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I Had Crossdresser Sex With An Older Man

Personal Stories, Advice, and Support 112 People

    Dressed For Older

    I am a slim 40 year old guy. I love to crossdress. One day I had just had a shower shaved my legs put on red nail varnish on my toes and fingers. I applied red lipstick and did my eye make up. I then dressed in red stockings skimpy red maids out fit heels and blond wig. It looked...
    dfsmaid dfsmaid 41-45 Nov 21, 2012

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    Crossdressers Love Older Men In Bed

    Last night I got off work late last night and decided to take a walk to wind down.  I picked a nice yellow thong with little butterflies on it.  Put on a unixex pair of runnning pants.  They end mid calf with a nice flair at the bottom.  Tight on the rear...
    talltabatha talltabatha 46-50, T 8 Responses Mar 24, 2010

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    More Fun

    My dilema was this. I was not sissy or fem and did not consider myself gay but would admit to being very bisexual so why had I enjoyed being dressed up in undies for a group of dirty old men. The answer became obvious. I was constantly horny the act of dressing up was a...
    lustbothways lustbothways 51-55, M 2 Responses Feb 16, 2011

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    My First Sex With An Older Man When I Started Crossdressing At Age 14

    Hi Everyone: My first sexual experience was with an older man who was friends with my mom . After she caught me in her bra girdle slip stockings and heels admiring myself and with a huge erection in her girdle for the third time ,she was at least as confused as I was then she...
    tammyie11111 tammyie11111 46-50 2 Responses May 13, 2012

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    How I Lost My Cherry

    It was a warm Saturday afternoon and I was visiting an older man who lived three blocks from my house. I had gotten to know him because I had been his paper boy for a while. He knew that I liked to wear skirts and slips and dress up as a girl and would let me dress up whenever I...
    deleted deleted 26-30 3 Responses Mar 15, 2012

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    Not One But Four

    This happened to me when I was just turned 18. I had gone to one of my favourite gloryholes for some sex and was enjoying my **** being sucked when I noticed a new message written in tiny writing above my head. It said "we are two very dirty old men over 65 who want a young fit...
    lustbothways lustbothways 51-55, M 3 Responses Dec 23, 2010

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    I Like To Suck Mature Married Men

    Ever since my teens I have loved to wear my mother's highheels & hosiery & give ******** to dirty old married men. It started when a friend of my dads caught me in mums bedroom while I was trying on a pair of her strappy sandals. I was only 18 at the time while Ted was in his 50...
    Prettyheels Prettyheels 31-35 8 Responses Sep 8, 2013

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    He Was Kinky!

    I met a guy online and he was in his early 60s. He really wanted to meet up, but I was scared because he sent me a picture and his **** looked waaaaay to big! We chatted for a couple weeks and he sent me a cute looking maid outfit and matching panties and bra. Another package...
    ellebelle18 ellebelle18 18-21, T 7 Responses Sep 11, 2012

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    My First Time Part 3

    There was a wet spot on his briefs near the tip of his enlarged member ,i could smell his manly essence.I leaned forward and licked the wet spot. He moaned and before i knew it he pulled his briefs down and it popped out hitting my cheek it felt hot on my face. I pulled back...
    joannacdsyd joannacdsyd 31-35 3 Responses Mar 29, 2013

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    My First Time Part 2

    It was very odd and nerve racking but as Troy and i stood at the sink doing the dishes talking i calmed down Troy was in his 50s back then he was about 6 ft tall a little over weight black hair with specks of white hair ,he was a truck driver and had been a friend of my fathers...
    joannacdsyd joannacdsyd 31-35 3 Responses Mar 28, 2013

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    I Was His *****

    i arrived at his house in the early evening, dressed with male clothes over sexy red satinn an dlace lingerie.  He directed me to a spare bedroom where i changed out of my male clothes and slipped on a figure hugging red mini dress, red fishnet stockings and sky-scraper...
    roxiefox roxiefox 56-60, T 5 Responses Apr 12, 2010

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    Several Older Men Over The Years

