Thing’s I have learned being a Crossdresser: 4 Years Later

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One of my most read blog post’s of all time is Things I have learned being a Crossdresser and as of August 2017 it has reached 1000 views.  I figured seeing as it has reached 1000 a update to the blog with the other things I have learned and where I am today was in order.  I have the original text in black and my new updates in pink.

I have learned so many things in my time as a Cross Dresser.   Dressing up like a woman takes so much skill and patience I am amazed women go through this every day.

1) Clothes

This is the first minefield you should try and cross,  and let me tell you it’s a big one.   Shopping for Men’s clothes is pretty simple as a whole.  Pants, shirt, underwear and socks.  Choose from some of your basic colors like brown, green or blue and you are set.  Women’s clothes on the other hand is a multitude  of colors and fabrics all of which make a completely different look  and statement when worn in the daytime or  night.  I have spent many many hours on the internet looking at clothes and I seem to only have touched the surface of what is out there.

I have expanded my wardrobe over the last 4 years with lots of new stuff that I never thought I would have worn before.  From long dresses, shorter skirts and sheer lace tops.  I was lucky enough to get a female friend that was very helpful in the fashion department.  I would regularly send her pictures of something I wanted to buy and get her opinions of what should or could be matched with the said item.   My best idea now is just to buy stuff that I like and think will be fun to wear.

We also cannot forget the base to any good outfit, The Lingerie.  My Lingerie drawer has expanded with my wardrobe to incorporate many more pieces.  Sometimes you will want to wear a top that has a low collar and you need a lower cut bra that cannot be seen in the collar of the top.

2) Skin care and Make up

Again, another minefield.  I feel that cosmetics as a whole is one of the most confusing things to learn as a Cross Dresser,  clothes can be figured out but to truly learn how to pick the colors that suit you and learn to apply said colors really takes practice.  Make up sections in most stores are fairly big,  at least 4 to 5 isles.  This is where will usually find,  make up,  nail polish and supplies, fragrance and various other beauty tools (brushes, sponges, etc).  I remember the first time I went to purchase some make up with my wife.  I was so nervous the whole time I just pointed at some stuff and did not really pay attention as to what colours I was getting.  Well after my first attempt at using said colours I looked like a clown and not even a funny clown,  more like a horror movie clown.  There are lots of website that give hints and tips for finding the right matches for your skin tone and skin type.  Another good option would be to consult your local stores or salons to see if they are CD friendly and have some help learning.  Most places will give lessons if you buy a specific amount of product.

I wish I would have not used the term “Minefield” once let alone twice,  Oh well.  You live and learn.

I would  like to say that I was awesome at applying my make up,  But I am only slightly better than I was four years ago.  It’s hard to to practise on make up when it’s such a time consuming thing to work on.  There is the shaving,  moisturising and so on and so forth.  I like to have at least a good 2 to 3 hours for a make up practise session because I know at least 3 times I will have to start all over again.

I am still trying to find the right shade of foundation without any luck.  I have spent more on foundation than any other make up product.  I am currently looking into getting a appointment the local MAC store to get matched.  Apparently the store here has a good reputation from the local community but they do not have a private room so I would have my appointment right out in the front of the store,  I am sure I am not ready for that yet.

I have given up on trying to only find “The Right Colours” for me.  Instead I buy whatever colours I want to try and have fun with.  My lipstick and eye colour choices have not gone extreme in any way but I am for sure going for brighter red and pinks and so far they look pretty good.  As far as skin care I am still pretty relaxed about it only paying attention to my skin just before I get ready to apply my make up.

3) Shaving your legs

I am positive every woman is a contortionist with a perfect sense of balance and eyes like a hawk.  I can’t seem to shave my legs without missing a huge area of hair,  not being able to see some areas at all or almost falling over and killing myself.    My wife was nice enough to teach me how to shave my legs years ago.  I say shave but the first time was more like clearing a forest,  and I ran out of hot water in the shower TWICE,  it was well over a hour experience.  Now I only shave in the winter months which is when Cynthia wants to come out more and the fact that I don’t want to tell people why I shave my legs.  I know most people will not believe I am a Olympic swimmer or cyclist.

Practise makes better,  But I am still not perfect.  Once the weather turns cold in early fall I start shaving my legs and that first trim is the hardest part in my opinion and takes the longest amount of time.  It really helps to have a well lit shower and at least the edge of the tub to prop your foot up on.  Remember to use lots of shave gel and a decent razor.  I find it’s best to completely wash and get your hair done,  That way your leg hair will be softer from the hot water and easier to cut.  I get quite a few shaves from my current razor and I am usually shaving my legs at least every 2 to 3 days otherwise I end up with tons of little ingrown hairs..  If you have really coarse leg hair you may need to change your blades more often to prevent razor burn and ingrown hairs.

