Biggest age differences in dating you know of?

when i was 18, i had a 48 year old 'friends with benefits' situation with a married woman. the husband was 69 years old, couldn't 'cut it' in the bedroom anymore and was more than happy to lend his wife out to someone who could handle that department for him. no cuckold situation, so he wasn't present while i was doing the deed, but we all partied together.

Well hell.
 
I know a couple that is 17 years apart, but that seems like nothing on this thread.
 
There's truth to this, but also variables. I didn't have a positive MILF encounter on the first couple of times, in fact one was one of the worst sexual experiences I ever had. However, later on I met a MILF and suddenly my eyes had been opened. All the stories and stereotypes were shown in the brand new light of experience.

In contrast, some of the younger ones don't necessarily have the skills, but they have a sort of unhampered enthusiasm that's hard to find elsewhere. It seems like younger ones tend to try to do what they think you want, and sometimes they're right, while older ones know how to get in sync with your rhythm and, most importantly, alter it if need be while younger ones have a tendency to sort of randomly buck wild. It's all about timing, goddammit.

That unhampered enthusiasm was once a huge draw and now the further along I go the less I can play along with young women. There always comes a point where I just want to tell them to shut up. Its not that young women talk any more than older women they just don't fucking get it.
 
That unhampered enthusiasm was once a huge draw and now the further along I go the less I can play along with young women. There always comes a point where I just want to tell them to shut up. Its not that young women talk any more than older women they just don't fucking get it.

Nailed it...
 
when i was 18, i had a 48 year old 'friends with benefits' situation with a married woman. the husband was 69 years old, couldn't 'cut it' in the bedroom anymore and was more than happy to lend his wife out to someone who could handle that department for him. no cuckold situation, so he wasn't present while i was doing the deed, but we all partied together.

48 eh... Hotter or less hot than Peggy Bundy?
 
A teacher I had in college was in his early 80's his new wife was a 23yo model.

Yeah.... he had money.
 
Interestingly enough, it's only my gay friends and family who have been in relationships of vast age differences. Not sure why...

Dat sugar daddy.

[YT]ISGpceOaexU[/YT]
 
Guy 43 years older than the woman.
 
I knew a 40's something guy at this church I used to go to back in HS who was dating a 17 year old turning 18 who lived on this farm. This dude was a farmhand who obviously had been working on this setup for a while!!! He became good friends with her parents too I guess.

The weird thing is he was super quiet and shy and then one day I heard they were getting married.

I have nothing against age discrepancies in dating but this whole situation really creeped me out. It was just all very strange.
 
My best friend just turned 41. His wife (common law) is turning 25 soon, I think. It seems to work for them. I would never date anyone that young though. Another buddy of mine who is also 41 is marrying a woman who is 26, I think.
your buddies are my heroes - they give me hope...lol

:icon_lol::icon_lol::icon_lol:
 
I knew a 40's something guy at this church I used to go to back in HS who was dating a 17 year old turning 18 who lived on this farm. This dude was a farmhand who obviously had been working on this setup for a while!!! He became good friends with her parents too I guess.

The weird thing is he was super quiet and shy and then one day I heard they were getting married.

I have nothing against age discrepancies in dating but this whole situation really creeped me out. It was just all very strange.

Could you imagine being the father of that 17 year old girl. I would flip
 
Could you imagine being the father of that 17 year old girl. I would flip

No, I can't. Just a really weird situation all around. Maybe he was the first guy besides her dad she had ever seen, lol. I mean he had to be around or close to the father's age.
 
Yes I know someone very close (family) to me that is a 30 year old dude dating a 47 year old woman.

Its hard to deal with because it is embarrassing for the rest of us. I completely understand their relationship is between them in their world. We're just really weirded out by it.
 
Yes I know someone very close (family) to me that is a 30 year old dude dating a 47 year old woman.

Its hard to deal with because it is embarrassing for the rest of us. I completely understand their relationship is between them in their world. We're just really weirded out by it.

How is his relationship embarrassing to you? You're not dating the 47 year old
 
She may had perfectly huge tits installed. And she cant get pregnant!
 
Yes I know someone very close (family) to me that is a 30 year old dude dating a 47 year old woman.

Its hard to deal with because it is embarrassing for the rest of us. I completely understand their relationship is between them in their world. We're just really weirded out by it.

Seen a Mother disown her oldest son because he married a women too old to bare children. His whole family and even friends are taken aback by their relationship.
 
Seen a Mother disown her oldest son because he married a women too old to bare children. His whole family and even friends are taken aback by their relationship.

I'de disown my son if he made that mistake, not kidding. It's a horrible mistake....

however if I were 40 and married a 20 year old.... that would be awesome.
 
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