    My first time having sex with an older man while crossdressed was high school with a teaching assistant. We got sexually entangled after just a week or so, with him ************ me and giving me oral to ****** while he lightly fingered my furry testicles and my tightly puckered...
    jhenry922 jhenry922 41-45 1 Response Feb 20, 2013

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    First Time

    I was 17 the first time,i had been cross dressing since i was 13 years old.He my first was an older guy a friend of the family.He told me later he knew i was cross dressing for a long time he noticed may panty line on many occasions How it happen,my parents were going thru a...
    joannacdsyd joannacdsyd 31-35 1 Response Feb 10, 2013

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    Related Experiences

    We met in a 3 month long nursing class & work together. He knew dad & came to His funeral. He surprisingly kissed me out of the blue at a bar after some drinks & told me about his...
    BlueEyes3182 BlueEyes3182 31-35, F 2 Responses Apr 1

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    That would be great specially if he about nine inches or so that feel great
    iluvlezgal2 iluvlezgal2 41-45, F 7 Responses Apr 3

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    My wife does a lot of teasing and denial but I have not got any for a long time
    bendoverman75 bendoverman75 36-40, M 1 Response Mar 28

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    Ladiesman93 Ladiesman93 22-25, M 6 days ago

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    There was no way that he could be 47. No way. I thought he was 35 or 37, maybe 38. He acted like he was close to my age but clearly he was at least 10 years older than me. But why...
    poinsettia poinsettia 22-25, F 2 Responses 2 days ago

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    Older Men Like Younger Women as they are more vibrant, spontaneous and full of life. A survey of 2000 adults showed that only one percent of women preferred a relationship with a...
    likeyoungerwomen likeyoungerwomen 31-35, F Mar 31

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    Older Men Like Younger Women as they are more vibrant, spontaneous and full of life. A survey of 2000 adults showed that only one percent of women preferred a relationship with a...
    likeyoungerwomen likeyoungerwomen 31-35, F Mar 31

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    I want to be disrespected and face fu*!ed hard by an older man.. Anything goes I'd like to share this experience with a man who wants to get me off Am I the only one that likes...
    Cravingcock Cravingcock 18-21, F 11 Responses Mar 28

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    AgeMeet.com, a website specifically designed for older man younger woman relationships and older woman younger man relationships. AgeMeet.com is the world's first, largest and most...
    lauracc13 lauracc13 26-30, F Mar 31

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    AgeMeet.com, a website specifically designed for older man younger woman relationships and older woman younger man relationships. AgeMeet.com is the world's first, largest and most...
    lauracc13 lauracc13 26-30, F Mar 31

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    I have feelings for my neighborhood who's a teacher and I have always liked older men. I know people thinks it's gross, he has a daughter only 3 years younger than me. I want to...
    BeatriceSeekingOlder BeatriceSeekingOlder 31-35, F 4 Responses Mar 26

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    AgeMeet.com, a website specifically designed for older man younger woman relationships and older woman younger man relationships. AgeMeet.com is the world's first, largest and most...
    fionacc12 fionacc12 26-30, F Mar 26

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    AgeMeet.com, a website specifically designed for older man younger woman relationships and older woman younger man relationships. AgeMeet.com is the world's first, largest and most...
    lauracc13 lauracc13 26-30, F Mar 31

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    AgeMeet.com, a website specifically designed for older man younger woman relationships and older woman younger man relationships. AgeMeet.com is the world's first, largest and most...
    lauracc13 lauracc13 26-30, F Mar 31

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    You really like the idea of mothering an older man? I guess it's just where I am coming from that makes the idea seem a little odd to me. Am curious though, what makes you feel...
    crazynam321 crazynam321 36-40, M a week ago

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    am 18yrs old both my parents deceased have a older sister 40ish,i have 2babies 1and3,my sis takes care of my babies I support them being a exotic dancer my brother inlaw joe was...
    ralphbruno ralphbruno 56-60, F 2 Responses 2 days ago

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    When I was sixteen I embarked on a 15 year fling with a man 20 years older. He took me home on the first night and just gave me oral. It rocked my world. A lot to be said for...
    36EGirl 36EGirl 31-35, F 11 Responses Apr 3

