100 Questions Someone might ask a Crossdresser

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I had some fun doing the 100 questions blog awhile back so after I completed that I decided 100 questions more geared for a Crossdresser would be even more fun.  Now as easy as you would think it might be I had to wrack my brain trying to come up with all of them and even had to call in some favours from friends and family to complete the whole list.  Questions 66 to 85 were compiled from the woman I work with and I am hoping my wife will contribute a couple as well.

Just like the other 100 question blog post I will be breaking it into 2 parts because 100 questions is a lot to read.

 

1. How old were you when you realized you were different?  I was at least 5 or 6 years old
2. How old were you when you first tried wearing women’s clothes, make up etc?  Around the age of 7 I think
3. Have you ever told anyone you were a Crossdresser? If yes who? I have told my wife, A friend and a co-worker
4. At what age did you come up with your femme name?  I picked Cynthia when I was about 26
5. Did you use any other femme names before you chose your current name if so what was it?  For awhile I used Anastasia.
6. How did you come up with your Femme name?  I had seen the name Cynthia somewhere before and really liked the sound of it.
7. Have you ever been caught dressed?  No.
8. How did the people you told take it?  Wife and friend were a little surprised and co-worker took it great.
9. Are you married?   Yes.
10. Does your spouse know? and if so are they accepting?  Yes she has known for at least 20 years now and is great about it.
11. What was the first article of women’s clothes you ever bought?  The very first item I ever bought was a skirt from a thrift store. 
12. What was the last article of women’s clothes you bought?  I bought a new dress about 2 months ago.
13. Long or short skirts?  Depends on my mood but at least to my knees or longer.
14. Do you venture out dressed? If yes how often do you go out dressed?  Never strayed past my back deck while dressed.
15. If you could go back and change one thing about your Crossdressing what would it be?  I would have started dressing in front of my wife a lot sooner.  She always told me I could but I was too self conscious.
16. Do you feel being a Crossdresser makes you a better person? If yes how so? I think I have a better idea how women feel and therefore understand them more.
17. How long were you dating / married before you told your significant other or spouse?  I think roughly 5 months.
18. What is your favourite article of clothing? A denim skirt that my wife gave me.
19. If you have bought your own clothes,  have you ever had any issues with store clerks?  Never had a issue as I make a list and tell the clerks that it’s for my wife.
20. What is your greatest Crossdressing accomplishment?  Buying clothes by myself.
21. What is your favourite brand of make up?  Mary Kay.
22. Do you wear perfume? If yes what is your favourite fragrance?  I have a terrible sence of smell so it would be a waste.
23. How many lipsticks do you own?  11
24. What is your favourite colour of lipstick called?  Berry Kiss.
25. Did you buy breast forms or do you make your own?  I have made a few sets from pantyhose and rice to a sewn set.
26. Do you ever have dreams related to Crossdressing? if yes what was it?  I have had only one that I can remember.  It involved my mother in law somehow finding out I dressed and then getting me a gift card to my favourite store.
27. When not dressed how often do you think about it,  for example while at work?  At least 10-15 times a day.
28. Favourite hair removal method?  Shaving.
29. If you could spend a day with anyone else dressed who would it be? I have always wanted to have a girls day with the wife.
30. Do you have space in the closet for your clothes or do you have to hide them?  Seeing as my daughter does not know it’s best to keep stuff as well hidden as I can.
31. Have you ever purged your clothes?  No.
32. Given the opportunity would you take a job where you could work as either your male or female self at any time?  Most likely not.  I have a hard enough time keeping male clothes looking good at work.
33. Do you paint your natural finger nails or use fake ones?  I use fake ones.  I use fake ones.  Way easier to clean up.
34. What Colour do you like to use on your finger nails?  Purples or pinks.
35. Do you keep your toe nails painted?  Only in the Fall and Winter
36. What colour nail polish do you like best on your toes?  Mostly a metallic purple
37. If you wear make up what part do you find the hardest to learn how to do?  I find eye shadow the hardest part for me to do. 
38. Have you ever had a professional make over?  No.
39. Have you ever worn a Bikini or other swimsuit?  No.
40. Do you own or have you ever worn a Wedding Dress?  No.
41. Do you own a wig or use your own hair?  I own a very cheap wig that does not look very believable.  For the most part I do have longer hair that I just pull back into a pony tail.
42. How often are you able to dress up during the week?  With a teenage daughter not at all save for under dressing.
43. How many Blouses do you own?  4
44. How many Skirts do you own?  6
45. How many Dresses do you own?  1
46. How many bra’s do you own?  8
47. How many pair’s of panties do you own? 15 or more
48. What is your favourite colour for lingerie?  Pink
49. Panythose or Thigh Highs?  I will wear both but thigh highs are so much easier and better looking in my opinion.
50. Favourite place to shop for misc items?  Shoppers Drug Mart. 

Questions 51-100

 

So that’s questions 1 to 50.  I still have about 15 or so questions that I have to complete before I can do questions 51-100.  I even went as far as to put it out on Twitter but never got any replies back.  So we will see what I can think of today.

Thanks for reading.

Cynthia

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3 thoughts on “100 Questions Someone might ask a Crossdresser

  1. A good read. Thanks for sharing. I look forward to 51-100. I’m sorely tempted to answer them (well those that I can) and post up myself – I’m not sure how you’d feel about that but it would be an interestig exercise.

    What is however clear to me is I’m not entirely sure whether my crossdressing forms/formed a particular type of crossdressing. I have only ever worn lingerie and whilst I have occasionally pulled on the odd shirt and blouse on a very very rare occasion, it was soon off as I preferred the lingerie look and covering it up just didn’t do it for me. The question is – am I a type?

    1. Thanks for the comment Gerrylynn. And by all means if you want to copy and past and do the questions yourself be my guest. Just please link it back to my blog as the original. I am hoping to have the last 50 questions posted tonight.

      Thanks

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