Crossdressing Questions

[SissySlutSamantha]

1)How old were you when you first HEARD about cross dressing?
probably about 6 or 7
2)How old were you when you first STARTED crossdressing?
dressed up as a kid but properly started dressing up when i was about 8
3)When you first started crossdressing, who's clothes did you wear? (Persons age, relationship, size etc.)
both my sisters who are 8 and 7 years older then me
4)How did you find out about cross dressing originally and what made you want to start it?
was made to put a princess dress on when i was about 7 years old and really liked the feeling of the material and carried on since then
5)For how long were you crossdressing before you got found out or told anyone? (Assuming you have)
think my family knows but haven't been physically caught
6)What is the most daring crossdressing activity/dare you've done?
wearing bra, panties, tights (pantyhose) and a girls shirt under my clothes and went out shopping for about an hour
7)What's your favorite cross dressing clothes to wear?
any fancy dress but want to try ballgowns
8)When did you buy your first crossdressing clothes?
ordered online at about 17/18
9)What's the most public crossdressing thing you've done? (This may overlap with 6)
same as 6.
10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy?
being dominated by a women and forced to crossdress and fucked, would love it to happen.
11)Are you looking for someone to help with your crossdressing (A master, switch?) if so leave details
not looking right now, but maybe in the future ;P

[feminizeme22]

1)How old were you when you first HEARD about cross dressing? 10
2)How old were you when you first STARTED crossdressing? 13
3)When you first started crossdressing, who's clothes did you wear? (Persons age, relationship, size etc.) my moma
4)How did you find out about cross dressing originally and what made you want to start it? saw it online and it looked fun
5)For how long were you crossdressing before you got found out or told anyone? (Assuming you have) not yet hehehe
6)What is the most daring crossdressing activity/dare you've done?fully dressed below neck pics
7)What's your favorite cross dressing clothes to wear? panties and mini skirt
8)When did you buy your first crossdressing clothes?online secret fem
9)What's the most public crossdressing thing you've done? (This may overlap with 6)nothing yet
10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy? to find a mistress who throws out my clothes and forces me ot live as a female for life
11)Are you looking for someone to help with your crossdressing (A master, switch?) if so leave details yes

[Thedirtyboyslut]

1)How old were you when you first HEARD about cross dressing?
Well, I used to watch a lot of TV when I was younger and lots of the shows I watch had comedic cross dressing so pretty young. But as a fetish, probably about 16 :P

2)How old were you when you first STARTED crossdressing?
It was late in to my teens, about 19. Before that I didn't have such free access to panties as I had at 19+.

3)When you first started crossdressing, who's clothes did you wear? (Persons age, relationship, size etc.)
My girlfriend. She was 19, same as me. Her size? I dunno but they fit me!

4)How did you find out about cross dressing originally and what made you want to start it?
Well, its a really long story but I'll give the short version. When I was about 15 I got access to the internet, I was very sexually active at a young age, so I ended up finding chatrooms. In the chatrooms were guys, all wanting to chat with girls (there wasn't that many) so I decided to pretend to be a girl so I can get myself off on the conversation. The more I did it the more I enjoyed being and prenting to be a girl. I finally found out men like that too so it grew from there hehe

5)For how long were you crossdressing before you got found out or told anyone? (Assuming you have)
About 7 years :P wow, that's long now that I think about it

6)What is the most daring crossdressing activity/dare you've done?
I'd have to say, get dressed up fully and go in to town. Seeing guts staring at me was amazing. It was a small town as well so I was always nearly found out

7)What's your favorite cross dressing clothes to wear?
Underwear! All the underwear, socks, Garter belts. All those accessories. I love dressing up but its the panties I enjoy the most :$

8)When did you buy your first crossdressing clothes?
Well, most of my things I've gotten my exgirlfriends. The only things I really buy are sex toys and sex outfits. Cuffs, collars, plugs etc but sometimes I do buy some nice panties to cheer me up

9)What's the most public crossdressing thing you've done? (This may overlap with 6)
It does overlap but I'd love to do more public stuff!

10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy?
Hmmm, that's a toughie. I'd have to say being taken for a week to a house with a Daddy or Mistress and be their sissy sex slave for the entire week. Sleep in a cage, plugged, having constant parties where I get to show off, waitress and be used in all manners of ways. And id actually want that to happen!

11)Are you looking for someone to help with your crossdressing (A master, switch?) if so leave details
Yes! I'd love someone to help or talk to, chat, be friendly and all that hehe

[wheelsoffeathers]

1)How old were you when you first HEARD about cross dressing?
I think i was 13-14

2)How old were you when you first STARTED crossdressing?
As a regular thing probably 11, though i would often pick more girly clothes for games when given the opportunity while younger


3)When you first started crossdressing, who's clothes did you wear? (Persons age, relationship, size etc.)
Cousin i think she was 13,


4)How did you find out about cross dressing originally and what made you want to start it?
The feel of the clothes always attracted me i felt more freedom than my normal boring ones.


