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Who is/was the oldest man you've had sex with?

W

Wizard 666

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Or to phrase it better, biggest gap from your age?

I'm 23, and all the people I've been with have been around my age cept one guy, who was in his early 40s. And call me crazy, it was the best sex I've ever had. We were technically a couple for a few months too. All my friends found it weird, but honestly, I very much enjoyed the love and affection.

How bout you boys? :)
 
when i was 19 i hooked up with a 45 year old guy and his 49 year old partner. both of them had really nice cocks and knew how to use them
 
ta make it hot ans get dudes real pumpin got make it long reply

but short answer older then me

thankyou
 
Prolly my partner, he's 57....I'm 54
 
For the biggest gap from my age, I will need to go younger. I hooked up with a guy 15 years my junior several times. (!)
 
Hum, barring the people whose ages I did not know (whose names I frequently did not know), the oldest man I've ever been with was 42, and I was 28. Before that I'd always dated people within two or three years of my own age; and that was also the last time I had sex, so I haven't had the opportunity to break that record.

It strikes me as sad that I'm now older than he was, and I thought him awfully old at the time. I wonder if I have Old Man Smell down there, the way he did? Maybe it's time to find out... any volunteers?
 
Hard to say when you're having anonymous group sex in a dark after-hours (way after) San Francisco sex club. Maybe 30 years?
 
I've only ever had sex with one guy older than me ... he was one year older and we were in an l.t.r. for five years in our early 20s.

The biggest age-gap was about 25 years younger than me when I was in my late 40s.


It's a continuous frustration to me that, whilst I am most attracted to guys around my own age or slightly older, no gay man of my generation is ever remotely interested in me.

Meanwhile, younger 'bi-curious' guys occasionally are attracted to me ... so I have to make do with them.
 
All been around my age; the oldest was 5 years older at 39 back in May.

-d-
 
I get crotch groped by a guy of 90 and I like it.
 
I was 46 years older than one boy. But, do rent boys count here?
 
I was 50 at the time and he was 63. Great guy, great kissing, great sex. If it wasn't for the fact that he lives a long way away I'd be all over him constantly.

-T.
 
I was 50 at the time and he was 63. Great guy, great kissing, great sex. If it wasn't for the fact that he lives a long way away I'd be all over him constantly.

-T.
 
I was 22, he was 55... I don't know, never found him to be that old while I was hooking up with him. He's pretty fit, young body but older face.

I don't know, but when you find yourself a really nice friend, the age doesn't seem to bother.


Now, when I'm no longer with him and lost my passion and urge (I'm also with a younger guy than me) he does seem a lot older and I tend to notice it more. I find it odd how I notice his age and oldness more when we no longer hook up.
 
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