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I Had Crossdresser Sex With An Older Man

Personal Stories, Advice, and Support 119 People

    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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    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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    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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    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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    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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    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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    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 11 Responses Sep 8, 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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    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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    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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    Related Experiences

    It was a while back, i never told my mom that i had seen her with another man anyway, i was at my house (BTW im 14 my profile says different but yeah) alone and decided to go to my...
    Zinnylok Zinnylok 22-25, M 3 Responses 4 days ago

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    I'm so fascinated with older man. Especially if they try to pick up younger females. I am not in love with an older male, as I said I'm just fascinated with how they act.
    Meyrinfields Meyrinfields 16-17, F Sep 3

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    when i was 14 i had a private tutor,she was from new zealand ,her name was Ms Eve and was 24 yr old then.I would have to say she looks like an angel.It was normal studies for few...
    sunnysome sunnysome 26-30, M 1 Response a week ago

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    Honestly, it's too early to tell, but I feel like an obsessed teenager talking to this guy who is way older than me. I don't know why I fell for him as we hardly have anything in...
    UltraaViolencee UltraaViolencee 18-21, F 1 Response Sep 7

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    17 year old boy looking for a older man of any age to have sex with me! I'd do anything you want so message me?
    benw19 benw19 16-17, M 1 Response 6 days ago

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    I will miss him when he is gone.... It's been 2 years since I wrote my first post. My husband and I are still together, still making our way through life. I'm now 38 and he is 8...
    mssjeb2000 mssjeb2000 36-40, F Aug 30

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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 Aug 18

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    i want an older man to call daddy and i want him to call me baby or princess. i am very submissive love being spoiled. would love if he was older then 27
    juanitac juanitac 18-21, F 3 Responses 3 days ago

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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 3 Responses Aug 17

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    and I am an older man looking for a younger girl
    therapyguy therapyguy 56-60, M Sep 4

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    I had an affair with a mw for two years. She told me she just wanted me, and the sex for both was incredible. It replaced both of our sexless marriages. - and you wouldn't...
    TheOtherGuy35 TheOtherGuy35 46-50, M 2 Responses a week ago

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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 7 Responses Aug 17

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    Looking for younger, gay guy interested in a relationship with an older man, real or on line to start.
    travis43 travis43 56-60, M 1 Response Aug 25

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    I hate how ppl who don't know me look at me and think I'm not a virgin...like wtf? And I hate how some people I know always tell me "just do it" "you're too pure" "gotta do it...
    Midnightangelx Midnightangelx 16-17, F 1 Response 3 days ago

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    I meet a girl through a lesbian site.. She's married but she said that her husband and her don't have sexual relationship. Then we chat the whole night. She said she had a dream...
    taurus11 taurus11 26-30, F 1 Response Aug 30

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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 16 Responses Aug 18

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    My girlfriend has been having sex with other guys, about 2 of them she had sex with multiple times
    jma13f jma13f 18-21, M 1 Response Sep 7

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    Just before establishing Task Settlements, Sally labored in house development and expenditure sales. Undertaking Settlements was at first arrange while in the distinctive pursuits...
    Yolandajn652 Yolandajn652 31-35, M 1 Response Aug 22

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    Numerous times started when I was 16 they were in their 30's was having sex with 3 of them stopped after I turned 22
    Ant35 Ant35 31-35, M 3 Responses Aug 25

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    I have sex with my cousin all the time do you want to hear the stories ? ;)
    Vannnessaaaaa Vannnessaaaaa 18-21, F 24 Responses Sep 7

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    I found out 2 weeks ago my girlfriend of 3 years is pregnant with another mans baby, I really don't know what to do, she wasn't drunk or under drugs, she slept with him and found...
    dragonninja dragonninja 18-21, M 3 Responses 5 days ago

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    I was having sex with my mother in law when my wife called her to talk about me. To complain that she thought I was fooling around on her. My mother in law assured her that she did...
    Mrhughcock Mrhughcock 36-40, M 1 Response 3 days ago

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    I've had sex with a lot of men. It was great but I regret it all.
    JustMeAsMyself JustMeAsMyself 13-15, F 1 Response 13 hrs ago

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

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    hi i am from new delhi india i want to have sex with a sexy girl i will pay her gd bt i dnt hv ma prsnal place to **** plz help me out wht to do
    sexyboy034 sexyboy034 18-21, M 1 Response Sep 2

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    I love having sex with my boyfriend. We have the best sex ever!! I belief sex is very important in a relationship.
    Nathaly22 Nathaly22 18-21, F 4 Responses 3 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 Aug 19

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    I love sex without protection! Love to feel every ridge and vein. Ask me more in the comments and I'll answer... Gotta avoid those that watch since they are blocking my stuff now...
    catiemae87 catiemae87 26-30, F 26 Responses Aug 25

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    I love sex without protection, love being inside a women, and feeling every sensation....
    red1235 red1235 41-45, M 1 Response Aug 31

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    I love having sex with strong young guys so they can hold me tight and never let go.
    Irishsunglasses Irishsunglasses 18-21, F Sep 4

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    Even though we don't have a label on our relationship, I still want to have sex with him and kiss him and hug him and cuddle . I like the way he feels inside of me . I don't know...
    neuroticgal neuroticgal 22-25, F 2 Responses 3 days ago

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    i am not feeling good bcoz i had a fight with my best friend. she was always with me in hard times and also every in moment. now she is ignoring me i dont know how to apologise to...
    shreyanancy shreyanancy 13-15, F 2 Responses 4 days ago

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    He's 22 years older than me.. I just wanna say, age ain't nothin but a number. He doesn't even look his age. When we're standing next to each other and he's not in his business...
    KaiFyre KaiFyre 26-30, F 3 Responses Aug 26

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    I am 20 and my boyfriend is 38: an 18 year difference. It's only been a month so I don't have much to say, but it's not awkward or uncomfortable like so many people warned me. He's...
    Eoligos Eoligos 18-21, F 2 Responses Aug 25

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    Or cyber with :) the older the Better come and get me
    Happiness412 Happiness412 18-21, F 5 Responses Aug 27

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    Please respond with authenticity, suppor