16 Questions: CrossDressing

[EnigmaticBunni]

1. What did you wear the first time you crossdressed?
a bra
2. How long did you first wear it?
an hour
3. Where is the best place you've gone while dressed up?
peepshow booth
4. Did you usually cum after crossdressing?
sometimes
5. What colour is the clothing you like best?
black
6. Did you use any sextoys? Which ones?
yes many. usually chastity cage, plug or dildo
7. Have you bought more clothes to crossdress in since then?
yes
8. What do you fantasize about crossdressing in most?
Corsets
9. Bra or thong?
thong
10. Latex or fishnets?
Latex
11. Skirt or shorts?
Skirt
12. Pink or blue?
Pink
13. Heels or flats?
Heels
14. Blonde or brunette?
brunette
15. Makeup or Wig?
make up if i have to
16. Fake tits or natural?
natural

[Hertog]

1. What did you wear the first time you crossdressed? panties from my girlfriend
2. How long did you first wear it? 5 minutes
3. Where is the best place you've gone while dressed up? at home completely, in public always panties
4. Did you usually cum after crossdressing? sometimes
5. What colour is the clothing you like best? pink or purple
6. Did you use any sextoys? Which ones? dildo's ^^ vibrator, chastity cage, wand
7. Have you bought more clothes to crossdress in since then? lots...
8. What do you fantasize about crossdressing in most? dresses with matching lingerie, tights and heels
9. Bra or thong? oth
10. Latex or fishnets? Fishnet
11. Skirt or shorts? Skirt
12. Pink or blue? Pink
13. Heels or flats? Heels
14. Blonde or brunette?
15. Makeup or Wig? Make-up
16. Fake tits or natural? fake tits

[shyboy88]

1. What did you wear the first time you crossdressed? Bra and Panties
2. How long did you first wear it? Half a day
3. Where is the best place you've gone while dressed up? Grocery shopping
4. Did you usually cum after crossdressing? Yes
5. What colour is the clothing you like best? Black
6. Did you use any sextoys? Which ones? Yes, butt plug, dildo and nipper clamps
7. Have you bought more clothes to crossdress in since then? Yes
8. What do you fantasize about crossdressing in most? Bra, panties, with stockings and garter
9. Bra or thong? Thong
10. Latex or fishnets? Fishnets
11. Skirt or shorts? Skirt
12. Pink or blue? Pink
13. Heels or flats? Flats
14. Blonde or brunette? Brunette
15. Makeup or Wig? Makeup
16. Fake tits or natural? Fake

[sissy_nikki]

Here's 16 questions about crossdressing! Use as much detail as you like, the more the better

1. What did you wear the first time you crossdressed?
a body suit...i lost a bet with my sister and that was what she made me do
2. How long did you first wear it?
it was for about an hour
3. Where is the best place you've gone while dressed up?
i have only dressed up in private..my house or someone else's house, so far
4. Did you usually cum after crossdressing?
some times, i try not to, dressing puts me in this "sissy high" and i never want to leave that, once i get into it, and cumming always takes me out.
5. What colour is the clothing you like best?
i tend to lean more toward black or red
6. Did you use any sextoys? Which ones?
yes, my former online Mistress made me buy a dildo. i had to practice with it and send her pics and video of my progress.
7. Have you bought more clothes to crossdress in since then?
unfortunately, i am married, so i can't buy a lot, i try to get what i can, and keep it hidden away...need lots more though
8. What do you fantasize about crossdressing in most?
i am a total submissive, so my biggest fantasy has always been about being forced fem and totally used by a couple
9. Bra or thong?
took a while, but after i got used to a thong, i love them
10. Latex or fishnets?
never worn either yet, fishents sound exciting though, will need to try both to know for sure
11. Skirt or shorts?
i just love, short, short skirts ;-)
12. Pink or blue?
in sissy form, i would tend to gravitate more toward pink...i even have a pink wig
13. Heels or flats?
still getting used to wearing and walking in heels, i want/need more practice
14. Blonde or brunette?
i think i look a little better as a dirty blonde, somewhere in between a blond and brunette
15. Makeup or Wig?
have only had makeup on a couple times, once turned out nice (done by another woman) once was terrible (done by another crossdresser) my goal is always to be able to look as much like a real girl as possible, so i really want/need both
16. Fake tits or natural?[/QUOTE]
i would need fake, have tried them once, felt nice ;-)

