Biggest Challenge

[Di]

Reading an article it stated
The Cross-Dressers biggest Challenge is Acceptance. Be it loved ones, work ect.
I am hopeful that is changing :)
My question is regarding crossdressing what do you find as your biggest challenge?

[kimdl93]

My biggest challenge has always been self acceptance. That applies not only to crossdressing, but to most aspects of life. Kinda the “I’d never join a club that would have me as a member” syndrome.

[Teresa]

Di,
Believing you can do it and keep doing it , that was my biggest challenge going full time . Dressing to the nines for a few hours is one thing but it's a different matter from the moment you wake till the moment you slip back to bed at night and you've done every thing in femme mode .

[RainbowDash]

I've had no problems with anyone I've told I was a crossdresser. A couple people in my family, my dad included, do not think it is right for a man to be wearing women's clothes, period. There are a few girls at my work, whom after I decided they were nice and would most likely be understanding, told them I was a crossdresser. They've all been supportive and do not look down on me.
As far as going out dressed up en femme, I am not quite ready for that, because I know most people will not accept it. However.... I did just recently come out for the first time, although I am not sure if this counts. I went to Scarborough Renaissance Festival and dressed up like a fair maiden. I did this because I knew that there were lots of men who dressed up as women at places like these, so I knew this was my opportunity to shine. I went with it, had fun, and not a single person judged me or even looked at me funny. Hopefully in the future I will be accepted when I go out in public in real clothes and not just a costume.

[Chrissy647]

Self acceptance at this point.
It?s an odd feeling that feels like I?m not fully in control of myself.
I mean I got woken up at 3am with such strong urges that I ordered a pack of women?s underwear there and then.
And now I wonder why I did it.

[Tracy Irving]

When it comes to crossdressing, I am always challenged when searching for a dress that fits me perfectly. So, I look for skirt and blouse options but have very little coordination ability.

If I end up doing more than crossdressing, don't even get me started on makeup!

Weight loss is also becoming more challenging as I age.

[Lana Mae]

As a crossdresser, Self acceptance! Can I be the woman I want to be! A transformation proved that I could and here I am a trans woman! WOW! Who would have thought? LOL Hugs Lana Mae

[Leslie Langford]

Finding acceptance from a wife or an S/O.

I recently did some re-cluttering and came across a collection of old newspaper clippings that I had saved over the years of "Ann Landers" and "Dear Abby" columns dating back to the early 1990's that had dealt specifically with crossdressing. Yes, the writers were generally defending their "hobby" there and were seeking to educate both the columnists and the general public about it, but the overall theme invariably was sadness over their wives' non-acceptance and society's overall disdain for them.

To some extent we've made some progress in this area, but overall it's still the "same old, same old".

[Lori Ann Westlake]

Self-acceptance was my biggest challenge also. To be fair, unlike some others, I don't have a strong urge to go out and mix socially, otherwise I might have other challenges to face! Still, in my earliest days of crossdressing I felt a lot of shame and embarrassment, despite being alone. I can't put this down to anything specific I was "taught" by society--that it's "wrong" for men to do this, that I'd be seen as "gay," or whatever. I can't say I was "taught" anything at all. It was just the simple knowledge that if anyone saw me doing it they'd think I was "weird," "crazy" or whatever, and I'd be ridiculed. I do believe acceptance by my wife later on helped to further self-acceptance. for which I'm naturally grateful.

[Crissy 107]

Reading over the responses here I have to agree that self acceptance was the biggest hurdle for me in the beginning. It certainly took a long time and then after I got past that was to come out to my wife. That went well in the beginning but sort of went backwards after a while. I have to say that has been my biggest challenge for the past 7.5 years.

[Pixie_94]

Self-acceptance, at least if I followed what I have been told of embracing it as a part of who I am, but if you ask me the same question in other circumstances, I'd say either that I don't know much of what can be good quality and what is better not to purchase.

[Jacke]

To echo others, mine is self acceptance. I am a latecomer and am still learning. I am fortunate that my wife accepts, though does not understand. She is not a barrier to me. But I am. Even with her acceptance, I am still hesitant. That and my Covid beard will need to go in order to practice makeup.

[BTWimRobin]

Self acceptance was the first hurdle. The next mountain was my wife to accept this part of me. Two years after coming out to her I'm not sure where she stands or whether she even cares.

