Crazyest masterbation story!

Tell me your crazyest kinkest masterbation story! Sitting here alone wanting to know!

 

I have nothing crazy, sorry.

 

Not too crazy, but a few years ago I was extremely horny at work. When I left for the day I had a be 35 minute drive home. O decided to stroke all the way there. I edged almost all the way home and right before I pulled into the driveway I shot a huge load all over my hand and the steering wheel. It was pretty hot!

 

I get my kinky kicks riding my MTB naked; it's the stuff of legendary, raging boners caused by the normal movement of the tackle up and down the saddle -- even though it is slippery enough to be like trying to ride a bar of soap! A stop is often needed for a wank, then continue on for a while and repeat. Probably not "craziest" in the strictest sense, but something too few people have experienced and which I think they should because it is so damned erotic.

 

When i was in my late teens i babysat for this young couple , one summer they went on a two week vacation and asked me to house sit for them. It was the first night and they called and needed me to get some phone numbers they'd forgotten, they were sure they were in their night stand so i went and checked and they were there, however there was also a dildo and two vibrators. At first i was a bit shocked and just closed the drawer, I've always been exceptionally horny and even when having regular sex i masturbate at least once a day, over the next couple days i couldn't stop thinking about the toys, then curiosity got the best of me as i was playing with myself, i really wanted to try them and i remember i had a few just in case condoms in my purse so i told my self if i put condoms on them it wouldn't be as bad and i went and got the two vibrators, first one was just a generic smooth and straight one and I'll never forget that first time i inserted it, but the second one was the game changer, i was honestly a bit intimidated, it was one of those curved two headed G-spot/clit vibes, i put it in first then turned it on and 5 minutes later i was having an orgasm like never before, it left me trembling for probably 10 minutes and my knees were weak afterwards. I was a bit embarrassed that I'd used another woman's toy but i couldn't help but use it several more times, it took a few weeks to work up he nerve but i bought my own with the money i made.

 

Unlike Biggles_Nude, Sorry Biggles! I was wearing bike shorts on a ride in Sedona Az. I was enjoying the ride and one of those open top Jeep tours drove by me on the same trail. I was riding at the same pace of the Jeep (They go Slow!) and there were 4 girls riding in the back watching me ride, smiling at me and telling me to pedal faster! It was a hot day and they were wearing Bikini tops.. I think they were college students? Anyway, every bump the Jeep went over I got a show of their tits bouncing everywhere. It was a pretty good show! I rode for about 15 minutes and caught up to them at an Overlook. They were commenting to me about my nice ass in my shorts. I was starting to get a bulge and sat on my seat with my water bottle hiding it. Something inside me wanted them to see it. I told them that I liked their tops during the Jeep ride and gave them a smirk! They laughed and giggled at me! They were with the tour guide so I didn't flirt too much and didn't want to distract their trip.
After a few more minutes, they hopped back in the jeep with the tour guide and headed back. I couldn't handle it anymore! My bulge was getting bigger thinking about them. I had to carry my bike up the hill behind some Scrub Oaks and take care of what was happening in my bike shorts. I was sweaty, and had pre cum all over the crotch in my shorts. I didn't need any lube. I stood there and stroked for a few minutes hiding behind the trees watching the Jeep drive off in the distance. Luckily, no other Jeeps or bikers came up the trail while I was pleasing myself. I had to rest a little longer before I headed back.

 

A view years back I was on a business trip to Japan. I love that country and its people. The sexual moral is so completely different than we are used to in Europe.

Anyway I had visited a few sex shops one day and in one of these shops you could buy dolls which were around 12 inch tall with everything you could expect from a sex doll.

It was actually a female action figure from a Hentai/Manga comic. It was sort of a masturbation sleeve which looked like a doll. It had a nice pair of titties and a cute ass. Most important a flexible pussy and belly you could at least push your cock in for almost four inches.

Sadly enough I didn't get the chance to try my new toy out. It wasn't until I was back I had the opportunity. Because of the time difference and the change of a jetlag I decided to head straight to my office before I went home. It was at the beginning of the evening and it would only take a hour or so to get things done and then I would go home to spend a week with my wife and 2 daughters.

I placed the flash drive in to my computer and started to upload the files that were required for my colleagues to make a acceptable deal with our Japanese clients. When I was waiting I thought back at my new toy.

I immediately started to get hard (trying out new sexual things really turn me on) and took the doll out of my suitcase. It was wearing a princess dress. I knew I was going to take a huge risk. But I was extremely aroused and wasn't thinking straight anymore.

