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I Love to Crossdress

Personal Stories, Advice, and Support 4,370 People

    My First Female Shopping Experience

    I haven't written about a new experience in a while because I haven't had too much time to do anything, like dress or go out. At least until a week ago (hence the new story). So I had been looking for some new clothes and didn't really know where to go. I've ordered clothes...
    iheartdressing iheartdressing 26-30, M 27 Responses Jul 28, 2013

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    Do you ever have days

    when your inner Woman is screaming to be let out? This is one of those days! I want to put on a Sundress and twirl and do cartwheels in the front yard. I want to go shopping and try on and model every cute dress, jeans, shoes or skirt that fits! I want to have a frilly lunch at...
    parttimelisa parttimelisa 51-55, M 7 Responses Jul 19, 2015

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    just looking at different experiences about

    cross dressing and guys wearing female underwear, wanted to clear something up, for me it's not a turn on but as natural as any female or any male picking what panties to wear or what boxers to wear, I think a lot of guys are dressing to get turned on and which this is good...
    deleted deleted 26-30 5 Responses May 11, 2015

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    since I was 5 I have had a love of all things

    girly from the panties to high heels. this started with my sisters panties and built from there to wearing dresses and skirts as often as I can. still trying to master make up but not bad noe
    jamie172 jamie172 46-50, T 3 Responses Jul 20, 2014

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    An Accidental Meeting At My Hotel

    I always dress when I travel. I finish my work, maybe pick up some dinner and return to my hotel room. I immediately take off my drab male clothes, clean up, and slip on a bra, my wonderful silicone forms, and a pair of panties. Then I do my makeup. After that, I usually slip on...
    LizWisconsin LizWisconsin 56-60, T 5 Responses Jul 13, 2011

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    Although my wife knows about me wearing tights

    / panties. I sometimes wish that I lived alone so I could buy more stockings, tights, panties and heels. Although she accepts it, I feel I can't go as far as I want as often as I want.
    deleted deleted 26-30 7 Responses Aug 12, 2015

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    And losing my virginity to a man

    A few weeks ago on a weekend My Neighbour lady asked me to go to her parents' home and stay there for a day to clean their home and do some other works. She is like a domme to me and as I had gone there ib past I decided to go there. On Saturday I reached there before lunch. Her...
    AnneTheSissy AnneTheSissy 22-25, M 16 Responses Aug 17, 2013

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    No easy way...crossdressing is not inexpensive.

    I prefer lingerie to dressing in full drag with makeup, hair, heels and beautiful dresses so it's not as expensive as it could be. Lingerie is not cheap, panties and bras are not cheap so I decided to check out eBay for a few deals. I've purchased nighties, pajamas and breast...
    Purplesatinthong Purplesatinthong 31-35, M 5 Responses Oct 26, 2015

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    Can't wait to get home to my wife I just got a

    new wig and breasts so I'm stoked but truly she is the best wants me to have a new fashion sexy punk girl so I'm changing my visas and probly hiten the town
    abillawolf abillawolf 26-30, T 6 Responses Aug 11, 2014

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    It is really nothing,

    but I have worn panties under my male clothes for 6 days. My wife does not approve. She is homophobic. I have never had any sort of a bi relationship. Not interested. I am frustrated. .
    Goose1963 Goose1963 51-55, M 5 Responses Jul 24, 2014

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    The Dress

    Before we were married, my girlfriend and I were invited to a mutual friend's wedding. My girlfriend decided to make her own dress. Since a lot of her work friends would be there she decided that the dress had to be spectacular! I think that she must have spent about two week's...
    Jaimee101 Jaimee101 56-60, M 6 Responses Aug 26, 2013

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    Started when I was young.

    Very much a part of who I am today.
    pk96701 pk96701 22-25 Jan 31, 2015

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    Dress Shopping

    The biggest problem with taking four dresses into the fitting room is the danger that you will adore more than one of them! Never even tried on the men's dress shirt I took in there with the four dresses. I picked the largest fitting room at H&M, and if there were security...
    GirlieSpirit GirlieSpirit 41-45, T 9 Responses May 23, 2012

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    Midnight Driving &Amp; Walking...

    It was about summer a year ago, I dared myself to go outside fully cross dressed. I live in a college town and summer time made the campus area quiet empty at night. I wore a purple push-up bra with matching thong panty, a black top, a short skirt, and a pair of heels. I drove...
    VSaddict VSaddict 26-30, M 7 Responses Jun 24, 2013

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    Last Night!

