20 Questions With A Crossdresser

Time for 20 Questions With A Crossdresser again...where I play a little game of Q & A with one of my gal pals and ask some questions we all may be curious about, and some silly ones too. Somewhere inside though we all can find something we can relate to. This time I hung with a local New York girl who is the hostess with the mostess, who bubbles with personality and always makes me smile with a wise crack. So lets get to it and play 20 Questions..

1. What is your name?

Melissa Hyland

2. What made you decide on that female name, Why did you choose it?

I am not certain. I just kept narrowing down names that I thought sounded good with my real last name then I realized it was not a good idea and changed the last name to that of a character in a book who I really liked and presto, a name is born :-)

3. What do you consider yourself ? A cd ( crossdresser) or Tg ( transgender) etc..

I consider myself closer to transsexual than a crossdresser but I am not a textbook case of either from what I can tell. It is all still confusing to me even after all this time.

4. When did you start dressing? How old were you? 

I guess I was 3 or 4 years old when it was introduced to me.

5.Why did you start dressing? 

I did not decide to do it on my own. I had three older sisters who introduced it to me by making me go out on Halloween dressed in some girl outfit they came up with. Then it was used as a threat if I was bad or if they were bored or mad at my father. By like age 9 the behavior was fused solidly to my sexuality and remains that way to this day. I did not discover it on my own, like most people I hear about.

6. What's the first article of clothing you tried on? Why? 

Of my own accord, it was a white frilly communion panty that went with a short white dress of one of my sister's that was kept with the whole outfit in the top of her closet in a box.

7. Were you ever caught crossdressing? 

Yes, twice. Once by my mother at like age 11 and she gave me the worst beating of my life. The kind with bruises and welts. The second time I think I was like 13 and one of my sister's caught me, in her room with some of her stuff. I was worried she would tell my parents but she just smirked and closed the door. I have never spoken to her about that to this day.

8. What do you consider your sexuality? Straight, gay, BI etc...

Is confused an answer? Certainly not straight nor clearly gay as I understand the terms. I guess we will just go with some close variant of Bi.

9. Are you single? Married? Dating? If so what does your partner think of your dressing? 

I am technically married, on paper anyway. My wife knows. She mostly does not care so long as I can keep family from knowing and it does not impact my income.

10. Does your family know you dress? What do they think ?

I have no children, and nobody beyond my wife in my family knows I dress. There would be no benefit to them or me for them to know.

11.  Do you go out in public ? If so what do you like to do? If not...what do you like to do?

I go out as often as the constraints of life allow. I would say on average of once a week. I like to go out to dinner or bars I have seen to be TG tolerant maybe with a little dancing. I also try to attend a few of the nicer and larger LGBT events in the area and try to represent the T as best I can.

12. Do you care if you pass or not? 

Yes, I care very much. I have gone to great effort and expense to learn proper comportment, voice training, makeup training, fashion, electrolysis and laser treatments for hair removal, Even some low level hormone use.

13. Do you wish to go full time..why or why not

I do but my life will not allow for such a thing. I would have to sever contact with nearly all family and friends from my male life and set up somewhere new. That would be a severe financial blow. I will have to stay part time for at least a few more years.

14. Have you ever tried to quit. Or purged ( threw out all your clothes) before? 

No. I may have wished to a few times but I am not capable of purging. I have a hard time 
throwing out even old and damaged items.

15. How would you describe your style.

I would use the words conservative, sophisticated and sexy to describe my style. 

16. How Many pairs of shoes do you own

I own at last count 43 pairs of woman's shoes if you count boots and such.

17. Panties or thong ? 

Panties. I don't even own a thong.

18.  Who are some of your favorite female or cd/trans role models. Why?

I don't know that I consciously have any. Certainly not any cd/trans role models. I may subconsciously admire a female celebrity for there style sense here and there and incorporate bits and pieces of their style sense into my own but I honestly could not tell you who. 

19. If you were stuck on a desert island...what 3 girly things would you bring? 

Hmm, a Ralph Lauren dress, a panty, and pantyhose I guess.

