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I Am a Male to Female Crossdresser

Personal Stories, Advice, and Support 1,691 People

    So hey, interesting thing at work today.

    A graphic reminder of who I am (was?). Our local Chamber of Commerce director stops by today to drop off some flyers and we get to talking. Check this out; when I first got started in business, our Chamber of Commerce (CoC) made a run at me for membership and I joined. I could...
    JessicaDale JessicaDale 51-55 2 Responses Jan 29

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    As my wife and I were driving to her brother's

    for dinner, late of course, she began to put on her make up in the car. Then she realized that her eyeliner was mostly gone and remarked that it seemed to have gone very quickly, "unless you've been using it". I said "I've got my own, I leave yours alone ". She thanked me for...
    JessicaDale JessicaDale 51-55 4 Responses Dec 1, 2014

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    I like to dress in women's clothing,

    but tastefully. I went through a period where I very much dressed like a 15-17 year old girl, I wore tight T-shirts, "girly" clothing, and frilly things - but this version of my fem self is much more mature. I prefer skirts, tasteful tops, comfortable heels, and the occasional...
    Mich38 Mich38 36-40, M 3 Responses Nov 22, 2014

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    My girlfriend has gone out

    for the day and I am cleaning the house whilst she is out. I have decided to do it dressed up. I bought a blue minidress earlier in the week and some blue heels. I have got them on with black stockings and my favourite bra and panties. I kept the curtains downstairs closed...
    Nikki1988x Nikki1988x 26-30, T 4 Responses Sep 13, 2014

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    Hello all! I made another step today.

    I have always loved running and women's running clothes (going back to my high school Cross Country and Track days). Today I went and bought work out capri's, sports bra, and jogging tank top. I got home tried them on (still have them on actually). So tomorrow mooring I am...
    TinaCDER TinaCDER 26-30 11 Responses May 28, 2014

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    Tried my skinny jeans on today.

    ..not feeling the love.
    srqgmann srqgmann 56-60, M 1 Response Mar 25

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    Ive been this way my entire life.

    If u have seen my profile, im sure u get the point. Anyway, I just wanted to share the fact that I just increased my picture limit and its totally selfie time! Check out my new pics! ♡♥♡
    BoyNbraNpanties BoyNbraNpanties 26-30, M 8 Responses Oct 27, 2014

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    Some notes about the meeting at the Ingersoll

    Gender Center on Wednesday; I arrived early as I was unsure of the location and allowed extra time to get there. It's dark and rainy, not too unusual for Seattle, when I maneuver my new car into a pay park and start looking for others "like me". I decide to go get the payment...
    JessicaDale JessicaDale 51-55 13 Responses Feb 6

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    ..... and now I'm pushing it further,

    again. I've selected my outfit for visiting my therapist fully dressed. I chose a mocha colored sweater dress with chocolate tights and a pair of brown suede over-the-knee boots with a very low heel. My belt, boots, and purse all match. I am finishing an order with the...
    JessicaDale JessicaDale 51-55 7 Responses Oct 23, 2014

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    I'll see how the morning plays out,

    but as it stands I'm seriously considering my first trip into a retail store as Jessica today. If my dressing up goes well and my confidence is there, I think I can do it. I need some low heel black pumps or maybe wedges. I guess that we'll see how it goes. I can spend hours in...
    JessicaDale JessicaDale 51-55 2 Responses Feb 11

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    Another level of confusion : I've been

    "crossdressed" for an hour or so and I feel all of my stresses and anxieties disintegrating. I hope that somebody is taking notes on this to do a thesis on self denial.
    JessicaDale JessicaDale 51-55 8 Responses Jan 17

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    After numerous failed attempts,

    last night I finally went to dinner en femme. I am not a pretty girl and petite was never a word associated with me, ever. But..... I did it anyway. Does that give me more confidence "passing" ? In a word, no. What it does do is give me a level of self respect that I may have...
    JessicaDale JessicaDale 51-55 11 Responses Mar 6

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    I crossdressed fort many many years,

    I always wanted to go out even go dressed to go out many times, then after looking in the mirror stayed in (Man in a dress), about 3 years ago I was dressed at home and got a shock looking in a mirror that I had got to the stage were I passed, I go out now once or twice a week...
    amber8642 amber8642 56-60 2 Responses May 17, 2014

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    I Am A Closeted Crossdresser

    I am a 22 year old college student. When I was 14 years old, I discovered that one of my favorite hobbies was dressing up in women's clothing. Everyday when I got home from school before my mom or two sisters, I would try on their dresses and swimsuits while looking at myself in...
    brianschultz377 brianschultz377 22-25, M 5 Responses Nov 24, 2013

