100 Questions Someone might ask a Crossdresser


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.

If you would like to answer the 100 Questions yourself you can get a blank copy of them from here.

Thanks for reading.



The History of Cynthia: 1989


In 1989 Make up ads looked like this


The number one song was Look Away by Chicago.


And the world lost the beautiful and funny Lucille Ball.


We have moved 6 years past the eye shadow experience and we are now into 1989.  My memory is a little cloudy about this time but it would have been around this time that I had at least moved from make up to trying on some of my mothers clothes.  It would not have been a large window as I I grew quite fast and in not time was well bigger that my mother.

It was also around this time that I was able to catch shows like Donahue on TV where he had Crossdressers on the show.  I was finally able to have a word to refer to what I was.

There were various other shows at the time that had Crossdressers on them like Sally Jesse Raphael and Joan Rivers.

There were a quite a few events that made me think twice about ever telling anyone about my little secret.  First was a episode of one of the above mentioned shows that really put Crossdressers into a bad light,  the details of which I can’t remember or find a clip for.  It was played out that Crossdressers were deviants who ruined marriages by keeping this terrible secret,  borrowing their wives clothes and generally being perceived as sexual freaks.  To my 15 year old mind this was the end of all things,  how could I ever be happy in life knowing that I would never be able to find any happiness and that if I ever did it would surely fall to pieces if she ever found out.

Another event was in late stages of grade 8.  There was a play going on in school and one of the other boys somehow ended up playing a part as a girl which involved him wearing a dress and make up.  To me this seemed like a perfect thing to do but the whole time the dress rehearsals were going on he was relentlessly by the other boys.  Even though he was not dressing up by choice he was still getting made fun of.  I could only imagine what it would be like if someone ever found out that I dressed up of my own accord.

And the third and final thing I remember about this ear was I had a friend over one Friday afternoon after school and one of the aforementioned shows was on TV with either Crossdressers or Drag Queens.  Back in the day we only had a TV antenna and no cable so we were limited to about 2 stations on a good day.  So seeing as this was really the only thing on I was going to watch it.  I will always remember my friend freaking out about getting sick from watching men in woman’s clothes.  He put up such a fuss about how seeing a man in a dress made him sick to his stomach that I just shut off the TV and tried to find something else to do.  Needless to say that weekend was not much fun at all after hearing your friend tell you that a man in a dress makes him physically ill.

This year was kind of the ending to childhood as after this I would be moving into as I recall some of the worst years in my life.  High School.


Proof I have a great wife


A Little back story was that the daughter was at home at the time and the most that I can get away with is a little bit of underdressing as my heavy pants and sweaters will hide any underwear from view.

The wife stated we need a sign for the door so she knows when I am doing “Girly things”.  Maybe I should just lock it next time.



A Change in Attitude


Things change,  that is a given in life.  But some things I never intended to change seem to have.

For as long as I can remember I have always said I would never go out dressed.  Firstly the city I live in is very small and there is always a chance you could run into someone you know and secondly I am not really big on going out at all,  some would even say I am anti-social.  It’s not so much that I don’t like hanging out with people it’s just that I am very uncomfortable around people I don’t know.

That bring us to this week at having a conversation with t a friend that knows about Cynthia.  I had asked her if she could crochet me a set of breast forms but she up until this point was unable to get the proper type of material.  She informed me she had found it and was going to be starting them as soon as she has the time.  We got into a discussion of different types of forms and how they move and how they look,   she commented how it really did not matter how mine moved due to me never going out.  I agreed and we talked a little more before I had to go.

Later on I was thinking about how I had answered this question and was not sure at this point if I had given the correct answer.  I seem to have gained a small nagging feeling that at some point I should go out at least once just to be able to say I have done this.  Now for me to go out and pass is not a option seeing that before heels I am already almost 6′ tall and more than average weight (A lady never tells).  I think this change has been coming slowly for a little while now.  In the last couple of years I have lost some of the fear of going into stores and purchasing some stuff for myself like razors, shaving gel and pantyhose,  but that’s still all stuff I can pass on as picking up for the wife.  I have also been able to go out Underdressed on quite a few occasions in the last few months and have talked to a local make up artist to get a possible appointment to have my foundation matched.

I did mention to my friend the next day about how her statement made me question my long held belief that I would never be going out.  Her advice was to pick a larger city and maybe make it on a pride weekend festivities and as she stated be in a secure place “While you get your freak on”.  She is so awesome.


First shopping trip of 2016



Well we still have some Boxing week sales going on and I can’t pass up on the good deals. The wife and I had made plans to head on over to Addition Elle earlier in the week but things got so busy it was hard to find time. I decided that I could make the trip on my own and pick up some of the stuff I wanted before the sale goes away.

After searching the Addition elle website I had made my list and had all the sizes and product numbers so it would be easier for the ladies in the store to search. I really had my heart set on this Marled Yarn Long Sleeved Dress


The website product search said it was available in store but alas when I got there it had been sold earlier in the day.  Although I was a little heartbroken I felt a little better when the lady pulled out this Michel Studio Rib Knit Dress


Not really the style I wanted but one I had short listed before.  I figured a nice new pair of tights would finish the look off very well and picked a more festive pair of Metallic Glitter Tights.additionelle_315385_1_0

Unfortunately they were also out of stock so I figured I would just get a pair of panty hose from Walmart later on.

Lastly I decided that seeing that this was my Christmas money I was going to get something else.  I scanned the lingerie section of the website and came across this bra.  The Lace And Rhinestone Femme Couture Bra Deesse Collection.  I had purchased a similar one in black awhile back and I just loved this colour.additionelle_742093_71_0

And of course I had to get the matching High Cut Lace And Rhinestone Trim Panty Deesse Collection.  There was a boy short version but I really prefer these ones.additionelle_742062_71_0


So that was my first trip out for 2016.  Hopefully I can get some pics of me in the dress and a review of it up soon.

Thanks for reading