[Thursday]

1. What did you wear the first time you crossdressed? - Panties, just panties. After that it was panties and a bra. After that it was panties, bha and a purple dress.
2. How long did you first wear it? - I just just for ~1h, but nowadays I wear it for a whole day, most of the times only panties, but sometimes also for a whole day
3. Where is the best place you've gone while dressed up? - my home, I feel safe here But I also did go shopping in panties and bra
4. Did you usually cum after crossdressing? - yes
5. What colour is the clothing you like best? - my purple dress and my yellow skirt
6. Did you use any sextoys? Which ones? - Butt plug and dildo while beeing cross dressed and running around. I keep the big dildo inside me whit a female one pice swim suite.
7. Have you bought more clothes to crossdress in since then? - yes
8. What do you fantasize about crossdressing in most? - beeing a girl and having to serve men
9. Bra or thong? - both? If I have to choose I'd go for thong, it's easier concealable in public
10. Latex or fishnets? - fishnets
11. Skirt or shorts? - skirt
12. Pink or blue? - pink
13. Heels or flats? - flats
14. Blonde or brunette? blonde
15. Makeup or Wig? - wig, easier to remove
16. Fake tits or natural? - I'd love to have natural, I sometimes stuff my bra however since I lak the natural ones.

[SydSwallows]

1. What did you wear the first time you crossdressed? PANTIES

2. How long did you first wear it? A FEW HOURS

3. Where is the best place you've gone while dressed up? ADULT BOOKSTORE

4. Did you usually cum after crossdressing?YES

5. What colour is the clothing you like best?BLUE

6. Did you use any sextoys? Which ones?DILDO

7. Have you bought more clothes to crossdress in since then?YES

8. What do you fantasize about crossdressing in most?BRA/PANTIES

9. Bra or thong? THONG
10. Latex or fishnets? FISHNETS
11. Skirt or shorts?SKIRT
12. Pink or blue?BLUE
13. Heels or flats?FLAT
14. Blonde or brunette?BLONDE
15. Makeup or Wig?MAKEUP
16. Fake tits or natural?NATURAL

[MahonD]

1. What did you wear the first time you crossdressed?
A yellow dress with flowers. My sister made me wear it when I was in elementary school.

2. How long did you first wear it?
About an hour.

3. Where is the best place you've gone while dressed up?
Club in SC

4. Did you usually cum after crossdressing?
No, but sometimes men talk to me just right~

5. What colour is the clothing you like best?
Red or black outerwear, white or pink underwear~

6. Did you use any sextoys? Which ones?
No, I don't use sextoys.

7. Have you bought more clothes to crossdress in since then?
Yes~ My wardrobe is mostly female clothes now.

8. What do you fantasize about crossdressing in most?
Making out with a man and him holding me very close <3

9. Bra or thong?
Bra

10. Latex or fishnets?
Fishnets

11. Skirt or shorts?
Definitely skirts <3

12. Pink or blue?
Pink <3

13. Heels or flats?
Heels

14. Blonde or brunette?
Blonde

15. Makeup or Wig?
Both <3

16. Fake tits or natural?
Natural with a push up bra.

[tashaslut]

1. What did you wear the first time you crossdressed?
Black thong of my mom, "borrowed" it from her wardrobe.

2. How long did you first wear it?
Only for about half an hour. But I didn't put it back immediately. It was only about 2 days later I managed to put it back.

3. Where is the best place you've gone while dressed up?
I think going shopping in a mall is the best so far.

4. Did you usually cum after crossdressing?
Yes, most of the times.

5. What colour is the clothing you like best?
Speaking about lingerie, it is definitely black. Otherwise, I like to wear various colours, but not too saturated ones.

6. Did you use any sextoys? Which ones?
I almost always use toys, mostly plugs and some dildos. Maybe expanding in the future.

7. Have you bought more clothes to crossdress in since then?
Yes, I have bought many clothes, especially lingerie. If you'd like to know more specific, send me a PM.

8. What do you fantasize about crossdressing in most?
About being a submissive slut, who's only purpose is to be fucked as liked.

