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!
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What Girls & Guys Said

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  • Uhhhhh

    Can we not?

  • 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.

    • 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?

    • Show All
  • Androgynous men and women have a bad effect on natality.

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

  • 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.

  • That's disturbing and satanic. No contest

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

    • Again fuck you you piece of shit. It Seriously people like you that disgust the hell out of me. He's not hurting no one! He is doing what he loves! Fuck you for saying mentally ill, you're the one who's mentally ill for thinking like that. Go fuck off man

  • My mistress loves to dress me up as a sissy girl and invite her dominatrix friends over I love it

  • I really want to become a shemale some day.

  • You are very lucky to have the life you have and your girlfriend is a goddess to let you have all of that!!

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

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

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

  • Yuck

  • My older brother is like you.