What’s the oldest chick you had sex with

[TommyGavin 788]

Not including present day and wives/GFs 

When I was 19 and working in a bar I was banging a couple a couple waitresses in their 40’s. Ran into one of them the other day and she was still looking good. Would still do. Maybe not. 

[Pimpadeaux 2,266]

I was in my late 40s and met a 56-year-old woman on a dating site. She invited me to come out to her lakehouse, and she was hot. Had a great figure. I wound up spending the night. We went on to have some fun dates, but she turned into a weeping willow, so I had to break it off.

[patweisers44 697]

Totally shocked that reply #1 wasnt:

How old is your mom?

[TommyGavin 788]

3 minutes ago, patweisers44 said:

Totally shocked that reply #1 wasnt:

How old is your mom?

I banged your mom too. 

[TheNewGirl 1,031]

I was 21 and he was 35, maybe older? I can't remember. 

He turned out to be a major d!ck, I consider him my rock bottom in my dating life. 

[Strike 3,979]

1 minute ago, TheNewGirl said:

I was 21 and he was 35, maybe older? I can't remember. 

He turned out to be a major d!ck, I consider him my rock bottom in my dating life. 

Damn.  Saw that you posted in this thread and was hoping your response would have been more true to the question In the title of the thread.  :Sad:

[TheNewGirl 1,031]

Just now, Strike said:

Damn.  Saw that you posted in this thread and was hoping your response would have been more true to the question In the title of the thread.  :Sad:

All the ladies I've been with have been my age.  

[Bier Meister 1,514]

when i was 19.... hooked up with a 24 yr old

[Strike 3,979]

4 minutes ago, TheNewGirl said:

All the ladies I've been with have been my age.  

[BunnysBastatrds 1,918]

 I was twenty two. She was fifty five. Used to go to the widow’s bar for free drinks and music and the occasional I can do that. She was infatuated with me and demanded I go home with her. Iranian professor 34B. I don’t remember much when we got to her house. She literally attacked me on the stairs screaming for me to make her tell the truth and treat her like the slut she always wanted to be. Then everything is unknown from me. 
 

 Wake up the next morning with a need for beer. I hear this sound. I look on my stomach and there is a hundred dollar bill. Confused I look up and she’s taking polaroid pictures of me naked and smiling at me creepy. Me: Why is there a hundred dollars on my stomach and why are you photographing me naked.  Proffesor Shaw: Avter you promised to make me tell the truth you said that you charge fifty dollars an hour.I figured I’d get a trophy to show all my friends. And I’m keeping your underwear also. Need a ride home?

[RaiderHaters Revenge 3,585]

I was 19 she was 48

as I am older I was 45 she was 60

[Strike 3,979]

When I was about 24 I had some fun with a 39 year old chick. 

[IGotWorms 3,315]

I was 40 she was 48. Great lay too.

I’ve dated a few chicks that were 5-10 years older than me, but never way older. Kinda wish I had, when I was younger. They teach you things

[5-Points 2,729]

When I was 21, I dated a 32 year old chick for a few weeks. She reminded me of Bo Derek. I think she had recently broken up with her boyfriend, and I was the young stud she chose to get back at him with. 

 

 

Also, another time, I was going through a slump and went out to the bar to get drunk. I ran into a friend of mine (girl) who was out with another friend of ours mom. I ended up banging her in a car in the parking lot. I was early 20's, she was late 40's mebbe early 50's. 

Busted that slump and went on a tear. 

[MLCKAA 395]

38 minutes ago, TheNewGirl said:

All the ladies I've been with have been my age.  

[TommyGavin 788]

1 hour ago, TheNewGirl said:

All the ladies I've been with have been my age.  

Wait what ????

[TommyGavin 788]

1 hour ago, Bier Meister said:

when i was 19.... hooked up with a 24 yr old

Ha. I took a 25/26 to the prom and after party at the beach I was to consumed with getting high and she was not into that so my younger buddy brought her home. He fvcked her. Did I mention she was my bosses daughter- I eventually got fired (for banging another chick at work). 

[dain11279 928]

[gfiafp] 18 [gfiafp]

[WhiteWonder 2,172]

53 (I was 34)   .   46 when I was 25 was the largest gap. 

[MTSkiBum 1,594]

26 ish? I started dating my wife when I was 29.

[WhiteWonder 2,172]

Just now, MTSkiBum said:

26 ish? I started dating my wife when I was 29.

and she hasn't aged? 

[MTSkiBum 1,594]

1 hour ago, TommyGavin said:

Not including present day and wives/GFs  

Reminding a poster of the rules of the thread

[TommyGavin 788]

So the other chick was very complicated- bar slut. No daddy. Mom was a slut. 
Anyway we were same age 20/21? And she moved in with a guy in his 40’s because she needed a place to stay. We were still ##### on the side. Car/motel but one day we went to her place. Second floor apartment and he came home for lunch ! I had to grab everything and jump out the back window- I made it out but sadly he recognized my car and he beat her up. She moved out and was still my 2AM last resort. 

