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Oldest person you've had sex with ?

I'm twenty-three now but when I was nineteen, I was fucking two guys who lived across the street from each other. They were best friends, one was seventy-five and the other was seventy-seven. Met them on the Venice Beach boardwalk in California, when I was roller skating and noticed the older one would grab his dick and nod his head at me whenever I passed by.

One was an insatiable bottom who would always make me plow him until he came without ever touching his dick. And the other was the best at sucking me off without his dentures. Wish I had a chance to have them both at the same time but they were always really adamant about keeping separate, haha.
 
Oldest guy I slept with was mid twenties (not really pushing it I know).

Other than that I made out with a guy in his forties.
 
30. Only because I haven't found the right 30+ guy to spend the night inside my sugar walls. :gaysex:
 
philanthropy said:
I'm twenty-three now but when I was nineteen, I was fucking two guys who lived across the street from each other. They were best friends, one was seventy-five and the other was seventy-seven. Met them on the Venice Beach boardwalk in California, when I was roller skating and noticed the older one would grab his dick and nod his head at me whenever I passed by.

One was an insatiable bottom who would always make me plow him until he came without ever touching his dick. And the other was the best at sucking me off without his dentures. Wish I had a chance to have them both at the same time but they were always really adamant about keeping separate, haha.
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Why would you go for that?
 
From their twenties to late 60's/ early 70's.

Variety is the spice of life, baby!
 
last year when i was 18 i fucked a guy in his mid 30s.... solidifying my interest in guys my own age
 
BearDaddy said:
HWCaleb, I take it you topped him?
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yes, yes i did.... while i appreciate that many guys like it in their bumbidy bum i have not acquired a passion for such a way to learn a guys dick size,lol.... but always willing to learn:sex:
 
NineOfClubs said:
After my own heart... (*8*)
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One very fun guy I hooked up with was an older man I met on a fetish site. He had very interesting pics on his profile, but always headless. He was honest about his age, just didn't want head shots.

So I meet him at his generic little house out in the 'burbs. I thought I mistakenly went to the wrong house when he answered the door.

There was this cute little grandpa-looking guy. (Very fit, mind you, but very kindly grandpa-looking). I was so embarrassed.

But he knew my name, so I knew it was him.

We had a long, extremely satisfying evening. I never look at 'grandpas' the same way again. :D
 
49, I guess my hands are the same age as the rest of me...
 
Not sure. Lilbit-kinda old? Didn't know humans can get that old in the first place.
 
Early 40's?

It was an odd circumstance, and I don't plan on going that much older than me again, but it was pretty decent.
 
Oh goodness, I need to search through the archives...

I think the oldest was in his 50s but he was a body builder and was certainly "experienced" so I'd let him do me again.
 
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