Post
Experience Project iOS Android Apps | Download EP for your Mobile Device
This experience may contain mature content, as flagged by the community. Please click away if you do not want to see this content, or if you are not of age. To report inappropriate content, please email us.

I Had Crossdresser Sex With An Older Man

Personal Stories, Advice, and Support 119 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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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 6 Responses Sep 12

    Your Response

    Cancel
    I am so horny and want to have s e x with older man like 40's-60's. ;)
    Elizabeth214444 Elizabeth214444 22-25, F 3 Responses Sep 17

    Your Response

    Cancel
    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 2 Responses Sep 3

    Your Response

    Cancel
    I am so horny and want to have s e x with older man like 40's-60's. ;)
    Elizabeth214444 Elizabeth214444 22-25, F 16 Responses Sep 17

    Your Response

    Cancel
    I was nineteen when I kissed an older man in his late forties.Well actually he kissed me.Honestly, that was the best kiss I ever had.We were sitting in his car, warming up, while I...
    Outofeden Outofeden 31-35, F 2 Responses Sep 19

    Your Response

    Cancel
    YoungerWomenWithOlderMen.com Focus on Connecting Younger Women with Older Men Recently launched online age gap dating site, YoungerWomenWithOlderMen.com, has become popular between...
    tessacc11 tessacc11 26-30, F 1 Response Sep 22

    Your Response

    Cancel
    YoungerWomenWithOlderMen.com Focus on Connecting Younger Women with Older Men Recently launched online age gap dating site, YoungerWomenWithOlderMen.com, has become popular between...
    tessacc11 tessacc11 26-30, F 1 Response Sep 22

    Your Response

    Cancel
    YoungerWomenWithOlderMen.com Focus on Connecting Younger Women with Older Men Recently launched online age gap dating site, YoungerWomenWithOlderMen.com, has become popular between...
    tessacc11 tessacc11 26-30, F Sep 22

    Your Response

    Cancel
    YoungerWomenWithOlderMen.com Focus on Connecting Younger Women with Older Men Recently launched online age gap dating site, YoungerWomenWithOlderMen.com, has become popular between...
    sandycc11 sandycc11 26-30, F Sep 23

    Your Response

    Cancel
    YoungerWomenWithOlderMen.com Focus on Connecting Younger Women with Older Men Recently launched online age gap dating site, YoungerWomenWithOlderMen.com, has become popular between...
    sandycc11 sandycc11 26-30, F Sep 23

    Your Response

    Cancel
    I'm a 22 year old guy. And believe it or not, ladies, you're not a lone. The History with my girlfriend and I: We dated briefly in high school before she went off to college. She...
    daveR80 daveR80 22-25, M 1 Response Sep 21

    Your Response

    Cancel
    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 9 Responses Sep 13

    Your Response

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

    Your Response

    Cancel
    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 Sep 9

    Your Response

    Cancel
    I Am A Young Girl Looking For An Older Man!What should I do?
    QearlLee QearlLee 26-30, F 10 Responses Sep 18

    Your Response

    Cancel
    I so want an older man I am so h o r n y right now 50's-60's they make me so hot. ;)
    Elizabeth214444 Elizabeth214444 22-25, F 3 Responses 1 day ago

    Your Response

    Cancel
    I had an affair with mm before I met my husband. I was 19 and an absolute rebellious party girl. My family and I were going to a high profile society event and I went to get my...
    Ladygrey79 Ladygrey79 31-35, F 3 Responses a week ago

    Your Response

    Cancel
    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 Sep 13

    Your Response

    Cancel
    For the last few months I have started to fantasize about having sex with a close and very dear lady friend of mine and I can’t seem to get her out of my mind for some reason...
    bfox2608 bfox2608 36-40, M 2 Responses 4 days ago

    Your Response

    Cancel
    My girlfriend has been having sex with other guys, about 2 of them she had sex with multiple times
    jma13f jma13f 18-21, M 5 Responses Sep 7

    Your Response

    Cancel
    I've had sex with some 16yo's. I've done it with my cousin. And i've done it with my friends brother & his friends. (Mostly 14 & 15)
    WhiteGirl702 WhiteGirl702 22-25, F 2 Responses 1 day ago

    Your Response

    Cancel
    I have sex with my cousin all the time do you want to hear the stories ? ;)
    Vannnessaaaaa Vannnessaaaaa 18-21, F 33 Responses Sep 7

    Your Response

    Cancel
    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 6 Responses Sep 11

    Your Response

    Cancel
    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 4 Responses Sep 13

    Your Response

    Cancel
    I've had sex with a lot of men. It was great but I regret it all.
    TakeMeAway15 TakeMeAway15 13-15, F 9 Responses Sep 16

    Your Response

    Cancel
    Every time I see a beautiful pregnant woman walking with her man... Just makes me crazy jealous. I can't wait to have my own loving baby maker :) A man can dream I guess.
    Danimmortal Danimmortal 22-25, M 1 Response Sep 20

    Your Response

    Cancel
    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

    Your Response

    Cancel
    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 Sep 13

    Your Response

    Cancel
    First of all I want to make clear I am not the type of person that looks around looking for trouble or sleep around with just anyone, and that includes married women, But once an...
    BrantfordGuy42 BrantfordGuy42 41-45, M 1 Response Sep 20

    Your Response

    Cancel
    I want to have sex with one so bad, like 14-15. (Im 16 btw, it wont let me change it)
    Bimanwhore9 Bimanwhore9 18-21, M 2 Responses Sep 17

    Your Response

    Cancel
    I want to have sex with a female teacher in my school teaches maths,she's not attached and is only a mere 22 years old she has an a body like an hourglass,all the curves in the...
    TheGamechanger TheGamechanger 18-21, M 1 Response Sep 19

    Your Response

    Cancel
    I love having sex with strong young guys so they can hold me tight and never let go.
    Irishsunglasses Irishsunglasses 18-21, F 1 Response Sep 4

    Your Response

    Cancel
    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 4 Responses Sep 14

    Your Response

    Cancel
    I would probably go for sex with my close friends as part of friendships..i do not say it casual as it's with my friends and with whom I like to do everything I like feel like ...
    Ravidesai Ravidesai 41-45, M 1 Response Sep 22

    Your Response

    Cancel
    I would love to have sex with a lesbian
    wantayounglady wantayounglady 46-50, M 1 Response Sep 23

    Your Response

    Cancel