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Why crossdressing is an amazing way to let your feminine side out and to celebrate your gender ambiguity!

I’m a 23 year old crossdresser from the US. My “hobby” started when I was 4 years old. I sneaked into my sister’s bedroom to play hide and seek and I found this dress spread on her bed. I had this unexplainable urge to close the door and to put the dress on. It felt exciting and unexplored. I looked in a mirror and felt so cute when I saw myself in this retro dress. I would continue doing this over the next 10 years every time my sister wasn’t home. She’s 3 years older than me. When I turned 15 she left for college where she stayed in a sorority. She left a lot of her clothes behind during the week, so I had an excellent occassion to try them on. The excitement that I first felt wore off after several years of doing this almost daily and it made place for an urge that caused anxiety when left unfulfilled.

When I was 16 I started growing my hair out. I didn’t only wanted to get dressed up indoors, I also wanted to be more myself outdoors. I started ordering special conditioners and more delicate shampoos that contained etheral oils and argan oil. At the same time I discovered how important skin texture is for a woman. With a manly, oily skin I would never make a pretty girl when dressed. So I started moisturizing and exfoliating thrice a week. I also started applying tea tree oil to my skin daily. Soon, I started to get brighter skin and a more relaxed sense of self.

Over the next years I never got a hair cut and my hair started getting longer and longer. My skin was soft as a woman’s skin. I shaved twice daily and I started consuming hops flowers which contain phytoestrogens, herbal forms of estrogen-mimicking compounds. My nipples started getting more sensitive, my areolae started getting puffier and I developed two small discs under my nipples on each side of my chest. In a matter of a year and a half of consuming hops flowers every day, I developed a little under a full A cup. I now had a reason to start buying Victoria Secret bralettes and panties. The fabric of women’s underwear feels so much better than the fabric of men’s underwear.

I also started painting my nails with clear polish and having mani-pedis regularly.

At 21 I had my first girlfriend. She is a bi girl so she didn’t mind me being feminine. When I met her parents for the first time they could hardly tell I am a guy.

Over the year and a half I have started waist training. I have now developed an hour glass figure. I do squats for a bigger butt.

We went to an exposition last month and one guy grabbed my bum without realising that I was a guy, till my girlfriend said ‘he’s mine already’.

I have become the sissy that I have always wanted to be.

Me and my girlfriend can afford our own place because I escort. Last week, I got fucked by 15 clients which averages over 2 a day. Most are married men who love ‘chicks with dicks’ .

At my job no one knows. I do regularly flirt with male colleagues. My girlfriend loves to see me being devored by a real man, while she watches for her pleasure.

Most of my clients come for getting a good blowjob.

My crossdressing has allowed me to let my gender ambiguity out. I now get to live as both a guy and a girl.

The sex with my girlfriend is also much better. We have lesbian sex and straight sex. Sometimes I fuck her like a macho man, sometimes I fuck her like a kinky lipstick lesbian. I love it when we suckle on each others nipples while I rub her clitoris.

Life is good!

Hope my story served for some other feminine boys / girls and those who love to admire and date us.

Why crossdressing is an amazing way to let your feminine side out and to celebrate your gender ambiguity!
Why crossdressing is an amazing way to let your feminine side out and to celebrate your gender ambiguity!
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Most Helpful Girls

  • VaIiant

    Bullshit on this entire story:
    1. No man can develop an “hour glass figure”, especially without taking prescribed, serious estrogen hormones. A year and a half is DEFINITELY not enough time to do so, especially not if originally you had a mans figure.
    2. Bullshit on the fact you’re a prostitute- 2 a day? BS.
    3. The fabric of women’s underwear does not feel better. I have worn both my own, and my boyfriends underwear when I woke up. Also- women’s underwear will NOT fit a penis.

    • ret04

      Yes they can. Forget what it's called, but there are these binders a person can wear over time to shape and make their waist much smaller. It works like those things people wear in some cultures to make their necks skinny and long. Also, satin definitely has a more pleasant feel than cotton and yes, the male genitals are more flexible than you think.

    • VaIiant

      @ret04 Waist trainers will not give a man an hour glass figure. Also, studies have shown your body will not hold the form.

    • I am taking hormones, herbal hormones @Valiant. They are just as effective as prescribed hormones. Look for studies on the phytoestrogen 8-Prenylnaringenin. It’s the strongest plant estrogen ever found. My testosterone has gone down while taking this and I have experienced breast growth and fat redistribution to butt and hips. So I don’t know why you call my experience fake when you have no reason to.

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  • Cold_hearth

    I don't understand why girls can wear pants, suits, ties, basically everything a guy wears and be seen as "strong" "empowered" "sexy" but when it's a guy wearing remotely girly he's "crossdressing" tf is this double standard?

Most Helpful Guys

  • Wow that's some fuckec up shit you can't be telling the truth how the fuck have you got a girlfriend your sucking guys cocks as an escort and you've got a girlfriend who's alright with that your dreaming if it's true that's one of the most fucked up deranged stories I've ever heard wow.

  • DashboardLight

    Fam, I don’t need to know your fucking sex positions you use during sex. Jesus Christ.

    This is not stimulating anybody to cross-dress. Your story is kind of screwed up. I don’t think people would want to have a life like this. But whatever, you do you...

