What’s the oldest female that you have knocked off?

I was 21, she was in late late 30s ,hood bitch I met off yahoo messenger when it was popular

Drove from Jacksonville nc to Trenton nj, I ain’t even know how hood that shit was.

She had a mean heavy ass and knew how to throw that shit back, she hit me up on fb a few yrs back

Bruh you drove 9hrs for some pussy..... In Trenton. You lucky you made it back home.
 
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Hmmm...The most upwards I ever went was probably about 7 years.
I think I was about 32 and knocked off a 38(?) year old. @17 I was tearing a 23 year old up and When I was 27 was knocking off a 33 year old.
7 years was the max. Now that I'm approaching 50, I go backwards never forward. Broads now are aged, fatted out and not pleasant to be around.
 
When I was 28 I smashed a coworker who was 52. She kind of reminded me of a younger version of Weezy Jefferson. RAW no pullout and it was good too. I was smashing it on and off for about 2 years.
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What you know about the old Court Street in Jacksonville :yes: We use to driver from Cherry Point to hang out with the hoes on the weekends.
I had friends from nyc and nj, we got a 96 every 3 weeks, I had they only car at time, we stayed makin the trips

only went to cherry point once
 
When I was 20-21, we catered a corporate event and a chick in her early 40s who worked there invited me back to her crib. She was definitely a good looking woman.
When I get there, I noticed she had a framed pic of her and Bobby Brown on her nightstand. They looked 'comfortable' enough to know that he was smashing. Not like I gave a fuck. Sex was fire.

Years later, I seen her in a bit role in Something's Gotta Give starring Jack Nicholson. He's talking to the dog on the street and she's like, "Awww. I wish somebody looked at me like that."

Edit: It wasn't Something's Gotta Give, it was As Good As it Gets. This is the scene:

 
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Probably biggest age gap 22 yrs.. I was 18 she was 40.. German summer school teacher.. she was married.. use to give me $20 everyday for lunch.. great tits, dick pleasing mouth.. fun summer… oldest chick, had a few 50+ yr old slob the knob… I would have older and even bigger age gap when I was younger but me and my fucking morals stop me from having sex or receiving head from people mothers, aunts, wives, sisters, etc that I knew.. yeah fucking morals have cockblocked me heavily through life
 
When I was 20 years old I smash a Nigerian movie was 10 years older than me.
 
i was 21-22 she was 35 plus. Fine lil dark skinned slimmie with a bubble. Her and her husband was seperated with two kids. She didn't work and stayed in some actually laid back clean and quiet projects lol. Used to call me twice a week to come over at lunch time to keep them plumbing pipes flowing good....lol. We fucked off and on for 3 years. Bea few months she'd stop by the job and see me and the next day we cutting. Real cool and never had any drama.
 
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