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Come on guys, describe the best orgasm you've ever had and what lead to it - doesn't have to be from jacking off, nor does it have to be the biggest cumshot ever - simply the best orgasm.


I'll start:

Basically at the time I was in a long term relationship and we were going through a rough patch, she had this cute friend with pretty massive tits who was really close to her at the time, but turns out she really fancied me. We'd kinda messed about in the past, but nothing serious (texting pics, chatting about sex, etc).

I still remember it like it was yesterday. We (me and my gf) had been to a halloween party at her friends place and went home moderately early (gf wasn't feeling great), but later on, about 2am, her friend text me and asked me to come rescue her as there was one guest left who was trying to put the moves on her and she didn't want him to. Naturally I obliged as I was still up playing on my Xbox. I went round and took him home, but for some reasonshe came in the car with me. I'll point out now that she was dressed as a slutty witch in fishnets and a pretty short witchy dress.

After I'd dropped him off we were on our way back to her house to drop her back off she basically spread her legs to reveal her absolutely soaking bare pussy... she said she wanted to fuck REALLY bad and that we should pull into the nearest car park.

No kidding, we parked in a pretty secluded car park at the bottom of a pretty steep hill near some woods and we fucked on the bonnet of my car, on the back seat, on the grass, all under the moonlight. When I came it was one of the most powerful and fulfilling orgasms I've ever had. I think I shot 5 large, thich ropes of cum on her tits as she knelt in front of me, followed by another 3 or 4 in her mouth.

Needless to say I had to hastily wash my car in the morning as there were 'body' prints on the bonnet ...

I know that's a long "Dear Penthouse" type story, but its 100% true, I promise. It was also the start of a 4-year affair and some of the best sex I've ever had... plenty more stories (and some pics) of her in the locker for a rainy day haha.


Now you guys go ... please be honest too. Will make for some enjoyable reading wink
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plush Omnipitant Jackinchatter

5160 posts since 2010-02-06
heterosexual male from USA
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Don't recall a bad fuck most were good and some exceptional and the best were when my third wife would ask me if I wanted to fuck her in the ass. It always got me extremely horny and hard
old long time jacker who loves anal with woman only
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User13 Amateur Jackinchatter

201 posts since 2011-09-18
44 year old
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My ex-gf was a high school teacher. One day she wore yoga-type pants to work and I remember watching her ass as she walked up the street thinking about how all the guys in her classes would be staring at her ass all day.

I actually thought about it the entire time while she was at work. By the time she got home, I was so horny for her that I just bent her over and fucked her right away. She was moaning louder than she ever had before, /9 I have a feeling that she felt those stares all day long, also.

I shot inside of her and my entire body shivered. Still my best orgasm of all time.
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kungfu40 Amateur Jackinchatter

411 posts since 2007-10-27
bisexual from Canada
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I've had many mind-bending orgasms, most were because of new sensations of doing something new for the first time.

One that comes to mind right now was when I was camping with a large group of people. I'd been out with them for a few days, and hadn't jerked off in over a week, and there was very little privacy.

So one afternoon, I told them I was going to grab a nap in my tent.

Of course, what I really grabbed was my cock! I'd been staring at the girls and women in skimpy summer clothes for too long, so even though I was only maybe 10 feet away from the loudly chattering group, I just had to let off a load of cum.

I usually use lube, but didn't have any, so started stroking lightly with my dry hand. I wanted to groan out loud at how good it felt, but couldn't!

I was so horny, and it was so exciting to be doing this so close to everyone! It didn't take me long - I grabbed a sock to catch my cum, and when I came, it was damned hard to keep quiet!

It felt like I blew a pint of cum into that sock! It was almost like I was pissing it out in extra long ropes.

Afterwards I was so drained that I did have to have a nap. Besides, if I'd tried to go back out there, I think my legs would have been too wobbly!
Whatever gets your rocks off!
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kungfu40 said:
I've had many mind-bending orgasms, most were because of new sensations of doing something new for the first time.

One that comes to mind right now was when I was camping with a large group of people. I'd been out with them for a few days, and hadn't jerked off in over a week, and there was very little privacy.

So one afternoon, I told them I was going to grab a nap in my tent.

Of course, what I really grabbed was my cock! I'd been staring at the girls and women in skimpy summer clothes for too long, so even though I was only maybe 10 feet away from the loudly chattering group, I just had to let off a load of cum.

I usually use lube, but didn't have any, so started stroking lightly with my dry hand. I wanted to groan out loud at how good it felt, but couldn't!

I was so horny, and it was so exciting to be doing this so close to everyone! It didn't take me long - I grabbed a sock to catch my cum, and when I came, it was damned hard to keep quiet!

It felt like I blew a pint of cum into that sock! It was almost like I was pissing it out in extra long ropes.

Afterwards I was so drained that I did have to have a nap. Besides, if I'd tried to go back out there, I think my legs would have been too wobbly!


