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  1. #1

    Who is/was the oldest man you've had sex with?

    Or to phrase it better, biggest gap from your age?

    I'm 23, and all the people I've been with have been around my age cept one guy, who was in his early 40s. And call me crazy, it was the best sex I've ever had. We were technically a couple for a few months too. All my friends found it weird, but honestly, I very much enjoyed the love and affection.

    How bout you boys?

  2. #2
    loki81
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    Re: Who is/was the oldest man you've had sex with?

    the oldest guy I had sex with was a few months ago... I'm 29, he was 39.

    purely for sex, I don't pay much attention to age versus how the guy looks/what he's like... but I couldn't imagine having a serious relationship with someone much older than 35-36 (and not much younger than 25-26)

  3. #3
    Sex God
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    Re: Who is/was the oldest man you've had sex with?

    when i was 19 i hooked up with a 45 year old guy and his 49 year old partner. both of them had really nice cocks and knew how to use them

  4. #4

    Re: Who is/was the oldest man you've had sex with?

    ta make it hot ans get dudes real pumpin got make it long reply

    but short answer older then me

    thankyou

  5. #5
    huh?
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    Re: Who is/was the oldest man you've had sex with?

    Prolly my partner, he's 57....I'm 54
    FPNY
    Annoying JUBBERS since 2003

  6. #6
    On the Prowl SpartyHardy's Avatar
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    Re: Who is/was the oldest man you've had sex with?

    I'm 21, and...23

  7. #7
    A Total Bottom mbamike's Avatar
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    Re: Who is/was the oldest man you've had sex with?

    For the biggest gap from my age, I will need to go younger. I hooked up with a guy 15 years my junior several times.

    Homophobia kills!

  8. #8
    AWP82
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    Re: Who is/was the oldest man you've had sex with?

    27, when I was 25.

  9. #9
    The Baroness of Bling
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    Re: Who is/was the oldest man you've had sex with?

    Hum, barring the people whose ages I did not know (whose names I frequently did not know), the oldest man I've ever been with was 42, and I was 28. Before that I'd always dated people within two or three years of my own age; and that was also the last time I had sex, so I haven't had the opportunity to break that record.

    It strikes me as sad that I'm now older than he was, and I thought him awfully old at the time. I wonder if I have Old Man Smell down there, the way he did? Maybe it's time to find out... any volunteers?

    * Question the Dominant Paradigm *

  10. #10
    Wildly Inappropriate SonOfSlobone's Avatar
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    Re: Who is/was the oldest man you've had sex with?

    Hard to say when you're having anonymous group sex in a dark after-hours (way after) San Francisco sex club. Maybe 30 years?

  11. #11

    Re: Who is/was the oldest man you've had sex with?

    I've only ever had sex with one guy older than me ... he was one year older and we were in an l.t.r. for five years in our early 20s.

    The biggest age-gap was about 25 years younger than me when I was in my late 40s.


    It's a continuous frustration to me that, whilst I am most attracted to guys around my own age or slightly older, no gay man of my generation is ever remotely interested in me.

    Meanwhile, younger 'bi-curious' guys occasionally are attracted to me ... so I have to make do with them.

  12. #12
    meagain
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    Re: Who is/was the oldest man you've had sex with?

    I was 27 and he was around 45 I guess

  13. #13
    In Heat............ BENDERBOY's Avatar
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    Re: Who is/was the oldest man you've had sex with?

    47 when i was 19.

  14. #14
    The old familiar sting blackbeltninja's Avatar
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    Re: Who is/was the oldest man you've had sex with?

    All been around my age; the oldest was 5 years older at 39 back in May.

    -d-
    Members: [insert appropriate/relevant wise saying or deep thought here]
    Thank you.


    I hope you get this message.
    Comments welcome.

  15. #15

    Re: Who is/was the oldest man you've had sex with?

    I get crotch groped by a guy of 90 and I like it.

  16. #16
    MoePhoenix7
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    Re: Who is/was the oldest man you've had sex with?

    The oldest guy I've been with sexually was my current age (22) and I at the time was 20 (a month shy of turning 21).

    I'm not opposed to being with an older guy but I try not to get involved who aren't in or around the same age range as myself.

  17. #17

    Re: Who is/was the oldest man you've had sex with?

    I was 25 he was 55. I enjoyed it.

  18. #18
    Sex God blublud's Avatar
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    Re: Who is/was the oldest man you've had sex with?

    I was 46 years older than one boy. But, do rent boys count here?

  19. #19
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    Re: Who is/was the oldest man you've had sex with?

    50, and it's making my carpal tunnel syndrome worse...

  20. #20
    JP.
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    Re: Who is/was the oldest man you've had sex with?