[HellToupee 749]

Man I was a big poonhound when I was young but had my standards. Don’t get me wrong, I went pigging but nothing like some of these horror stories 

[TommyGavin 788]

1 minute ago, HellToupee said:

Man I was a big poonhound when I was young but had my standards. Don’t get me wrong, I went pigging but nothing like some of these horror stories 

So dare we go the other way ? Youngest gap ? And no pun intended when I say gap. Strictly age. But if you want to describe the gap I’m all in. 

[WhiteWonder 2,172]

16 minutes ago, MTSkiBum said:

Reminding a poster of the rules of the thread

touche, touche.... i guess that would push a lot of these guys above 70. 

[WhiteWonder 2,172]

23 minutes ago, HellToupee said:

Man I was a big poonhound when I was young but had my standards. Don’t get me wrong, I went pigging but nothing like some of these horror stories 

which horror stories? 

man, my 53 year old was a petite puerto rican-italian milf with nice fakes and an amazing ass. may have kept a vid or two. I messed that one up. She wanted something casual but consistent and I wasn't available enough.

   There was also a 8/10 Korean who I met when she was 49 (looked 29) and dated for 2 years. Shy but wild after a drink or 2.   The 21 year age gap when I was 25 and she was 46 was maybe a 7 but kicked up a notch because she was my boss

[TommyGavin 788]

I agree. No horror stories here. Except maybe me watching GF’s slut mom getting railed from behind in her kitchen by an on duty cop that would eventually give me an escort home. Ah the 80’s. 

[shadrap 117]

I'm older so maybe a 10 year gap between us(she being older).  Attraction, booze, situation?  give it a shot.  never had a bad lay, including some big ladies.

[jonnyutah 122]

2 minutes ago, TommyGavin said:

I agree. No horror stories here. Except maybe me watching GF’s slut mom getting railed from behind in her kitchen by an on duty cop that would eventually give me an escort home. Ah the 80’s. 

18 year old me: when you say from behind do you mean...

 

Current me: did they at least use some Lysol wipes on the counter after because that isn't very sanitary, especially if she was a slut. That could be multiple specimens. 

[Strike 3,979]

No horror stories for me either.  Now if you start a "fattest chick you had sex with"..........

[TommyGavin 788]

12 minutes ago, Strike said:

No horror stories for me either.  Now if you start a "fattest chick you had sex with"..........

Ah Gina was also the fat chick that we all banged when we struck out with the hotties. Probably 250. But could suck the chrome off a trailer hitch. 

[Engorgeous George 1,176]

I've never been with a woman older than me.

[TommyGavin 788]

2 hours ago, Engorgeous George said:

I've never been with a woman older than me.

Funny when I was in my early teens “all” the younger neighbors daughters had a thing for me. Never banged any of them. 

[Reality 2,710]

Hrmm, interesting question. No more than 4 or 5 years older. My wife and I have been together since I was 23. Married at 26.

I wasn't adventurous enough to consider women much older before I met her. Probably a mistake on my part. Of course, @ < 23 years old, finding a willing partner your own age didn't take much effort.

[kilroy69 994]

I have went 20 years on both sides.  20 years older than me. I banged a 44 year old when I was 24. 20 years younger when I banged a 19 year old at 39. 

[jerryskids 5,206]

1 hour ago, Reality said:

Hrmm, interesting question. No more than 4 or 5 years older. My wife and I have been together since I was 23. Married at 26.

I wasn't adventurous enough to consider women much older before I met her. Probably a mistake on my part. Of course, @ < 23 years old, finding a willing partner your own age didn't take much effort.

This is basically me, except no more than 2 or 3 years older.  Started dating wife at 23, married at 26.  In fact she is 1.5 years older than me, and I joke that she is the only girl I've dated who is older than me.  I had plenty of hookups prior, but they were all in my age range.

My best friend from my hometown used to bang cougars all of the time.  I remember one time at a club he pointed a few out to me who were looking to hook up.  In hindsight it felt like fight club -- once he said it I could see what he meant, but I had never noticed, I guess because my antennae weren't looking for horny 40-sumthins.

In hindsight I wish I would have ventured into those waters a few times for the experience, but oh well.   

[IGotWorms 3,315]

13 hours ago, TommyGavin said:

Ah Gina was also the fat chick that we all banged when we struck out with the hotties. Probably 250. But could suck the chrome off a trailer hitch. 

Deuce, deuce and a half — not bad!

[shovelheadt 62]

Don’t know her age, but when I was around 29-30 years old, I had to host some out of town employees. During a night of karaoke/darts, the oldest of the gals took me outside to smoke some weed. As I didn’t smoke normally, the effect was significant. Long story short, she abused my paranoid corpse later that night. I remember her saying she was a grandmother so at least mid 50s. 

[Alias Detective 1,179]

Me 21

She 2 x my age + 1 = 43