Crazyest masterbation story!

Crap. More fun with the drugs I didn't do in college....

 

I posted mine on another thread responding to a question about first times. Don't want to be overly redundant, looking for a thread about second-craziest time.

 

Well, when I was in my late twenties I used to sell drugs. I ended up with a younger female roommate that needed a place to stay for a while. My friend said she was pretty, like to party hard and would do chores and clean my apartment as rent. After a couple of months she figured out I sold party favors. So we would party together occasionally. She liked to get geeked out and asked why I wouldn't geek out with her. I told her it made me super horny and all I could think about was having sex or watching porn and masturbating for hours. So one night I decided to geek out with her. After a while, I told her I was going to watch porn and probably masturbate. I said she could stay in my room while I'm in the living room. So there I was wearing only a tank top and masturbating. After a while I called her to see if she wanted more party favors. So we got more geeked out, then to my surprise she went into my bedroom and came back wearing only a t-shirt. Then she sat down on the other end of the sofa I was on and she said doing stuff made her horny too. She said she's never really watched a guy jerk off and Said she'd like to watch me if that was okay. So I said sure, I'm not embarrassed and lubed up then started stroking it. She started masturbating a little while after me. We spent the next 6 hours geeking and masturbating. After that a couple times a month we would party and play together until finally after about 9 months of her living with me, we started actually having sex, whenever we were bored and horny or didn't have a date for the night.

 

Maybe the time I was driving and had this aching erection that was not going away and I was not able to ignore.
Cock out of underwear but still in my sweatpants, I stroked myself over the pants.
I waited for a big truck to go by to continue and not long after I made a mess in my pants.
The thing was, I had a long full body orgasm that nicely lasted long enough.
When it was over with I realized that in the moment I had slowed down to 40 km/hr (25 mph) on the highway.

One I love reliving, visiting this cock edging loving woman. She gave me several orgasms and made me squirm and moan a lot, kept close to ejaculate for almost one hour.
When it became too strong I said I could not hold it anymore
I squirted hard, three big strong squirts that shot at least 3 feet from me sitting on a low couch. She had her hand ready to catch my cumshots but they shot past her hand. Her jaw dropped and she squealed, and best of all she kept working my cock until I was done.

 

My friend had two very pretty older sisters. (I use to hang out there quite a bit). I wanted to have sex with the younger one of the two. She was three years older than me, but seemed to enjoy me being around.

Sometime down the road she ended up giving us a strip show omg it was the best thing ever, now mind you I'm only a teen. She let me grab her tits and she was grabbing my dick, but never lead to anything more.

Being a horny teen, I would jack off thinking about her all the time. When I was over and she would fall asleep I would think about going over to her and jacking off right near her face, or even try to cop a feel.

One time I had to use the bathroom, and found that she left her bra in there after she showered. I quickly got hard grabbed the bra, and started to smell and feel it. This was the first time I've ever had my hands on a bra. I got so turned on I started jacking off. It didn't take long before I shot my load into one of the tiny cups of her bra. Then I thought shit! I just blew a load into her bra, what am I going to do with it? Lucky for me they had a laundry shoot in their bathroom. I tossed it in there, and not sure if she ever found out.

From that day on I've had a fetish for small tits and the bras that "support" them. I've even gone as far as stealing some from her to take home and jack off to. I'm sure she noticed some bras missing.

 

I was out walking throughout a big Manor House and forest in the summer with two girls I knew well, we got to a small round pond quite a bit off the beaten path when one girl said we should play truth dare, after a few funny dares it got more serious and one of the girls dared me to strip and whack off, I was pretty shocked but a dare is a dare, so I was ok how long and the other one said till you cum, we wanna see you cum, omg I thought, as in reality I was shitting my pants as it’s a very private and exposing thing to share with anyone never mind two girls in broad daylight. But I stripped naked as they watched smiling and I knew then they actually liked watching so I started touching, just fuck I felt ever so embarrassed but after a while knowing they liked it I got closer and closer till my breathing got heavier and I started to moan then came. It was so crazy scary, but also bloody hot to be so open and exposed lol

 