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    I did something today I have always wanted to

    do. I dressed and watched some videos on makeup and did an ok job for a first timer. Then I went for a drive which was a great feeling the way the seatbelt cut the center of my chest and getting used to driving in my heels (5 inch pumps should have started lower oh well). Then...
    TinaCDER TinaCDER 26-30 7 Responses May 8, 2014

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    take a look at my pics

    and tell me what you think. i dont try to or ever leave the house but once i tried makeup and wig for the first time I was like woooooo. holy sh*t
    MacksInner MacksInner 31-35, M 3 Responses Apr 17

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    Just a quick impromptu poll to satisfy my

    curiosity ; how many CD/TG/TS are Virgo's. Pick your label of choice and state your sign. There seems to be a disproportionate number of Virgos that are Trans ?
    JessicaDale JessicaDale 51-55 18 Responses Mar 31

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    Sitting cross-legged in a pair of nice Active

    Support Leggs, checking and replying to various messages and petting my Golden with nylon encased toes at the end of my long legs. Today will be a good day.
    JessicaDale JessicaDale 51-55 2 Responses Dec 18, 2014

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    Sorry for mis-using this post,

    but can anybody tell me how to retrieve my EP password without an Email account? I went to the mobile app a while back and forgot my login info. I believe that I used an old email address that is no longer active.
    JessicaDale JessicaDale 51-55 Feb 27

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    I'm sitting here waiting

    for this meeting to start and texting with my wife. I described what I'm wearing and she says it sounds like I "look nice and am dressed appropriately ". That sounds a little like a compliment from my wife to Jessica !!
    JessicaDale JessicaDale 51-55 4 Responses Feb 4

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    Thanks to all who took the time to derail my

    theory that there may be an environmental link to gender abnormalities LOL. My wife "accidentally" opened my newsletter from the CD club, and then accidentally read it. Now she wants to start watching Transparent with me. I haven't seen it yet, this should be interesting. There...
    JessicaDale JessicaDale 51-55 3 Responses Apr 4

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    It makes me sad to think

    that there are so many people who can't, or won't, acknowledge their own true identities. It has been a privilage to experience the joy and hardships of growing up trans. I look forward to the day that I'm able to complete the integration of my femme self into the life that I've...
    JessicaDale JessicaDale 51-55 6 Responses Mar 2

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    Hi M, I know that you

    and Mom talked Thursday night about where I was and what I was doing. Let me first say "Thank you " for being so understanding and agreeing to be a resource for Mom, it means a lot to both of us. You probably have some questions and I will do my best to answer them. You...
    JessicaDale JessicaDale 51-55 6 Responses Dec 8, 2014

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    I was a teen when I discovered I liked the dark

    lash look that mascara gave the user. I asked an older neighbor girl, her makeup was always immaculate and tastefully done, if she would put some on me. She smiled and granted me my wish, I now had upper and lower lashes coated with black mascara. Didn't take long for me to...
    CdKimmi CdKimmi 66-70, M 3 Responses Aug 14, 2014

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    Just started dressing again I have to say I

    wish I would of never stop I wish I could look beautiful every day and be able to be who I want to be and that's a girl with a penis
    Rachellee1217 Rachellee1217 26-30, M 4 Responses Sep 2, 2014

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    I love to wear sexy panties with maxi pads.

    Am I strange or is there anyone else that likes to wear maxi pads too?
    jmitchelljm2 jmitchelljm2 66-70, T 1 Response Feb 5

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    I was just organizing my gurl stuff

    and took a quick inventory: 9 pair of boots of varying styles, 7 pairs of pumps up to 6 inches tall, 2 pairs of ballet flats 6 pairs of sandals Breastforms, padded girdle, wigs, makeup, purses, sweaters, jeans, bikinis, stretch pants, tights, a dozen or so dresses, etc...
    JessicaDale JessicaDale 51-55 9 Responses Jan 1

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    I'm feeling more and more

    that I should begin posting in the I'm Transgender thread, but at the same time I'm feeling stuck. I need a push but I have our 25th wedding anniversary coming up. We have a trip to Orlando booked that I don't want to ruin by letting my impatient little inner girl run rampant...
    JessicaDale JessicaDale 51-55 2 Responses Feb 25

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    Hi everyone! I enjoy dressing up in woman's

    clothing and getting all dolled up. It's a very fun activity for me and I find some nice clothing that I like to wear even when I don't get dressed up. I find that wearing boy short panties are extremely comfortable and are also great to sleep in, and I enjoy wearing fitted...
    BridgetWatson BridgetWatson 18-21, F 10 Responses May 26, 2014

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    Life continues to tease me into a sense of

    being able to live externally the way that I feel internally. I have very few close friends, they scare me. They're a threat to my secrecy. One of my few friends is the total manly -man type of guy. He's the hunter, fixer-upper, let's go golfing type. Stereotypical guy that I...
    JessicaDale JessicaDale 51-55 4 Responses Feb 24