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    The firs time I ever had my experience with another women was a few years ago, with my husband. Loved it! Hoping it happens again. I been attracted to women since around the end...
    MrsGrisham MrsGrisham 22-25, F 2 Responses 2 days ago

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    I never planned to date an older man, but at first he lied to me about his age and he looks good also very fit, so I believed. I have not started to date him seriously jet, but it...
    ElusiveLady ElusiveLady 26-30, F 7 Responses Mar 24

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    Never had sex with a black woman but I want to.
    andykenny andykenny 26-30, M 1 Response Apr 9

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    Last night (or this morning rather), one of my Twitter followers sent me a DM. It was innocent at first, but one thing lead to another. I found out he lived only 20 minutes away...
    acidxxxfire acidxxxfire 18-21, F 2 Responses Mar 30

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    I had sex with my husband yesterday! Sad thing we are in the middle of divorcing one another! I was just so desperate for sex... That I asked him for mercy sex... Gosh I hope I...
    just2lovelee just2lovelee 41-45, F 2 Responses Apr 11

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    Okay so it's actually a little different. For some reason I can not figure out how to add my own experience if I can, but anyway... I had sex with my friends dad... I am a little...
    speaksoftandcarrybigstick speaksoftandcarrybigstick 16-17, F 2 Responses 4 days ago

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    My wife is a gorgeous, petite 60 year old who looks much younger. She has always been a but of a flirt and has had sex with a few men since marrying me. She thinks she is too old...
    Jimxmarried Jimxmarried 51-55, M 12 Responses Apr 7

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    I don't satisfy my wife sexuly so am going to let her have sex with other men
    Sportybhoy Sportybhoy 46-50, M 6 Responses Apr 7

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    Ever since this girl first walked into our school for the first time, I couldn't take my eyes off her, and I know I probably wasn't the only one gazing at her beauty. Through my...
    elugo123456789 elugo123456789 18-21, M Apr 7

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    I went to one of her fashion shows and I got invited backstage to meet her. When I got there I saw her she was wearing a bikini, anyway I said hi and she said hi back, I kept...
    Ladiesman93 Ladiesman93 22-25, M 2 Responses Apr 16

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    I can't stop thinking about a erotic encounter with another woman I am In a relationship with a man right now but I have these fantasies about women.
    Jenniferparis Jenniferparis 26-30, F 3 Responses Apr 5

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    See, this titles kind of misleading. I had "A" fight with my mum, "A" meaning one. Not the truth in my case, unfortunately. If you want to skip this next paragraph, it's just some...
    NTC123 NTC123 13-15, F 2 Responses 1 day ago

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    I am looking for girls to have sex with and it's terrible bc 1 I can't find a girl 2 I live in Cranston and 3 idk I'm at the right place lol
    DaveP13 DaveP13 18-21, M Mar 24

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    I think one complete the other one,cause when you have sex with love it should be the most amazing feeling ever.
    miserableamy miserableamy 16-17, F Mar 25

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    I like having sex with out pertection
    izac31 izac31 18-21, M Mar 31

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    I love sex without protection message me and I will tell you why(;
    Hellogoodbye85 Hellogoodbye85 18-21, F 33 Responses Mar 31

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    I've always wanted to have sex with BBWs. I want to explore the whole body of a woman who is 200+ lbs, and tongue her holes before going in her and pounding her like there's no...
    MoaXing MoaXing 16-17, M 3 Responses Apr 6

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    I had an affair with a son of a ***** Francesco Clementucci, I really felt in love with him, despite the terrible intimate part with him and knowing that he is almost married, I...
    anna1953 anna1953 56-60, F Apr 10

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    I want to hear stories and see pictures of people having sex with animals!
    Cameltoelove Cameltoelove 22-25, M 3 Responses Apr 15

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    I want to have sex with her she's 15 and has a great body
    comeatmebruh623 comeatmebruh623 26-30, M 1 Response Apr 15

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    Like I've said before. We've been married 6 years and it gets better and better. It's really heated up when we bring other women into the bedroom. I never thought I would enjoy...
    redhot1221 redhot1221 36-40, F 5 Responses 2 days ago

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