9. Bra or thong?
Bra – more feminine

10. Latex or fishnets?
Fishnets – not into latex

11. Skirt or shorts?
Shorts – stronger emphasis on the butt

12. Pink or blue?
Blue – pink is mostly too satursated

13. Heels or flats?
Heels – definitely sexier

14. Blonde or brunette?
Brunette – not too big of a deal

15. Makeup or Wig?
Makeup – if you grow your own hair, no need for a wig

16. Fake tits or natural?
Natural – is definitely better, in certain cases fake can be superior

[janesg]

1. What did you wear the first time you crossdressed?
Tartan mini skirt and vest top

2. How long did you first wear it?
A few hours

3. Where is the best place you've gone while dressed up?
A few parties

4. Did you usually cum after crossdressing?
No

5. What colour is the clothing you like best?
No particular favourite

6. Did you use any sextoys? Which ones?
Not really, some nipple clamps on occassion. Tried other things, not really for me.

7. Have you bought more clothes to crossdress in since then?
Way too many.

8. What do you fantasize about crossdressing in most?
Sometimes nothing, sometimes submissive fantasies, sometimes being someone's regular girlfriend, sometimes age play.

9. Bra or thong?
Bra

10. Latex or fishnets?
Neither

11. Skirt or shorts?
Skirts

12. Pink or blue?
Either if it's the right outfit

13. Heels or flats?
Depends on the outfit, flats if it's age play related.

14. Blonde or brunette?
Brunette

15. Makeup or Wig?
Have long real hair, sometimes make-up.

16. Fake tits or natural?
Natural

[Midorikawa]

1. What did you wear the first time you crossdressed?
I think it was a pair of panties and a spaghetti strop top that belonged to my sister, been so many years since I barely remember

2. How long did you first wear it?
Not for long, was afraid my parents or sister would find out

3. Where is the best place you've gone while dressed up?
Haven't really gone anywhere, always chicken out at the last moment. Only really gone around the block late at night

4. Did you usually cum after crossdressing?
Not really, I often cross dress as my home clothes

5. What colour is the clothing you like best?
Denim blue, have a fantastic skirt made from denim

6. Did you use any sextoys? Which ones?
Yes, have a great collection, see my sig for the list, and it's often expanding

7. Have you bought more clothes to crossdress in since then?
Yes, I have pretty good amount by now. Love wearing it as my weekend/after work clothes

8. What do you fantasize about crossdressing in most?
A maid outfit, just being someone's maid, including bondage toys

9. Bra or thong?
Bra – thongs just doesn't fit me right

10. Latex or fishnets?
Latex, or latex lookalike, love the wetlook look

11. Skirt or shorts?
Skirts, love doing the twirl and seeing it fan out

12. Pink or blue?
Blue, a good navy blue for everyday wear, but babypink for play time

13. Heels or flats?
Heels, even if I look like wobbly in them

14. Blonde or brunette?
Brunette, from these choices, else redhead

15. Makeup or Wig?
Makeup, love doing my nails

16. Fake tits or natural?
Natural, wish I could have them myself

[sissybill]

1. What did you wear the first time you crossdressed?= my x-gfs hot shorts n bikini top
2. How long did you first wear it?= all night while she was at work
3. Where is the best place you've gone while dressed up?=too a park
4. Did you usually cum after crossdressing?=sometimes
5. What colour is the clothing you like best?=purple n black lace
6. Did you use any sextoys? Which ones?=no
7. Have you bought more clothes to crossdress in since then?=omg yes lots more
8. What do you fantasize about crossdressing in most?=a womens buissness suite
9. Bra or thong=bra
10. Latex or fishnets?=fishnets
11. Skirt or shorts?=short skirt
12. Pink or blue?=pink 1st then blue
13. Heels or flats?= heels
14. Blonde or brunette?=brunette
15. Makeup or Wig?=wig
16. Fake tits or natural?=big 42hhh fake tits

[Slave_Boy00]

1. What did you wear the first time you crossdressed?
Just some panties from my mom

2. How long did you first wear it?
I got too excited and just wore it for a couple minutes

3. Where is the best place you've gone while dressed up?
So far I didn't go out dressed up

4. Did you usually cum after crossdressing?
Yeah as long as I wasn't in chastity

5. What colour is the clothing you like best?
Pink and black

6. Did you use any sextoys? Which ones?
Dildos and buttplugs

7. Have you bought more clothes to crossdress in since then?
Yes lots of

8. What do you fantasize about crossdressing in most?
Serving someone in every way possible

9. Bra or thong?
Thong <3

10. Latex or fishnets?
Fishnets

11. Skirt or shorts?
Skirt

12. Pink or blue?
Pink

13. Heels or flats?
Heels

14. Blonde or brunette?
Brunette

15. Makeup or Wig?
Wig

16. Fake tits or natural?
Fake

[zephyrnem]

Hi Everyone!

