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A little over a year ago, I told my wife that I wanted to wear panties and as a result of that wonderful conversation and my amazing wife, I came to the realization that I’m a cross dresser. Since then, I’ve been trying to come to terms and accept this feminine aspect of myself, and to understand her. I’m not sure I will ever understand any of this, but I’ve learned to accept and surprisingly, love this part of me. No more guilt. As a friend once said, there’s no shame in my game.
Initially, I just wanted to wear panties and maybe a bra from time to time. But after reading so many of your stories about dressing fully and going out in public, I quickly realized that I wanted to do those things too. I can only guess that my Jill persona is growing more and more. But with so many of my friends and some family members being very conservative, I’ve been too afraid to do so. I’m mostly worried about alienating my son whom I love very much. And like a lot of you girls (you wonderful, inspiring women!) I began to chafe at being forced by my fear to stay in my home where no one could see me or harm me. I longed to go outside and let the sun shine down on my face, on Jill’s face.
Last month I bought some breast forms (my God they feel so good) and my wife wanted me to get a wig, although a cheap Halloween wig, it looks fairly good and I love the color, a rich brunette. Then, just last week, my wife (she’s a real keeper) asked me to go with her so she could buy some makeup she needed, but really, she wanted to get me some makeup at last. I did watch a couple of videos explaining how to do it, most were too confusing, but I did find one that made sense and was easy to comprehend. So, I tried my hand at applying makeup. One word: Disaster.
Then yesterday, a makeup miracle! I tried applying makeup for the second time and the result while surely amateurish, looked amazing to me! It looked so good that I had to put on my wig. And that looked so good that I had to get dressed. I put on a brand-new pair of hot pink butt lifting pants (sadly, I don’t have enough butt to lift, LOL) and a black, short sleeved blouse along with my bra and forms, and pearl necklace and some hot pink heels. I loved how I looked so much, and I wanted so very much to walk outside, that I threw caution to the wind and walked out to my car in broad daylight at 10:00 in the morning! It was a short walk to be honest, but it was progress. I was so excited, but not in a sexual capacity, more like a liberated feeling I guess, that I felt like I had to go further. Gathering my courage again, I walked out the door again and walked to the communal mailbox which is out of sight of my house. Still not a long walk, and as far as I know, not one of my neighbors saw me, just some guy driving by, but it was much further.
I don’t know if I’m bummed out that no one apparently saw me or not. But before I went out, I decided that if a neighbor saw me and asked me why I was wearing women’s clothes, I would just come clean with them. Coming out to my friends and family may take time or it may never happen, but I did it! I walked out and the morning sun saw me…….and it was good.
Thanks for reading this and for your friendship, support, and sisterhood.
Love to my sisters, Jill
That was a nice story it sounds like you had a good experience no unforeseen problems this time so it is a confidence builder.I wish I could do the same but that is not in the cards. Be careful and enjoy yourself don’t take any chances that may cause you any harm .I have done a little to expose a portion of Debbie but being very discrete and not too close to home when a teeny bit obvious. It still felt so good Thanks for sharing.
Hi Debbie,
I’m happy you enjoyed my story. I hope your circumstances change enough that you can do it too. I’m a very careful person and this felt safe enough that I wasn’t worried. Most of my neighbors are in their 50’s and 60’s and that was another reason I felt safe. I certainly wouldn’t go into a biker bar or go to the Hell Angel’s house (they have one here) and knock on the door, while dressed. Knowing my neighborhood was safe was my first consideration. Thank you for the wonderful advice!
Hugs, Jill
Thanks for sharing a lovely story, Jill. You know, they have hip forms, too. They used to be called symmetricals.
I was in theatre before education. I did my own stage makeup and even aged makeup but street makeup is still a challenge for me. It’s definitely its own breed of cat.
Hello Wanda,
I have seen the hip forms, and maybe if they weren’t so expensive and if I had a more room in the closet to store them, I’d actually buy some. I’ve never done any kind of makeup before other once or twice for Halloween and that was very minimal. I have so much to learn. The video I found useful was called “Boy to Girl Makeup Tutorial (Beginner)I Become A Girl”. You my find it useful.
Hugs, Jill
Awesome Jill thanks for sharing what a wonderful story so happy for you. Your wife sounds truly amazing also be sure to thank her for all her wonderful support.
Jill –
Thank you for sharing your wonderful experience. i can only imagine how you felt doing that. You are lucky to have such a lovely wife that helps you. My wife has helped me as well at times. We were shopping once and as we walked by the cosmetic section she said lets get some make up for Suzanne. She picked out everything I would need in the color tones she thought would be right. It was a fun experience for me especially as it was unexpected. When we got home I out my make up bag together and then she showed me how how apply it. I think I looked pretty good when she was done. I’ve done my make up a few times since and still need a lot of practice but that is part of the fun. I hope you get to have the same experience soon.