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    I have an online master now

    and am looking for more.
    John69large John69large 41-45 Apr 20

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    Call me crazy, but a part of me almost wants to

    tell my older sister that I love crossdressing. Be like, "you know why I get all weird when you ask to use my pick up truck?, it's because I have a huge box in the back seat full of tops, dresses, skirts, leggings, bras, breastforms, make up and high heels,
    JessicaCD20 JessicaCD20 18-21, M 3 Responses Sep 27, 2014

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    I tried on a cute dress this morning,

    was hoping it would fit but wouldn't zip...dam broad shoulders.
    srqgmann srqgmann 56-60, M 2 Responses Feb 9

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    been one all of my life ad

    as of late I have sex with other crossdressers and good looking men-
    xkimm xkimm 61-65, M 4 Responses Feb 11

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    People Ive Told Im A Mtf Crossdresser And The Stories!!

    Well for starters my instagram is Girlyautumn and whoever remembers me from a while back in November on here as AutumnCD is awesome but here are my stories. -Step mom So one night I think in November of 2012 I was wearing some of my step sisters clothing in the bathroom. I was...
    Girlyautumn Girlyautumn 18-21, T 6 Responses Nov 18, 2013

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    It would appear that I'm done hiding from the

    neighbors. I believe that they want to be left alone and if anything is said about the new gurl around the house, they will not be left alone. I do not expect to hear a single word, even if they recognized me .
    JessicaDale JessicaDale 51-55 3 Responses Feb 25

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    No pant legs to wipe my hands on

    and no pockets to put stuff in. It's no wonder that fewer and fewer women wear dresses. Next time I'll bring an apron LOL.
    JessicaDale JessicaDale 51-55 1 Response Feb 4

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    I first crossdressed

    as a teenager, I have no recollection of desiring to crossdress pre teenage. My initial dressing was in knickers (panties), and as teenager I always wanted to wear a suspender belt and nylon stockings, tights(pantyhose) were not available in those days, it was only in the 196...
    MandytgAndy MandytgAndy 70+, T 6 Responses Feb 25

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    I'm in a restaurant having a Lemon Drop

    and waiting for my salad, dressed in women's clothes !!! I did it ******* !! I'm frickin doing this, right now. Been texting my wife along the way, so far, so good.
    JessicaDale JessicaDale 51-55 7 Responses Mar 5

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    Welcome back to Jessica's blog,

    LOL. Things have been pretty quiet since before Xmas and my inner girl is getting restless. Putting all of my CD/TG stuff on hold has produced mixed results for my relationship with my wife. It has definitely not helped me be a better spouse. But at least now I (we?) know...
    JessicaDale JessicaDale 51-55 12 Responses Feb 3

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    Wow

    I have always had a fascination with feminine clothes, the sexier the better, and heels not under 3 inches! I started sampling wearing them in my teens from my sisters wardrobes and immediately knew how much better I felt about myself when I looked in the mirror and saw this...
    Candicegirl Candicegirl 51-55, T 10 Responses Aug 16, 2012

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    I love everything about crossdressing.

    The hair, makeup, high heels, fem undi things. I feel happier when dressed.
    susiecdgurl susiecdgurl 56-60, T 3 Responses Jul 5, 2014

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    My wife came home last night to find me fixing

    an amazing meal for the two of us. I was wearing an oversized shirt (it used to fit me!) over some tight black long underwear (stretch pants? ) and a pair of long wool socks scrunched down. I think that she could sense my contentment. She said that I "looked cute ", I nearly...
    JessicaDale JessicaDale 51-55 3 Responses Dec 12, 2014

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    I just came home for lunch

    and can't seem to shake this bizarre feeling of having been in a long day dream at work today. It feels like what I might imagine a disociative identity disorder might feel like. It's very bizarre and feels sureal. It's a little perplexing. And even after I acknowledge the dream...
    JessicaDale JessicaDale 51-55 4 Responses Jan 26

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    I guess when you find something

    that works, it's best to go with it. I spent yesterday afternoon wearing an "outfit " very similar to the one that I was complimented on by my wife last week. I did some housework, put up some Christmas decorations, and fixed a dinner and salad that earned me a "Holy Crap, that...
    JessicaDale JessicaDale 51-55 3 Responses Dec 17, 2014

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    Had anyone had enough of my shenanigans yet?

    My latest action item on my therapy list is to open up more with my wife about my feminine needs. So awkward. The subconscious mind is very tricky and deserves tremendous respect. I've had some quality alone time several nights this week, my wife does this to help meet my...
    JessicaDale JessicaDale 51-55 5 Responses Feb 28

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