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olderteddybear Amateur Jackinchatter

169 posts since 2021-06-16
63 year old heterosexual male from Florida
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I enjoy stories about the first time you masturbated, the first time you had sex, the first time you saw or felt a naked woman... Please post your tale so we all could enjoy!
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When I started masturbating, it was by lying down on the floor of my bedroom propped up on my elbows and grinding my hard cock into the carpet until I ejaculated. This became a problem, however, when I went to college and 1) had a roommate and 2) a tile floor. End result of this? I was unable to masturbate for the first few weeks of my freshman year and I was GOING CRAZY!!! Here's how the dam finally broke...

I was at breakfast in the dorm cafeteria with a long-haired blonded classmate named Lynn. She was gorgeous with an incredible ass. I was so fucking hard I couldn't take it anymore, so I excused myself to go to the bathroom. I locked myself in a stall and proceeded to stroke myself by hand for the first time ever. It took me about twenty minutes but, yes, I finally exploded. All over the place. There was cum everywhere.

Needless to say I was late for class.

P.S. I've been stroking by hand ever since. I'm a southpaw BTW.

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olderteddybear Amateur Jackinchatter

169 posts since 2021-06-16
63 year old heterosexual male from Florida
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Awesome story... thanks!
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WankerP Novice Jackinchatter

47 posts since 2021-03-04
66 year old bisexual male from UK
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My first time masturbating was pretty much a standard soap off in the bath in response to a stiff penis. After that I was a compulsive wanker to the extent that when I first fucked a vagina I more or less had to wank myself off into her slit. Got better at it soon enough, but a wank was always best.
Addicted from day 1
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magzine2 Professional Jackinchatter

2162 posts since 2016-11-02
73 year old heterosexual male from N.Ireland
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my uncle gave me my first wank.I still get hard thinking about it.
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magzine2 Professional Jackinchatter

2162 posts since 2016-11-02
73 year old heterosexual male from N.Ireland
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my uncle gave me my first wank.I still get hard thinking about it.
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BlueBallGuy Novice Jackinchatter

25 posts since 2021-10-20
51 year old curious male
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I don't recall for sure how old I was but I recall my first time was after a close friend my age showed me how to do it. I guess we were probably 11 or 12 and I was visiting his house for a sleepover. His mother had given him a book to read for boys in puberty that explained things like wet dreams, ejaculation, etc.
We were in bed at night comparing our hard-ons. I'm circumcised but he was not. He said he wanted to jack off. Then he spit on his hand and stroked off pretty fast. I remember him groaning "here it comes, here it comes" and then he tensed up and shot a big load of semen on his belly. I remember watching him spurt with fascination.
I was too nervous to do it myself in front of him. Instead, I tried when I went home by myself after I went to bed. It was great, but I didn't produce any cum the first time. The second time, I blew a pretty big load. After I got comfortable with it, we masturbated together a few times. When we got into our late teens, we also "shared" a girl one time. She was a hot, horny young lady and she loved it. It was awesome.

Losing my "virginity" wasn't a straightforward thing. (It rarely is, right?) Two girls gave me hand jobs before I ever put my penis in a vagina. I did that when I was 16 with a girl the same age who had way, way more experience. I was sort of the "flavor of the month" for this girl because she floated between different guys and she'd dump you as soon as she was satisfied that she'd gotten you in the palm of her hand.
We were making out at a friend's house in the bed with no adults around the house and she was grabbing and rubbing my cock. I told her I wanted to have sex, and at first she refused. She made me beg, which looking back now I think she enjoyed. Finally she laughed and peeled off her pants. She was blonde and I distinctly remember her muff of blondish-brown pubic hair and the amazing smell of her pussy. It was awkward though. I unsuccessfully tried to put one condom on - didn't work - so I had to try again.
Finally I got the rubber on and slid it in her. Her pussy wasn't as tight as you might expect for a 16-year-old but it had an amazing creaminess and warmth. She squeezed her pelvic muscles around my shaft and wrapped her naked legs around me and I didn't last long. LOL. I pumped about a dozen times before hitting the PONR and plunged deep and shot my wad.
She never let me have sex with her again though she did give me a hand job a few months later.

What I am really interested in is tales of having sex with someone else whose first time it was.
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star69 Skilled Jackinchatter

566 posts since 2021-09-24
33 year old
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First wank was about 1994
Sexy girls in the sun newspaper and others
Topless and lingerie drove me crazy seeing them dressed for sex

First sex was with a girl at school
She was kinda chunky but was a decent fuck
She let me cum in her a few times
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troutdog Amateur Jackinchatter

323 posts since 2012-08-22
64 year old curious male from Washington state
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I was very young. I got in trouble so My parents made Me go to bed early. It was summer so everyone else was outside. I went to the bathroom to take a pee and found a pair of My older sisters panties in the hamper. I had to take a sniff. I didn't understand why, but it made Me incredibly horny. I took the pair of panties to My room with Me. It was freaking driving Me crazy. I laid there with Her musky panties draped over My nose, as I slowly breathed through the musky crotch. I was in an erotic high My entire body was alive with lust. Eventually I reached under the covers and pulled My underwear down. Now I was naked under the blanket. It felt so nasty that My Cock was harder than ever and My head was spinning. The feel of the soft fabric of the blanket touching My stiff sensitive little dick was driving Me crazy. Then it happened. The soft cotton blanket had a silky satin trim all around the edge. I slowly slid the slippery satin fabric across My stiff over excited Cock. It was like nothing I had ever experienced in My young live. It felt so incredibly good there was no way I could stop. So here I was with My older sisters musky panties draped over My face, sniffing the wonderful scent of Her Pussy, as I slowly slid the satin fabric over the head of My swollen Cock. My head was spinning as My entire body trembled. Well the scent of Her panties mixed with the pleasure of the satin sliding over the head of My Cock eventually became too much. Suddenly My entire body and mind was flooded with intense pleasure and I came Hard. Shooting jet after jet of Hot Sperm up across My belly. It was so incredible I was left trembling. I was in a post Orgasm high and fell a sleep. After an hour or so I heard someone coming up the stairs. I quickly pulled the musky panties off of My face and hid them under My pillow. My naked body was still covered by the blanket. It was my Mom, saying I could come out side now. I often wondered if She could smell the scent of My Sperm. What if I hadn't woke up, and She would have found My sisters panties on My face. That was the beginning of Me sniffing My sisters panties and jerking off every day.
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olderteddybear Amateur Jackinchatter

