Me?  How old was I?  Old.  Probably 28 or 29, maybe 30.  I was long passed the time when the clothes were an end in themselves; and being Cassie in the world, in public, was the wonderful pleasure.  I had long since decided that I wasn’t a transsexual, but that the occasional woman that was Cassie was quite entirely a woman during those occasions.  But, it wasn’t until then, the first time that she, that is I, was kissed as a woman by a man that I realized how quite entirely that entirely was.

Until that kiss, I considered myself comfortably heterosexual.  I was studiously not homophobic; but I just couldn’t imagine a physical relationship with a man to be of interest.

But then…

He was a trim, good-looking man in jeans and a button-downed shirt, long-sleeved, but with the cuffs turned up a couple of folds, maybe ten years older than me, smart, funny, and sweet from the first words.  He bought me a drink.  I knew he knew from the first, if for no other reason than the club in which we met.

En Femme Style

We wound up that very first night talking for a very long time, alone together at a quiet table.  We got up to dance several times.  But mostly we just talked.

Then, suddenly, towards the end of the evening, during a sweet, slow dance in a shadowy part of the dance floor, it happened.  It was more a nuzzle than a kiss, an extended nuzzle at the place where my neck met my shoulder, right there on the shadowy dance floor.  My reaction surprised me; it was so immediately, completely feminine!  I all but melted into his arms on the dance floor.

It was, by far, the most absolutely female I had ever felt to that moment.

I had felt particularly pretty that night from the time I had left with my friends to go out.  (I think to this day that the dress I was wearing that night will be my favorite of all time.  I have it somewhere still, I think.)

I think, unlike a man, a woman’s sense of her own attractiveness at a given moment is very important to her own sexual response, so I believe that the lucky coincidence of my feeling good about myself and the way I looked that night had a lot to do with my own reaction to this man’s obvious interest in me as a woman, the kind of interest  a man is anticipated to have in a woman, made it seemed only as it should be, only natural.

The real kiss was a little while later that same evening, under the stars, in a little park about a half block from the club.

Being held instead of holding.  Being kissed instead of kissing.

A warm summer evening, in my pretty off-the-shoulder dress and wedge sandals, enveloped in the arms of a man, a man a decade older than me, physically much bigger, gentle but strong, his arms around me, my eyes closed, focusing on the feeling of his soft lips.

The first kiss.  The first kiss.  Is there anything quite like it?  Years later the memory of that kiss lingers still.

  • Have you ever been kissed by a man while dressed as a girl?
  • Where were you when the kiss happened and what did you feel when that first kiss as a girl by a guy happened?
  • If you haven’t been kissed by a guy while dressed as a girl, have you had a fantasy about that romantic event and could you describe it to me?


Thanks for taking the time to read my article and please take a few minutes to either respond to my article or send me an answer to one or more of my questions posted above!

Sincerely, Cassie




More Articles by Cheryl Ann (Cassie) Sanders

View all articles by Cheryl Ann (Cassie) Sanders
The following two tabs change content below.

Cheryl Ann (Cassie) Sanders

Currently sliding from senior citizen into elderly. Dressing for almost 60 years, but rarely in last dozen. Fairly famous TG author, usually under one of two pen names (Alan Barrie or Cheryl Ann "Cassie" Sanders.) Many books in Lee Brewster's classic publishing line, Mardi Gras Press. And a long-time bestseller on Amazon, A WOMAN'S PASSION. (Those sales were eclipsed in recent years by all the $2.99 tg junk writing on Amazon; however, I recently got back the publishing rights and arranged for an inexpensive Kindle Edition and sales have picked right back up.) Also just added a new Kindle Edition of an old nugget to Amazon: THE SUNDAY GAME by Alan Barrie. Although always closeted to my family, I used to travel heavily for business, so had a lot of time to dress. Back in the day, could pass easily even in places like a White House tour or a hotel bar. Have been to a couple of the New England groups first events at Provincetown, but, again, not for a few years.

Latest posts by Cheryl Ann (Cassie) Sanders (see all)

5 4 votes
Article Rating
Inline Feedbacks
View all comments
Lorraine Lowry
Active Member
30 days ago

I’ve never experienced this, and never will at my age, all I can say is WOW!

Jennifer Friendly
Active Member
19 days ago
Reply to  Lorraine Lowry

@Lorraine Lowry Oh Ms Lowry, don’t ever think something is not possible, at any age.  While we can’t stop our bodies from aging (although we do fight it as best we can) we can keep our minds young.  I’m 75, came out to my friends and family in Dec last year and went full time Jennifer in January.  I’ve been truly blessed to have friends that support my decision, some even saying they were upset that I had not felt comfortable enough with them to tell them years ago.  But since out and full time I’ve gone out to a… Read more »

Shelly Diane Lynn
29 days ago

My first kiss from a man was at a local club when I was 27 so that was around 50 years ago. That kiss was so special I remember that kiss so well. Nothing is better than your first kiss from a man.

Crystal Johnson
29 days ago

@Cheryl Ann (Cassie) Sanders What a wonderful story Cassie. It felt like I was there and good experience all the wonder and excitement of the moment myself. I’ve had my first girl as Crystal with another cd but still waiting for that moment when I truly become a woman and I’m kissed by a man. Thanks so much for sharing.

Lindsey Jacobs
29 days ago

Oh my goodness! Such great stories and they provide such vivid imagery. I’ve not been kissed by a man but it’s something I’ve dreamt of for many years now – but only when I am dressed. I suppose as I’ve found greater and deeper ways to express my femininity, the thought of kissing a man (or even being intimate 🫣) ratchet up to a higher level. I am married (to woman, who doesn’t know my dressing yet), and maybe that’s been a bit of my hold up. However I do have one dressing experience from a few years ago that… Read more »

Jin Crocker
Active Member
28 days ago

I love kissing anyway possible! My first kiss from a boy was back at school. I had developed budding breasts at puberty and got tired of the boys teasing me, so I started letting them practice feeling me up before they attempted it on their girlfriends.

Lacy Williams
20 days ago

Oh girl! That sounds so romantic! I can imagine you feeling so insanely turned on! It feels like there was more to this story. More than one kiss. Maybe more than just kissing! There had to be. I hope he was gentle and it was all you hoped it would be.

Would love your thoughts, please comment.x
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials

Forgot your details?