16 Questions: CrossDressing
 

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?
2. How long did you first wear it?
3. Where is the best place you've gone while dressed up?
4. Did you usually cum after crossdressing?
5. What colour is the clothing you like best?
6. Did you use any sextoys? Which ones?
7. Have you bought more clothes to crossdress in since then?
8. What do you fantasize about crossdressing in most?
9. Bra or thong?
10. Latex or fishnets?
11. Skirt or shorts?
12. Pink or blue?
13. Heels or flats?
14. Blonde or brunette?
15. Makeup or Wig?
16. Fake tits or natural?

1. What did you wear the first time you crossdressed?
My girlfriend's sexy Santa costume
2. How long did you first wear it?
About a whole day during a party she threw
3. Where is the best place you've gone while dressed up?
Walked around the mall
4. Did you usually cum after crossdressing?
When I'm cross dressed I'm usually being forced to by my girlfriend so she doesn't always let me cum
5. What colour is the clothing you like best?
Red, white, or pink
6. Did you use any sextoys? Which ones?
A couple squirting dildos
7. Have you bought more clothes to crossdress in since then?
No I always use someone else's
8. What do you fantasize about crossdressing in most?
Mini skirts, really short crop tops and high heels while in full makeup
9. Bra or thong?
Bra
10. Latex or fishnets?
Honestly like both but if I had to choose I'd say fishnets
11. Skirt or shorts?
Skirts
12. Pink or blue?
Pink
13. Heels or flats?
Heels
14. Blonde or brunette?
Blonde
15. Makeup or Wig?
Makeup
16. Fake tits or natural?
Natural

1. What did you wear the first time you crossdressed?
Probably a girls jacket

2. How long did you first wear it?
I think it was in school, so probably only for a few seconds

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

4. Did you usually cum after crossdressing?
Yep!

5. What colour is the clothing you like best?
Black and white

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

7. Have you bought more clothes to crossdress in since then?
I have bought a lot in many years, but I always throw them away after some time

8. What do you fantasize about crossdressing in most?
Full atirre!

9. Bra or thong?
Bra AND thong

10. Latex or fishnets?
Fishnets

11. Skirt or shorts?
Skirt ofcourse!

12. Pink or blue?
Pink

13. Heels or flats?
Heels! That’s half the fun of crossdressing!

14. Blonde or brunette?
Blonde

15. Makeup or Wig?
Wig, but makeup is fun too

16. Fake tits or natural?
If I could have natural, then natural ofcourse

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

Thong

2. How long did you first wear it?

Maybe 1-2h

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

Well only my home. Took out the trash fully dressed once

4. Did you usually cum after crossdressing?

I used to, now I am a bit on self denial/chastity so I dress up for fun and clean up duty

5. What colour is the clothing you like best?

Pink and black

6. Did you use any sextoys? Which ones?

Yes analplug and a vibrator
7. Have you bought more clothes to crossdress in since then?

Yes I have.
8. What do you fantasize about crossdressing in most?

Being pegged by a mistress while caged until i cum

9. Bra or thong?

Thong


10. Latex or fishnets?

Fishnet right now. Never had latex. But buying it soon

11. Skirt or shorts?

Skirts anytime

12. Pink or blue?

Pink


13. Heels or flats?

Heels

14. Blonde or brunette?

Brünette

15. Makeup or Wig?

Wig

16. Fake tits or natural?

Natural

1. What did you wear the first time you crossdressed?
Panties
2. How long did you first wear it?
Probably about 30 mins
3. Where is the best place you've gone while dressed up?
To the mall
4. Did you usually cum after crossdressing?
About half the time I do
5. What colour is the clothing you like best?
Red/black
6. Did you use any sextoys? Which ones?
Sometimes. Buttplug, dildo, bondage gear
7. Have you bought more clothes to crossdress in since then?
Oh yes
8. What do you fantasize about crossdressing in most?
Most of the time its costumes like a school girl or a maid
9. Bra or thong?
bra
10. Latex or fishnets?
fishnet
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
16. Fake tits or natural?
natural

1. What did you wear the first time you crossdressed? wife's black dress
2. How long did you first wear it? 5 minutes
3. Where is the best place you've gone while dressed up? home
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? no
7. Have you bought more clothes to crossdress in since then? no
8. What do you fantasize about crossdressing in most? hidden secret
9. Bra or thong? thong
10. Latex or fishnets? fishnet
11. Skirt or shorts? skirt
12. Pink or blue? blue
13. Heels or flats? flats
14. Blonde or brunette? brunette
15. Makeup or Wig? wig
16. Fake tits or natural? natural

