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I Sex With An Older Crossdresser

Personal Stories, Advice, and Support 31 People

    I am the older and tonight I am getting

    together with a young man who is 35 yrs younger than me. We both will be going full on girly sissy! I am sure there will be hot LESBIAN sex involved. For me black panties and pantyhose, my blue bra, blue jean skirt and an ivory colored top. I'll switch into my bustier later on...
    aprillaw aprillaw
    61-65, T
    1 Response Sep 13, 2014

    I love being on my knees

    and my tight gurl *** is pounded. I met a cd same age as me few weeks ago on trip. She banged me three times. Each time was better. So wet!
    susiecdgurl susiecdgurl
    61-65, T
    2 Responses Jun 29, 2014

    My Freinds Dad

    My first crossdressing sexual experience was with my friends dad. I was 19 & he was 52. My friend & I were looking through his cupboard in search of some **** when we came across some photos of his dad dressed in lingerie & heels. My friend became highly embarrassed & left the...
    deleted deleted
    26-30
    3 Responses May 5, 2013

    Its Not The Size That Counts

    I have been close freinds with a Crossdresser named Crystal for many years now. He's mid 50's & has a rather small ****. When fully erect he's no more than 4 inches max. The poor dear,I Will never forget how embarrased he was the very first time I pulled down his panties but as I...
    deleted deleted
    26-30
    8 Responses Sep 18, 2013
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