Most memorable masturbation moment

Has to be the time that my dad walked in on me as I was was lying nude and spread eagle on top of my bed (so there was not way to quickly cover up) and nearly at the end of an hour's worth of edging. Nearly ready to cum when he walked in on me, the excitement of seeing him standing there tossed me over the edge and I shot a huge load all over myself. It could have been a bad scene but he thought it was hysterical and laughed his way out of my room.

Second shot at this. Maybe more on theme. Gym in City used to be gay but not anymore. Was a member for several years, and on this occasion had my usual workout and wasn’t crowded so decided to take a sauna. Stripped down, grabbed a towel and headed in. Surprised the only guy in there and he quickly dropped his hand from his cock, looking at me sheepishly. So decided to see if he’d join me…Started stroking and he was on his cock like lightning. Kept an eye through the door window and kept on til we both blew our loads all over our junk and bellies. Then headed to the showers with a silly grin on our faces. That was some sauna…Guy was as hot as the sauna, too.

It was during a virtual medplay examination with a playdoc I just met online. I was completely naked with the cam staring to my privates. The doctor asked to stretch my flaccid penis as long as I could. Then retract the prepuce. She said it was tight and asked me to do some preputial gymnastics let it retracted and see if the glans remained uncovered. Seeing my genitals on the display from the cam and knowing everything was seen by her was extremely embarassing and exciting at the same time. I got an erection she said it was an healty reaction and to continue with the exam. Shortly after I ejaculated profusely. This was one of my best masturbation moments expecially for the mental involvement the play doc created with me.

Many wonderful moments as a young teen, sitting in front of my mirror, exploring myself and resulting in orgasms.

Would have loved to have been a fly on the wall for that @GraceT .

It would be between two. The first time I caught my sister masturbating and she showed me how to do it and that it was alright, nothing to be ashamed of.

Or the first time I had an orgasm while masturbating being filled and taking the full bag.

Every time I have a full bag in me and I’m striving for my happy ending is a memorable masturbation moment😍😈😁I feel self love and acceptance while waves of kinky pleasure wash over me😍 😍

My hottest masturbation experience was with a former girlfriend. We went to the cinema and watched an older soft porn film that was often shown late at the time. I couldn't help but caress her nipples through the shirt, which she really liked. Suddenly she pushed her hand into my boxer shorts and took care of my erect penis. She began to masturbate me slowly and invisibly to others. I then whispered in her ear to stop or it would happen. She whispered "so what?" back and continued until I cummed in several spurts in her hand and in my pants. I then quickly ducked into the toilet to clean up the mess. When I returned she was still licking her finger.

Another fond sauna memory...Also at a former gym I joined

They did away with hot tub and steam since women didn't have them. Something about equal access. But the sauna remained. Through a small window you could see if anyone was coming. So on more than one occasion a hot muscle defined guy comes in and we're alone. After a few minutes he hps down from the bench and backs up to me and spreads his cheeks. I usually wouldn't do anything but I gave in to lust and started to screw him. Kept on til I shot and pulled out dribbling on him and myself . Then separately we headed to the showers. It happened s couple more times, we never got caught.

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Early 2000s, a guy had this "Czech Up" picture as his profile:

https://en.zity.biz/gallery/image/200356

I literally cracked 4-5 wants in a row over it.

I suppose the one that stands out is when I was ordered to mastrubate for my Dom on a video call. I had my knee up as I I know he prefers the teasingly view. But at some point, he told me to put my knee down so he could see properly!!!

Those words did push me over the edge and it took a while to catch my breath after my orgasm.

This is such an interesting question and with a lifetime of masturbation, a very difficult one to answer. I guess that as I think back about it, the most memorable one would have to be the first time I masturbated to orgasm with an ejaculation rather than coming up dry. I still vividly recall finding my parents old school vintage massager with a cup style attachment on it that just looked liked would fit perfectly on the tip of my prepubescent penis. The anticipation of touching the head of my penis with that machine built as I stripped my clothes off, found a plug to power the device, and laying naked on the floor of my parents bedroom between their bed and the dresser where I found the massager. I was erect from the time I discovered the massager until I was on my back with my penis in the bell shaped cup of the massager. The massager was very loud as I recall. Then there was the unique feeling of what I was experiencing and that the pleasure kept building in a way I had never experienced before. The inside of the cup was getting slippery with my precum which was a first for me at that point in my life. My penis seemed to feel harder than ever before as this unique new tension built in my body. This new tension built in body from the very core of my being as I felt huge contractions in my penis as a creamy white fluid pumped out of me. I recall being amazed, scared, amused, euphoric, while at the same time a bit paranoid because I had a lot to do before to get cleaned up and squared away before my parents returned home. The first of a lifetime of the joys of self pleasure. I don't know what ever happened to that massager but it is no longer around. That is one of many things I kept a lookout for as they aged, downsized their home, and ultimately passed away.

