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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