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.

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

 

 

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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 (used to be) bestseller on Amazon, A WOMAN'S PASSION. (Those sales have been eclipsed in recent years by all the $2.99 tg junk writing on Amazon; however, still sell a few copies a month.) 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.

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Anita Harrison
Lady
Member
Anita Harrison (@anita)
7 days ago

Wow. How romantic and well described. I think we have all dreamed of this happening to us and wondering what we would do, how would we play it. Do we kiss back, tongue play or is it just a goodnight kiss and do we want to go further. We won’t know until it happens to us somewhere quiet and romantic but why do we go out to meet men if we don’t want the thrill of being kissed and romanced ? Personally if it happened to me, I would be jumping his bones before he got away.

Alicia C
Baroness
Active Member
Alicia C (@aliciacd500)
7 days ago

what a great experience ! I think we need to stop worrying about what our sexual preference label is and throw it out. If you and they feel comfortable and enjoying whats going on, great. Its all good as you explore new things and see how you feel, if you want to go back for more and go further. I really enjoy being with intimate with men and so guess that makes me a hetero girl, but I’m ok with women too so I’m a lesbian ? … see the labels start to get silly. Have fun, enjoy, be safe.

Jannie Murry
Lady
Active Member
Jannie Murry (@missey)
7 days ago

Hi Cassie. I just read your post and wanted to share with you about the first time I was kissed by a man Two years ago I went on vacation away from where anyone would know me to fulfill a dream of mine. I wanted to live as a female the whole week I was there to see what it was like not to have to change back into my male life. I went to Marathon Florida in the Florida Keys where I had made reservations in a resort that’s trans friendly. I was so adamant about it that I… Read more »

Tiff Any
Lady
Trusted Member
Tiff Any (@tiffanni)
7 days ago

How beautiful Cassie , a memory to have forever xx

Tiff Any
Lady
Trusted Member
Tiff Any (@tiffanni)
6 days ago

I hope that never goes

Daisy Marie
Duchess
Active Member
Daisy Marie (@missdaisy)
7 days ago

Wow! I loved the story and how it was told by you, Cassie!

Right now I’m 29 years old and wondering the same situation happening with me.

It wouldn’t be the first time that a man would try to kiss me, but in a romantic situation, lights dimmed, slow music, dancing…..a perfect first kiss…..that’s what we’d label here in Brazil as a “girl’s dream”!

xoxo
Daisy

Deborah Sullivan
Duchess
Active Member
Deborah Sullivan (@debbiedd)
7 days ago

My first time was at a tg event in LA where I went with another cd friend. There were lots of admirers there and a guy maybe 10 yrs older at the time approached me to dance. I was both nervous and excited. We danced and chatted a bit and during a slow dance he kissed me on the dance floor. Sent chills up my spine. We sat then in a booth both of us touchy and amorous kissing like school kids. Later we went to his car to chat and makeout which later turned into a relationship for six… Read more »

Deborah Sullivan
Duchess
Active Member
Deborah Sullivan (@debbiedd)
6 days ago

so much so Cheryl

Michelle Kroger
Lady
Member
Michelle Kroger (@michelle1954)
6 days ago

I am envious of you.That sounds like a great experience that I wish I had.When I’m dressed i Am a woman and
am attracted to men.But so far no such luck.Good for you gilrl

Stephanie Kennedy
Princess
Active Member
Stephanie Kennedy (@qtestephy)
6 days ago

Hi Cassie I must admit it sounds lovely and exciting. You have wonderful way of writing. My first kiss was horrible i felt like the guy was trying to eat me. I hated it. Some men just do not get it. I always prefer the kiss of a woman. They get it for sure.
Luv Stephanie

Terri
Baroness
Active Member
Terri (@terrim)
5 days ago

I guess my first kiss from a guy was in the early 70s. I went to a bar in the city (NYC) called Karalyns Oasis. I guy sat next to me and we talked. He held my hand and then he kissed me. I was shocked of how I liked it. I thought I was not attracted to guys. I was 31 or 2 and felt like a woman. Im 71 now.
Terri

Jane Don
Lady
Member
Jane Don (@janedon)
2 days ago

This is still something I dream of–I’ve had sex with men but not one has really made me feel like a Real woman-not one– I dream of the day-

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