5)For how long were you crossdressing before you got found out or told anyone? (Assuming you have)

more than a decade i tried explaining but was met with with a wall of intolerance from family and due to bullying from them just keep it a secret from'em.


6)What is the most daring crossdressing activity/dare you've done?
I spent a week as a woman when was lucky enough to save up to spend it away.

7)What's your favorite cross dressing clothes to wear?
I don't really have a favourite, i like to wear dresses with jeans/leggings though

8)When did you buy your first crossdressing clothes?
13 from a local charity shop,


9)What's the most public crossdressing thing you've done? (This may overlap with 6)

Would be went on holiday as a woman.


10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy?
I think to be a full feminized sissy would be the ultimate but just for it to be accepted would be wonderful also.

11)Are you looking for someone to help with your crossdressing (A master, switch?) if so leave details

Maybe but would have to depend on the person as they would need to be patient due to concerns and financial constraints

[Kylie.j.96]

1)How old were you when you first HEARD about cross dressing? I don’t know exactly, young tho.

2)How old were you when you first STARTED crossdressing? I was about 11 or 12

3)When you first started crossdressing, who's clothes did you wear? (Persons age, relationship, size etc.) my older sisters. She was a couple years older than me

4)How did you find out about cross dressing originally and what made you want to start it? I’m not sure. I was jealous of my sisters cute clothes tho. So I decided to try them

5)For how long were you crossdressing before you got found out or told anyone? (Assuming you have)my mom caught me a couple times when I was young.

6)What is the most daring crossdressing activity/dare you've done? Went to a few haloween parties

7)What's your favorite cross dressing clothes to wear? Other than bras and panties, I love school girl and cheerleading uniforms

8)When did you buy your first crossdressing clothes? I think I was 16

9)What's the most public crossdressing thing you've done? (This may overlap with 6) haloween parties

10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy? Have a girl force me to dress up and make me be her girlfriend for a couple weeks or more

[rhl]

I've noticed cross dressing/sissification are quite big on here, and admit, I too have been fascinated by it so have devised some questions about cross dressing for people of this mind to find out more about their compatriots

1)How old were you when you first HEARD about cross dressing? I can't say I ever heard about it,
2)How old were you when you first STARTED crossdressing? 13-14, started by wearing my sisters bikini
3)When you first started crossdressing, who's clothes did you wear? 20's clothing I took off clotheslines, or bought in a thrift shop.
4)How did you find out about cross dressing originally and what made you want to start it? can't say I found out, just thought it would be fun
5)For how long were you crossdressing before you got found out or told anyone? (Assuming you have) some have questioned if my pants are ladies pants, I've been codify wearing bras and panties
6)What is the most daring crossdressing activity/dare you've done? Getting in stockings, heels, panties, bra, short skirt and ladies sweater and go shopping in a K-Mart
7)What's your favorite cross dressing clothes to wear? Skirt, leggings, women's pants
8)When did you buy your first crossdressing clothes? In 20's
9)What's the most public crossdressing thing you've done? (This may overlap with 6) Going to a place with a coin operated massage chair. My black Mailer had pictures, and contacts I would not want to see pics. This is a message chair that holds the knees apart. My skirt was fingertip leangth. No panties, and with the chair set for 5 minutes. I was to excited over this for my black Mailer, my black mailer made me wear panties, then before sitting down, I had to remove these panties.

10)What would your ideal cross dressing fantasy be? To be dressed as a convincing women, then go to a store and be fitted for a bra, then spend the night out with the girls
And would you like it to actually happen or is it just a fantasy? Yes
11)Are you looking for someone to help with your crossdressing (A master, switch?) if so leave details If anyone has suggestions, PM me

[darkness991]