    45 the good side is he's willing to do nasty degrading things..whatever I command.

    and one of the nicest dick I ever taste

  21. #21
    JUB Addict teadrinker's Avatar
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    Re: Who is/was the oldest man you've had sex with?

    I was 50 at the time and he was 63. Great guy, great kissing, great sex. If it wasn't for the fact that he lives a long way away I'd be all over him constantly.

    -T.

    "Thank God for tea! What would the world do without tea? how did it exist? I am glad I was not born before tea." (Sydney Smith)

  22. #22
    JUB Addict teadrinker's Avatar
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    Re: Who is/was the oldest man you've had sex with?

    I was 50 at the time and he was 63. Great guy, great kissing, great sex. If it wasn't for the fact that he lives a long way away I'd be all over him constantly.

    -T.

    "Thank God for tea! What would the world do without tea? how did it exist? I am glad I was not born before tea." (Sydney Smith)

  23. #23
    vvaamim
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    Re: Who is/was the oldest man you've had sex with?

    52. I was 18. It was ok. :/

  24. #24
    Slut
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    Re: Who is/was the oldest man you've had sex with?

    I'm 24, he was 29.

  25. #25
    Sex God WillMc88's Avatar
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    Re: Who is/was the oldest man you've had sex with?

    87... when I was 9.

  26. #26
    Love me or hate me. Eternaldarkness's Avatar
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    Re: Who is/was the oldest man you've had sex with?

    I was 22, he was 55... I don't know, never found him to be that old while I was hooking up with him. He's pretty fit, young body but older face.

    I don't know, but when you find yourself a really nice friend, the age doesn't seem to bother.


    Now, when I'm no longer with him and lost my passion and urge (I'm also with a younger guy than me) he does seem a lot older and I tend to notice it more. I find it odd how I notice his age and oldness more when we no longer hook up.

    Aim\Yahoo\Dlist\everything else: Sexyguy80808

  27. #27
    Acolyte of the flux
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    Re: Who is/was the oldest man you've had sex with?

    I was 26, he was 54.
    ."We are all in the gutter, but some of us are looking at the stars."
    (Oscar Wilde, Lady Windermere's Fan)

  28. #28
    Sex God Musik2400's Avatar
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    Re: Who is/was the oldest man you've had sex with?

    Biggest age gap was 11 years... and it was the worst sex in my life. I was 19, he was 30. He was.... clumsy to say the least. It was just... bad...

  29. #29
    On the Prowl
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    Re: Who is/was the oldest man you've had sex with?

    12 years difference. I'm 21 and he's 33. Marriage is in our future as we are in-love.

  30. #30
    Slut zunkian's Avatar
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    Re: Who is/was the oldest man you've had sex with?

    I've always liked hooking up with matured gentlemen. Aside from the great and most unforgettable sex, you get to be babied and loved 3x more!!!
    I was 24 when I had first sex with an older guy who was 45. Next was when was 28 and he was 62. Then as I entered into my 30's, all the guys I've hooked up with ranges from 50 to 70. Wonderful experiences of my life!

  31. #31
    Hatter
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    Re: Who is/was the oldest man you've had sex with?

    For love it was a 35yo when I was 18, for money it was a 70yo when I was 19.

    Always been attracted to men older than myself, and still, at 35 I'm seeing a 41yo.

  32. #32
    Inactive RonR18's Avatar
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    Re: Who is/was the oldest man you've had sex with?

    When I was 18 a cool guy seduced me who was 50-55, and I let him strip me and have his way with my butt after he sucked my dick. Butt after rimming my butt and trying to stick his big dick in my small butt hole, he had to settle for fucking me with just his finger. Anyway, it was an "eye-opening" experience for me, given that he was extremely skilled at rimming.


    "The surest way to make a monkey of a man is to quote him."
    ~ Robert Benchley

  33. #33
    Wuvable Oaf
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    Re: Who is/was the oldest man you've had sex with?

    I think it was when I was 19 or 20 (seems so longer ago), I think I remember his age was 63

  34. #34
    Vannie
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    Re: Who is/was the oldest man you've had sex with?

    I was 24 and he was 93....

    He took his teeth out

    He was like a Hoover with lips.....

  35. #35
    brs320
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    Re: Who is/was the oldest man you've had sex with?

    I gave a 52 year old a handjob once when I was 18, but the oldest person I've had sex with is 46

  36. #36
    Formulas Fatal to Flesh.
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    Re: Who is/was the oldest man you've had sex with?

    The oldest i've been with was 46, but I wouldn't find that out until later(I don't get guys that lie about their age).

  37. #37
    Huntneo(PT)
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    Re: Who is/was the oldest man you've had sex with?

    a 49-year-old who I will always remember as one of my best.

    he tore me up and made me his bitch.

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