Since I posted this I also have started shaving my chest in the winter months as well.  There is nothing worse than having a nice lower cut top and passing a mirror and seeing all those chest hairs poking out from a really nice top.  I tried little straps that attached to a bra that would mimic the top of a cami,  they are OK but just not the look I wanted to go for.  So for the first time last winter I shaved my chest and tried to make some cleavage.  Did not go as well as some things I found on the internet but at least it looked better.  The chest area does get super itchy when the little hairs grow back in,  it almost drove me crazy.

4) Your Significant Other

If you are as lucky as me to have a wife or girlfriend who can accept your feminine side you are in a good place.  Also you are in a place to loose many things.  I cannot count how much stuff I have lost to my wife over the years.  Everything from make up to blouses.  Seems she uses it once and it ends up in her regular rotation.

I am so lucky that my Wife puts up with me even after all these years.  I know at times I was very annoying when it came to either talking about dressing or wanting her to take me shopping that I am sure at times she wished the Crossdressing would just go away.  I think I have mellowed over the years and now that I can go out and just buy my own stuff makes it a lot easier on her,  although she does still like a good shopping spree every now and then.

5) Nail Polish

Looks easy doesn’t it?  That is until you try it for yourself.  When you watch a video on Youtube the brush strokes seem oh so easy until you try to replicate it and you end up using more nail polish remover than nail polish.   Similar to make up,  Nail polish requires time to learn how to do it properly.

I gave up on painting my own natural finger nails,  way to much work only to have to take it off either that night or the next morning.  I could never get good with painting my right hand nails with my left hand.  I went and bought large sized acrylic nails and made myself quite a few sets.  The great thing with the fake nails and tip stickers it that the nails can be removed and used over and over again.  It’s also a way easier way to experiment with nail ideas.  The fake nails are fairly easy to cut and shape in any way you want then paint and with the price they will not break the bank doing so.  I did a kinda tutorial that you can read here.

I have learned how to paint my toenails decently well and I tend to keep them painted from fall right back into spring.  I use Nina Ultra Pro nail polish from Sally beauty that has a wider than normal brush.

6) Pantyhose on wet legs

You may as well fight a Polar bear because you have about the same odds at winning that fight as you do getting a pair of pantyhose up damp legs.  It’s damn near impossible to pull them up and at the same time you have to be super careful not to put a run in them or all your hard work just went down the drain.  Take a hint from me wait till you are totally dry or invest in thigh highs.

Still can’t get pantyhose on wet legs,  But I did get pantyhose on with my fake nails already done and didn’t put a run in them so that’s a WIN.

Well that’s all I can think of for now,  I am sure  I will think up some more.

And for those of you that do read my blog till the end I appreciate that you can make it through basically what amounts to ranting on for what seem like forever.

So that’s my 4 years later update.  I got some wins and some things that I still need to work on.  Crossdressing is ever evolving.

Thanks

Cynthia

 

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New stuff coming

Hello lovely readers,  How is everyone doing?

Just a small post to let you all know I have some new stuff coming down the line soon.  I was feeling a little burnt out from the 100 Questions someone might ask a Crossdresser,  I checked the creation date of the original file and I had started it way back in February 2016.

Hopefully you are not bored of lists yet because I have one more left to post and that will be it for awhile.  While checking the stats for my blog I keep seeing that the most used search term for people finding my blog is

  • crossdressed lingerie blog
  • crossdress full up lingerie start
  • crossdressing lingerie crossdressing lingerie
  • crossdressers in lingerie blog
  • lingerie crossdressing lingerie crossdressing
  • cross dressing lingerie
  • ingerie crossdressed blogs

Although I may not be giving these people what they want I will be reviewing some of the lingerie I have purchased over the years and we will see how it goes and if I continue after the first few.

So that’s it for now,  I hope you all have a good weekend and hope to see you back here soon.

Thanks

Cynthia

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

One of those rare Occasions

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So my daughter is away for the night which means that Cynthia gets to come out and party.  And by party and mean sit on the couch and watch TV.

It was a pretty slow day at work so I was not really tired which meant I at least had the energy to get ready.  The wife and I headed to the mall to get something to watch for the night and we picked up season 3 of a show we really like.  Bob’s Burgers.  For those of you that are not familiar with it it’s a animated show that revolves around a family’s wacky antics as they try to keep their restaurant open.  After the mall we went and grabbed some supper from a sub shop and headed home.  After supper I hopped in the shower and got cleaned up and proceeded to put on my underwear and slip in my forms.  Tonight I was finally able to wear the dress I had purchased back in  January that I wrote about here.  I didn’t go crazy with the make up,  just put on some lipstick for some colour.

The rest of the night was spent with the wife sitting in front of the TV just having a good laugh.  Sometimes it’s not what you do it’s who you do it with.

I am still working on part 2 of the 100 Questions that someone might ask a Crossdresser and I am down to 3 questions.  As soon as I can complete the last 3 questions I will post up the second part of the list.  If anyone has any ideas for the final 3 questions please email me at cynthia01012 at gmail.com and I will give you credit for the question and I will link back to your blog.  If you want to complete the list yourself I will email me and I will send you a copy of the list.

Thanks for reading

Cynthia

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

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

 

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