1)How old were you when you first HEARD about cross dressing? dont know exactly i think around 10
2)How old were you when you first STARTED crossdressing? when i was around 8 i started with thongs and after that i got more and more but i think at 12
3)When you first started crossdressing, who's clothes did you wear? (Persons age, relationship, size etc.) my mothers thongs and she had a dress in the attic
4)How did you find out about cross dressing originally and what made you want to start it? it made me horny and the more i got the more it turned me on
5)For how long were you crossdressing before you got found out or told anyone? (Assuming you have) i think about 10 years before i told someone
6)What is the most daring crossdressing activity/dare you've done?i went outside dressed up and then i had to fuck my ass with a buttplug right next to a road
7)What's your favorite cross dressing clothes to wear? very short plaid skirt push up bra croptop hold ups and high heels
8)When did you buy your first crossdressing clothes? i think i was around 16
9)What's the most public crossdressing thing you've done? (This may overlap with 6) i also did that next to a highway with a dildo but that wasnt on a dare so you pick
10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy? i would love to be dressed up really slutty by a mistress who would lock me in chastity and then a lot of men would fuck me in my ass and mouth while she watches. i would love it to become reallity but with a different girlfriend then the one i have now
11)Are you looking for someone to help with your crossdressing (A master, switch?) if so leave details. i love to dress up for others online and i do it sometimes for my gf

[Ash Willowthorn]

1)How old were you when you first HEARD about cross dressing?
As long as I can remember
2)How old were you when you first STARTED crossdressing?
as long as I can remember
3)When you first started crossdressing, who's clothes did you wear? (Persons age, relationship, size etc.)
My cousins clothes, I have only female cousins.
4)How did you find out about cross dressing originally and what made you want to start it?
It started with porn.
5)For how long were you crossdressing before you got found out or told anyone? (Assuming you have)
5 years
6)What is the most daring crossdressing activity/dare you've done?
Walked along the sidewalk late at night in a dress and make up.
7)What's your favorite cross dressing clothes to wear?
Dresses, and thigh high socks.
8)When did you buy your first crossdressing clothes?
I’ve always been to scared to buy my own
9)What's the most public crossdressing thing you've done? (This may overlap with 6)
Went walking along the sidewalk at night in a dress I’m sure I ended up on a couple security cameras
10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy?
Maybe just go out of town for a couple of days and only bring feminine clothes, I would like it to happen
11)Are you looking for someone to help with your crossdressing (A master, switch?) if so leave details[/QUOTE] I would love to make new friends, and create long lasting relationships. Preferably supportive friends, who encourage me to try new things.

[sissybill]

1)How old were you when you first HEARD about cross dressing? 12
2)How old were you when you first STARTED crossdressing? 12
3)When you first started crossdressing, who's clothes did you wear? (Persons age, relationship, size etc.) my friends sisters cathlic school uniform/she n i were 12/size small
4)How did you find out about cross dressing originally and what made you want to start it? my friend showed me his sisters catholic uniform n said put this on so i did
5)For how long were you crossdressing before you got found out or told anyone? (Assuming you have) been dressing for 12 yrs before my x-grlfriend caught me
6)What is the most daring crossdressing activity/dare you've done? i was dared too wear bra n pantys n drive on highway n get out n check my air in my tires
7)What's your favorite cross dressing clothes to wear? blk phose/mini skirt/ pantys/bra/big fake tits/see thru mesh top
8)When did you buy your first crossdressing clothes? wen i was 24
9)What's the most public crossdressing thing you've done? (This may overlap with 6) dressed fully n walked into a adult book store to buy lube
10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy? too be fully dressed n forced to gointo woods n tied to a tree n guys lift my skirt up n each fuck me 1 by 1
11)Are you looking for someone to help with your crossdressing (A master, switch?) if so leave details

[fiume]

1)How old were you when you first HEARD about cross dressing?
About 17
2)How old were you when you first STARTED crossdressing?
About 15
3)When you first started crossdressing, who's clothes did you wear? (Persons age, relationship, size etc.)
I wear underwear and sort skirt I" borrow it" from near by draining rope
4)How did you find out about cross dressing originally and what made you want to start it?
First I started then found about it
5)For how long were you crossdressing before you got found out or told anyone? (Assuming you have)
Only my wife knows for about 15 years and couple of my friends so me in women's underwear
6)What is the most daring crossdressing activity/dare you've done?
Gone swimming in women's swimsuits on public beach, or going for a walk with my dogs wearing women's underwear women's shorts and bra and women's t-shirt
7)What's your favorite cross dressing clothes to wear?
Everything
8)When did you buy your first crossdressing clothes?
About 15 years ago
9)What's the most public crossdressing thing you've done? (This may overlap with 6) answer in 6
10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy?
Been able to be dressed as a woman for a full week without being judged
11)Are you looking for someone to help with your crossdressing (A master, switch?) if so leave details
My kik is sissyfiume any ideas and advice is always welcome

[agolnafu]

lost a dare - so ordered to fill in this questionnaire:

1)How old were you when you first HEARD about cross dressing?
Do no know exactly - might be 20 yo

2)How old were you when you first STARTED crossdressing?
much later - some 10 years ago

3)When you first started crossdressing, who's clothes did you wear? (Persons age, relationship, size etc.)
panties - bra - stockings

