Crossdressing Storieslatest

The Most Feminine Side

feminine sideHi, this is my story and since I was little I have always been curious about women’s clothing, it all started when I was about 8 years old. The first times I used feminine articles were for challenges, and I had mixed feelings about it, I could feel the adrenaline, I thought it was for the challenge but later I realized that it was for something else.

I have a little sister and when no one was home, I would wear her clothes, and since she was a little girl she had princess dresses, so those were one of the first clothes I wore. Seeing myself as a sweet girl caused me a strange pleasure, but little by little I climbed to do more interesting things.

A short time later I tried my mother’s makeup, as I was a little girl I didn’t know how to use it so well, I only put on a little red lipstick but it was enough to make me look pretty. On a couple of occasions they were close to catching me dressed, or wearing makeup due to my carelessness and although I invented excuses that got me out of trouble, I’m sure they already had an idea of ​​my tastes.

For the same fear of being discovered, I stopped dressing and promised not to do it again (as if I could really do it) but some time later the desire returned. This time with a little more time alone at home I was able to experiment with more things, I did a complete makeup based on tutorials that I had seen, and the truth is it turned out quite well than I expected.

Similarly, I wore women’s underwear for the first time, beautiful bras, sexy panties and tight leggings. I even found a sexy lingerie that I did not hesitate to wear. The truth was it was exciting to feel the clothes between my intimate parts, being able to touch the soft fabric of the panties is simply fascinating.

To simulate boobs, I stuffed my bras with my socks and I loved how my beautiful round breasts looked, even though they were fake I felt like a real girl. That was the opportunity to wear party dresses, swimsuits, skirts, etc. My sister and mother’s wardrobe was limited, I wanted to be able to try on something leather, some sexier skirt, even if it was a wig, but even without these things, I was happy to dress up.

On one occasion I was so excited that I felt liquid dripping abundantly between the panties I was wearing, I got scared and fixed it as fast as I could, but that has always been a problem when wearing clothes that are not mine hehe.

Over time I took photos of myself dressed and the truth is that I looked quite beautiful, I did not recognize myself in the mirror as a man, but as a beautiful girl. It was always a chaos to put everything back in its place so that they would not suspect what I was doing, (I am more and more discreet with that) but it was worth it.

-Note: For those CD girls who are just starting out, I recommend putting some cloth or paper in their intimate areas so that when the inevitable happens they don’t stain their clothes in case it’s not theirs, that or wearing underpants underneath, although it ruins the experience of having a panty on.

It wasn’t until high school with a friend that my feminine personality took on more strength, as always it all started with a “challenge” in which if I lost, I had to dress from head to toe as a girl, obviously inside I was dying to do it, but I acted like I didn’t.

My friend was planning everything she was going to do with me and I was giving her ideas of what she “wouldn’t want to do” for her to consider. Among those things that she planned, she told me that I had to have a female name, to match the male name, she called me Jennifer, at first I felt weird and I rejected it, but then I fell in love with the idea.

One day while at her house she told me that she would still fulfill the bet, and that I had to dress as a girl at that moment, she took me to a salon where they put on my makeup, but at that moment more people began to arrive, which made me feel uncomfortable and nervous, when they finished my makeup and we went back to her house, my worry and stress was so much that I collapsed and told her that I couldn’t continue with that, (I know, let one of the best opportunities pass of my life but I couldn’t handle the pressure of being seen by so many people).

In the end all that happened and it only remains as an anecdote, at that time I did not know what crossdressing was and I thought that what I was doing was bad and embarrassing, I did not tell my friend my tastes, I thought it was something too strange to tell others.

At home I had less and less time alone to be able to dress as I wanted. But at night, thanks to the internet, I started watching tg videos, makeup videos and things like that, so I was never that far from Jennifer. Over time I tried more women’s underwear, and more elegant clothes, although it was more difficult because I was getting bigger and some clothes stopped fitting (I even ripped some clothes because they were too small for me), and that’s how I’ve endured several years.

But just doing research I realized that my tastes were more common than I thought, cross-dressing was something that many people practiced, that made me feel relieved, being able to see such amazing transformations has inspired me to one day do something like this. I was also able to find several sites that offer prosthetic breasts and lady parts that I obviously want to get (they are a bit pricey so it will take me time to save up).

