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.

If you enjoy this and want to do it yourself please send me a email to cynthia01012 at gmail.com and I can send you a copy of a blank list.  You just  have to put a link back to mine and give the appropriate credit.

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.

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.

Thanks for reading.

Cynthia

A Change in Attitude

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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.

Cynthia

Wifey’s point of view

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I had  a surprise today,  My wife told me she had written something and wanted me to post if on here on her behalf.  So here it is.


Cynthia and I have been together forever,  Okay well 20 years.  When Cynthia was firs trying to tell me she would not come right out and tell me what was going on, just she had something big to tell me. She said she was going to spell it out, and goes it starts with a C well I almost started crying because I thought she was going to tell me it was Cancer.  Why it never really bothered me was I believe people are born who they are in some regards and sometimes people can be born with 2 souls a male and a female, both parts are fine because that person has a gift.

To a degree they can live and understand both worlds. I also had a fair number of different people I knew some gay, straight, punk, hippies etc it sounds cliche but I figured as long as you were not hurting another soul, human, animal or otherwise be who you are.

The other reason that I know Cynthia does not talk about is how she has always been supportive of me. When I met Cynthia she was the first man who was ever nice to me, the first man to not lay a finger on me in any way. She accepted my scars, and accepted and understood I had mental health issues because of having a long trauma history. Cynthia has been my rock, my only consent, know matter what. I have been in and out of hospitals so much I lost count. Even when we got married I asked her if she was sure, that I would completely understand if she wanted to back out. She still said I do! She has gone to appointments with me, sat with me well I cried, stayed away when I couldn’t stand to be touched. And still kept coming home.

The major stress she has previously talked about several years ago was when I attempted suicide. She still kept coming back. Took care of everything my dog, our daughter my bills etc, and still managed to come visit me often. I was in over Christmas and she made it magical for our daughter. I have recently finally been able to get begin proper trauma therapy and help I am not better by any means, but working my way their.

From the beginning Cynthia saw past my out there exterior, and my sometimes tough exterior, and saw me. Some how was able to love me and know that I was a good person, not just a mental case.

I understood her fear of Stigma, as she understood or tried to understand me. When I was pregnant I was so scared I would not be a good Mother.  Cynthia never had a doubt about me. I feel like she has talked about how great I am to go shopping with, or understanding, but she will never pat her self on the back for the kind of person she is.

We fight, we cry and don’t see eye to eye, but we also laugh and joke with each other and at each other.

My only hope is that to the SO’s of Crossdressers is to understand this is who they are, like they have accepted you for who you are (Hopefully and if not and you can not accept each other that is not a healthy place to be). When they tell you they are showing you a piece of their soul, and that is tough for anyone. They are being completely vulnerable with you, knowing that the information they just gave you could so bite them in the arse. They trust you and that is why they are telling you. If they didn’t tell you at the beginning it is not because they are liars or were going to wait until you had been together for a long time. They didn’t know how, they were scared. Cynthia has mentioned how scared she was of what the Crossdressers on tv and in the movies were like and it was not a good portrayal. Give it some time, talk to them, I hope that some how you can meet in the middle.  It’s not as bad as it sounds.

For the Crossdressing ladies out there. When you are in a pink fog, and your SO turns and snaps at you, and decides I don’t want to talk about it any more, It may feel like rejection but its not. It would be just as annoying if the only thing your spouse talked about for days was I don’t know cabbage and how great cabbage was, all the ways you could cook cabbage, all the stores to shop for cabbage, and look at all the pictures of cabbage. You would get annoyed too. Single Crossdressers I can only hope that you are able to find that special someone to share your feminine soul with.

To everyone be yourself, breathe, and hopefully with the internet you will know be able to connect with others in a safe fashion, or find support.

Cynthia give your self more credit. You are pretty great too!


This totally made me feel awesome.  And i love the cabbage analogy,  too funny.

Love you dear.

Cynthia.

A Foot out of the door, of the closet that is.

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Coming out of the closet is not a easy thing to do ever.  Whether it be you are Gay, Trans or Cross Dresser,  letting someone in on your little secret can be a very hard thing to do,  and deciding on who to tell can be even harder.

I have two very different tales of how people found out about my other side for your reading pleasure.

 

My wife

Ahh back in the good old days of 1996 everything seemed great,  I had been with my girlfriend for 6 months at that point and everything seemed to be going pretty good.  Up until this point I had not really thought about telling her about my other side but I knew it was inevitable that the urge to dress would get to a point where I would have to tell her.  You have to remember back in those days I did not have access to the internet and any information I had on Cross Dressing came from daytime TV talk shows which always cast a bad light on act and how it tore family’s apart.  

It took days to finally get up the nerve to let her know that I had something important to tell her.  I was not even able to tell her out loud that I was a Cross Dresser so I spent most of the morning trying to spell it out to her.  It took most of the morning but when she finally put all the pieces together I could not have asked for a better response.   I can’t say she was ecstatic with the idea but she seemed to already have a sense that there was something different about me and rolled with the punches. 

Although after that it was months of me badgering her for stuff,  in hind sight not the greatest idea but I have learned some moderation from my prior mistakes.

My Co-worker

This one is more of a mistake,  but a mistake in a good way.  This all happened about a year ago.  Me and my co-worker have a great relationship as far as work goes,  She has let me spill my guts on more that one occasion about the troubles that are going on in my life and has always listened to me.  We were joking one day about shoes for some reason and she mentioned something about high heeled shoes and I made some sort of crack,  She replied that she did not know me that well and it was left at that,  just a joke.

Weeks later my world seemed to be falling apart due to some problems going on in my life and I was stressed out to the max at that point.  She had asked how I was dealing with my stress and I responded that I was playing a lot of video games and some other weird things that would freak her out.  Her exact words were “Oh Honey, there is nothing you could tell me that would freak me out”.  I blurted out “Remember the joke a couple of weeks ago about the high heels?,  Well I do own a pair and can walk in them quite well.  

It was really out of my mouth before I even knew what I was saying and I just froze like a deer in the headlights.  Her exact response eludes me now but it was something like “okay”.  That was pretty much the end of the conversation although it has been brought back up from time to time in passing.

So those are my two experiences in coming out.  Hope you enjoyed my ramblings.

Cynthia