Can I ask about cross dressing men... why do you do this?

Question

My brother is a cross-dresser. I found out about 3 years ago. I'm 33 and my brother is 52.
He is a mans man. He's rugged and does things men do. But a few years ago he told our family that he has been doing this since he was a teenager.
He remembers trying on lipstick and mom's nylons when he was under 10. (parents caught him)
So now I'm in this world that I know pretty much nothing about. I love him very much and I accept him 100%. (When he's all dressed up he looks like he's in his 30's and gorgeous). His name is Valerie. I feel like I have a brother and a sister. I am confused about all this and even though we have had long conversations I still don't really understand (I don't think he truely does either), so I need some more info...

He has had thoughts of gender reassignment, but isn't sure about if he wants to do this. He has long nails and tweezed eyebrows. Most of his close friends know but the majority of our extended family does not. He's a master carpenter (which confuses me further).
I guess my questions have to do with why does he feel this way?
Do I have the right outlook on this (sometimes he's my brother when he's not dressed up and a sister figure when he is)?
Does my viewing it like that make him seem like a split personality because he's not- he always feels like a woman?

My brother is very attracted to women- in fact he's married, well separated- she left him. He is not by any stretch of the imagination, gay.

Just for the stupid idiots that may answer- my brother is not sick.
I would defend him with my life.
So if you intend to leave a hate message- don't!!!!!!!!
My brother is more normal and better and smarter and more successful than all the "men" out there that are scared of honesty and their own sexuality.

Answer 1

There are 3 types of cross-dressers:

-Transvestites, straight men who wear women's clothes, usually as part of a fetish
-Transexuals who believe the are in bodies of the wrong gender
- Drag queens - enetertainers who cross-dress for shows

If your brother is straight and still has an active sex life with women, he is most likely a transvestite. Prevailing opinions are that transvestites feel "at home" in women's clothes because in them they are allowed to express a side of themselves (tender, nurturing, feminine) that society does not allow them to express in their men's lives. Not surprisingly, the most macho men are usually in this group, firefighters, policemen, and yes a master carpenter would fall right into this category.

If your brother has had *serious* thoughts of gender re-assignment, he could be a transsexual. It is unusual for transsexuals to have active sex lives with anyone, as they tend to find their own genetalia repulsive, or not fitting in with their mind and body image, and therefore embarrassing. It is possible, however, for transgendered men to be married, and some stay married through the entire process of gender-reassignment.

The best way to find out is to talk to your brother. Find out what he really wants, what his feelings are, and what his goals are for his life. The one thing that I KNOW he'll want and need, though, is your love and support. You are a great sister for not rejecting him, and wanting to know more. Yes, it is possible for him to have a happy life, many cross-dressers are happily married, and have satisfying lives.

If you're feeling adventuresome, "Gender Outlaw" by Kate
Bornstein is an excellent book on gender identity, and the undue importance of same in society. Be warned - she will challengeyour pre-conceived notions, but then I guess they have been challenged already, haven't they?

On cross-dressing, try reading "Alice in Genderland" by Richard J Novic, MD

If your brother does turn out to be a transsexual, I personally found "Second Serve" by Renee Richards an excellent read, and a good first-person account of that transition and the struggles.

There is also an excellent website you can check out: www.heartcorps.com/journeys/

It really sounds to me though, like your brother is just a cross-dresser.

Thanks for being such a great sister to try to understand him.

Good luck.

Answer 2

Just sounds like he has a fetish. If he remembers doing it when he was young, then that's probably when it was imprinted into him.

It's sort of like spanking, if you get spanked as a kid, you have a higher chance of having a spanking fetish when you're an adult. The imprint is made in childhood.

A lot of fetishes are imprinted in childhood.

But chances are as well that something triggers it. Likely if he's feeling stressed, or caged in, he uses this as an escape.

Because when he gets dressed up as Valerie(I assume this is his female name, pardon me if it is not), he's no longer the same person, the troubles of his male life vanish. He no longer feels the burden of responsibility that he has while male, because Valerie isn't a complete person, she's a mask.

Think about it like if you go to a costume party, with a full face mask. You can be any person you want, because noone can see you, you've put on another persona, your old and real persona no longer matters as a result, because you have a new and clean slate to work with.

So I would doubt he wants a sex change, he likely just wants some escapism and fetish play. Leave it at that.

Answer 3

If I were in your position, I'd start with cross dressing porn and while watching it, mention how much I was turned on by cross dressing, and let him see by hard/fast I came from watching it. Sorry to be so graphic, but that's honestly what I'd do. My husband's done some things before we were married, that he isn't into now, but he'll do almost anything I ask because he knows it's going to be worth his wild to fulfill my request. I don't just ask him to do things for the hell of it. I ask him to do things that I know would turn me on and once I get turned on, that's all he needs to dive head first into whatever role I suggest.

