had a big dick.
They said they had to leave, we stood up, he and I shook hands, she hugged me tight with her tits against my chest and her stomach against dick.
They left and I went home soon after.
At home I got in the shower and beat off like normal but I shot the biggest load ever, it slammed against the shower wall.
I jacked off to that for years.
I can understand why, a first time thing with a nice unfu cked up couple. I suspect the guy sucking cock may have something to do with it too. Do you think of that when jerking off? Very liberating too.
 
Although I'm turned on by reading all these exciting stories, mine may seem a little tame by comparison, but I do fondly remember my 'best' jerk off memory, and often wish I could relive it.

Growing up, I was typically tall for my age, and a little chubby, but I did a lot of sports, so I was in decent shape and somewhat flexible with all the constant stretching and exercises. As a teenager, I was horny as fuck, but between school (all boys Catholic high school), homework, sports, commuting, and church (and lacking a car), I didn't have much opportunity to meet girls, no matter how horny I was. I remember being awake after midnight, just horny as hell, stroking my member, fantasizing that some gorgeous babe would crawl through my window at night and my parents would be away (since my bedroom was next to theirs, and my bed was against the common wall). I had had a stash of a few girly mags, Playboys, Penthouses, Hustlers (this was before the internet (as we know it) or the world wide web). Sometimes, if my parents were out and I was alone, I'd sneak into my parents' bedroom and look for hidden mags my dad occasionally kept. Usually it was a somewhat tame Playboy, the first one I ever found I was in third grade and I found a 20th anniversary issue (two bunnies on the cover with a black background) snuck into one of the pockets of his business briefcase. One of the best memories was finding my first hardcore mag under my dad's mattress. It looked like it was from the late sixties or early seventies... It had a color cover and the last half was color but the first half was black and white. It was about this guy living in a boat watching these two girls (one in a black bikini, the other in white) sunbathing on the adjacent boat. Sure enough, while applying suntan lotion on each other, they start 'exploring' each other. The first picture I saw of any penetration was one girl inserting her single finger into her friend's pussy. After watching them finish sunbathing, he goes over, introduces himself, and invites them over for drinks, which of course ends up in a threesome. The guy was in good shape, blonde, but middle-aged and balding... The girls were young (college aged), thin and cute, not flat chested (Thank God, not into that), but not particularly stacked (which I was developing a taste for)... Both about a C-cup, one a mid-C, the other barely a C, maybe a B. My dad obviously either hid it better or threw it away, but I only saw it a few times before it was gone. The cover was framed in yellow and green, and I believe the title was in yellow, and stylized... The first letter had one or two loops, so I thought it was titled "Just Aloat", but after thinking about it and seeing similar letters, I realized the title was actually "Lust Afloat", and I've been looking for a copy or scan of this magazine for decades. Between that and hiding one or two of my girly mags in one of our bathrooms (one of the few places I had privacy), I'd be stroking on the toilet or in the shower. Despite my self-induced blue balls from all the constant stroking/edging, it wasn't until I was 14 that I finally came, for the first time, in the shower. Since I was in pretty decent shape and flexible, despite being slightly chubby, I was curious about what it'd be like to have a blowjob (or maybe even give one)... Even to this day I've fantasized about it, but never have... I love women, and am not even remotely interested is guys as anything other than friends, but there's something about seeing an engorged, throbbing cock, and full, low hanging balls that gets me excited, especially seeing those veins popping and precum dribbling from the tip before a torrent, a fountain of cum jets forth. Being young and in shape, my cock was ~7-9 inches, depending upon how you measured it (from my balls or my stomach), and thick, but not Blake Palmer thick/girth. Sometimes I'd make sure the door was closed, get in the hot shower and lay in the tub, stroking... One day I decided to turn around with my head under the faucet and feet against the back... I noticed that it felt slightly different and I could see my cock slightly better... I began to wonder so I tried something different... I began to scoot my ass up the tub with my feet on the back wall... Soon my head was still on the bottom of the tub, my back against the back of the tub and the back wall, and my feet high on the wall... I had a much better view of my cock, now, but it was in an awkward position... But it was about to get more awkward... I lifted my legs (or, better described, let them fall) over my head... Where I was facing my own cock... Given the position, I wasn't exactly positioned to stroke myself, and it was difficult to breathe, but it was exciting... My cock was engorged, although at a strange angle, and with effort I was able to just barely get the tip to my lips... I couldn't quite get it fully in my mouth, but I do remember tasting my own precum and once or twice sucking out some of my own come... Sometimes I wondered what it would be like to be sucking my own cock, in that position while having some babe licking my balls or even some guy burying his cock in my ass. Unfortunately, I could never take too long exploring this position, because, inevitably my father would bang on the bathroom door (or even unlock it and come in) getting made at me for taking such long showers and using all the hot water (as if he didn't know that I was jerking off). After being in the military and going off to college, I kept the same diet, but my metabolism slowed as I got older, spending more time sitting, attending lectures, studying, playing computer games. I got chubbier and fatter... And, unfortunately, less flexible and a fatter stomach and less cock pas my fat. I'm starting to lose weight again, but nowhere near what I was when I was still able to put my cock between my lips. I remember decades later, my wife got me watching this U.S.A. network show about these two plastic surgeons that were in business together (friends? brothers? ... It's been so long ago), called "Nip/Tuck". One is an ethical surgeon who occasionally does pro bono surgeries for disfigurement, and typically does surgeries to help those needing some quality of life help, while the other is the most base, crass horn dog who specializes in vanity surgeries and goes through girlfriends every episode, nothing more than boob jobs, face lifts, liposuction, implants, penis extensions, etc. I remember there was a few episodes where the crass one heard about a client (?) who had such a unit he could suck his own cock... I don't know if he did it the same way, but... The crass doctor, who was in decent shape, but older (40's?) and obviously not as flexible, tried it himself, unsuccessfully, and ended up with a neck injury, having to wear a neck brace for at least an episode or two.

