What would you do differently, if anything if you knew 20 years ago what you know now

[JenniferZ]

I was thinking about his today. I have a wonderful wife who is fully accepting - sees it as clothing and really doesn't care. If I could go back in time I would have been open about it from the beginning and I would have dressed a lot more. I enjoy dressing immensely, however for years I hid who I really was - and I have no need to do that anymore. I would hide my stuff, keep it in the office, go to the office on weekends to dress and now I have a drawer of my own for panties, bras and stockings that is in my wife's dresser. I used to sneak a transformation and now I would involve my wife. I know we can only look forward, but for some reason - January 1? - I thought about this today.

[kimdl93]

It pains me to look back and consider all the errors I have made?but we learn by making mistakes (and avoiding making the same mistakes in the future). Perhaps my biggest mistake of the past 20 years was not being self aware?really knowing myself.

[April Rose]

It was about twenty years ago that my son found out I was a crossdresser. I feel bad that he kept the knowledge to himself for eight years before I came out to him. It doesn't seem to have bothered him in the least, but it bothers me.
Times are a lot better now for trans spectrum people than they were twenty years ago, so I don't think I would have changed much.

What I would have changed is, I would have tried harder to get my wife to quit smoking. It ultimately killed her, and I regret very profoundly that I didn't rant and rave and yell and scream or do whatever it took to make her stop. It's probably irrational, but I will go to my grave regretting that.

[Maid_Marion]

I wasted a lot of time trying to wear adult guy clothes that never fit properly, as my waist never got wider than 28 inches. Long shirt sleeves were too long.

My waistline is now 25 inches and I have an easy time finding girl clothes that fit. :)

[Erin77]

20 years ago..... I wouldn't have walked by the LGBT office at my college. I would have gone in. I often wonder what would have happenned if I had opened the literal door. I'm sad I didn't way back when.

[Karren H]

20 years would not do it for me because I knew what I know now, then. Would have to be more like 50 years for me and times would have had to been a lot different than they were 5 decades ago. Fun to think what could have been but it does not really make things any better today, for me that is.

[JenniferMBlack]

I wouldn't have questioned myself for another 20 years. I know I would have just started transitioning then. But then my life would be way different. So I still say things happen for a reason at the right time.

[Nadia Wren]

The internet and the culture has made it easier today. But 20 years ago, with what I know now, maybe I'd be a bit more aggressive in purchasing items for myself in stores. There is varied experiences with a SA, but in the end, you get what you want.

[Elizabeth G]

Kim said it all. Self awareness 20 years ago would have put me on a very different path than I'm on now.

[Rachel Anne]

The problem with questions like these is that 20 years ago was a different culture and 30 years ago even more so. I think many of us made the best choices we could with the resources available at the time. And those choices were certainly influenced by the people and the life we had around us. Of course, we all like to think about "what if", but realize that would most likely have changed all the good things that happened as well.

[GaleWarning]

I would have to go all the way back to the 1970s and try to talk more openly with my wife about my crossdressing. Perhaps we might have reached an accord. Or perhaps I would have realised sooner that our marriage was irretrievably doomed.

[Kris Burton]

Twenty years ago I was deep within a midlife crisis, in therapy which I have been in and out of since my college days. I was aware of my desire to CD but had not even admitted it to myself, much less anyone else including the therapists, thus rendering the therapy of marginal use at best. It now appears that was at the center of so much of my angst throughout my life, and was up until very recently. So, if I knew then what I know now I would have embraced that side of myself and not buried in my psyche. In theory, that would have led to a happier, more well adjusted, and productive person. I probably would have come flying giddily out of the closet embracing my CD side with abandon. I wonder how well that would have gone over with those around me at that time? I don't know if I would have met with the same acceptance that I have now. So, despite the angst, it's probably better the way things actually occurred.

[MiniRock]

If I answered this question properly, it would be way too long. But I guess I would have succeeded in raising my children. Instead of not having seen them for thirteen years (and counting). That never stops hurting.

[SaraLin]

If I'm going to be honest and stay on topic - I can't see where I could have done better.

Sure, there are a lot of "what if's" or "I wish'es", but I agree with Rachel Anne and I believe that I did the best I could with what I had to work with.
Overall, I guess I did pretty good - even if my wife doesn't want to be "married to a woman." I guess I can't fault her for that, right?