For me it was as an adult dating, a lady and I were getting intimate. We had undressed, started kissing, caressing each other and then she started giving me a blowjob. Shortly after she started she told me to turn over and get on my knees. When I did she reached under a pillow on her bed and took out one of those white vibrators. She knew I liked anal play but we had not done much of it. She then told me to "spread yourself open for me", that alone almost made me cum! I did as asked, she gently slid it in, turned it on and began fucking me with it. She then said, "make yourself cum", did not have to ask me twice! I was almost shaking when I did and it did not take long.

Being in my 50s now, I think I have several "most memorable" masturbation moments. All different in their own way.

1- the first time I've been masturbated by a hand which wasn't mine 😃 Not being in control as usual was... memorable

2- first time I masturbated outside in fresh air in a hidden field in the countryside. Feeling the breeze on my privates while doing it was memorable too.

3- masturbating while being fingered or dildoed by a Dominatrix was really memorable too, and very intense !

I met a guy online who wanted me to come to his house, strip and then put on a blindfold. I'm not too much of a risk-taker (or so I thought), but for some crazy reason I agreed. He left his front door open and I walked in. There was a sign directing me to a particular room with a bed in it. The sign directed me to stand on the bed, put on the blindfold (which was on the pillow) and then removed all my clothes, which I did. After what seemed like several minutes I heard a footsteps behind me and someone got onto the bed with me. He began talking to me about how brave and trusting I was to come this far. Well, my cock was extremely hard at that point! I felt him reach behind me and run his hands over my ass. Then he began playing with my cock. Despite still being scared at this point, I knew I wanted him to go on--which he did until I came on his bed. Afterwards, he took off my blindfold and told me to get dressed and leave. I guess he just wanted to know whether someone was trusting (and stupid?) enough to do what he asked. I, on the other hand, was feeling terrific. I learned that I like the some amount of danger when I'm having sex.

I’m going with the first time that it happened, when I was 11 years old. I was excited and nervous at the same time, and had no clue what occurred, or why it occurred, but I knew that it was amazing, and I wanted to repeat it. Fast forward to almost 57 years later, and it never stops giving me a thrill!

It was a long ride home from an extended stay camping at the lake with my new girlfriend. She was unbelievably hot and we had only been intimate a few times before deciding to make the lake trip with friends. Circumstances did not lend themselves to sex in the tent only a few feet away from our friends, and daytime activities made it impossible to find alone time. I looked at her in a bikini for several days, in and out of a boat, laying in the sun, sitting around the campfire, and all I could think about was her incredible body. I was happy to pack up and start the drive back to civilization because it meant being alone with her and laying some serious pipe. In the car on the freeway she fell asleep with her head against the window and her very shapely breasts and legs just a short distance away. As I looked at her one had steered the car and the other began gently massaging my very swollen member inside my shorts. I didn't want to get caught, but the desire to cum was overwhelmingly strong. I kept edging myself until I couldn't hold it any longer and looking at her I must have squirted a gallon of cum in my shorts, some of it ran out and dripped on the floor. It was memorable because I managed to keep the car between the white lines and enjoy a volcanic orgasm looking at my soon-to-be wife. I had to pull in the next rest stop to clean up. After we got home we were talking about sex, and she asked me if I was aware cum had a recognizable scent. She smiled in a way that made me wonder if she knew what happened in the car on the long ride home.

Can add another now… a recent one while chatting on Zity with a certain someone, doing naughty things to one another. 🤩😇

The surprise when I first ejaculated!

My most memorable is still discovering that the 'Henry' vacuum cleaner is a very good masturbator. anyone who knows Henry models, they are cylindrical vacuum cleaners with a happy face on the side and a nozzle from a nose. by removing the long hose/nozzle and inserting one's prick into the large hole while he is sucking - Henry will vibrate you to oblivion. be careful, he can pinch you if you enjoy it too much. make sure to find the sweet spot.

