10 Crossdressing Questions

[mrpropel]

I should probably answer my own questions.

1 What's your sexuality?
Bi-Sexual
2 How often you cross-dress?
I'd say at least once a week usually.
3 When and where do you usually cross-dress?
Only at home currently
4 How old were you when you first started cross-dressing?
I think around 14 or 15
5 When you first started cross-dressing, who's clothes did you wear?
I made my own out of shorts and old clothes and stuff. I also stole a couple of clothes but it's all good :P
6 Have you ever been caught cross-dressing?
Not to my knowledge
7 What's your favorite cross dressing clothes to wear?
Short dresses and rompers for sure! Anything slutty really
8 Have you ever tried to quit. Or purged ( threw out all your clothes) before?
I've thrown out some clothes before but never just straight purged
9 Do you care if you pass or not?
Currently no but I wish I could pass. One of my dreams is being able to pass and then getting fucked while passing. Soon.....
10 Would you go through with a sex-change? Why / Why not?
Probably not, I would go through as far as to the point being classified as transsexual but not female. I think that's where I draw the line.

[Alcd87]

1 What's your sexuality?
straight

2 How often you cross-dress?
Several times a week
3 When and where do you usually cross-dress?
At home, I'll wear girly underwear when out sometime so long as it's well covered

4 How old were you when you first started cross-dressing?
Not sure, 13 or 14 I'd guess

5 When you first started cross-dressing, who's clothes did you wear?
My mother's, bras and panties then a evening dress

6 Have you ever been caught cross-dressing?
I think so a few times that I didn't intend. Not long after I started I had a pair of my mum's panties I'd tole that id hidden, they disapered nd shortly after she pit an evening dress in my wardrobe for storage - I think she knew
Second time recently now living by myself in the sand village as my parents I was goung to check on thete house while they were on holiday, as it was dark I got dressed up in a black snd white prom dress. As I walked up the drive there security lights came on, I was no longer hidden in the dark, I moved as quick as I could for the door and as I turned arround saw s neighbor walking away from thete window. A few weeks later when visiting the neighbour she had some dresses out and said "don't think there will fit you" ... I was so embarassed,

7 What's your favorite cross dressing clothes to wear?
Anything thst looks girly and gives me a feminine shape

8 Have you ever tried to quit. Or purged ( threw out all your clothes) before?
Yes several times but doesn't work

9 Do you care if you pass or not?
Nope I can't and don't try

10 Would you go through with a sex-change? Why / Why not?
No not interested in being a girl

[LimitExplorer]

I'm bumping this thread because I like the questions.

1 What's your sexuality?
Straight/bicurious.

I know for a fact that I like women. Every time I've fallen in love, it's with women. I've never been aroused by a man's body. However, if i'm horny enough, I get really interested in the idea of giving a guy a blowjob sometime...
But the thought of kissing or loving a man in any other way does nothing for me...

2 How often you cross-dress?
Depends on my arousal. If I abstain from masturbation for a while I do it a lot (whenever I'm in private) and tend to combine it with other kinks such as chastity or diapers.

During the winter I pretty much always sleep in women's pyjamas or nighties. I don't think I even own any male sleepwear anymore!

3 When and where do you usually cross-dress?
At home, when I'm in private (I live alone so that's pretty much always).
Sometimes I also like to wear lingerie under regular clothes while I go to work or grocery shopping or something. Panties, stockings, garter belt... Maybe a bra as well, but it's usually a bit too obvious under my T-shirt.

I'd also like to see if I can wear some women's exercise outfits (yoga pants or the like, sports bra under my shirt) when I go for a walk or go to the gym, but I'm not sure if it'll be discreet enough for my tastes

4 How old were you when you first started cross-dressing?
It's hard to say when it started because I rolled into it a bit. I honestly think it might be from seeing lots of hot women in lingerie online and having no girlfriend of my own to see in that sort of clothing. I was horny one night when I was about 24 years old and just bought some panties online. A bit later I also bought some matching bras, as well as bathing suits (I love one-piece swimsuits!). A bit further down the line I started buying some skirts & dresses as well, and then I splurged on some proper breast forms. Eventually I also had a shopping spree on AliExpress and bought some cheap wigs that I haven't even used yet, heels/heeled boots that fit my big feet, and lots of dresses and swimsuits that don't fit me that well... Now I have more clothes than I can fit in my closet and definitely have more female clothes than male...

5 When you first started cross-dressing, who's clothes did you wear?
I remember as a kid I had some interest in my sister's underwear, but that wasn't really crossdressing.
Other than that, I always wear my self-bought clothes.

