Biggest Age Difference You've Had With Sexual Partner

collegeguy13

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Biggest was definitely a college professor who’s class I had taken freshman year. We didn’t hook up until a couple years later but he was probably 65 or so and I was 20. I saw his profile on Scruff and played it off like we didn’t know each other. We gave massages and blew each other, after we talked about me being in his class. Pretty hot, I’ll still jerk off thinking about it
 

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I've always dated younger men, given I don't look my age. The largest age gap—10 years.

Unfortunately the stigma of being labelled a Cougar/ Puma is offensive.
It's a double standard.

Men who date younger women regardless of vast age difference are likely to be tolerated by societal norms— compared to the latter. (My reference point is two consenting adults 18 years or older)
 
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Blues99

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I slept with someone who was in his 60's when I was 18. He was someone who was respected in my field of study at that time, and had a massive dick. We were in a Jacuzzi together and he let me feel his thick dick... it was like my wrist. We went to his place afterwards and had sex.
 
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BigBen

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My current wife, almost 8 years younger. Out kicked my coverage biiiig time hah.

When I was younger, it was many women many decades older than I am....and has time gone by...it is still women who are older than I...and some younger by a few years or a few decades...but many now are several decades younger than I. Some women...IF they can do so discreetly and feel safe and comfortable doing so...even. married, single, engaged, divorced, boyfriend...whatever...especially if they have "heard" from friends, coworkers, acquaintances, their hairdresser (several), sisters, cousins, aunts, and even a few mothers and daughters who told them....have eventually...some soon...others later...all. wanted to "meet" to "see". I never care about age at. all....never.
 
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HOU_HEADHUNTER

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Younger men (18 and older) tend to actively pursue me. I on the other hand tend to actively pursue older. I think the oldest that I've engaged with was in his late 50s. That's roughly a 30 year age gap as it relates to me and older men. I tend not to go based on age but more so on how they present. The older men that I'm attracted to present much younger and still have a level of energy that matches my own.
 
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swingfun

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My wife is six years older than me but my biggest age difference happened when I was 24. I was in the air force at the time and a friend and I went out running around one night. We ended up at a club and this older woman came up and started chatting me up. Well after a couple of hours she invited me back to her place. My friend had driven so I found him and told him I had other transportation...lol. Anyway it was some of the best sex I had up to that point. Found out she was 49...so 25 for me.
 
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I don't know the exact age difference. He was at least 20 years older than me, possibly as high as 25 years older than me.
 
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