In my younger years I had a couple times dropping acid as well. There were a bunch of strange things that had happened throughput my tripping days but sexual encounters, there was only one while tripping. We didn't get the acid until it was actually to late, but I did it anyway and was dropped off at home. I was probably 16 without a car of my own. I had walked in the house and I started to giggle with an occasional laugh. I walked passed my mother on the couch and I didn't remember seeing her. I went up to her toom, which I was still sleeping in and undressed and got naked. Still giggling and restless I snuck in my sister's room and yes, I was naked. At night I was always naked, and did move around at times. I said that I was wanting to give her a gift. I was in her room and we were talking about how I was going to fuck her and her friend and I jacked off on her and as I left, I turned her light on, to find out that I was in her room completely alone and our sexual talk was in my head. So I went back in my moms bed and turned on the TV and it was a stupid dinosaur movie and I couldn't stop laughing. I had been telling my mother that it was funny and I would probably shut up after I get to fuck someone, and I jacked off on her. When the dinosaur thing ended there wasn't anything else on any TV back then and I turned iff the tv and saw that I was alone again. Wow I was really tripping. I didn't see the mess I made jacking off either. I wondered to the kitchen and got some milk and I was getting a drink and looking at my cock getting hard. I wasn't sure if I was imagining it or what, but since I was alone, I started to jack off. I was going at it and enjoying the motions before the big blast and at that time we lived on a lakefront property and had a 8 X10 window facing the water and I opened the curtains and was jerking off as I looked at the moon glistening off the lake. I was slowly stepping back to take a seat as I started to cum. I started breathing heavily and I was stroking my cock faster and just a couple seconds before I was going to get a nutt off, I sat down and leaned back and I started to cum all over my chest and in my hair and face. I was so waisted I had shoot cum in my mouth and was hacking from that happening and still stroking my cock and cuming on myself without getting as much distance and I didn't stop hacking or jacking off and I lost all sound while I hacked up cum and coughed vigorously. Then I heard her voice and she was trying to get me off her legs so she could help me. She was getting out from under me and she saw my hand still stroking my cock and she had been touching me and she had my cum on both her hands and legs and she said to stop shaking it, because it was spitting all around us. It was mom and she woke up to me hacking and she was trying to assist me with it and she ended up being sprayed with my jism. She finally got up and turned on the lights. She said to stop pulling on it. Which she told me that I didn't stop. She said she was laughing when she realized why I was hacking and that she had laughed so hard that she was having trouble helping me do anything. She said that she eventually got me up in bed and she still couldn't get me to stop stroking myself. She said that she kept holding my dick to keep me from getting it hard again and cuming on her again. In the morning which was around 6pm for me. She woke me up and told me to get something to eat. I got up and went to the kitchen and sat down to eat and she started to tell me every detail about what she saw me do8ng and what I was asking her to do. If she thought I was on acid, she would have flipped. One of her friends told her that sombody was slipping someone something and he probably drank it. Because she had told her girlfriend what I was doing and what I was wanting her to do. Turns out I was a motherfucker. LOL

 

got another one. when I was still living across the river in Vancouver there was this abandoned city-owned park just outside the lower east side, above a quarry, people would hike or ride their bikes up there. it was popular for a while at night with the partiers and drunks. it had a huge 20't tall grassy dirt mound that blocked a ravine on the other side. the ravine was a popular orgy spot because it was relatively wooded and the area next to it wasn't developed yet so it was pretty secluded and the mound shielded it from fht east wind coming off the columbia river gorge. i used to ride up there a lot and beat off if I was in the area. hell, I even more than once spotted people up there fucking out in the open, in the park since it was so little traveled back then. so one day i went over the ravine to take a piss and beatoff, then this other guy, probably 7' tall, late-20s, super athletic dude comes over to take a piss too, well he sees me jacking off and starts to undress and jack his probably 8" uncut BBC off too. (I didn't have a shirt on since it was about 100 degrees that day but had some jeans on and a jammer or bike shorts I think, and sandals.) next thing we're both totally naked and stroking each other off and i eventualy giving him anal, got him to shoot his load a good 10 feet away or so. we had a few more "dates" in the ravine after that. that was an awesome summer with the months of unseasonably hot weather and a fuck buddy that i met just by random chance.

think this was like 2015 or 2016, one of the last big el nino years.

 

I remember when I was a kid about 14 or 15 years old we had a next-door neighbor and their daughter was probably about 19-20-ish. She used to sunbathe in her bikini pretty much right outside my bedroom window. She would untie the top of her bikini and lay on her stomach and I would watch her hoping she would forget and sit up. But she never did. She was like centerfold material blonde beautiful and she had the entire backyard to sunbathe. On one side there was quite a distance between her house that neighbor and their yard. The back was wooded. But yet for some reason she would choose to sunbathe right outside my freaking bedroom window!

After a few weekends I would stand by my window and start stroking myself to her. The first time I must've shot out a quart of that thick, hot, white fluid out of my boner! Wow it was so intense. I got to the point where when I saw her outside sunbathing I would just run up to my room pull out my already stiff penis and rub it till ecstasy.

A few times whhen outside I would see her getting in her car or walking to her house and she would see me and just give me a smile and a finger wave. I could barely wave back because I knew what I was doing watching her and I guess was a little embarrassed by it.

I knew what I was doing would be considered "dirty", but just couldn't help myself. Years later I thought about that whole situation and wonder to myself if she actually knew what she was doing or not.

