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Age gap between the oldest/younger chick you plowed?

Oldest Age Gap: when I was 21 I picked up a 36 year old
Youngest Age Gap: when I was 53 I was dating a 27 yr old

You didn't ask me for pics, and most of her pictures I probably wouldn't share but this is the 27 yr old. Those boobs are real, and real nice. She does Yoga and was a gymnast so the sex options were almost endless. 114 lb bundle of fun & energy. Built for speed.


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A year or so before I got married I met a black chick named Rani (pronounced Ronnie) out at a place called Deck on Dragon in Dallas (unfortunately, it wasn’t a dungeons and dragons place 🙁 ). I was 36 and I knew she was younger but was thinking mid late 20’s. We fooled around for for most of the summer and then one day she goes, “welp, I gotta go back to school. It’s been fun.” I was think, ok grad school or internship or something. But nope, had a year left of undergrad. Just turned 21. @BIG TONE SOPRANO seent it.
 
A year or so before I got married I met a black chick named Rani (pronounced Ronnie) out at a place called Deck on Dragon in Dallas (unfortunately, it wasn’t a dungeons and dragons place 🙁 ). I was 36 and I knew she was younger but was thinking mid late 20’s. We fooled around for for most of the summer and then one day she goes, “welp, I gotta go back to school. It’s been fun.” I was think, ok grad school or internship or something. But nope, had a year left of undergrad. Just turned 21. @BIG TONE SOPRANO seent it.

If she pronounced her name correctly it would mean “Queen” in Hindi.


Instead she went with a nickname for “Ron/Ronald.”


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A year or so before I got married I met a black chick named Rani (pronounced Ronnie) out at a place called Deck on Dragon in Dallas (unfortunately, it wasn’t a dungeons and dragons place 🙁 ). I was 36 and I knew she was younger but was thinking mid late 20’s. We fooled around for for most of the summer and then one day she goes, “welp, I gotta go back to school. It’s been fun.” I was think, ok grad school or internship or something. But nope, had a year left of undergrad. Just turned 21. @BIG TONE SOPRANO seent it.
Brother Lee. Thank your lucky stars it wasn't high school.
 
Chiming in for @#HBD on this one.

We were just graduated from college, probably 22-23 y/o. One of our buddy's friend's mom was in town for a game in Lincoln and one thing lead to another and they wound up tossing it around in @BIG TONE SOPRANO bed. She had to be mid-late 40's and let's just say didn't fit into the milf category. Not sure what got into our boy, but he could NOT resist her charms. She looked almost exactly like Mimi from the Drew Carey show, only just slightly less attractive:

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A year or so before I got married I met a black chick named Rani (pronounced Ronnie) out at a place called Deck on Dragon in Dallas (unfortunately, it wasn’t a dungeons and dragons place 🙁 ). I was 36 and I knew she was younger but was thinking mid late 20’s. We fooled around for for most of the summer and then one day she goes, “welp, I gotta go back to school. It’s been fun.” I was think, ok grad school or internship or something. But nope, had a year left of undergrad. Just turned 21. @BIG TONE SOPRANO seent it.

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Direction 1
Me 24, her 38
When we met in a bar on vacation at Bass Lake, CA she said "my daughter would love you"
I went back to visit her for the labor day weekend. Her daughter was there with her BF too.

Direction 2
Me 57, her 37
Met her on my Bday at The Baked Potato jazz club near Universal.
A singer in her pretend life. Was fun for a couple of months. A crazy narcissistic cunt in her real life.
 
Fucked a 19 year old when I was 46 for a few months

Fucked a 41 year old when I was 27

Both were a hell of a lot of fun, with the advantage to the 19 year old even though I still feel a little dirty for that
Thanks for your service to these ladies, brother.
 

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