Am I a Crossdresser or Transgender, crossdressing services address a common question

Am I a Crossdresser or Transgender

Posted April 4, 2020 by Kristina

A few years ago (and don’t ask ‘how many’ ladies – a girl never reveals her age) when I was at school, I remember oh so well the admiring glances of a young man. We were both seventeen. Chris was kind of cute, but not exactly my type.


Once I found that he was following me down the road and I just felt his eyes upon me. So I turned and asked him, ever so politely of course, why he was following me. His face became beetroot red and he became quite flustered. He stumbled out a few incoherent phrases; and saying that he wasn’t really following me (oh the put-down: so it wasn’t me who was being admired but my clothes!) but then he really confused me by saying he simply loved my clothes, my shoes and my bag. So I walked on leaving him to stew in his beetroot juices.

Am I a crossdresser or transgender? Chloe has asked herself this question many times before and is still unsure of the answer, one thing she does know is she ia trans fluid.

A couple of week later, I saw Chris in the public library – but he did not see me. Now this was in the days before the Internet and Wikipedia. Not so very long ago, of course. He was riveted on a book and reading it intensely. After a while he popped it back on the shelf and left. I went over and pulled the book down. It fell open at a page which astonished me. The chapter he had been reading was about transvestites. The penny, or rather a huge pile of pennies, dropped.

Today Chris would have probably been asking the question: am I a crossdresser or transgender? Or even trans fluid? But back then the only term we knew was transvestite. But it was very clear that this cute young man wanted to know the answer to that question: am I a crossdresser or transgender? So, on the spur of the moment I decided I was going to help him find out.

A few days later, without letting on that I had seen him at the library when he was pouring over his dilemma: am I a crossdresser or transgender, I asked him whether he would like to come round to my house: I said I had been thinking of what he had said to me and had a new dress and shoes about which I would like his opinion. His eyes almost popped out of his head. But I already knew that the allure of my ‘am I a crossdresser or transgender’ wardrobe had him hooked.

Seize the time was always my motto. And we marched off to my house: my parents were away and so I knew we had time and world enough to ourselves to resolve his question: am I a transvestite or in more modern terms in this universe of internet and Wikipedia am I a crossdresser or transgender? We were about to find out. I had ‘sized’ Chris up and knew that he would fit comfortably into my dresses..

Am I a crossdresser is another question that Chloe asks herself but all Chloe really wants to be is herself.

I installed him in the front room and slipped upstairs to put my party dress and new shoes on; and underneath my very best bra and panties. Tights with a subtle sheen. And then I went downstairs for his ‘am I a crossdresser or transgender’ fashion parade.

This time his eyes really did stand out on stalks: and I knew at once that his innermost question, ‘am I a crossdresser or transgender?’, was absolutely spot on. I did a few twirls and he told me that I looked amazing, which of course I did! I let him feel the silken fabric: he was on my hook and I was drawing him in carefully to his ‘am I a crossdresser or transgender?’ moment. He wasn’t going to wriggle free from Charlotte’s web, if you will forgive my mixed metaphors.

Then I popped the ‘am I a crossdresser or transgender’ question: would he like to try them on: just for fun of course. After a hesitation of microseconds, he said yes. So we went upstairs and, having changed into less appealing but still chic daytime wear, we started his am I a crossdresser or transgender transformation. I told him that without the proper lingerie the effect would not be right. So, once after a momentary embarrassment he undressed and, garment by garment, I helped to change him from male to female, from boy to girl. I even remembered my mother’s collection of wigs from way back when: the crowning glory to the am I a crossdresser or transgender ensemble.

His make-up may have been a little inexpertly applied, but then I never did have Kays skills in that department. Even so, Chris looked fabulous as we found the essential answer to his question: am I a crossdresser or transgender? He stood transfixed in front of the mirror, as so many of Kays girls have done, perhaps with that same question in mind: am I a crossdresser or transgender?

Chloe is a young lady that does not really want a label, even though she may ask herself, am I transgender?

That was the first of many of his visits to my wardrobe: all very innocent stuff: girlfriends together, exploring and answering over and over again his question am I a crossdresser or transgender? Such fun!

Such wonderful ‘am I a crossdresser or transgender?’ fun. In fact, then as now the answer is simple: Chris was and is (I still keep in touch with her): she has stopped asking: am I a crossdresser or transgender? She is both a crossdresser and transgender. The label is unimportant for her. The feminine feelings inside are what count. So when the question is posed: ‘am I a crossdresser of transgender?’ she smiles sweetly and says: “C’est ma vie!”

So many girls get hung up on how to describe themselves, puzzled by such questions as am I a crossdresser or transgender? Certainly some terms do define a girl more often than not in fairly clear ways: she-males just love having real (if enhanced) boobs as well as their male bits and bobs; but transsexuals want to say a not so fond farewell to all that external baggage. But for transvestites, T-girls, transgender, crossdressers it’s a different story: “What’s in a name? That which we call a rose by any other word would smell as sweet.”

And, dear girlfriends, we are all like Juliet – the sweetest roses. So when that question comes to mine: am I a crossdresser or transgender? There is only one answer: you are what you are and who you are and how you live; and you should love every delicious ‘am I a crossdresser or transgender?’ moment. For as JJ says: you only live once.

Kay xx