[GretchenM]

Quite frankly, I don't know. At my age I really can't remember 20 years ago. ;-) But if I knew now or knew someone 70 years ago who knew what I no now I think my life would have been very different, to say the least. I have no idea where I would be in this maze, but I suspect all the confusion, fear, self-disgust, etc. might well have not happened.

I am well settled into my identity now and that took about 8 years after acceptance and surrender to my inner self and identity. However, I doubt that if things had been very different, as described, when I was 6 I might have transitioned and now be a trans grandma or it might have all resolved and not even be a part of my life. However, I think the latter is unlikely unless all of this is, in fact, just the result of a bunch of choices. Not likely to be the case as the science says, to a high extent, the gender behavior pattern we live is founded in genetics, but only broadly so. The rest is the play of experiences, hormones, choices, and a pile of other things.

[Debbie Denier]

A lot of ifs buts and maybes. If I had the experience and head on my shoulders that I have now .I might have done things differently. I don?t want to look back with regret. But look to the future positively. I am happy with what I have got from life .It could have been worse if things were done differently.

[DianeT]

36 years ago, actually. "Hello, dear girlfriend and future wife. I have something to tell you."

[NancyJ]

I would have understood that cherishing my wife and putting her first would allow her to give me more of what I needed. Instead, I selfishly hid some of my dressing and kept secrets from her. The more I have fully devoted myself to her, the more she has tried to understand my feminine needs and relaxed her boundaries. Seems simple now, but I was afraid to let her lead. Nancy

[Connie D50]

20 years would not do it for me because I knew what I know now, then. Would have to be more like 50 years for me and times would have had to been a lot different than they were 5 decades ago. Fun to think what could have been but it does not really make things any better today, for me that is.

Might be my age (66), but I agree 100% with Karen I need to go back 50 years.

[alwayshave]

Karren is right, by 20 years ago I had fully accepted myself, I'd need to go back an additional 30.

[Jenn A116]

20 years ago? I would have done electrolysis and gotten rid of my facial hair. Even in guy mode, not having to shave would have saved me many, many hours over the years.

[cdinmd206]

Joined a bondage/discipline club!!!!!

[Angela Marie]

Given my age, 67, I would have to go back 40 years. But that was a much different time. I prefer to think of myself as 27 now, and what would I do in the present.

[Brenda Freeman]

I have wondered about how different my life would be if I fully explored my crossdressing early in my life. How I would look and where would I go from their. I used to regret the lost early experiences. 16 years ago I finally dressed fully make up wig the works for the first time at a transformation studio, my wife did not know. I looked in the mirror and saw the side of me I always dreamed of. Looking back it was the right time. I had been married over 25 years hiding my interest from my wife. But I could not hide it anymore as I was dying on the inside, and mentally a wreck. The benefits of waiting until I was 50 in 2005. I found the love of my life, raised two children so proud of both. Worked hard and saved to enjoy a comfortable life together. The information today, resources, support groups and LGBT success stories have provided so much information to educate the public sadly not all welcome it. I was very lucky and was sure my wife knowing her would understand. It took some time what a shock. We have worked together to find space and time for Brenda. I think It was the right time for me because I can now be whole and luckily lost nothing I love.

[Karren H]

Joined a bondage/discipline club!!!!!

It is never to late to do that! Lol

[ShelbyDawn]

So many have already said the same thing but I'd have to go back further, preferable to when I was eighteen or so but even thirty years.
As for what I'd change, well, the clothes I'm wearing would be the same but it wouldn't be called crossdressing.

[Stephanie47]

For me, in order to answer the question I'd have to go back fifty years. I'm 74. At 54 years old, nothing would have changed. My wife and I had "The Talk" when I was about 36. She said, if I wanted to join a support group, that was alright with her. Leave her out of it. I looked, but, there were none to be found. Maybe, I should have continued to search year after year. There are a lot of things I would have done differently if I went into "Mr. Peabody's Way Back Machine," and. cross dressing does not top the list. Maybe, I should ask my wife what she would have done differently forty to fifty years ago. Can't cry over spilled milk.

[kellyanne]

Looking back 40 years, as I turn 60 soon, I would not change much CD wise - perhaps more effort at trying to date another CD and attending regular TG events.

Being independent and a CD with many interests and seeing almost everyone around me divorce in the interim period - the choice of the single life is still best for me.

