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Memorable Masturbation moments....

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Started by #289712 [Ignore] 01,Jan,16 05:21
All of us have masturbated an endless number of times, had countless orgasms, a multitude of ways, and an encyclopedic catalog of varied situations. Yet there is always a few times that stand out, for one reason or another. I've got a few. Good,bad, funny, awkward, amazing, whatever! Cast your minds back, and please share with us all one or more of the times you were pants off, rubbing one out, that have stuck in your head ever since!! Can't wait!

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By 1975monte [Ignore] 29,Jan,23 11:15 other posts 
Most memorable time was using my first prostate vibrator. That is pure heaven. I lubed it up and slid it in slowly. Once I had it all the way in I set the vibration and pop precum instantly started oozing out. Of course I licked my fingers off. I stroked it very slowly with coconut oil and held back as long as I could until I just couldn't take it no more. When I felt my cum I squeezed my balls so hard and let the vibrator do the rest. I was a cummy mess and it was so hot. It's always my favorite way to masturbate.

By XJacker [Ignore] 27,Jan,23 11:03 other posts 
Though I was getting regular sex with my wife I still needed to masturbate. Sometimes in bed with her if we hadnít had sex I found I could gently stroke off my hard up penis with just my thumb and forefinger across the base ridge of my cock head and manage to stifle my orgasm grunt and the involuntary thrusting of my hips when I shot my load without her realising I was wanking. I went on like that for a while.

Then one night I was in bed with her and my erect cock felt stiff enough to snap. I was desperate to jerk one off. She was awake but she wasnít in the mood for sex.

I plucked up my courage, told her I had an erection which just wouldnít go down and would she mind if I brought myself on. She said she didnít mind at all. She masturbates herself and she knew all about male masturbation.

As I wrapped my fist round my cock to wak she snuggled close to me. She squeezed her breasts against my arm and folded her bare leg over mine so my spare hand could stroke her naked thigh right up to her bottom and reach down to her cunt. She slid her hand across my thigh and down between my legs to lightly caress my inner thigh tops, my groins, my balls and my arse. She knew from fdoreplay that got my erect cock as hard as a steel bar.

Freed from any inhibitions I tugged and stroked my cock for all I was worth, like I did when I was single. But instead of solo wanking I was playing with her naked body too with my spare hand. She was still caressing me between my legs when I came and I shot my load right up my belly. She even handed me a tissue to clean up!

Since then sheís helped me to masturbate like that lots of times, but that first ever time was certainly a ďmemorable moment.Ē

By All469ernow [Ignore] 26,Jan,23 22:44 other posts 
Couldnít control the explosion moaning on this one

By 4438cr [Ignore] 25,Jan,23 04:59 other posts 
Several years ago I had a gf in addition to wife. The gf had a great sex drive and never said no! One afternoon we got together but she was on her period so she sucked me for a while but I didn't cum. She had me sit on her face while she rimmed me. I started stroking my cock and when I was about to cum she stuck her finger up my ass and rubbed my prostate gland! I shot cum all over her tits and belly!!!! About an hour later we repeated the this!!!

By lawrenceo [Ignore] 25,Jan,23 04:31 other posts 
I was camping with another boy who I knew from scouts. He was cut and he wanted to see my uncut dick. As soon as he saw it he wanted to wank it as he hadn't done it with an uncut dick before. It didn't take long before he brought up my spunk. He then lay on his bedding with his hard dick upright. I took the opportunity of returning the favour. His dick was smaller than mine but he was happy with the way I rubbed it (I had only wanked one cut dick before and it was too sensitive to do it for long.) He quietly enjoyed what I was doing and my hand was soon covered with his spunk.

By routemaster [Ignore] 24,Jan,23 02:34 other posts 
Wanking and cumming with other guys at gay orgies

By tixHH [Ignore] 24,Jan,23 00:40 other posts 
First time in a peepshow booth. Watchinng the nude girl made me cum in seconds with shivering legs.

By Moby61 [Ignore] 23,Jan,23 07:06 other posts 
Me and my wife were on a trip in a minivan going over the salt flats in Bolivia and everyone was asleep in the van, luckily we were at the back so I thought why not so just gently messaged my dome till I spurted over myself, the Mrs still doesn't know but very enjoyable.

