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I Am a Straight Male Crossdresser

Personal Stories, Advice, and Support 761 People

    I'm dating a crossdresser.

    I'm trying to learn how to accept and support him. We haven't been dating long and he's never dressed around me. He hasn't dressed since his divorce 2 years ago. Sometimes I'm excited to explore this with him and sometimes I get really freaked out. Your stories are helping.
    CarneyVorous CarneyVorous 26-30, F 12 Responses Jan 20

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    The Christmas Holidays always remind me of my

    childhood, and my childhood always had a bit of fantasy involving crossdressing. I remember my girl cousins would wear their pretty dresses and tights and shiny black shoes. I wanted so much to be a pretty girl and wear those things, but it was never to be. Yes I have been...
    1SarahAnn 1SarahAnn 46-50, M 5 Responses Dec 24, 2013

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    How Can We All Come Out?

    I just read yet another story complaining that crossdressers are automatically assumed homosexual or transgendered. The problem is, there are several reasons for crossdressing. Gays and transgendered usually have less to lose and are not hiding, while we "otherwise straight...
    tightsvirus tightsvirus 41-45, M 2 Responses Sep 5, 2013

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    Unhappyman

    Iat one time dressed as a woman and drove around town. This was such a big steo for me but unfortunately my wife came home so it was just a time thing. My ultimate goal is to be able to get enough things together and go out in public dressed as a woman anytime i feel like it! I...
    jimmyphillips1957 jimmyphillips1957 56-60 2 Responses Apr 25, 2011

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    Yesterday I cried yesterday,

    not a hard satisfying cry, but small sobs, the kind that struggle to come out against your will. I didn’t think that I would cry, it caught me by surprise, but not as much as the violent shaking that shook my body as I talked. I even wrapped my feet around the chair legs, and...
    1SarahAnn 1SarahAnn 46-50, M 1 Response Feb 10

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    fercrox fercrox 46-50, M 1 Response Apr 6

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    My Early Crossdressing Memories

    My earliest memories of wanting to be a girl were in kindergarten. Girls still wore dresses to school, and I wanted to wear a dress. To me then, a dress symbolized being a girl. I didn’t know the difference between boys and girls at the time, but I knew that I wanted to wear a...
    1SarahAnn 1SarahAnn 46-50, M Jun 20, 2013

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    My Crossdressing Life-the Present

    I met my wife seven years ago in late September on one of the large Internet dating sites. It was my last week on the site, as I had no real previous luck in meeting anyone that I thought would accept me into their lives. It was her first week on the site. So maybe it was fate...
    1SarahAnn 1SarahAnn 46-50, M 4 Responses Jun 20, 2013

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    The Grey Area

    I am 16 years old and I have always thought of me as straight for the few years I have crossdressed, but now I'm not so sure. Lately I have been having thoughts of men and reading crossdressing erotic stories and I dont know why. It feels weird but also right. I'm at a tough...
    everydaynormalguy everydaynormalguy 16-17, M 2 Responses Jul 16, 2012

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    Here I Go Again Saying It,i Am Straight

    This story is not intended for all gays or Bi's.I am sorry if i offend someone.Again i do not mean this for all.I got another comment that i had to be gay or Bi because i wear panties.This from persons who are gay or Bi and it's not the first time from someone.I have come to...
    cindyloulove cindyloulove 56-60, M 13 Responses Jan 23, 2012

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    Why I Crossdress

    I like the colors the selection and it makes me feel sexy and naughty. When it comes to womens clothes they seem to have a ton of color while men are stuck blah colors like black and grey women have way better selection and i can show off my body more in womens clothes.
    ryenmatt ryenmatt 36-40, M 2 Responses Dec 27, 2012

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    I Found Someone Who Loves Me Despite My Cross Dressing

    I am a recovering crackhead, and cross-addicted alcoholic, and so I am a member of Alcoholics Anonymous. After 3 years of coming to meetings as "Joe" (not my real name), I chose Halloween as my day to come out, at a noon meeting, and told my story of drinking and drugging with...
    joseygurl23 joseygurl23 56-60 19 Responses Sep 11, 2013

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    My Crossdressing Life-my Twenties And Thirties

