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jason74 Amateur Jackinchatter

315 posts since 2019-03-12
49 year old heterosexual male
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My girlfriend sucking my cock with her finger up my arse!!..Best feeling I have felt in my life.lovelove
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Thickcock Novice Jackinchatter

77 posts since 2015-08-04
43 year old bisexual male
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Fucking my sex addicted ex. She loved sex and knew how to give me mind blowing orgasms.
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WhitehawkWanderer Amateur Jackinchatter

294 posts since 2016-12-22
61 year old curious male from Idaho
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I had many mind-blowing orgasms while having an affair with a married woman a few years ago. She was (still is?) sexually aggressive, very creative, and extremely open minded. Her skills were amazing, and there were more than a couple of times where the orgasm was like an out-of-body experience, coupled with her. One of the best was the first orgasm with her. We were having lunch in the back seat of my car parked in a public park, and it was pouring rain. Through our conversation she flat out said she wanted me to fuck her as much as she likes, and she wanted it right there, right now. As she started unbuckling my belt to push down my pants, I asked to suck me just a bit (I figured if she was so bold, I could be bold in return). She went down on me and gave me the best blow job I had ever experienced up to that point. She kept at it, with obvious well practiced skill, bringing my sensations higher and higher. I help back as long as I could, letting it build inside me. Finally, I could not hold back any longer, and I announced, "I'm going to cum!". I expected her to pull back, since I had been with several girls who didn't let me cum in their mouths, but instead she just sucked me harder and harder, until I exploded in her mouth. It was beautiful. I could feel her swallowing down ever bit of cum as I pumped her mouth full with pulse after pulse of hot semen. I was floating with ecstasy of the moment, blown away by the intensity of the orgasm. She grinned as she came up, and giggled slightly. We kissed deeply, and I loved how I could still taste the residual cum in her mouth. I learned that she loved to suck cock and swallow cum almost as much as I enjoyed letting her do it to me. We experienced many more orgasms together over the course of our secret affair. God I miss her!
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Garcia007 Skilled Jackinchatter

869 posts since 2011-03-15
35 year old male
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In the mouth of a broad while her friend was massaging my prostate.
I live to edge & goon
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SmokeChron Amateur Jackinchatter

300 posts since 2014-01-21
33 year old heterosexual
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At work several years ago, I come in after having a long weekend off and I'm told that I'll be in charge of training the new girl (at that point I didn't know we'd hired anyone). So I'm introduced to this insanely hot 20 year old fit blonde with a huge rack. I can't stress that enough because all I could do all day was stare at her tits, thankfully she didn't seem to mind. That workplace was not super formal, but at least people usually wore collared shirts and slacks. Bless this girl because on her first day at a new job she decided to wear a loose orange tank top and a little white tennis skirt. So I spend all day with this girl, teaching her software and inventory systems and such, but all I can think about is how does a girl with such a fit athletic body have such gigantic knockers.

Anyway at the end of the day my girlfriend at the time came to pick me up from work, and she comes in and I introduce her to the new girl. The whole car ride home, I can't help but talk about the new girl, and my girlfriend is receptive, asking me all about her. When we get home, she brings me straight to bed and tells me to fuck her like she was the new girl. I had so much sexual frustration and lust built up from the day, that I practically broke the bed pounding my girl into it while she egged me on saying things like "she really filled that tanktop with her amazing breasts," "don't you wish you could suck on them? they'd bounce around so much while you were fucking her," and "I bet her cunt is really tight, you'd probably cum a lot."

That was my best cum, and my girlfriend loved it too. I never got to fuck the blonde girl though, and later found out her amazing breasts were a product of her being newly pregnant, before her belly started to grow.
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enis Skilled Jackinchatter

823 posts since 2006-02-10
80 year old curious from Midwest US
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My most memorable ones result from long slow JO sessions using lots of lube and many different techniques over several hours. Near the end one of my legs starts to shake and twitch from the toes up and that tingling overtakes my whole body and then I let it release. It's mind blowing.

Second would be some of the orgasms resulting from my wife's long, slow,gentle stroking. I just lie back and let her play. She also uses many techniques and grips and varies the strokes. I never know what's coming next but I do know what's cumming.strokestrokestroke
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Bimike1962 Amateur Jackinchatter

280 posts since 2017-06-27
62 year old curious male from Eastern Washington
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The most intense orgasm i ever had was the result of two women sucking my cock, and massaging my balls. When i started to cum they slowly pulled anal beads from my ass....i thought i was going to die...
I want to cum with you!
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Mine was when one of my ex-gfs decide to get me a blowjob. I was sitting on the sofa in the lounge, right in front of a large window with no curtains where people walked past not 4' from the outside. She knelt in front of me and pulled out my cock. She insisted on me keeping my hands to myself, then proceed to give me the perfect blowjob. Looking into my eyes until I eventually blew in her mouth. She showed me the contents then swallowed it down and left me with my cock hanging out. It was awesome.
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Best orgasm ever would have been with my mistress. First time cumming in her without a condom was mind-blowing. After she got pregnant, the sex and orgasms were amazing. Sex with her made sex with my wife even better.
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ShortFuse Professional Jackinchatter

1248 posts since 2019-11-03
52 year old bisexual male from Nashville, TN
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My best orgasm was when I was 15yo. I was watching a girls basketball game and the sight of their titties jiggling as they ran had my cock hard and leaking. I moved behind a table and took it out, masturbating in a gym full of people. I got close and decided to blow my load in the bathroom. I went to the last stall and unloaded. I have never cum that much in my life...ever. I honestly thought I may never stop cumming. It was everywhere. Dripping off the toilet, down the walls, on the floor, on my clothes....I have never seen so much cum.

I have never produced that much semen. It was amazing.
Small dick chronic masturbator
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about 4 years ago, jerking and chatting with an older British guy on skype. He shot his load them licked it up. I continued masturbating and I moved on to a medium plug in my ass. He had some amazing dirty talk, directing and complimenting me. After some ass to mouth and precum eating I felt my prostate get that intense pulse and i made several fat ropes of cum shot over the floor. Should have eaten my load but I was too spent.
I wish I had asked him to take screen grab me. The photos would be great to have and share
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al60 Skilled Jackinchatter

622 posts since 2014-05-27
67 year old heterosexual male from uk
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For me, 2 major orgasm experiences.

First experience was early on when I first experienced ejaculation. Remember I would climb a metal carport support pole at the vacant house next door to mine. Wearing shorts, I'd rub my cock against the pole as I climbed. It would make me dry orgasm, and I'd hang there shuddering, moaning, and pressing my cock into the pole. Then, the fateful day when my dry orgasm turned into a huge load of hot cum exploding in my shorts and running down my balls and legs. AMAZING feeling! Remember it so fondly.

Second experience was much more recent, about 2 years ago. Finally talked my wife into using a strap-on to fuck me. First time was exciting, but had to take it slow as it hurt a bit. I vividly remember telling my wife to go slowly because it hurt. As she was pushing it against my clenched hole, I suddenly relaxed and the head forced its way in, making me gasp. The pleasure as the entire dildo slid into me was fucking great!! Don't remember how many thrusts it took, but was only a few. My hard cock was swaying as she thrust, and I let out a loud moan as my cock started spewing cum. Hands free, never even touched it! Felt amazing!
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staples2287 Skilled Jackinchatter

640 posts since 2011-04-25
49 year old heterosexual from US
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Cumming inside my first girlfriend's vagina when I lost my virginity.
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