Di, do have a link to the article?

[Cass42]

Self acceptance and realizing I wasn't like any normal boy growing up liking to wear female clothing at times and later fulltime in my life.

[Judy-Somthing]

I would say My biggest challenge is not to ruin my marriage!

[Karren H]

Right now, it's having my wife turn off the TV or change the channel when ever there is anything at all to do with crossdressing.... Like tonight, 1/3 of the way through a Midsomer Murder episode (season 1, episode 2) and you can tell the guy that got murdered was a corssdresser... click.... sigh....

[Di]

I appreciate very much everyone taking the time to answer.

[candykowal]

Presenting as a feminine person while living 24/7/365 in fem has to be the toughest thing I had to do in controlling the masculine side, in my younger days.
Being made up cosmetic wise, more often, whenever I walked out the door.
It was not an option for me, back in the day, to look like a guy with breasts, I felt I had to be totally female.
I had a hard time doing things at the spur of the moment...I needed 10 minutes to check myself, change my outfit for the moment, perfume up, or make sure I take a purse with makeup and a razor.
Today is a bit different as I know what it takes and have only to dress to reminisce, in a 5 hour or less span.
Shopping, GNO's with friends, or just lounging at home.
Like Judy, trying not to ruin my marriage as "Husband First" is front and center.

[Aka_Donna]

Hard question to answer as more "biggest challenges".

Self-acceptance is the top, but followed closely by anxiety when discussing CD needs and then makeup, which is still a hurdle.

[Shelly Preston]

Di,
That is a great question.

I think the answer changes over time.

I remember finding time to dress was the biggest challenge.

Then it was stepping out the door.

Telling family and so it continues until you find yourself in a happy position.

Self acceptance has always been the biggest, as it affects individuals at every stage of their journey no matter the destination.

[Tammy P.]

Di,
I find my biggest challenge is letting go of the guilt. Not the guilt of being a cross dresser but the guilt of what I put my wife through.
She tells me she is OK with my dressing, she seems to be OK with my dressing but I still think about the damage I am doing such as limiting her friends, her ability to see family just every days things.
I get the impression from my wife that this perceived embarrassment for her is strictly my problem and she does not feel this way. Just another cross to bear on the journey.

[Maid_Marion]

My biggest challenge was accepting help.

Perhaps my biggest "tell" was that women graciously accept help and men decline.
If I'm going to present female I need to expect that people expect me to go first while they wait.
I need to be aware of my surroundings and do my part to make basic courtesies go smoothly.

Marion

[SaraLin]

My biggest challenge is <drum roll, please> BALANCE

as in balancing my inner needs/desires against the outer realities of my life.

If I could, I'd throw my "him" out, live every day fully in my "her" but my body, my wife, my friends, my *everything* all serve to pull me back towards "him".
It's a balancing act to stay in the middle - where I don't fall on the rocks to either side.

[Karen RHT]

My biggest challenge these days is maintaining my patience while waiting for my wife to hopefully understand the world won't think the worst of her if I join a support group or visit other towns while presenting as Karen. She's fine with me wearing anything I please around the house, but just can't seem to take that next step.


Karen

[Billie]

As far as going out dressed up en femme, I am not quite ready for that, because I know most people will not accept it. However.... I did just recently come out for the first time, although I am not sure if this counts. I went to Scarborough Renaissance Festival and dressed up like a fair maiden. I did this because I knew that there were lots of men who dressed up as women at places like these, so I knew this was my opportunity to shine. I went with it, had fun, and not a single person judged me or even looked at me funny. Hopefully in the future I will be accepted when I go out in public in real clothes and not just a costume.

I did the same thing, only at the one in Houston. Went right before Halloween dressed as a witch. Had a great time. Although my wife wasn't pleased that I choose that outfit for the trip there. I should have changed once I got there instead of driving hours like that, although it's deeper than that.

I've been trying to wear more women's clothes as I work with few to no one around. Getting used to wearing a bra for the day. I wish I could just wear whatever I wanted when I wanted.

[GretchenM]

Good question, Di.