1. What did you wear the first time you crossdressed?
My sisters panties
2. How long did you first wear it?
I wore it to bed
3. Where is the best place you've gone while dressed up?
I have been to a couple different stores including getting my makeup dones at Sephora
4. Did you usually cum after crossdressing?
Sometimes, but not always
5. What colour is the clothing you like best?
I love blues :)
6. Did you use any sextoys? Which ones?
I have a dildo and a few plugs (my favorite is my Core butt plug as it's really comfortable to wear long term
7. Have you bought more clothes to crossdress in since then?
I'm always buying more clothes, I may even be at the point of having more female clothes now...
8. What do you fantasize about crossdressing in most?
Dresses, I love the way dresses look and feel. They make me feel sexy more than girly tops and skirts.
9. Bra or thong?
Bra, I'm not a huge fan of thongs, I still wear them every now and then but not often
10. Latex or fishnets?
Latex as I can't ahave my legs to look sexy in fishnets :(
11. Skirt or shorts?
Skirts
12. Pink or blue?
Blue, punk when I really want to feel girly but I still prefer blue :p
13. Heels or flats?
depends on how long I'm wearing them :p but I own more heels so there's that lol
14. Blonde or brunette?
Brunette
15. Makeup or Wig?
Both, but if I had to choose I would go with as I cut my hair short for summer
16. Fake tits or natural?
Natural, benefit of being a bit chubby is that I can fill a B cup

1. What did you wear the first time you crossdressed? cannot remember
2. How long did you first wear it? cannot remember
3. Where is the best place you've gone while dressed up? pink punters in milton kenyes
4. Did you usually cum after crossdressing? no
5. What colour is the clothing you like best? anything bright and colourful
6. Did you use any sextoys? Which ones? not really got a couple but don't use them much
7. Have you bought more clothes to crossdress in since then? yes
8. What do you fantasize about crossdressing in most? passing and being totally treated as a girl in a social setting.
9. Bra or thong? Bra
10. Latex or fishnets? fishnets
11. Skirt or shorts? skirt
12. Pink or blue? blue
13. Heels or flats? Heels
14. Blonde or brunette? brunette
15. Makeup or Wig? wig
16. Fake tits or natural? natural

Hi all. First time I post so I think this would be nice so you know a little about me. Kisses!

1. What did you wear the first time you cross dressed?
black high heeled sandals of a neighbor
2. How long did you first wear it?
think about an hour or so. Took them on for a self bondage session (self hogtied)
3. Where is the best place you've gone while dressed up?
a bench in the wood in full feminine attire, with sone toys in the purse
4. Did you usually cum after crossdressing?
it depends, not always. And sometimes I don’t even touch it. Only.....anal play
5. What colour is the clothing you like best?
blue (black for lingerie)
6. Did you use any sextoys? Which ones?
I use dildoes and plugs, chocolates and bananas.....
7. Have you bought more clothes to crossdress in since then?yes. Some also borrowed or..... stolen!
8. What do you fantasize about crossdressing in most? I am much into classy dresses, pencil skirts, LBDs, and high heels of course
9. Bra or thong? both!
10. Latex or fishnets? albeit I prefer sheer black stockings, if I have to choose.... fishnets then
11. Skirt or shorts?skirts
12. Pink or blue? blue of course
13. Heels or flats? heels are a big turn on. Recently considering flat ballerinas and miniskirt to be an interesting combination, for a walk in a park, maybe
14. Blonde or brunette? brunette!
15. Makeup or Wig? make-up. No need to use wig, as I have hair long enough to look girly if I comb them properly
16. Fake tits or natural? fake or stuffed bra

1. What did you wear the first time you crossdressed?
School girls uniform , was at a school in summer and it was really hot , we were not allowed to wear shorts, but girls could wear skirts . School rules were white shirt , school jumper , black trousers , grey socks , black shoes or blouse , scho jumper , black skirt ( to knee level ) white socks , black flat shoes ! So a group of us borrowed our sisters or friends sisters uniform and word that !
2. How long did you first wear it?
1 week
3. Where is the best place you've gone while dressed up?
Shopping
4. Did you usually cum after crossdressing?
Sometimes
5. What colour is the clothing you like best?
Red
6. Did you use any sextoys? Which ones?
No
7. Have you bought more clothes to crossdress in since then?
Yes
8. What do you fantasize about crossdressing in most?
Nurses outfit
9. Bra or thong?
Tho g
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?
Make up
16. Fake tits or natural?
Natural

