Your Hottest Masturbation Experiences

Hot about a thread of our hottest masturbation experiences? I think it would be a real turn on and give each other ideas for some hot techniques to try

Please feel free to share and comment. Everyone welcome to share. Men, Women, Trans

Here is one of mine. This happened 12 or so years ago but I remember it like it was last night.

My wife was out of town so I decided to have some fun. We have a number of toys. Vibrators, dildos, butt plugs, realistic strap on. My wife's vibrator gets the most usage and the strapon is the forgotten toy sadly getting no love. My original plan was to get out a vibrating dildo and have some fun with it. As I went into our toybox I saw the strapon lying at the bottom. I picked it up to have a look. I've always been turned on by it. It's a realistic doc johnson 8 inch strapon. Looks amazing and I've always been turned on by the smell as well. I think because it reminds me of the strapon and of being naughty and dirty As I was holding it I thought what the hell let me bring this to bed as well. I had my favorite vibrating dildo and my 8 inch strapon and headed off to bed for some fun. I didn't have a plan for the strapon just thought I'd bring it to bed and see what I came up with.

I got cozy in bed. Had my laptop out and had Literotica loaded up. I started out by reading a few stories and getting myself hard and excited. Once I was good and ready I lubed up the dildo and lubed up my ass and slid it in. It felt amazing as always. It had been a while since I'd had my ass played with and I was loving it. Felt so good. At this point the strapon was just lying next to me. Still no plans for it.

I was edging myself along while reading stories on Lit. It felt so good. My plan was to have this gone on as long as possible. I started to get closer and closer to cumming. At this point I decided to turn the laptop off and focus 100% on what I was doing. I also didn't want to ruin the laptop with a big load all over it.

With the laptop off the room was pitch black. The dildo still in my ass. I decided to pick up the strapon. Just grabbing a hold of it turned me on. It felt so good. I brought it up to my face just to have a smell. I was really turned on and so horny. I was in one of those crazed horny moments where if someone walked in and asked me to do something there isn't a single thing I wouldn't have done.

Then I had an idea let me place the strapon at the tip of my cock and see if I could edge some cum on to the strapon then I'd lick it off. I always chickened out on tasting my cum after cumming so I thought maybe the combination of edging and the strapon would do the trick. As I place the strapon along my stomach and lined up perfectly with my cock I became turned on even more. I was close to cumming now. I thought let me just push a little further. So I moved the strapon so it was just touching the tip of my cock. The second it made contact I lost control and started cumming. My plan went out the door. This was no edge fest this was a full blown eruption. My cock was spasming and I felt 3 huge squirts land on my upper chest and stomach. Once I stopped cumming I was still horny. I still had the strapon lying along my stomach. I didn't know if any cum had landed on the strapon (it was pitch black). I knew I came a lot. I picked up the strapon and thought to myself should I do it? Should I lick it? So I brought the strapon up to my face and held it a few inches from my mouth and nose. The smell was different. I could smell my cum on the strapon. This really turned me on. I now knew there was some cum on it. I still didn't know how little or how much. I was really turned on but wasn't ready to lick it. I was chickening out again. I was holding the strapon directly above my mouth with the tip facing downwards just a few inches away but couldn't bring myself to do anything. Then it happened. A huge glob of thick creamy cum dripped off the strapon and landed on my lips and right into my mouth. It felt like a huge amount of cum. At that moment it was as if lightning struck. The shock and excitement that was sent through my body was like nothing I'd ever felt. I became so horny and crazy I opened my mouth and feasted on that strapon. I sucked every bit of cum off it. Licked it up and down and cleaned it. then scooped up all the cum off my chest onto the strapon and licked it clean again.

years ago, on an old account here , I had very random phone sex with a man. It was the most intense masturbation of my life. Soaked my bed from squirting repeatedly. Lost track of my orgasms.

There's been a few memorable ones....

Drinkmein said:

years ago, on an old account here , I had very random phone sex with a man. It was the most intense masturbation of my life. Soaked my bed from squirting repeatedly. Lost track of my orgasms.

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Very nice

newhere2learn said:

There's been a few memorable ones....

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Would love to hear one or more

Mr. Briggs said:

Would love to hear one or more

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In my wife's wedding knickers, ass fucking myself on camera for a chat friend.

Solo, naked, sissygasm.. repeatedly.

Stroking, sat 2" from a female fwb who was rubbing herself

newhere2learn said:

In my wife's wedding knickers, ass fucking myself on camera for a chat friend.

Solo, naked, sissygasm.. repeatedly.

Stroking, sat 2" from a female fwb who was rubbing herself

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Wow. NICE!