Like others, in my virtually 76 years I have to say the biggest challenge has been self acceptance. I had no problem with that until I got caught playing with my mother's clothes and makeup when I was about 8. As a result of the reprimand (this was the first half of the 1950's) I not only went into the closet but into denial. Sixty years of it! That stance had a huge effect on my life's course. But once I surrendered and accepted that I was right in the first place true acceptance by others has been the challenge.

Tolerance is fairly easy to come by, but accepting me as being a type of transgender person is really hard for some. So many people, especially those more or less my age and older who just can't get to the point where they truly recognize that such an identity can exist. They are still locked into a gender binary concept and have a hard time accepting that this concept might be in error and in fact there can be people who naturally have a goodly amount of the "opposite" gender traits and characteristics that influence their behavior and sense of self in ways that don't fit the ideology. It is not really opposite in the way all of this works in the brain, but in terms of the gender binary concept it is easy to think of opposites. It appears there are just traits and characteristics and how they are blended in each person is unique to them. I think the old thinking is changing, but thousands of years of thinking that way will take a very long time to shift.

[Teri Ray]

I agree with others that the biggest issue I personally have with my desire to crossdress was gaining self acceptance. Lots of personal loathing and reflection on my behavior caused me to believe there was something significantly wrong with me. This forum and other internet information helped me get through it and only time and personal reflection caused me to accept that my desire was never going to change and it did not make me a bad person. And likely the biggest and most significant event in my life was the "big talk" with my wife and her ability to still love and accept me. Life became so much better having no longer to hide my desire from my wife.

[josie_S]

Here to echo most of the replies and say that it's been self acceptance for sure. so many purges and even bouts with depression but like Teri coming here and other websites as well as lots of reflection and therapy have helped me move toward acceptance and so I stopped purging and that alone feels like a huge feat

[Stephanie47]

Challenges come and need to be resolved. Life is a long journey. At 73 there have been numerous personal challenges.

As a teenager it was a trying to understand why I wore my mother's clothing on occasion. At the time society told me I was a homosexual although the terminology was brutal and vulgar. I was very confused. Lusting after beautiful starlets and neighborhood girls...gay? I got past that hurdle with self analysis. It took a long time, but, I am comfortable with myself. Yep, self acceptance.

As a husband with a developing cross dressing issue it was challenging for my wife and myself to develop and understanding and come to some agreement...Enter DADT. Fortunately, although my wife is not onboard with my cross dressing she does not say anything negative towards me or other men she encounters.

Another challenge, as stated several times on the forum, was my combat tour in Viet Nam. Trying to get past watching too many people kill and get killed has been a hurdle. I mention it only because cross dressing has been a source of comfort....escaping from the reality of being a male in the most adverse situation imaginable. Of course, now with women attached or in the combat arms in Iraq and Afghanistan...welcome to the club.

Some of these challenges are never 100% resolved.

[Krea]

Yes, the biggest challenge for me concerns acceptance: The fear of abusiveness, rejection, isolation by relatives, in-laws etc.
Knowing what i do of their general opinions, coming-out would surely be a disaster, so i keep my true-self hidden from them.

[XemmaX]

I guess dealing with shame that still comes back every so often. Which sucks.

[Cheryl T]

It used to be self-acceptance and all the guilt I carried for so many years.
After coming out to the wife and finding her fully accepting (after some time, tears and trials) I've been able to unburden myself and begin to love being me.

So, small as it may seem, right now my biggest challenge is eye makeup. My hand isn't that steady and I'm never satisfied with my outcome.

[kimdl93]

Cheryl and I have known each other...here...for a while. Where she succeeded and I failed is in building a relationship that could accomodate the person that she and I really are. Frankly, I admire what Cheryl and others have acheived in their relationsips and regret I could not do the same.

[prene]

Initially it was self-acceptance.
then with therapy I feel better about me

Now it is acceptance with GG's I hope to date. Have not found a gg who is accepting.
Now besides gg, my biggest challenge it making my voice higher LOL

[BTWimRobin]

I'm not sure if this is a challenge or not and it may even need it's own thread. This whole lifestyle (for lack of better terms), seems to consume me. It's always on the forefront of my mind and I am constantly thinking of new things I could try. I sometimes feel/fear I am falling too deep in the rabbit hole.

[Christina89]

My biggest challenge at first was accepting myself. But now it's just finding people in my life circle who I feel comfortable with coming out to about being a crossdresser.