 

Between the ages of 12 and 22 I had a pretty insatiable horniness about me. Not sure if they were something wrong with me or not but I was constantly ready to masturbate and cum. I would have a Boner if a stiff wind was blowing. When in high school there were times where I'd be jerking off three or four times a day. Probably would've went for five or more but I got to the point where I either was having a hard time getting stiff or I had just nothing left to shoot out of the end of my dick.
I remember sitting next to a hot girl in class and then when the bell rang having to run into the boys room in between classes and use the standup urinal and rub one out. Even walking home sometimes I would have to stop off a fairly busy road where there were some really tall hedges and I would just blow a load into the hedges for relief. At the bowling alley when I would go to watch my father bowl and one of his friends daughters would go to watch her father - I would have to go into the bowling alley bathroom and stroke a a massive shooting a load on the back of the stall door.

Not sure how the plumbing in my parents house survived with all the sperm I dumped into the shower/tub and toilet. Then of course my bedroom was like the masturbating palace. Sheets had to be stained although many times I would jerk off onto pictures from Penthouse or other magazines.

It was a confusing period in my life. Was always so Randy and it was almost like the mere sight of a female would set me off and I would have to take things into my own hands almost anytime, anywhere. I was so shy and backwards which made self satisfaction sort of my only escape.

Gees. First time I have ever admitted to any of this publicly. Honsetly, Feeling a little queasy about it ...

 

Long long time ago while my wife was out. I had a few drinks when watching porn on the TV (yes in the days of VHS films) I fell asleep on the couch naked after wanking.
She came back home with a friend and found me lying on the couch naked with a hard on.
They had both been drinking, a lot, she woke me up by wanking my cock and had put the film on to play.
I was so embarrassed but I was told they wanted to watch me cum.
I lay back and did as I was told, instructed how to stroke my cock and play with my balls. I had to stand in front of them and stroke real slow, edging.
They both had their hands inside their panties getting themselves off.
After ages I was allowed to cum then fed my own cum.
I still get turned on by this memory although now wanking in fron of my wife is quite commonplace.

 

That's what we call "youth".............

 

Nothing too crazy here.
The masturbation was done by a woman’s hand.
We gad met other times before and the first time it was highly obvious she was an avowed cocksucker who loved swallowing and keep going for as long as she could. I loved it.

But this one time I truly wanted a handjob when it was my turn. First she asked if I preferred a blowjob but I reassured her I wanted a handjob.
Looking back it was her who wanted to have my cock in her mouth.
She stroked me real good although she asked if I wanted her to suck it again.
The shaft was tingling and feeling super hard.
When I started moaning she started bending down to take me in her mouth but I told her NO, that she keeps stroking my cock very fast the way she was doing it. I saw the disappointment on her face but a few seconds later it was replaced by shock and surprise.
When the first cumshot came out it really shot high, a generous squirt that shot high and fell back on the bed beside my head.

She jumped and flinched in shock on the first shot but didn’t miss a beat stroking more similar squirts, amused at how hard she made me cum.

 

Maybe not crazy, but sure as hell embarrassing.

We were visiting the in-laws and her sister and her husband. We were put upstairs in one of two spare bedrooms. After dinner Julia and I went up and were sitting up in bed relaxing and reading with the lights on. She surprised me by reached over and pulled the covers down and slowly started jerking me off. I had noticed the bedroom door was cracked open slightly but, given my huge erection, frankly didn't give it a second thought. As usual she eventually leaned over took me in her mouth and gave me perfect long deep strokes while massaging my balls and didn't miss a single drop as I laid my head back and ejaculated.

The next morning I overheard her and her sister giggling in the kitchen. I knew it couldn't be good. Later I learned that her sister, on her way back from the bathroom, had gotten a close-up view of the whole thing peeping through the door. Julia confided in me that her sister really wanted to watch me ejaculate freely, as Julia was always bragging to her about my ability to have powerful orgasms and 'cum 4 feet in the air'. So, that night we did exactly that, Julia had the perfect combination of hand and mouth as usual bringing me to another great orgasm...............and yes................I did.

 

The most recent one that comes to mind. It had been a few weeks, I was HORNY.

Ok, so first things first I’m extremely multiorgasmic. I finally had the opportunity after a few weeks, and a few hours alone. I jumped onto my bed after plugging in my magic wand and started thinking myself off to orgasm. Writhing, giggling, crying... I orgasmed 20-30 minutes hands free this way just orgasm after orgasm. I started laughing, knowing I was going to get my magic wand out next aware of what’s probably going to happen.

I went into instant orgasms... I mean screaming, convulsing, eye-rolling, shrieking nonsensical insanities. I just writhed and screamed and blabbered and made crazy grimacing faces.