I realized that my wishes to be Jennifer are not bad or strange, it was until recently that I faced myself and promised not to judge or repress myself. Now I see my more normal situation, I know that I feel comfortable being a boy, and like other boys I like girls but I also love dressing up as a girl.

I work more and more on that part of me, I have many things that I want to do as Jennifer, I want to learn how to do my makeup like a professional girl.
I never had the courage to go out (plus everyone in my neighborhood knows me and it would be hard to go out), so it’s on my bucket list.

As I said before, I like girls, but with the closeness that Jennifer has had, it has made me curious about what it would be like to have a boyfriend, who treats me like a lady, kisses me passionately knowing who I am, I would like to know what it feels like when a man makes love to me, dominates and compliments me as female (although so far I haven’t met anyone who likes a cross-dresser girl).

Also, I want to buy feminine items like prosthetics to shape my body, nice wigs, nail polish, etc. Along with that, I hope to finally have the wardrobe I’ve always dreamed of (dresses, skirts, bras, sexy lingerie, costumes).
Until now I have not met any other transvestite and I think it would be something of a lot of learning for me (although there are transformation houses “nearby”, I have not had the opportunity to go or enough money).

I am about to enter university and I want to be able to find my own personal space to be Jennifer freely, to be able to explore myself as a woman, live my own intimate feminine experiences and be accepted as a true lady, today more friends know who I am and what I love and like to do, they have supported me and I am just waiting again for the moment to be more feminine than ever, to be a true lady.

~Written by Jennifer~

Facebook Comments


  1. Want to learn about crossdressing

    1. Yes it is!! If you want to contact me, my email is and my Facebook is Jennifer Díaz Castro

  2. I really like your story

    1. Thank You so much <3

  3. Thank You so much <3

  4. There are a lot of guys out there who like crossdressing gurls. You’ll find one, and may you have the greatest experience of your life.

    1. Hi Cid, I hope so. It would be one of my great fantasies, distant but one of the most important :c

  5. I’m sure you’ll soon find a nice man who likes crossdresser girls. And he will take you into that bed and make mad, passionate love to you in that way two males can share.

    1. I hope it’s true, in my environment all the boys are closed to the idea. But I would love that, for a man to make love to me, to feel penetrated, to be at that point where I naturally produce small moans, it would be fabulous. If you know any guy interested in a woman like me, please let me know and I’ll get in contact.

      1. Hello Jennifer, just read your posts. You are amazing, all my respects to you and wish you good luck in your future endeavors both in College and in your personal life.
        At the same time I would love to meet you and get to know you in a more personal way.
        If you are still longing for that out of this world experiences , let me know.

        Thank you,

        1. Hi Sammy, I’m glad you liked the story, thanks for your well wishes and of course I still long to experience those out of this world things!!!

        2. Hi Sammy, I’m glad you liked my story, thank you for your good wishes and of course I’m still interested in having those out of this world experiences!!

  6. Hi Jennifer I read your story I’m a crossdresser. And I’ve been dressing up since I was like 8or9 it wasn’t till a year ago that it got sexual with men and it was good. I’ve never met a crossdresser in real life online on grindr yes. I do think I make a pretty girl.

  7. I would love to have a girl like you

    1. Rory how are you, if you are interested we can talk a little more in private Rory how are you, if you are interested we can talk a little more in private

  8. Great story resembles mine in a lot of ways except no real mention of purging I would love to have accepted myself at a early age and been able to have places like this to tell my story. Love you all Hanna from Indiana

  9. Hello Jennifer, it’s so great what you have done and continuing forward. I myself started crossdressing at 15. Was married for over twenty years as to which I had to sneak and hide with what little chances I had. I single now though. I live alone and I crossdress everyday. It’s awesome!!! I am wanting to explore more and currently seeking crossdressers for friendship/possible relationship!

    1. hello emily, it is a pleasure to hear from you, if you are interested in having more contact with me, let me know. kisses, jennifer

  10. Timmi/or ahem Tim would like to say,that you ladies are very brave and very honest..Timmi

  11. I can totally relate to your story Jennifer. Can we chat sometime. I fem name is Jessica 😘

    1. Hi Jessica, I’m glad you were able to empathize with my story, I’m sure we can talk, add me on Facebook as Jennifer Díaz Castro, my photo is red lips. Kisses ~Jennifer~

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