With thanks once more to Cynthia and her blog 100 Questions someone might ask a Crossdresser: Part 2, here are my answers to her final 50.

51. Favourite place to shop for Make up?  Make up? Nah – that’s not for me.

52. Favourite place to shop for clothes? Mail order or Ann Summers

53. Favourite place to shop for Lingerie?  See 52. above.

54. Best time you can think of spent dressed up?  I think it was when the wife went away for a few days. I must have been wearing lingerie all of the time, during the day and at night and for as long as possible.

55. If you could have the ultimate day out, where would you go?  I have always quite fancied being miles away from home, perhaps on business overnight, but taking myself away somewhere where I could go mad and buy loads of lingerie without anyone spotting me that knows me.

56. Funniest thing that’s ever happened to you while Crossdressing?  Probably pinging suspender belts underneath male attire and having to pop off promptly to re-affix (although it wasn’t funny then). Then there was the time that the gardener came and I was going around the house with blinds and curtains shut in white bra, stockings, suspenders, g-string and heels, vaccuming the kitchen as the gardener came past the (shut) back door (albeit with a frosted window) and dashing off on my heels. I don’t think he saw a thing!

57. Do you have pierced ears or wear clip ons? Neither.

58. Do you wear heels?  Did I wear heels when I was crossdressed in lingerie?  99.9% of the time – yes -isn’t it a must?

59. How long did it take you to learn how to walk in heels?  They weren’t all that high and I could never find ones higher.  I guess the wife doesn’t have any, but either way, I like to think of myself as a natural in heels.

60. How many pairs of heels do you own? None.

61. Name a article of Women’s clothing you can’t live without?  Hmm.when I was crossdressing, lingerie in its entirety but particularly stockings and suspenders.

62. What is one article of Women’s clothes you don’t like?  Anything other than lingerie.

63. Do you sleep in a nightie?  No.  When I did sleep in lingerie, it wasn’t a nightie – it was the full cami-suspender or at worst, bra, stockings and suspenders, and only then when I was home alone, although sometimes, I wore a black babydoll.

64. What type of panties do you like?  Skimpy g-strings.

65. What is your favourite colour for a dress?  On women, that little black dress…

66. When you’re wearing pantyhose, what do you do with your junk?  I’ve never had a thing for pantyhose or ‘tights’ where I come from. What I have (big things come in small packages!), goes in what I wear.

67. What stops you from ‘dressing’ in public?  If I wanted to don some lingerie under my male attire, and go out, I just would – end of.  I always wondered if suspender belts and straps could be seen through jeans or trousers, so for the latter particularly, I’d wear some baggy boxers. Was I ever ‘outed’?  No. Of that I’m quite sure.

68. When did you first know your taste in fashion was different from other boys?  I think my crossdressing went on for so long, I don’t really know but equally so, I never did think my taste was different per se.  I just knew what I liked and that was the most important thing.

69. When did you tell your wife? What was her reaction?  No-one knows.  This is about as inner most a secret as inner most secrets can get.

70. What would you tell your 5 year old self if you could?  You may well experience a few things you perhaps wouldn’t think you’ll experience and it will be an interesting ride!

71. Do you shave your chest and armpits as well as your legs? Shaving?  Been there. Done that.  It doesn’t work.  It’s a regular full body wax for me.

72. Have you ever told anyone and they reacted badly? Other than anonymous others on line, no – see 69.above.

73. What was your most surprising reaction when telling someone?  As above.  Otherwise, when I was on my webcam, it was plainly obvious I was a lingerie crossdresser!

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?  I usually felt disappointment when it was time to take lingerie off until the next time, but there was no scratching going off anywhere.  Just tidying up carefully!

75. How did you feel the first time you ‘dressed’?   A-ma-zing!  Over more recent years, as crossdressing has become less frequent, I have taken great joy in how it felt to be back in the saddle so to speak when it happened.  So sensuous.  Just don’t look at the belly.

76. How did you feel the last time you ‘dressed’? Disgusted with myself to be honest.  I plunged into quite some debauchery as far as I’m concerned.

77. Do you and your wife share clothes? If you consider that I wore what were hers but that she didn’t but she didn’t know about me wearing it – yes!

