Biggest Age Difference

Tell the story pleaze
The story is, I met him on a daddy site. He was really nice. I slept at his house for a few months. Nothing sexual besides he made walk around naked all day. He paid for everything even bought me a car.

Then I saw his cock age didn't matter. Biggest cock I've ever had. Old white guy 13 inch cock and could use it with pills.
 
I was 27-29. She was 68-70. She was a retired Executive Assistant that I met on Yahoo Personals back in the early 2000s. We messed around for several years. Her health started to fade and when her ******* moved in to take care of her we stopped seeing each other. She's no longer with us but I still remember her very fondly.

She was my first
- over 40yo
- over 10 years age difference
- threesome
- squirter
- grandmother
- pool sex
- and probably a few more I can't recall

Screenshot_20210112-095650_Drive.jpg
 
I was 27-29. She was 68-70. She was a retired Executive Assistant that I met on Yahoo Personals back in the early 2000s. We messed around for several years. Her health started to fade and when her ******* moved in to take care of her we stopped seeing each other. She's no longer with us but I still remember her very fondly.

She was my first
- over 40yo
- over 10 years age difference
- threesome
- squirter
- grandmother
- pool sex
- and probably a few more I can't recall

View attachment 3847687
Wish l had known her!!
 
When my wife was 52 she had a 30 year old boyfriend who fucked her regularly. He was Hispanic and our house was in between his apartment and his job. He worked a lot of overtime and he'd sleep over at our house after a long shift and before another so he could satisfy himself with my wife. I treated him like a house guest and he even had his own room to sleep in when he wasn't fucking her.
Before I retired I met a 22 year old woman at work that took an obsessive interest in me. One day in my office I told her, "I don't have affairs", she sat on the corner of my desk and hiked her skirt up and showed me her shaved little pussy and asked, "can't we just fuck?".
I was 52 and sterile from a vasectomy. The first time I fucked her in my office after hours she was bent over my desk when I shot in her pussy. She was immediately upset and told me she wasn't on the pill. She didn't understand that with a vasectomy I still had cum, but no sperm in it.
She had several failed pregnancies and was afraid to try again so she wouldn't let her husband cum inside her. After learning my cum had no sperm she spent her time at work walking around dripping my load into her panties as much as we could manage.
She began allowing her husband to take naked and sexual pictures of her so she could secretly send them to me. She sent me pictures of him eating her pussy in the same clothes she had worn to work, so I knew he was eating my load out of her.
 

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Last edited:
I was 27-29. She was 68-70. She was a retired Executive Assistant that I met on Yahoo Personals back in the early 2000s. We messed around for several years. Her health started to fade and when her ******* moved in to take care of her we stopped seeing each other. She's no longer with us but I still remember her very fondly.

She was my first
- over 40yo
- over 10 years age difference
- threesome
- squirter
- grandmother
- pool sex
- and probably a few more I can't recall

View attachment 3847687
I still regret not taking more advantage of the Yahoo personals back in the day. I wasted my time messing around in the groups. At one point I think I was a member of over 100 groups. Nice job! RIP.
 
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