16 Questions: CrossDressing

[DanHenceworth]

1. What did you wear the first time you crossdressed?
a thong, a bra and a flowery dress

2. How long did you first wear it?
20 minutesish

3. Where is the best place you've gone while dressed up?
wore thong to shops and stuff but thats it

4. Did you usually cum after crossdressing?
yes
5. What colour is the clothing you like best?
pink
6. Did you use any sextoys? Which ones?
yes
chastity cage
wand
dildo
anal beads
butt plugs

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

8. What do you fantasize about crossdressing in most?
being a full time sissy maid

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?
blonde

15. Makeup or Wig?
wig

16. Fake tits or natural?
fake big bimbo tits

[CagedHiruzen]

1. What did you wear the first time you crossdressed?
I believe it was a leotard and a pair of nylons
2. How long did you first wear it?
For the full day.
3. Where is the best place you've gone while dressed up?
The store or out to eat
4. Did you usually cum after crossdressing?
No, I don't.
5. What colour is the clothing you like best?
Pink.
6. Did you use any sextoys? Which ones?
I like butt plugs and dildos.
7. Have you bought more clothes to crossdress in since then?
Yup panties bras and various other clothes.
8. What do you fantasize about crossdressing in most?
Corsets and thongs.
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?
Blonde.
15. Makeup or Wig?
Both.
16. Fake tits or natural?
Either but natural.

[kellianne1]

1. What did you wear the first time you crossdressed?
A tan mini dress, $ inch wedge heels, wig,

2. How long did you first wear it?
4 hours

3. Where is the best place you've gone while dressed up?
At a local bar for Halloween.

4. Did you usually cum after crossdressing?
Not normally

5. What colour is the clothing you like best?
Mostly neutral colors

6. Did you use any sextoys? Which ones?
Butt plugs, Vibrators, Clamps, assorted cock substitutes

7. Have you bought more clothes to crossdress in since then?
Oh! yes i love new stuff

8. What do you fantasize about crossdressing in most?
Micro skirts, See through clothes, Heels

9. Bra or thong?
I am not allowed either

10. Latex or fishnets?
Fishnets

11. Skirt or shorts?
Skirts. I am not allowed to wear trousers or pants

12. Pink or blue?
Mostly greens or pink

13. Heels or flats?
Heels always, even my tennis shoes have a 2 inch heel.

14. Blonde or brunette?
Redhead

15. Makeup or Wig?
Both

16. Fake tits or natural?
I wish they were natural.

The woman I went dancing with that night was amazed how comfortable I was in women's clothes. After dancing we went to her house, and started making out, She held my head into her pussy while I eat her. This lead of course to stripping her naked. She then begged me to bend over the couch, she paddled me hard and then rubbed some tiger balm on my butt. I got my first pegging and then It wasn't long before the switch in me took over. I flipped her over onto my fishnet covered lap and soundly spanked her bottom.
I then returned the favor and gave her a sound fucking while pulling her nipples hard.

[BeauSasha]

1. What did you wear the first time you crossdressed? I'm not even sure... Probably panties or a shirt that I stole from a friend. I was middle-school aged when I started.
2. How long did you first wear it? Probably just a few minutes.
3. Where is the best place you've gone while dressed up? The first time fully crossdressed in public I was maybe 19 or 20 with my then-girlfriend. We went to Arby's.
4. Did you usually cum after crossdressing? Yes
5. What colour is the clothing you like best? If I'm trying to be discreet and wear it under my normal clothes I go with white, otherwise I love all the different colors and designs that girls get that guys don't.
6. Did you use any sextoys? Which ones? Yes. Buttplugs, vibrators, gag, blindfold
7. Have you bought more clothes to crossdress in since then? Oh yes
8. What do you fantasize about crossdressing in most? Something skimpy that I actually fit in after I lose a lot of weight...
9. Bra or thong? Depends on when and where
10. Latex or fishnets? Fishnets
11. Skirt or shorts? Again, depends when and where
12. Pink or blue? Pink
13. Heels or flats? Depends if I'm trying to not catch attention in public
14. Blonde or brunette? Blonde
15. Makeup or Wig? Makeup
16. Fake tits or natural? Natural