20.   Describe why you love crossdressing in one word. 

-- Peace.






Thanks for playing 20 Questions Melissa. 43 pairs of shoes huh? I have GOT to peek in your closet.... looking forward to hanging again next week  xoxo

Photo credit & Makeup done by the ALWAYS lovely Karen from Femme Fever. Be sure to check out her website RIGHT HERE and book your makeovers, get your photos, and all your other crossdressing needs like gaff's, breast forms etc....

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20 Questions With A Crossdresser

Finally !!! Finally...I got our overseas correspondent from the U.K to take time off from moderating the popular crossdressing support website Crossdressers.com to play a game of 20 questions with me . We all know how it goes by now, I ask the questions, and she gives her story, in her own words. So let's play 20 questions...

1. What is your name?

Katey Victoria to my friends…  Katey Victoria Beckham Kensington Winslet III if I’m in a formal mood…  LoL

2. What made you decide on that female name, Why did you choose it?

A lovely girlfriend I worked with some years ago used Katey as a bit of a nickname for me at work – she’d picked it up from colleagues in our Paris office who would mispronounce my real name.  When I was thinking of a feminine version of my name it came immediately to mind – plus there are some classy celebrity Kateys or Kates around…  I like the idea of class by association, if possible.  Victoria is a lovely name too and is the feminine version of my second male name – the longer formal version is a bit of fun (but you know how us Brits are with our pedigrees…) and was evolved by my best CD GF…

3. What do you consider yourself ? A cd ( crossdresser) or Tg ( transgender) etc..

Both CD and TG.  I think there’s a large overlap of the terms although they are very often argued over or disputed.  Not to start a fight here, but I believe crossdressing is more a description of the process and the physical presentation whereas my belief that most crossdressers are transgender (to some degree) is more a description of the motivation.  I honestly don’t get the ‘just a CD’ assertion, other than perhaps purely fetish CDers:  I don’t believe we have a choice in this, as if we were choosing a football team to support or whether we wanted to play golf or go sailing at weekends – something drives us to express the feminine part of ourselves in this way against all our childhood conditioning and societal pressures.  I believe it’s that quirk in our gender makeup that makes us want to do it and feel good about doing it and that makes us TG.  Beyond that I’m beginning to like the term ‘femulator’.  I really do adore women and want to emulate the way they look.

4. When did you start crossdressing? How old were you?

Probably around 5 or 6 years old – my memory is hazy as to the details but I can remember specific events.  It’s a long time back…

5.Why did you start crossdressing?

Ummm…  my memory is hazy…  Oh – I said that… blonde moment…  Why?  Difficult – but I think it was something to do with the way girls were allowed to look and dress.  Even at that age I thought they seemed to have more attractive options open to them – colours, fabrics, styles: I adored girls even then.

6. What's the first article of clothing you tried on? Why?

I still think this is slightly weird myself – in the late 1960s there was a fashion for young girls to wear brightly coloured, fluffy acrylic hats (in the winter, of course).  I used to take a bathroom break in lessons at school and sneak into the cloakroom to try the girls’ hats on…  I know…  inexplicable…  maybe it seemed like long hair to me…?  Still like acrylic fur though…

7. Were you ever caught crossdressing?

Yes – almost disastrously when about 10 years old messing about with a pair of mum’s stockings (I’d moved on from fluffy hats…) – I think this was the start of my sexual period…  I’d clearly become so distracted by the look and feel of this most feminine of items I hadn’t heard her walk right up to my bedroom door and what was my exit of choice?  Why, to dive under my bed, head first, legs (still nylon clad) sticking out…  How stupid could I have been?   I think I got over that with the excuse: “I just wanted to know what it felt like…” and it was never mentioned again.  I’m still highly secretive and paranoid about discovery but early lessons were useful ones.

8. What do you consider your sexuality? Straight, gay, BI etc...

Straight – very dull, I feel.  Somehow the quirk with my gender should affect my sexuality but it doesn’t.

9. Are you single? Married? Dating? If so what does your partner think of your dressing?

Married and secretive – I doubt I will ever reveal.

