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 Had Sex With An Older Woman

Personal Stories, Advice, and Support 368 People

    Not all men and women have the same romantic

    needs in life. Some prefer the member of the opposite sex to be of the same age, some prefer individuals older to them, while some prefer those younger than them. The individual needs are often criticized strongly, often accepted open mindedly, but the problem lies with finding...
    janecc11 janecc11
    26-30, F
    Jul 21, 2014

    I LOVE OLDER WOMAN! The most recent one I met

    off Tinder. She was 38 had a skinny frame. No bu*t really, had to decent t*ts. I went over to her house the same time we started talking. We had a couple drinks and as the night went on we started cuddling. Once we we're cuddling, I started kissing on her neck. and feeling...
    itnm4711 itnm4711
    26-30, M
    May 30, 2015

    I made the very foolish mistake of mixing my

    work life and personal life about three years ago when a beautiful woman joined our team. She had long curly blond hair, crystal blue eyes, 5'5 with an hourglass body and a E cup. She was 44 and recently separated while I was 25 and becoming annoyed with girls that where around...
    deleted deleted
    26-30
    1 Response Feb 28, 2014

    She liked to see me **********,

    but I wouldn't say that that was the main thing we did. I looked at her face. It didn't have a lot of expression. I used to get horny when I kissed her feet when we had intercourse. I loved her, sometimes I loved her very much. Years later, I had an affair with a woman that...
    Nakedness8 Nakedness8
    41-45, M
    Jun 2, 2014

    Not all men and women have the same romantic

    needs in life. Some prefer the member of the opposite sex to be of the same age, some prefer individuals older to them, while some prefer those younger than them. The individual needs are often criticized strongly, often accepted open mindedly, but the problem lies with finding...
    janecc11 janecc11
    26-30, F
    Jul 21, 2014

    I am in my Twenties. I was traveling

    for work in a small town in Iowa. It was a Saturday night and was sitting at the bar sipping a beer. About 10:00 o'clock this couple in their late 40's come in and they sit down nest to me. The guy and me are talking about baseball, football, politics...... when out of the blue...
    selectivefun1000 selectivefun1000
    26-30, M
    1 Response Feb 7, 2016

    In My Bedroom

    My mum's friend is a classy lady, brown hair and brown eyes, with a great body and fantastic legs, she's so horny, she says her husband is boring and no good in bed, she's 50 and I'm 18, sex with her is out of this world.On Friday, after my parents had gone out for a drink at the...
    MARLOR MARLOR
    22-25, M
    1 Response Jan 15, 2012

    When i was 16 i had my first sexual experience

    with an older women. She was 56 at the time and my next door neighbour, I was locked out of my house one day after school and she came out to see if i was okay considering it was winter and it was cold. She offered me in for a coffee so i accepted. Once inside the warm house i...
    Joshcnry Joshcnry
    22-25, M
    Mar 14, 2014

    I was left stunned I had sex with what I

    thought was a much younger women I was 30 I thought she was around 22 years old. I am 6ft 4 and she was is about 5ft 5. I was chatting her up and she was giving back as good as she got. I think I can't believe I'm actually going to **** a younger women. So we had sex and...
    deleted deleted
    26-30
    Nov 5, 2014

    I'm having a Facebook account

    for years now, things got changed through the years. When Someone sends a friend request I accept when I'm sure I know that person. If I don't, I gently ask if he/she knows me and if I would have to know that person. Same thing happened with this 29 year old woman (I was 18 at...
    RideTheBike RideTheBike
    18-21, M
    Apr 20, 2015

    Doing Diana

    When I was in college, a friend of the family who was an ambulance attendant/paramedic did night shifts there as a first aid person because people did chemistry labs late and required someone qualified to be available. I would sometimes drop by to talk with him as it was usually...
    jhenry922 jhenry922
    41-45
    1 Response Jan 31, 2011

    Summer Of 1980.