    So last night after having a few cocktails, some dancing, and fun, my wife and I came home and it was time to have some fun!! We started to fool around and she asked me what I was thinking about, now of course "you" is te right answer, but I also said, I wanna dress up! She...
    NvPantieLVR NvPantieLVR 26-30, M 13 Responses Feb 21, 2013

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    As I have written previously,

    I have had the same wonderful assistant for 28 years now. Today was sweltering, and I had to walk ten blocks for a meeting. When I returned, hot and miserable, she looked at me and said I should be wearing a cute summer dress and then I would have felt better. Really. I...
    Kim1girl Kim1girl 56-60, T 42 Responses May 28, 2014

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    I got a new pink satin dress today.

    I love it. I feel so sexy every time I get a new one.
    deleted deleted 26-30 2 Responses 5 days ago

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    I started when I was about 8 wearing my

    Mother's pink silky knickers and loved the softness next to my skin, I loved it and now I wear silky lingerie every day and will never change.
    timothy1994 timothy1994 22-25, M Feb 9, 2015

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    Making My Day A Sexy One

    I have just been shopping. Weather was awful. Bought myself a sexy new black and white mini skirt some new panties and gorgeous sheer nylons. Charlotte time lol
    Charlotte59 Charlotte59 51-55, M 7 Responses Dec 29, 2012

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    The past week I have been house sitting

    for the most attractive girl and her family. I have liked this girl for a very long time. And I entered her room to the strong smell of her perfume. It was so arousing. I was shocked to find a whole basket of unwashed cloths. Panties fresh with discharge. Tasted so good. Then I...
    Zoe24 Zoe24 22-25, M 6 Responses Jun 24, 2014

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    I am just like every other cross dresser out

    there. I 'm married, father of grown children, transform myself whenever I can and although my spouse has known about my "second self" for nearly 35 years, she has never really accepted my hobby, or need to feminize myself from time to time. I wish it was different.
    MCTV MCTV 66-70, M 9 Responses Aug 10, 2014

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    royalflush70 royalflush70 41-45, M 3 Responses Jan 28, 2015

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    This morning I was having my usual Sunday

    morning coffee with a group of guys. They are all about my age, and we just happened to see each other every Sunday morning, so we have become an ersatz group. It's been interesting watching their reactions to my growing feminization. So far, it's been universally...not really...
    PennySterling PennySterling 56-60, T 11 Responses Jul 13, 2014

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    My New Roommate!

    The second semester of my freshman year, a good friend of mine had a roommate conflict and she asked me if i wanted to take over the lease. I decided i needed out of the dorms and signed the lease with her. (She does not know that I am a crossdresser) The first weekend she...
    imadeafakename imadeafakename 22-25, M 12 Responses Sep 12, 2012

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    just realized I have more skirts

    than pairs of pants and then I have my dresses! Out of control and loving it :)
    michelletrans michelletrans 51-55, T 8 Responses Jun 16, 2014

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    You'D Fit Better In These!

    Last night my girlfriend commented on how female I've become even though I dress as a guy everyday. Guess my hormones worked well enough to make her take action. I never go out dressed as her but only play inside. Last night my gf decided I should risk more after she said I can...
    IWillBeReese IWillBeReese 51-55, T 10 Responses Apr 19, 2013

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    I'm going to the doctor this morning

    and having a checkup. As any self respecting gurl would, I'm taking a scented bath and shaving smooth all over. When I'm getting dressed I'll apply scented body lotion all over to add to the feminization of my skin. Before I put on my panties and bra, I'll tie a little pink...
    Bellringer2c Bellringer2c 56-60, T 6 Responses Mar 24, 2014

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    deleted deleted 26-30 5 Responses May 6, 2015

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    Avon Calling

    There I was reading some EP stories with my man clothes on with a pair of black panties and matching bra when the door bell rang. I answered the door. There was a nice middle age women asking for the women of the house. I told her that she was gone and would not be home until...
    cdjo cdjo 41-45, M 11 Responses Mar 15, 2013

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    Been dressing on and off

    since I was about 12 with my mom's lingerie. As I got older I started having my private stash to play with but this has grown, since I can dress freely in the evening. I'm still working on going out more dressed but for now its just drives at night and wearing things underneith...
    timcdofsd timcdofsd 51-55 2 Responses May 27, 2015

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    It's getting to be that time of year again.