By Robben [Ignore] 23,Jan,23 03:39 other posts 
When I was a teenager I masturbated several times every day. The pressure and amount of cum was high and it seemed I could cum and cum after another. Well, I remember a special occassion when I sat on toilet and masturbated and the cum flied up to the ceiling and the wall by the pressure from inside. It was a good lesson how to NOT do it because its a mess and time consuming to clean up. After that time I was more careful how I let it cum.

By Mynakedcock [Ignore] 19,Jan,23 19:28 other posts 
One year when I was in my teens I was on a big family camping holiday with my parents, sister uncle and aunt and my two cousins, and all us kids slept in one tent boys and girls together. It was a hot summer so I slept naked and with my sleeping bag unzipped, I was feeling very horny as I had got a glimpse of my cousins pussy when her nightdress lifted when she was getting into her sleeping bag, and my cock grew very hard so I started rubbing it thinking as it was dark no one would notice I wanked off enjoying slowly rubbing my cock and the thought of being caught made the enjoyment even better I eventually cum shooting my load over my chest and belly.
By XJacker [Ignore] 20,Jan,23 16:48 other posts 
A delicious memory! Did your cousin see your hard up cock and see you wanking it!
By Mynakedcock [Ignore] 22,Jan,23 13:51 other posts 
She didnít say she did but Iím sure she knew what I was doing.
By XJacker [Ignore] 22,Jan,23 16:34 other posts 
Most girls know what boys get up to!

By #552884 21,Jan,23 16:38
Mine was this one my very first video I uploaded online jacking off with cumshot, Remember the day well had a free house was feeling pretty horny so ended up stripping off and spending time messing about with my dick resulting in this video
[deleted image]

By leopoldij [Ignore] 18,Nov,18 21:06 other posts 
I was challenged by a female colleague to masturbate in front of her when we were alone in the office. I did. No Sex involved. She just wanted to watch and I showed her. Of course, the idea of exposing myself and masturbating for a girl who'd never seen my cock before made me so horny that I shot a really huge cumload. When I finished she was saying wow, can't believe it. That was the most memorable masturbation session relatively recently. I've had many in the past though.
By Lvphose [Ignore] 19,Jan,23 03:16 other posts 
Great story wish I had a similar experience!
By leopoldij [Ignore] 19,Jan,23 05:58 other posts 
Let us know
By Lvphose [Ignore] 19,Jan,23 20:25 other posts 
Iím game when ever!
By XJacker [Ignore] 19,Jan,23 03:19 other posts 
Wanking with an audience is always much more fulfilling than a solo Jack off. Even better with audience participation!
By leopoldij [Ignore] 19,Jan,23 05:59 other posts 
Fully agree

By Lvphose [Ignore] 19,Jan,23 03:22 other posts 

Hereís a very memorable masturbation. I have a huge pantyhose/nylon fetish love women in them and love wearing my self! Hadnít gotten the nerve to share with my Girlfriend Iíd call a sex line and beat off what the chick was talking about wearing pantyhose-getting fucked in pantyhose etc! I was so into it I didnít realize my gf came home and walked into the bedroom and caught me! Ruined the session but it was like being edged and shot a big load later that night alone! But it did force opening up about my sexuality!

By Thicky [Ignore] 01,Jan,23 10:36 other posts 
I have one memory. Kind of funny and certainly memorable.
Being on a visit to friends and spending the night with them made me feel good. Somehow I hadn't noticed before that the blinds were not drawn on the windows. It was only when I shot my cum that I noticed that I could be seen a little...
To this day I do not know who saw me, No one commented, so I guess they liked the show

By LGA6969 [Ignore] 18,Dec,22 17:34 other posts 
When I was about 15 or so I was in my bedroom and decided to jerk off. I got all naked laid on my bed and started jerking off I decided to throw my legs back over my head so that when I came I would come into my mouthAs I was coming into my mouth my dad happen to come into my bedroom I forgot to lock the door. So needless to say I was so embarrassed and all my dad did was laugh and left and shut the door. Later on he was laughing and he said that that was a nice shot. Lol