[Jfreeman1999]

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?
Bra and panties

2. How long did you first wear it?
I slept all night in them

3. Where is the best place you've gone while dressed up?
Went to a costume party dressed as a mermaid

4. Did you usually cum after crossdressing?
Sometimes

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

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?
Frilly pink dresses

9. Bra or thong?
Bra feels more feminine. Would like to try a thong though

10. Latex or fishnets?
Tricky, Only tried either once but I'll have to go for fishnets. More naturally feminine

11. Skirt or shorts?
Skirts. I like to be as feminine as possible

12. Pink or blue?
Pink, nice and girly

13. Heels or flats?
Heels, need the full girly experience

14. Blonde or brunette?
Brunette goes better with my face

15. Makeup or Wig?
Wig. Make up looks weird without a wig. I need either both or just the wig

16. Fake tits or natural?[/QUOTE]
Fake. I like to look more feminine

[BWeird]

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? Tights and a unitard. I was 10 and it's what I could find around the house.

2. How long did you first wear it? I don't remember the first time exactly but it was most likely for the whole day. I always wear panties, bras, tights, tank tops under my daily clothes.

3. Where is the best place you've gone while dressed up? I went out to a restaurant for dinner completely dressed up once.

4. Did you usually cum after crossdressing? That's the main reason I enjoy crossdressing. It turns me on. I almost always cum while or after dressing up.

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

6. Did you use any sextoys? Which ones? While dressed I only would use a buttplug and sometimes a chastity cage. However I can fill a suitcase with all the others I have.

7. Have you bought more clothes to crossdress in since then? Yes. I have bought many items in the 30 years I've been dressing up.

8. What do you fantasize about crossdressing in most? Corsets and mini skirts.

9. Bra or thong? Always have a thong on.

10. Latex or fishnets? Latex. It's nice and tight.

11. Skirt or shorts? Skirts. They're more feminine.

12. Pink or blue? Pink. It makes me feel more feminine.

13. Heels or flats? Heels. They're sexier.

14. Blonde or brunette? Brunette. It fits me better.

15. Makeup or Wig? Makeup if I had to choose just one.

16. Fake tits or natural? Well I need fake but natural would be better.

[LinoySlave]

1. What did you wear the first time you crossdressed?
Yoga pants, panties, bra, cut-top
2. How long did you first wear it?
About 2 hours
3. Where is the best place you've gone while dressed up?
No where actually
4. Did you usually cum after crossdressing?
No
5. What colour is the clothing you like best?
Pink-white
6. Did you use any sextoys? Which ones?
just a buttplug
7. Have you bought more clothes to crossdress in since then?
Just a couple of yoga pants
8. What do you fantasize about crossdressing in most?
To be fully crossdressed and hang outside with a bf or maybe a party
9. Bra or thong?
Bra
10. Latex or fishnets?
Fishnets
11. Skirt or shorts?
hmm, I'll go for a shorts but a skirt is also very good
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?
Natural
__________________

[Consensus]

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

Sad to say, just a lacy thong. It was sent to mimic me having a secret admirer when I got my first girlfriend (it was at University), my floor mates were hoping I'd end the relationship and then laugh. Instead, I wore the thong a few times before finally purging a couple of weeks later.

2. How long did you first wear it?

An hour or two maybe? I was so scared of being found out!

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

With my second girlfriend I dressed as a schoolgirl for a club on her birthday. Only one of two times dressed in public, and the first time. It was lovely. I wish I could do it again.

4. Did you usually cum after crossdressing?

This one is harder to answer. I did a lot but the best times, like the one above, were times I didn't.

5. What colour is the clothing you like best?

I wish I suited yellow.

6. Did you use any sextoys? Which ones?

No.

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

Yes. I bought a pack of knickers before I went out with my second girlfriend, added a dress and some stockings. Then, after she and I split up, I got a chemise, a top and a skirt or two. Since then I have bought more, purged and then bought more. There was a pause when my third girlfriend moved in but after we we'd I started again, when the marriage went sexless.