    It was the summer between my junior/senior year of Highschool,and I was recovering from a bad motorcycle accident (3breaks in my left wrist,compound fracture of the left femur,busted up several teeth) needless to say being 17 yrs old I had some issues with all of this. Then...
    deleted deleted
    26-30
    Sep 18, 2012

    Older And Still Horny

    I've had a few women older than myself. Some of the best sex I've ever had. Lots of fun in bed.
    bro4xxxfun bro4xxxfun
    36-40, M
    Nov 1, 2012

    Chance Encounter Turned Into Ongoing Friend With Benefits

    I first met Kate (not her real name) at the gym. She was an older lady but was a fitness nut and gym rat, more so than most guys I know. Physically, she's in great shape: about 5'7", shoulder length blonde hair, thin and fit. It would not be out of line to say that most 30 yo...
    drunkat drunkat
    31-35, M
    1 Response Oct 11, 2013

    So basically I met an older woman

    when I was 26 and had just broken up with my first fiancée. She was 43 and going through a rough divorce. We started out as friends and (very quickly) progressed to friends with benefits. We were sleeping together for about a year and we agreed it would be a purely physical...
    EarthWalkerMan EarthWalkerMan
    31-35, M
    1 Response Apr 5, 2015

    I was staying with my auntie,

    when one day she said would I a bag of thing to her friend Mrs Smith,Mrs Smith was a lady in her 60's slim with short grey, I went to her house and knocked the door she came to the door wearing a flowery blouse and a skirt, come in she said I gave her the bag to which she said...
    Paula111 Paula111
    56-60, M
    1 Response May 11, 2014

    Hard To Forget...

    We had been friends for a few years. I had always had a crush on her, but age set us apart. She was 15 years older, and 52. I didn’t think she looked at me in _that_ way. As she later told me, she was 5’6” and 120 pounds. (As I later found out, she had very firm breasts...
    jay045 jay045
    22-25
    1 Response Apr 25, 2011

    Bar Room Milf

    One night I was hanging at a local pub I was about 24 at the time the pub crowd was always older. I was sitting at the bar and this nice looking milf sat next to me and asked me to hand over her the karoke book. She asked me arent you gonna sing? I replied said only if you let...
    Sloppymut84 Sloppymut84
    31-35, M
    1 Response Aug 9, 2013

    Yes And Loved It

    I had sex with a woman i was 17 yrs old and she was about 48 and her husband was there also watching great 3 some
    deleted deleted
    26-30
    3 Responses Sep 23, 2010

    I was 24. She was 28

    and divorced. I was a virgin. I had dated some attractive girls and we had long lingering kisses, but the women I had dated had values that dictated no sex before marriage. I wasn't the pushy type and I liked them for who they were rather than how they could please me. I...
    mightyfineguy mightyfineguy
    61-65, M
    Oct 20, 2015

    Hot In Hawaii ...

    It was the end of August and I had just finished a deployment with the military, my first one. I had just turned 20 yrs old and was heading home for some well deserved time off. My parents had split up many years earlier and while mom moved on dad hadn't really gotten back into...
    deleted deleted
    26-30
    Oct 31, 2012

    Worked With

    This woman who was 39 at the time, 2 kids, divorced and I was 25. We used to casually flirt in the hallway and sit with the same group at lunch. We all went out as a group around Xmas, to a local bar for drinks and food. It turned into a late night and turns out she hitched a...
    Goldmember69 Goldmember69
    41-45, M
    Sep 30, 2013

    Sex With An Older Women!

    When I was youger, 22 years old, I had great sex with a women aged 39 it was amazing we both really were shattered! She was a bbw and she came in my face while I was going down on her! I would love to be able to have this same experience again with older women!
    maidenuk72 maidenuk72
    36-40
    Jun 9, 2010

    25 Years Older

    I still hold those times close to my heart. Such a wonderful lover she was and a dear friend forever. We met online and decided to meet for a drink at a local bar,she was hesitant as our age was so far apart,what could we have in common. After a few drink we went back to her...
    nylonlover70 nylonlover70
    41-45, M
    1 Response Feb 15, 2013

    I Was A Little Too Young

    I was what you might call sexually precocious. I had already had sex with a couple of girls around my age by the time I turned 13. But, I wasn't ready for what would happen the summer of my 13th year. I used to cut lawns for extra money and I was fortunate to land a weekly job...
    Fogarty Fogarty
    51-55, M
    1 Response May 26, 2010
More Stories