Crossdresser Questionnaire

I saw this on Facialbook, and it looked fun.  As long-time readers of this blog know, I consider crossdressers to be part of the transgender tapestry.  "There but for the grace of God" and all that.  Most crossdressers I know (and I know many) would transition if they could, but circumstances prevent that.  I know a few who dress purely for the enjoyment of "art."  But not many.  

I'll put a "clean" copy in the comments for those that wish to fill it out for their social media. 

A lot of these questions were covered by previous blog entries, which I will link where appropriate.

As none of these questions reveal anything about passwords or such, here we go...

************************************************************************

100 Crossdressing Questions Answered

1. How old were you when you realized you were different? 

Four.  I remember it distinctly. 

2. How old were you when you first tried wearing women’s clothes, make up etc? 

Mum dressed me as a girl for Halloween when I was seven.  Aside from that, I was twelve when I started dressing on my own.  

 

3. Have you ever told anyone you were a Crossdresser?

Before coming out to my wife, no.  Now everyone knows my "dark secret."

4. At what age did you come up with your femme name? 

It was December 2008, so I was 42.  Details HERE.

5. Did you use any other femme names before you chose your current name if so what was it?

For maybe a month before Sophie, I was Lisa.  Lisa is now my middle name to honor Lisa Empanada. 

6. How did you come up with your Femme name?

Karen at Femme Fever gave it to me.  Details HERE (same link as above)

Femme Fever Dec. 2008

7. Have you ever been caught dressed?

Once, by my older brother. Story HERE.  I had several close calls, but only caught the one time- and that was because I was wearing makeup. 

8. How did the people you told take it?

Wife took the crossdressing part as well as could be asked.  I lost 90% of my friends.  Many said they'd support me than disappeared.  My family disowned me for a while.  Mother in law threw me out.   

9. Are you married? 

Yes. 

10. Does your spouse know? and if so are they accepting? 

Yes.  See #8 above.

11. What was the first article of women’s clothes you ever bought?

Pantyhose.  Leggs. In the plastic egg.

12. What was the last article of women’s clothes you bought? 

A swimsuit.  One piece.

13. Long or short skirts? 

I used to love short skirts, but now I prefer mid or knee length.

14. Do you venture out dressed? If yes how often do you go out dressed? 

Well, yes.  I've been full time for over ten years.  

15. If you could go back and change one thing about your Crossdressing what would it be? 

Wow.  Maybe not beat myself up for it all those years.  Or not to have the urge to do it (which turned out to be gender dysphoria.)

16. Do you feel being a Crossdresser makes you a better person? If yes how so? 

It caused me a lot of pain and pleasure.  The pain of lying to my wife, and the eventual destruction of my life as I knew it.  In the end, I am a better person, as before transition, I was an angry asshole.  The anger is mostly gone now.  I may not be happy, but I am at peace.

17. How long were you dating / married before you told your significant other or spouse?

We had been married 19 years at that point.  

18. What is your favorite article of clothing? 

I have a favorite bra, but my fave has to be my teal dress.  I like it so much that I bought a second one which waits, still in its plastic, if the other one is ever ruined or torn or whatever.

This dress (#18 above)

19. If you have bought your own clothes, have you ever had any issues with store clerks?

No, I never have.  Funny, right?

20. What is your greatest Crossdressing accomplishment?

I think it's an accomplishment that I went out in public at all.  I'd have to say it was the friendships I developed over time.  If not for people like my "big sister" Mel, Lisa Empanada, Linda Lewis, Ally Raymond, Amanda Richards, Victoria Datta, Kimberly Huddle, Jenny J, and Jen L, and so many others, I would be long dead.  

21. What is your favorite brand of make up?

MAC.  It usually works for me.  

22. Do you wear perfume? If yes what is your favorite fragrance?

I do when I get really dressed up.  I usually wear Clinique "Happy".  Do they even make that nay more?  I'm almost out.

23. How many lipsticks do you own? 

Umm... I never counted.  Somewhere around 10 I think.  Mostly MAC, but some others. 

24. What is your favorite color of lipstick called?

MAC "Syrup" is what I wear the most.

25. Did you buy breast forms or do you make your own?

I bought them, and eventually sold them on eBay.  My breasts are all natural now.  

26. Do you ever have dreams related to Crossdressing? if yes what was it? 

Funny enough, no.  All my life I would be female in some dreams, male in others, or switch back an forth.  Still that way.

27. When not dressed how often do you think about it, for example while at work? 

I used to- really often.  When I was dressing once a month, I would plan my outfits all month.

28. Favorite hair removal method? 

I did laser, and some electrolysis.  The laser lasted around 10 years, but my beard is now coming back.  It's frustrating.

