Best Masturbation Session Memory

Do you remember the best time you ever had while masturbating? Alone or with others?
I remember doing it in a nature preserve near my dorm. I rode my bike out there wearing just overalls. I laid down in the grass face down, and humped the ground until I came.

 

Well where to begin! Every wank is unique. I guess some stand out. I like the ones where I wank in front of my wife and cum on her tits the most.

 

my first was great. after that, they've all been pretty much the same.

 

Had two orgasms one time. I was edging and stopped to late but still early enough to start up again a couple seconds later.
Tried a few times but could never do it again

 

When I was a senior in High school and after my dad left my step mother I continued to live with her. One day I came home from school early and heard moaning at the end of the hall. It was my step mother masturbating. I couldn't take my eyes off of her. Watching that dido going in and out of her pussy was incredible. When she saw me she started screaming get out. I went straight to the bathroom because my penis was troubling after that. It didn't take long and right when I started my orgasm my step mom opened the door and watched me. I tried to hold but no way. I came hare than I ever have and actually hit her with about 3 swirts. She said now we're even. To this day that's the most intense orgasm ever. We actually started masturbating together for a while. Loved it. She had one of the most beautiful pussy's I've ever seen.

 

This is the one that I will never forget. One time while I was in the military, I was working a late night shift with a female co-worker. She and I were friendly, but never had any physical contact with each other, outside of a pat on the back or a light punch in the shoulder. On this particular night, she told me that she was hot and horny, because her husband was on a military deployment and she hadn't had sex in quite a while. I just didn't know how to respond. She said that she wanted some sexual release, but wouldn't cheat on her husband. I was also married, and I told her that I didn't want to jeopardize that by getting into a physical relationship with anyone. She replied she was getting tired of using a vibrator at home alone, and wanted a little more sexual excitement. That started making me get a hard on, but I still didn't know what to say, other than I understood her situation. Well, we were the only two at in the building that night, and we got into some more sex talking between us, and then she surprised me by suggesting that we masturbate together while watching each other, but staying apart. By then I was getting pretty horny, and agreed with her suggestion. We went into an office, and we both sat down in those standard swivel office chairs.. We stayed mostly clothed, but she lowered her pants and panties down to her ankles so that she could spread her knees and open up her pussy. She then unbuttoned her shirt and pulled her bra up to expose her breasts and began to rub her tits with one hand while she was fingering herself with the other. I unzipped my fatigue pants and dropped them down to my ankles and pulled the front of my underwear down under my balls, started jacking off while watching her. We were fairly close to each other, but not touching. I had to pace myself, and keep edging to prevent cumming too soon. She licked the fingers of both hands so she could get her nipples wet. She kept talking out loud about what she was doing to herself - "I'm slamming my fingers into my pussy." "I'm pinching my nipples." "My **** is getting so wet." "I'm fingering my clit, and it's gonna make me cum so hard." "It's making me horny watching you jack off." "Cum for me. Shoot a big load." Things like that. After several minutes of this, she had a strong orgasm, and pushed her fingers hard into her pussy, pulling upward and clamping her legs hard around her hand, moaning and telling me that she was cumming so hard. Well, I couldn't hold myself back any more, and I stood up so I wouldn't shoot my cum onto my pants, and ejaculated my load onto the floor in front of her. Which I then had to clean up, after almost passing out from my ejaculation while standing.

That was a hot session, but the same circumstances never arose again, so we never had the chance to repeat it. After about a month, her husband came back from his deployment, and she seemed to be more relaxed, so I guess she was getting what she needed at home. She and I worked together for a while longer, and would share a quick wink every now and then, both of us remembering that night.

 

When I was in my teens we went on vacation with my friend's family. I had a major crush on his mom. Beautiful hourglass figure. First day she comes down to the pool in this one piece bathing suit and her 36D boobs are just falling out. That night everyone else went out to eat but I said I wasn't feelling well. Knelt on the bed imagining she was underneath me. Edged a few times and then I just exploded imagining cumming all over her chest.

