Whats the oldest woman you ever had sex with (age difference)?
 

When I was 26, I dated a 46 yr old for about a year. As you can see from my posts, age is no barrier for me. Anyone else date a significantly older woman?

I was with 35 at 23, she was just a fuck though. Called her Ole' 35er and she was good at was she there for.

Gotta love those cougars.

She was a _hot_ 36. I was 21.

I left that relationship a bit more educated than I entered it.

Gotta love the milfs huh?

I had a cougar during my late teens, but I don't remember how old she was. Mid-thirties.

i was 17 and she was 28 :) and she was pro rugby player. she was hot as hell, but now she looks like a dyke. she still plays on scotish national team.

I was 23, she was 33 (or so she told me). Married too. She used to come over, fuck and then feed me and do my laundry. he he

I've been with women 21 years older than me and 22 years younger than me

Shit at 20 yr difference, I still have the record. She was my aunt's hot friend and actually babysat me when I was younger...

when I first moved to ATL, she was on telepersonals. I was 34 a noobie to the phone thing. She showed up at my house she was about 58 yrs old, I figured it beats jacking off. lol

I was 22 and she was 46

a tie at 44 yr diff.

I was 23 and she was 38 and married to a woman for 18 years. mmmm tight lesbian cougar pussy. I would not be lying to you if I told you she was a hot blonde cheerleader in highschool. Thats the truth I swear on my fist born. I still jerk off to that shit mentally. I also pimped a 37 year old when I was 24. I was doing door to door sales and I hooked up on some whore. I went over there again and this big black guy kicked my ass lol

damn you guys had some real milfs huh :)

ooops I mean 24 yr difference

I was 20, she was 39.

Oldest I had was on a cruise ship... I was 34, she was a 49 year old lawyer. That same week I also had 20 yr old college chick... Covered both ends of the spectrum for me in a short time... Both were good and bad in their own ways...

45, I was 25

When I was 22 I hooked up with a 52 year old, so 30 years. I still love the older women, and would hook up with a 65 year old if she was hot and had a nice body. :thumbsup

When I was 22 I met this hot 35 year old woman. We went out for a couple of months till she got bored of me and found another younger guy haha

It was an interesting experience but I wouldn´t say I had a great time. I didn´t like her personality as much as the sex. I guess she felt the same hehe.

I was 28 and she was 69. She was hot though (especially for a old bitch). She had a great figure and a nice set of fake tits. Best sex I ever had too! My only complaint was that she really did smell like an old person. Had that old folks smell! What causes that??? Is it like old skin or something?

wtf? 69, dude, are you serious?

SERIOUSELY, LETS DRAW A LINE!

Ya, I'm 100% serious. She was hot though and I think if you saw her you'd seriously consider hitting that too (especially if you'd had as many drinks as I had that night). I met her at a bar where she was with one of her much younger friends. My friend liked her friend, so I was entertaining this gal to help my friend out. My friends all liked hanging out with me because I worked in the porn industry and they wanted me to introduce them to porn stars (which I did when they were visiting my studio) and they all expected that I was a pickup master for some reason when we went out, so I was always under pressure to help them get setup before the night ended.

My friend and I both lived/worked in the same building which wasn't far from the bar, so we invited the gals back for drinks. My friend ended up scoring so I was stuck with this old chick in my loft all night. Yet, I didn't much mind as it was some good sex. I've been with a lot of people in my life, and she ranks up near the top. I was banging her hard from behind and slapping dat ass as I normally do. I wasn't sure if her hair was real or not and even if it was I feared it'd come out so I didn't pull her hair like I normally do.

This is going to sound sick, but she had dentures. I had heard stories about women with them and it's true. I'll leave that part to imagination though. No joke.

32, and I was 14 :)

Does this get affiliates to sign up?

