100 Questions To Ask a Crossdresser

What to ask a Crossdresser

Getting to know someone who crossdresses can be a fun and meaningful experience, especially when you’re curious, open-minded, and respectful. Whether you’re a friend, partner, or just interested in learning more, asking the right questions can help build trust and connection. In this guide, we’ve put together 100 thoughtful questions to ask a crossdresser—ranging from light and playful to deep and personal. No matter where you’re coming from, this list is a great way to spark real conversations and better understand the world of crossdressing.

I will share my responses to these questions to kick it off.

How old were you when you realized you were different? Well I was 13 i think when I tried my first pair of stocking I did not feel different I felt guilty for the arousement I guess but since then a new exciting journey began
How old were you when you first tried wearing women’s clothes, make up etc? First item was a pair of pantyhose when I was around 13 as I wrote make up was at 24!
Have you ever told anyone you were a Crossdresser? If yes who? well for starters my wife…in the past some internet encounters
At what age did you come up with your femme name? Well here is a small story my old name Vicky I used it since 23…I changed recently to Emma
Did you use any other femme names before you chose your current name if so what was it? As I wrote I was Vicky in the past and for a small period Aphrodite
How did you come up with your Femme name? Well I posted a poll here did not you vote?
Have you ever been caught dressed? Not from persons who did not know,my wife caught me but she knew so it was kind of messy but we solved it
How did the people you told take it? Well one married me os I guess surprisingly well
Are you married? Yes
Does your spouse know? and if so are they accepting? Yes and yes
What was the first article of women’s clothes you ever bought? I have bought when I was 22
What was the last article of women’s clothes you bought? 5dresses and high
Long or short skirts? I prefer a dress over a skirt, but I’d say short
Do you venture out dressed? No never it’s my dream know i guess
If you could go back and change one thing about your Crossdressing what would it be? Well having more.fun as a girl much sooner with no hesitations and keeping in touch with people who met me as a female
Do you feel being a Crossdresser makes you a better person? If yes how so? Better I don’t know ,stress free with no worries and just thinking of cocks and sex makes me relaxed when in femme
How long were you dating / married before you told your significant other or spouse? 2 days
What is your favourite article of clothing? I guess secretary style pencil dress high heels provocative 👚
If you have bought your own clothes, have you ever had any issues with store clerks? I buy all my stuff online.And when I bought on a store I didn’t I was shopping for my girlfriend as far as they knew
What is your greatest Crossdressing accomplishment? Balancing the 2 lifes is not easy also trying to look passable it’s a hard and expensive task I am glad with my progress to these tasks
What is your favorite brand of make up? As I haven’t mastered the use of makeup, and am still a novice , I really don’t have a favorite
Do you wear perfume? If yes what is your favorite fragrance? Not yet
How many lipsticks do you own? 6 or 7
What is your favorite colour of lipstick called? 💄 don’t know that I don’t want to use my mind for anything different than cocks as emma:)
Did you buy breast forms or do you make your own? Bought breast forms and a breast plate too and I am going to buy a new one soon because the last one is teared on my disappointment
Do you ever have dreams related to Crossdressing? if yes what was it? Many times I day dream as a girl but dreams as a femme a few that ok I write them down as stories lol
When not dressed how often do you think about it, for example while at work? Multiple times throughout each day I am at work now!!!!
Favorite hair removal method? Well tried a cream did not smell nice but got good results i hope you see
If you could spend a day with anyone else dressed who would it be? My wife as a man or i take offera from the girls here lol.
Do you have space in the closet for your clothes or do you have to hide them? Hide them in a suitcase expect my panties in the drawer
Have you ever purged your clothes? Yes to my regret 2 or 3 times
Given the opportunity would you take a job where you could work as either your male or female self at any time? It depends the salary and the perks 😉
Do you paint your natural finger nails or use fake ones? I’ve done both
What color do you like to use on your finger nails? I like red or pink
Do you keep your toe nails painted? No but would like to
What color nail polish do you like best on your toes? Again red or pink
If you wear make up what part do you find the hardest to learn how to do? Well I like to look completely real and feminine so everything but I keep on trying
Have you ever had a professional make over? Yes and the result was very good but deleted the pictures!!!
Have you ever worn a Bikini or other swimsuit? No
Do you own or have you ever worn a Wedding Dress? No
Do you own a wig or use your own hair? Wigs
How often are you able to dress up during the week? On average once a week when I work from home and I’m alone.
