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Bob43 Novice Jackinchatter

18 posts since 2011-04-26
bisexual male from Windsor, Ontario
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I was almost 13 yrs. old and had a very nice customer on my paper route. I would go back to his apartment when I was finished. It was summer time and I was always thirsty so I'd sit and have an ice tea with him. He also had a great collection of porno mags. After about a week he started talking about how he liked seeing my hard cock poke against my shorts. I was scared yet excited about him noticing. Over the next few days he began rubbing my cock but always stayed outside of my shorts, he encouraged me to slip my shorts off but I was too scared.
Skipping ahead a few more days, I had come in and "John" was in the shower so I sat and looked at the newest porn magazines he had picked up. I had my hand in my shorts was slowly rubbing my cock. I didn't noticed "John" standing behind me until I heard him groan. He was naked and was stroking his hard cock. I watched him shoot a big load of cum on the kitchen table right in front of me. I was so naive that I asked if I could cum like that... I was so excited about what I had just seen that all my nerves vanished.
I felt like i was on remote control. I stood up and took of my shorts and tee shirt and began stroking my cock right in front of him. My legs started shaking and I felt like passing out but I wasn't going to stop until I had cum too. I had felt most of these feelings before but had always stopped, this time I wasn't going to stop no matter what. Then there was this fullness in my cock and with a slight sting a magical rush of relief as I shot my load all over the floor.
Obviously a huge amount of detail has been left out to keep the story short. I hope you enjoyed it though. it is one of my best memories grin
 
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About a month after i turned 18 i bought a set of butt plugs. mmm i still used them today. edenfantasies.com has an excellent selection
 
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A late starter, I was about 15 and in the ninth grade. A classmate bragged about the vibrator he kept under his bed and the Kotex and Tampax ads and Playboys he kept there. He showed them to me but didn't demonstrate. Curious, when my parents were away I got my father's vibrator he used for headaches. It was too big to be good for masturbation but I vibrated away anyway. It felt really good and it wasn't long before the little fellow got really stiff and felt really good. The next thing I knew this creamy and sticky liquid spurted out. That felt really, really good! I felt very guilty and was sure that I would burn in hell. Maybe I will but I'll be masturbating up to that time if I'm able to. I've been masturbating for about 48 years and I see no reason to stop now.
 
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aquist Amateur Jackinchatter

192 posts since 2010-04-09
84 year old bisexual from arkansas
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omg that sounds hot i did it with my older brother he was 9 and i was 6, i heard him wacking in the bathroom and he showed me how to do it plaplaplaplaplaplaplaplaplap been doing it ever since. omg did your dad have a big dick? did he cum? how about mom what was she doing all this time? its hard to imagine but funtoo so taboo but so hot---Allen
 
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hayden365 Novice Jackinchatter

12 posts since 2010-05-18
32 year old curious
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I dont remember my very first time, but i remember going round a mates house and going into his back garden, it was quite long and there was a large wooded shed at the bottom. whenever his mum wasnt there we used to play hide and seek, just the two of us and if we were caught we had to do some form of sexual dare. we were only young but already i was quite larger than him, and one of the dares was to suck him off. i said yes, taking his cock in my mouth, but in response i said to him i didnt want to play hide and seek but truth or dare. i then dared him to do the same and came there and then in his mouth. This continued every time we met, including a sleepover where he dared me to walk naked to the toilet pretending i was sleepwalking, i went out limp until his 17yr old sister appeared and not only did i go hard, she even claimed i was dripping as i ran back to the room!
(pm me if you want more stories, i have a few more)
 
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marriedguy Amateur Jackinchatter

104 posts since 2010-01-12
55 year old curious from SE, uk
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i was 13 at a scout camp, was sharing the tent with some friends and got an erection but was too embarassed to let them see it so i snuck out into the woods. i had already started cumming by rubbing myself on the bed and but did not know how to use my hand to masturbate. i was so horny and needed to cum that i persevered masturbating with my hand til i did ejaculate.... wow! have not looked back since :o)
 
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BigKid666 Amateur Jackinchatter

336 posts since 2011-06-25
44 year old bisexual from USA
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I don't know how I figured it out, but when I was thirteen, I got a latex glove and put some Vaseline in one of the fingers and I put my cock into it and pulled the finger on and off. I guess I was trying to simulate sex. Anyway, it obviously felt good so I kept doing it a few times. Sometimes my dick would bust through the latex and I'd have to move on to a new finger. One night I was doing it and it felt so much better than normal and I had my first orgasm. I don't know if I ejaculated of not because it was dark, but the next night, I did it again in the bathroom and sure enough, white fluid came out. I figured out soon enough that I didn't need the glove. That was a great discovery and one that I couldn't wait to teach my younger brother...
Be true to yourself!
 
