What's your best jack off story?

This happened to me at work once... There were a couple older ladies that I worked with that on occasion would talk about sex with me. I use to tease them that I was great in bed because I had a big penis, and knew how to use it. They kept telling me that they didn't believe me and that I would have to show it to them.

Well, eventually, I called their bluff, and I got both of them over to one of their offices..shut the door, and I showed them my cock.

They told me that they wanted to see it hard too. So, I started jerking it for them..got it hard, and then one of them started talking dirty to me, and wanted me to cum..so, I leaned back..jerked off till i came, and blew my load all over my stomach for them.

The lady that talked dirty to me..came back for more..and eventually sucked my cock, and I fucked her a few times.

I'm a pro massage therapist so I can't give happy endings. And I don't this guy named John I'd know for months and I was in lust with came into my Chiropractor's Office. We went into my massage room and I gave him a massage we were so hot for each other and I did my best not to jump him only massage table....he was very respectful and did everything in my ore to br respectful.

Then he asked me out for sushi and after we fucked in his truck in broad day light. Then when no one was in his office ofbthe company he own we kissed ate each other fucked vaginally and anally. We ending up being in a relationship forv3 years. The sex was always electric!!!!!

Anal

My best jack off story...wow...I have so many. I can say that my best orgasm was when I was 16 and playing basketball for my school. The girls and boys team rode the same bus to an away game and I was up in the empty press box watching the girls play. I had a major crush on one of the players. She had an amazing rock hard athletic body, but also had huge tits. I overheard her say on the bus that she had forgot her sports bra and was going to have to play in her regular bra. Well, her tits bounced every which way but loose and since no one was in the press box, I took out my cock and started stroking it. I was leaking precum all over the floor and I was doing my best to hold back my load. I couldn't hold it anymore and I quickly found the farthest bathroom from the gym, went into the last stall, dropped my shorts to my knees and started jerking off. I instantly came and it's the biggest load I've shot in my lifetime. It hit the wall behind the toilet, all over the back of the toilet, the toilet seat, and the last few squirts hit the floor. I could hear it splattering as it hit hard surfaces. When I had finished cumming, I thought I'd be nice and clean it up, but there was no toilet paper...in any of the stalls. No paper towels either. Nothing. I just left it. Words can't describe what a huge load it was. I've never shot one that big since, even when I didn't jerk off for 5 days trying to cum that hard again.

My g/f and I are in the 69 position,instead of eating her pussy I lick my middle finger and glide it into her asshole,she squirms forward and sits up squating over my dick which is starting to get hard. She exclaims "So you want my ass?" and proceeds to shit on my lower belly and my cock and balls. She then begins smearing her shit and seeing my cock rise she begins masturbating me with her brown offering. As I moan and start cumming I see it cover her hand and mix with her poop.As the cum dribbles down she lowers her head and starts licking my shit and cum covered dick clean.I am so overwellem I grab her hips and pull her dirty stained ass down to my mouth and I lick her clean.We both collapse and after a while we get up and go shower together without saying a word about what happened.We look at each other shyly and knowingly as to the depths of depravity we had sunk to.I am looking forward to our next encounter.

I met a guy when he was over here in Ireland from New Orleans working on similar projects to mine. We got on well without being overly friendly. I could see he had similar interests and was a discreet type, most definitely not the sort to gossip or blabbermouth. The way he mentioned jacking off gave me an idea that we were of the same mind. He met Helen once and was greatly taken by her. Why not? Helen is a real beauty, though now in her forties. She still turns heads. He would occasionally mention her and I could tell she’d had an effect. That got my dick trembling. He was in town for meetings we arranged a drink. We met in a hotel and had a few pints. At closing time I suggested a couple more in my house, He was staying in another hotel nearby.

Helen was away for the night at a friends place. The guy and I had a few more and we talked about a holiday we’d just come back from in New Orleans. He was really interested. I said I had some photos. He wanted to see them. I really took a risk when I went to get them and slipped a couple of Helen topless in our hotel in the French Quarter. And one a little bit more than topless. It really turned me on thinking that he might just look at Helen, not expecting what he got, and be turned on. My heart was beating when I handed him the photos.

He glanced through them and when he reached a shot of Helen provocatively topless I held my breath. The effect was instantaneous. His eyes widened and a smile took over his face. Helen was wearing shorts and her tiny blue top was pushed up revealing her beautiful breasts. ‘She’s gorgeous’ I think he said. His hand even shook a bit. The next photo was even sexier. Her shorts were now pulled down and her right hand was on her pussy, a single finger disappearing inside. I thought he’d come in his trousers right there. (I nearly did too.) He asked me if I had any more. I risked everything. I told him I had but I also said I had a video we shot on holiday in the west of Ireland. We’d rented a cottage in the middle of nowhere and one afternoon after a long lunch we shot a video with Helen striping off gradually and then wanking me off in the front garden of the cottage. The finale has me fucking her over the bonnet of our car.