One larger life thing I would change is more family interaction and more effort on my part to see my sister, mom and dad who are now passed on.

I like to play the percentages and I can pick a date well but never had any confidence in picking a spouse.

My UNI girlfriend, a pillar of the LGBT arts community, I thought would be CD tolerant but was not - being financially risk averse I decided then to only date and not cohabitate or marry.

while nothing is perfect, things have went rather well all in all and I am almost always in a happy go lucky mood.

[Rachel Anne]

While I'm not quite as old as some, I still would have had a very difficult time with the resources & environment that were then available, family, friends, career etc, even if I had gone "all in" and successfully stealthed. I certainly appreciate the "you need to be true to yourself, or you'll be miserable forever" mantra that gets put out there sometimes, but I don't think it's quite as black and white as all that. I've been very lucky as it is in that I've been able to express myself to the extent I have within my own boundaries, and had a lot of flexibility being single/no kids, but that's also a loss as well, and certainly not something to aspire to.

Do I look at the younger folks today with a little twinge of envy that the world and resources are much more available & accepting? Absolutely, I don't think I'd be human if I didn't, but by that same token, constantly thinking "what I should I have done differently?" is bad in the long term. We're not all on the same part of the spectrum, either, so I think answers are going to be different for everyone.

[Glenda58]

I wouldn't have gotten married a third time. Not purged all my things. And maybe even transition to be Glenda full time.

[TheHiddenMe]

About 20 years ago I told my wife I wanted to get some woman’s clothes (she already knew I was interested in dressing). She bought me some things, like a dress and a wig and shoes at my request (I was reluctant to buy my own stuff). I started dressing at home, and began to shop for myself.

It took another 15 years to build up the courage to venture out on a regular basis.

In the meantime, the public evolved so it became more acceptable to venture out dressed. While I wish I had started going out earlier, perhaps my reception would not have been as welcoming.

Fun to think about, but absent a time machine, impossible to change.

[Veronica Lacey]

If the Wish would come true I wouldn't wish to do anything differently as then I may not have met my wife and enjoyed the good life that I so far have.

But...for the sake of casual discussion and it's a fun little topic...

Maybe slide it back 30 years prior to meeting my wife and I would have tried to explore more of the community prior to laying down roots and becoming established in life. Sure, we can generally always make a change any time we want. Having said that it would have been easier and a lot more fun to explore the cd world as a 20-something had I realized that anything was possible back then.

[MissSixties]

came out a little earlier to my new wife - she's good now so cant complain and the other thing....be patient and organize to mine or buy about 1,000,000 BITCOIN for about $100.......

[MonicaPVD]

The biggest challenge wasn't so much who I was twenty years ago, or what my mindset was. Rather, the world was a very different place, not very open or accepting when it came to unconventional gender expression. Now, if I were 20 years younger in today's society, my oh my the things I would do!

[Cheryl T]

Let's push that back say 50 years or so.
If I knew then what I know now in all honesty I would not have gotten married. I would have pursued this avenue to a much greater extent and in my heart believe that I would have begun to transition many years ago.
But all that is for another life, a parallel universe or some episode of the Twilight Zone. As the saying goes, "If wishes were horses then beggars would ride".

[oh to be rachel]

Wow, the options that could have happened.
I could have been a woman by now.

[DanielleCD]

For me the change would have been 30 years ago... before my first marriage.

[Christie ann]

Let’s just say that if I knew what I know now at 20 years old, I would have tried to transition. We just didn’t know and thought we were alone. And now, it is not fair to my wife for me to come out and say I want to be a woman.

[JustJennifer]

20 years ago, I was certain that my desire to dress was long gone and never coming back. Regardless, I should have been more forthcoming and upfront about it before I got married. But I assumed the past was the past, so I kept that piece a secret. In retrospect, that was a mistake.

Honesty makes things a lot simpler for everyone, because everything comes out eventually, and it's one less story you have to keep straight. If your SO were to find your past to be unacceptable, the present is already on shaky ground and the future is even worse.

[Geena75]

Twenty years ago I hardly ever got dressed beyond a pair of pantyhose once and a great while. If I knew then what I would be doing today, I probably would have sworn it off and vowed never to do it again.

[fun4metoo2004]

To start with, I would have watched my weight/shape better. Committed to dressing without worry. kept my hair so i could grow it out. I shaved my head and am trying to decide if I want to grow it out again.

