When my cousin told me out of everyone that's blown him and blowing him now even his girlfriend, no ones blown him like I do and that he loves when I blow him. He was the first to tell me that, but not the last.

 

Sweet Jesus! That is fucking hot! What a good girl you are!

 

So many things could apply here... Obviously losing my virginity is a big one.

First time joining a mf couple.
First time getting my dick sucked in a public place.
First time with two girls, (I have that story up to read).
First set of twins.
First set of triplets.
First orgy.
First time fucking someone in public, (At a local "nature area", in a wooded area off the path).
First time I fucked a coworker.
First time I fucked a coworker at work.
First time I fucked a famous person.
First time I was able to stay hard and keep going after cummings. (Was a threesome that lasted about 20 hours, with only short breaks here and there to rehydrate.)
In February I was at a convention in Boston. The weekend was filled with so much sex that I had to take two weeks off to recover.


But I think my current proudest was, just a couple weeks ago I met a group of five girls on the bus, all between the ages of 18 and 20. We flirted like crazy, walked around the mall together, and eventually went back to one of the girls place. Three people is a threesome, four people is a foursome, but what do they call it when six people are fucking? Whatever it is called, it was exhausting, and damn amazing. One day down the road, when I'm on my deathbed, I will look back on the day I fucked five girls at once, smile, and die a blissful man.

 

I think one of my proudest was when I seduced a 27 year old mother when I had just turned 18. Near 10 years age difference that early in our ages was an accomplishment I think.

 

Bumping so we can hear some more great moments

 

My proudest moment was giving my first girl friend an orgasm during intercourse. I felt like "the man". Maybe "a man".

 

My life is half over and I've got nothing.....

I was married to a refusing narcassist for way too long and have been single for about 8 years. Has been about 11 years since I've had any form of human contact at all. This is a pain that I wouldn't wish on anyone.

So not actually answering the question but my proudest sexual moment will be when and if I can conquer my anxiety and esteem issues and someday spend some intimate time with someone.

Sorry that wasn't much of a turn on for anyone.

 

When I gave my first blowjob to a guy lol

 

Greatest sexual pleasure was bedding the first and only woman I loved - the only time I believed I was in complete control and wanted my partner to find new sexual highs.

 

It was the evening I finally met and played with my first guy. I picked him up from school, drove him to his place and got started. He was the first person to rim me and I came on his face way too fast! He got nervous and couldn’t stay hard for too long when he was fucking me, but he did fuck me! From there, it is all downhill....

 

I have a couple...

The times I gave a girl their first orgasm from intercourse....
And proving to a girl that was sure she could never have multiple orgasms... I ate her out for over an hour.... She lost count t at 15 ;-)

 

I was given a 4" Participation Trophy made of plastic, spray-painted with shiny gold paint, for being part of the team, although I only ever played when the better guys needed a rest, and never even came close to scoring a goal. But at least I wasn't the water boy.

 

Im not super crazy. Soo id have to say when I'm fucked my ex and then the next day got a blowjob from a different girl. Called it a dick shower. Lol

 

When ever I got my wife off

 

Some best moments:
*My supervisor at the time...had never cum before via vag intercourse...started bawling afterwards...our first time...she was a brunette hottie, but we only lasted about a yr...
*Just a couple of months ago, a black guy upon sucking me off said he never swallowed so much cum in his life...
*Long time ago, I was loafing around in a super huge adult theater when I saw a 6' tall, long blonde haired, beautiful goddess walk in. She was only wearing (I later discovered) a black trench coat and was accompanied by 2 men, who were also wearing all black clothes...we were about the only people there that afternoon...undeterred I boldly walked up to her...and minutes later she was bent over...even then I had to stand on my tippy toes to bang her... Anyway, I came quickly...upon disengaging she sat down, opened the coat not so much to display her firm, gorgeous body, but to spread her long shapely legs...I ate her out 'til she came.
She was so pleased that she said my reward was a blowjob...she grabbed my bare ass and pulled me to her. The two guys continued to watch as she began to suck my hard cock...she was very talented...when I came in her mouth she swallowed it all and still wanted more...she kept sucking my hard cock, until I couldn't take any more...I literally pulled my cock out of her greedy mouth and when I did, the suction pop was so loud that it literally echoed in the cavernous theater...we both froze when that happened...after a couple of seconds she gave me thee most beautiful, endearing smile that I've ever received...I then left...never saw her again.

 

when I got an 8" cock down my throat with out gagging

 

Ages ago I hade a long distance relationship. I was about 27, she 37. That one time I arrived at her place at late night. We went straight to bed and had some good fucking. She often came "just" by vaginal intercourse, so it was this time too. She came pretty heavy and she stopped doing everything all of a sudden, just lying there with her legs shaking like crazy, unable to do anything, enjoying her huge orgasm she obviously had. Her mind was somewhere else but not in this room.

Fascinated I was looking at here and waiting for her to come back to reality, which took a moment. When that happend, we went on to round two (which was for me still round one as I didnt came, just to mention this). So we went on fucking, as she, after a while, came a second time (needless to say: I didnt till then). And this time was the heaviest cumming of a woman I ever saw: She pushed me off her, her legs were shaking like crazy, her pupils nearly completely dissapeared, she was just mumbling something I couldnt understand and she was completely on her own, totaly forgot that I was in this room too (reminded me a bit of the movie The Exorcist). This moment lasted for a real long while.

The fascination of this scene was replaced after a while of the frustration that I was laying here with a hard on, fucking her the hole night and I still didnt came and she seems not comming back to this world that night. So I turned around, trying to sleep, feeling a bit pissed off to be honest. I felt asleep and after a while (I dont know how much later) I woke up from the feeling that my dick is just getting sucked. And there she was, giving me a blowjob and then I fucked her a third time and this time she let me cum in her and made me a damn happy man. Not to forget she came as well. Of course. What a woman that was!

 

I did 14 hours once, I can agree with the recovery time completely!