Chat How old was the oldest woman you fucked? Civie, spa girl, wife, girlfriend, escort, or otherwise?

so i went to go look at a spa ad and they posted Tokyo-rose's pic as if it was a selling feature.

fuck god. don't look at that sober.
 
Come on buddy. She’s the perfect ticket. I’ll bet she’ll drop to knees in a flash if push the conversation. Sounds like a perfect FWB
Oh no buddy she was a mental case... Hot milf yes, but mentally unstable. She used to be a named lawyer so she had her own money too, although the story was her divorce settlement put her into high 7 figures. But the drinking and probably drugs made her a mess... matter of fact I didn't know back then, but when I grew up I figured she was probably high when we smashed cause she was acting very emotional the whole ride.
 
Oh no buddy she was a mental case... Hot milf yes, but mentally unstable. She used to be a named lawyer so she had her own money too, although the story was her divorce settlement put her into high 7 figures. But the drinking and probably drugs made her a mess... matter of fact I didn't know back then, but when I grew up I figured she was probably high when we smashed cause she was acting very emotional the whole ride.
Sounds like my kind of crazy. Lol
 
My first oldest woman was Apple at parkway forest it was in late 90’s. She’s at lease 40 at that time, body no complaints but you can’t look at her face tbh. Her bush is like steel wool, that I’ve neva encounter b4. I think she is still active this day, using the same old pix in her ad on redzone
Steel wool? Ha ha ha ha.
 
Haha! If that’s who I think, ie blond chick who would’ve been a knockout when younger, she hasn’t been 60ish in a couple of decades. Oldest I’ve had a go at was over 80. Kept herself immaculate. EE in another city many years ago.
That's gotta be a record. Do you know if she's still around? You could very well be the last guy she had sex with.
 
My first oldest woman was Apple at parkway forest it was in late 90’s. She’s at lease 40 at that time, body no complaints but you can’t look at her face tbh. Her bush is like steel wool, that I’ve neva encounter b4. I think she is still active this day, using the same old pix in her ad on redzone
Is she the Asian sp that goes by the Ai now? She use to be called Apple. She’s still going strong in an apartment behind Fairview mall. Huge tits, Hot body, great massage but ya the face isn’t to pretty. Lol. The steel wool was shaved off when I saw a couple years ago
 
Is she the Asian sp that goes by the Ai now? She use to be called Apple. She’s still going strong in an apartment behind Fairview mall. Huge tits, Hot body, great massage but ya the face isn’t to pretty. Lol. The steel wool was shaved off when I saw a couple years ago
That will be her, You are a brave man😅
 
Just after my 31st birthday the small tech company I worked for was sold. I got a generous 1 year’s pay as severance and headed to Europe for 6 months. Hit it off with the Dutch lady that owned the long term rental place. Had the wildest sex of my life…she initiated it all including anal. She loved the control she had over me. I thought she was in her fifties, but she told me she just turned 62. That’s a 31 year difference!!! Still the wildest I’ve every had…
 
I think I got a BJ from an Asian woman in her 50s back when I was in my 20s around 2005-ish, found a backpage ads that answered my call close to or past midnight. She was ugly but I was young and horny; I don't remember if I ever got off.

Somewhat recently a SP I saw a few times told me when we hung out that she is close to 50, I figured she was 40ish but she looked good for her age and her body was still pretty tight. She also gave me pretty amazing rimjob.

Some of the best sexes I had are usually from women in the 30s; too tight and the sex doesn't last that long and too loose doesn't have much feeling.
 
You got me beat for age difference, but I got you beat for the Woman's age, 73.
There are some really hot ones out there!

She had the hottest body but her face obviously looked old. She could probably pass for 50s.

Paid for a hotel, grabbed some wine and we spent the night together chatting and messing around. She definitely had many life (and sex) experiences.
 
I think I got a BJ from an Asian woman in her 50s back when I was in my 20s around 2005-ish, found a backpage ads that answered my call close to or past midnight. She was ugly but I was young and horny; I don't remember if I ever got off.

Somewhat recently a SP I saw a few times told me when we hung out that she is close to 50, I figured she was 40ish but she looked good for her age and her body was still pretty tight. She also gave me pretty amazing rimjob.

Some of the best sexes I had are usually from women in the 30s; too tight and the sex doesn't last that long and too loose doesn't have much feeling.
It just goes to show, you can't judge a book by it's cover. When I was in my 30's I met an early 50's woman who looked really hot, with beautiful natural breasts. Her pussy was so loose, I couldn't feel much. I had to keep checking to see if I was in her. I feel really bad for her, but I didn't say anything, as I didn't want to embarrass her.

Then after that, I met some women in mid 60's and older, whose pussies felt really good and tight. So, you'll never know what to expect.
 
I was 17 and she was 41, but told me she was 35. She owned a clothing store in what was Morningside Mall. I would go to the library everyday after school to use the computers before heading home. Her store was right beside the the library inside the mall and was always standing outside of it. She had a fat ass and always wore tight fitted clothing to show it off, I’d smile at her as I passed and sometimes she’d smile back. After months of this she, one day she initiated a convo and asked what year I was in in school. I respond with 4th as I was in grade 12, but I think she took it as I was a senior in Uni. I did look older than 17, had facial hair and was able to buy cigarettes without a problem. One day she asked me as I was leaving the library if I could help her move some boxes around in the back and I said sure. We got to the back which was very small and cramped, she bent over to pick up and box and grinded her ass on me, she did this a couple more times and I got a raging boner and she felt it, she turned around and thanked me for helping her and I left. Couple days later I went back and asked if she needed anymore help and she said sure, we go to the back and she does that same thing but is more obvious about it, I grabbed her waist and dry humped her a bit, we ended up making up and she gave me a HJ. This went on for a few months, til this day she’s been the best BJ I’ve ever gotten. It broke off when she found out I was 17 and a senior in high school, and thats when I realized she was 41 because she said she 24 years older than me. Oh well
Sounds like it was good while it lasted. I would have said, "so what? We did it a few times already. Why not keep going?"
 
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What does it feel like to have sex with someone in their 70's anyways?
Are you talking about me?
You can ask Cecilia and Yo yo for that answer ... 😅 😅 😅
 
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