What is the craziest thing you have done masturbating?

.... and when it was over thought to yourself...WTF was I thinking??


I was looking at the thread "Have you masturbated to a pic of yourself"...and thought well..yeah...you do some pretty crazy shit when you are amped up.
So I started this thread.

I have several, but I will start it off with one:
I was first married. I got off work about 2 hours before my first wife back then and had numerous sessions in that time period, obviously.
One day I was especially lit up and was admiring my body in the mirror while going at it. And that is when it started getting weird. I am not a cross dresser, and have not made a habit of this kind of thing before or since this "event"... but I got a pair of my wifes thigh high stockings, she had numerous ones so I didn't figure she would miss a pair if I ripped it (I did). But I put them on. I am tall, and slender build so I admit I pulled that off pretty well.
So I preceded to take her full length mirror and position it across the ceiling fan so I could get the best angle possible and went to town.
It was awesome. Till it wasn't. Right after I finished I remember saying out loud to myself while hanging her mirror back on the wall and taking off the torn homes... "seriously dude? what the fuck was that about?"

 

That was a cool but crazy story. I like it. Hey whatever makes you bust your nut is what it’s all about.

 

Sucked my own cock.

 

When I was 19 I worked on a small county airport cutting grass and washing and gassing up airplanes. One particularly slow day I went out to the end of the runway to a very wet gulley washout, stripped down naked and jumped into the mud. It was a really hot day and the mud was nice and cool. I got myself good and hard and jerked off. Afterwards I hosed myself off at the IFR tower about 50 feet away. That was bizarre, even for me,

 

Love your stories Sexi!!

 

I would love to eat the banana after

 

Been there before, was just about to reach orgasm and it split

 

A new FWB at the time. She asked my size and shape a few times. She wanted to see.
Started with showing pics of the bulge, placing my cock to make the hardness very obvious.
It progressed with the underwear, then naked. I told her I sometimes cum big.
She WANTED to see, asked a few times. I gave in and filmed edging myself.
I had 4 ejaculations in one session,, she LOVED it, seeing the cock throb. One time it was just one ejaculations, but a big one.
Each thing I sent her made her go make herself orgasm. She usually did once, but I managed to have her do it a few times watching it.

 

Ashamed/embarrassed indeed, i'd been staying with friends and hadn't been laid in a couple weeks, they'd gone out for a bit and fingers just weren't doing the trick, i seen the bundle of bananas on the kitchen table and figured size and shape was good enough grabbed a nice long fairly straight one and locked myself in the washroom, it was a little weird at first but once i got it inside me it felt good and i didn't care, i went to town and just as it was getting there i felt it split and start oozing out, had enough to finish though. What a mess, i'd be a liar if i said i didn't taste it and like it though , embarrassing part was getting rid of the evidence i actually tossed it in some bushes out back, i didn't want them finding this beat up banana and asking questions lol

 

If I would have found it I would have went to a sex shop and got you a toy and maybe let me watch you play with it

 

I don’t know if this is weird or if others have done it too. As a preface, three times in the past few years I have suffered from kidney stones — which are unbelievably painful. As a preventative measure, once or twice a week, I do a kidney flush. This involves drinking nearly two liters of fluid and letting nature take its course. The kidneys disposing of all that water is supposed to dissolve any nascent stones. So far it’s worked — fingers crossed. Anyway, for the past few months I’ve been combining this activity with my evening masturbation session. After drinking all the fluid (combo of Sprite, water, and coffee) and imbibing 20mg of V, I take a hit or two cannabis, empty my bladder, and relax naked in the empty bathtub. I lube up my penis and begin stroking right away with the intent of edging for at least an hour. With all that fluid in me, of course the bladder begins filling rapidly. The sensation of the filling bladder adds to the stimulation. But long before the hour is up, the bladder begins straining under the load. This, by the way, happens at about the same time the lube begins to dry out. I try to integrate the necessary pee-pee break seamlessly into the session. Takes some concentration, but it is possible to pee and stroke at the same time. On a few occasions I’ve been able to do it without losing firmness. The sensation of pee passing through the plumbing while aroused and feeling the joy of each stroke is a bit weird at first, but it is very pleasant and exciting. And, since the pee is very dilute, it doesn’t smell. I point my penis straight up while I do this so the warm pee runs down the outside of my shaft. That feels good too. It trickles through the creases between my scrotum and thighs and runs off my ass before finding its way to the drain. It’s all good. If the kidneys are feeling especially active, I might have to take two such breaks before the hour is up. As you might have guessed, each time rehydrates the semi-dried out lube, making for better stroking after. I like to think of it as a way to stroke the inside of my penis at the same time I stroke the outside. The climax at the end of the hour is always insanely intense, and the squirt especially productive. I’m usually pretty exhausted after that and just lie there for a while, semi-conscious, for perhaps another 30 minutes with my penis in my hand, relieving the bladder again as needed, just letting it run over my tummy and mix with the semen puddle that’s already there. Sometimes I’ll rub one out a second time if I feel the energy. Then when I feel I have regained some stamina, I’ll stand up, shower off, and proceed, still naked, to the tv room to watch whatever drivel happens to be on till I drift off to sleep. Is that weird enough for you?

 

My story isn't as weird as Lester's but crazy all the same. It was after work one day. I had an hour or so to kill before I had a class at the local community college. I was looking through the latest issue of Playboy and decided to stroke one off while sitting in my pickup. With the mag on the dash and my jeans at my feet I was happily in the middle of it when my supervisor pulled up. She hollered at me from her car to get my attention. I slowed the action on my cock to see what she wanted. These were the days where cell phones were large and in bags. It seems my wife called after I left hoping to catch me before class. My supervisor offered to see if I was still in the parking lot and if so she could call my wife on her cell phone for me. So there I am getting into the layout spread of Miss whatever month it was when she pulls up. My supervisor hollers at me as she dials up my wife. I continue to stroke very slowly as she hands the phone up to me. Thankfully the truck sits a lot higher than the Saab that carried my supervisor and the call was brief. Back then each minute cost so we cut it short. I hand the phone back to my supervisor and thank her for being so nice. Does she say you're welcome and go on her way? No, she started to ask about my night classes and how I was doing in them. I stayed the course keeping my cock erect while talking with her. One good thing was she wasn't bad to look at and secretly I had a fantasy of fucking her but back then I wouldn't have stepped outside my marriage. I had no reason to. I was enjoying the thought of sucking on those tits of hers when suddenly I felt the rise in my groin indicating impending ejaculation. So I turned loose of my cock. Too late as I began to cum softly all over my cock, balls and legs. Luckily I didn't spurt a stream up in the air and must not have made a contorted face as I orgasmed. It wasn't very intense which was a good thing as I would have hated to have offended my supervisor in case she might have been. I sat there now with semen running down under my ass crack and leg as she continued to talk with me about going to night school. Finally she said goodbye and headed on her way. I had no time to clean up much as I needed to get going myself so I had to sit through class with my wet semen up my ass.