I’m a 33 year old single male who crossdresses. I’m not a fulltimer, but I do dress in female clothing at least once a week. I also go out in public once a month. Fire away with any questions, and if any other crossdressers are here feel free to chime in!
Are you gay or one of the straight ones?
Do you actually look like a convincing woman? That is, do you think most people who see you recognize you as a crossdresser or not, at least past the first glance? (Not snarky; genuine question.)
Also, why do you do it? Is it just a “fun” thing, or do you feel more comfortable as a woman? If the latter, are you planning to have a sex change operation or cross-dress on a more permanent basis?
Valete,
Vox Imperatoris
Welp, let’s see… When you say “out in public”, where do you go? Is it a drag club, grocery shopping with your mom, or somewhere in between?? What kinds of reactions do you get when out in public… do you feel that you “pass” as female? If so, what do you think the secrets to passing are? If not, how do you deal with that emotionally? Also, do you consider yourself to be transgendered or not? Reasons why or why not?
I’m sure I’ll think of some more.
Also good on ya’ for coming out on the Boards and offering some knowledge! In my experience, this issue is one which needs MUCH ignorance-fightin. 
How old were you when you realized you enjoy crossdressing?
How did you figure out that you enjoy crossdressing?
When you’re dressed, do you feel like someone else (that is, like you’ve left InstallSLC behind for a while), or do you feel like you’re being yourself (that is, being the InstallSLC you’d like to be)?
Is the term “transvestite” out of favor?
I’d like to know why you started this thread.
How do you buy your clothing?
Do you only buy online, or do you buy from stores? If you do buy from stores, do you ever try things on for the fit?
This thread could be really interesting! I also crossdress as a hobby, and I’ll also answer questions if anyone likes. I’m a girl, so I could possibly give a different perspective.
Yes, sort of. Different people say different things, but in general “transvestite” is thought of as a term for a sexual fetish, and folks who crossdress for non-sexual reasons don’t want to be labeled as “perverts”. I don’t use the term for myself, because I think it has too many negative connotations.
I am straight as a ruler. I’m not really a convincing woman with my 5ft7 typical male frame, 190lb weight, and hirstute Hispanic complexion. Even after tons of foundation to cover my facial hair it’s not hard to deduce I’m a man.
Why do I dress? Part of it is the love of soft fabric like satin or nylon against my skin. Part of it is to express my more feminine side. I feel a lot less stress to live up to “real man” stereotypes when I’m dressed up. That being said I also love being a guy and never considered changing my sex. I don’t really think of myself a different person when I’m dressed, just me enjoying another side of myself.
When I go out in public, I go to gay clubs. I’m not convincing enough to go to mainstream clubs. Most people are amused or actively encourage me.
I’ve been crossdressing from an early age. I remember as a 7 year old trying on a bikini. Everytime I’ve worn women’s clothing since then I enjoyed it.
I buy my clothing from regular retail stores. Women’s clothing sizes are really confusing especially since I don’t have a women’s build. I usually try items on. I wear wigs because I don’t want people to know about my habits and I like being able to switch to my male persona quickly.
I don’t use “transvestite”, but it’s more because the word sounds so harshly Teutonic. “Crossdresser” seems more joyful.
Why did I start this thread? I can’t really talk about this to my family or coworkers. Plus with threads about vomiting and wiping your butt on this boards, what’s so shocking about crossdressing?
What types of styles do you like? Do you like dresses, or sporty/casual stuff? Bright colors? Professional/sophisticated; sexy; or frilly/pretty? Do you like high heels? Jewelry? Do you stuff your bra?
Have you shared this with any of your romantic partners/significant others? Does anyone in your life, like friends, know about it?
When you go to gay clubs, do you get hit on by men, and if so, how do you feel about that? Do you just tell them you’re straight?
Also, do you like women’s sleepwear at home or to bed, like satiny nightgowns or teddys, or lacy things, or even just a long, pretty flannel or cotton nightgown? As a woman, I love long, flowy, feminine nightgowns!
I have a question. I am 65, 5’11", bald and have a mustache, do you think a Teddy would be appropriate nightwear for me?
So if you had a good excuse to go for a satin suit and flouncy silk shirt (think rich male wear, France at the time of the last few Louises), would you like to give it a try? Do you think you’d like it?
Control top or stockings?
How do you source shoes that fit?
What styles do you prefer when not crossdressed? Do you wear fairly masculine clothes or a more androgynous/metro/fey look? Do you sometimes wear outfits that blur the line between crossdressed and not?
As one of the local board queers I’d like to thank you very much for starting this thread!
Is it that you want to dress as a woman, or is it that you want to wear any clothes you like, masculine or feminine?
Have any women in your life found it a turn on?
“Crossdresser” is Teutonic. “Transvestite” is Latinate.