Most memorable masturbation moment

Ok, this is going to sound bad but at recess one time, I had sneaked away where I had seen some high school kids making out one time. It was a small school with MAYBE 600 kids k-12.

Anyway, I had it planned. I would wear a dress that day and go to that spot. I would take a truck and shovel and backhoe with me and "build a road" or so I would say, if I got caught.

The day came and so did recess. I loaded the toy truck with rocks and made tracks in the dirt. Then, I raised my skirt up, unfastened the tape from my diaper and started playing with myself. I had a piece of poop in my diaper but ignored it. Within minutes I had a very satisfying orgasm. I tried to refasten my diaper but didn't have much luck.

But dang that felt good.

I've written about this event before on this site, but it's been a while. At a house I used to rent, I rigged up a slanted platform, 35° or so, that let me lay back and relax with my butt hanging over the shower pan. After 2 or 3 2-quart pre-cleans, expelled in the commode, I'd lie on my board and have some fun with the colon tubes.

I have one of those bags that let you run the shower all the time, keep a constant pressure head in the bag, and let the overflow go out a drain hose and into the shower drain. Also, it was summer here in Texas and the water out of the cold tap was just warm enough for a relaxing session. That particular evening, I'd taken a Viagra just to supercharge things, did my clean-outs, and laid down on the board with my third beer of the evening beside me. I was using my 50 inch tube that night, from the old Beth Tyler site. About 5/8" diameter IIRC, roughly 15mm or 45Fr. I slipped the tube into my lubed up ass, and it went in like it had a home. Some days you can't get it deep no matter what, some days you have to work for it, and some days are magic. This was a magic day.

In what seemed like one pass, I had the full length of the tube inside me. It felt like it was clear to my cecum. I've read that's not right, that the colon is longer than that. All I know is that's what it felt like. I relaxed my ass so the water could flow out and enjoyed what felt like a warm internal massage with the warm water going into me over in my ascending colon somewhere and then flowing out.

My cock was quivering and wanting attention so I took a swig of my beer and began stroking. I edged for a while and when I couldn't stand it any longer, went for the climax. I felt it coming on through my entire body, then it hit and the first spurt of cum landed on my chin, the second one hit me in the top of my chest. It was a full-body orgasm and I didn't want it to ever stop, so I kept stroking and it went on and on. It lasted so long that it became exquisite pain and I finally stopped stroking my cock. I laid there, trying to catch my breath as the sensations slowly died away.

I took a gulp of my beer, began to slowly pull the tube out, and damn near started the whole thing over again. My body was so sensitized that I twitched and quivered for the whole fifty inches as I pulled the tube from my ass. What I wouldn't give to experience an orgasm like that again.

I should have bought that house.

Won't be the most memorable, but still on a list of very memorable, last night around 1 AM I was taken outside on the patio by my friend who is selling his house and moving to Florida next month. He was determined to spread my semen all over it, so he masturbated me until I came. Then he masturbated himself.

Earlier in the evening we were out on the patio in only our jockstraps, although i found when you show off a nice bulge, you don't stay in a jockstrap that long when your cock is desired. He sucked me while the neighbors were having a party and playing loud music. With all the tree cover, they can't see us, we can't see them. But we can hear them.

It was not me masturbating myself, but it was my 1St Love!

She sat down on a couch, with my head in her lap.

Braless she lowered her nightgown and held my head to her breast to suckle.

I was hard as a rock, as she masturbated me.

It was not a orgasm but EJACULATION!

I spruted out more semen than I ever have since then.

3 VERY long duration spurts, like "Ropes" !

My second memorable masturbation moment was when me and my wife started doing mutual masturbations ..... she shagged my penis and I fingered her pussy.

And ..... when we both masturbated watching each other masturbate.

In both cases we are fully naked.

It has to be my masturbation after having watched my freshman college roommate masturbate.

He was a good high school athlete and had been voted the hottest guy in the dorms. He was very friendly, and very straight.

He didn't know I was watching -- or I don't think he did. I had been sleeping with my face facing the wall, but when I turned 180 degrees I saw his hand moving around his crotch. There was a nightstand between us that was tall enough for us not to see each other's heads when we slept.

I recall him lifting his head to see whether I was awake. I closed my eyes just in time. I gave it a few seconds and then opened my eyes. When I did, I saw him masturbating. He had pulled the covers all the way back, and had pushed his underwear halfway to his knees.