I do miss that, and sometimes wish I could do it again... But I know that I'm out of shape, not nearly as flexible, and just too fat to seriously consider that... although I am losing weight, so, who knows... if I lose enough weight with diet and exercise, and enough stretching to improve my flexibility, maybe... just maybe... I love my beautiful, busty BBW wife, but her libido is practically dead (at least around me), and it's frustrating, as half the time I see her walking around and I just want to run over, rip her clothes off and ravage her until she can't cum anymore...

Sorry it it was vanilla, but just thought that I'd share...
 

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When my wife and I went to a swinger's party at Judy's house, and at some point in the afternoon I walked into a room, and my wife was riding a guy, cowgirl, and her eyes were closed tight, and her head was swinging from side to side like Stevie Wonder, and she had this big goofy grin, and she was just saying over and over "I'm cumming ... I'm cumming, Jack ... I don't even know his name, and I'm cumming."
 
Although I'm turned on by reading all these exciting stories, mine may seem a little tame by comparison, but I do fondly remember my 'best' jerk off memory, and often wish I could relive it.

Growing up, I was typically tall for my age, and a little chubby, but I did a lot of sports, so I was in decent shape and somewhat flexible with all the constant stretching and exercises. As a teenager, I was horny as fuck, but between school (all boys Catholic high school), homework, sports, commuting, and church (and lacking a car), I didn't have much opportunity to meet girls, no matter how horny I was. I remember being awake after midnight, just horny as hell, stroking my member, fantasizing that some gorgeous babe would crawl through my window at night and my parents would be away (since my bedroom was next to theirs, and my bed was against the common wall). I had had a stash of a few girly mags, Playboys, Penthouses, Hustlers (this was before the internet (as we know it) or the world wide web). Sometimes, if my parents were out and I was alone, I'd sneak into my parents' bedroom and look for hidden mags my dad occasionally kept. Usually it was a somewhat tame Playboy, the first one I ever found I was in third grade and I found a 20th anniversary issue (two bunnies on the cover with a black background) snuck into one of the pockets of his business briefcase. One of the best memories was finding my first hardcore mag under my dad's mattress. It looked like it was from the late sixties or early seventies... It had a color cover and the last half was color but the first half was black and white. It was about this guy living in a boat watching these two girls (one in a black bikini, the other in white) sunbathing on the adjacent boat. Sure enough, while applying suntan lotion on each other, they start 'exploring' each other. The first picture I saw of any penetration was one girl inserting her single finger into her friend's pussy. After watching them finish sunbathing, he goes over, introduces himself, and invites them over for drinks, which of course ends up in a threesome. The guy was in good shape, blonde, but middle-aged and balding... The girls were young (college aged), thin and cute, not flat chested (Thank God, not into that), but not particularly stacked (which I was developing a taste for)... Both about a C-cup, one a mid-C, the other barely a C, maybe a B. My dad obviously either hid it better or threw it away, but I only saw it a few times before it was gone. The cover was framed in yellow and green, and I believe the title was in yellow, and stylized... The first letter had one or two loops, so I thought it was titled "Just Aloat", but after thinking about it and seeing similar letters, I realized the title was actually "Lust Afloat", and I've been looking for a copy or scan of this magazine for decades. Between that and hiding one or two of my girly mags in one of our bathrooms (one of the few places I had privacy), I'd be stroking on the toilet or in the shower. Despite my self-induced blue balls from all the constant stroking/edging, it wasn't until I was 14 that I finally came, for the first time, in the shower. Since I was in pretty decent shape and flexible, despite being slightly chubby, I was curious about what it'd be like to