By #620582 06,Jul,20 12:28
I was 19-20 when I read that there are boys who can suck their own dicks. I decided to give it a try. I was still a thin athletic guy at the time, but my dick is quite small, about 13 cm. I had to try for 2-3 weeks, but once I touched the tip of my cockhead with my tongue. It was a wonderful feeling and I was so excited that I cummed very quickly. Later, I could reach the cochead with my lips as well, but unfortunately I couldnít get any further, even though I wanted so much that my neck or back also hurt.
I was sometimes successful until I was 50, but by then I had to warm up and exercise properly before. But the first time was so good that I still have an erection if I remember.
By doedeldi [Ignore] 18,Dec,22 07:29 other posts 
Habe es leider nie geschafft.

By corby [Ignore] 13,Dec,22 17:46 other posts 
My wife and I were on a Mediterranean cruise.. The ship had separate male and female spas. I used the steam room for a few days and it became clear that it was frequented by Bi guys looking for some fun.. My first experience of the scene. I ended up having two guys playing with my cock, whilst 5 others watched.. I was so hard and exploded, what seemed like a huge stream of cum sprayed across the floor.. It was such a hot, and literally steamy experience, I've been hooked ever since.

By Hrnyboy90 [Ignore] 13,Dec,22 14:52 other posts 
One of my best ones took place a few years back when I was on a vacation with an old girlfriend. We had a cabin that was in a quiet secluded area with a private deck around back and a hot tub. The first night we were out sitting in the hot tub together and making out. I wanted to go farther but she wasn't feeling that adventurous. She went inside to take a shower and I was out by myself. I was already really horny and playing outdoors is one of my favorite things. I decided not to pass on the opportunity and it was play time for me. The first thing I did was slide off my swim trunks. Then I stood up and walked out on to the deck. The feeling of the cool air on my naked wet body was breathtaking. My dick was rock hard again and needed to cum. I decided to sit naked on the balcony and masturbate over the trees below. It didn't take long to give myself a super intense orgasm. Masturbating naked outside is an experience like nothing else.. And hearing your cum fall onto the trees and grass just puts it more over the top

By XJacker [Ignore] 13,Nov,22 16:43 other posts 
I was in bed one morning naked with a girl after sex the night before. My cock was hard up erect. She asked me to show her how a man ďdid itĒ with his hand. I was happy to oblige! Laying back in bed I put on a good meaty show for her with my fist round my shaft, grunting, thrusting, stroking full length and edging. I shot a big load up my chest. I think I impressed her!

By #622870 02,Aug,20 05:58
I will never forget when I blew my first own load in my mouth.Or when I borrowed brothers wife's panties with dildo and rode it while wearing her panties.

By #535695 05,Feb,19 12:36
Just last night I jacked off, setting on a guy while he fucked me with his cock up my ass, Gawd I came so hard and my load was huge.
By #607259 17,Jul,20 18:56
Oh man! Thatís my favorite guy sitting on my cock jacking then shoot on my chest!

By liketoedge [Ignore] 05,Feb,19 11:49 other posts 
I will never forget that very first time. A nieghbor boy stoked me to my first dry orgasm and I've been hooked ever since. About 5 year later I will always remember to first time I was able to ejaculate...that was a proud day. I also will remember the times i did it with other friends growing up. We were always secretive about it but i will never forget those times
By spermkiss [Ignore] 05,Feb,19 12:19 other posts 
Such lovely childhood memories. Fooling around with other boys is so normal and is part of growing up.
By #607259 17,Jul,20 18:55
Lots of great orgasms as an adult. However there is just something about them boy orgasms with other boys. Oh to go back to boyhood for just a bit.

By #546418 11,Feb,19 08:43
Very recently. I'm trans and when I started hormones I basically had almost no cum for a month. And if you look at my page, my ability to gush cum is something I'm proud of. At any rate about a week ago my ability to shoot impressive amounts of cum came back! Best wank ever, covered myself with cum, and it hasn't gone away since. The cum is a different consistency though but whatever there's lots of it again. I also have a considerably shorter refractory period, sometimes it's non existent.
By #607259 17,Jul,20 18:46
Congratulations on making the transition to who you really feel you are!