[Lacy PJs]

Not sure that many things would have changed but for one, there are certain clothing items that I would have "stocked up" on if I knew that twenty years later, they would be pretty scarce.

I have yet to find a good replacement for Sears Cling-a-lon thigh tops and really nice sheer peignoir sets are nowhere to be found today. But twenty years ago... they were already going out of style. :(

Lacy PJs

[Jenni6521]

I would have never purged as often as I did over the years. I still miss a sexy lace black bra, that fell victim. If I had said that in the beginning of this post I may never had written all of this other stuff.

I am in the same position as many, 20 years, is not a long enough look back. When I was in my mid-teens it would have been the beginning of the eighties. That was not a good time to be open and anywhere on this spectrum. I think then was the closest I have ever really considered wanting to do more to transition into a female. Then I had not discovered that my depression was also linked to gender dysphoria. I was not accepting of myself, and still struggle now, but time has made me better. I married young in life. Actually, today is our 36 anniversary. I think first I would have approached this with her more like I just did last week. There is a difference in discussing and then DISSCUSSING. Then she had participated and was more accepting, and I dare to say had a different perspective on the subject. I would have understood that my crossdressing was something that became hard wired in my frontal cortex and that over time it would change, wax and wain, but would not go away.

[Helen_Highwater]

It's interesting to read replies that talk of not getting married, of pursuing a different life path but as others have pointed out, things were different back then and to live full time would have been a far more difficult thing to do. Recent societal changes have made coming out so much easier and for me the upsides of being married are not things I'd throw away lightly. Our partnership has given us a comfortable life that I'm unsure I'd be enjoying had I lived a single life plus I'd have missed out on two wonderful children.

So what would I do differently. Looking back I can see there were opportunities were I could have been more open with my SO, certainly early on in our relationship and so a better understanding of myself could have given me the confidence needed to "Have the talk". Just to be out of the closet to my SO would have made a huge difference but that also assumes that she would have been accepting of that in the relationship as we raised a family.

All that said, it is what it is and I need to focus on the here and now while looking forward and re-evaluating now we're empty nesters just what to do and is now the time for that talk.

[Di]

I find it fascinating to read everyones answers.
Over the past few weeks we have had many more join here. I think maybe it might be with the New Year and reflection on your life.
Cross-dressing is a unique gift and a part of you . Do not fight it and accept yourself and you will learn how to use it in the best possible way to lead a happy life.
My advice for those not married yet, be open and honest learn from those here that 20 years ago ( for different reasons) did not. Makes a much easier life for everyone.
Great thread, and all the newbies can learn from it.

[Giselle(Oshawa)]

At age 66 i would need to go back 50 years to open up to my family about my gender issues.
Pretty sure they would have disowned me.
I would have rather been disowned at age 16 than the hell i have put both myself and my
wife through.

[Wendy-Lyn]

20 years, eh?
Well, I'm 64 now (just) and around 25 years ago my life turned to hell in short order and I lost almost everything I had, including my self-respect, and my desire to have any sort of relationship simply evaporated. It has only recently returned - and with a vengeance.
So, to the question - what would I have done differently?
I've given this a bit of thought, and I think I'd have probably bitten the bullet, come out, and transitioned.
I think I'd have been a much happier girl today if I had.

[AnelineM]

If I could just call or email my 20 years ago self, I'd say forgetabout purging. You're not going to quit dressing up. And, SELL ENRON!

[Raychel]

It would have to be more then 20 years ago for me
18 years ago I told my then wife. Not much has changed since then. I separated from my wife. But that is about all

30+ years ago, I would have accepted myself more.
I would have still been very careful who found out and who knew. I was a very well known business man. And had to be very careful about family reputation.

But knowing how my wife and kids accepted. That part certainly would have happened sooner

[Kitty Sue]

20 years ago was a good time for me with CDing. However, I also wanted to return to the military which I did, necessitating a return to the closet until I eventually retired.

[Sabine Janus]

It would go back more than 20 years, but I was dating a nurse from a big city who was hinting around she wanted to see me en femme and do a drag show in her gay neighbors apartment they every so often.

I would have let her do any old thing she liked dressing me up.

