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whisperinghot Amateur Jackinchatter

174 posts since 2008-01-12
67 year old bisexual from California
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hmmmm....

I'd have to say when I was about 17 and an older man masturbated me (for the first time). His wife had gone to bed, and we stayed up talking about sex, getting hotter and hotter. He asked if I wanted to masturbate with him, and we both took off our pants and sat facing each other, still talking about sex.

He came over and took my cock and began masturbating me as I'd never felt before. It was so awesome! I wanted to cum real bad, but he held me back until I was horny out of my mind. Somewhere along the way, he slipped his finger up my ass, and I came clenching hard onto it with each squirt.
"...anyone who masturbates is a friend of mine."
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quik2cum Novice Jackinchatter

45 posts since 2009-05-20
72 year old heterosexual from Southern Indiana
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The best orgasm I ever had was at the hands, and breasts of a woman that I worked with. She was 14 years younger than me and was a very beautiful girl. How I ever got into this situation I'm still at a loss to describe. Suffice it to say that we became excited with each others special sexual "fantasies" and we would, on occasion, act them out. One of mine was for a woman to take total control over me, do what she wanted, then leave as if nothing had happened. She picked this one to enact.

One Saturday morning, I had to work, the plant was mostly empty. To my surprise, she showed up asking me if I could help her get some boxes out of her office. I knew it was just a ploy to get me to her office where we could be alone, so I went willingly.

When we arrived at her office, she immediately removed her sweat suit and there she stood, completely nude. I had seen parts of her body before, but never had she been totally naked. I immediately started to get erect.

She backed me up against her desk and sat in front of me in her chair. In seconds, my pants were to my knees, my cock was in her mouth and I was getting harder by the second. She sucked me for several minutes, then she wrapped her big breasts around my throbbing cock and told me to fuck them. I did as I was told, looking down at my cock head peaking out between her breasts with every thrust. In just a few moments, I felt the orgasm starting to build, I thrust even harder. She also knew the time was getting close and she told me to cum on her chest. I didn't disappoint her. With just a few more thrusts, I started to explode. I watched as my cum shot up around her neck and ran down her breasts. It ran around her body and was sliding down her sides. I came so hard that my knees actually got weak for a moment. By the time I regained my composer, she had cleaned herself, gotten dressed and was leaving. As she reached for the door, she told me she would be waiting on me to satisfy a fantasy of hers. And then she was gone. That's the best one I ever had.
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Earlybird Amateur Jackinchatter

347 posts since 2011-07-10
heterosexual male
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My first two orgasms were by far the most intense & long-lasting of any I have experienced. I was 5 at the time. I screamed and almost passed out! My whole body jerked so hard, I nearly fell out of my bed! In general, the dry orgasms I experienced before puberty were more intense & longer-lasting than the ejaculatory ones I experienced after reaching puberty. Plus, I usually experienced 3 or 4 intense orgasms in rapid succession - each successive orgasm stronger than the preceding one. I also found that I could just keep going & repeat the entire experience a number of times. smile Sadly, I lost that ability shortly after my first ejaculation. frown

Ahhh...the good old days....

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Oh yes. An older friend and co-worker to my great surprise was getting a divorce because her husband couldn't keep his pants on around some younger women. I visited with these folks and thought they were the most happily married couple I'd ever seen. After she tossed him out of the house I still visited her and one evening I couldn't stand it and assaulted her, gently of course. She asked me to stop but not before I squeezed some lovely breasts and ran my fingers through an absolutely glorious growth of red pubic hair. Needless to say I had a good j/o at home that night. It got much better a few weeks later when this lovely lady (literally one of the nicest people I've ever known) decided to give me a blow job. After getting her into the 69 position atop me she proceeded to give me the best orgasm I've ever had. Sadly we went our separate ways and she married a more respectable man than I've ever been. This was more than 28 years ago and I still get hard thinking about it and often have to get relief from Molly Palm.
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Rabbit420 Skilled Jackinchatter

579 posts since 2011-04-23
68 year old curious from Minnesota,USA
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I have to say that my very first orgasm was by far the most memorable and best. I'd been masturbating for sometime and never had the nerve to "finish myself off". Of course I didn't know about orgasms and always stopped short for fear that I was hurting myself or doing some type of harm to myself because of the strange, intense and alien feelings that I would experience when stroking my prepubescent penis for long periods of time. My penis would become hard, start to tingle and almost feel numb. My breathing would become rapid and labored. My heart would beat faster, I would start to shudder and I would become lightheaded. Not knowing what detrimental affect this was having on me I would always stop short. Finally one day I worked up the nerve to keep going after I had reached this point. These strange feelings once again overcame my body, my heart began pounding, my breathing was in short gasps, my little hard on started tingling almost unbearably and my strokes became more rapid. I thought for sure that I was going to die, but I had reached the point of no return and continued on. My body started to shudder and "tingle" all over, my penis was "tingling" intensely and almost burning. Finally the involuntary muscle spasms overtook my body and I started to flop around like a fish out of water. I became so light headed that I let go of my penis and must have blacked out. Upon regaining my composure I thought surely I was dead or at least had done some serious damage to myself, but I had the biggest smile on my face and decided that I would have to try this again and I have been "trying it again" ever since.
Curious looking for the right cock to suck
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palmer Skilled Jackinchatter

848 posts since 2007-06-30
70 year old curious from california
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yes, quite often, at least for me, those first times were some of the most amazing O's. First 'bate, 1st oral... It is interesting how/why some orgasms are just so much more intense than others. and of course we want them all to be the most intense toe-curlers we can have but doesnt work that way.
its just sex
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Rabbit420 Skilled Jackinchatter

579 posts since 2011-04-23
68 year old curious from Minnesota,USA
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Yes my first blowjob and first intercourse with a girl were both very memorable orgasms, also my first orgasm when I actually shot a load was memorable too, but none as intense and memorable as my very first.
Curious looking for the right cock to suck
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lupis49 Amateur Jackinchatter

277 posts since 2011-07-05
54 year old heterosexual male from Northern Wisconsin, USA
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First one jacking was very memorable, and also first one during sex inside a girl was aweseome too. But the one i remember the most was the first one inside my wife with no birth control knowing i got her pregnant ( which happened on the first try ) - was phenomenal. Knowing my cum was planting a seed inside her was the best.
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palmer Skilled Jackinchatter

848 posts since 2007-06-30
70 year old curious from california
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i kinda rate them as toe curlers (amazing) & well nothing to write home about (nothing special).
its just sex
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