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I Had Crossdresser Sex With An Older Man

Personal Stories, Advice, and Support 115 People

    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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    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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    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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    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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    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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    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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    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 11 Responses Sep 8, 2013

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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 8 Responses May 13, 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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    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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    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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    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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    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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    Related Experiences

    I'm only 19 year old girl, but I would love to have a sexual relationship with a 40-55 year old women and do sexual things with her (or without her) with her teen-age kids (if she...
    Jamielr13 Jamielr13 18-21, F 5 Responses a week ago

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    At first I didn't know what to think. Then I decided that I was giving this man something his wife could not give him. Sexual satisfaction. I knew the mans wife because I was...
    deleted deleted 26-30 5 Responses Jul 29

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    would like to go further
    livingofgrid livingofgrid 56-60, M 3 Responses Jul 24

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    I've never had sex with a man, but lately I think about it all the time. I want to find another man my age also eager to have sex with a man for the first time.
    padraig412 padraig412 51-55, M 4 Responses Aug 6

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    It lasted for almost a decade. It ended four years ago. I've been typing and deleting what I typed. Haha! How can I describe it? It was chaos, bliss, addiction, nourishment, bane...
    REG821 REG821 41-45 1 Response a week ago

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    Younger Women Looking for Older Men is because Older Men are more confident and generally more wise and intelligent, qualities ,Older men know how treat a woman better than younger...
    SkyCC11 SkyCC11 26-30, F Jul 21

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    Younger Women Looking for Older Men is because Older Men are more confident and generally more wise and intelligent, qualities ,Older men know how treat a woman better than younger...
    SkyCC11 SkyCC11 26-30, F 2 Responses Jul 21

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    Younger Women Looking for Older Men is because Older Men are more confident and generally more wise and intelligent, qualities ,Older men know how treat a woman better than younger...
    SkyCC11 SkyCC11 26-30, F Jul 21

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    Younger Women Looking For Older Men is because Older Men are more confident and generally more wise and intelligent, qualities ,Older men know how treat a woman better than younger...
    SkyCC11 SkyCC11 26-30, F Jul 21

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    Younger Women Looking For Older Men is because Older Men are more confident and generally more wise and intelligent, qualities ,Older men know how treat a woman better than younger...
    SkyCC11 SkyCC11 26-30, F Jul 21

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    Younger Women Looking For Older Men is because Older Men are more confident and generally more wise and intelligent, qualities ,Older men know how treat a woman better than younger...
    SkyCC11 SkyCC11 26-30, F 2 Responses Jul 21

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    I am in love with my man who isn't too older than me. He's only 5 days older, but I only am into older guys.
    roselani2005 roselani2005 26-30, F 1 Response 3 days ago

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    This happened a while ago... I have been having this fantasy of seeing her with another man.. could never get it done... Have always used those visualizations during our love...
    stimulatingcouple stimulatingcouple 46-50, M 5 Responses Jul 27

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    I'm very much in love with a man 10 plus years older than myself. We have, what I'd like to think of as, a healthy relationship with open communication, warmth, love and support...
    honeybee2014 honeybee2014 22-25, F 2 Responses Jul 31

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    with normal vegetation for little bit more nostalgic privateness, this rooms are more appropriate for couples, honeymoonersmost affordable price assure We want you to pay back...
    Ardellaeh Ardellaeh 31-35, M 1 Response Aug 11

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    Actually, i am the older man looking for a young girl. A girl that wants to be dominated online and needs regurlar punishing.
    DomPie DomPie 41-45, M 2 Responses 3 days ago

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    I had an affair with a married man.. At first I didn't know that until he told me after we started to get serious! I'm a 18 yr old guy who is gay. He is very DL which his wife didn...
    avabooboo avabooboo 18-21, M 2 Responses Jul 22

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    I have never had sex with a condom simply because me and my man wants to start a family. We haven't had sex in 3 years due to log distance but hoping he comes soon from South...
    roselani2005 roselani2005 26-30, F 5 Responses 4 days ago

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    This is something I want to try I have never even dated a black man much less had sex with one but there is a first time of every thing right ??
    1Miserablemind 1Miserablemind 18-21, F 8 Responses Aug 5

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    I worked at a VBS camp two years ago during the summer. It was held during the night and I worked where I helped teach kids how to cook. I was the leader and I worked with a man...
    Southernpanda Southernpanda 18-21, F 3 Responses 6 days ago

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    I'm 16 years old and in highschool I'm going into my junior year and at the end of last year my teacher had me stay after class We had always sort of flirted and he told me that...
    Juliemadison Juliemadison 18-21, F 6 Responses 1 day ago

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    I love sex without protection! I'm 18, I've had sex 4 times during the age of 14. never used a condom. loved it!
    jessicatooreal jessicatooreal 16-17, F 13 Responses Jul 22

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    I had sex with over 200 girls before my 18th Birthday...
    Raddaddy Raddaddy 41-45, M 2 Responses Jul 24

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    I've only had sex with one girl. And it was amazing!!!! I like boys and I'm sure one day I'll find the right one
    Randi97 Randi97 18-21, F 7 Responses Jul 25

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    When I was really young there was a teenage girl with dwarfism in my neighborhood that I saw regularly. I don't think I was even old enough to like girls yet but there was...
    thatguythereoverhere thatguythereoverhere 26-30, M 2 Responses Jul 27

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    I have never had casual sex!
    thirdsense thirdsense 18-21, F 3 Responses Jul 28

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    I had a sexual encounter with two teen girls once outside. I dod write it down. But can post it. Anyone want to read it. Will post it to on comments or to your inbox
    Casualsexguy Casualsexguy 26-30, M 3 Responses Jul 28

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    I Havnt actually had an experience yet . My fwb and I have sext with couples and I find it Hott sexting with other females . It's fun when I'm at work and well my bf def gets the...
    Noismkr Noismkr 31-35, F 1 Response a week ago

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    I had sex with my teacher in year 9 in the school pool. It was great.
    zacisbest45 zacisbest45 16-17, M 4 days ago

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    I have always had sex without condoms. It feels better and is natural. This year it finally all caught up to me and now I'm 5 months pregnant. However that won't stop me and I'm...
    wanting1992 wanting1992 18-21, F 11 Responses 2 days ago

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    This year, I had a extremely attractive chemistry teacher. He's sweet, and has vibrant blue eyes, short blonde hair and a perfect body. Every time that I would look at him, I...
    Jeanpocket Jeanpocket 13-15, F 1 Response Jul 22

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    Not anymore. It was ok until I really fell in love. Then I just felt miserable after we broke up and I had casual sex. It's celibacy for me until I am in love again, I guess.
    FryMorgan FryMorgan 22-25, M 1 day ago

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    I want it so bad... Just the thought of being with another man makes me ready...
    SteelNettt SteelNettt 18-21, M 2 Responses Jul 26

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    Ive just always loved sex with other men
    bottomslut1 bottomslut1 18-21, M 1 Response 2 days ago

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    I miss having sex.... But I want to have meaningful sex with someone I love. I don't have anyone like that in my life yet. :(
    Grapemonster Grapemonster 22-25, F 1 day ago

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