This experience may contain mature content, as flagged by the community.
Please click away if you do not want to see this content.
To report inappropriate content, please email us.

I Have Had Sex With An Older Woman

Personal Stories, Advice, and Support 276 People

    Sex With My Future Wife

    My first time happened in 2002 when i was 16 years old. Ever since i was a kid i was attracted to a friend of my parents, Renia. She was a gorgeous Black haired woman with a wonderful body, tight *** and great large breasts. As i grew up i started to feel even more attracted to...
    thomaswayne thomaswayne
    26-30, M
    Feb 22, 2012

    Teenage Years

    I was 17 and she was a 47 year old tutor. She was going to be getting divorced and was the most beautiful, energetic, mature woman I have ever known. Sex with an older woman is the best feeling in the world. Someone who is actually mature, confident, independant, and secure. Wish...
    deleted deleted
    26-30
    1 Response Oct 26, 2012

    My First Older Woman

    The first time I had a sexual encounter with an older woman was during my senior year of college. I had been chatting online with a divorced woman, she was 45, and I was 22. One night after she was out in the city with her friends, she decided to come pick me up outside my dorm...
    FunGuy95 FunGuy95
    26-30, M
    Mar 12, 2013

    Panic Not

    Our the last few weeks I have been having amazing sex with a woman old enough to be my mum, I'm 18 and she's 50, fantastic body, so hot and horny with great legs, she wears stockings and sexy silky underwear, she's actually my mum's friend and I've known B since I was 10. I...
    MARLOR MARLOR
    22-25, M
    3 Responses Jan 16, 2012

    Sex With My Neighbor

    A few years ago, my long-time girlfriend dropped me for another guy. It just broke my heart. I drove home from work all depressed on a Friday night. I trudged the long walk from the parking lot to my apartment. I heard a voice from the balcony above my apartment. it was Judy, my...
    siddfinch siddfinch
    18-21, M
    1 Response Mar 30, 2013

    I Am A Cougar Victim :)

    I have worked at a hotel for many years in the centre of a major city and I have found that a few after a night out in the city they turn to me to complete there evening off in style. I am 33 years old man and know how to talk to a woman face to face to turn them on. I have...
    deleted deleted
    26-30
    Feb 13, 2013

    Ex-co-worker And Good Friend.

    I had been friends with this woman for a few years, we had been co-works for about a year and a half, and had always known she was interested in me despite the fact she was 13 years older than me, but I wanted to only remain friends, and at the time we were working together I was...
    bbwlvr bbwlvr
    26-30, M
    Oct 26, 2011

    Date An Older Women Is Date A Queen,How To Date An Older Women ??

    No age gap is too wide if you both feel so right. Love is ageless and pure. Hence, having a big age gap in a relationship should never pose a problem Still struggling to find Mature Dating website ? --== AgeMeet. C'om ==-- Best Cougar dating site in the world! For Cougars...
    caracc11 caracc11
    31-35, F
    Jun 25, 2013

    Life Teacher

    Her name was Sue and she was 40, I was 27. She was divorced and an amazing person. I learnt a lot about life from her not to mention a lot about sex. The main thing I remember about her was that the sex we had was just so damned good...we were really in sync. She loved to suck me...
    pv166 pv166
    46-50, M
    Aug 12, 2010

    Sex With My Future Wife

    My first time happened in 2002 when i was 16 years old. Ever since i was a kid i was attracted to a friend of my parents, Renia. She was a gorgeous Black haired woman with a wonderful body, tight *** and great large breasts. As i grew up i started to feel even more attracted to...
    thomaswayne thomaswayne
    26-30, M
    Feb 22, 2012

    Seduced By A Classmate

    During my junior year of college I met a single mom who was in her early thirties. She was recently divorced and her kids were teenagers who had lots of after school activities. Her name was Cassie and she stood at about five foot four inches tall. She usually would wear jeans...
    deleted deleted
    26-30
    2 Responses Aug 3, 2012

    My ex-wife is 8 years older

    than me. I honestly loved having sex with her.
    Kenneth184 Kenneth184
    41-45, M
    May 26, 2015

    All The Time

    I guess I'll break the ice. I'm married to an older woman. I'm 48 & my wife is 62, & the 16 years we've been together, (15 years married), have been the best years of my life, especially in the bedroom. Part of it is the fact that we're both pretty open sexually, (at least in...
    smallmark smallmark
    41-45, M
    4 Responses Mar 24, 2010

    20-40

    I was 20 she was 40. At the time she seemed like old woman to me. But now I am 40 and it does not look so old to me.She is now 60. I don't think I'd like to repeat what happened 20 years ago with her now. But I'd like girl of 20 just as she wanted boy of 20,
    kuca kuca
    41-45, M
    3 Responses Jul 12, 2010

    Finally Had Sex With Mom's Classy Friend

    I started when I was a teenager ************ in front of my mom's very sexy friend. She lived across the street and would dress in lingerie and read naughty extracts from Nicci Greene novels for me. I was surprised that a pretty lady like her was single but in a way I was glad...
    onelostboy onelostboy
    22-25, M
    4 Responses Jan 12, 2012

    My Little Sisters Friends Mom.

    My little sisters friend was having a party and her mom was chaperoning it. when all the little ones finished getting drunk and passing out me and the Mom started watching **** and smoking a joint. Next thing I knew she was ripping hers and mine clothes off and jumping top of me...
    AustinButtMan AustinButtMan
    41-45, M
    1 Response Feb 28, 2013

    Sex With

    i get attracted soon to long hair women tough they are young or old. Once i say a long hair lady having thick and long hair braid upto her hips it was moving like a pendulam when she was walking she was in a super market and i was at the back of her wherever she went on the...
    zakhm zakhm
    46-50
    Feb 23, 2013

    When I Was 21

    excuse me for my bad english :) Last year, I was 21, I had sex with a woman of 42. I was still a student and during the week I lived in a room that had a view at a house with a chubby wife and 2 daughters aged 5 and 7. The first contact came through the daughters whom I played...
    Ilium Ilium
    26-30, M
    1 Response Mar 20, 2013

    Sex With Paid Older Woman!

    I had a friend who has a contact of a lady who use to be "milf" earlier and now she charges for a shot!. I ****** her in her friend apartment. Do u think paid sex is weird or less interesting?
    coolniss coolniss
    22-25, M
    Feb 13, 2013

    I Was 18 She Was 40 And I've Been Hooked On Older Women Since

    I had met her on the train from Barcelona to Madrid while on my solo backpacking tour through Europe. She was blonde, thin, a bit ditzy for her age and very beautiful. She wore a long summer dress with a high slit at the front, her legs were long and tanned and I couldn't stop...
    pepper1989 pepper1989
    26-30, M
    Sep 26, 2013

    Hotel Meeting

    I had been chatting with a cougar online for awhile and we finally decided on meeting. She was 48, and I had just turned 30. She lived about an hour away, and still had kids at home, so we decided on getting together at a nearby hotel. We first decided to meet up at a bar right...
    FunGuy95 FunGuy95
    26-30, M
    Nov 17, 2013

    Hot Puertorican

    I was stationed in honduras and i met this beautiful puertorican Staff Sargent in the Army she was in her 40s but looked like she wasin her 20s she was very fun but fought me for a few days saying i was too young but i finally slept with her it was amazing she had a tight lil...
    curiousoneb curiousoneb
    22-25, M
    Oct 10, 2012
More Stories