Masturbation to GF's Cheating Stories

When I was 20, I visited a GF who was in college, some way from the city where we grew up. She seemed quite pleased to see me, but very quickly confessed to me that she hadn't been entirely faithful to me during the time (six months) that we had been apart.

She was sophisticated enough to realize that the thought of her being a cheat was a turn on for me. And so she started to tell me about all the guys she had been with since we had last seen each other.

She didn't mind at all, when I took out my stiff cock and started to masturbate as she told me her stories. But she said I wasn't allowed to cum . . . so I didn't

My wife

All of my hottest masturbation sessions have involved my wife and sex with other men. Throughout our almost thirty year relationship my sexy wifey has cheated on me twice (that I know of. I suspect there was at least one more). The first time was many years ago. Mrs. Screwher started working in a coffee shop and Robert was a (married) regular there. Soon a sexual attraction developed between them. He ended up taking my wife to a hotel and he fucked her! At first I was livid! But soon after it was like a light switch flipped on. I started to become aroused by what she had done.

Then my wife and our daughter spend a weekend on an excursion with my wife's family. As I was masturbating visions of Robert fucking my wife in a hotel room came to mind. With those visions dancing around in my head I had my best jerkoff session ever! Then the whole rest if the time my family was away I basically masturbated. I had a collection of Penthouse Letters. I initially enjoyed that magazine for their girl on girl pics and stories. But this time around I gravitated to the sections that involved married women having sex with other men! The whole weekend all I did was stroke my hard cock reading these stories of slutty wives and thinking of other men screwing my wife.

I can’t narrow it down to one as I have too many, but I will say the CFNM situation I was in recently with two women from my hotel was pretty hot...

I have always liked to masturbate in front of someone who appreciates what I'm doing, and can share in the pleasure. Usually it's someone that I'm going to have sex with, or have had sex with, tho I have been known to masturbate in hotel windows, giving whoever may be in those nearby office buildings a little peek.

But I was working over my pussy a few years ago at home, when my cleaning lady arrived. I didn't hear her come in, till she came to the bedroom door. Then I heard her say, "Don't stop on my account. I can just work around you."

She's been cleaning for me for several years and we have had lots of conversations about pretty much everything. Nonetheless, I was shocked to see and hear her in my bedroom doorway! After a momentary pause, I laughed. "You caught me!" I said. "I really would like to continue if you don't mind."

She laughed and told me to carry on...that she thought it actually was hot, and if I didn't mind that she was there, then go right ahead. I was naked on the bed, with my vibrating jelly cock laying next to me, and my fingers on my pussy, so there was really no doubt what I was doing.

Well, that turned me on even more than I already was, to know that she was going to be there, able to see what I was doing, so I began to rub my wet pussy even more vigorously with one hand, caressing my breasts and pinching my nipples with the other. I felt like a slut on display and I loved it.

She began cleaning my bedroom, and stopped and watched as I plunged my purple vibrating jelly cock deep in to my wet, naked pussy, and began to fuck myself slowly, with my legs wide apart.

"My husband would love to fuck that," she whispered, as she watched and rubbed her own pussy thru her pants. I fucked myself hard and deep, increasing the tempo as she watched, turned on even more by her arousal, and I orgasmed loud and hard. She left the room, and finished the rest of the house, while I stayed in bed for some post orgasmic cool down play.

She wouldn't accept payment for her work that day, saying that "the show " was more than enough compensation

Many years ago I was living with this girl and the sex was pretty good. One weekend she came down with a miserable cold, you know the kind where you think you are going to die.

Needless to say I didn't get any loving Friday or Saturday and I was horny as hell. Sunday afternoon she's on the couch watching TV and still feeling like crap. I made her a cup of tea and sat with her.

I don't know where the idea come from, but all of a sudden I reached into my sweat pants and started feeling my cock. As it grew hard, I got bold and took them and my briefs off, so I am sitting bottomless next to her.

She said it looked so hot, but could not help me. I said no worry, I will handle this. I took my shirt off and kept it close to me for clean up purposes.

I edged myself for almost 40 minutes and she was watching closely the whole time.
Finally I brought myself to orgasm and shot a huge load all over my belly.

She said that was one of the hottest things she had ever seen, She had jerked me off plenty of times, and it was the first time I did it alone in front of her.

She promised to make it up to me when she felt better, and of course she did!

nassauguy_2001 said:

Many years ago I was living with this girl and the sex was pretty good. One weekend she came down with a miserable cold, you know the kind where you think you are going to die.

Needless to say I didn't get any loving Friday or Saturday and I was horny as hell. Sunday afternoon she's on the couch watching TV and still feeling like crap. I made her a cup of tea and sat with her.

