Easing into Dessing Thanks to Support of SO
Hello all! I was happy to find such a supportive and welcoming place after a recent turn of events...
One of my earliest memories, which I’m sure many people on here can relate to, was being caught trying on a bra of my mother’s while in elementary school. Through my adolescence, teens, early 20s, and now almost 30, I have had a fascination with transgenderism and cross dressing. This manifested itself by wearing women’s underwear and other random garments I could come across, such as ex-girlfriends’ and sister in law’s clothes (sorry sis!) but I’d never full blown dressed, shaved, worn makeup, bought a wig, all the other things that go along with this part of my brain.
I’ve felt a great deal of shame and guilt since the age of 21 after telling my first love I liked to wear panties, and she soon left me after that. I’ve always felt that I needed to do all I could to hide this secret of mine from everyone around me. Enter, my girlfriend now.
I told her late last year about how I liked wearing panties, and guess what, she was completely cool with it! Recently, while living across the country from each other for a short period of time, she shipped me several pairs of panties for my birthday and has requested I send her sexy pictures almost daily. It’s been such a fun game and I’m kind of surprised at how into it she’s getting. She’s expressed to me how there’s no need to feel guilt, shame, or embarrassment about this because in the grand scheme of things it’s extremely harmless and it makes me feel sexy. I told her about all the shame I’ve felt over the years and expressing that to her was very cathartic.
Earlier this week she texted me and said that she had an idea, and that when I visited her in the next month, she wanted to buy stockings and a garter belt for me. I was stunned to say the least. When I asked her why, she told me that she feels the pinnacle of sexy when she wears that combination, and she’s sure I would too, but she wanted me to shave my legs first! This lead to a lengthy discussion about her dressing me up fully; makeup, wig, shaved legs, the whole nine.
I tried not to seem overly excited at first, but when I told her this was something I’d always wanted to do she wasn’t exactly surprised. She told me how happy she was that I’ve been so open about this, and how she’s looking forward to having, “girl time,” with me. She’s told me over and over again that she wants to explore this with me just as much as I want to with her. We’ve even been sending Amazon links of potential outfits to each other.
These conversations have allowed me to feel no self doubt, shame, or guilt when researching ways to dress, techniques, and outfits. Because of her I felt the courage to seek out a community like this!
I’m finally learning to accept this part of me after trying to avoid it, or not delve so deeply into it all these years, and it’s very much because of the support from someone I’ve finally shared every part of myself with.
I wanted to share this as my first post so I can one day look back on it and see how far I’ve come, and spread some joy for those of you who are like minded. I hope this may also inspire a few of you who are still in the closet in your relationship about your dressing up.
Thank you for reading, it’s a pleasure to meet you all!!!
