Crossdressing journey

[OpenRoad_71]

Are you a crossdresser, or maybe 'crossdresser curious', or even just a chap who likes to wear woman's clothing?
The journey is different for all of us, although there is a common moment: that first time we put on a garment of woman's clothing. Some of us felt guilty, some didn't, but for all of us who went on to accept the label "crossdresser", it felt right.
My journey was one of guilt and longing: guilt when I acted on my desire to crossdress and longing when I didn't. I threw away so many lovely garments: dresses, panties, body stockings. And dildos too of course
But now I don't mind saying: I am a crossdresser. I am Alison. And my male side too of course. We coexist comfortably.
I am at the point in the journey where the guilt is gone and I am accepting and enjoying my kink: i recently went to a men's suana in full makeup and dressed to kill. I flirted and flashed, and I loved it, can't wait to go back.
I have no idea where my journey is leading, I am excited and a bit nervous to find out.
Some of you are further along than me - what happened next? Where might I go from here?
And for those of you earlier on in the journey - how are you doing? What is your next step? Are you comfortable or still feeling guilty?

 

[Jessica616]

Good for you. I think we have all been in the places you described. I know I have. I have purged multiple times only to feel regret in do so. Like you I am at the point where I know this is a part of me and stop fighting it and enjoy it.

 

[OpenRoad_71]

Good for you. I think we have all been in the places you described. I know I have. I have purged multiple times only to feel regret in do so. Like you I am at the point where I know this is a part of me and stop fighting it and enjoy it.

Thanks
Loving that you have a word for it: "purging" - lol.

 

[saintcero]

I would dress if I could pass but I can’t. It’s too depressing for me to try to dress nicely and fail so I have stopped except for some fem man panties that I like to wear.

 

[Terrylipstick]

Mmmmmmmmmmmm. I miss it. I miss it so much…

 

[OpenRoad_71]

I would dress if I could pass but I can’t. It’s too depressing for me to try to dress nicely and fail so I have stopped except for some fem man panties that I like to wear.

I'm no expert but I don't think its about passing as a woman, if so I'd give it up as a non-starter! I think its more about just being comfortable in your own skin while doing the things our instincts demand. When I next go out as Alison it will be to a venue where I know people go to be around crossdressers, where they will treat me like a woman. There I will 'pass' as the object of many peoples desires!
It would be lovely to properly pass I am sure, but it would also be lovely to be filthy rich! We gotta work with what we got

 

[OpenRoad_71]

Mmmmmmmmmmmm. I miss it. I miss it so much…

Go on, buy those panties you know you crave, remember how amazing it felt to wear them

 

[Jessica616]

I'm no expert but I don't think its about passing as a woman, if so I'd give it up as a non-starter! I think its more about just being comfortable in your own skin while doing the things our instincts demand. When I next go out as Alison it will be to a venue where I know people go to be around crossdressers, where they will treat me like a woman. There I will 'pass' as the object of many peoples desires!
It would be lovely to properly pass I am sure, but it would also be lovely to be filthy rich! We gotta work with what we got

Well said

 

[Terrylipstick]

Go on, buy those panties you know you crave, remember how amazing it felt to wear them

Oh, I still do occasionally. Every once in a while that pink fog takes over and I’ll go buy some lingerie to wear for a guy, but more for myself. I wear it a few times and then throw it away. A few weeks ago the urge hit and I stopped off and bought some panties, went to an adult bookstore and put them on, tied up my shirt around my waist, and opted to just carry my shorts from booth to booth…. Parading around in a thong. I’m sure that to anyone else it looked unappealing, but I loved it. I just don’t do it anywhere near as often as I used to, or want to.

 

[dingdongditchding]

I want to meet a bi cross dresser for some gay ol times we can have

 

[ZacharyFagg]

I would dress if I could pass but I can’t. It’s too depressing for me to try to dress nicely and fail so I have stopped except for some fem man panties that I like to wear.

You don't have to be passable. Most crossdressers aren't unless they really know how to do makeup. If you want to dress, do it and enjoy!

 

[saintcero]

I have my man panties on and I am happy.

 

[Missmister]

Its been a long time but i remember dressing for a man i would meet up with at the hotel, god i was such a turn on for us both! I wish i could get back there, or somewhere like that again!

 

[dougroundup]

I only like to dress up if I can fully present and look hot and sexy. I am told I can pass but I really know that it is all fake. Its all about dressing and I can look good dressed but I cant look anything how I would wish if I were undressed. I suppose much of beauty if fake.... I truly enjoy the moments I can be not only effeminate but can go out and feel sexy and desirable. I definately turn heads and have been propositioned much more thanI have been as a man. I never thought I could ever present half way decent and felt like it would be foolish to even try. I was repulsed to look into the mirror and see a man in a dress. It just took a little investment in time and money to buy the right stuff. Quite a bit of nerve to shave completely smooth, pluck eyebrows and grow long hair. But its now the new normal and I can be either. I will try to upload a pic and hopefully get some feedback on how I look.

 

[Smoothshavendad]

I only like to dress up if I can fully present and look hot and sexy. I am told I can pass but I really know that it is all fake. Its all about dressing and I can look good dressed but I cant look anything how I would wish if I were undressed. I suppose much of beauty if fake.... I truly enjoy the moments I can be not only effeminate but can go out and feel sexy and desirable. I definately turn heads and have been propositioned much more thanI have been as a man. I never thought I could ever present half way decent and felt like it would be foolish to even try. I was repulsed to look into the mirror and see a man in a dress. It just took a little investment in time and money to buy the right stuff. Quite a bit of nerve to shave completely smooth, pluck eyebrows and grow long hair. But its now the new normal and I can be either. I will try to upload a pic and hopefully get some feedback on how I look.View attachment 2581138

Very hot!!!

 

[PinkPanties4me]

I say buy it, wear it, enjoy it! I am older (70) and I know I would never pass for a woman. But that’s not what wearing lingerie is for me. I love the feeling of satin or nylon against my skin. It makes me feel feminine and submissive…I have never been with another man (married too long) . But my wife begrudgingly accepted my fetish and I am okay with that.