have a blowjob (or maybe even give one)... Even to this day I've fantasized about it, but never have... I love women, and am not even remotely interested is guys as anything other than friends, but there's something about seeing an engorged, throbbing cock, and full, low hanging balls that gets me excited, especially seeing those veins popping and precum dribbling from the tip before a torrent, a fountain of cum jets forth. Being young and in shape, my cock was ~7-9 inches, depending upon how you measured it (from my balls or my stomach), and thick, but not Blake Palmer thick/girth. Sometimes I'd make sure the door was closed, get in the hot shower and lay in the tub, stroking... One day I decided to turn around with my head under the faucet and feet against the back... I noticed that it felt slightly different and I could see my cock slightly better... I began to wonder so I tried something different... I began to scoot my ass up the tub with my feet on the back wall... Soon my head was still on the bottom of the tub, my back against the back of the tub and the back wall, and my feet high on the wall... I had a much better view of my cock, now, but it was in an awkward position... But it was about to get more awkward... I lifted my legs (or, better described, let them fall) over my head... Where I was facing my own cock... Given the position, I wasn't exactly positioned to stroke myself, and it was difficult to breathe, but it was exciting... My cock was engorged, although at a strange angle, and with effort I was able to just barely get the tip to my lips... I couldn't quite get it fully in my mouth, but I do remember tasting my own precum and once or twice sucking out some of my own come... Sometimes I wondered what it would be like to be sucking my own cock, in that position while having some babe licking my balls or even some guy burying his cock in my ass. Unfortunately, I could never take too long exploring this position, because, inevitably my father would bang on the bathroom door (or even unlock it and come in) getting made at me for taking such long showers and using all the hot water (as if he didn't know that I was jerking off). After being in the military and going off to college, I kept the same diet, but my metabolism slowed as I got older, spending more time sitting, attending lectures, studying, playing computer games. I got chubbier and fatter... And, unfortunately, less flexible and a fatter stomach and less cock pas my fat. I'm starting to lose weight again, but nowhere near what I was when I was still able to put my cock between my lips. I remember decades later, my wife got me watching this U.S.A. network show about these two plastic surgeons that were in business together (friends? brothers? ... It's been so long ago), called "Nip/Tuck". One is an ethical surgeon who occasionally does pro bono surgeries for disfigurement, and typically does surgeries to help those needing some quality of life help, while the other is the most base, crass horn dog who specializes in vanity surgeries and goes through girlfriends every episode, nothing more than boob jobs, face lifts, liposuction, implants, penis extensions, etc. I remember there was a few episodes where the crass one heard about a client (?) who had such a unit he could suck his own cock... I don't know if he did it the same way, but... The crass doctor, who was in decent shape, but older (40's?) and obviously not as flexible, tried it himself, unsuccessfully, and ended up with a neck injury, having to wear a neck brace for at least an episode or two.

I do miss that, and sometimes wish I could do it again... But I know that I'm out of shape, not nearly as flexible, and just too fat to seriously consider that... although I am losing weight, so, who knows... if I lose enough weight with diet and exercise, and enough stretching to improve my flexibility, maybe... just maybe... I love my beautiful, busty BBW wife, but her libido is practically dead (at least around me), and it's frustrating, as half the time I see her walking around and I just want to run over, rip her clothes off and ravage her until she can't cum anymore...

Sorry it it was vanilla, but just thought that I'd share...
I sucked my own cock with my ex wife help. I still was hard getting the head in my mouth but when I was in position she would lick my balls and asshole as she pushed my cock closer.