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I Had Crossdresser Sex With An Older Man

Personal Stories, Advice, and Support 115 People

    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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    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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    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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    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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    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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    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 5 Responses May 13, 2012

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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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    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 9 Responses Sep 8, 2013

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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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    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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    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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    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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    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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    Related Experiences

    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 4 Responses 14 hrs ago

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    would like to go further
    livingofgrid livingofgrid 56-60, M 2 Responses 5 days ago

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    I'm 53 and the gentleman with whom I'm very attracted to is 71. I really love him a great deal. He's super intelligent which I love, witty, funny a deep thinker, very philosophical...
    Dahling61 Dahling61 51-55, F 2 Responses Jul 17

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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 Jul 21

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    I am in love with an older man. He's 20 years older than I am. We are both single but have dated secretly for almost a year because we work together. Recently he has talked about...
    winelover1 winelover1 31-35, F 2 Responses Jul 20

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    Well, I started highschool, I am much more mature than the rest of the high school. I just keep to myself and focus on the future, I've had an unbelievable past for someone of 15...
    DreamLurker DreamLurker 13-15, F 1 Response Jul 12

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    Best Older Men Younger Women Dating Site - AgeMeet.com AgeMeet.com a website specifically designed for older man and younger woman relationships and older woman and younger man...
    cindytongcc11 cindytongcc11 26-30, F Jul 20

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    Best Older Men Younger Women Dating Site - AgeMeet.com AgeMeet.com a website specifically designed for older man and younger woman relationships and older woman and younger man...
    cindytongcc11 cindytongcc11 26-30, F Jul 20

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    ARE YOU AN OLDER MAN SEEKING A YOUNG WOMAN? "Datingayounerwoman.com is a newly launched unique dating service, which helps young girls looking for older men or vice-versa...
    datingayoungerwoman datingayoungerwoman 22-25, F Jul 2

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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 1 Response 1 day ago

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    Man I'm just chilling here with my dad's friends, it's nice interacting with older. People who run a business or talk about work
    baconassassin baconassassin 18-21, M 1 Response Jul 18

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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 a week ago

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    Okay I live in Michigan I was 17 now 18 at the time and the age to consent to sex is 16 I'm guessing that's with any age but below 16. Anyways this 42 year old police officer who...
    cupcakes38 cupcakes38 18-21, F 2 Responses Jul 19

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    Okay I live in Michigan and the age to consent to sex is 16 I'm guessing that's with any age but below 16. Anyways this 42 year old police officer who lives in Canada came over the...
    cupcakes38 cupcakes38 18-21, F 3 Responses Jul 19

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    I want to have sex with a big women so I could sexually pleasure her hit me up
    dmedina513 dmedina513 36-40, M Jul 4

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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 11 Responses a week ago

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    I have never had casual sex!
    thirdsense thirdsense 18-21, F 3 Responses 1 day ago

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    I've never had sex without a condom before . But I heard it's so much better . Idk I'm nervous about that kinda stuff .
    oabutler oabutler 18-21, F 19 Responses Jul 7

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    My dog is the first living thing I've ever had sex with, she was tight, but then I let my friend borrow her and he ripped her a new *******. But moral of the story is, does anyone...
    Guuuu Guuuu 18-21, M 4 Responses Jul 17

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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 a week ago

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    I had sex with over 200 girls before my 18th Birthday...
    Raddaddy Raddaddy 41-45, M 5 days ago

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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 4 Responses 4 days ago

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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 days ago

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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 1 Response 1 day ago

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    In 2000 I had sex with my first black woman 3-4 times. I was 20. She was 30. She reconciled with her husband of 7 years and I returned to Russia. I did not know she gave birth to a...
    SmolenskBorn SmolenskBorn 31-35, M 2 Responses Jul 10

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    Hi my name is Jan I am 21 and have sex with lots of guys. I work at a bar and always bring guys back to my place after work and have sex with them. I have a no condom rule. I want...
    jantheslut jantheslut 18-21, F 8 Responses Jul 17

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    I think about my wife flirting, kissing and having sex with other men.
    Stky2001 Stky2001 36-40, M 7 Responses Jul 1

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    Sex without love is empty feeling. Without emotions, it's simply just an physical act that i'm not interested in. The connection and bond you have with someone you love is what...
    evesss evesss 18-21, F 2 Responses Jul 6

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    Right after I lost my virginity I got on birth control. It didn't take much to talk me into sex without condoms. It's super messy to clean up and I'm scared of getting STD's but it...
    cuteshyginger cuteshyginger 16-17, F 22 Responses Jul 18

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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 days ago