    My twenties found me with a mix of crossdressing opportunities, and failed relationships. It was not until my mid-twenties that I found a sweet woman that seemed very open-minded. She was a bit of an exhibitionist, and had a foot fetish. She had some gay friends, and I thought...
    1SarahAnn 1SarahAnn 46-50, M Jun 20, 2013

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    Cross Dressing With My Wife

    Tuesday was a very hard day at work so when I got off I need something to made me feel better. I went to a department store to look at dresses. I had seen a dress there I liked in my size on the discount rack but I had put a limit on myself of no more then $25 for the dress and...
    mat2Robin43 mat2Robin43 51-55, M 5 Responses Oct 4, 2013

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    2013 Crossdressing Review 2013 was an

    interesting year in crossdressing for me. My wife and I spent many hours as two women in public, but I wanted to feel a little more feminine, to experience being a woman while dealing with people in public. I wanted to face a wider variety of people, yet, I wanted to somewhat...
    1SarahAnn 1SarahAnn 46-50, M 2 Responses Feb 7

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    Im starting crossdressing any old dress skirt

    wigs shoes will b a big help i can pay for post if u wish
    crossdresskatie crossdresskatie 22-25, M 4 Responses Dec 8, 2013

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    Partially True For Me

    I consider myself pansexual rather than straight but as pansexuality encompasses all orientation, I can safely be part if this group. I am just a light crossdresser who's into wearing panties, leggings and yoga pants. The common thread of all these articles of clothing being...
    TrulyBiGuy TrulyBiGuy 41-45, M 3 Responses Oct 24, 2013

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    I'm Straght Too Am I The Only One????

    Ok here it goes, I like to dressup... been doing it for years.It feels good and calms me down.It releaves my stress and at the same time causes stress because its tabo to society.Ill explain, I can never tell a girl because she will leave me.Women do not accept this so I must...
    lisaree13 lisaree13 41-45, M 56 Responses Sep 4, 2012

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    Dress To Impress - Bbc Television Program On Youtube

    Wanted everyone to know that Dress to Impress, a BBC television story (fiction) about a teenage crossdresser and his family, is once again on YouTube http://www.youtube.com/watch?v=d8kdwIN5kC0 I don't know how long it will stay this time (I suspect there are copyright...
    lindamariedaniels lindamariedaniels 56-60, M Dec 18, 2012

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    My Profile Picture

    I looked very similar to this boy when I was young. I found this picture at an antique store a few years ago. It was sitting in a pile of other pictures. I'm no expert but I would think that its from the 1940's or early 50's, based on the paper size and quality. I wish it was...
    1SarahAnn 1SarahAnn 46-50, M 2 Responses Jun 22, 2013

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    My Crossdressing Life-epilogue

    When I was a young teen, I called a helpline for people that needed to talk about issues. This was about the time that I realized just how different that I was, and that there were possibly others just like me in the world. I remember talking to an older man, who listened to my...
    1SarahAnn 1SarahAnn 46-50, M 2 Responses Jun 20, 2013

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    Single Lady

    Finding it really hard to meet a straight crossdresser :-/
    6 Responses Jan 14, 2013

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    The Scarest Moment Of My Life

    So just to begin, I have to say I am married to the most wonderfull, beautiful, understanding woman in the entire world. I am so deeply in love with her so much more now than I could have ever imagined. Ok, so recently I came out to my wife. This was the hardest and...
    mattie76 mattie76 36-40 1 Response May 19, 2013

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    Things have change so much

    since my partner found out about my crossdressing.... Monday (My day off) my partner left for work at 8am leaving me a list of task to be done that day, I showered put on a denim skirt opaque tights ans pink top and hair and makeup, spent the day cleaning, cooking and washing...
    amber8642 amber8642 51-55 9 Responses Feb 26

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    My Crossdressing Life-the Future

    In my opinion, crossdressing is similar to a drug addiction, in that it appears, (at least with me) that you need greater stimulation to keep yourself satisfied. I don’t know any other crossdressers personally, so I can’t say if this is universally true. My needs have changed...
    1SarahAnn 1SarahAnn 46-50, M 1 Response Jun 20, 2013

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    Straight Teenage Cross Dresser

    I am straight but found out tht I love to cross dress, I was at the mall with my gf and she made me try on some booty shorts and then a bikini and since then I was hooked. She is very supportive and supposedly finds it super sexy. The only problem is tht I am very religious and...
    Jason123u854 Jason123u854 18-21, M 10 Responses Oct 31, 2013

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    I went shopping yesterday bought a great gold

    dress for Chritmas day, What are you wearing ?????????
    amber8642 amber8642 51-55 4 Responses Dec 18, 2013

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    i want cross dress as a female like all the

    clothes,have long hair, makeup, jewelry and everything and also learn the ways of women. even how to do sex. plzzz message me and help me out any girl in dubai who would help me and support me
    shifakhan shifakhan 18-21, M Apr 12

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    So I'm very new to this.

