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Old 06-10-2015, 09:16 AM   #1
ben_sissy99
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Female Crossdressing Questions

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?
2)How old were you when you first STARTED crossdressing?
3)When you first started crossdressing, who's clothes did you wear? (Persons age, relationship, size etc.)
4)How did you find out about cross dressing originally and what made you want to start it?
5)For how long were you crossdressing before you got found out or told anyone? (Assuming you have)
6)What is the most daring crossdressing activity/dare you've done?
7)What's your favorite cross dressing clothes to wear?
8)When did you buy your first crossdressing clothes?
9)What's the most public crossdressing thing you've done? (This may overlap with 6)
10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy?
11)Are you looking for someone to help with your crossdressing (A master, switch?) if so leave details
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Old 06-10-2015, 01:06 PM   #2
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1)How old were you when you first HEARD about cross dressing?
-I guess however old I was when Mulan came out.
2)How old were you when you first STARTED crossdressing?
-I was... I think 12?
3)When you first started crossdressing, who's clothes did you wear?
-My mother's...
4)How did you find out about cross dressing originally and what made you want to start it?
-I was just a curious kid and I went looking through my mom's drawers.
5)For how long were you crossdressing before you got found out or told anyone?
-My mom walked in on me in a skirt about a month after I started playing around. She went ballistic.
6)What is the most daring crossdressing activity/dare you've done?
-I went shopping for a couple hours with a bra and some frilly panties on.
7)What's your favorite cross dressing clothes to wear?
Thongs... They're just so conforming to a small cock.
8)When did you buy your first crossdressing clothes?
-A couple years ago, I didn't buy much, just a small pink lacey thong. It's gone now tho.
9)What's the most public crossdressing thing you've done? Six would answer this.
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 like to be turned into a full sissy outfit with panties, bras, and skirts and dresses the whole deal. I don't think I could live all the time like a woman, but it would be good for short periods of time.
11)Are you looking for someone to help with your crossdressing? Maybe a little bit, but I have no clothes to do it with except a few panties.
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Old 06-10-2015, 01:14 PM   #3
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1)How old were you when you first HEARD about cross dressing?
8
2)How old were you when you first STARTED crossdressing

10

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

My collage sisters

4)How did you find out about cross dressing originally and what made you want to start it?

I tried her bra

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

10 years then I got breast implants and started pre srs

6)What is the most daring crossdressing activity/dare you've done?

getting breast implants

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

My corset dress and teddy

8)When did you buy your first crossdressing clothes?

14

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

Breast implants

10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy?

Getting srs and is coming soon

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

nope got one
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Old 06-10-2015, 03:13 PM   #4
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1)How old were you when you first HEARD about cross dressing? 15
2)How old were you when you first STARTED crossdressing? 8
3)When you first started crossdressing, who's clothes did you wear? (Persons age, relationship, size etc.) skirts and dresses
4)How did you find out about cross dressing originally and what made you want to start it? a friend told me, and well I started at 8 and never stopped
5)For how long were you crossdressing before you got found out or told anyone? (Assuming you have) 7 years
6)What is the most daring crossdressing activity/dare you've done? went out in public, but was attacked :[
7)What's your favorite cross dressing clothes to wear? dresses :3
8)When did you buy your first crossdressing clothes? 16
9)What's the most public crossdressing thing you've done? (This may overlap with 6) went out for a night
10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy? Dont have one.
11)Are you looking for someone to help with your crossdressing (A master, switch?) if n/a
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Old 06-10-2015, 04:53 PM   #5
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1)How old were you when you first HEARD about cross dressing? Heard the word at about 20
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 sister (19) and mother (40).
4)How did you find out about cross dressing originally and what made you want to start it? Don't know what pushed me but tried stockings and found it delicious. So tried more and more things
5)For how long were you crossdressing before you got found out or told anyone? (Assuming you have) Told to a stranger , once, after 20y of XD
6)What is the most daring crossdressing activity/dare you've done? Going to stranger know via craiglist ad, crossdress there and give him a blow job
7)What's your favorite cross dressing clothes to wear? Corset, high heels, stockings, black short dress
8)When did you buy your first crossdressing clothes? At about 25
9)What's the most public crossdressing thing you've done? (This may overlap with 6) Wearing woman clothes undre my males ones
10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy? Being fully shaved and forced to crossdress. I'd love it to happen.
11)Are you looking for someone to help with your crossdressing (A master, switch?) if so leave details. I'm but I'm in couple, so it's complicated.
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Old 01-07-2016, 12:25 PM   #6
SissyVictoria
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1)How old were you when you first HEARD about cross dressing? 16
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 mom's who was around 32 at the time's swimsuit and panties.
4)How did you find out about cross dressing originally and what made you want to start it? Not sure, just liked the way the women looked in my father's porn mags
5)For how long were you crossdressing before you got found out or told anyone? (Assuming you have) 20 years
6)What is the most daring crossdressing activity/dare you've done? Wore bra, panties, garter, stockings and a plug under my male clothes and went to the adult bookstore to buy a movie and toy.
7)What's your favorite cross dressing clothes to wear? Granny panties and bras
8)When did you buy your first crossdressing clothes? Was 18
9)What's the most public crossdressing thing you've done? (This may overlap with 6) Wore bra, panties, garter, stockings and a plug under my male clothes and went to the adult bookstore to buy a movie and toy.
10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy? Being dressed in full lingerie when my Mistress brings home 2 or more men for me to service and for me to be spitroated while she watches and pleasures herself. Would love it to actually happen.
11)Are you looking for someone to help with your crossdressing (A master, switch?) if so leave details No, have a Mistress already
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Old 01-07-2016, 01:34 PM   #7
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1)How old were you when you first HEARD about cross dressing?
Not Sure