6 Have you ever been caught cross-dressing?
No, but I did eventually tell my mom that I liked it. She was cool about it. Mostly just honored that I would confide in her about it .

I also had some of my AliExpress orders delivered while I wasn't home, and the postman delivered them to my neighbor. The parcels weren't very discreet, they'd often say something like "Sexy nightgown" or "Sexy underwear" on the import label. If she bothered to look, she probably got a pretty good sense of what was happening (especially because she received like 6 packages for me over the course of a week...)

7 What's your favorite cross dressing clothes to wear?
I love nightwear. Pyjamas, nightgowns, slip dresses... They're usually super comfy, super soft, and nice pastel colours (read: pink) that you won't get in male nightwear...
I also love dresses. They're airy, it's super feminine, and it gives easy access to your lower body if you need it, wink wink.

8 Have you ever tried to quit. Or purged ( threw out all your clothes) before?
Not with crossdressing. In fact I should really get rid of some items that I probably will never wear, but it's hard...
I went through purge phases with diapers earlier in my life (around 17 years old). After an orgasm I'd feel disgusted with myself and lose all interest in diapers, and suddenly realize that I had no good place to hide them from my parents. I threw away a lot of unused diapers back then.
Eventually I learned that the interest would come back, so I stopped myself from purging. These days I still lose interest in my kinks after I orgasm (don't we all?) but it can come back to me in a matter of minutes, and if it doesn't, that's fine too - it'll come back eventually, even if it takes months.

9 Do you care if you pass or not?
Not really. I would love to pass, but I know I don't - I never wear a wig, I never do make-up, and I have a beard.
It's still a goal of mine to one day learn some basic make-up and wear a wig to see if I could pass, but I think I need to work on getting a more flattering feminine body shape first.

10 Would you go through with a sex-change? Why / Why not?
I've fantasized about it, but I'm reasonably sure that I'm not transgender. If gender is a spectrum then I'm definitely not alpha male material, but in the end I like being a dude - I just love women's clothes and I love the thought of having breasts... But only when I'm horny.

[Asmodeus-]

1 What's your sexuality?
I am straight, I can never love a man as I do not find them attractive in that respect how ever I would worship the cock between his legs

2 How often you cross-dress?
Most days as I tend to wear panties every day and some girly clothes when I get home from work

3 When and where do you usually cross-dress?
At work and if I am on my own will wear a bra and breast forms or at home when alone

4 How old were you when you first started cross-dressing?
Quite young, around 9 ish

5 When you first started cross-dressing, who's clothes did you wear?
My mother's panties mainly

6 Have you ever been caught cross-dressing?
No I haven't but dressed up as one for Halloween

7 What's your favorite cross dressing clothes to wear?
Panties and a bra mainly and anything tight fitting

8 Have you ever tried to quit. Or purged ( threw out all your clothes) before?
I have thrown a lot out but mostly to make room for new clothing

9 Do you care if you pass or not?
Not really as I do it for fun and not for others

10 Would you go through with a sex-change? Why / Why not?
I don't do it because I want to be a woman but because it is a fetish that I enjoy doing

[O yeah]

1 What's your sexuality?

Bi-sexual, however I only enjoy being emotionally attached to women

2 How often you cross-dress?

Here and there, recently moved out so hoping to dress more

3 When and where do you usually cross-dress?

When I’m home alone or on vacay, I love to travel

4 How old were you when you first started cross-dressing?

Hmm, maybe 13?

5 When you first started cross-dressing, who's clothes did you wear?

My step sisters

6 Have you ever been caught cross-dressing?

Hmm don’t think so, some close calls though

7 What's your favorite cross dressing clothes to wear?

Probably my school girl outfit, although I really like trying on new coutfits

8 Have you ever tried to quit. Or purged ( threw out all your clothes) before?

Yeah, when I was younger but I’ve gotten past that now

9 Do you care if you pass or not?

I try to be as passable as possible

10 Would you go through with a sex-change? Why / Why not?

No, not something I’m Intrested in, I enjoy living my life as a male

[EnigmaticBunni]

This one is for all the cross-dressers of get dare(me being one of them). Here's some CD related questions.

1 What's your sexuality?
bisexual

2 How often you cross-dress?
depends. usually about once a month. more often if "motivated"

3 When and where do you usually cross-dress?
around the house when i am alone or my wife is interested

4 How old were you when you first started cross-dressing?
about 15

5 When you first started cross-dressing, who's clothes did you wear?
my sisters then got my own

6 Have you ever been caught cross-dressing?
yes

7 What's your favorite cross dressing clothes to wear?
maid outfit.. but then i crossdress for humiliation/degradation

8 Have you ever tried to quit. Or purged ( threw out all your clothes) before?
yeah.. but only cus i was made to

9 Do you care if you pass or not?
because I crossdress for degradation, it is a bigger turn on to not pass. besides I am bearded.