What Girls & Guys Said

  • AuroraRoseat

    I am happy that you know who you are and fully embrace yourself (assuming this isn't a joke made by someone). Don't listen to the ignorant individuals that spew hate simply because they lack awareness and understanding. They are why society is so poisonous.

    Continue living your life the way you wish and know that there are plenty of people who support you. :)

  • Vane325

    I am happy your happy and that you found someone that understands you and loves you for who you are. To be honest though the escort thing took a 180 degree. I couldn't date anyone that was doing that I would get jealous and worried about diseases ( please get checked regularly for yourself and your girlfriend health). Also the comments some guys left on this thread is disheartening.

  • FreshOutaIdeas

    More freaks to be disposed of in the trash can of human history. You subversive degenerates are running out of time with all your agenda oushing...

    60 years ago we had mental asylum's and the rope for people like you, 2000 years ago you wouldn't have existed at all, worst case you would've been discarded in the bog at a very young age for being as dishonourable as a man could be.

    I don't want to have my kide grow up in a society full of (((degenerates))) like you.

  • SexyAshh

    Not into transexuality nor is almost 95 percent on this site so goodluck.

  • Ordinarygurl_

    Interesting i think ur really brave i hope that people don’t bring u down

  • Kas19

    If that picture is you, you're really pretty! I'm happy for you :)

  • No_Archons

    ... I don't like men dressing like women, it's confusing for the straight man's mind. That being said, ur not hurting anyone, so do what u want, but I would not hang out with u

    • Aw. The fragile heterosexual male mind.

    • No_Archons

      Fragile in. some. ways like all things, strong in many ways tho. It is hard to stay in touch with reality when. everyone around. you. descends. into delusions

    • That is deep. And sadly true.

  • DakotaNorth

    It wouldn't work for me. I had to transition. Now I'm a woman 24/7 and I like it like that.

  • If it's anything like this I won't mind

  • lordgrifis

    As a bi man and, sometimes, wishing-to-be-sissy, i congratulate you in being what you wished for.

  • ShadowofRegret

    This is rather disturbing...

  • esotericstory

    Androgynous men and women have a bad effect on natality.

  • Look I'm been cross-dressing longer them most been alive on here.

    I have to say there is a part you left out.

    There is many stages of cross-dressing
    Like me. I have no desire to be or look feminine or be female.

    I have a big bruly beard, big manly arms, and have a deep voice like Berry White.

    I just so happen to like women's clothes more. I like being a man, looking like a man. Just I'm in women's clothes.

    I'm the manlyist crossdresser you ever meet and have no problems kicking the shit out of people. Who challenge me or insist calling me a sissy.

    • JackSmy

      So why post anonymous? Love your post, and nothing wrong with wearing women's clothes, as they wear 'Men's' clothes, all the time!! "Boy-short' panties, and pants? Who cares!
      Open-minded people don't even think about this kind of thing, as it is so normal, and just assumed!
      How does it really matter if some guys like soft, cotton women's panties, and the soft fabric, or maybe other things, with a partner, that likes the same?

    • @JackSmy Okay Jack, now you see it is me. I went anonymously because I had a similar question out there and I didn't want a bias opinions.

    • JackSmy

      Cool, good to meet you!! Didn't mean to imply any condemnation, but so many post anonymous, when they have a valid point, and are expressing something of value to many others, here. Maybe anonymous helps so you don't get a barrage of personal messages, if you don't want that.
      I just hate that so many people here, posting totally normal things, get so much sht from haters and trolls. Some are personal, as I have friends, or relations in some of the same lifestyles.

  • GiaQuebecoise

    Put your dick wherever you want, just keep it out of my sight. Thanks.

  • Anjali090

    I don't agree with this. Men should be men and women should be women.

  • MoneyBeets

    Why would you want to be a woman? Being a man is much better, than mentally ill.

  • Lawschoolgossips

    If that’s you you make a pretty lady. Be careful with escorting though. Sex workers have a higher probability of getting killed, raped or robbed.

  • Melshmallow046

    That's messed up...

  • This is Sodom and Gomorrah. Repent or perish.

    • Agape93

      Was that a threat, nazi boy?

    • @Agape93 : It is God who threatens from His word.

    • Agape93

      Your god is too weak to do anything to them. Or anyone for that matter.

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  • LuvAsh


    • Yeah God made us all a certain way and there's people who want to be something they're not

    • LuvAsh


  • TheAmazingAmerican

    That's gross as hell. You need some help bro

  • Agape93

    Do what thou wilt

  • QooLipBite

    Boarding the nope train

  • That's disturbing and satanic. No contest

  • EmmaMary

    Yet another Guy In Disguise! smh

  • Vesta

    So you became a preop trans basically

    • No. For that you usually need a whole lot of dysphoria. This guy seems fine with male framework and enough femininity to keep from going crazy. More along the ines of gender fluid from the sounds of it.

    • Vesta

      Nope, it just seems he became a pre op trans

    • DakotaNorth you are not exactly a looker yourself, so who are you to tell what other people are or aren’t?

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  • bangyourhead

    So you’re a gay man.

    • Many male crossdressers are gay, that's true. Not all.

  • FragileSnowflake


    Can we not?

  • Anonymous

    I think you do you, and if that's what you enjoy go for it!!

  • Anonymous

    I wouldn’t go that far, but cool and good for you.

  • Anonymous

    That is a lovely thought... congrats on the complexity of it

  • Anonymous


  • Anonymous

    My older brother is like you.