I pulled the zipper of my pants down and pulled out my extremely hard cock. I quickly lubricated the doll's pussy with my tongue and and pushed it on to my cock. It really felt tight and I didn't need much time to feel my orgasm approach.

I was fearlessly fucking that doll when all of a sudden the door to my office opened. It turned out to be the cleaning lady. With the doll on my lap facing me. I greeted her. Luckily I hadn't removed the doll's dress so there was nothing out of the ordinary for the cleaning lady to see.

The only unusual thing was that I had a doll on my lap. She immediately thought I had bought the doll for one of my daughters. She stroke the doll's hair and pulled it a bit up. At that moment her cellphone started to ring and let go of the doll. The indescribable pleasure the knowledge of getting caught was so overwhelming that I filled the entire doll with cum.

Lucky for me the cleaning lady didn't notice anything. She was to busy with her phone call and shortly after left my office waving goodbye still busy with her conversation on the phone.

That was by far my craziest masturbation session.

 

When I was about 15 or so, I was alone in the house and was seized with the urge to masturbate in the family room. I did, and when I was done I noticed that the curtains were open. Oops. Never heard anything about it (but who would say anything?)

 

Maybe you got lucky and no one passed by?

 

I'll never know

 

Ominous...

As for me, I don’t have any super-super crazy stories. But I did almost get caught once...

 

Where I lived two houses ago, it was a two story Victorian with several sharp gables etc. Houses all around us.
In my daughters bedroom you could walk out onto the roof in the back of the house...but still houses all around.
Anyway when up there once I happened to notice in a corner you could sit/lay there and no one could see you. Sooo...I pulled my jeans down and started to go, and ended up taking my shirt off and using that to sit on, pulled my pants all the way off...laid them out and laid down...buck naked in the middle of town...people walking around, cars going by... while i am up there going at it.

 

Way to go, girl!

 

When I was about 14, my parents were out of town during a weekend. And had the house to myself. I was watching a porn movie naked. and started to masturbate then all the sudden my dads secretary walk in, and caught me. She had on her bikini and was going to use my dads pool. She just smiled and went to the back yard. I got dressed and went out back to talk with her. She told me that my dad wanted her to swing by to check on me. She apologized for walking in on me and told me never be ashamed for doing that, it's very natural thing.

 

I was on vacation with my cousins and two of them are unbearably sexy as hell!! I've always been attracted to them. After seeing her in her bikini, I could not take it anymore. I went back up to the condo, found her luggage and and started playing with her panties. I found the sexiest pair and jerked off right on to the crotch area, I didn't last long especially thinking about it all being right up inside her. I will never forget it

 

well let's see... I was watching a bi/gay porno video of faceshots (I was in my early 20s then), dark room, I'm on the floor beating off. my cousin who was visiting at the time staying at my apartment (he was maybe 19 or 20) comes home and walks past the room I'm in, drops his backpack and comes in, undresses and starts jerking off. kind of awkward at first but we're like brothers anyways so it was fun.

guess it's not really that "crazy" as

 

We were at a family wedding out of town. A bunch of the family staying at my wifes aunts house. My sister in law was sleeping on the couch, my mother in law in a recliner. My wife, brother in law and myself slept on the floor in sleeping bags. My sister in law was right above me. I awoke at around 5 am and saw her lying uncovered with her nightgown up enough to be showing her panties. I stared and started to masturbate. I saw her move a few times and I've often wondered if she knew I was awake and was giving me a show or just innocently sleeping. But I did enjoy it but not the wet sleeping bag for the weekend.

 

when I was 17 me and my girl drove to my friends place. In his driveway she jacked me off and my cum hit the windshield

 

When I was 14 I went with my parents to a family wedding, where staying at my grandparents house. One morning I woke feeling the need to masturbate, so I lay eyes closed and rubbed myself to orgasmic. When I had finished I looked over and saw my cousin looking at me from the other bed in the room, she laughed and said "I guess you forgot you were sharing a bedroom".
Give her regard though, she never told anyone about it but she still reminds me from time to time.

 

In hi school the boys locker room had a window with bars behind. Outside the window was a stairway that was not supposed to be used by anyone. I was alone and changing my clothes just out of the showe and about to put on my underwear when I noticed a girl a few years younger than me walking down the stairs. She stopped and smiled at me and was looking at my dick. I instantly got hard and opened the wood sash window.She stood there smiling. I began to jack off standing at the window. I came very quickly and shot my stuff on her school uniform. We never met after that incident.