How many Blouses do you own? A few blouses
How many Skirts do you own?around 10
How many Dresses do you own? Well over a dozen
How many bra’s do you own? 8
How many pair’s of panties do you own? A dozen or so
What is your favorite color for lingerie? black red and pink recently
Pantyhose or Thigh Highs? I love them equally
Favorite place to shop for misc items? Amazon is guess
Favorite place to shop for Make up? Eshops
Favorite place to shop for clothes? Amazon, Shein, temu
Favorite place to shop for Lingerie? Shein
Best time you can think of spent dressed up? The night i got my makeover
If you could have the ultimate day out where would you go? Probably to a town/area that is very progressive and I would love to do this with some other CDs and friends from here
Funniest thing that’s ever happened to you while Crossdressing? Got more excited than I imagined from a dildo and got it little deeper than I should i guess 😉
Do you have pierced ears or wear clip ons? Clip ons
Do you wear heels? Yessss!!!!
How long did it take you to learn how to walk in heels? Still trying to master it
How many pairs of heels do you own? 7
Name an article of Women’s clothing you can’t live without?high 👠
What is one article of Women’s clothes you don’t like? Well since I am girl.with curves too tight don’t really suit me
Do you sleep in a nightie? Not anymore
What type of panties do you like? All kind of panties that highlight my perky ass I guess
What is your Favorite color for a dress? Black red green purple
When you’re wearing pantyhose, what do you do with your junk? Let it be free or tuck it up and tape? Free as a bird
What stops you from ‘dressing’ in public? Fear of yourself or of others? I think I must look female for sure and passable as hell don’t want to be recognized by anyone
When did you first know your taste in fashion was different from other boys? Well never really thought about it
When did you tell your wife? What was her reaction? When we first met she was horny as hell for the whole think
What would you tell your 5 year old self if you could? Nothing creepy question
Do you shave your chest and armpits as well as your legs? I only have to shave my legs and genitals i am pretty hairless
Have you ever told anyone and they reacted badly? Nope
What was your most surprising reaction when telling someone? Never got anything surprising
For most women, taking the bra off at the end of the day and having a good under-boob scratch is the equivalent to a man scratching his nut-sack. Is it the same when you take off your bra? Nope
How did you feel the first time you ‘dressed’? Awkward and confused. I did love the feel of the clothes though.
How did you feel the last time you ‘dressed’? Horny and slutty
Do you and your wife share clothes? Nope
What do you wish everyone understood about why you dress that no one seems to really get? Don’t really care,I believe I should focus on me and how I feel
Do you prefer skirts and dresses or pants? Well skirts and dresses i have a few pants
How do you hide your 5 o’clock shadow? Concealer
If you could go somewhere on the planet where not one soul knew who you were and publicly dress, would you? Without a doubt.
Do you think you’ll ever tell your children? I think never
What will you tell your children (if you don’t intend to tell them) and they find out accidentally? There is a fear I didn’t have until now
Why aren’t women who wear menswear considered cross-dressers? Well its just label…I don’t feel crossdresser when in femme I feel Emma:)
Where the hell do you find shoes to fit? Shein Temu
What is the longest you have ever dressed for? A hole day
Do your bra and panties have to match? Nope
Do you find there is a big difference between your male and female self? Yes I am far more.logical as a male and far too careless and bimbominded as a slut sorry femme I meant
Does it matter to you if you “Pass” or not? Yes alot
Do you “Pass”? Not without make up
How long does it take you to get all dressed up? 1 to 2 hours
If you had a chance to remove your desire to Crossdress would you take it? No, come on would you like me to…world needs Emma 😉
Do you have any female role models and if so who are they? Many around my age 40’s that is
Do you listen to anything while getting ready? I enjoy listening to anything or sissy hypno
What do you hope to accomplish by Crossdressing? Perfection to my feminine side
What do you expect crossdressing to teach you about being a woman and the experiences associated with it? Everything but it depends on me.though and how much of these I am receiving
Do your personal or political views change as a result of the experiences of crossdressing? Not at all because they are always about equality and acceptance.
Have your views on relationships changed with crossdressing in your life? I always thought people should be happy no matter who they want to be with. That hasn’t changed.
What was your best Crossdressing experience? Many especially with the couples were great I will cherish these moments forever
What was your worst Crossdressing experience? I met a couple once who wanted to video capture our acting and also asked me to pay for the hotel and only do what the woman wanted with no French kisses, I mean OK I wasn’t so experienced and looking as feminine as I am look now but I was pretty fuckable lol , they were impolite and with no sense of humor as well so a first date that really was a last date that was