8. What do you fantasize about crossdressing in most?

I don't so much, mainly it's just the feeling of being dressed. In what is immaterial, I look like a complete Berk either way so I fantasise that someone else actually likes to see me dressed, don't worry, it is pure fantasy.

9. Bra or thong?

Bra.

10. Latex or fishnets?

Fishnets, surprisingly comfy.

11. Skirt or shorts?

Skirt.

12. Pink or blue?

Blue. Powder blue.

13. Heels or flats?

Heels, I know I am a cliché!

14. Blonde or brunette?

Brunette. I am naturally.

15. Makeup or Wig?

Wig.

16. Fake tits or natural?

Both, to be fair. I like adding fake ones.

Thank you for the questions, I hope my answers were worth reading.

[darkness991]

1. What did you wear the first time you crossdressed?
the very first time i crossdressed i was still in my first school in the eight year and i went dressed a britney spears to celibrate carnival but that wasnt for kink that started with stealing a thong from my mom and later by taking a dress from the attic

2. How long did you first wear it?
a couple of hours not sure it was to long agow

3. Where is the best place you've gone while dressed up?
to a friend and her boyfriend i spend the weekend there to get fucked by them

4. Did you usually cum after crossdressing?
mostly while still dressed cause it makes me horny

5. What colour is the clothing you like best?
iv got no preference

6. Did you use any sextoys? Which ones?
yes lots iv got a list in my sig and used all

7. Have you bought more clothes to crossdress in since then?
yes i have bought stolen and gotten lots of clothes

8. What do you fantasize about crossdressing in most?
not really a fantasy anymore since iv got so much already but i would still like a good fitting maids outfit

9. Bra or thong?
thong they feel so good when i wear them

10. Latex or fishnets?
i like latex more but i dont have any of it yet

11. Skirt or shorts?
skirt pull it up and fuck me

12. Pink or blue?
pink since only 2 options plus pretty stupid question pink is female blue is male

13. Heels or flats?
heels

14. Blonde or brunette?
i am naturally blond

15. Makeup or Wig?
makeup i dont need a wig with long blond curly hair

16. Fake tits or natural?
i would like fake tits for myself and natural ones for a partner

[curiy]

1. What did you wear the first time you crossdressed?
First tryed on my mum bra and big panties but soon moved to my aunties bra and panties and bikinis he was a better fit and a lot sexier stuff.
2. How long did you first wear it?
About half a hour.
3. Where is the best place you've gone while dressed up?
I once got drunk wanked in to a big sex shop and tryed on all the slutty clothes there and shower them off to the shop owner and who ever else walked in
4. Did you usually cum after crossdressing?
Sure do
5. What colour is the clothing you like best?
Pink is so pretty and girly
6. Did you use any sextoys? Which ones?
Dildos and buttplug
7. Have you bought more clothes to crossdress in since then?
Yer I have got a lot more but have none now
8. What do you fantasize about crossdressing in most?
In some on I knows cloths so they can find me punish me and humiliate me
9. Bra or thong?
Both
10. Latex or fishnets?
Fishnets
11. Skirt or shorts?
Both as long as they are so short to hind anything
12. Pink or blue?
Pink
13. Heels or flats?
Heels
14. Blonde or brunette?
Blonde
15. Makeup or Wig?
Both
16. Fake tits or natural?
Wish I could be natural

[rhl]