2)How old were you when you first STARTED crossdressing?
14 ish

3)When you first started crossdressing, who's clothes did you wear? (Persons age, relationship, size etc.)
Mothers (cringe)

4)How did you find out about cross dressing originally and what made you want to start it?
Kinky from day one !

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

6)What is the most daring crossdressing activity/dare you've done?
Having silk panties on show above my waist band in public

7)What's your favorite cross dressing clothes to wear?
Panties / swim suets

8)When did you buy your first crossdressing clothes?
?

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

10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy?
My wife to do my make up and wig etc then fuck me with a strap-on

11)Are you looking for someone to help with your crossdressing (A master, switch?) if so leave details
No way!
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Old 01-07-2016, 01:49 PM   #8
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Default This seems interesting

1)How old were you when you first HEARD about cross dressing?

Tough one. I knew I'd like to cross-dress long before I knew it was a thing. I heard about actual cross-dressing sometime around the age of 14, but I knew I wanted to do it from as young as I can remember.

2)How old were you when you first STARTED crossdressing?

I first cross-dressed, and not fully, at University when 18. I didn't do it again until I was 24 and I didn't do it with anything approaching regularity until I turned 25.

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

I've always owned the clothes.

4)How did you find out about cross dressing originally and what made you want to start it?

I found it was a 'thing' in a top-shelf magazine, that I bought to read more about it (not the best choice). As to what made me want to start, pass, it's been part of me as long as I can remember.

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

I intimated to my first (and at the time only) ex-girlfriend when I was 21 that I may be a transvestite. At that point I had worn a pair of knickers, once, when I was 18.

6)What is the most daring crossdressing activity/dare you've done?

Running whilst cuffed in a dress in the house with my wife asleep upstairs.

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

A dress I bought, with tights, shoes and underwear.

8)When did you buy your first crossdressing clothes?

I was 25, a pack of 5 black knickers (tanga style) from the local supermarket.

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

Going to a club with my second girlfriend, who was a bit nuts, in a minidress for an evening.

10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy?

Oooh, actually, I don't know.

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

I can't imagine anyone wishes to be a master or mistress to a cross-dresser such as myself. My experience suggests that most people are not interested in it, despite the many who would like to be dominated and cross-dressed.

That said, if anyone IS interested... I'm in my 30s, professional job, have a family (including a wife but we're not physical any more) and work with vulnerable people - so workplace dares are out. Happy to discuss with people who would like to dominate but I suspect I'd make an awful sub. I've very likely got Asperger's but I'm high functioning and I am socially inept.

PM me.
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Old 01-07-2016, 10:56 PM   #9
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1)How old were you when you first HEARD about cross dressing? 12
2)How old were you when you first STARTED crossdressing? 14
3)When you first started crossdressing, who's clothes did you wear? (Persons age, relationship, size etc.) Mine, I got my mom to buy them
4)How did you find out about cross dressing originally and what made you want to start it? I found it when I was looking through porn sites.
5)For how long were you crossdressing before you got found out or told anyone? (Assuming you have) I didnt crossdress until I owned anything
6)What is the most daring crossdressing activity/dare you've done? I wore a dress to school for the whole day
7)What's your favorite cross dressing clothes to wear? My skirt, pushup bra, neon pink top and kneehighs.
8)When did you buy your first crossdressing clothes? At age 14
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? To find a daddy that wants me to crossdress all the time with him when I feel like it so I can truly be genderfluid

11)Are you looking for someone to help with your crossdressing (A master, switch?) if so leave details. Yes I'm looking for a master/daddy! Pm me
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The most daring thing I've done is gone on a short walk on a path in the woods while crossdressed. I think someone on the beach nearby saw me too.
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Old 01-08-2016, 02:06 AM   #10
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1)How old were you when you first HEARD about cross dressing? Don't remember exactly but I was young.