Here's 16 questions about crossdressing! Use as much detail as you like, the more the better

1. What did you wear the first time you crossdressed?

Full outfit for a show

2. How long did you first wear it?

3 hours or so

3. Where is the best place you've gone while dressed up?

Hard to say. Probably the intimate Shakespeare show I did in a dress and panties. During the fight scene, the audience saw...a lot of me.

4. Did you usually cum after crossdressing?

Not usually

5. What colour is the clothing you like best?

Pink, colorful

6. Did you use any sextoys? Which ones?

No

7. Have you bought more clothes to crossdress in since then?

Yes. One piece swimsuit. Fishnet bodysuit. Short skirt. Blouse.

8. What do you fantasize about crossdressing in most?

Swimsuit, fishnets

9. Bra or thong?

Thong

10. Latex or fishnets?

Fishnet

11. Skirt or shorts?

Skirt

12. Pink or blue?

Pink

13. Heels or flats?

Barefoot

14. Blonde or brunette?

Blonde

15. Makeup or Wig?

Wig

16. Fake tits or natural?

Natural

[Asmodeus-]

1. What did you wear the first time you crossdressed?

I was doing the washing when i was around 14 and found a pair of my mums panties and it all started from there.

2. How long did you first wear it?

Probably around an hour

3. Where is the best place you've gone while dressed up?

Walking home from work

4. Did you usually cum after crossdressing?

if i do cum the i will cum during, never after

5. What colour is the clothing you like best?

Pink and purple

6. Did you use any sextoys? Which ones?

I use anything and everything, cage, plug and dildo are my go to one though

7. Have you bought more clothes to crossdress in since then?

i have spent more money on girl clots then i have boy cloths

8. What do you fantasize about crossdressing in most?

Anything girly, nothing in particular

9. Bra or thong?

Thong for sure

10. Latex or fishnets?

Latex

11. Skirt or shorts?

defo a skirt

12. Pink or blue?

Pink all the way

13. Heels or flats?

Heels, is there anything else?

14. Blonde or brunette?

Brunette
15. Makeup or Wig?

Make-up, i have long hair

16. Fake tits or natural?

real would be my dream

[Mael]

1. What did you wear the first time you crossdressed?
-female jeans (they just had a way better fit)
2. How long did you first wear it?
-whole day/ daily, jeans ... well kinda underwhelming looking at the development ...
3. Where is the best place you've gone while dressed up?
-to a disco (90s/ metalparty) or a bdsm-club ... can't decide ... first was a thrill because it was sort of more "public", second was better, but mostly due to playing than crossdressing
4. Did you usually cum after crossdressing?
-no, it isn't a very sexual thing for me, more a choice/ statement not to make differences
5. What colour is the clothing you like best?
-black, (i know boring ... but party- boots are party- boots)
6. Did you use any sextoys? Which ones?
-while crossdressing? chastity cage & plugs ... in general? yes, haven't had an e-stim session, yet ... despite that ...
7. Have you bought more clothes to crossdress in since then?
-i think i have a few male items left
8. What do you fantasize about crossdressing in most?
-regarding answer 4, there's not much fantasizing just due to justz crossdressing (as i'm largely open with it, its not fantasizing, more remembering)
9. Bra or thong?
yes (the combination is key), for everyday: thong
10. Latex or fishnets?
depending the occasion... normal party => fishnet, kink/bdsm => latex
11. Skirt or shorts?
skirt
12. Pink or blue?
neither, red/ black
13. Heels or flats?
heels
14. Blonde or brunette?
brunette
15. Makeup or Wig?
makeup
16. Fake tits or natural?
for me to crossdress? well fake ... for my partner? natural, but i don't mind fakes