10 Would you go through with a sex-change? Why / Why not?
no. cus I'm male.

[Scrap]

1 What's your sexuality?
pansexual

2 How often you cross-dress?
as often as I can

3 When and where do you usually cross-dress?
most anywhere, but almost always at night. I have not gotten brave enough to do much in the light of day yet.

4 How old were you when you first started cross-dressing?
aside from the typical 'wearing mommy's heels' thing that I think most boys do, the first time I remember was around age 10, wearing my mom's pantyhose and occasional dress.

5 When you first started cross-dressing, who's clothes did you wear?
my mother's.

6 Have you ever been caught cross-dressing?
most of the times that I was seen crossdressing was because I wanted to be.

7 What's your favorite cross dressing clothes to wear?
depends on my mood. If I'm feeling slutty, I wear my slut skirt and a top. if I'm feeling 'respectable', I have a couple of nice business appropriate ensembles. I also have a couple of flirty sundresses.

8 Have you ever tried to quit. Or purged ( threw out all your clothes) before?
several times.

9 Do you care if you pass or not?
not at the moment, because I really can't. The best I think I can do would be the lady from Crocodile Dundee... or Patrick Swayze in "Julie Newmar"...

10 Would you go through with a sex-change? Why / Why not?
I have seriously thought about it, and I am honestly on the fence. I think it is too much of a change for me right now, but in the future, maybe.

[Diapered Devil]

1 What's your sexuality?
Bi

2 How often you cross-dress?
Once a month - used to be more frequent

3 When and where do you usually cross-dress?
At home now - used to occasionally venture out and about

4 How old were you when you first started cross-dressing?
About 11-13

5 When you first started cross-dressing, who's clothes did you wear?
Family members - Aunt/Mum/Cousin

6 Have you ever been caught cross-dressing?
Yup, never been more embarrassed, but nothing bad came of it (thank fuck we live in the 21st century).

7 What's your favorite cross dressing clothes to wear?
Well made dresses & Lingerie.

8 Have you ever tried to quit. Or purged ( threw out all your clothes) before?
Of course, with varying success.

9 Do you care if you pass or not?
I used to when i was more gender fluid. I used to be there or there abouts, these days i prefer drag looks haha.

10 Would you go through with a sex-change? Why / Why not?
Nope. I'm not thoroughly discontent with my gender, there are no guarantees that transitioning would make me happier, hormones can wreak havoc with body and mind, i dont know if i'd be satisfied with the end product, trans woman have to deal with so much prejudice and hate and I dont know if i could live that lifestyle 24/7.

[Kylie.j.96]

1 What's your sexuality? Mostly straight

2 How often you cross-dress? Almost daily

3 When and where do you usually cross-dress? Mostly at home

4 How old were you when you first started cross-dressing? Like 10

5 When you first started cross-dressing, who's clothes did you wear? Sisters

6 Have you ever been caught cross-dressing? Yep

7 What's your favorite cross dressing clothes to wear? First off bra and undies but any and everything

8 Have you ever tried to quit. Or purged ( threw out all your clothes) before? Nope

9 Do you care if you pass or not? Not really

10 Would you go through with a sex-change? Why / Why not? No. I like being a guy sometimes too

Thanks for answering! [/COLOR][/FONT][/QUOTE]

[LockMeSub]

1 What's your sexuality? Now I say I am Bisexual

2 How often you cross-dress? at least panties 5 days a week

3 When and where do you usually cross-dress? When my wife is a work

4 How old were you when you first started cross-dressing? probably 19

5 When you first started cross-dressing, who's clothes did you wear? My exwifes

6 Have you ever been caught cross-dressing? Yes by my Exwife

7 What's your favorite cross dressing clothes to wear? in my younger days All decked out with a mini skirt, nylons, bra, blouse, wig and makeup now more just a panty and bra kinda guy

8 Have you ever tried to quit. Or purged ( threw out all your clothes) before? Did quit for many years probably 30 and then I discovered Chastity cages and girl under thing just seem to be a requirement along with getting on my knee's to service real men

9 Do you care if you pass or not? I don't pass at all anymore but don't care

10 Would you go through with a sex-change? Why / Why not? I would in a heart beat I have alway thought I should have been born a woman but wasn't