It was light enough for me to see the outline of his shaft and cock head. He'd lift his head occasionally and watch himself jerk off, and then drop his head again. He used his right hand and I was to the left of him, so I had a nice view. He used only one hand and would briefly touch his balls before returning to his shaft. His penis was a bit longer than mine, but not a lot. He probably measured around 5.5 inches.

He masturbated differently than I did, by holding the first two inches of his penis between his thumb and first two fingers. He was circumcised, but he seemed to use (what remained of) his foreskin in ways i had not thought of. He did not use his palm.

He'd speed up and slow down, then touch his balls, and then go back to his cock. This went on for a few minutes until he started manipulating his penis faster and faster. I will never forget when I saw him stop moving his penis and pressing it hard between his thumb and two fingers. I knew he was ejaculating, but unfortunately I could not see the semen spurt out. I did watch him lie there for 30 seconds or so, before rubbing his cum into his pubic hair. He had ejaculated pretty "normally" it seemed -- it seemed to land around his navel.

Then he pulled up his underwear, pulled up the covers, and turned his head toward the wall. He just let the semen dry, I guess. I found his underwear the next day, but was surprised not to see stains inside it.

Anyway, that night, I was more turned on that I had ever been in my life. I had just seen the hottest guy in the dorms jerk off, and I had knowledge of his hard-on size and the method he used to masturbate.

I pulled back the covers, pushed down my underwear, and used his masturbation method. I don't think he saw me because his face was facing the wall. But as you might imagine, it was my most-memorable orgasm because I had just seen a hot high school running back jerk off. He was the sort of guy I fantasized about in school.

This happened during the spring semester. It was the only time I saw him masturbate when we were freshmen. But we roomed together as sophomores too, and I saw him masturbate a few more times after he had pushed back the covers. I jerked off afterward each time of course and pushed back the covers as he had. At least once, I think he saw me, but he never said anything.

One time, he brought back a young woman to the dorm. They both must've been drunk. They got in bed and made out. Eventually, I saw him push back the covers and give her lessons on how to give him a handjob! He taught her his method! I'm sure I jerked off after that too, but with a female in the room, I didn't lie on top of my bed.

Memorable moments:

1) The first time I had an orgasm and ejaculated.

2) The second time, shortly after the first time, confirming that this wasn't a freak occurrence and could be repeated at will.

3) The time my mother appeared in my bedroom door as I was sitting cross-legged on my bed enjoying a magazine that I had just procured. She just let out a quiet "Oh" and backed out. We never talked about it. However, I did notice that one of the magazines from my stash went missing after that. Perhaps to send a message, or to check it out? There were a couple of times when she was taking a bath that I heard a guttural groan, so perhaps I wasn't the only masturbator in the house.

4) Lying on my bed in my dorm room at college, I came so hard and fast that it hit the wall several feet above my head. I barely saw it because it flew so fast, there was just a "sploosh" and big blob of semen slowly running down the wall. I was hopelessly shy and a girl had been flirting with me earlier, so, naturally, instead of pursuing her, I went back to my room to masturbate. Sheesh.

5) Quite recently, I was on an overseas business trip and, not being able to sleep due to jet lag, spent most of the night edging while watching porn. When I let go, I had the most intense, toe-curling, full body orgasm that I had ever had.

I think my most memorable time i masterbated was the fist time a came with somthing big in my butt. I was about 14 or 15 and I had found my mom's toys and she had this glass dildo with a big ball on the end and it took me a while to get it in because it was so big but once it popped in and I edged myself for a while with it in I came and it was like a whole body orgasm I shook and shot cum all the way to my own face and after I like passed out lol.

The most memorable orgasm I ever had from masturbation was when I was on vacation with my family when I was in high school. We had spent the day at the pool and I was super horny from looking at all the sexy girls in bikinis. Our bathroom has a hot tub in it and that night I sat in it and let the jets caress my hard cock. It only took a minute or two and I busted the biggest and best nut I’ve ever had. The orgasm was so long and so intense that I actually cried out. Immediately my mother knocked on the door to ask if I was okay which kind of killed the mood.

I'll give two.

