Biggest Age Difference You've Had With Sexual Partner

[HunginLondon]

I met a Dutch guy when I was 19 - he was 45. Intense sexual chemistry and amazing orgasms! His huge cock at a sauna caught my attention and no regrets.

 

[Tight_End_SC]

40 years difference. The experience was underwhelming but not because of the age, he called me grandpa HAHAHA!!!

 

[Flowersplease]

Probably around 40+ age difference has been the largest difference. I like older men that said

 

[tewwgb2]

As I've aged, I've found that I enjoy pleasing young men (over 18). So I've had a number of hookups with late teens and twenties wanting a "daddy". One 18yo virgin boy wanted me to "train him" to be a great bottom before we went off to his college for his fun, so I happily obliged. Every man needs a hobby. I suspect it was a 40yr difference at that time.

Some people really frown on the big age difference (power dynamic), but as long as you were kind, took your time and it was legal & consensual—I see it as the younger guy being very lucky.

When I was 19, in college and freshly out of the closet, I had a daddy who was 48. He knew I was a virgin and had 0 experience with guys. He was kind, patient, and we both knew exactly what we were doing. Everything was upfront. I look back on him fondly as he really showed me how to take a good sized cock, how to give good head, how to clean/douche, and even how to switch hit, and top him. I kept in touch with him years after I moved away from the college town I met him in. I always felt very lucky, because I could have lost my virginity to a young dude who took things for granted, or someone who had no feelings for me at all.

 

[illusionguy]

I started young and my biggest age difference was in those early days. He was a regular hookup and was about 55 years older.
My first long term relationship I was 23 and he was 42. I have had others where I was the younger with a 10 - 15 year difference and also more where i was the older one with a 10 - 20 year difference.
About 8 years ago I had a 6 month thing with a 19 year old guy while I was 62. He wanted to explore more of his sexuality and I was able to help him with that and to realise that he was a total bottom.

 

[DuffyW]

A couple of months ago I was with a guy 45 yrs younger than myself me being the older one.

 

[WadWorshipper]

Some people really frown on the big age difference (power dynamic), but as long as you were kind, took your time and it was legal & consensual—I see it as the younger guy being very lucky.

When I was 19, in college and freshly out of the closet, I had a daddy who was 48. He knew I was a virgin and had 0 experience with guys. He was kind, patient, and we both knew exactly what we were doing. Everything was upfront. I look back on him fondly as he really showed me how to take a good sized cock, how to give good head, how to clean/douche, and even how to switch hit, and top him. I kept in touch with him years after I moved away from the college town I met him in. I always felt very lucky, because I could have lost my virginity to a young dude who took things for granted, or someone who had no feelings for me at all.

That's perfect! Yes, I always aspire to be that "daddy", especially with virgins. I once spent 25min getting fully inside a boy that wanted every inch of me badly but had trouble relaxing. We eventually had a great session, and he wanted to try everything. . There are plenty of asshole men that consider a young guy a "conquest" and thinking it's all about domination, but not every boy wants that. I treasure young men (of college age, especially) and treat them well.

 

[HungBtmVegas]

Update: Exchanged numbers with a guy in his 70s at the gym just now

 

[daddiesbarebackslut]

Had fun with a few guys about 40+ older then me, was great fun.

 

[DuffyW]

I have always had fun with guys 20 plus years younger than myself.

 

[parkadog]

22 years difference

 

[terroi]

All of the men I've been with have been 20+ years older than me. Fucking love older men.

 

[deleted471226]

22 years older than me

 

[tewwgb2]

Bump

Seeing if anyone has new stories about being with someone much older or younger, especially if it was your first time or losing virginity.

 

[Sydnari]

My first was with guys 28 years and 33 years older me. We did everything except fucking on that day.
Then 2 years later, I was introduced to bunch of older hot guys for old young orgy party. One of them were 53 years older than me.

 

[tewwgb2]

My first was with guys 28 years and 33 years older me. We did everything except fucking on that day.
Then 2 years later, I was introduced to bunch of older hot guys for old young orgy party. One of them were 53 years older than me.

What did you do with the older hot guys? Was this your first time having anal?

 

[Xyprgj7]

More than 12 of difference. And taught me more about life itself

 

[Derringer]

She was definitely of legal age but I was 15 years older. She had a couple of boyfriends before. She expected me to be - a) well endowed ( because of my general physique and seeming confidence) - b) a good lover ( because I had been with plenty of women)
She ended up being surprised/ shocked at how tiny my penis is and totally disappointed when after some rushed foreplay I came in about three strokes when I tried to fuck her.
She told all her girlfriends about how bad I was.

 

[spring11272000pic]

Probably 35 years older. I’m 59 now and finding out I’m the older man now. Always enjoyed older as a preference

 

[Sydnari]

What did you do with the older hot guys? Was this your first time having anal?

We tried dp but wasn’t successful but we had lots of fun in 2days at an isolated farmers house. My first anal sex experience was with the 2 guys who delivered me the first sexual experience. They trained and stretched my anal day by day.