Guys, what is the oldest woman you had sex with?

[Anonymous]

What is the oldest you fucked with and how old were you?

[Married-in-PA]

My wife is 45, but I am almost 44 now.

HOWEVER, when I was just a Padawan Learner (at 21), I nailed, I shagged, I rode rotten an extremely horny MILF that was in heat, and she was 42 or 43 at the time (as I recall). It was some of the best Sex I have ever had. It's still in my jerk-off go-to bank. It was only one week-end, but that was ONE HORNY LADY. It was like 8 times that weekend, not including the handjobs, blowjobs, etc.

[Twolips]

Up to 40

[Asker]

How did it happen?

[knotuptoit]

my ex wife! my new wife is 29 years younger but my first experience should count for something. i was 9 she was 13. her step daddy was teaching her all these fun sex things and she was passing them on to me. sorry bastard! so i guess she would qualify as the older woman in my life. if she is still alive she would be around 68-69 i guess

[MrOracle]

The oldest was 47 (but looked like she was in her 30s) - I was 42 at the time.

The next oldest was 36, when I was 43.

[Orion1015]

The biggest gap I've ever had between ages was fourteen years. I was 19, at the time, and she was 35.

Currently, I am dating a 39 year old woman, so she is the oldest, but we have a smaller difference between our ages.

[Asker]

I thought she was 33?

[Orion1015]

I'm sorry? Who was 33?

[Asker]

The woman you slept with at 19. My women institution is telling me she was married but was living a shitty marriage., but that still doesn't give her the right to act like some slut. I think cheating with young guys is very scummy and degrading to the man, but i guess i could be wrong.

[Orion1015]

As a matter of fact, she was in a shitty marriage, yes. I realize now, being more mature than I was then, that it was kind of a slutty thing to do; you're right. However, at the time, I was getting laid by a sexy, older woman, who thought I was better in bed than her husband. I thought it was great, but I was just a stupid, horny kid, lol. She was 35, though, because I remember people telling me "when you were four years old, she was a senior in high school." If I answered this question before, then it was probably a typo, on my part. My phone has a very touchy keyboard, and I have fat fingers, lol.

[Asker]

Lol, so she was 16 years older then. Not 14. I am NOT blaming you. I never blame the homewrecker. It was very slutty to do it with a 19 year old tough,.

[Orion1015]

Oh, holy crap, I failed basic math, lol. :(

[Rawrzz]

30 year old when I was 18. I was pretty proud of it.

[Asker]

How did you get together?

[Rawrzz]

I had a 30 year old weed dealer/Electrician who was friends with her. I was friends with him, went over his house every day and smoked with him. He didn't like smoking alone. So we went swimming at her apartment complex. Then he had to go pick up his kids. Mmm. I don't remember what happened much after that. We talked, I got kinda nervous, so I smoked a joint. One thing led to another. Then she drove me home in the morning.

[bradderstheclaret]

I was 22 and slept with a 44 year old co-worker.

[Anon833]

I was 19, and she was 57.

[thisGUYknows]

She was 42ish? Don't remember. I was 27. The funny thing is that the roles were totally reversed. She was chasing me, kept giving me compliments and everything. I kept saying no until I just gave in one day when I was super bored. I felt like the girl in this scenario lol.

[10dsw]

27, I was 20.

[joeb73]

my wife she is 40

[jc1982]

43 she was 10 years old than i was and it lasted for almost 13 years before we got divoraced. she was 29 when it started.