Answer 4

I am sex:Male and gender:Female - Transgendered.

Honestly, your brother is female brained. It's not unusual, over 1 MILLION transgendered people live and work in America today and 85% of the population now openly in 2015 accepts LGBT and gender identity different people. 1 in 4 men will crossdress and a lot of them do it regularly. The chances of you meeting one in your daily work life and during your shopping exploits day to day are 100% guaranteed. You have met them and you never knew it because they are very good at hiding themselves in the crowd. Only 2% of all crossdressers -- both male and female -- are gay. That means 98% of all crossdressers worldwide are 100% heterosexual. A guy who dresses up as a female usually goes specifically and only for women and vice versa for female to male crossdressers. It typically goes without saying they are interested more in a style than a lifestyle...

Next, if you're going to accept a crossdresser please, please, please start using the correct pronouns. Your brother is not a he...please use "she, her, hers and herself" from now on. Using the proper pronouns is important, because they show you are recognizing they are trans gendered whether they are in vogue so to speak or not. In that person's mind, they are female and all things female apply. If you don't address that person as they should be addressed or if you call them "It" you'll be instantly and forever labeled as a bigot not only by that person, but by everyone else around you even if you are joking and the distinction to say the least is pretty much permanent for the rest of your life.

Lastly, be open. The best way to broach the subject is just to be polite, courteous and honest about how you feel. If you don't like it, you may have to do some research in order to understand them, but "she's" not going away, it's a permanent mindset to be a crossdresser not a temporary phase and no amount of counseling, training or religio-socio-political intervention is EVER going to change the way she thinks. It's permanent.

That being said, there are things you can do. You can get her solid skirts, not flowery, not flashy, not tiered nor mini...something subtle and plain that she can wear out in public with a male top like a polo shirt and allow her to crossdress in public and present as a male on top. Many men do this and so it's not all that uncommon. It satisfies the urge and is typically accepted whether or not people actually like men in skirts or not. For me, I've never ever had any problems. Only the idiots in the world choose to act belligerent or irrational and so those people are few and far between. The rest of society is typically very social and I've made a lot of friends who before I had met them didn't like the idea of a guy cruising around in a denim skirt. Now, they understand and they only have good things to say about me...understanding another's personal preferences is the key to happiness and success ;-)

The world is changing...change with it or you'll be left behind...

Answer 5

There are tons and tons of info out here in "Cyber World" all about the Transgendered. But it's really so terrific that you're there with your "sister" when she needs to present that way. The best info about Valerie is going to come from Valerie as all of our situations are unique unto our selves. Sure there's lots of common experiences and if I'd hazzard a guess about Valerie's situation I'd say it was very much like my own. I coincidently am also a builder of things, wooden boats are my favorite, and when in male mode people would never guess that I can be Linda just as well. I describe myself as "Two Spirit"; meaning that I have to present as "not Linda" and as Linda at different times and am comfortable either way but not comfortable just being one way or the other exclusively. See if this idea resonates with Valerie. You're a terrific sister to her and she's very lucky to have you in her life.

In peace,
Linda

Answer 6

it's comforting to read that you and your brother do sit down and have a nice chat about it. Communication is the best help and support you can give him.

i am not a cross dresser myself but i have friends that do. somehow they tell me that cross dressing makes them feel complete. it's the "a woman trapped in a man's body" theory.

Try to give your brother and yourself time to really understand the situation. A 52 yo man coming out to his family like this do really need a lot of courage. I believe your brother is mature enough to understand what is going on inside him. Give him trust and respect that's what he need most.

Answer 7

My take on this would be if like say if you liked to dress "gothic." I mean,it doesn't change who you are inside,unless he's transsexual,which would be different than just cross dressing. A transsexual would be a male who felt trapped inside his male body,who felt like a female inside. (Or vice versa) Cross dressers are simply that,men who like to wear women's clothing because they like it.It doesn't necessarily make them gay or bi,just like for whatever reasoning,to wear women's clothing. Hope this helps ya in some way...

Answer 8

ive always read that the majority of people who cross dress are heterosexuals. i believe your brother might be more in line with transexual from your descriptions. maybe a counselor should evaluate your brother as well.

Answer 9

Thats pretty messed up.
He must be F-ed in the head cause normal people dont do that.
What a freak of nature.
If you have kids i hope they never see him dressed as a woman, if he has kids thats a shame he's doing this to them its only a matter of time before they find out and then they will freak and if thier friends or worse enemys find out. what ridicule they will be forced to endure cause this MAN wears panties and a bra. FREAK

Answer 10

i guess he just wants to dress up as women, thats all. He's gay dude