At 71, I do remember a certain number of memorable masturbations. I think now about one that was very special.

I have allready posted about Maria, this medfet girlfriend I had for several years in my late twenties. I have indicated that she had set the rule that every time we were to have sex, she would impose a physical on me, allways ending with her taking my rectal temperature on her lap.

One day, she changed the scenario.

As I was about to get on her knees, she said to me: ''Today, you make me fell horny and we'll do something different. Remember, you told me about this schooldoctor who took your rectal temperature standing up in your last year of high school and turned you on so much. So, I want to repet this. If that's OK with you Honey ?". Of course, it was. So as I stood, backing her seated on the bed, she firmly parted my buttocks and inserted her glass thermometer deep into my rectum. As usual, I enjoyed this moment of the thermometer penetrating my inside.

But, then came the surprise. Maria asked me " Please turn over and face me again''. i obeyed. I had a strong erection, as I allways had when I had a thermometer in my butt. Then, without a word, as one of her hands was still playing with the registering thermometer in my rectum, her other hand seized the shaft of my penis and started to pleasure it. With a big smile on her face, she was giving me a handjob. i I was experimenting at the same time the excitement of the repeted penetration of the thermometer in my ass and the sensual touch of Maria's fingers on my penis. I was in Heaven. It felt so good. Nothing else existed, but my love to this girl.

I came and jerked a big load on my girlfriend's T-shirt. She said she loved it. The sex we had that day after some cleaning and recuperating was really out of this world.

I had several of these memorable masturbation moments, for sure. But some I'll really never forget.

I was at the age of around 10, back in my school days. Our female class teacher was quite young and really attractive. In summer, she was always wearing very light and 'open' sandals with tiny and thin straps where her beautiful and perfect sexy feet were well visible, along with mini skirts or short summer dresses. Having the fetish for nice female legs and feet - among others - I always watched her while she was moving through our classroom.

Sometimes, when I was in that mood I provoked to be placed at the last row of our school desks because I really was a little hooligan at this time. A few times as she went across the classroom and I could see her feet I couldn't help and started to jerk slightly under the desk. He was so hard already at this age and the feeling was incredible.

One memory springs to mind, i always wished i had been circumcised when i was a kid so one day i decided to tie my foreskin all the way back with a shoe lace so it was like my cock was circumcised. i decided to fuck my water wings (swimming arm bands) i stuffed it between my mattress and proceeded to fuck it... i shot so hard i couldnt move for a minute my cock was so hyper sensitive i was locked inside as my body spasmed.

i still do it to this day, tie back my foreskin so i can get some bare knob sensation as i fuck my partners ass or my fleshlight.

Not so much as mine but a first time experience. I was a sophomore in college and had met this guy I was so infatuated with. I was at his frat on Saturday night, a football game was being played, we could hear it, and we were alone on the huge deck drinking beer. I had known him for all about 3 weeks, he was feeling me up so I told him let’s go upstairs and I will give you a handjob. Now this was courage on my part as I had never given a man a successful handjob.

We went upstairs, damn did he get naked fast, I got on my knees and began stroking that thing. It did not take long, I was either very good or he was very desperate, because he when he unloaded his nuts it shot half way across the room. Good job girl.

We went upstairs, damn did he get naked fast, I got on my knees and began stroking that thing. It did not take long, I was either very good or he was very desperate, because he when he unloaded his nuts it shot half way across the room. Good job girl.

Tillie, you are wonderfull

I think the very first time is the most memorable because it was the "first time" sort was brand new

I agree with @JuleLE - the first time is unique. I was about 12 years old maybe & experimenting with trying to get a finger cut from a rubber glove over my erection, without any success. After trying for a few minutes my cock erupted a small amount of semen without me fully understanding what was happening. I knew I liked it though!!

@Tillie

We went upstairs, damn did he get naked fast, I got on my knees and began stroking that thing. It did not take long, I was either very good or he was very desperate, because he when he unloaded his nuts it shot half way across the room. Good job girl.

That reminds me of an episode on the O'Connors where they are talking about DJ taking so long in the bathroom. Darlene says he's either very good at it OR very bad at it. Dan says I guess we can't send him to his room any more to which Darlene replies, how much damage can he do with only one hand?

Getting a handjob while receiving an enema by Sherry Taylor of Sherema fame. When I came I shot a load clear over my head. She was even surprised! It was an epic orgasm!

The first time I actually ejaculated, at 16. And it was in a diaper !