By galaxy123 [Ignore] 06,Jul,20 05:35 other posts 
my family were naturists when I was growing up. Sometimes as a teen, when naked on the beach I would get hard and a little embarrassed. A friend of my parents suggested having a wank before going to the beach or go for a quick wank in the dunes near the back of the beach. So I would go to a quiet part of the beach and masturbate as ejaculating would get rid of the erections for a while. Sometimes I was aware of people watching which I did not mind too much.
By #607259 17,Jul,20 18:41
Bet there were lots of dirty old men watching you wank!

By #621517 11,Jul,20 17:09
I was in bed naked with a naked woman one morning after sex the night before. She asked me to show her how a guy masturbates. I got into my favourite wanking position, kneeling wide legged with my hard cock sticking straight out. I stroked, tugged and edged and made lots of noise grunting. I also fondled her naked body with my spare hand. I made sure I put on a good show for her and Iím glad I spurted a big load.

By #603370 06,Jul,20 23:49
One time after gf had a procedure done, we had to wait some period of time before intercourse. One afternoon we both needed to cum, and we just took down our pants and started manipulating each other. No shit, it only took about ten seconds and we were both cumming, she was crying out and convulsing; I came so hard but managed to catch it in my hand instead of soiling the carpet.

By overeight [Ignore] 04,Jul,20 12:04 other posts 
Well ill say the most memorable time was once this woman and I lived together and I was very attracted to her but she really liked me but not really sexually attracted. So the house we were in had only one central heater and where the house was in central Florida it rarely got cold enough to use it. However it was a very cold winter that year so we had the heater on. Well our doors to our bedrooms were open to let the heat circulate in the house. Well I was super horny that night and after going to bed I just could not sleep and had to get off. So I slept nude so I pulled the covers down and just started stroking it out. Well apparently I wasn't quiet enough for her not to hear. I was super hard at the point of to far to just stop. I saw her feet just outside my door after I heard a noise just outside my room. Well seeing her feet hot me more excited and I kicked the covers completely off me spread my legs open and stroked a little faster. Shortly shot a very intense load and was so reved up I let out a big aaaaahhhhhh ooohhh aaahh mmmmmm when I shot. I laid there just a probably full minute and slowly still stroked it still rock hard. Well then I jumped up quickly to dart to the bathroom to clean up. As soon as I made it to the door there she was her shirt pulled up above her breast her hand in her panties all wet her eyes closed her body convulsing. Once I stepped out in front of her standing there playing with herself. I kissed her on the cheek and she opened her eyes surprised that I was standing there naked watching her get off by watching me. She was stunned and embarrassed. I told her its ok we all have needs hun. You might not want sex with me but its ok that you enjoyed watching and got excited. She kissed me back on the cheek and said thank you thats sweet. She looked at me up and down and said your a fairly big guy there and I just honestly wanted to see it and how big it was I heard you but couldn't help myself and got well I lost myself. I said its fine I'm going to clean up but when I come back you can be in whatever bed you want mine if you want what you see yours if you dont or aren't sure. I went and wiped myself clean. When I came back she was at her bedroom door and said I dont want to make such a decision being so charged up right now but I will decided and if I want to go there ill let you know. So I went back to bed. The next morning she told me during breakfast I hope we can keep this just between us. I told her well its nobody else business. She said good I dont need the embarrassment. I said well I was the one who got caught you just got caught up. She laughed and said well I did kina enjoy it too. So we never talked about it again.

By #616943 09,May,20 10:34
I have a jack off buddy who is hit and miss. I had the house to myself, and it was like 8pm. I thought I would try my luck , and gave him a call. I asked if he wanted to come over to watch porn, and Jack off. He surprisingly , he was on his way. The Lure of the big screen, and home alone must have sounded good.. I waited for him in my boxers. Once he showed up, I locked the door, and stripped naked. I really enjoyed being naked in front of him. I set up the vcr and TV all in the nude. I made sure to lay out in the middle of the floor, so he couldn't not see me. I took a slow and steady pace to prolong the pleasure. The first few hours edging had me releasing precum only. But the next few hours, pressing the edge had me releasing cum just not to orgasm. My buddy could see me all glistening, and kept asking if I had came. He usually paid me no mind. I promised to let him know when I was going to cum, so he could watch me. About 7hrs later I couldn't hold it back any longer. I began to moan and squirt leading to the actual orgasm. I grunted with every huge spurt. My buddy stared for every last drop. I stood up next to the TV for the next couple hours to work the vcr. MY huge orgasm dripping down my thighs and stomach. Goodtiimes!

