The oldest woman you have had sex with

I was 22. Happily married woman, 41. Had an almost every Thursday after work hook up. Many many times with her over 2 years. Hubby had no idea. She was the manager at my credit union. Dressed in business clothes usually skirt and blouse, modest heels. Classy haircut. Rock solid body.
I learned a LOT because of her. She loved to kiss while we had sex. Took it in her butt no problem. Swallowed no problem but didn't happen often, she was on the pill so we did it bare.
It happened to.me to.start by accident a ew people from work went for drinks the next time everyone left except her and I
That night it happened and contined about once monthshe was amazing she was 15 years older than me she taught me a few things itbwas the most intense fucki.g i have ever had
 
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The oldest woman I have fucked was 56 when I was 28, she was my supervisor and was divorced, at the time I worked at an assembly plant making automotive parts, she was my line supervisor and most of the time tended to be really hard on the team, we all knew there was a quota to meet but a lot of times she was still hard on us even if we completed everything,

All the team members used to say that she really needed to get fucked and calm down, some of the girls on the team that knew her said she'd been divorced a little over 15 years and hadn't had anyone since then, all that backed up energy had made her very hard to get along with,

I always liked older women and she was nice looking for her age, great body, legs, tits and ass, we all decided to invite her to one of our after work parties to see if she could unwind and calm herself down a bit, at first she didn't go but after a bit of asking she showed up at one of our parties, we immediately started getting her drinks and once she started relaxing I got her on the dance floor, it turned out to be a great night and she loved dancing with me, I started asking her out and eventually we started fucking, all that energy she had build up inside of her made for some amazing orgasms.
 
When I was 17, I got the chance to fuck one of my ex-girlfriend’s moms. She must’ve been 45 at the time not the oldest woman I’ve ever fucked but definitely the biggest age gap for sure. She definitely knew what she wanted and how to get it I was just a young sex toy for her. It was incredible
 
When I was 17, I got the chance to fuck one of my ex-girlfriend’s moms. She must’ve been 45 at the time not the oldest woman I’ve ever fucked but definitely the biggest age gap for sure. She definitely knew what she wanted and how to get it I was just a young sex toy for her. It was incredible
you are my hero. Summer of 1988. I was 20 and was given the opportunity to fuck an Italian/American milf of around 45. She made ALL the right moves but I was dumber than Sheldon Cooper. I will go to purgatory; not for what I did, but what I failed to do....
 
When I was 17, I got the chance to fuck one of my ex-girlfriend’s moms. She must’ve been 45 at the time not the oldest woman I’ve ever fucked but definitely the biggest age gap for sure. She definitely knew what she wanted and how to get it I was just a young sex toy for her. It was incredible
I can relate. I was 22 and fucking a happily married 41yo. Almost every Thursday after work for over a year.
 
When I was 17, I got the chance to fuck one of my ex-girlfriend’s moms. She must’ve been 45 at the time not the oldest woman I’ve ever fucked but definitely the biggest age gap for sure. She definitely knew what she wanted and how to get it I was just a young sex toy for her. It was incredible
I was 14 chasing a lady who was 29. When she finally conceded she was quite the teacher.
At 16 I was playing with a 34yr old in front of her boyfriend.
Older women were always my thing
 
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The oldest woman I have fucked was 56 when I was 28, she was my supervisor and was divorced, at the time I worked at an assembly plant making automotive parts, she was my line supervisor and most of the time tended to be really hard on the team, we all knew there was a quota to meet but a lot of times she was still hard on us even if we completed everything,

All the team members used to say that she really needed to get fucked and calm down, some of the girls on the team that knew her said she'd been divorced a little over 15 years and hadn't had anyone since then, all that backed up energy had made her very hard to get along with,

I always liked older women and she was nice looking for her age, great body, legs, tits and ass, we all decided to invite her to one of our after work parties to see if she could unwind and calm herself down a bit, at first she didn't go but after a bit of asking she showed up at one of our parties, we immediately started getting her drinks and once she started relaxing I got her on the dance floor, it turned out to be a great night and she loved dancing with me, I started asking her out and eventually we started fucking, all that energy she had build up inside of her made for some amazing orgasms.
I fucked a lady i worked with she was 15 years older thane i was 35 she taught me a thing or two one night we were really getting it on , she pushed me off iwas shocked she wasnt ready yet we started agaim i can honestly say was more than shocked but when.i entered her agaim it was i believeable she was amazing we fucked every week.or two for about 2 years
 
I fucked a lady i worked with she was 15 years older thane i was 35 she taught me a thing or two one night we were really getting it on , she pushed me off iwas shocked she wasnt ready yet we started agaim i can honestly say was more than shocked but when.i entered her agaim it was i believeable she was amazing we fucked every week.or two for about 2 years
Yeah for my lady friend once we started fucking it totally changed how she was at work, she wanted to keep our fucking a secret but people knew, it was great watching her go from a stuck up supervisor to a sex hungry woman, I was surprised how sexy she looked wearing dresses and heels when we would go out, sometimes she couldn't wait to get in bed and there were plenty of time we fucked in the car.
 
My 1st wife was only 6 yrs older than me. but I was a 21yr old virgin and she already had 1 kid and a solid resume. She was also a supervisor at my job. In Puerto Rico, they all wear high heels and miniskirts or dresses year round. Plus her caribbean ass drove me nuts.

Not only did she teach me the ropes, she groomed me into being a cuck right from the start. Everyone noticed how she was running circles around me, but I was loving it. She convinced me how it was OK for me to wait in her apartment while she had a sex date with her LT boyfriend and then came home and let me have her.