    I tried on my mom's bra/panties/pantyhose/dress for a dare and it felt pretty good. Don't misunderstand me, I'm not a crossdresser. I posted a pic anon online (without my face) and had many guys over me. Some problems: hands not slender, shoulders too broad, hips not broad...
    corneliousrodriguez corneliousrodriguez 22-25 2 Responses Feb 3

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    Interesting Times

    For as long as I can remember, I have always had the deire to dress myself in women's clothes. My earliest memory of this was a time when I was probably only 5 years old. My female cousin was staying over our house for a few days, and her bag of clothes was left in my room. When...
    AndreaLynn AndreaLynn 36-40 2 Responses Oct 13, 2008

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    66 Years Old And Still Crossdressing

    It all began when I was about 12-13 years old.  My parents would play cards one night a week and that was my night to put on some of Mom's lingerie and to play.  I found that I loved the feeling of slinky panties and, for some reason, having a bra on has always been the real...
    DonS11 DonS11 66-70, M 8 Responses Sep 14, 2011

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    Hello, my name is Shannon,

    I am a male to female crossdresser, I am 37 and live with my 2 children, I crossdress 24/7, although mostly concealed when I take kids on school run, all the main people in my life know about me and accept me, or have kinda known all a long I was, I have been crossdressing since...
    shannoncox shannoncox 36-40 4 Responses Dec 16, 2013

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    Doing A TV Documentary

    Hi everyone! Please message me if you are interested in being part of an inspirational documentary about people whose true selves challenge society's narrow gender norms. I would love to hear from you. email h.golden@mavericktvusa.com. We are looking to tell real, emotional...
    maverick567 maverick567 31-35 Mar 22, 2013

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    My Crossdressing Life-the Teen Years

    My high school years were very typical for a young man, cars, football games, parties, and girls. Not a lot of girls, but enough to know I liked them for more than just the clothes that they could wear. I was involved in sports, and began to weight lift and gain muscle. I wasn...
    1SarahAnn 1SarahAnn 46-50, M 1 Response Jun 20, 2013

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    Nice To Be Amoung Friend.

    I have read many stories here and I share others frustrations. I've always wanted to have a close friend who sharred my interest in crossdressing. Not someone to have a sexual encounter with or even someone to play dress-up with. Just a close friend you could talk to about...
    silkydrawers silkydrawers 46-50 2 Responses Oct 7, 2012

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    hey i love crossdressing

    and people who crossdress so kik weshouldtalk098 and we can talk and exchange pics or add sissyboy019 in snapchat to talk i like both guys and girls btw 
    weshouldtalk098 weshouldtalk098 18-21 1 Response Jan 4

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    Feeding The Cat

    My friend who is a girl asked me to feed her cat I agreed and in her house I couldn't resist the urge to go to her dresser and closet and wear her things and bras and dresses. I fed the cat for 3 days and this was an amazing 3 days. Eventually I read online you need to tell a...
    Superguy4 Superguy4 13-15 4 Responses Jul 24, 2012

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    Always Have Been And For Ever

    I've dressed since i was around 8 years old.It's hard to remember.I am straight and not interested in guys.I don't know how else to say it or how many more  times i have to say it.I am STRAIGHT,STRAIGHT,STRAIGHT.I am happily married and yes to a real woman.That's all i do,dress...
    cindyloulove cindyloulove 56-60, M 4 Responses Nov 12, 2011

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    Finding Myself Amongst 100's Of Teenagers

    When I was young around 8 years old, my big sister told me she would give me some money to wear one of her dresses, $2 later (I was naive and thought it to be worth it) I was in my sisters dress, and it was comfortable, and it made me feel pretty. I tried to forget about it for a...
    CrimsonOokami CrimsonOokami 18-21, M 2 Responses Sep 27, 2013