1. What did you wear the first time you crossdressed?
- - girls bluejeans
2. How long did you first wear it?
- - all day
3. Where is the best place you've gone while dressed up?
- - really not sure, but it is fun to go shopping
4. Did you usually cum after crossdressing?
- - no
5. What colour is the clothing you like best?
- - blues or browns always have been my favorites
6. Did you use any sextoys? Which ones?
- - not sure what this has to do with the subject but several mouth gags, butt plugs, and a few bondage items
7. Have you bought more clothes to crossdress in since then?
- - of course, panties, stockings, leggings, skirts, jackets dresses never fit right but have a couple of t-shirt dresses, and of course girly shorts and heels.
8. What do you fantasize about crossdressing in most?
I rely don't but do fantasize about being dressed in some situations, like serving at an all girls sex party with a maids outside on, no panties, and having me used to demonstrate some of the "toys".
Or being forced to dress up in skirt, panties, bra, pantyhose and heels, then a guy is introduced who needs me over, lifts the skirt up, rips the hose off and violates my ass. Afterwords I experience an add to mouth, all this happens with a few girls laughing as they watch.
9. Bra or thong?
- - a bra insert the shirt
10. Latex or fishnets?
- - fishnet, I have a few including a bodysuit.
11. Skirt or shorts?
- - Tough one, a denim skirt is hardly noticed and fun, but at times I prefer woman's shorts, get a denim close to knew leangth and your sister might not even notice. O have gone shopping in non denim shorts and skirts
12. Pink or blue?
- - you kinda asked this Blue
13. Heels or flats?
- - hells of I don't have to be in then all day
14. Blonde or brunette?
Neither
15. Makeup or Wig?
Nail polish, I don't try to make myself out to be a woman, just a male that looked to gender bend. Why not, girls have been doing it for 100 years now.
16. Fake tits or natural?
- - fake after fun, but normally natural I stay, sometimes I wear a bra under a male shirt, to fun.

[Amandacd]

1.what i wore first moms bra panties grandma type
2.where bathroom my house
3.where Where thrift store
4. Cum after yes
5.color pink/black
6.sextoys dildos buttplugs
7.bought way more since tha
8.fantasize about sucking and being drillef
9.bra
10.fishnets
11.skirts
12.pink
13.heels
14. brunette
15. Both makeup and wig
16.little bit of both

[dwedgie]

1. What did you wear the first time you crossdressed?
Girls school uniform, blouse, skirt, tights , flat shoes
2. How long did you first wear it?
All day
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?
Any
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?
Sexy black dress, matching bra and thong / g-string , suspenders and stockings
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?
Make up
16. Fake tits or natural?
Natural

[LockMeSub]

1. What did you wear the first time you crossdressed?
Bra and panties
2. How long did you first wear it?
Just a few hours
3. Where is the best place you've gone while dressed up?
To a neighbors house he had no idea
4. Did you usually cum after crossdressing?
I used to
5. What colour is the clothing you like best?
Pink and Purple
6. Did you use any sextoys? Which ones?
Yes Dildos, Butt plugs, Gags, Vibrators
7. Have you bought more clothes to crossdress in since then?
Many more panties and bra's
8. What do you fantasize about crossdressing in most?
Being a girl and pleasuring men as a woman
9. Bra or thong?
Bra
10. Latex or fishnets?
Fishnets
11. Skirt or shorts?
Skirt
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

[rhl]

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?
publicly girls blue jeans, in private my sisters one piece bathing suit and panties
2. How long did you first wear it?
a few minutes for bathing suit. All day has panties under the jeans. On one day a Girl at work noticed the pants where ladies
3. Where is the best place you've gone while dressed up?
took a 3 mile walk around a tree less pond. In stockings heels, micro skirt, stuffed bra and thin ladies top. The walk took over an hour and passed several Jewish ladies in their long black skirts
4. Did you usually cum after crossdressing?
no, never
5. What colour is the clothing you like best?
doesn't matter
6. Did you use any sextoys? Which ones?
usually not when CD
7. Have you bought more clothes to crossdress in since then?
yes mostly in personb
8. What do you fantasize about crossdressing in most?
being able to convincingly dress up and act as a lady for a complete week
9. Bra or thong?
both
10. Latex or fishnets?
fishnets
11. Skirt or shorts?
skirt but have been known to take walks with booty shorts and butt pads
12. Pink or blue?
yes
13. Heels or flats?
depends on how long, but i do like wearing heels while dressed in male clothing.
14. Blonde or brunette?
never thought about tgis
15. Makeup or Wig?
wig
16. Fake tits or natural?
padded fake