Do you have a particularly memorable masturbation session that you still like to think about?

I have 2, funny enough the both involve hot tub spas: the first one was with an aunt (really a distant cousin of my father). I was about 14 maybe. My mother had dropped me off at her house for the day. She was a wild woman and the guy she was married to was an asshole that owned a restaurant and he was never home. Anyways she had a hot tub in her basement game room and she asked if I wanted to go in. I told her I didn't have a bathing suit and she insisted I go in naked. She put on her bathing suit of course. She started talking to me about school and girls. Then she asked me if I had a girlfriend. I told her no but there was a girl I liked in my class. She asked if I masturbate to her? I was obviously a bit embarrassed and she was just laughing. She said you ARE masturbating aren't you? I turned a bit red and told her yes I have been doing it. She said "Have you orgasmed yet?" I was a little confused at the terminology and replied "I think so." Of course by now I was Rock hard my dick was literally throbbing and my balls were aching as I was watching her tits float above the bubbles. She told me "you would know, it's the best feeling in the world! That's why the the men and women always scream in porn." I lied and insisted I knew everything and my dad said it feels like you have to pee etc, she laughed. We got out of the hot tub and she grabbed a towel and told me to come over so she could dry me off. She saw my super red cock and said "Wow you need to masturbate that right now!" I remember being nervous as hell, because I had never done it outside own house. I followed her directions and went to town on my member and I kind of stopped at my usual point where I felt some contractions like something was going to happen. "Keep going she screamed, faster!" So by now I was on my friggin tippy toes moaning and she was holding the bath towel beneath me and I sprayed everywhere, even onto her forearms. I think it was one of the most memorable orgasms I have had. She praised me afterwards.
The second one was at a male only Korean spa when I was about 30. I met a large group of guys from a mountain bike group I was in there and it was also a Sunday evening so it was packed. Anyways everyone was naked in the hot tub and I decided I was going to just sit in the edge for a moment and converse with ppl and just let my cock hang over the edge. As I cooled off I started to get erect. Myself and a few other went into the adjacent room which was a lounge with couches to lay on. One thing led to another and next thing I knew my towel was on the floor and I was stroking my cock with a guy on each side cupping my balls. I nearly shot 10 feet onto a few other guys that were watching on the couch! Everyone else in the room got off and we just chilled out for a while.

 

I won't mention any age because it was so very long ago. It was the first time that I ever experienced an orgasm. I was masturbating and got to the point where my penis started to tingle. Being the fact that I knew nothing about masturbation and it's effects on the human body, I was shocked and surprised by the sensation. I wasn't sure whether or not I was actually causing harm to myself, but it felt so good that I had to continue. The more I stroked my penis, the more intense the feeling got. It felt so extremely good that I kept going, fighting the fear of possible physical harm. My breathing was quickening and my muscles were starting to tense up. All of a sudden my hips and legs got rigid, my breathing was quick, short gasps. Then the intense tingling in my penis reached the apex!!! My penis started to pulse and twitch, my pelvic muscles started to contract rhythmically and my legs started to shake and shudder. At this point I pretty much lost consciousness for a brief moment. I had just experienced my first actual orgasm, albeit a dry orgasm, but an orgasm none the less!!!

 

Usually the first time a new G/F did it to me, which is always a good step forward in the relationship.

 

So many wonderful masturbation sessions! It’s hard to choose the most memorable but I have to say my first ejaculation session. I began masturbating regularly after our family moved to a larger house and my brother and I had separate rooms for the first time. When I first started, it would feel good but nothing really special until I started having dry orgasms.

Then, one night when I had just turned 14 I had a mind-blowing session. As I was reaching the stage that I usually had a dry orgasm, I began to stroke more strongly and faster. My body began shaking with the intensity of the feeling. I suddenly had the urge to pee and kept stroking. Suddenly the largest spurt I’ve ever had shot out of my cock going over my head and hitting the headboard. The next two spurts landed on my face followed by nine more spurts, each shorter.

I had no idea what ejaculation would be like and was surprised by the yellowish goo oozing down my body. After I got a towel from the bathroom that was between my room and my brother’s room and cleaned myself up, I was still hard and began stroking again. I beat off a total of five times that night and had a red, raw dick the next morning. (I soon discovered Vaseline after that night.)

 

I didn't do it a lot at home as a teen, not that was memorable at least. The best was masturbating with a friend. He and I held each other's cock. Both were rock hard and veiny. I worked the skin up and down his shaft as he had hold of mine and moved back and forth. I remember every ripple, just how his cock felt and the size of it. He came and caught his come in his hand. I watched as he pumped mine and I remember the rush of having someone else pull me. I made as little noise as I could as the come streamed out of my cock and I tried to catch it but it shot all over the floor. At times when in a secluded spot he'd want to take my cock out and pull me, so I let him. I loved the feeling.