2)How old were you when you first STARTED crossdressing? Probably 10 or younger.

3)When you first started crossdressing, who's clothes did you wear? (Persons age, relationship, size etc.) I was the fortunate son of a mother who ran a dance studio and had a endless access to many perfectly sized dance costumes, tights, dresses, unitards, leotards, etc...

4)How did you find out about cross dressing originally and what made you want to start it? I loved the feel of the tight clothing. Silky smooth. Started wearing it and it turned me on tremendously.

5)For how long were you crossdressing before you got found out or told anyone? (Assuming you have) I've told many people since I was 18 however once when I was 16 my stepsister found her bathing suit in my room. Don't know if she knew exactly why it was there but close.

6)What is the most daring crossdressing activity/dare you've done? I would never need to be dared for crossdressing activity. I have gone out for the day, night fully dressed a handful of times. My mother once told me she didn't recognize me until I spoke however that was on Halloween so she doesn't know other than that.

7)What's your favorite cross dressing clothes to wear? My favorite day to day would be thongs. My favorite otherwise which I currently don't own is a corset.

8)When did you buy your first crossdressing clothes? I think I was 14.

9)What's the most public crossdressing thing you've done? (This may overlap with 6) Well I almost always wear thongs sometimes a bra or tight silky tank top and tights under my clothes. Have spent days out with friends cross dressed completely but only a few times.

10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy? I live my fantasy. I have an accepting wife who enjoys it with me however we have never gone out with me dressed yet but I feel it coming soon. I mostly enjoy wearing it under my clothes all day.

11)Are you looking for someone to help with your crossdressing (A master, switch?) if so leave details. No I don't need help. I have always lived around more women than men. I can do my nails, makeup, hair (wig), outfit. It just comes naturally, however I am not interested in it to get with men. I enjoy the feel of the tight clothing, the makeup, the whole thing it just turns me on. If I were as people say a woman trapped in a man's body I would be a lesbian. And I also would never want to be in dress all the time. I enjoy the stuff I can wear under my clothes the most.
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Old 01-08-2016, 08:35 AM   #11
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1)How old were you when you first HEARD about cross dressing? 11
2)How old were you when you first STARTED crossdressing? 8
3)When you first started crossdressing, who's clothes did you wear? (Persons age, relationship, size etc.) mother and sister
4)How did you find out about cross dressing originally and what made you want to start it? Just did it first, found out about it later
5)For how long were you crossdressing before you got found out or told anyone? (Assuming you have) 17 years - told G/f
6)What is the most daring crossdressing activity/dare you've done? Been to sex club fully dressed and had sex with g/f in front of strangers, been outdoors in public,
7)What's your favorite cross dressing clothes to wear? Lingerie generally, always stocking not tights, the slutty look
8)When did you buy your first crossdressing clothes? 16
9)What's the most public crossdressing thing you've done? (This may overlap with 6) yup see above
10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy? X dressed at night outdoors, caught by 5 guys, used and abused by them
11)Are you looking for someone to help with your crossdressing (A master, switch?) if so leave details looking for a master or switch - pm me here
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Old 01-08-2016, 04:06 PM   #12
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1)How old were you when you first HEARD about cross dressing?
After I was testing the waters

2)How old were you when you first STARTED crossdressing?
Wore panties for the first time around 13

3)When you first started crossdressing, who's clothes did you wear? (Persons age, relationship, size etc.)
My neighbor (she was a year older), my mom's, and two different friend's mom's

4)How did you find out about cross dressing originally and what made you want to start it?
I remember feeling the softness of panties when I was young and liked the feel, and then I saw pictures of girls in panties and figured I'd like to try it.

5)For how long were you crossdressing before you got found out or told anyone? (Assuming you have)
I told someone about two years ago, so at 25

6)What is the most daring crossdressing activity/dare you've done?
Wearing a bra under my hoodie while driving

7)What's your favorite cross dressing clothes to wear?
I just discovered yoga pants and I love them more than I can explain. Other than that, stockings and panties.

8)When did you buy your first crossdressing clothes?
21 or 22, just some panties.

9)What's the most public crossdressing thing you've done? (This may overlap with 6)
Same as #6. I wear panties/stockings to work a bit.

10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy?
I'd like to be in chastity for months by a girl and she has me start crossdressing, and when at home I'm either naked or in girls clothes.