Man...everyone seems to love a good MILF (or GILF in Mickey's case). I was 26 and she was 44. Good times too. She wanted me to jizz in her and on her face all the time. It's nice just to have a woman know what she wants. :)

Damn..lucky bitch. Like one of those lucky kids that gets "raped" by his hot middle school teacher.

about 7-8 months ago or something i banged a 45 yo

I can top my own story though. Several years ago I had a 19 year old model named Sky. She originally came to me answering an ad I put in the local newspaper seeking models. The ad quoted "$100 per hour minimum pay" and continued with "if you were even average looking we will find you work within 48 hours guaranteed or just give you $100", so I figured everyone would "understand" what this was about. Then in walked Sky. So, I'm doing the interview like I normally do and video taping it as usual. I ask her "What type of modeling are you willing to do?" She responds that she is willing to do "anything". Good answer. I learned from experience to then ask the next question... "What type of modeling are you NOT willing to do?" Her response is again that she is willing to try anything, but then she adds "just as long as there is no nudity involved!" WTF! I immediately stopped the interview as it's obvious that this dumb bitch has walked into the WRONG studio. It's the end of the day and I'm pissed as I've wasted my time even doing this interview with this dumb bitch. I am as kind as I can be, but send her on her way.

Chance has it that the next day I get a call from a custom requesting a custom video with the model doing simple poses which didn't involve nudity. Normally I wouldn't shoot such a boring script, but it paid well (I charged the customer extra because it was so boring) and I had a plan. I call Sky and arrange for her to come in. She comes for the shoot and it goes well. All my staff are wondering why I am wasting my time shooting something so boring, but I tell them to wait and see. During the shoot several of the other girls are there and discussing with her what type of shoots they normally do. We shoot for 2 hours, and I pay her the $100 per hour and send her on her way.

Ok, so now Sky understand what type of company we "really" are, and a few days later I get a call from Sky asking if we can help satisfy a fantasy of her husband. She'd been married a year ago and her husband has a fantasy about seeing her getting fucked by a really old guy. The older the better she says. Sure, no problem. I place an ad in the newspaper seeking old men! I have many guys reply, but only 2 who are over 60 and I was really hoping I could get someone 70+. One was 62 and the other 65! Ok, I decide to test one of the 62 year old guy out as he actually looks older than the 65 year old and the contrast would look better on film. I need some extra guys for a gang-bang I was arranging so I put him to the test. We are shooting the gang-bang with a very hot 18 year old named Megan. This old guy obviously hadn't had sex in a long long time as he cums just as soon as she puts her lips on his cock! She doesn't even suck him, she just puts her lips on his dick and he cums! He didn't get a chance to fuck her or nothing! So I made him stand there and slap her ass and pull her hair while everyone else took turns fucking her and getting sucked off.

So, obviously he wasn't going to work. I then moved onto the next guy (the 65 year old). He's the only old guy left so I decide just to setup the shoot with Sky and risk it. It was about this time of the year so I decided to do a Halloween theme shoot entitled "Sex with the Dead". Video starts with Sky playing the Ouija board and commenting how lonely she is and wishes that she had a man, any man! You then see a cemetery at night and then we jump to a view of the ground where an old guy is coming out of the ground.

He walks zombi like into her apartment and fucks the hell out of her. At the end he's about to cum so I have him pull out and cum on her stomach so we can see it. He pulls out, cums, but nothing comes out. WTF? I move the camera up to his face and he responds with a classic response, "Not much juice in a corpse." I yell cut and all the staff die laughing.

So, this story beats it. 19 year old gal and a 65 year old guy! Captured on film on top of that!

I was 28, she was 49...

:1orglaugh:1orglaugh:1orglaugh OMG, I'm pissing my pants

I was 17 - she was 36 and my mom's best friend!

She'd spend weekends at my house and I'd bang her every time for about 6 months.

In the same time period I was bangin' my 33 yr old neighbor as well as a 23 yr chick in the next building AND my 19 yr old girlfriend!

Good times!!!!!!!!!!!!!!

:):):)

I was 31 she was 39.. not too much of a difference

lol I heard them being called Pumas

never been with an woman older than me :(

I was 24...she was 40....dirty girl...cum swallower..ate my asshole..after I fucked her a few times...she told me she knew my grandpa from his finance business..so it kinda freaked me out and I kicked her to the curb

42 at 24

over 50. she still looked good though

The greatest span in age? It was illegal... I am sure my mom would say she molested me but boys don't get taken advantage of, we get laid ;)