Oldest Person You've Had Sex With

Discussion in 'Free Love' started by Barry Mandelay, Jun 20, 2021.

  1. tjr1964

    tjr1964 Members

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    Luckily, this 31 year old divorcee, shown me everything I needed to know about how to please a woman ....it was 3 days before my 17th birthday.
    I had only two girls before her and they claimed I was too long and too fat ( penis wise ) . I tend to stretch out vaginas and hit the back wall of women's cervixes .
    So when I had sex with girls my age, I was a mind blowing experience.
    That divorcee was such a sweet patient woman .
     
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  2. The Shark

    The Shark Members

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    My wife. Every time we have sex, she continues to be the oldest person I’ve had sex with. So I proudly get to say that I have sex on a regular basis with a beautiful MILF.
     
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  3. Paddington2023

    Paddington2023 Members

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    I was out with my cousins and we ended up going back to an older lady that they knew.

    I slept downstairs and they shared a bed upstairs.

    I was 19 and the friend would have been in her 60’s.

    Through the night I woke up to her sucking on my cock. She then mounted me and fucked me stupid.

    The next morning she carried on as if nothing happened when my cousins came down.

    Turns out her husband had left her a few weeks before and she went off the rails a bit for the first few months. I was one of many young lads that she fucked before moving away.
     
  4. Allenr35

    Allenr35 Newbie

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    Wow....80...I hope I'm fucking at that age
     
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  5. You me and coffee

    You me and coffee Members

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    My husband…66.
     
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  6. jball45

    jball45 :P

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    He was sixty
     
  7. KDaddy23

    KDaddy23 Lifetime Supporter Lifetime Supporter

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    Well, that would be my lady, who's 71... and baby still got it!

    Now, when I was 17 and days before I was to leave for USAF basic training, my boys - or my so-called boys - set me up with a woman to get me laid (and like I needed their help!). They ushered me blindfolded into a really dark room and the jerks left me there until I felt a hand grab mine and pull me onto a bed...

    Where a lady who had to be in her late 50s wore my ass out and further took me to school about eating pussy to a woman's satisfaction. I was with her for three days having all kinds of sex with her and, I guess my so-called friends got worried because they came looking for me.

    Probably the best three days of my life at that point. As I was leaving with my boys, she pulled me into a deep kiss and said, "Remember: If she's not looking at you like you tried to kill her by eating her pussy, you didn't do it right - so never make me look bad!"
     
    Last edited: Dec 24, 2023
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  8. Cprailone

    Cprailone Members

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    My love is 68 and getting
    sexier and hornier every day.
     
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  9. FriendlyCock

    FriendlyCock Members

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    I was 50, she was 60, single with a boyfriend. She was hot to play, and had a big red hairy vag, and loved me licking her out. Condoms were the rule. Less feel but lasted longer. It was nice to see my cock disappearing between her red slit and bunch of pubes. It didn't last. Mind games. I had a 69 year old guy who sucked me off quite a bit when I was 50. Much easier, no mind games.
     
  10. Andy Schumer

    Andy Schumer Visitor

    Myself being mid 50’s, someone 61
    Just one encounter, she was not into me
     
  11. Transguy

    Transguy Lifetime Supporter Lifetime Supporter

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    I was 23 and he was 44
     
  12. suolsu

    suolsu DM me!

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    If I remember correctly, he was 56.
     
  13. Jello2053

    Jello2053 Members

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    My wife at 71, I’m 70. She mostly sees men over 50.
     
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  14. late_bloomer

    late_bloomer Senior Member

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    She's seeing other men?
     
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  15. Jello2053

    Jello2053 Members

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    Yes but age is catching up to us and friends
     
  16. straightma1e

    straightma1e Members

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    Ain't that a bitch! Getting older always fucks things up. Then you die.
     
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  17. Jello2053

    Jello2053 Members

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    We still play, just not as often. She has one “special” friend and now just cuddle. I have one cuddle buddy my age but two friends 20 years younger that I see only two-three times a year
     
  18. straightma1e

    straightma1e Members

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    Are you still going strong? I am at 72. But my FB who moved away a few years ago was 62 the last time we got together. She was a damn good fuck too. Now all I have to tap are women some 20 years or more younger. Hopefully I'll continue to tap women that age and younger for as many years as this old body will let me.
     
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  19. Jello2053

    Jello2053 Members

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    Not as strong but still active
     
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  20. Jacob1994

    Jacob1994 Members

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    So far 58, which is almost double my age now.
     
  21. Andy Schumer

    Andy Schumer Visitor

    Care to tell a little more about it? :)
     
    suolsu likes this.

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