29. If you could spend a day with anyone else dressed who would it be? 

As I'm full time, this no longer applies really.  I love hanging out with my friends as it's been so long.

30. Do you have space in the closet for your clothes or do you have to hide them? 

At first I hid them in boxes in the basement, labeled "Games." We'd moved from Baltimore and most of our stuff were in boxes in the basement.  I eventually got a storage space, which came in handy when I was thrown out.  Now, they are the only clothes I have.

31. Have you ever purged your clothes? 

August 1983.  I was going to be a MAN, and men don't wear dresses.  I fell into a deep depression and couldn't understand why.

32. Given the opportunity would you take a job where you could work as either your male or female self at any time? 

Again, not applicable.  I'm full time.  

33. Do you paint your natural finger nails or use fake ones? 

I have some fake nails for special occasions, but usually natural. 

34. What Color do you like to use on your finger nails? 

Brilliant red, but lately I've done others.

35. Do you keep your toe nails painted? 

No, except when I treat myself to a pedicure.  

36. What color nail polish do you like best on your toes? 

Usually brilliant red.  I'm dull.

37. If you wear make up what part do you find the hardest to learn how to do? 

Eyes- specifically fake lashes.  I've never been able to do those.

38. Have you ever had a professional make over? 

Yes. Mostly from the legendary Amanda Richards, but not all.  I love makeovers.  

39. Have you ever worn a Bikini or other swimsuit? 

Yes 

40. Do you own or have you ever worn a Wedding Dress?

Yes, at an Amanda Richards photoshoot.  

41. Do you own a wig or use your own hair? 

My own hair, but I may have to go back to wigs due to hair loss. I still have wigs.

42. How often are you able to dress up during the week? 

24/7/365.  I paid the price.

43. How many Blouses do you own? 

No idea.

44. How many Skirts do you own? 

No idea.

45. How many Dresses do you own? 

No idea.

46. How many bra’s do you own? 

Over 20.  I should go through them... 

47. How many pair’s of panties do you own? 

Around 20.  Maybe 5 shapewear. 

48. What is your favorite color for lingerie? 

Red or black.  My daily ones are usually black or buff.

49. Pantythose or Thigh Highs? 

I don't have occasion to wear them, but I prefer pantyhose. 

50. Favorite place to shop for misc items? 

I prefer to shop local.

51. Favorite place to shop for Make up? 

Ulta is the only place in town.

52. Favorite place to shop for clothes? 

Torrid, Long Tall Sally

53. Favorite place to shop for Lingerie? 

I usually get that from online as there's few place around here.

54. Best time you can think of spent dressed up? 

Two come immediately to mind.  Lisa's affirmation party, and the Debutante Ball that friends threw for me on my one-year transition anniversary.

Debutante ball

55. If you could have the ultimate day out where would you go? 

A day on vacation with my wife, daughter, and Linda.  Somewhere fun.  

56. Funniest thing that’s ever happened to you while Crossdressing? 

I've had many fun times with my dear friends.  I can't think of one right now.  If I do, I'll add to this.  

57. Do you have pierced ears or wear clip ons?

Pierced.  It was one of the first things I did.  2009?  2010?

58. Do you wear heels? 

When I have an occasion, yes. 

59. How long did it take you to learn how to walk in heels? 

I used to practice this.  Many hours.

 

60. How many pairs of heels do you own? 

Maybe 10. My day to day are flats.

61. Name an article of Women’s clothing you can’t live without? 

Bras. I mean, duh.

62. What is one article of Women’s clothes you don’t like? 

Tops that bare the midriff.

63. Do you sleep in a nightie?

Occasionally.  

64. What type of panties do you like? 

I love the silky ones, but most of mine are cotton.

65. What is your Favorite color for a dress? 

I'm told that I look good in jewel tones.  I also have a lot of black.

66. When you’re wearing pantyhose, what do you do with your junk? Let it be free or tuck it up and tape? 

I used to have to tuck but not anymore. 

67. What stops you from ‘dressing’ in public? Fear of yourself or of others? 

I was afraid of the consequences... almost all of which happened. 

68. When did you first know your taste in fashion was different from other boys? 

Around 4

69. When did you tell your wife? What was her reaction?

As above, May 3, 2012.  Story HERE. 

70. What would you tell your 5 year old self if you could? 

You aren't alone.  You aren't a freak.  

71. Do you shave your chest and armpits as well as your legs? 

Armpits.  Thanks to HRT, I don't really need to shave my chest.  Thank God, as furry boobs would suck.

72. Have you ever told anyone and they reacted badly? 

Almost everyone when I came out.  Aside from that, not really

73. What was your most surprising reaction when telling someone? 

I call him "R" in my blog.  Details HERE.