10. Does your family know you dress? What do they think ?

No – nobody close to me knows this, and I’ve been through all the internal angst of guilt, lies, shame, keeping secrets, withholding truth.  But I feel they have more to potentially lose than gain from this, as do I, and while I can keep these two parts of me compartmentalized, I’ll just have to live with the responsibility.

11.  Do you go out in public ? If so what do you like to do? If not...what do you like to do?

Yes – I do now!  I was completely closeted for decades but I definitely felt the need to socialise this aspect of me.  It’s early days yet in my public development but I know already I enjoy social events: clubs, balls, soireés – opportunities to wiggle my hips and dance!  I love chatting with sisters and GGs about this weird passion of ours over a drink or two, and it will likely be in ‘safe’ events and venues for the foreseeable future.  Eventually I’d like to be able to do more for the community by participating in more events but it’s tough to do this when one is still partially closeted.

12. Do you care if you pass or not?

I don’t believe that many of us pass if under close scrutiny – I don’t believe I would so I think caring too much about what others think or perceive is wasted energy.  I do care about looking the best I can with what nature has gifted me…  with perhaps a little help from Max Factor, Revlon and others! LoL  Even though I’ve primarily only attended venues or events where crossdressers are recognised and accepted, the vanilla world is always there in the hotel or the journey and if I’m able to blend into the surroundings without attracting too many double-takes or stares (It was difficult recently in a bright red ball gown!) I’d be very content.

13. Do you wish to go full time..why or why not

No.  I am quite happy with my male side being the dominant mode.  The last few months have seen a greater exploration of this facet of my persona than ever before and I’m sure I was wondering where this experimentation would lead me.  I didn’t expect it would change me radically and while it has helped me understand a lot more about myself and what I think I can get out of it, going full time was never remotely a possibility.  The only partial exception to that would be in attending a multi-day event where most days would be en femme with an outfit change or two thrown in – but I’m a lazy girl at heart and I expect male me would be making an appearance for breakfast after a day or two

14. Have you ever tried to quit. Or purged ( threw out all your clothes) before? 

Yes, many times.  Before discovering a lot more about the implications of transgenderism and crossdressing in the past couple of years I would regularly undertake purges during periods of feeling intense guilt and shame at wanting and needing to do something that society broadly views as at best, an aberration and at worst, a perversion.  I’m quite sure that now I’ve cleared a major hurdle of self-acceptance, purges as such, are a thing of the past.  Now I only have to contend with pruning of a wardrobe that once featured some very questionable fashion elements!

15. How would you describe your style.

That’s tricky as it’s evolved quite a lot over the past year – particularly in the revolution from closet to real world.  It’s really hard to describe – on one side I like casual glam as I like to think I was for my first outing, at the other extreme I’m up for complete OTT ballroom glamour (or as much as I can carry that look) but I also like a formal business look too.  I think you can do a lot with well-tailored clothing lifted with some appropriate accessories – I just wish I knew how to do that better!  I think I’m trying for a middle-aged, sexy chic, but that’s probably mostly in my mind.

16. How Many pairs of shoes do you own ? 

Fourteen pairs of shoes and five pairs of boots…  why does that matter so much?  Oh… yes – that’s more than guy shoes – but how many guys need party shoes?

17. Panties or thong ?

Panties – but actually prefer French knickers…

18.  Who are some of your favorite female or cd/trans role models. Why?

I wouldn’t say that I have female or CD role models as such, but there are some really glamorous and inspirational females around today – as one gets older you do appreciate how much effort it takes to remain looking good naturally compared with younger GGs.  I have incredible respect for women that manage to do this and be professionally respected in a still – largely and unjustly – man’s world.

19. If you were stuck on a desert island...what 3 girly things would you bring?

Nail polish, lippy with sunscreen and a huge, floppy hat.

20.   Describe why you love crossdressing in one word.

Fabulousness!

Thanks for playing 20 questions Katey...Knickers huh?? Thats a FIRST for this blog, you will have to expand on that one day, in the meantime say hello to the Queen for me. Want to read MORE 20 Questions with A Crossdresser ?? Click RIGHT HERE