Oldest Person You've Had Sex With

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

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  1. Downonthemuffin

    Downonthemuffin Members

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    A lifestyle playmate, I was 49 and she was 60
     
    Downonthemuffin, Dec 6, 2025
    #141
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  3. Woodyman1

    Woodyman1 Newbie

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    Thats very Hot, we're you 2 married at the time?
     
    Woodyman1, Dec 14, 2025
    #142
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  5. Woodyman1

    Woodyman1 Newbie

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    That's so hot
     
    Woodyman1, Dec 14, 2025
    #143
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  7. olderndirt

    olderndirt Senior Member

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    Yes. She had my permission to do it.
     
    olderndirt, Dec 15, 2025
    #144
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  9. Bobbie Anderson

    Bobbie Anderson Easy open

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    I am free use. I sucked off man 68 helped him get his nut out. He really enjoyed and I was glad I was able to please him.
     
    Bobbie Anderson, Dec 23, 2025
    #145
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  11. Joe90

    Joe90 Supporters HipForums Supporter

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    Things are looking up :blush:;):smilingimp:.
     
    Joe90, Dec 23, 2025
    #146
  13. Curiouscouple2469

    Curiouscouple2469 Members

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    Oldest would be mid 50’s just because I am now in my 60’s- however if talking widest age gap that’s different.

    When I was 18 my buddy and I were picked up at a bar (yes underage) by two cougars in their late 40 at least, taken home and balled senseless by them…. That was a night of education we wouldn’t soon forget…
     
    Curiouscouple2469, Dec 27, 2025
    #147
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  15. Bobbie Anderson

    Bobbie Anderson Easy open

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    She was 62 abd I was 21 at the time
     
    Bobbie Anderson, Jan 8, 2026 at 6:26 PM
    #148
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  17. Curiouscouple2469

    Curiouscouple2469 Members

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    The older gals get their way and you get a lesson from the experienced. Win win
     
    Curiouscouple2469, Jan 8, 2026 at 10:38 PM
    #149
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  19. Iscott55

    Iscott55 Enjoying life Lifetime Supporter

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    That’s hot!! You did your community service
     
    Iscott55, Jan 9, 2026 at 5:33 PM
    #150
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