I Have Had Sex With Older Women

Personal Stories, Advice, and Support 409 People

    I was 35, she was 50.

    She was very hot, I was very surprised when we met in person, after teasing each other sexually for months. We went to her place, it didn't take but walking in the front door and she was all over me! I love how an older woman just takes control, as she had me naked in a...
    swndman swndman
    41-45, M
    1 Response Feb 16, 2016

    About 1 year ago I was at a party with my friend

    and we saw this really pretty lady she was 30 and I was ony 17 she was pretty drunk and I started talking to her she told me off at first but I eventually convinced her to talk to me as the party went on I actually got with her and ended up going to her place I was super nervous...
    boristhegreat99965 boristhegreat99965
    18-21, M
    Nov 10, 2015

    The first time I had sex with an older woman I

    was 24. She was 33 and we had fallen in love when we met at University. It was great, one time we got so excited that we fainted, me first. Now that may not sound funny to some of you, but we loved it. The second time I was 41, my partner was 50. It's amazing how passion makes...
    Legsandfaints Legsandfaints
    56-60, M
    1 Response Nov 17, 2015

    So I have done with this many older women.

    It used to be a super fantasy but I am the kinda guy that hates to want something and loves making his dreams come True. So I have made every dream I have ever had come true. But now I am finally thinking I may be able to make my dream of of my dream older mature (now elderly...
    zbigbox zbigbox
    31-35, M
    4 Responses Aug 4, 2015

    I love being with old(er) ladies.

    See comments and other posts for more.
    zbigbox zbigbox
    31-35, M
    2 Responses Dec 10, 2014

    Me and my mom had sex

    and after that I can't go back
    carsonswagg carsonswagg
    22-25, M
    5 Responses May 11, 2015

    A few weeks ago I went to my grandmothers home

    (she's 63) and after a few hours she started rubbing my leg then moved up to my crotch then got on her knees and later we had s**. I wonder what will happen the next time I go over there. Haven't talked to her since.
    1Thatonedudeyouknow 1Thatonedudeyouknow
    26-30, M
    1 Response Apr 29, 2015

    Mature women are the best .

    .... i so want to meet more in the uk ....
    spyonmum spyonmum
    18-21, M
    5 Responses Jan 4, 2016

    Hello :) im a young man

    who has been experimenting with things and i started to try anal and i have found i like it! I would love to have my fist anal experience with a tranny or sex with woman older than me :) if you are interested please msg me!
    6incheshappy 6incheshappy
    18-21, M
    Dec 7, 2015

    I have had sex with 2 friends mom's

    and one of my mom's friends.
    KansanTrucker KansanTrucker
    22-25, M
    3 Responses Oct 12, 2015

    This is me going up the backdoor of a super

    horny busty (36 D, see other posts did pics) Asian Granny masseuse. She was so amazing literally screaming at me to do it harder and faster while showing me pics of her 20 years younger bf. Lol. Plus her bf knows and encourages her to sleep with clients. (It's legal here). She...
    zbigbox zbigbox
    31-35, M
    2 Responses Jun 12, 2015

    Oh man this masseuse was the best ever.

    Met her today. She was the only one who listed her age on the list and it was 55. Plus she could take back door. But the best part was she could speak a little English and kept saying something really hot. Read comments for more. And look at the curves!
    zbigbox zbigbox
    31-35, M
    3 Responses Jun 12, 2015

    I was about to turn 30

    and she was 45. Met at a hotel by her work and....
    mkoopz16 mkoopz16
    26-30, M
    2 Responses Mar 15, 2016

    It was my teacher....

    Sometimes my **** gets on the wrong side of my boxers and i shift them often(it happens!). Well one time, I shifted it during class (more like 8 times XD). My teacher eventually saw me, and asked was i ok. I said I was fine but she could tell I was a bit embarrassed (even...
    VintageNebula85 VintageNebula85
    16-17, M
    1 Response Feb 6, 2016
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