With thanks to Cynthia for kindly giving permission to publicly answer her questions from 100 Questions Someone might ask a Crossdresser, here’s my responses to those very same questions – on this occasion, from 1-50.  Well, it had to be done – didn’t it?

1. How old were you when you realised you were different?
2. How old were you when you first tried wearing women’s clothes, make up etc?
I don’t think I realised I was different.  As I remember, trying on some of what I recall as being my mum’s clothes was done as I was growing up.  I can’t really remember where I was address-wise (as that would help come up with an age) as we moved house a bit and I’ve got no memories of where I did it – just that I did, but whilst I certainly tried it the odd few times, it didn’t last more than a minute or so as I quickly determind that I didn’t like it and I don’t recall anything else happening afterwards either.

3. Have you ever told anyone you were a Crossdresser? If yes who?
The only people who have ever known are equally anonymous folk on line.

4. At what age did you come up with your femme name?
Probably within the last five or so years when I started going on-line with my crossdressing on display.

5. Did you use any other femme names before you chose your current name? If so what was it?
No – nothing before nor inclination or motivation to come up with one.

6. How did you come up with your Femme name?
That’s one I’ve never publicly answered until now, but it’s a simple one.  Take the word ‘Lingerie’, swap it round and make it look more like a name and you get Gerry Lynn.  I think it’s more of a double barrelled forename than a male forename and female surname.  I’ve never considered it being Geraldine though – just Gerry-Lynn.  I suppose it’s like ‘Sarah-Louise’ or something similar.

7. Have you ever been caught dressed?
Yes, but nowhere near fully dressed up in lingerie – it was very much practically naked as I was in a panicked state of undress with the outfit I was wearing thrown in the bottom of a cupboard. As I recall, I think I was only in stockings.

8. How did the people you told take it? 
Very badly indeed – the worst experience ever I think – I am nevertheless here to *not* tell the tale and nor will I ever – that is to remain an impenetrable guarded secret.  Although the experience made me stop for quite a time, I am somewhat shocked that I started (but subsequently stopped) again!  That was very very risky.

9. Are you married?   Yes.

10. Does your spouse know? and if so are they accepting? No – she does not know and although generally accepting of others (I know that from conversation), it is not something she would have expected from me nor would suspect.

11. What was the first article of women’s clothes you ever bought?  I used to buy a lot of lingerie outfits on-line and have them delivered. I’ve only rarely actually bought something from a lingerie store, sometimes off the back of it being for the wife. I’ve purged quite a lot, and because of the reasons for the purge, my memory is largely a blank as to what was first.  I do remember some very nice cami-suspenders I’ve documented about on the blog before.  A Red Gingham outfit and a white silky ruffled fronted cami-suspender with glittery front for example – they were lovely. 😦

12. What was the last article of women’s clothes you bought?  Other than a pair of lacy top black hold up stockings on a frequent basis, a very tight fitting pink lace cami-suspender with thick pink straps – I think that was March-April last year.

13. Long or short skirts?  Neither. Over garments are not/have not been for me. Lingerie only!

14. Do you venture out dressed? If yes how often do you go out dressed?  I would quite frequently go out places with stockings and suspenders and a g-string on underneath male attire.  Back in the day, I’d also wear a bra but with layers on over the top to avoid detection and for the main, it was one of the wife’s old trainer bras that had no cup!   99% of the time, it has been from the waist down.

Sometimes I’d do it for days upon end, then I wouldn’t for a while.  Going out places includes only those places I’d go, never with family, work for example and sometimes even hobbies.

15. If you could go back and change one thing about your Crossdressing what would it be?  I wish I’d not purged so many glorious outfits and items.  Goodness only knows how much I spent on items I then simply threw away.  However, the reason to purge seemed more than right at the time.

16. Do you feel being a Crossdresser makes you a better person? If yes how so?  Crossdressing was certainly fulfilling and somehow contented me in some ways.  Did it make me a better person per se?  I don’t think it changed me as a person other than I was selfish with it.  Ultimately, nothing and no-one else mattered whilst I used practically every single moment to crossdress.

17. How long were you dating / married before you told your significant other or spouse?  See 10. above.

18. What is your favourite article of clothing? I’ve always had a thing about stockings and suspenders. Everything else followed from there.

19. If you have bought your own clothes,  have you ever had any issues with store clerks?  Never had a issue as I tell the staff that it is for my wife.  I have bought some stuff for her and her stuff has fitted me fine.  Some of the stuff I’ve bought has been purchased ‘for my wife’ but solely for me.  My wife is not into stockings and suspenders nor anything other than day-to-day bra and pants.

20. What is your greatest Crossdressing accomplishment? Probably getting nice compliments and attention for the way I dressed and how co-ordinated it was.  Getting attention from women was a particularly massive turn on. I loved it on the rare occasion a woman came viewing my web cam.  So exciting!

21. What is your favourite brand of make up? 
22. Do you wear perfume? If yes what is your favourite fragrance? 
23. How many lipsticks do you own?  None
24. What is your favourite colour of lipstick called?
Make up and perfume isn’t for me.

25. Did you buy breast forms or do you make your own?  I’ve often browsed breast forms on line but always veered away from purchasing as it just somehow felt ‘a step too far’.  I have though dabbled with water filled pink balloons which was comedic prep-wise (!) but quite sensuous when done (providing I could content myself with the way they sat in outfits).

26. Do you ever have dreams related to Crossdressing? If yes what was it?  It is not really something you can stop is it, but yes, it has happened.  Sometimes it was obviously part of the moment, other times it was as a sub-plot.  I can’t really remember details but as with a lot of dreams, the circumstances and virtual realities of dreams were unreal and bizarre but made me think for a moment after I woke for as long as I could remember!

27. When not dressed how often do you think about it,  for example while at work?  Subject-wise, every day, but usually nothing too prolonged or specific.  Nowadays, frequently just reminders.

28. Favourite hair removal method?  A full body wax.

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 and in a fantasy world, two women.

30. Do you have space in the closet for your clothes or do you have to hide them?  When I did have them, they were hidden under lock and key.

31. Have you ever purged your clothes?  Frequently!

32. Given the opportunity would you take a job where you could work as either your male or female self at any time?  No – never.

33. Do you paint your natural finger nails or use fake ones?  No.
34. What Colour do you like to use on your finger nails?  Purples or pinks? See above.
35. Do you keep your toe nails painted?  No.
36. What colour nail polish do you like best on your toes?  See above.

37. If you wear make up what part do you find the hardest to learn how to do?  I don’t wear and have never worn nor have been motivated to wear make up.

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?  Bridal lingerie, yes.  Wedding Dress, no.

41. Do you own a wig or use your own hair?  I wore a wig at work for a laugh once and camped it up around the office, but that wasn’t a motivator to start wearing one.

42. How often are you able to dress up during the week?  Nowadays, I don’t but it could be virtually most of the week at one time – at any and every possible moment.

43. How many Blouses do you own?  None
44. How many Skirts do you own?  None
45. How many Dresses do you own?  None
46. How many bras do you own?  None
47. How many pairs of panties do you own? None.
48. What is your favourite colour for lingerie?  White.
49. Pantyhose or Thigh Highs?  Tights (as we call them here), don’t do it and have never done it for me.  Give me stockings (hold ups were usually the norm) anytime.

50. Favourite place to shop for miscellaneous items?  Wilkinsons for lace top hold-up stockings.

There you go – I await Cynthia‘s 51-100 listing with great excitement…