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I Have Sucked Cock While Dressed Like A Woman

Personal Stories, Advice, and Support 590 People

    Curiosity Got To Me

    For the first time in about 13 years, I sucked another man’s ****. I was dressed up at home in thigh-high-fishnet stockings with garter belt, a pencil skirt, and a sensible top. While this isn’t usually sexual for me I got curious and checked out Craig’sList. I was...
    JosetteLaRoc JosetteLaRoc
    36-40
    May 19, 2013

    I was only half dressed, but I sucked two *****. Does that count?

    The other day, before I left work I changed into the stockings and thong panties in the below anonymized picture of me and put my work clothes over them. On the drive home, there is a cruising spot where guys park on a deserted, dead end road off the freeway. I went there and...
    deleted deleted
    26-30
    3 Responses Jan 19, 2012

    I Went Out Dressed As A Woman Searching For **** To Suck

    Ive been transforming into a woman for a long time , i know i can be relay convincing so i set out one night find a man in town center (no gay clubs) flirt , kiss and seduce him then take him up a side street then throw him against the wall pull down his pants and grab his...
    hornydevil2710 hornydevil2710
    36-40
    2 Responses Oct 17, 2012

    Sucking While Dressed

    Hello all I have been dressing ever since i was 12yo. at first I did not realize that I wanted to do this. I ws first dressed at a halloween party as part of a parlore game loosing I was transformed by the girls. Well as the years past I tried to stop dressing but never could...
    prettypenny prettypenny
    51-55, M
    8 Responses Jul 29, 2012

    I Just Did

    i just had a nice **** in all my holes and he *** in my mouth and i love it and i want more i love suck **** and haveing them *** in me
    deleted deleted
    26-30
    2 Responses Nov 3, 2010

    I started out heterosexual

    and remained that way for the first 40 years of my life . Then my wife hit menopause and quit being interested in sex. Frustrated from abstinence and not wanting to have an affair with another woman to satisfy my desires, I began crossdressing as a way to release some sexual...
    chrissyk48 chrissyk48
    46-50, M
    2 Responses Nov 26, 2014

    Force Fed As A Teen

    This all occurred when I was about 14 and in Junior HIgh. The result was high school years filled with please and excitement I had never anticipated. In gym classes we had to shower and I was always self conscious became I did not have as much "equipment" as a lot of the other...
    deleted deleted
    26-30
    3 Responses Jul 2, 2011

    Went Out

    One evening my SO and I had a spat and I stormed out of the house.  I was dressed as a women which is an everyday practice for me.  I went to a bar and started drinking scotch.  I had been there for three or four drinks when a nice looking man approached me and...
    robbiemaid robbiemaid
    22-25, M
    3 Responses Apr 22, 2010

    Sucking

    Oh I just love sucking **** while dressed all sexy getting real men hot. It makes me feel so feminine I just love it nothing more exciting hot and sexy than getting a man hard and sucking his **** to completion.
    Cristine3030 Cristine3030
    41-45, T
    3 Responses Feb 11, 2012
    alexiswcd alexiswcd
    56-60, T
    2 Responses Mar 9, 2015

    What Better Way To "be" A Woman

    When I am a woman, what better way is there to be a woman than to do what a woman would do. I love sucking a guy when I am dressed as a woman. The idea doesn't appeal as much to me when I am in guy mode. But being a woman makes me want to do all that a woman would do.I love...
    fayeanneleigh fayeanneleigh
    51-55, T
    8 Responses Jan 22, 2010

    And Want To Do It Again.....

    I had only had one **** in my mouth before, so this was my second time.I was at my house dressed in short skirt, low cut (women's) blouse,bra and breast forms, panties, stockings and high heels. I was feeling somewhat horny and brave but most of all curious what it would be like...
    RayanneA RayanneA
    56-60, M
    1 Response Apr 4, 2012

    In Lingerie

    Well it was only my second time sucking a **** - and with the same guy - an old friend. I told him last time about my *********** fantasy and he obliged me. Well we met up again. While drinking I asked if he would help me live out another fantasy. I explained that it involved...
    deleted deleted
    26-30
    1 Response Oct 2, 2012

    My " Date " With ****!!!

    One night my friend, I'll will call his ****, called and asked if I wanted to go out. He said we could get some beer and drive around the back roads around where we live. I agreed, but asked him if I could get dressed up and be his "date" for the evening. He agreed. I wasn't...
    davis36a davis36a
    61-65
    5 Responses Nov 19, 2011

    Sucked **** While Dressed Like A Woman

    I went to Doc. Johnsons adult book store outside Columbus dared myself to go in dressed looked at a few books for five minutes then went to my car a guy came out tap on my wondow said he like what he saw talked me in to getting out, I let him touch me feel me up I was nervous not...
    MonicaBond MonicaBond
    36-40
    2 Responses Nov 27, 2009

    On a number of occasions with other cds

    and guys too. I preferred it in a private place, but have dne it outside and in a car too.it has been a very long time since i have.
    deleted deleted
    26-30
    Apr 23, 2015

    I have ben seeing a guy

    who is very well endowed for about 6 years now we get together for a lunch date 3 to 4 times a week when we first started this get together in his car and I would service him over the lunch hour at one point he was supposed to be keeping an eye as I was busy when a cop walked up...
    Girlonherknees Girlonherknees
    46-50, T
    Mar 22, 2016

    Uncontrollable Desire

    A recent event led into me being in a nearby city alone with time to kill and a few extra dollars cash to play a little. I decided I'd like to visit a couple of adult bookstores I've been to before, but not for a few years. As I started to drive to the first one, I spotted a...
    bar1cd bar1cd
    41-45, T
    2 Responses Apr 12, 2013

