What?s next?

[Sally Paradise]

Crossdressing, for me, has mainly been about the evolution of my feminine side. I have no desire to go full time. I am comfortable going weeks at a time without dressing, however, my ideal situation would be one where I would be able to dress a few hours a day 1-2 days a week. I enjoy my masculinity as much as I enjoy exploring my feminine side.

That said, my journey has been very enjoyable. I experimented in my teens, lost track of crossdressing a bit in my early 20s, got married, settled down, experimented with a few odd items again, and then dove straight into things.

I bought myself some panties from Soma, the sales lady at least pretended that I was buying for my wife, possibly thought I actually was. Then hosiery, skirts, a blouse, some clearance dresses. Then my first forms, corsets, a cheap wig or two. Then makeup. That was a long struggle, and it gave a sense of purpose, something to improve on. All while accumulating more clothes, a cheap pair of heels, a daring pair of leather boots...all of this happening in secret from my wife and everyone I knew.

About a year and a half ago, my wife found my stuff. Lots of questions, I?m sure some of you have been through similar experiences. Eventually, my wife understood, and continues to be supportive. It?s like she finally knows who I really am, and I know how fortunate I am to have that and her. We?ve gone out with me dressed, she buys me clothes and makeup sometimes. Life is good!

I look at my crossdressing as an evolution. I started small, and keep progressing. Improving my look, getting better at providing a feminine figure, finally getting the hang of eyeshadow. I?ve gone out night with my wife and solo. I?ve gone shopping in the daytime by myself. I?ve turned men?s heads and received compliments from women. I?ve also seen looks of confusion and maybe even disgust. Everything I?ve done has been a progression with a combination of baby steps and massive leaps forward over an extended period of time.

My question to myself now is...what next? I?ve done a lot, I know there?s more out there, I just don?t know what the next steps are. Has anyone else been in this place? How did you move forward? Transitioning will never be on my agenda, it just isn?t me. So...where will this exploration of self take me next...

Time will tell I suppose.

[Maid_Marion]

Hi Sally,

I'll suggest you have a discussion with your wife. Maybe there is something that would excite her?

Marion

[Jenny22]

Sally, you've already done what many of us would 'kill' to do. so what's next? That's your call! but, I'd suggest that you not push your wife's acceptance too hard. Many ave been known to do a 180. Might I suggest that the two of you take a vacation with you fully en femme the whole time. That can be some great fun. Good luck!

[AllieSF]

For many who only consider themselves CD's you are living the perfect life., So, in a way you are nearing the top of your CD spectrum. Left to do? Well, I started late in life crossdressing from zero, i.e. I never did that repeatedly because I wanted to. I just took one step at a time, and like you, some can easily be considered big leaps. The first was wanting to go out dressed as often as I could. That led to meeting and now have some wonderful friends from CD's to post op TS's. Continuing with those steps, I finally came out to everyone as trans (TS). I am now full time with a couple of gender confirming surgeries already completed. I am not saying that this is your path as you clearly stated you won't go that far, i.e. jumping spectrum's to the TS one.

So, maybe for you it is to just get out more frequently, meeting some like minded friends and have a wonderful time doing all of it. Once I had been out a few times, I had no fear, anxiety or whatever at all. I was super happy and loved that time out. Before admitting I was going much further down that path, I had 2 subscriptions to see different types of plays, one a Broadway musical one, was getting out 2-3 times a week with friends, could and did go everywhere I wanted and loved every minute of it. Good luck and just let whatever is happening and might happen, happen, of course with sane limitations. Enjoy and live your life as best possible.

Allie

[docrobbysherry]

Sally, I don't think I've ever been where u r now!

I've dressed in dozens of foreign countries. Portrayed various fantasy"women" in my stories, on TV, and in music videos. I'm prepping for appearances in a couple more in the weeks ahead. So, I KNOW what's ahead for Sherry.

But, I've never been where u r now and never will be. So, enjoy! And, let us know what you're up to next!

[suchacutie]

I also suggest that the rest of the steps be a joint experience wirh your wife. My wife has been an incredible source of knowledge and perspective.

[Stephanie47]

I cannot say that I have done it, but if I had the opportunity when I was younger I wish I could have joined a support group. My wife gave me her blessing, but at the time there was none in my area (early 1980's). It would have given me the opportunity to mingle with like minded individuals. I've read many posts on the site of ladies meeting in Detroit. You may want to peruse the postings here. Or maybe one of the Detroit ladies will chime in.

