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I Crossdress to Please Older Men

Personal Stories, Advice, and Support 110 People

    Love Older Men

    Moved to a new area from where i had really enjoyed life as a cross dresser and being friends with men same age and older, it was the older men that i liked best. Always trying to be romantic to the point of totally overdoing it. However due to fiances had to move to a new area...
    Bevintights Bevintights
    56-60, M
    Jul 12, 2011

    Dress To Please Older Man

    I have an older man that I crossdress to please, he has special outfits he likes to see me in and I know by now what he likes the most. He will buy certain items that he would love to see me in and I am very glad to wear them for him. I know what he likes and what will be the...
    alexiswcd alexiswcd
    56-60, T
    17 Responses Oct 18, 2012

    Looking to Be Dressed

    Married NJ tv,47, looking for an older guy with his own place. I would come over and dress up slutty for him. I would suck him off and let him **** my ***, give me facials, what ever he wants. I would like it to be a regular things, once every couple of weeks.
    deleted deleted
    Jul 15, 2009

    I love to crossdress

    and I decided to take it to the next level by putting an ad in Craigslist seeking a gentle older man with whom I could go into the woods and pose for. A gentleman named John was among those who answered the ad. We spoke by phone and he seemed like a really kind man. So he picked...
    stonedsoulpicnic9 stonedsoulpicnic9
    Jun 26, 2015

    I Think I Have A Older Men

    i have been seeing a man that 55 and i love it he has 9 inch **** and he treats like a women he holds me after sex and loves spending time whit me i miss him when he is not whit me. i am so happy i hope it last
    deleted deleted
    1 Response Jan 28, 2011

    About Me

    VERY VERY VERY ORAL gentle Black bottom/switch "master", very interested in being the publicly dominate force in a sexual science experiment ISO of a honey dripper that can *** like a flood to quench her masters thirst. | am easy on the eyes, cute in a boyishly (so I...
    blassy blassy
    Jul 5, 2009

    A Craigslist Hook Up...

    So my wife was away a few months ago and I was in need of a quick satisfaction. I put a post on Craigslist to hook up with someone that wanted a quickie with a CD. I got over 50 responses within a few hours. I picked one that was local to me and emailed him back. We talked on...
    naughty1770 naughty1770
    31-35, T
    1 Response Feb 3, 2010

    I Dress For Older Men

    I dress in a slutty outfit for older men. They treat me like a woman and use my ***** and mouth.
    smoothfemme smoothfemme
    31-35, T
    Nov 1, 2012

    Looking to Please

    I'm a married 47 year old closet crossdresser in NJ. I haven't dressed for anyone in many years but would love to dress up with or for an older guy. I wold love to make out with him and I'ld love to have him guide my mouth to his lap.....
    deleted deleted
    1 Response Apr 27, 2009

    I Love To Submit To Older Men

    I have an older friend (52) who I just adore. He buys me sexy lingerie that I model for him, and he also has been training me to take on larger and larger ******. He is a massage therapist and we have the most wonderful sessions where he will rub down my smooth body with...
    sissynikkicd sissynikkicd
    41-45, M
    Jul 20, 2013
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