1. What did you wear the first time you crossdressed? Panties I think
2. How long did you first wear it? idk not for long
3. Where is the best place you've gone while dressed up? with panties/bra underneath normal clothes just around in my town
4. Did you usually cum after crossdressing? yes
5. What colour is the clothing you like best? white
6. Did you use any sextoys? Which ones? no
7. Have you bought more clothes to crossdress in since then? using my sisters
8. What do you fantasize about crossdressing in most? short skirts, bodystocking
9. Bra or thong? umm thong
10. Latex or fishnets? haven't really tried them
11. Skirt or shorts? Love skirts more but if I need to wear it in public then shorts
12. Pink or blue? Pink
13. Heels or flats? Flats
14. Blonde or brunette? brunette
15. Makeup or Wig? idk
16. Fake tits or natural? natural

1. What did you wear the first time you crossdressed?
I wore a dress that was a light blue color at night while my family was asleep.
2. How long did you first wear it?
For about 30 minutes before taking it off and hiding it.
3. Where is the best place you've gone while dressed up?
I have only left my house once while dressed up and it was because of another dare on here (went out at night)
4. Did you usually cum after crossdressing?
Not usually, because it breakes me out of the mindset and I can't really bring myself to stay dressed.
5. What colour is the clothing you like best?
I like pastel colors in blue and pink.
6. Did you use any sextoys? Which ones?
I have a vibrating dildo and a plug in the mail.
7. Have you bought more clothes to crossdress in since then?
Yes, a few pair of bedazzled jeans, some blouses, a skirt, and a jacket.
8. What do you fantasize about crossdressing in most?
I just like to pretend.
9. Bra or thong?
bra
10. Latex or fishnets?
fishnets
11. Skirt or shorts?
skirts are the best
12. Pink or blue?
blue
13. Heels or flats?
Flats heels are too uncomfortable.
14. Blonde or brunette?
Blond
15. Makeup or Wig?
Makeup
16. Fake tits or natural?
Natural.

1. What did you wear the first time you crossdressed?
Tights
2. How long did you first wear it?
10 or 15 minutes
3. Where is the best place you've gone while dressed up?I
Never gone out in public but hidden public at work is probably the best
4. Did you usually cum after crossdressing?I
Usually? Probably 50 50
5. What colour is the clothing you like best?
Black
6. Did you use any sextoys? Which ones?I
No
7. Have you bought more clothes to crossdress in since then?I
I buy them from time to time
8. What do you fantasize about crossdressing in most?I
Probably leotards that have just been used.
9. Bra or thong?
Thong. Dont care for bras
10. Latex or fishnets?I
Fishnets
11. Skirt or shorts?I
Skirt ideally tartan as short as possible
12. Pink or blue?I
Blue
13. Heels or flats?I
Not really interested in shoes
14. Blonde or brunette?I
Nor wigs
15. Makeup or Wig?I
Nor makeup
16. Fake tits or natural?I
See answer above on bra

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?
one of momd bras
2. How long did you first wear it?
no more than a few minutes, as i wasnt alone but quickly wore it again
3. Where is the best place you've gone while dressed up?
Went for a walk down the riverside in town wearing a prom dress one evening. Ones an amazing feeling but kind of scary to
4. Did you usually cum after crossdressing?
no, I did sometimes don't others
5. What colour is the clothing you like best?
anything that looks realistically girly nor a fan of over the tip sissy clothes
6. Did you use any sextoys? Which ones?
not at the moment t but in the past used a glass plug and clover nipple clamps
7. Have you bought more clothes to crossdress in since then?
yes I regularly buy new clothes and usually in person
8. What do you fantasize about crossdressing in most?
a wedding dress , with a tight orset locked into me
9. Bra or thong?
bra, preferably satin with padded cups
10. Latex or fishnets?
fishnets
11. Skirt or shorts?
skirt they seem more feminine
12. Pink or blue?
either, dark blue is sexy in saying or silk
13. Heels or flats?
flats, they are more practical
14. Blonde or brunette?
brunette
15. Makeup or Wig?
wig
16. Fake tits or natural?
fake, or padded bra I'm to skinny to have natural tits

1. What did you wear the first time you crossdressed?
My crush's panties.

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

3. Where is the best place you've gone while dressed up?
An amusement park!

4. Did you usually cum after crossdressing?
Umm, when I'm not in chastity yeah.

5. What colour is the clothing you like best?
Black and white, but sometimes red and black.

6. Did you use any sextoys? Which ones?
Butt plug and hitachi magic wand.

7. Have you bought more clothes to crossdress in since then?
Yeppp, I'm in female clothes almost 24/7 now.

8. What do you fantasize about crossdressing in most?
Umm, it's not a fantasy anymore, really. I just wear whatever girl clothes I want.

9. Bra or thong?
Why not both? :P

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?
Natural.