4)How did you find out about cross dressing originally and what made you want to start it?
an order exposure platform where you could give 'anonimous'orders to the other

5)For how long were you crossdressing before you got found out or told anyone? (Assuming you have)
nobody knows - only online contacts

6)What is the most daring crossdressing activity/dare you've done?
taking pics of me in cross dress in a toilet stall in high way petrol station - so some kind of semi public

7)What's your favorite cross dressing clothes to wear?
thigh high boots- fishnets - bra - panties - short colorfoul dresses

8)When did you buy your first crossdressing clothes?
soem 5years ago

9)What's the most public crossdressing thing you've done? (This may overlap with 6)
basically it was nr 6

10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy?
no, it is more that a fantasy. Could most probably become true: being pushed semi public in my most favorite outfit

11)Are you looking for someone to help with your crossdressing (A master, switch?) if so leave details
Yes, basically a switch - so we could mutually give cross dressing related orders to push each other limits step by step

[footlover.london]

1)How old were you when you first HEARD about cross dressing?
Hard to say but probably early teens. Maybe younger. I didn’t think much of it at the time/ it wasn’t an immediate interest.

2)How old were you when you first STARTED crossdressing?
My first small experience was probably wearing tights (pantyhose) while having fun by myself. This was quite infrequent though. First time dressing fully was much more recent - maybe early or mid 30s.

3)When you first started crossdressing, who's clothes did you wear? (Persons age, relationship, size etc.)
It was my sisters tights. Generally nude colour but sometimes black. Just because they were easy to access. I later used my wife’s, including knickers, panties and bras. I’ve also bought underwear and clubwear for myself in recent years

4)How did you find out about cross dressing originally and what made you want to start it?
I think I was initially attracted to the texture and different feel. It later developed into feeling vulnerable and submissive

5)For how long were you crossdressing before you got found out or told anyone? (Assuming you have)
Never told in real life. Online has been quite contemporaneous

6)What is the most daring crossdressing activity/dare you've done?
Probably a video strip from fully dressed, with heels and dress plus lingerie and stockings. I had a hood on, so no face, but I was still so nervous. I’d love to dress in a sissy club in person one day perhaps.

7)What's your favorite cross dressing clothes to wear?
Love stockings. It’s just the feel. Also knickers, lacy or silky. Especially if I’m in chastity.

8)When did you buy your first crossdressing clothes?
Only fairly recently. Maybe two or three years ago.

9)What's the most public crossdressing thing you've done? (This may overlap with 6)
Never public. But I’d like to try one day.

10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy?
I think dressing with others in a sissy club then all being made to perform together. Maybe being used orally too. It’s just a fantasy for now but I’d love to work up the confidence to try.

11)Are you looking for someone to help with your crossdressing (A master, switch?) if so leave details
I’d quite like too. Could be fun. Or even just other sissy boys. Feel free to message on here or kik (I’m based in London).

[rhl]

I've noticed cross dressing/sissification are quite big on here, and admit, I too have been fascinated by it so have devised some questions about cross dressing for people of this mind to find out more about their compatriots

1)How old were you when you first HEARD about cross dressing? When I started, I don't think I heard about crossdressing
2)How old were you when you first STARTED crossdressing? In my teens, I started wearing my sisters bikini
3)When you first started crossdressing, who's clothes did you wear? (Persons age, relationship, size etc.) My sisters and moms.
4)How did you find out about cross dressing originally and what made you want to start it? When I got in my 20's, I went to a store, picked out a few girls blue jeans and tried them on, picked one to by. No one seem to notice right away.
5)For how long were you crossdressing before you got found out or told anyone? (Assuming you have) it was a few months, when a co-worker asked me why I had ladies pants on.
6)What is the most daring crossdressing activity/dare you've done? Wearing a. 10" skirt commando with a t-shirt while shopping for leggings
7)What's your favorite cross dressing clothes to wear? When not in diapers, I'm love my panties.
8)When did you buy your first crossdressing clothes? In my 20's
9)What's the most public crossdressing thing you've done? (This may overlap with 6) shopping wearing bra, cami, panty, skirt, and heals. I also like dressing in male outfit wearing heals, or maybe one obvious female item.
10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy? Yes I would like to. Dress up on skirt, stockings bra, etc to the point I can pass as a girl, then go out with the girls and get hit on by a guy. Of course I'm encouraged to hook up with him and I soon find us embracing and I give him a BJ
11)Are you looking for someone to help with your crossdressing (A master, switch?) if so leave details I've thought about going to a cross dressing school.

I rarely am seen without having some female item on, shoes, panties, pants, leggings, or stockings. (stockings are required when diapered)