    Spring and summer, when people go on vacation meaning they need somebody to housesit. Already have my first job lined up. I can't wait to share my crossdressing adventures with you here on EP 😘
    Zoe24 Zoe24 22-25, M 1 Response Mar 12, 2015

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    So for many years now,

    I have crossdressed on and off. It started off at a very young age that when I would go shopping with my mom I found a yurning to wear girls clothing, dresses in particular. As I got older, as I got an allowance, I started to purchase panties to wear and hid them in my room...
    cricket88 cricket88 26-30, T 4 Responses Nov 20, 2014

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    I would like to find a friend in Michigan to

    crossdress with. I'm lonely always going shopping and what not by myself. if your in the state of michigan message me.
    deleted deleted 26-30 2 Responses Jan 9

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    My wife wanted to know

    why I was leaving so early for therapy today. I said that since I had a place to hang out and dress........I should. And besides, I was hoping to get a new chunky necklace to help concile my man chest. Eventually she calmed down and began trying to find something that I could...
    JessicaDale JessicaDale 51-55, T 8 Responses Jun 10, 2015

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    Shopping Adventure With Mistress

    Thought I would share this story in here as well. My Mistress/wife and I decided we would go to another town to do a little girlie shopping for me. A well known store for bigger girls was where we were heading and I can't describe how nervous I was, just driving over. The...
    sissyhubby12 sissyhubby12 46-50, T 10 Responses May 18, 2013

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    My Ultimate Crossdressed Fantasy

    I have had this fantasy for some time now so here it is! Hope it doesnt offend anyone, but after all it is just a fantasy! I go to my gf's house and she is waiting for me, she has a wicked smile and tells me she has a great idea. First of all she tells me i must dress in...
    michellecd michellecd 22-25 12 Responses Dec 12, 2008

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    On Vacation

    My name is Sammi and my wife of ten years is Sue. I have been interested in cross dressing since about 10 years old when I would try on my mother’s panties when she was not home. I remember when I was younger than that when I was 3 or 4 and my mother would be sitting at the...
    sammi11 sammi11 41-45, T 44 Responses Apr 6, 2011

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    Omg!!!

    My heart is ready to beat out f my chest!!!! I just got done shooing at Ross and I bought my first nightie!! I am so excited, but on top of that I also bout two really cute skirt panties! I was doing pretty good walking through the aisles and looking for what I wanted, I even...
    NvPantieLVR NvPantieLVR 26-30, M 14 Responses Feb 7, 2013

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    Accepting My Crossdressing

    Like many who cross dress I had struggled with this for many years. I started as a teen wearing my mom's things then whenever I had the house to myself for extended period of time I would dress in her things. Tho I really enjoyed it I still felt guilty after. When I was...
    glorialamuse glorialamuse 56-60 30 Responses Apr 25, 2010

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    I love the feeling of panties

    and bras. It is so invigorating and exciting! Hope to do this with others some day!
    jordangrlee jordangrlee 26-30, M 3 Responses Jul 27, 2015

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    Why I Enjoy Crossdressing

    I have to say I am a part-time gurl. I've been dressing most of my life and truly enjoy my feminine side. I find dressing like a woman to be so pleasurable. One reason is that it allows me to escape the need to act manly or ‘macho’. It is a real escape, to abandon the...
    Kathy2U Kathy2U 46-50 13 Responses Oct 25, 2012

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    First Time: I came to crossdressing by way of

    my obsession with pierced ears. My older sister walked in on me while I was attempting to pierce my own ears when I was 15-years-old. It was the summer before my sophomore year of high school. This lead to me having to fess up and explain my interest in feeling girly and her...
    Michelleinside Michelleinside 31-35, M 4 Responses Jan 28

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    I Love wearing pantys.

    I like being manly actually, I can protect and take care of my girlfriend, do hard work, and feel good about it. And yet, I was incomplete. Since I was a kid, I used to imagine my self wearing pantys, they look so cute, so girly... But didn't do it. At the beginning of this...
    John27bl John27bl 22-25, M 3 Responses Mar 31, 2014

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    Schoolgirl Dressed Me In Her Clothes Part 1

    How I became a cross dresser with a fetish for schoolgirl uniform,humiliation,small **** humiliation..Cardigan button fetish. all because of one dominant schoolgirl. my mother used to work just past home time from school so i would spend an hour or so with lady next door and her...
    rachelusissy rachelusissy 31-35, M 12 Responses Nov 6, 2010

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    Winner or Loser? Last night my wife

    and I went out with our friends. Had dinner and drinks at a local bar. After dinner some how the discussion changed and we were talking about clothes people wear. Katie said that if a man would walk around in a women's shirt in this bar people would stare however if a women...
    cdjo cdjo 41-45, M 18 Responses May 4, 2014

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