169 posts since 2021-06-16
63 year old heterosexual male from Florida
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Wow those are great stories! I look forward to hearing more and sharing!
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So, I was actually jerked off *before* I ever masturbated, but sharing that story can be tricky due to various site rules and regulations.

Same goes for the story of losing my virginity.

However, in between both of those events, was the first time I ever masturbated and since *I* am the only person involved in that story, I think it's safe to share.

It's really not that interesting, sadly.
Fairly basic stuff.

My grandfather had recently been moved from his house into a home.

My mother and I were staying at his house while clearing it out. She was in the guest bedroom and I was in my grandfathers old bedroom.

One night, I don't know why, young curiosity I guess, I went looking through his wardrobe.

In the back, buried under a pile of clothes, was a plastic bag absolutely BURSTING at the seams with porno mags. Nothing hardcore, but all the UK standard stuff from around that time (early 90s). Mayfair, Penthouse, Razzle, Fiesta, Men Only, Club, Readers Wives, etc.

Instant erection.
The kind that could smash bricks.

I take the bag onto the bed with me, lay down, start flipping through mag after mag after mag, all while touching myself, rubbing my throbbing cock from base to tip. No clue what I'm doing or why I'm doing it, but compelled to keep going somehow.

I can feel something building and intensifying, internally, but I've never wanked before (and didn't even know, in that moment, that was what I was doing), so I don't recognise the feeling. In fact, I'm not even sure it's a good feeling. It almost feels kinda like a stomach ache of some kind...but I can't stop. I feel this NEED to keep going.

I keep flipping through the mags, looking at the tan-lined tits and the big hairy bushes. I know it's naughty. I know I'm not supposed to be seeing this kind of thing. That adds to the thrill I'm feeling.

I specifially remember I was looking at a readers wives page when it happened. She was a trashy looking dirty blonde with blue eyeshadow and matching lingerie. I would do ANYTHING to be able to track down that specific magazine and photoset today, but that's a different story.

Anyway, I'm looking at this trashy slut with her bleached blonde hair, dark roots, blue eyeshadow and big dark bush, still slowly stroking my aching cock when suddenly there is an ERUPTION. Out of nowhere, the pressure I had been feeling building inside me suddenly broke free and thick, heavy, warm spurts of white sticky liquid started pumping and oozing out of the tip of my cock, down over my hand and onto my stomach and balls.

I was shocked. Didn't have a clue what had happened. Thought maybe I'd broken something.

I don't remember exactly what I did next. It's all a blur. I must have cleaned myself somehow. I know I put the porn back where I found it. Then I went to sleep.

The following night, I was ready for Round 2. I couldn't wait to pull the porn out again and repeat what had happened the previous night...but the bag was gone.

My mum must have found it during that days clearing and gotten rid of it.

So yeah, that was the first time I made myself orgasm.
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First time sex was really memorable. With lot of wanking experience, the pleasure of shooting load was already known.
When it was time for watching pussy expecting to take cock inside, it was really amazing. The cock was throbbing and leaking precum. Initial efforts of entering virgin pussy were not that pleasant. But once it entered inside, felt so warm, wet and words are short to describe the pleasure of thrustng deep inside and shooting the load.
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Lovecock Amateur Jackinchatter

387 posts since 2023-03-13
47 year old homosexual male from Philadelphia PA
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My first time memories are similar,. We had an off house garage in my childhood home. That was my dads space. He had a not so hidden collection of many various magazines from soft core Playboy to Penthouse to hardcore XXX magazines as well. I found those at a young age before I could even ejaculate semen. I was dry orgasming to a great supply of dads porn before I even knew about the birds and bees.
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My first blowjob:

When I was 13. On a sleepover with a childhood friend. We had discovered each other cocks when we were prepubescent and had been getting naked and playing with each other for several years.

One night, we were laying side by side stroking our hard cocks talking about girls that we knew in school, and by this time we were both old enough to ejaculate cum.
All of a sudden he sat up and leaned over my cock. I could feel his hot breath. I closed my eyes as I felt his warm, wet, inviting mouth engulf my cock. It was the most fantastic sensation I had ever experienced. I came in less than a minute and he swallowed every drop. It was incredible.

He lay back down as says "now you do that to me" so I rolled over and started sucking him. He lasted much longer and I had to stroke him with my hand as I sucked to get him to cum. He started bucking and humping then I felt the surges of warm cum in my mouth, but I gagged and pulled off quickly. I hated the taste. He grunted "don't stop, stupid" so I grabbed his cock, still shooting cum, and finished him off by hand.

We continued our blow job relationships until we were 20 and we both moved away. I never did get used to the smell and taste of cum but I would wait until he was done cumming, then spit it out and let it run down his, by then, very big cock and balls.

Now, I am married.... and don't get blowjobs. Ever. I dearly miss getting nice, hot, wet sloppy blowjobs. And can't find a bud to trade BJ's or HJ's with.
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olderteddybear Amateur Jackinchatter

169 posts since 2021-06-16
63 year old heterosexual male from Florida
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Great stories everyone!
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