78. What do you wish everyone understood about why you dress that no one seems to really get? If women can wear shirts and trousers and even men’s boxers and be OK, why is it so socially unacceptable for men to wear lingerie?

79. Do you prefer skirts and dresses or pants?  In the UK, ‘pants’ are undergarments, underwear, so I’ll take off the ‘s’ and add ‘ies’ and say ‘panties’.

80. How do you hide your 5 o’clock shadow?  It’s irrelevant to me as I have never fully crossdressed.

81. If you could go somewhere on the planet where not one soul knew who you were and publicly dress, would you?  It’s an interesting thought…but it’d be a tad cold in lingerie perhaps!

83. What will you tell your children (if you don’t intend to tell them) and they find out accidentally?  Let’s not go there.

84. Why aren’t women who wear menswear considered cross-dressers? My point exactly.  Sexuality is more popularly associated with the female sex.  Blokes just wear clothes really and it’s not all that.  It’s not that they’re not considered crossdressers, it’s more like power dressing in a different kind of way isn’t it?

85. Where the hell do you find shoes to fit?  In my wife’s wardrobe!

86. What is the longest you have ever dressed for?   Almost a full weekend if not the full weekend!

87. Do your bra and panties have to match? Absolutely – at least, they should be the same colour.

88. Do you find there is a big difference between your male and female self? If so how?  I can be naughty in general to be honest.  When I was crossdressed in lingerie, I could be very naughty indeed and very willing and happy to pose in certain ways, do certain things or change outfits etc.

89. Does it matter to you if you “Pass” or not?  I think I always left that to those watching my web-cam.  If they liked what they saw to any degree, then great.  I don’t think I was ever trying to ‘pass’ as such – more, look co-ordinated and tidy.

90. Do you “Pass”? As above.

91.  How long does it take you to get all dressed up? I soon got quite quick at getting everything on to be honest. Probably five minutes maximum.  I never timed it, but instead acknowledged how quickly I could do it.

92. If you had a chance to remove your desire to Crossdress would you take it?  I have removed it at least once before and now again – at least for now, but for all the right reasons.

93. Do you have any female role models and if so who are they?   Not in the sense of crossdressing – no.

94. Do you listen to anything while getting ready? No. I much prefer the peace and quiet – the art and act of dressing was always too special to have the silence interupted by music.

95. What do you hope to accomplish by Crossdressing?   It’s more what ‘did’ I hope to accomplish right now but for the sake of answering – to do it for enjoyment, but in moderation and with control, i.e. ensure other things and people weren’t neglected – but crossdressing was too much of a draw and everything and everyone else paled into insignificance

96. What do you expect crossdressing to teach you about being a woman and the experiences associated with it?  It taught me that wearing lingerie was nice, led me to ask why men didn’t have such nice things to wear, but also helped me to see how the World has perhaps oversexualised women and pushed women to unfairly fit a stereotype portrayed on TV, in film and in newspapers and magazines.

97. Do your personal or political views change as a result of the experiences of crossdressing? No my views are my views no matter whether I am crossdressed or not.

98. Has your views on relationships changed with crossdressing in your life?  Sadly, yes.  Crossdressing took over my life and has done so for a quite of a lot of recent history.  Relationships suffered – well they did as far as I’m concerned and I think things have been better since I stopped.  Whether I can stop once and for all is not something I’m prepared to contemplate anytime soon.

99. What was you best Crossdressing experience? I think it was putting on a new lingerie outfit for the first time. Such excitement!  Especially when I’d just picked up a package from the Post Office and couldn’t get home quick enough to unwrap it and put it on.  The senses, the sights, the smells of fresh material…

100. What was your worst Crossdressing experience?  There are probably two moments of note – the one occasion when I was caught when the wife came back home unexpectedly shortly after I’d finished dressing – I never-the-less remain in the same situation to tell the tale this far but no further as to how that is so.  That is quite a relief all ends up.

Otherwise, I think it was those moments when I suddenly disliked being crossdressed in lingerie and couldn’t get ‘back to normal’ quickly enough, usually when the sexual peak had been experienced or when conscience overpowered urge.

That’s it!

Thanks Cynthia for the opportunity to copy and answer your questions.  I hope they have proved to be an interesting read for everyone.

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