 

In my early teens, we had a masturbation club in the neighborhood. It consisted of five guys and four girls from the neighborhood. It was pretty common back then for us to sleep outside under the stars on the weekends and not sleep but talk about crazy things and harmlessly walk the neighborhood. We guys happened to one night come across the girls doing the same thing. Said they were sleeping in a tent in ones backyard. We visited and talked. As summer went on talks became more interesting. Sex was discussed but not an option but we did enjoy the old strip poker game. Once that was getting old we decided on the losing hand had to show how they masturbated. It eventually became fun just to watch each other just do it and occasionally lend a helping hand. Strict rule was nothing more than hand work. Oddly.... We had one male that was great friends of us all but very modest. He never stripped past his shirt and sox in the card game. And never masturbated with us. But being a friend of us all and understanding of him, we allowed him to be with us just the same. This was only one summer i recall that this went on and we had an occasional new visitor here and there of friends we knew from school or adjacent neighborhoods. We did at times come across each each other of course and maybe have a smaller session with each other. Eventually we all started dating and things became a more norm in our lives sexually.

 

Well, not so much a memory(perhaps at some point though!), but the session I just had produced one of the most powerful orgasms I've ever had.
Two hour session started when I got an urge and was really hard. So I stripped naked. I slowly started rubbing my hands around my hard dick upper legs and ass. Did this until I started oozing pre cum. Then I started stroking and felt my scrotum which was tight and hard. Then after this I turned to porn. I'm a major ass lover, so found my favourite woman's ass site which really got the imagination going. My dick started throbbing as a stream of pre cum stretched from my tip to the floor.

I started edging myself after this. I broke up the edging sessions in between by watching random YouTube videos to prevent myself from going too far. When I was ready again, I turned back to ass pictures and went at it again. Did this for an hour and edged myself about five times. Finally when I couldn't take it anymore, I went for it. Didn't look at porn, but since I have a female friend that is quite frankly the most sexiest woman I've ever seen, and I've seen down the back of her pants and her gorgeous bare ass, I thought of her. I shot my load in 30 seconds once I started thinking of my friend. Intense orgasm.

Posting this has made me horny again. May have to go for another round.......

 

I love getting into the laundry basket and find soiled panties. This has been my fetish all my life. I am 55 now. Last year my pastor ask me to see if I could repair his washing machine. It was in the basement. Dirty laundry was everywhere. His wife. the preachers wife was pretty nice looking. Big but and big boobs. Her large bras and panties were in the basket beside the washer. I could hear her walking around upstairs. I got a pair of her panties and started smelling the crotch. They smelled so nice. I took out my cock and started wanking. I smashed her panties against my nose and took deep breaths while I masterbated. I shot a load across the washing machine. It was so good it hurt. i have never cum so hard in my life.

 

On a rooftop of a high rise with my telescope watching two women in two different apartments masturbating at the same time.

 

The best masturbation days of mine are in my twenties. I will never forget my neighbor who took her bath naked in the open. I jerked my penis till i EJACULATED. I used to sleep naked on bed and masturbated reading porn books and imagine fucking the neighbor naked lady. I will never forget this.

 

Be awful hard to say...over the past 35 years, like any guy in that many years it would be a couple thousand times by now.
I do remember one time I was probably 17-18 years old, I was super turned on after a date with a girl and went back home and went at it...it was so intense that the ejaculate splayed on the wall behind my head.
Doubt I could do that now!

 

Come on dudes, even your worst fuck is better than your best masturbate lol. Who remembers that shit anyway.

 

“Don't knock masturbation. It's sex with someone you love.”

 

People remember and reminisce about this?

 

I have had many memorable sessions. That was the intent of them as my husband filmed me in some rather lengthy sessions so that he/we could watch them later.

 

Please don't judge, but when I was young and because my sister is 9 years older then me, I used to spy on her in her room changing and walking around her room naked. Then After she would leave the house I would go in to her room and look for her hamper for her panties and bras then I would take off my cloth, lay on her bed and sniff and lick her panties and bras while jerking off. But the most intense time is when I put on her silky nighty and used panties while I sniffed her bra.

 

I know that all sounds gross but I was young and really awkward with girls.

 

LMFAO!!!

 

My girlfriend came to my dorm room one evening and we were both naked just doing stuff to each other that we enjoy, she sucked me off, i ate her out for a bit, we kissed, yada yada, anyway I'm rock hard and am kind of desperate for her to finish me off when she looks at the time and says she has to go get some sleep before her lecture in the morning. I was like, what?! I ask her to finish me off and she says save it for tomorrow and I'll reward you. So she left but my erection remained, I was so hard it was unreal and I couldn't just leave it, so I grabbed and jerked off. I shot across the room and moaned as loud as I ever have, my knees shook and I just fell onto the bed, it was absolutely mind blowing.