I don't know where the idea come from, but all of a sudden I reached into my sweat pants and started feeling my cock. As it grew hard, I got bold and took them and my briefs off, so I am sitting bottomless next to her.

She said it looked so hot, but could not help me. I said no worry, I will handle this. I took my shirt off and kept it close to me for clean up purposes.

I edged myself for almost 40 minutes and she was watching closely the whole time.
Finally I brought myself to orgasm and shot a huge load all over my belly.

She said that was one of the hottest things she had ever seen, She had jerked me off plenty of times, and it was the first time I did it alone in front of her.

She promised to make it up to me when she felt better, and of course she did!

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Very sexy. Thanks for sharing.

My future wife and i had been dating several years before we went off to different colleges where she dated lots of different guys. Up till then, our dates would climax with me fingering her to orgasm while she rubbed my dick through my pants. One night at the drive-in, she unzipped my pants, took out my cock, and masturbated me until I shot all over the place. I knew she had learned the trick from other guys, but I didn't care. It was so hot to have her do it. I was better prepared next time.

I think I mentioned this in another thread. We had recently moved to Cape Cod. My then husband was out to sea, I didn't know anyone there and I was snowed in. I also had no computer or Internet. Only cable TV with a choice of very few channels and none appealed.

I wound up spending the better part of three days and nights doing nothing but masturbating. It was as though the more orgasms I had, the more I wanted! I did have a few sex toys and vibrators. I used those. I used my hands, the arm of the couch, anything I could think of.

My day three I was pretty exhausted and ready to sleep. I was also afraid I might have done some damage to myself from overuse. But... I'm still here.

Tnt69 said:

I have always liked to masturbate in front of someone who appreciates what I'm doing, and can share in the pleasure. Usually it's someone that I'm going to have sex with, or have had sex with, tho I have been known to masturbate in hotel windows, giving whoever may be in those nearby office buildings a little peek.

But I was working over my pussy a few years ago at home, when my cleaning lady arrived. I didn't hear her come in, till she came to the bedroom door. Then I heard her say, "Don't stop on my account. I can just work around you."

...

I fucked myself hard and deep, increasing the tempo as she watched, turned on even more by her arousal, and I orgasmed loud and hard. She left the room, and finished the rest of the house, while I stayed in bed for some post orgasmic cool down play.

She wouldn't accept payment for her work that day, saying that "the show " was more than enough compensation

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That's a great story, TNT. Loved it. My hottest masturbation experience was also in front of an audience, but in my case it was very much intentional.

After I left the sexual explorations of puberty behind, any masturbation that I did was on the sly. It seemed like a personal failing, not that that feeling slowed me down too much. That is until I had a girlfriend who told me she wanted to watch me. OMG! I never worked so hard to avoid anything in my life! For weeks, every time we went to bed she asked me to cum on her and multiple times a week, one way or another, I'd weasel out of it. I really didn't even want to admit that I knew how to masturbate, but finally I agreed to it.

As you all know, its no big deal and in fact way better than masturbating all alone. It took a few strokes to get comfortable in front of her. She let me know just how much she liked watching I just relaxed and went for it. It was pretty cool, BUT when I got to the point where I thought I should be feeling like I was about to cum I wasn't even close. I kept at it and used every trick I knew to make myself cum. Nothing. I kept stroking and at one point seriously thought about giving up, but I couldn't do that either. Still, nothing. I was jacking off like crazy, drenched with sweat, breathing hard and heavy -- still not even close -- until my gf took pity on me and gave my balls the lightest squeeze.

I came all over her tits, neck, tummy, pussy. I don't think I ever came so hard or so much in my life. My gf was plastered with cum. I was exhausted... and as I made to get off and lay beside her she stopped me with two words, "lick it."

There was no fight left in me. I did as she said. It was a lot.

Although she's long gone that afternoon is as present in my mind as if it just happened. Thanks for the reminder.

General

I was watching Taboo2. 18 m. Thought I was home alone! I heard guttural moans close by. My mother was spying me. I gave her quite a show

tmmmbrrr said:

That's a great story, TNT. Loved it. My hottest masturbation experience was also in front of an audience, but in my case it was very much intentional.

After I left the sexual explorations of puberty behind, any masturbation that I did was on the sly. It seemed like a personal failing, not that that feeling slowed me down too much. That is until I had a girlfriend who told me she wanted to watch me. OMG! I never worked so hard to avoid anything in my life! For weeks, every time we went to bed she asked me to cum on her and multiple times a week, one way or another, I'd weasel out of it. I really didn't even want to admit that I knew how to masturbate, but finally I agreed to it.