 

I remember as a teenager one particular evening when I was extremely horny and began fantasizing about when I would masturbate later in bed. I’ve always included among a million fantasies of various kinds vivid ones of masturbation itself, both of my own and of others, and even pf the very concept.

I often turned in early to read in bed, and would routinely masturbate during that time as well, under the covers. This one particular night I was in reading position, on my back, laid down my book, and squirted a little lotion into my hand — I kept a bottle at bedside by this point in life; I used quite a bit here and there as actual hand lotion — and peeled back the covers, and with them my pajama bottom, exposing my cock which was hard as a rock, to which I applied the lotion, and immediately, with the very first touch, I ejaculated what seemed for a few moments to be an endless supply of semen. I kept pumping and rubbing, enjoying a heightened sense of ecstasy.

 

Ask me a simpler question lol
But there are a few, can't say which one the most memorable is.

Open for DM if one wants to know or share

 

I have MANY of those...!!

 

I had a vibrator on my cock right on my frenulum and I blew my load, but I was still hard so I kept it there and it felt so amazing I got in to a trance like state of orgasm like when your in the first car of a roller coaster and your hanging over the edge on the edge of your seat. I rode that ride for several minutes in bliss eyes rolling back in my head with pleasure twitching sending shockwaves through my body until I came again with several hard ejaculations.
It was the most incredible orgasm I have ever had, and I have tried several times to do it again but I have not been able to.
I will never forget it

 

Time for me to one of those cock-ring vibrators, I think

 

Look up Bodywand. I've had mine for years. Good strong adjustable vibration, long battery life. I've seen bad reviews but mine has lasted a long time.

 

Yes, many different ones.
One greatest hit is that I like to pull off the road in rural areas and go into the woods just far enough that I would be very difficult to see, but not impossible to see.
Standing up with a full erection while facing the road and masturbating and seeing cars go by is a total turn on!
Often I'll just stand there with a fully erect penis while facing the road with my hands on my hips as cars go by WITHOUT masturbating (at least for a few minutes anyway). I can show my erect penis to the world and not have to worry about it.

I seem to have wandered a bit!

 

One of my favorites was my first, when I was about 12 years old. It awakened a whole new chapter in my life, and has continued for 50+ years. What is not to like? Real sex is better, but you have to do what you have to do to keep your sanity.

 

I must say I love standing with an erection outdoors too especially where I could be seen

 

For me one of the best one was when I was in my teens I had a pic taken with a well known UK porn actress at a local sex shop she was shaved pierced with huge boobs, I had such a hard on you could see the bulge really clearly. The woman in the shop joked to the porn star that I was going to go for a wank as soon as I left, they then said they wanted to see how hard I was, I blushed and went to leave thinking they were just teasing but the older woman that worked there said to me come on love show us your hard cock, i asked if she was serious and she said she was, I slipped it out and showed them what was by now a very stiff and swollen hard-on, the porn actress said smiling wow i guess you are a fan ain't you, i nodded shyly and the woman who was working said go on love use the staff toilet here, or you'll blow your load before you get to somewhere, it's just down there, but she had a condition that i walked to the toilet with my hard-on show, and i didn't close the door, and finally i showed her my cock when i was done, i had a wank and came all over the sink in there and was still half hard walking back, once I left there i was straight to a local public toilet where a lot of exhibitionists go for a second wank

 

I truly have an arsenal of cock throbbing fantasies that I bring up in my head to get me through unbelievable masterbating sessions. From sniffing stepdaughters panties to masterbating watching girlfriend in sexy lingerie or naughty school girl uniform.
Mutual masterbating is always great to enjoy edging for hours.
Until couple weeks ago I had fantasy come true when I masterbated with two girls in my house cleaning up. It was so exciting and hot fantasizing about girlfriend and her friend in next room possibly catching me masterbating to them. I laid on bed uncovered naked with bedroom door open lost in pleasure and excitement.
I have fantasized about her friend before when both girls wore sexy little bo peep Halloween costumes one year.
Then, her friend, my fantasy, stepped in doorway and asked me question. She clearly saw my cock as I laid naked stroking my cock looking her in the eyes. I would have loved cumming right then, but she walked away. I was in another world stroking my cock to what just happened.
I will masterbate to her and the ultimate experience and most memorable masterbating session to date.
Thank you my new Fantasy Girl.

 

Another one is standing on the shore on the Outer Banks in North Carolina facing the Atlantic Ocean. I don't know what it's like today but there was a time (1990s) when you could have an entire stretch of beach to yourself.

 

Similarly: As I age, the intensity heightens...especially after scoring a buzz which makes it otherworldly. Already a FWB couple, we focus on a third, throwing variations around aloud, in turn increasing the heat between us. She loves to swallow.

 

The lady that lives next door discovered that I garden au natural. We began talking, I was not trying to hide myself she was not looking away.

Well, I slowly began to get erect, she noticed, smiled and said,
“So you’re happy to see me?”

She asked what I did to receive that condition and could she watch? And she did.

 

did you mean relieve that condition? Sounds like fun was had.