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I Had Crossdresser Sex With An Older Man

Personal Stories, Advice, and Support 127 People

    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
    2 Responses Mar 28, 2013

    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
    6 Responses Sep 11, 2012

    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
    1 Response Dec 23, 2010

    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
    1 Response Feb 10, 2013

    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
    1 Response Feb 16, 2011

    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
    1 Response Feb 20, 2013

    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
    Nov 21, 2012

    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

    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
    2 Responses Mar 29, 2013

    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
    3 Responses Apr 12, 2010

    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
    3 Responses Mar 15, 2012

    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...
    deleted deleted
    11 Responses Sep 8, 2013
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