As you all know, its no big deal and in fact way better than masturbating all alone. It took a few strokes to get comfortable in front of her. She let me know just how much she liked watching I just relaxed and went for it. It was pretty cool, BUT when I got to the point where I thought I should be feeling like I was about to cum I wasn't even close. I kept at it and used every trick I knew to make myself cum. Nothing. I kept stroking and at one point seriously thought about giving up, but I couldn't do that either. Still, nothing. I was jacking off like crazy, drenched with sweat, breathing hard and heavy -- still not even close -- until my gf took pity on me and gave my balls the lightest squeeze.

I came all over her tits, neck, tummy, pussy. I don't think I ever came so hard or so much in my life. My gf was plastered with cum. I was exhausted... and as I made to get off and lay beside her she stopped me with two words, "lick it."

There was no fight left in me. I did as she said. It was a lot.

Although she's long gone that afternoon is as present in my mind as if it just happened. Thanks for the reminder.

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AHHH YES!!! This is perfect! LICK IT

Tnt69 said:

I have always liked to masturbate in front of someone who appreciates what I'm doing, and can share in the pleasure. Usually it's someone that I'm going to have sex with, or have had sex with, tho I have been known to masturbate in hotel windows, giving whoever may be in those nearby office buildings a little peek.

But I was working over my pussy a few years ago at home, when my cleaning lady arrived. I didn't hear her come in, till she came to the bedroom door. Then I heard her say, "Don't stop on my account. I can just work around you."

She's been cleaning for me for several years and we have had lots of conversations about pretty much everything. Nonetheless, I was shocked to see and hear her in my bedroom doorway! After a momentary pause, I laughed. "You caught me!" I said. "I really would like to continue if you don't mind."

She laughed and told me to carry on...that she thought it actually was hot, and if I didn't mind that she was there, then go right ahead. I was naked on the bed, with my vibrating jelly cock laying next to me, and my fingers on my pussy, so there was really no doubt what I was doing.

Well, that turned me on even more than I already was, to know that she was going to be there, able to see what I was doing, so I began to rub my wet pussy even more vigorously with one hand, caressing my breasts and pinching my nipples with the other. I felt like a slut on display and I loved it.

She began cleaning my bedroom, and stopped and watched as I plunged my purple vibrating jelly cock deep in to my wet, naked pussy, and began to fuck myself slowly, with my legs wide apart.

"My husband would love to fuck that," she whispered, as she watched and rubbed her own pussy thru her pants. I fucked myself hard and deep, increasing the tempo as she watched, turned on even more by her arousal, and I orgasmed loud and hard. She left the room, and finished the rest of the house, while I stayed in bed for some post orgasmic cool down play.

She wouldn't accept payment for her work that day, saying that "the show " was more than enough compensation

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OMG This is so sexy. Thanks for sharing.

Undoubtedly

with my filthy Skype friend. Seeing and hearing her cum three or four times as I edge, then getting there as she watches intently... Yes, pretty memorable.

A few too many to list. One that sticks out was a friend and I fooling around a few years ago. We were drunk and next thing I know she had two fingers in my pussy. She made me cum over and over and over. Makes me wet just thinking about her little tits jiggling as she finger fucked me.

jazintime said:

Crazy...was watched for the first time....I was getting my hair cut by my hair stylist at her house. Our conversation changed to how much she enjoyed sex with her ex and she went into graphic detail....I couldn't believe how hard I got. She couldn't help but notice my cock straining at the button fly of my jeans.
She said it must be a little tight in there huh....why don't you let it out for some air.
I don't know what came over me but my fingers slowly started to unbutton my jeans...my cock popped out at full mast....she simply said "gorgeous...now stroke it for me please"...the precum was dripping down the swollen head of my cock. I collected my precum in my fingers and wrapped my hand around the shaft of my cock. My hand was gliding up and down my cock, she came and knelt in front of me and watched...I couldn't help but moan with the pleasure, the erotic atmosphere and her being inches away with her eyes glued to my cock and the movement of my hand. My hips started bucking, my cock swollen and throbbing... I started shooting hot rope like streams of cum all over her and she just kept saying more....it was the most erotic experience I have had...crazy, we never touched each other we both just enjoyed the intensity of the moment....perhaps I have a new pleasure...selfish exhibitionist......

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nice.

one that often springs to mind,when i,m asked this question,was some years ago now. i was talking to a woman friend online. she was on cam and giving me instruction.i was not on cam,and so she was fully dressed.by the time,she had made me cum,she was naked and playing along too..

red_don said:

one that often springs to mind,when i,m asked this question,was some years ago now. i was talking to a woman friend online. she was on cam and giving me instruction.i was not on cam,and so she was fully dressed.by the time,she had made me cum,she was naked and playing along too..

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Lol! You get asked this often?

LOL fun enough no not really... but i did enjoy it