11)Are you looking for someone to help with your crossdressing (A master, switch?) if so leave details
Yea, females only though.
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Old 01-18-2016, 08:06 PM   #13
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1)How old were you when you first HEARD about cross dressing? not sure

2)How old were you when you first STARTED crossdressing? 32

3)When you first started crossdressing, who's clothes did you wear? My own with some of my girlfriends jewelry

4)How did you find out about cross dressing originally and what made you want to start it? I jsut had and urge and was alone for a weekend so tried it out

5)For how long were you crossdressing before you got found out or told anyone? I told my girlfriend when she got home, she noticed I had shaved

6)What is the most daring crossdressing activity/dare you've done? Tied between 2

1. When I first started I put on just makeup and nail polish, went into the women's clothes store and bought a skirt and some tops, then changed into them. Then walked to the shoe store and asked for help and put those on. Then I went around to different stores shopping like this

2. Got dressed up in really slutty clothes, like 5 inch school girl skirt, pink panties, top, falsy breasts and bra, lipstick, thigh highs on a windy day. Walked out my backdoor and walked 15 blocks away in a major city then walked back. Every time the wind blew my skirt showed my panties

7)What's your favorite cross dressing clothes to wear? Super slutty basically bedroom lingerie, especially in public. I've gone to adult stores and gotten costumes then worn them home on the subway

8)When did you buy your first crossdressing clothes? Day 1 see number 6

9)What's the most public crossdressing thing you've done? See 6

10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy?

Get dressed as slutty as possible, have a dom lead me on a leash and dog collar into sephora and have them do my makeup ultra slutty or porn starry. Then she leads me around ultra public places and brings me into clubs to hit on men. And yes I am actively looking to do this.

11)Are you looking for someone to help with your crossdressing? Always like masters and dommes
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Old 01-20-2016, 08:04 PM   #14
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1)How old were you when you first HEARD about cross dressing? About 12
2)How old were you when you first STARTED crossdressing? 14-ish
3)When you first started crossdressing, who's clothes did you wear? (Persons age, relationship, size etc.) At the very beginning I wore my mothers, but quickly became weirded out by it and bought my own.
4)How did you find out about cross dressing originally and what made you want to start it? I found out about it on the internet and was kind of always interested with being forced by girls to dress up in their clothing, so I began because of how it made me feel.
5)For how long were you crossdressing before you got found out or told anyone? (Assuming you have) 4 years
6)What is the most daring crossdressing activity/dare you've done? I wore panties and stockings to class for a week
7)What's your favorite cross dressing clothes to wear? Usually dresses and jumper skirts, but it depends on the mood I'm in.
8)When did you buy your first crossdressing clothes? When I was 15
9)What's the most public crossdressing thing you've done? (This may overlap with 6) I played a role playing game where we were all maids with some friends. We were all in costume of course.
10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy? To have a gf who enjoyed dressing up with me. We'd choose each other's outfits and do each other's makeup and have a sort of girl's night where we just had fun and cuddled. Ofc good sex would be involved as well. This would ideally be more than just a fantasy at some point too.
11)Are you looking for someone to help with your crossdressing
Yes, a girlfriend or mistress would be perfect
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Old 01-21-2016, 09:09 AM   #15
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1)How old were you when you first HEARD about cross dressing?
I think i was 15
2)How old were you when you first STARTED crossdressing?
13 or 14
3)When you first started crossdressing, who's clothes did you wear? (Persons age, relationship, size etc.)
I start with my mother (46 at that time) pantyhose and skirt
4)How did you find out about cross dressing originally and what made you want to start it?
I have a thing for pantyhose and stocking, and when i discover the feeling of pantyhose i just wanted to try more women clothes
5)For how long were you crossdressing before you got found out or told anyone? (Assuming you have)
No one found out and i told no one
6)What is the most daring crossdressing activity/dare you've done?
going in a mall with a pink thong, black stockings and pink bra under my boy clothes and every time i bend down feel the rush and the fear that someone notice my pink thong. I'm someone shy so for me it was a big thing
7)What's your favorite cross dressing clothes to wear?
Satin panties, garter belt, stockings and high heels.I really want to try a corset and a bodystocking but i'm always worried that the size won't fit me
8)When did you buy your first crossdressing clothes?
think i was 17 and i buy a leggings and a pantyhose in a supermarket. the feeling when i first try this legging <3
9)What's the most public crossdressing thing you've done? (This may overlap with6)
yeah look at question 6
10)What would your ideal cross dressing fantasy be? And would you like it to actually happen or is it just a fantasy?
Be fully crossdress, completly shave, makeup, nail polish, wig or natural long hair, girly outfit, jewelry, handbag... And go with crossdresser friend or girl friend on a shopping day and finish the night in a bar or club flirting with men
11)Are you looking for someone to help with your crossdressing (A master, switch?) if so leave details
if someone want to help me achieve my crossdressing fantasy i wouldn't mind, master, mistress, or other crossdresser
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