[CynthiaD]

I’d have to go back 60 years. I’d tell my 13 year old self:

1. Don’t ever drink alcohol. (I’m a recovered alcoholic).
2. Don’t ever smoke.
3. Wear a dress every day.

Number 3 would not have been possible though. Actually I would probably go for a much longer explanation, like: you’re female. You’ve always been female, and always will be. It’s the best part of you. You can’t do anything about it now, but the time will come when you can. When that time comes, embrace it and be proud.

[Lisa Gerrie]

Twenty years ago? "Save time, just get divorced now."

[Rachel Anne]

What's the old joke? "Why get married? Just find someone you hate and buy them a house"

[Rikidee]

I would also have to go back more than 20 years and in reality would not want a do over as I am somewhat happy where I am.

What I think about a lot is that when I first got caught dressing by Mom at 5 years old I should have continued to dress and get caught until they gave in. It would have been tough for a while but I think if I had helped with housework and other chores she would have accepted me as the girl she never had.

[stephenie3756]

I would have to go back 30 years ago and have found a different woman to marry. Been married for 29 years now and in DADT. There was one point when i got to dress in the open, but that was at least a decade ago. Yes, i did not disclose my cd to my wife at the beginning. I would find a woman who would accept me as a cd.

[1Ladyjade]

The only thing I would do differently is find a partner that would support my CD. I thought I did. When she was young she was known as the fag hag. She only hung out with gay people. I didn't know my urge to CD would come back as strong as it has. So I never asked her. I shaved my legs cause I wanted to get pictures of myself in femme. She threw a fit. Said she hated the feeling of my bare legs. She said she knows she is definitely not lesbian. So I still have work to do to get her to support my CD. Until then I have a friend that has given me an outlet for my desire to be dressed femme. My cloths and make up are in her house. I have a key and any time I feel the need to dress I can drop in and put on Jade.

[Lacey New]

Oh well, I think we all look back at our lives and think of points where we woulda, shoulda, coulda done things differently and I guess in my imagination, things might have been better. But I don't and will never know. The only thing that I might have done differently would have been to exercise a little more discretion in purging. Who knew that you would not be able to buy a nice garter belt or garter stockings in a departments store? Or that Vanity Fair would stop making nice floral print briefs? I could go on and on.

[Genifer Teal]

Do everything sooner! I think we're going to see a lot of this sentiment here. When we're young the Fountain of Youth is overflowing. What we don't see is all the youth being wasted. We need to make the most of it while we can.

[il.dso]

20 years ago I wouldn't have deluded myself into believing that I would no longer be crossdressing in 20 years...

[Paula_56]

I would have tried living as a woman, began transition.

Deep down I think I would have been happier and more complete living as a woman and a wife

[Jessica Secret]

20 years ago I was a kid lol but I don't think I'd change or do anything differently, really happy how my life and CD'ing has worked itself out over the years. I'm in a good place and have been.

[julia.bowie]

I'd do everything different!

[Linda K.]

I would bet heavily on all the Super Bowl winners!!

[Felicia M]

Oh my.....twenty years ago I was just about to leave a long-term relationship and was single for the first time in many years. I have often thought about that time frame looking back. I found myself in a new city with a new career, absolutely no friends and an enormous amount of free time on my hands. I would give anything to go back to that point and do it over again.
I would have done almost everything differently.


I would have gotten a full professional makeover immediately to get a real sense of how to transform myself
I would have purchased a full makeup kit. I purchased some makeup at the time (and of course purged it after I started dated another woman full time) but knowing what I know now I should have purchased everything I could get my hands on lol!
I would have purchased and tried on as many outfits and shoes as I could possibly get my hands on and I would have went to the actual store to make sure of sizing and style
I would have gone out as Felicia to LGBTQ friendly spots as often as possible
I would have dated both men, women and t-girls to explore more of my sexuality
I would definitely have considered transitioning

It has been a life altering experience to figure all of the things above that I should have done then almost exactly twenty years later. Life has a way of doing that to you so I can look back now and know what might have been but also realize it was not to be. I love what my life has become but there is no question my life would be profoundly different if I had could go back to that time frame and had the opportunity to do it over again.

[Natalie5004]

Well it would have to be over 40 years ago for me.

2 words: Marriage knee

If I knew then what I know now my live would or at least should have been very different.

[Beverley Sims]

Knowing what I know now I would have continued the hormone treatment that was prescribed for quite a different ailment.