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    A Day In The Life Of Sarah Ann

    Its 7:00am on a cool overcast Sunday somewhere in the Midwest. I’m up before my wife, showering and getting ready for a day out as Sarah Ann. I spent the night before soaking in the tub and carefully shaving every part of my body. This morning I’m just going over everything...
    1SarahAnn 1SarahAnn 46-50, M 3 Responses Jun 20, 2013

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    Volunteer Day This past Saturday was probably

    the most feminine day of my life. I was wearing my favorite brown plaid jumper with a black turtle neck, black patterned tights and black wedges. This particular jumper is a bit shorter than usual and ties in back . It feels so pretty. My hair and makeup came out very nice, and...
    1SarahAnn 1SarahAnn 46-50, M 1 Response Feb 17

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    New years Eve 2014 I have always been a little

    envious of the ability of women to go out during the holidays wearing such pretty clothes, makeup and shoes, especially on New Years Eve. So my wife and I have been going out for the last two years for our New Years Eve celebration to a city about two hours away. This year we...
    1SarahAnn 1SarahAnn 46-50, M 3 Responses Jan 1

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    And Am Finding Blogs For People Like Me...

    ...who are not out of control with their cross dressing. Where there is balance in the lives they lead. Loving, devoted husbands, who don't want to share their wives, who are caring fathers, and who do not focus on sexual pleasure at every turn, and who practice discretion. Who...
    joseygurl23 joseygurl23 56-60 8 Responses Oct 13, 2013

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    Related Experiences

    Please contact me via EP, my Facebook page under Jess Angel or JessAngel6y@gmail.com to join our new male Christian Crossdressers group. I'm looking to generate support for each...
    JessAngel JessAngel 22-25 1 Response Apr 5

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    i want an indian women or girl in dubai who can dress me up as a bride. put makeup on me, dress me up, put bangles, saree, bindi mehndi and all. plzzz any indian women or girl...
    shifakhan shifakhan 18-21, M Apr 12

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    If there any girls here willing to add me or help with a 0% chance of girls clothes for me to wear or you wanna be friends please message me i am a male crossdresser and by the way...
    lovepink73 lovepink73 13-15, M 1 Response Mar 22

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    I am a straight male been with women all my life but lately I noticed I have a desire and it is to suck/worship a mans p@en%is and more of a desire to have a black p *e&ni*s in my...
    davillian92 davillian92 18-21, M 1 Response a week ago

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    I've always loved the idea of dating a crossdresser. I'm what some people might call a "tomboy" and I just always found the juxtaposition ( I that's the right word I'm not really...
    BrahmaDonna BrahmaDonna 22-25, F 16 Responses Mar 22

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    So, that kid I have in my circle commented on one of my stories here which reminded me of this old group I have forgotten! This group has reminded me of a conversation I had...
    MissGaga MissGaga 22-25, F 1 Response Mar 26

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    So today I went shopping, got some jeans, sweatpants and some shorts for the male side and some tight exercise shorts for my female side. I did some butt workouts in them and felt...
    DanielleSweetcheeks DanielleSweetcheeks 18-21, T Apr 12

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    I am straight. Straight up gay.! Haha I actually don't know. Sometimes I think I just start catching romantic feelings for any individual that I'm in close contact with often...
    Kasney Kasney 16-17, F Mar 25

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    My boyfriend and I have been dating for over a year now, and I am completely in love with him. He' my best friend and the love of my life. I can't imagine life without him. He...
    lithium123 lithium123 22-25 6 Responses Mar 30

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    I am falling for a crossdresser. I love him and who he is and I would never change him. I told my family, which consist of my mother and sister. Mom was accepting, my sister was...
    bbsw1963 bbsw1963 46-50, F 2 Responses Mar 24

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    I absolutely adore crossdressers. I kind of run a small business where I help boys and men get dressed up. I would love to hear all of your stories. Any age can message me, and I...
    ShainaNichole ShainaNichole 18-21, F 12 Responses Mar 29

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    I live in GA and would like to meet other crossdressers and transgenders.
    sexidancer sexidancer 41-45, T 2 Responses Mar 30

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