Biggest age gap you've had in a relationship?

[JUICEDUP3]

mine was 12 years younger

 

[Brocksamson2.0]

my wife is 11yrs younger

 

[pesty4077]

My wife is 23 years younger.

 

[Goodfella1988]

Uhh this is an interesting one for story time. Back when Craigslist use to have their personals section up, cougars use to be on the prowl often, every night of the week. Well me being 17 and course and horny as fck had to check it out. From 17 to 18 fucked a ton of women in their 40’s to 50’s. I did end up learning my lesson tho after one cougar just about grinded my dick off. Honesty to god thought my cock had ripped near my balls she grind so hard.