Exploring Something New

The first time I dressed as a girl was for a school play. It was a comic role where some guys were portraying a group of girls. I felt a mixture of excitement and shame because my friends were going to see me portrayed in female clothing. Soon after, whenever I would see my mother’s lingerie hanging out to dry, I had the urge to touch and feel it. The urge changed to wanting to try them on. Once, when I was 14, I found some lingerie in the bathroom while showering. My curiosity got the better of me and I tried them on. Years later I don’t recall how they had felt against my skin, but I remember the intense feeling of excitement when I put them on and stole a look in the mirror. The feeling of disgust got the better of me and I pulled them off as quickly as possible. During those days, I tried on panties a couple of times for a few seconds while showering.

This phase wore off as I got busy with studies, but I always had a lustful look at whatever lingerie I saw around me, whether at home, in stores, in movies, and even on the women in commercials. While I dated, I had an immense fascination with the girl’s lingerie, but I never felt like trying them on myself. At the same time, I was fascinated with the act of waxing and wanted to try it. This wasn’t possible as I still lived with my parents. I wasn’t sure if I wanted to do it because it felt like a weird thing to do and something I should be ashamed of doing. In spite of it, my ultimate fantasy remains going out fully dressed as a girl!

A few months ago I moved to a different country and I now live alone. This has allowed me to experiment in a way I couldn’t before. My old girlfriend was horrified at the idea of me shaving my armpits (I had spoken with her about this and broached the topic as a health reason because it reduces the stink of sweat). So the first feminine thing I did after starting to live alone was to shave my armpits. I’m not sure that this only a female thing as I many of my guy friends do this. The feeling is amazing! I love how smooth my armpits feel and it does make me feel sexy. Soon, I began to shave my torso; a shaved torso feels much sexier than only having hairless armpits!

I can’t wait to go further and try more feminine things like shaving or waxing my legs. I also want to move on to feminine clothing. Speaking of clothes, I plan to buy a cute lingerie set for myself. I welcome anyone’s suggestions? I’d be interested in advice on what other articles of clothing I could try, which won’t show under my regular clothes (for now).

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A straight guy who loves to crossdress from time to time. I may do it just on the inside or I may go all out

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  1. Nina-
    I know the feelings you describe as they are similar to many I felt, I remember the early days of truly exploring this side of me as I slowly spread my wings. If you had told me five years ago that I would have flown across the country in full Cyn mode to go to Esprit, and then gone out dancing in a club, I would have recommended you be put in an asylum as I couldn’t imagine being so bold. But such is the power and confidence we gain with the support of our sisters here-whether they are CDs, transitioning girls, or our wonderful SO members who encourage not only their own SOs but the rest of us here. So take the next steps when you are ready. s I always tell folks in chat: Never let someone push you faster than you re ready to go BUT never let someone hold you back from following your heart and dream! Thank you for sharing your story!

  2. Duck Duck 4 weeks ago

    Cant give you any advise on lingerie but you should definitely try to wear a skirt. Your mind will get blown away from the feeling of freedom ;D and its fun just to spin around and get it lift. As fore me I love Flared skater Skirts, they look lovely and cute at the same time and as I said before its fun ;D

    • Lucinda Hawkns 3 weeks ago

      yes wearing a skirt is breathless and exciting, feeling it move around, try wearing a nice dress too its exhilarating feeling and very sexy feminine look. i dress up its all the way panties,pad,nylons,dress or skirt and blouse and bra and make up and ear rings and perfume and a nice necklace

  3. Brandy Loveslace 4 weeks ago

    Hi Nina!
    I’m new here too and new to crossdressing(3 months)
    I think…
    Take yourself to Victoria Secret and get yourself some panties.
    Look online to see what size you will be. Get a couple different kinds/styles/materials to see which ones you like best. Personally, I prefer “hipster” and “cheeky” ones 😉
    They feel so nice! 🙂
    And go from there! And, wherever this journey takes you, good luck!
    P.S. lingerie shopping can become addictive
    I’m sure the other girls on here would attest to that lol


  4. Olivia 3 weeks ago

    when you are ready go for skirts and dresses. nothing like a dress to make you feel feminine.

  5. Author
    Nina 3 weeks ago

    I see many suggestions to go for a skirt. I think I’ll do that! But before I wear a skirt any tips for shaving my legs?

    • stephanie plumb 1 week ago

      If you don’t want to shave your legs just yet, try just shaving the tops of them down to half way to the knee and wear thigh-high stockings (tip: buy some dancers sock glue from Amazon to use once the silicon bands lose their grip – a few dabs of this and they stay up all day). This way you can wear a skirt and feel feminine but still be able to go out in shorts as a man. Works for me! The thrill of feeling the cool air on your thighs under your skirt between your stockings and panties is fabulous.

      • Author
        Nina 1 week ago

        Thanks Stephanie! This sounds perfect

  6. Cindy Carpendar 2 weeks ago

    Nina, I have been cross dressing for over 15 years. I enjoy the feeling of woman’s clothing and how it makes me feel. I first started buying clothes online at amazon. I then started browsing the women’s department at the local stores until one day I found something on sale that I could just not pass up. I went ahead and bought it with a few other men’s things. The another day you start buying things just from the women’s department. Just the other day, I bought two pair of leggings and a bra. nothing else and went through the line without really worrying much of who was watching. It grows on you and becomes a non issue. Most people don’t really care if you’re a guy in the women’s department. It really is not an odd thing. Enjoy your new life being who you want to be!

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