[Micki_Finn]

This is the problem with looking at crossdressing as a hobby in itself. It’s insular. The point of your dressing becomes just to be better at dressing and when you hit that pleateau, where DO you go from there? If you’ve perfected your presentation, then the only thing left to do is live your life.

I hit that stage really early in my dressing. I realized that dressing for its own sake wasn’t what I wanted. I dress to express myself, and so I took that to the Nth degree and got into Drag.

The bottom line is that there isn’t an ultimate goal. There’s no last level or final boss. It’s about expression. Did Picasso say “well, I’m good at painting. Now what?”

[Helen_Highwater]

Sally,

At a practical level, given you have your wife's support, can I suggest something.

Okay you don't want to go full time but one thing you could do is at least experience what it'd be like. As I've written ad nauseum I spend a week away from home each year and go enfemme for the whole period.

I love doing it but it does have it's challenges. Just putting and talking off makeup each day, perhaps needing to glam it up at some point as you switch from clothes shopping to an evening out. You quickly realise what can be involved in a GG's life.

I'd love to spend more time dressed and going out and about but circumstances won't allow but my weeks away also confirm I'm not (yet?) Wanting to go full time.

Going to bed enfemme knowing when you awake from the very first moment on you're going to be spending the day enfemme is an experience I can whole heartedly recommend to all here. Immersing yourself into that mindset, for that is the best way to do it, carries you forward and has given me some of the best days of my life.

I'll just add, it's also an opportunity to do things any GG would do. Travel on public transport, take a taxi, eat in restaurants, go to the cinema, get a makeover at a cosmetics counter. There's so many options there to be enjoyed.

[Krisi]

Why do you need to "move forward"? You can move at whatever pace suits you or you can stay at a certain level. It's up to you, your wife and your social and career circumstances. Many people say that crossdressers eventually transition. There's even a "joke"" What's the difference between a crossdresser and a transexual? About two years.

It's not true, you can be a crossdresser the rest of your life if you want to or you can give it up completely. It's all up to you.

[Sally Paradise]

Lots of amazing replies! Thank you all for being so supportive. I guess because I?m still relatively new here I should given a little more background about myself initially.
Firstly, I did used to look at dressing as a hobby, but realized awhile ago that it was much more than that. I can and have let go of hobbies, I know that crossdressing is far more ingrained into to I am than that.
Second, for what it?s worth, I?m 6?2? with a very broad pair of masculine shoulders. I do not pass as female no matter how hard I may try, but that will never be a roadblock for me again.
Next, I actually have dipped my toe into the local crossdressing community, not with support groups, but there is a local bar that caters to us that I have been to a few times. I have met some great people, and I have met some people who only want attention on themselves and come across as very jealous of the new girl. Of course, no bar setting is ever perfect, and always a mix of personalities, but it?s still fun.
Also, I have considered therapy and support groups, but at this point I feel I know who I am very well and I love myself from every angle. I have become very comfortable in my own skin in every way. I guess I never really feel as though I need the support these days, but definitely would have benefitted from it a few years ago.
I should apologize if I came across as being in a bad place because I don?t know what?s next. I know that I?ll continue on this journey, it?s not something I?ll ever stop. I?m in a pretty great place, but there were definitely a lot of painful experiences and deep feelings of loneliness for many years. I?ve put the negativity to rest, I?m very excited for what the future holds, whatever that may be!

[kimdl93]

Seems like you are on a common path. With experience grows confidence. That may allow you to spend more time out in the real world. You seem to enjoy it and take a healthy attitude about. My prediction is that you will find more opportunities to live and enjoy a portion of your life as a woman, but I doubt you?ll suddenly or gradually decide you want to alter the fundamentals very much, cause they seem to be working for you.

You strike me as a person who would be comfortable viewing oneself as non-binary, and probably perfectly comfortable living the remainder of your life as you are. Have you considered or are you out to any degree to family, friends, co-workers, neighbors? That might be considered as a step towards transition, but it might also be just a way of allowing yourself more freedom to live as you wish.

In any case, i would say that with your wifes support, you are looking forward to a really great life!

[Sallee]

Hi Sally, You write a familiar story. If it wasn't for the spelling of your name I would have thought I wrote it. I'll fire an answer to your question. Is there more out there? No I don't think there is unless you want to take it further. If you pass well and have been out and about, malls, restaurants and other attractions and haven't had a problem then why take it further unless you want to transition. I know for me I have been out and about, bars, restaurants and almost any were else I wanted go and for the most part haven't had a problem. So to me the next step would be transition or full time. I'll be honest, I fear that for a bunch of reasons But I think the biggest reason CDing would loss its thrill so cross dressing would just be dressing and everyone does that. Anyway that's how I feel I want CDing to be special and I know it can only go so far so I have to keep it in perspective with the rest of my life and that can be hard.

