100 Questions someone might ask a Crossdresser: Part 2

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And finally now for part 2.  Like I said back in part one questions 66 to 85 were compiled by a co-worker and she has a no nonsense kind of attitude so her questions  were left just as she sent them too me.  I even bugged Katieinthehall  for some question and she obliged with 94 to 98.

51. Favorite place to shop for Make up?  Shoppers Drug Mart. I try to go when they have decent sales on.
52. Favorite place to shop for clothes? Addition Elle.
53. Favorite place to shop for Lingerie?  Addition Elle.
54. Best time you can think of spent dressed up?  Last year spent the night dressed with the Wife while watching Mrs Browns Boys.
55. If you could have the ultimate day out where would you go? Manicure, Make over and shopping.
56. Funniest thing that’s ever happened to you while Crossdressing? While trying to put on a garter belt I ended up giving myself a Charlie horse in my arm.
57. Do you have pierced ears or wear clip ons? I only have one pierced ear but hopefully some day will get the other done.  I don’t have any other jewellery just yet so it’s ok.
58. Do you wear heels? Yes.
59. How long did it take you to learn how to walk in heels?  Probably a week’s worth of walking in them and falling over every night.
60. How many pairs of heels do you own? 1.
61. Name a article of Women’s clothing you can’t live without? Seeing as I can’t fully dress up regularly I would have to say my underwear.
62. What is one article of Women’s clothes you don’t like? Rompers.
63. Do you sleep in a nightie? Only if my Daughter is away.
64. What type of panties do you like? As most people call them “Granny Panties” but with a little flash of lace and sparkle.
65. What is your Favorite color for a dress? A nice lace purple dress would be great.
66. When you’re wearing pantyhose, what do you do with your junk? Let it be free or tuck it up and tape? Seeing as I tend not to wear tight clothes and stay at home I don’t feel the need to tuck.  So if I am wearing panty hose it’s just over some panties.
67. What stops you from ‘dressing’ in public? Fear of yourself or of others? I guess it’s a fear of both.  I am not crazy about being around lots of people and especially while being in a situation where I could be outed.
68. When did you first know your taste in fashion was different from other boys? My earliest recollection would be around the 7 or possible younger.
69. When did you tell your wife? What was her reaction? We had been dating for about 5 months and I figured waiting any longer would maker it harder and a worse situation.  I could not come out and say it so I tried to spell it.  I didn’t even get past “C” and she thought I had Cancer.
70. What would you tell your 5 year old self if you could? You are going to have some tough times but hang on it gets a lot better.
71. Do you shave your chest and armpits as well as your legs? Just the legs.
72. Have you ever told anyone and they reacted badly? No.  I have been pretty lucky I guess.
73. What was your most surprising reaction when telling someone? A Co-worker.  I kinda told her by accident (even though I had thought of telling her before) and with a stone cold face she just said “so”.  She also told me later than everyone deserves to be pretty.
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? Not for me.  It is such a build up to get dressed for me that taking it all off means that for a time it’s over.
75. How did you feel the first time you ‘dressed’? First time truly dressed I felt okay until I glanced in the mirror.  Shock and disgust would be the best way to describe it.
76. How did you feel the last time you ‘dressed’? Great.  No better way to relax after work than to come home slip into a nice blouse and skirt do your make up and watch some tv.
77. Do you and your wife share clothes? We have a few articles that we share.  Mostly blouses and sweaters.
78. What do you wish everyone understood about why you dress that no one seems to really get? I think most people think it’s some sort of fetish and to some people it is and that’s not a issue.  But to the majority of Crossdressers expressing our femininity is just something we feel we need to do.
79. Do you prefer skirts and dresses or pants?  Skirts and dresses mostly.  But I do have a great pair of Jeans I love with some floral embroidery on them.
80. How do you hide your 5 o’clock shadow? Not really a issue for me as I don’t go out but a good shave, some red lipstick and good foundation can work wonders I hear.
81. If you could go somewhere on the planet where not one soul knew who you were and publicly dress, would you? I would have to work my way up to it but I think I could do it.
82. Do you think you’ll ever tell your children? Still debating that.  My daughter is a pretty open thinker.  She already has a understanding of LGBTQ Community.  But I am not sure I ever want her to have to carry around a secret this big.
83. What will you tell your children (if you don’t intend to tell them) and they find out accidentally? I guess at that point Pandora will be out of the box and that Daddy at times like to express a Feminine side.
84. Why aren’t women who wear menswear considered cross-dressers? I never understood that.  I think it’s because men’s clothes is seen as more utilitarian where as Female clothes is seen with more sexuality.  
85. Where the hell do you find shoes to fit? My one and only pair I was able to pick up at a local thrift store.  I keep looking but have never seen size 12’s there again.  I have found on-line stores that do carry sizes well past 12.
86. What is the longest you have ever dressed for? Most would be for a 5 hour stretch.
87. Do your bra and panties have to match? Yes.
88. Do you find there is a big difference between your male and female self? If so how? Although I try to change my mannerisms for the most part my personality is pretty much the same.
89. Does it matter to you if you “Pass” or not? I don’t go out yes so not really.  If I did go out I would want to be as passable as I could get.
90. Do you “Pass”? No.
91.  How long does it take you to get all dressed up? From the time I come home and hop in the shower till I finish my make up and slip into the heels at least a hour and a half maybe longer.  I have never timed it.
92. If you had a chance to remove your desire to Crossdress would you take it? 7 year old me would probably take you up on that offer if only not to feel different.  Adult me knows that in the long run it gets better and I am not hurting anyone doing it so no.
93. Do you have any female role models and if so who are they? Any Woman who is brave enough to stand up and be happy with herself no matter what.
94. Do you listen to anything while getting ready? No,  I tried but then I spend more time trying to pick songs.
95. What do you hope to accomplish by Crossdressing?  For me I don’t think there is anything really to accomplish other than to accept and be happy with myself.
96. What do you expect crossdressing to teach you about being a woman and the experiences associated with it? It has really opened my eyes as to what the Women of today have to put up with.  Being bombarded 24/7 about having to look this way and wear this and how much you should weigh.  Makes you really respect what Women go through.
97. Do your personal or political views change as a result of the experiences of crossdressing? No my views are my views no matter what clothes I am wearing.
98. Has your views on relationships changed with crossdressing in your life?  I was always worried I would never really have a relationship because I was “Different”.  My wife whole heartedly accepted me so I was never really shot down because of it.
99. What was you best Crossdressing experience? Best ever would be the first time that I ever really dressed in front of my wife for a extended time.  I figured her reaction to seeing me dressed would be horrifying but her expression never changed a bit.  I don’t think I was ever more relieved in my life. Second best is when she walked in on me putting on pantyhose and gave me the raised eyebrow and backed out of the room.
100. What was your worst Crossdressing experience?  I don’t think I have had any yet.  I don’t go out so there is not much chance of anyone finding out.  Although last night the cat put a run in my pantyhose so that kinda counts.