XOXO
SuzanneHi Suzanne,
Your wife sounds amazing too! When we went to the store to buy our makeup, my wife picked out everything based on my skin tones, which was a good thing, because I assumed I’d need the lightest foundation possible. But she pointed out that I have a lot of red pigments in my face. Her wisdom was my gain!
Hugs, Jill
Hi Jill,
Thank you for sharing your beautiful experience! For now I will be living vicariously, so it was wonderful to hear it!
💕Lara
Thats fantastic good news! Our first time out is so exciting and one we never forget. Now you’re no longer a closet virgin and I know you want to do it again and push the boundaries as far as you can. Be safe, keep at it, blend in, and soon you’ll be walking the Mall or going out to restaurants. Kudos to you!
Dear Michelle,
Thank you so much, but I couldn’t have done it without the inspiration and examples from all of you brave ladies, and that’s the truth. The Mall? Hopefully, someday, maybe within the year. But for now, I’m content with really small steps.
Hugs, sister,
Jill
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Hi Jill.
Yes CDH has inspired many of us who maybe would have never been brave enough to go out and I’m glad you took that first step. While miles and oceans may separate us we are all in this together. Every day I go out under dressed and I always think of all of you girls somewhere wishing or doing the same thing or more. We are a sisterhood in spirit and gone are the days of lonely isolation feeling like we are perverted freaks.
Have fun sweetie and you know we want to hear of your adventures!
Great story, I enjoyed reading it and hope you continue to explore and enjoy this newfound wonder that is in you. I would suggest caution about going about your neighborhood since once the genie is out if the bottle you can’t put it back. You seem apprehensive about family and friends knowing, but if your neighbors know word could spread. There is nothing wrong with coming out, but you want to control it, not have it control you. That doesn’t mean you can’t go out, just be careful how and where you do.
Enjoy, and post more and pictures as well, your makeup and outfit sound wonderful.
Hi JJ,
Thank you for the compliments on my post. I wasn’t sure it would be read because I made it so long, so thank you for taking the time to read it and respond! I appreciate your advice, and caution is my middle name in this game, but my family rarely comes over and only one neighbor has met my family and he wouldn’t say anything. I considered that before walking out the door. I’m more worried about bumping into family and friends if I go to stores or restaurants than if I walk around my neighborhood. It seems I can’t go anywhere without bumping into someone I know.
Hugs, Jill
Such a great story girlfriend! You are couragious for sure. As for makeup…oh my, the hours I’ve spent watching YouTube videos and countless online tutorials. While my wife is supportive she’s not one to go makeup shopping with me. In her defense though, she doesn’t wear a lot of makeup. There have been times that she’s asked me about things I’ve learned in my makeup journey.
Love always girlie!
💖LolaDear Lola,
This was the first time my wife went shopping for makeup with me, which is why I’ve never owned makeup before. Like your wife, my wife doesn’t wear makeup very often or very much of it when she does wear it. She uses enough to make her pretty eyes really pop! So far, I’ve found that searching on YouTube for makeup tutorials from cross dressers, is the best way for me. If you haven’t yet, I recommend giving that a try. Thanks reading my post and responding. It was very sweet of you.
Hugs, sister, Jill
Hello Jill YouTube was the first place I looked. Haven’t tried make up yet but does me excited thinking of it. I really like eyemakeup and lipstick 💄 be safe Jill.
Kisses
STEPH
It begins! Congratulations, Jill! I’m so happy for you; it’s incredibly exhilarating to fully inhabit yourself like that, in broad daylight. I suspect that now that you’ve had a taste, you’ll want more. Best wishes for you journey. And to have a supportive spouse is the greatest gift.
Good for you Jill. Getting out there as your fem self was very satisfying, but sounds like it was not enough. The desire to keep going a little further can be so addictive. Hope thing keep coming out great for you.
. Cassie
That is so awesome Jill,
Thank you for taking the time to share your experience and the courage it took to come out.
you know the pink fog just gets stronger from here on.LOL
Huggs Patty
Hi Patty,
Oh you’re so right about the pink fog, OMG! And it was a real pleasure to share my experience, but I’m just so thrilled with all the kind responses. I thought maybe one or two women would comment and maybe a few more would like my post. But you’ve all surprised and humbled me, and at the same time made me so happy to be a woman among all you wonderful ladies!
Thank you and hugs to you, Jill
Congratulations, Jill! Sounds like you’ve got a wonderful wife and a happy life.
Much love,
Raquel
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