For masturbating myself: several years ago I tried my first prostate massager. I was using that, along with stroking myself while engaging in some self-stethoscope play. I think it took maybe 10 minutes to achieve orgasm, and it was VERY powerful. I don't think its the strongest one I've ever had, but its where I really started desiring anal/prostate stimulation as a regular sexual activity. While I knew I liked my rectum played with previously, I didn't particularly "crave" it until then.

My biggest orgasm ever from masturbation though was during a play exam some years ago. My male play doctor hit all the right buttons throughout the exam: lots of auscultation, EKG, abdominal examination, and then did a pretty extensive genital and rectal exam. After the rectal exam (all fours), he had me flip to my back and squirted a bunch of lube on my penis (which was already mostly erect) and inserted his gloved fingers again into my anus. He told me to relax as he began stroking me, which was a light to the touch and slower motion. I lasted maybe two minutes before I had the most mind blowing orgasm ever and ejaculated onto my chest and the exam table. I definitely yelped a bit with how strong it was. My play doc saw a visible heartbeat too and I felt my heart pounding, and proceeding to listen to my heartbeat for a couple of minutes following with how thumpy it was.

My masturbation (post) was truly unique. Im 75 yrs old,and in 1970 I was discharged from the army, I was getting married in 2 weeks and was getting VA disability, and attending University of Houston. My fiance and I were not strangers to sex,we had been bumping bellies since 1966 (she 16,me 19 at the time). I finally was able to buy my dream car.......a 1963 Ford galaxie convertible 427 with a cross-bolted main, and 2-4 bbl carbsI had to special order it....I was still in Viet Nam....my father still couldn't understand how ANY car could cost $5000. Oh well. This car was a 4 speed, and had a floor shifter from the factory. ANYWAY......My soon-to-be wife and I went to the drive-in theater that night, because of the intended "ride-the-pony" thing, I had to put the convertible top up for privacy. The next day, it was stiffer than normal to shift. I put the top back down (my mom and fiance) liked to sit back there and chatter and make wedding plans. ANYWAY, I removed the console and removed the other stuff.............and behold!!!!! I found a pair of black bikini panties caught between the 2 shift-rods. At that time my dad came out of the house with 2 cold beers....he looked at what I found and said....."I told you to change that torn , rubber shift boot"....".Goddamit, I told you that it would eat those kind of panties" Needless to say,my mother and fiance made a quick exit........asking:"Susan,would you give me a hand in the kitchen?"Masturbation played a part in this missive. ??? better believe it!!!!. bob.

l

Hhh

Remembering once when my wife was fingering me while I did it. Must have put a lot of pressure on my prostate cuz I unloaded a lot and it hit my chin. Normally I was never a big shooter, but I was that night!

My masturbation (post) was truly unique. Im 75 yrs old,and in 1970 I was discharged from the army, I was getting married in 2 weeks and was getting VA disability, and attending University of Houston. My fiance and I were not strangers to sex,we had been bumping bellies since 1966 (she 16,me 19 at the time). I finally was able to buy my dream car.......a 1963 Ford galaxie convertible 427 with a cross-bolted main, and 2-4 bbl carbsI had to special order it....I was still in Viet Nam....my father still couldn't understand how ANY car could cost $5000. Oh well. This car was a 4 speed, and had a floor shifter from the factory. ANYWAY......My soon-to-be wife and I went to the drive-in theater that night, because of the intended "ride-the-pony" thing, I had to put the convertible top up for privacy.

I bet you wish you still had that '63 ........

Couple come to mind, both when I was a teen:

1. Was having phone sex with a gal I had never met (one-way phone sex since she had no idea what I was doing). We were having a casual conversation about physicals, one I initiated by telling her I was nervous about an upcoming physical, not knowing what was in store for me. Asked her about her physicals. She proceeded to tell me in detail about her latest doctor exam (naked from the waist down, feet in stirrups, speculum in vagina, the whole nine yards). I asked her if she was nervous and she said no, just embarrassed. My dick got so hard and I was breathing heavy at one point that she asked me if I was OK. I made a mess all over the place without her ever knowing what I was doing. I think. Or else she was a fantastic deadpan actress who knew exactly what she was doing to me.

2. My bedroom on the second floor overlooked the neighbor's front yard in the apartments across the way. A lady, maybe late 20s, early 30s, was sunbathing in a bikini. After ogling her for several minutes, I couldn't take it anyone and just pulled out my cock and started stroking it while spying on her. I came all over my carpet. Cleaned it up but can't recall if it left a stain.