So there you have it all 100 questions compiled and answered.  It only took me since the end of January to get it all done.

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

Hope you all enjoyed reading it

Cynthia

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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.

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

Thanks for reading.

Cynthia

Proof I have a great wife

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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.

Cynthia

 

Saturday night’s Alright.

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Well it’s been a couple of months since my last post.  Not really a lot happening here at all.

Last week I found out my daughter was going to a sleep over which means that I could dress and have the run of the house.  The wife and I dropped her off at her party in the afternoon and after headed off to check out some thrift stores.  We did not find anything that caught our eye’s and the store did not have anything grouped by sizes like other thrift stores so you had to go through every article of clothing and check the labels to see if it would fit.

We drove up town to Wal-mart for some stuff and while we were there picked up season one of Mrs. Brown’s Boys.  If you don’t mind crass low brow humour I definitely suggest this show.  It revolves around a family from Ireland with the Matriarch Mrs. Brown being played by as she says it “A man in a Fecking Dress” .

I had Psyched myself up all week for dressing up Saturday night and when the time finally rolled around to start I was getting tired.  I really tried my best but nothing seemed to be going right.  I was not able to get all the stubble off my face no matter which direction I shaved in,  even tried a fresh razor and still terrible.  Shaving my legs was not much better seeing as I nicked my knee.  Moving onto make up I had decided that I was just going to keep it minimal and go with some eye make up and lipstick.  While the wife and I were out I had purchased a eye liner and tried it for the first time.  Again nothing was going my way,  eye liner looked like crap and even my lipstick did not want to co-operate.  I washed my face and just decided to get into my clothes.  I picked a 3/4 sleeve black and white floral pattern blouse, knee length denim skirt and a pair of black thigh high’s.  Nothing that was super fancy but just enough to look good.

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We popped Mrs. Brown’s boys in the DVD player and spent the rest of the night on the couch laughing our asses off.  Not a really exciting night and did not get to do all that I wanted but all in all it was a good night spent with the wife.

Cynthia

Beauty is pain but this is ridiculous.

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A while back I was talking to a friend and she made reference to the underwear she has a only “Utility”,  no thongs, lace, bows or anything fancy.  I had never heard anybody refer to underwear as utility and I pictured something with pockets, heaters, lights and whole other list of useful add ons.  Turns out she may have been right idea to stay away from the fancy stuff,  for you see it’s trying to kill you.  Let me explain.

Like Valerie South had stated in this post on her blog,  the grey times are approaching.  Like Val I mostly dress in the winter seeing as it’s the easiest time to shave legs and paint toe nails.  I decided that I would let Cynthia go on holidays with a bang this year.

It was just luck that my favourite store was having a sale this week and I was able to pick up a new bra

Lace Desire Bra – Déese Collection

Some new Panties

Femme Fatale Full Brief Panty

And something I have never owned before,  A Garter Belt.

femme fatale lace garter

Now seeing as I had never owned a Garter Belt before I was a little unsure of how to put it on but it looked easy enough.  Hook and eye closure in the back with adjustable straps…..Easy.  I was able to get it done up around my waist and the front straps hooked up and adjusted quite easily.  At this point I was feeling pretty good about this purchase.  Now for the back straps.  I had to stop and try to look behind me thinking this would be easier if I could turn my head around backwards.  I was able with some severe twisting to get the left leg strap done up to the thigh highs and then the right.  At this point I can feel a slight tightening in my right arm.  I realized that the back straps were a little too tight so I twist around again to the left and adjust that strap but as I twist around to the right I can feel the muscles in my arm tighten up to the point where I almost had to scream in pain.  I had just somehow given my self a Charlie horse in the arm doing a simple task like putting on some clothes.  It took almost 5 minutes for the tightness and pain to finally subside to the point where I could continue my task and finish getting dressed.

I should have heeded my friends advice and stuck to Utility underwear.

Cynthia