Stories Of Jacking Off

Stories Of Jacking Off

Home Masturbation Male Solo First Time Jacking-Off

Posted by: oldfan
Age: 18 Then, 68 Now Posted on: 05 Feb 2021
22 comments
13 likes
63 views
Category: Masturbation Male Solo
Tags: masturbation , solo , first time , orgasm , jack-off

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Thanks NiceCockForYou. Sure wish I would have had a friend like you to have helped me get over my shyness and to explore my sexuality.

MMMM very nice, a late bloomer in College was a nice friend, he was very shy, I gave him his first touch of another cock and his first blowjob!! Interesting thing is he had a fetish of wanting my big toe in his ass as he masturbated!! He has a beautiful slim cock, about 3 1/2 inches long when hard , wonderful to suck and he likes sticking it in my ass and cumming that way, a good friend for College years

This story reads almost exactly like the one I wrote. Except mine was in the 80s. Late bloomer also. Mine is just “first time”read it and see what you think

Love a good first time. It's endearing that you were such a late bloomer.

A wonderful story, Oldfan. I still remember Farrah F. and can easily see how looking at her [and Sandy] would give you an erection! Am so glad that you quickly got past the initial guilt feeling and, yes, nothing that feels as good as masturbation could possibly be at odds with either the laws of God or of Nature.

Too bad you missed out on at least five good years of masturbating before you figured it out.

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As a pre-teen child I had done a little "I'll show you mine if you show me yours" play with the girl next door who was my age. But other than show/look, it never went any farther - no touching each other. And my male friends and I never broached the subject of jacking-off. Though I had heard the term it was only in the form of an insult hurled at those we didn't like - "he's a real jack-off!"  I had no conception that boys may do anything sexual with other boys or that a boy could do anything like masturbate.
In addition, I was raised Catholic and to the Catholics preached any form of sexual activity other than that of a husband and wife to procreate was a sin. This was drummed into us and was deep in my psyche.
Throughout junior and senior high school I was very much an introvert with little self-confidence so didn't date or go to dances. In 12th grade I finally had my first girlfriend but she was as sexually naive as me so our relationship consisted of holding hands and kissing. Then after graduation I went to one college and she to one in another state. And other than wet dreams, I had no experience with sexual release.
How my life of joyful masturbation began:
So here I was an 18-year-old college freshman, a virgin who didn't even know how to jack off! College was a new world for me: guys talked about sex, guys had sex in their dorm rooms (even though we had gender segregated dorms) and I learned that "jack-off" meant more than a derogatory term to hurl at other guys.  I guess I learned the “jack-off motion” (the somewhat open fist moving up and down) from the other guys on my dorm floor.
Like most guys my roommate and I put our favorite posters on our dorm room walls. This being 1970, one of them was the famous Farrah Fawcett bathing suit poster with her nipples pushing against the top of her suit. Another was titled "Glamorous Sandy" and was beautiful blond, topless standing on a beach with her beautiful tits staring out at you. I would look at these and could feel my cock grow but didn’t do anything with it, or really know to do anything with it. Until one evening when I had just taken a shower in the communal shower room and walked back to my dorm room with just a towel around my waist. My roommate was gone - I think he went home for the weekend.  Looking at Farrah and Sandy started to cause another erection and since I was still drying myself after the shower, I was rubbing my cock with the towel. It felt really good, me rubbing my cock and these two beauties smiling at me from the posters. I sat down on my desk, opened the towel, wrapped my right hand around my shaft and started rubbing rubbed my dick, using the jack-off motion I had seen. I jacked faster while I stared at Sandy's beautiful tits. My cock felt warm, so I kept it up, going faster. All of a sudden I started to feel a funny tingle in my groin (I didn't know it was the beginning of an orgasm). This kind of scared me so I stopped. But not for long. My hard cock still felt great, the tingling did too, so I rubbed some more. Faster. Harder. Then the tingle came back this time stronger, starting in my groin and bursting out to my stomach, chest, my entire body! It felt fantastic! Now I got the full-on, ultimate tingle and WHAM, my first self-induced orgasm and eruption. Spurt after spurt of cum sprouted from my dick.
It felt so good. But with the Catholic upbringing and the sexual morals taught to me at home, I thought I had done something really bad – certainly this is a sin!!
That’s when I came to the realization that nothing that felt this fantastic should be a sin. And even if it was I didn’t care! So I did it two more times that evening. By this time my cock was raw and I had to stop.
So this was the first of many thousands of enjoyable orgasms that jacking-off has provided me over the past fifty years. And yes, my wet dreams did go away – they were no longer necessary!
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by

master

on
October 19, 2015

Current Age: 40 Age when it happend: 20 Where it happened: outside Langauge: English Sex: Male Rating: 7
Category: Gay

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Copyright 2019. My First Time. Site by Paradigmnext
Cutting grass for this older man down the street, for some reason I got very horney and went behind his shed to jack off. Right when it got good I herd him say. So that’s what your doing. he came around the corner and caught me. as I was trying to zip up and hide it. he said don’t stop now….. then he said no wait. come over here. we went into his garage where he had 2 chairs, we sat down then he said Ok now finish….. I was humiliated, as I hesitated. then he said here I’ll do it with you. he stood up pulling his plants all the way down, exposing his semi hard cock. I was surprised at it’s size. So I did same. we were sitting there playing with our cocks… mine really wouldn’t get hard again But God I wanted to cum….. he said having a little trouble are we? I said nothing…. then he said. here. and grabbed my dick and started playing with it…. he said this is how I like it. rubbing the top part of my dick, that was getting VERY HARD NOW….. he pulled on it for a while. then he reached over with his free hand and took my hand and put it on his cock. I started jacking him off….. Not knowing what I was doing he was giving me instructions. then he said Oh just forget it. and pushed my hand away…… He reached over and grabbed my balls giving them Quite a hard squeeze, I yelped a little as he laughed. then he said on your knees! I did as told. and in his cock went…… he told me to look up! he said Always look up when giving head, boy! he got frustrated with me and grabbed both sides of my head and started face fucking me…. It was hard to take all his cock and it was big around! I was struggling not to choke. He noticed me jacking off my cock and told me to stop it! then he said you don’t want another ball bruiser do you? With cock in mouth I said unnn noooo, he said don’t talk with your mouth full. Damn! shortly after this he pulled out his cock and started jacking it off right in front of my face. then he hollered open your mouth. OPEN OPEN OPEN!!!!! I did just in time to get a mouth full…….. after he stopped cumming he then took his cock and played with the cum on the side of my face and was moving it into my mouth. after he got all of it he could. he said ok now back to work………

Index » Masturbation » For Him » Best jack off story?
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.

Check out my porn blog at https://slostroker.bdsmlr.com/ and my writing blog at https://slostroker.wordpress.com or catch me on Skype as SloStroker
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.
old long time jacker who loves anal with woman only
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
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