By #603065 28,Oct,19 23:15
I will never forget my first time masturbating and trying to blow my load in my mouth.I missed and came on my face, chin and neck. Another time which i wont forgot is when I masturbated with a banana inside my asshole.I put condom on a banana and jerked off.Felt great when I came.

By #516354 21,Sep,19 03:45
My most memorable masturbation moment was my very first one;
I was 14 and used to do a paper round.One day my next door neighbour asked if she could come with me(she was also 14).On the round there was a playground with a big play house,she asked if I fancied a cigarette so we went into the play house and started smoking.As we sat there and smoked I kept glancing over at her and could see her panties, which were on view, and started to get a hard on.I had had them before but was not sure what to do.She noticed my hard on and asked if she could see 'it' so embarrassingly I stood up an pulled my jeans and pants down.She took hold of cock and started to rub it up and down,she did this for a few minuets and it felt really good.Then told me to do it myself and as I was masturbating she lifted up her skirt and took off panties and started to play with herself.I soon had my first orgasm, shooting my cum all over the floor and stood there red faced and embarrassed not understanding what had happened.She giggled and said it was ok and that she had spied on her older stepbrother a few times and was supposed to happen.We repeated this on several occasions and after a few months we even both got naked and she let me touch her small breasts and her pussy whilst masturbating.

By #519017 31,Aug,16 15:33
When I was sitting up in bed naked with my woman naked beside me. I had a massive hard on. She asked me how a guy masturbates. She'd never seen a guy jack off! So I lay back and as she watched I stroked and tugged a good one off, making lots of noise grunting and ramming my hips to put on a good show and fondling her boobs as she leaned over me watching. I made sure I took ages and splashed right up my chest. I think I impressed her!
By #595788 13,Sep,19 17:58
Sounds the same as my experience. I was sitting naked in bed with my woman in the morning after a night of sex. I was having a good rock hard boner. She asked me to show her how a man did it with his hand. I showed her, making sure I put on a good meaty show making lots of noise, and jerked a good load.

That and the first time I ever wanked of course. Oh yes and the first time I ever masturbated naked with another boy in a swimming baths changing cubicle.

By #574047 11,Feb,19 11:36
Some days passed one boy aged twenty five years hes masterbating my dick and sucked my dick. He agreed to take my dick at his ass hole. He played with my dick for a long time

By HardAtWork [Ignore] 08,Feb,19 20:08 other posts 
My most memorable one was when I knew this female family friend was going to be coming over. We had fooled around a little bit in the past...Touched and kissed her tits... She would just walk in the house when she came over so one day I decided to let her "catch" me masturbating...The wife wasn't home from work yet. So, she walked in and there I was, totally naked with my hard oiled up cock in my hand. She walked in and froze, looking at me, then turned her back so I could get covered up. After I put my clothes back on we sat down and were talking. She said, "I didn't what to do when I saw you there. Should I leave? Turn around to let you get dressed? Or should I help him finish? Of course I told that "help me finish" would have been the correct answer! I tried it again the next time she was going to be stopping over for a visit...

By MyArtwork [Ignore] 08,Feb,19 19:22 other posts 
These were fun lol

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By #423426 06,Feb,19 10:23
I was at a nude park last year and kept getting an unwanted boner, so I went into the bushes on the hillside overlooking the park to sort myself out. As it's quite secluded, it's also a gay cruising area. I found a quiet spot but after I'd started, I noticed a clearing nearby where two guys were sunning themselves so I walked over naked with a hard on and just wanked off in front of them as they both played with themselves while watching me. Not a word spoken.

By gingerhentai [Ignore] 05,Feb,19 19:58 other posts 
When i went to an adult bookstore to see what it was like. Porn was so so, but just being there made me spill on the floor

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