    I Have Had A **** In My Mouth While Dressed

    I was shaved smooth, and had a black dress with cute butterflies on, 36C black bra with breast forms, black french-cut panties, black lace garter belt connected to lace topped thigh highs, sparklie pumps on and i was down on my knees when I was sucking my first ****.... it was...
    karenjensencd karenjensencd
    46-50, T
    6 Responses Oct 27, 2013

    A ***** For The First Time

    i have twice dressed as a woman and entertained males.  Each time it was a dominant male.  The first time, i entertained him at my apartment.  He had me unlock the door on receiving his phone call.  This meant he was outside.  i was then to blindfold...
    roxiefox roxiefox
    56-60, T
    3 Responses Dec 8, 2009

    Watching Shemale **** With Someone

    I just shared this as a response to one of our sweet members fantasies of watching shemale **** with someone. Hope you all enjoy! I've actually done this several times! The last time was about a month ago. I went to his home after meeting him on Craigslist. I wore my white...
    Lisagurlll Lisagurlll
    36-40, T
    5 Responses Jun 4, 2012

    Uncontrollable Urge

    So I am a lifelong crossdresser, and have always been extremely turned on by pantyhose. I've done a lot of things, and had a lot of fun, just read some of my other stories. :) Lately I've been in a "purge", this is what us crossdressers go through every so often where we try to...
    bar1cd bar1cd
    41-45, T
    1 Response Jul 18, 2013

    On My Knees

    I was on my knees once, sucking an old man's ****.
    smoothfemme smoothfemme
    31-35, T
    Nov 2, 2012

    I Have Sucked Dicks While Dressed

    I have been crossdressing most of my life. Early on, my sister helped me because she wanted a sister. She hooked me up with a BI friend of hers who I would eventually have sex with. That guy was a turning point in my life and even though I am married, I know I like to suck...
    deleted deleted
    26-30
    6 Responses Aug 22, 2010

    My Second Ever **** Sucking Experience

    He went by the on line user name of "buntcakeking" and I had met him on line through a yahoo user group. He was younger than me, and had a lovely 7 inch ****.  He was also my first black **** too.  We were both on Camp Leatherneck in the helmand province district of...
    Sissycdmichelle69 Sissycdmichelle69
    46-50, T
    Aug 3, 2012

    It's almost natural for me now.

    I arrange to meet men on Craigslist and after a screening process, sharing pics, etc. I find someone I can date regularly. I've dated for as long as three years and as little as a month. I prefer to date for a long while with a man I can call my boyfriend. Now, the kicker is...
    Lisagurlll Lisagurlll
    36-40, T
    1 Response Feb 20, 2014

    Such A Turn-on

    I began sucking dicxs when I was 15 and until my early 20's it was always as a "guy". It's funny now, but as I reached my 20's and my dressing had progressed to a point of no return, I was still hesitant to let anyone know I wore panties & thigh-hi stockings. One night, though...
    janusatv janusatv
    61-65, T
    2 Responses Apr 21, 2012

    The First Time

    My gf loved to dress me as a girl and i loved to be dressed. She had a party and she wanted me to be a girl that night. I agreed to it> She dressed me up panties bra pantyhose slip and a dress high heels and makeup. at the i was drinking a lot and had to use the restroom. A man...
    marykay51 marykay51
    51-55, T
    2 Responses Mar 2, 2011

    Last Night

    Hi all I had a rather eciting evening friday and wanted to share with this group. Well ii was feeling a lot depressed lately you know with the economy and life in general not being all one might wish. I decided to put on some sweet fe things and go looking for friends. I showered...
    prettypenny prettypenny
    51-55, M
    4 Responses Jan 19, 2013

    My Date With A Gorgeous Black Man

    Well, I have been a sissy all of my life, and I have dated several men. Being on a date dressed is one of the most wonderful experiences I have ever had. And I have had some exciting dates. But this one is one that i will never forget. You see, I started dating Black men...
    ChristinaMarietg ChristinaMarietg
    51-55, T
    2 Responses Nov 20, 2011

    Gaining Tougue Talent

    I like many of you as a little horny early teen 13teen or 14teen I could not go out dressed. Oh I wore little panties and when I went out with a boy, who knew I was a sissy and wanted me to suck his **** off, which is the “Bestest” for me there was a boy I met at a party that...
    NastiRabbitt NastiRabbitt
    22-25, T
    4 Responses Jan 5, 2013

    I Really Want Men To Add Me So I Can See If We Could Meet Up Somewere !! (l)

    i need mento add me onthiweb page so i can mingle and i can meet them ill describre m e to you ima ball, happy ,want sex sometimes or all th times im a model i have ddsize boobs im skinny i have blonde hair and i have brown eyes all my love hollie. xxx ADD ME EVERYONE ESPESIALLY...
    luckmypussy luckmypussy
    22-25, F
    8 Responses Nov 30, 2010

    Sucking Dressed As A Girl

    It feels so good looking up while sucking a man him patting u on the head calling u a good sluty gurl. Makes u feel so dirty and helpless.
    SissyTony SissyTony
    56-60, M
    4 Responses Jul 13, 2010

    Sucked A Male To ******* Dressed In Lingerie

    i HAD PREPARED MYSELF VERY CAREFULLY. rEMOVED ALL MY BODY HAIR SO WAS SMOOTHE AND SWEET SMELLING OF MUSK PERFUME. i WORE A TIGHT PAIR OF LATEX BRIEFS SO MY CROTCH LINE WAS SMOOTHE TOO. a SATIN BULLET BRA,SILICONE BREAST FORMS A SEET HROUGH CHIFFON CHEMISE LACE TOP THIH HIGH...
    Carolaus Carolaus
    51-55, T
    1 Response Dec 21, 2010
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