74. For most women, taking the bra off at the end of the day and having a good under-boob scratch is the equivalent to a man scratching his nut-sack. Is it the same when you take off your bra? 

Absolutely.  It feels great.  

75. How did you feel the first time you ‘dressed’? 

It felt “right”. It felt correct.  Like I was being me for the first time.

76. How did you feel the last time you ‘dressed’? 

N/A as I'm full time.

Last time I wore makeup- a couple of weeks ago

77. Do you and your wife share clothes? 

Hell no.  She's a petite woman and I'm a fat mess.

78. What do you wish everyone understood about why you dress that no one seems to really get? 

That being transgender is biological- e don't choose this.  And we aren't "groomers" or anything evil.  We just want to live our lives.

79. Do you prefer skirts and dresses or pants? 

Skirts and dresses. I wore pants for 47 years- that's enough.

 

80. How do you hide your 5 o’clock shadow? 

I use Mehron beard cover.  then foundation over that.   

81. If you could go somewhere on the planet where not one soul knew who you were and publicly dress, would you? 

Back in the day, I realized quickly that when I was fully enfemme, I was unrecognizable.  I may be clocked as a cd, but not as [dead name].  I avoided the places I frequented as a guy, though.  The funny part was that the party I'd go to was, for years, in a restaurant right next door to the bookstore where I worked.

82. Do you think you’ll ever tell your children? 

I did- right before I transitioned.  Story HERE.

83. What will you tell your children (if you don’t intend to tell them) and they find out accidentally?  

I never considered that, as she was 6 when I transitioned, and I never dressed as Sophie when she was home, so...

84. Why aren’t women who wear menswear considered cross-dressers? 

Because masculinity is fragile and must be proven almost every day, while femininity is never questioned.  A woman in guy clothes is still a woman- a lesbian is still a woman.  If a guy dresses as a female or is gay, other men consider him effeminate and therefore week and not a man.  There were many studies done on this, like:

Stanaland, A., Gaither, S., & Gassman-Pines, A. (2023). When is masculinity “fragile”? An expectancy-discrepancy-threat model of masculine identity. Personality and social psychology review, 27(4), 359-377. 

85. Where the hell do you find shoes to fit? 

On-line.  Such as HERE, HERE, and HERE among others.

86. What is the longest you have ever dressed for? 

123 months.  Or 536 weeks.  Or 3753 days.  You get the idea. 

87. Do your bra and panties have to match? 

Sometimes.  I don't really try to match them as nobody will see them.

88. Do you find there is a big difference between your male and female self? If so how? 

I was much angrier and in "pain" s a guy.  I felt like a failure as a man- unable to provide for my family, etc.  Now I'm at peace.  Not happy- just at peace.  And that will have to be enough.

89. Does it matter to you if you “Pass” or not? 

It would be great to pass, and I try to as much as possible, but it’s not really realistic.  I like to show cleavage as it's a feminine signal, but...

90. Do you “Pass”?

Hell no.

91. How long does it take you to get all dressed up? With makeup? 

Depends upon how much makeup.  Anywhere from 30- 90 minutes.  Back in the day it took at least 90 minutes. 

92. If you had a chance to remove your desire to Crossdress would you take it? 

Too late now, but yes- absolutely.

93. Do you have any female role models and if so who are they? 

As a crossdresser, they were Linda Lewis, Ana Christina Garcia, Heidi Phox, Kimberly Huddle... so many.  Now?  Sophie Scholl, Jennifer Finney Boylan, Donna Rose, others as well.  And every transgender woman who lives her Truth.  

With Ana Christina Garcia at Keystone Conference 2022

 

94. Do you listen to anything while getting ready? 

Sometimes.  Usually 80s stuff or Grateful Dead

95. What do you hope to accomplish by Crossdressing? 

This is really a stupid question.  If anything, I hoped to find peace and perhaps the companionship of people like myself.  I wanted to feel like I wasn't alone with this.

96. What do you expect crossdressing to teach you about being a woman and the experiences associated with it? 

I don’t pretend to know what a cisgender woman experiences. But I now understand what it means to be without male privilege, and what it means to have rights stripped away.

97. Do your personal or political views change as a result of the experiences of crossdressing? 

No.  I've always been a raging liberal.  However, it's made me more outspoken about rights, like I was in my teens/twenties.

98. Has your views on relationships changed with crossdressing in your life? 

No.  I just miss what I had with wife and daughter.   

99. What was your best Crossdressing experience? 

Aside from what was noted above, I'd say that first look into the mirror at Femme Fever at Sophie.  I didn't recognize myself.

Sophie's first picture

100. What was your worst Crossdressing experience? 

Aside from being thrown out, which wasn't really a "crossdressing" experience...  Easily Lisa's funeral.  I don't know how I survived that month.