Quality story stroke
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kegspoon Novice Jackinchatter

35 posts since 2011-04-06
74 year old bisexual male from Central NC
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The best one I ever had was the first one, because it felt sooooo good I have been cumming every day since. Most of them are extrordinary
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Actually, the worst one I've ever had was pretty damn good...
Just sayin'!
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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 bare back morning sex. Humped her real slow at the end till I couldn't hold it any more went balls deep in her and came for what felt like forever.
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northwestexplorer Amateur Jackinchatter

187 posts since 2010-10-16
43 year old curious from manchester
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Honeymoon with my missus..... We'd been together for a few years by then, but still loved to fuck a lot....

We'd already fucked that day in the outdoor shower.

Her on her knees in front of me, sucking like a trooper, then she slipped a finger in my ass.... nearly passed out!
married mutual masterbation
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Girl I was dating at the time, and we used to fuck like rabbits when we were together.

One time I was straddling her chest and she was stroking me, and was taking it to a new level.

She'd go hard and fast, then suddenly slow it waaaayy down almost to the point of stopping, then speed it back up.
She had TOTAL control of my dick and was loving it.

Then to make it so much hotter, she was dirty talking the hell out of it. She was saying things along the lines of "Don't you want to cum? Watch it run?" etc. And as she's jerking me, she's literally pulling me closer and closer to her face.

Just as I'm about to totally fucking loose it, I tell her 'Fuck, fuck, I'm so close. Baby I'm going to cum!" and I swear to God, she gets this nasty, deep primal voice and practically yells, "Yeah? You going cum for me? Shoot it down my throat! Give me that fucking cum!" then clamps her mouth on my dick and sucks the head and then pumps the hell out of my cock.

It felt like everything I owned pumped out of my dick. I mean I see her fucking cheeks swelling from all the cum and she sucks it all down and pumps my dick and it's fucking bucking and pulsing like mad.

When I'm finally done she pops my dick out of her mouth and keeps up the dirty talk, saying "That's my baby. Gave me some much hot cum."

I found out later on her and a couple of her girlfriends had had conversations of how to rock a man's world and that we loved women who fucked and spoke like porn stars.

I still get hard just remembering that day. Fuck do I miss her.
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Yesiknow1970 Professional Jackinchatter

1136 posts since 2016-10-20
41 year old heterosexual from Glasgow
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Think this was my best ever and it happened quite recently



We played around for a bit and she stripped for me. We've been shagging with condoms lately but neither of us like them

The foreplay was great and I had my hands all over her shaven pussy. She started to turn over so I pushed my luck and started rubbing my cock over he ass

She loved it so I stuck in in her ass and she loved it. She loved my cock in her ass and my hands all over her.

At one point I stopped and could feel her pushing back to get more of my cock up her ass

She'd never done that before!

I moved her hands to her pussy and told her to play with herself.

She lay on her side rubbing her pussy as I thrusted my cock up her ass and groped her tits.

It was amazing feeling her cum as I slapped my cock up her ass and she rubbed her clit.

When she came she said that I couldn't put my cock in her - I didn't want to!

She lay on her front while I wanked and cam loads over her big white ass.

Such a good night!
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BillC213 Skilled Jackinchatter

511 posts since 2014-01-30
64 year old male from USA
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Besides a drunken night of ass fucking my hot girlfriend long ago. I somehow was able to enjoy a double orgasm while jacking off one night. Wish I knew how I did it but i know it was the best feeling my cock has ever brought me...
Bill C.
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normalknob Professional Jackinchatter

1086 posts since 2014-05-01
58 year old from New Zealand
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No doubt about this one.

It was a girl I was just starting on a 6-month affair with. We'd been out with colleagues and were flirting so much. By the end of the evening I gave her a lift home and we talked a bit dirty to each other. In the end she said she wanted my cock in her mouth right then. She started sucking me as I was driving. Within a minute I had to tell her to stop as I was gonna crash.

We found somewhere quiet to park and she proceeded to give m,e the most amazing BJ i have ever had. It was insane. And I had the most intense orgasm I've ever had. She said she'd never had anyone react to a BJ like I did. And she swallowed every last drip. Just fucking awesome.
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winkThe best one I ever had was the first one I had in the shower with my 11 year old cousin (boy), me 16, who entered the shower with an erection. It was the first time I had ever seen a naked man and he was already hard. I got very hard and I came almost immediately, without wanting to, on his belly, it was the best orgasm of my life.
The next day with my mother's brother, 77, the same thing but this time I was on my back. Almost as much pleasure as the first one. In those days he was pumping out milk in torrents with those long, super-intense cumshots.razz
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HornyAllDayJacker Novice Jackinchatter

71 posts since 2023-08-18
54 year old from Canada 🇨🇦
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BRULANMO said:
winkThe best one I ever had was the first one I had in the shower with my 11 year old cousin (boy), me 16, who entered the shower with an erection. It was the first time I had ever seen a naked man and he was already hard. I got very hard and I came almost immediately, without wanting to, on his belly, it was the best orgasm of my life.
The next day with my mother's brother, 77, the same thing but this time I was on my back. Almost as much pleasure as the first one. In those days he was pumping out milk in torrents with those long, super-intense cumshots.razz


So ... you were 16 and had cock play with your 77yo uncle? I had similar... so hot
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