He begged to see it. I pretended to be reluctant but I couldn’t wait for him to see it and to see what might develop. I put it on. It starts innocently enough with us fooling around, but when the tits started to appear the guy got really fidgety, crossing and uncrossing his legs. My cock suddenly was as hard as a rock too and I deliberately didn’t cross my legs. I was fascinated by the growing bulge in his trousers. He made the occasional comment that clearly suggested he was very turned on watching my wife stripped off and then me pounding in to her. He also mentioned my dick a couple of times, that hinted at something more to come. The atmosphere was steamy and highly sexual to say the least. And when I popped my load all over Helen’s arse, spunk drip, dripping off onto the grass in the garden I thought he would shoot his load too. Nobody had ever seen this video before and it was the most thrilling spectacle to watch another man staring at, and drooling over it.

At the end he gave a foney sigh of relief and said ‘that was really something’. We were both still turned on. Then he asked me if he could borrow the movie, he liked it so much. We both knew what he meant. He was dying to wank over it. I said I didn’t want it to leave my house. He appreciated my point of view but was disappointed. The sexual tension was still tangible however and I took another risk. I told him he could ‘use it’ here if he liked. He knew immediately what I meant and smiled. ‘I’ll watch it again with you. If you like. Or I’ll leave you to it.’ I said. Have to say I was shivering with excitement hoping he would say ‘stay’. He did, after considering for a moment or two. I put the video back on. I didn’t want him to change his mind.

When Helen started to push up her top to reveal her naked breasts I ran my hand across my cock through my trousers. He saw me and it seemed to relax him. He did the same. The room started to spin I was so turned on. When Helen slowly pushed her shorts and knickers down he started to unzip slowly. I did the same. His cock pushed out and he seemed to give out a sigh of relief. It was solid as a rock, about average size but thick and rigid. My heart nearly stopped. I pushed my hand into my trousers and pulled out my dick. We looked at each other with our throbbing cocks in our hands.

He was first to start pulling when Helen’s fingers went into her pussy. I followed him staring at his cock as he stared at the screen. The pumping got harder and faster as the action on the screen got hotter. I was watching myself fucking my wife while wanking off with another guy. I’d never been so excited. He started moaning as he pumped, losing all inhibitions. I murmured yes, yes as my pumping got fiercer. I was watching his dick, hoping to see the spunk flying. He was staring at my cock in Helen’s mouth. He said he was dying to cum. I told him to hold on. I would have loved to feel his cock but was too nervous to try. I would also love to have taken the hot throbbing dick in my mouth but I didn’t dare. Instead I watched him build up as I held myself on the brink of exploding.

He waited till the moment on the screen when my spunk shot over Helen’s ass and he couldn’t wait any more. He moaned and a first jet of spunk shot about 6 inches straight up. This was followed by a constant flow over his hand as he finished himself off. I was close behind, pulsing a splurge of goo over the carpet and then my hand. He stared at the gunk dripping off my cock. I stared at his. I wanted to lick it all up but didn’t dare to try.

fterwards we were both a little embarrassed but not as much as you might think since we were both involved to the same extent.W e had a few more drinks and he went back to his hotel. We’ve met up a couple of times since. But so far neither of us has mentioned it. We will though.

that is soooo sexy. I can imagine every nervous step, both of you not wanting to go too far or fast in case the delicate 'balance' would be upset and the moment lost ... it seems you both got it right ... you planing another video watch and wank? ... please let us know ...if you do, I reckon some mutual wanking and maybe sucking might happen eh .. I look forward to your next post

Thanks funtime. Glad you liked it. Any more and I'll let you know.

There was a guy at school I'd been wanting to jerk off with for a couple of years. We shared a tent on a school camp when we were 14 and we talked about sex all night. He was tall and skinny like me. Eventually he went into the bushes to jerk off by himself. I didn't have the balls to go with him.

A little while later we started wrestling each other a bit in our school uniforms which kind of turned into dry humping. I was so turned on by it.

Another friend of mine who I used to talk about jerking off with all the time caught a glimpse of his cock in the change rooms and said it was big, so I was now even more curious.

Not long after that I stayed the night and his place and we got smashed on Drambuie. We ended the night in our Y fronts rubbing ourselves under the bedsheets while we talked about the chicks we wanted to fuck. I could tell just by looking at his package that he was indeed big.

A year or so later he stayed the night at my place while my parents were away. We got smashed on tequila and started watching Basic Instinct which was quite a new film at the time. We started talking about sex again and eventually I put my hand down my pants and started playing. We talked about fantasies and then I just said I've always fantasised about jerking off with you and that I was embarrassed by it. He said it was cool and then led me to my bedroom. Before I knew it he was taking my jeans off and then undoing his. He put my hand down his pants and he put his hand in mine. And we started jerking. He then pushed me back on my bed and then put my cock in his mouth. God it felt good. After a while he asked me to return the favour which I did. I finished him off by hand, which he came all over. And yes his cock was big!

these are all very hot stories and I thank you all for sharing. I used to walk home with this kid named Mike and he and I would always talk about jerking off. We even had a name for it...The Habit. He had a huge cock and one day as we were talking about it he and I decided to jerk off together which led to me sucking his massive young teen cock. It was so hot.