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Jack_Creamer Skilled Jackinchatter

524 posts since 2009-10-22
74 year old curious from Oklahoma
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BigKid666 said:
I don't know how I figured it out, but when I was thirteen, I got a latex glove and put some Vaseline in one of the fingers and I put my cock into it and pulled the finger on and off. I guess I was trying to simulate sex. Anyway, it obviously felt good so I kept doing it a few times. Sometimes my dick would bust through the latex and I'd have to move on to a new finger. One night I was doing it and it felt so much better than normal and I had my first orgasm. I don't know if I ejaculated of not because it was dark, but the next night, I did it again in the bathroom and sure enough, white fluid came out. I figured out soon enough that I didn't need the glove. That was a great discovery and one that I couldn't wait to teach my younger brother...


I remember my first love affair with a rubber glove. I was thirteen and had been jacking regularly for a few months, very frequently as a matter of fact. I became fascinated with the texture and feel of a rubber glove. I don't remember what I used for lube. But I found the rubbery feel of that glove irresistible. It felt so good it jack off and cum in that warm, slippery rubber.
Jack_Creamer
 
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tugga Amateur Jackinchatter

207 posts since 2006-02-05
56 year old bisexual from uk
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Not sure how i figured it out but at around 9/10 yo i got in the habit of slipping my pj's off once i thought everyone else in the house was asleep because it felt good. One night i was rubbing my hard on on the ssheet and somehow realised that if i pulled my foreskin up and down over the bellend it felt even better....It started to feel really good and i remember my toes curling up and my whole body feeling really hot and shaking, i felt a few squirsts of liquid coming out my cock (I had no idea what it was at the time) and then just lying there unable to believe how good i felt. when i looked at the liquid id shot it was just a few drops of clear stuff and i thought id broken my dick....didnt put me off though....been wanking like a nutter ever since..
too much is never enough
 
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I was barely 11, and I'd just had my first wet dream the night before. I dreamed I was fucking a girl standing up in the shower, the girl was going wild, and I could vividly feel myself ejaculating into her. The next night, I just had to know how it felt to be that girl. I hid my penis between my legs, rubbed my breasts, pretended I was a girl and a boy was fucking me, and pumped my hips until I ejaculated "backward" beneath my butt. It felt so incredibly good that I did it again every night after that. I'm now 61, and I still love to pretend I'm a woman, although I don't indulge in "girls' style" masturbation every night any more!
 
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Earlybird Amateur Jackinchatter

347 posts since 2011-07-10
heterosexual male
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I was 5 years old when I discovered masturbation and experienced my first orgasm.

I was in my bedroom after taking a bath. I had noticed that my penis would get really hard sometimes, but I didn't know why. This time, I decided to touch it. That felt really good, so I kept doing it. A few more seconds of this felt so good - I could hardly stand it. I stopped, but the feeling got even stronger, and a few seconds later, I had my first orgasm! It was extremely intense. I screamed and almost passed out! My whole body jerked so hard, I nearly fell out of my bed! I had no idea what had just happened to me, but I knew that I wanted to feel it again. I touched my penis some more. The feeling built up again, and I experienced my second orgasm just a few seconds later! Again, it was so intense that I nearly fell out of the bed! But....it felt so, so good! I was worried that I might not be able to get that feeling again. So...I did it again...and again...and again... I gave myself the 'special feeling' 10 times that day! I was very, very happy to discover that it wasn't a one-time deal, and that I could make it happen whenever I wished.
 
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GREYEAGLE Amateur Jackinchatter

121 posts since 2006-02-20
77 year old
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first time for me,i wasn't doing it,but instead it was being done to me,i was about 9 years old i think,i was sitting on the couch and he was kneeled down in front of me,both of us naked,and he took my cock in his hand and started to stroke it,all the time asking me how it felt,when he knew it was feeling real good,he started going faster,then it hit me,i about lifted off the couch!!! never did forget that time,ive masturbated many times to that experience!!!
 
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