I was still being excessively way too loud no matter how I try to keep quiet. But I couldn’t find my trusty rubber ball gag, so I duct taped my mouth completely shut. I proceeded to have VERY prolonged orgasms continuously.... bucking my hips and arching my back and contorting my face and screaming and making who knows what kind of noises. The duct tape made me snort and grunt and I was still loud, but not so much that the neighbors would get worried.

I was inadvertently covering my mouth and nose with my hand and with the duct tape I couldn’t breathe as I was pinching my nose shut. I couldn’t stop myself from pinching my nose so I was in the erotically humorous position of trying to breathe while orgasming my brains out. I reached the peak of orgasm and remain at that peak for a loooooong time.

I convulsed and flopped around and writhed in this electric orgasmic pleasure that went throughout my entire body. The amount orgasmic sexual pleasure I experienced is INSANELY extreme.

I did this for hours until I collapsed in exhaustion. I usually have marathon masturbation sessions like these several times a week, but this is the most recent experience that comes to mind.

 

Yes I have story.. Not story it's real and I started masturbation from there only...

So I was 16yr old and started thinking horny things and get erections on my penis but I couldn't do bcoz somewhere in my mind I feel panic if it's right or wrong so I stopped and couldn't do anything.. But one day it happens and first time I see my heavy load and it feels more good and happy ,first time... So it started when I went to spend time on vacation to my aunt's house. It was summer and we have only one shower room for all and we used to hang dirty clothes over there too. So when I gone for take bath I just see used bra and panty there which was for washing, and I can't stop my self to touch it. Bcoz somewhere I like my aunty bcoz she just very younger and married only few days ago,... Her breast are very large so I imagine her breast while I grab her bra and started feel horny... But when I touch her panty and I want more so I smell it.. And trust me it's first experience that I imagine and smell her pussy... Then my pens become harder and I started rubbing on bra and panty.. Till I shoot my cum on it.. And that first time I watched my heavy and smelly white load on her underwears.... And it becomes my one kind of masturbation fantasy... So I don't know that on how many bras and panties I used till date...... Mm

 

A few years back I had one of those gravity inversion boot setups that I used to stretch my spine and build up my abs. At an early age I found that I liked the taste of my own cum. So one day when I was home alone, I got totally naked and started my ab crunches while hanging upside down. I jacked my cock in time with my crunches, and shot my load over my face and chest. I did that a few more times when I got the chance.

 

It was in a dingy cabin. I mean DINGY!
It wasn't the end of the world but you could see it from there.
I had never masturbated in front of anybody before.
I was with a girl who was a summer fling.
She wanted me to do it.
She was naked and lying on a very small bed.
She put a towel over her face so she couldn't watch.
I knelt between her legs and played with her pussy until i ejaculated all over her body.

 

She was a pretty girl living dangerously in a cheap part of town. Nobody had any money, I worked at a restaurant nearby and played guitar in a band most nights for a few bucks. She had ‘dates’ with guys in nice cars. After her date she found me sitting by my door, which was near her door. She told me stories, I got hard and one evening I excused myself, told her id be right back.

Innocently she asked where I was going. I told her blatantly, that after hearing that story I was going inside to masturbate. She giggled and asked if she could watch. I let her in, she sat on the sofa, I stood a few feet away, pulled my pants off and started to stroke my cock. She had a smile on her face, she didn’t say anything.

When I came she giggled, I stood there afterwards with my cock hanging out for a minute. I put my pants back on, she asked if I ever went down on girls. I said I did. Without a word she spread her legs, I could see her pussy.

“If you eat my pussy, I’ll ride you later when you get hard.”

I knelt between her legs, I could smell the semen from her date. I only hesitated for a moment, I had jerked off to this girl so many times, maybe this time I would really have her. I licked her pussy, sliding my tongue inside her and sucking her labia, before working on her clit, she tensed her legs and moaned, I had her going.

She came hard, gushing and really wet. She said come here, we kissed both of us had semen on our breath. I began to wonder if she was just going to giggle and go home or ride me like she said.

Without a word she stood up, took my hand and led me to my bedroom. Due to my cooking job I was able to make her an omelet in the morning. I still make her cum when we make love, but I think it was the omelet that won her heart.

 

I was home alone no kids no wife and was horny has hell had no clothes on and wanted some, I got in my bed and started to play with my self rubbing my self and my nipples which I love and started to moan a little when all of a sudden I sall my daughters friends walk in my room he is 20 and gay and said hi sorry to bother your fun but I was here to pick something up for your daughter, I said ok (keep in mind I’m still naked and hard also horny ) he asked if I would like him to join me in bed (was not the first I have been with a man ) but this one is like family to me he said he would not say anything to no one it would be our little secret as he waited for me to answer he got undressed which now made me even more horny because he was cute so he ended up staying for about three hours took a shower and left ,it was the best night of my life never forget it

 

WOW so cool