[Joyce Swindell]

Great thread!!!
I'm digging it!!
If you haven't done a CD cruise that's on my bucket list. Maybe pack no guy clothes? I know that might make me a little nervous. My wife is also very supportive so she is looking forward to a cruise. How I show up for it really is no big deal for her.
We're planning retirement in a motorhome so I plan on just being me full time.

[Kandi Robbins]

Not sure what your age is or if children are in the picture, but your story is very similar to many of ours.

While I am from Cleveland, I found my feet, so to speak, in Detroit.

For me, the puzzle was once I was dressed, what do I do? After a while shopping becomes both expensive and adds to the wardrobe you cannot possibly wear.

Pre-COVID I volunteered significantly. That allowed me to dress in many different situations (casual, dressy, formal, etc.) and interact with mainstream society, receiving the type of acceptance we all seek.

Find an activity for Sally and that will start making it no longer "crossdressing", but just you being you.

[Sally Paradise]

Great points and great ideas everyone! My urges to dress have never really been so strong as to want to want to dress for multiple days in a row. Pre-Covid, my time was well balanced and I was exploring getting out more. Hopefully that can resume, at least to some to degree, around September or so. But, not sure a full vacation or cruise as Sally is for me...yet. Definitely something to keep in mind as my journey progresses.

My wife will be kept up to date with anything I do, and have the opportunity to be a part of most of it. She also knows and understands that it?s something I do for me, as an outlet and a personal exploration, and that sometimes I need it to be mine. The balance is working. I do worry that at some point she might lose interest in that part of me as I?ve read about that happening with other spouses and SOs, but so far so good. Lots of communication and honesty is the key.

I think all I can really do for the next little while is look forward to being able to go out again once things normalize a bit more and kids potentially go back to school (I have a high school senior and an eighth grader) and pick up where I left off before all the craziness.

[Natalie5004]

This is the problem with looking at crossdressing as a hobby in itself. It?s insular. The point of your dressing becomes just to be better at dressing and when you hit that pleateau, where DO you go from there? If you?ve perfected your presentation, then the only thing left to do is live your life.

I hit that stage really early in my dressing. I realized that dressing for its own sake wasn?t what I wanted. I dress to express myself, and so I took that to the Nth degree and got into Drag.

The bottom line is that there isn?t an ultimate goal. There?s no last level or final boss. It?s about expression. Did Picasso say ?well, I?m good at painting. Now what??

Micki. You have a great insight. Your comments are always spot on if not a little tough at times. But still spot on. Keep it up. Love it.

[Paulie Birmingham]

This is the problem with looking at crossdressing as a hobby in itself. It’s insular. The point of your dressing becomes just to be better at dressing and when you hit that pleateau, where DO you go from there? If you’ve perfected your presentation, then the only thing left to do is live your life.

I hit that stage really early in my dressing. I realized that dressing for its own sake wasn’t what I wanted. I dress to express myself, and so I took that to the Nth degree and got into Drag.

The bottom line is that there isn’t an ultimate goal. There’s no last level or final boss. It’s about expression. Did Picasso say “well, I’m good at painting. Now what?”

That's a close minded point of view. Just bc you wanted to Express yourself in drag doesn't mean others can't enjoy CD as a hobby. There Is a pretty wide range of people under the CD umbrella. No need to take shots at those who don't follow your path

[Sally Paradise]

With all due respect to those who commented on it, I didn?t see Micki Finn?s comment as tough or closed minded at all. We all have our own path to follow and I actually found a bit of clarity in the comment. I?ve thought about getting into drag to be honest. She?s also absolutely right in that I should just live my life without worrying about what?s next. I am constantly reminding myself to take things as they come and appreciate new opportunities as they present themselves.

I am always open to any form of discussion, and certainly don?t mind constructive criticism when it comes from a good place. Also open to discuss anything privately if anyone is curious about anything on my end as well. I came here for discussion, and I have been enjoying it thoroughly!

[Paulie Birmingham]

Definition of insular
1: characteristic of an isolated people
especially : being, having, or reflecting a narrow provincial viewpoint

[Bobbi46]

I think a lot of us must wonder "what next", after that first venture outside. Then comes another day outside. leaving transition aside (which I considered but decided it was not for me) after the first few times outside it becomes a way of out for an evening meal to a restaurant was a "new" thing for me but that was a long time ago (or it feels like that) now every day dressing for me is a normal way of life, there is no "what next" except when I I decide I need something new to wear like a skirt.