the oldest?

well this does not fit the question as i have fucked older but when I was 14 i was with a woman that was 29.

 

One night when I was 18 out at a bar hit on a 46 year old lady. She was loving it. Toyed with me telling me I was too young and it would be fun but she couldn't. I kept on and we went out behind the bar and fucked in her car. I'll never forget her big floppy tits and that big sloppy pussy. My young dick was slippin and sliding all around like fucking a mayo jar.

 

I was 20ish, she was 45ish. Imagine our surprise when her daughter (my age) walked in. It didn't turn out to be a hot mom-daughter experience. More like a milf-wondering-what-the-fuck-she-just-did experience. Nailed her a couple more times after that. She knew it was wrong, but she loved it.

 

I was 15 and it was my oldest sister's friend who was 23 at the time

 

I was 16 she was the neighbor and 49. She was average with huge tits. We did it for the next few years until I went to the military. Good teacher!

 

MYSELF!

 

I was 19 she was 42. She said I was a good fuck. We fucked in my car outside a nightclub. She let me cum inside her too. i thought she was younger. She asked me my age after sex. She told me she has sons my age. LMAO

 

19, she was 48, we screwed weekly until she was 58, and got remarried.

 

Age is just a number.

I think though, the oldest I have been with was a woman in her 40's

 

I was 18 when I hooked up with a woman I estimated to be in her 40's..I wrote a story about it: "I'm 18 and I like it".

 

Im 24 shes 49...best sex Ive ever had! She can deep throat without gagging and take it up the ass without crying! and just as a bonus shes a squirter!

our first time started in a mall parking garage were she sucked me for a while, once things "escalated" we found a side street with a trail that led into the woods, she drives a 4X4, and we fucked in the woods for hours! one of my best memories ever!!

 

I was 35 she was 30. I personally like younger women.

 

I was single and 21,she was divorced and 40.She was taller than me,blonde,long sexy legs that she wrapped around me while we fucked in her car. It was a one night stand.I dont even remember her name.

 

my wife's 10 yrs older.

 

50

I was 15

 

I was 18, she was 37. I met her at work, my id was hanging from my shirt right in front of my zipper. She walks up. Grabs my id stares at it intently from about 3 inches. Stands up and says its nice to meet me.

My favorite memory of her was her riding me and then saying. Oh my god I can feel you all the way up here...

It was all good for a few weeks till she introduced me to her husband at a company function. Doh!

 

Youngest (for complete sex with penetration) was 14, when I was quite a bit younger than I am now. Oldest was mid-60's, there have been several in that age range. I'm in my late 30's, first time I had a woman over 60 I was in my late 20's and she was great. I take a shot at older woman any time I get a chance, even though most women I sleep with are within 10 years of my age I like them at all ages, pretty much.

 

ages

well lets say my wife is 14 yrs older than iam so she is

 

Oldest girl I fucked is 31. At the time, we were 28 & 30. So, 2 years older than me. I didn't cum.

Fisting, on the other hand, I've done to a 47 yr old when I was 28. There was just no sex with it.

 

40....something. I'm going to go out on a limb and say 45 or 46.