Trannies Kissing

Trannies Kissing
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When I was in high school I was a bit socially awkward and especially around girls. I’d been with a number of girls, sure, but many of them left a lot to be desired. One year, a new family moved into my parent’s building and my life changed. That was because within that family, there was a very effeminate young male that I found on the back porch in total drag.
I was just coming upstairs from track practice when I noticed him. I was immediately struck by how beautiful he was in girls clothes and makeup. He was Puerto Rican descent and had full sensual lips that were even more enticing by the matte cranberry red lipstick.

I was frozen when I saw him. When he saw me, he looked horrified and backed into a corner thinking that I was going to wail on him. I assured him that he was safe and contrary to his fears, I actually thought he was really cute. The words just came out of nowhere because I was so smitten.
We wound up sitting on the back porch steps talking well into the night. And it was obvious that we had a mutual attraction for one another. We decided to slip into the basement stairwell of a vacant apartment in the building so that we could talk more freely which led to hand holding, which then led to the moment where I leaned in to kiss him. That led to another kiss, then another, then another, then more prolonged kissing and caressing. The next thing I knew, he was sitting on my lap while we continued kissing.

Knowing that our families would wonder where we were, we reluctantly decided to part and head back to our apartments. But this felt too good to abandon so we would meet regularly at the basement stairwell where we would kiss for hours. The level of intimacy was unmatchable and no girl in the neighborhood could even come close to what I experienced with this cross dresser. Every night I would rush from the dinner table just to meet up so that we could share those sensual kisses.
Unfortunately, I went away to college and when I returned that fall, I was told that this family had moved to California after the father of the family found a job there. This was before email and social media, so we never got a chance to reconnect.

I did find some consolation in the fact that one of our neighbors talked about how the son in the family cried the whole time he was leaving. I could have been wrong, but I was hoping that those tears were because we would not be together again.
Sorry if this story does not end in this cross dresser and I fully making love, but our kissing sessions were filled with the most sensuality that I’d ever experienced and something that will always hold a special place in my heart.
No “happy ending,” but a beautiful memory nonetheless.
No “happy ending,” sadly. But it’s a beautiful memory.
What a beautiful story and sad 😢, I had the same sort of thing happen to myself when I lived in Exmouth Australia and John went back to the United States. I have kicked myself ever since for not being truthful to my feelings.
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Cheryl Ann Sanders |

Jul 2, 2018

| 1 Reply

About the Author ( Author Profile )
Cheryl Ann Sanders was a frequent contributor to Transgender Forum in the past. She has been absent for several years while writing and publishing a (quite successful) straight novel under another name.
If you are Transgender or a Crossdresser and are looking for breast forms please visit www.TheBreastFormStore.com.
Back in the 1990s, TGForum was more interactive. The bulletin board bristled with challenges and responses. One was: describe your first kiss as a woman. Below is my response. What’s yours?
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 romance and a physical relationship with a man to be of interest.
He was a trim, good-looking man in jeans and a button-down 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. The first kiss was actually 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. The power of my instantaneous reaction if not quite shocked, then definitely surprised me; it was so immediately, so completely feminine, so natural, so total, so hotttttt! 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 seem 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.
As Regina Leigh posted on this topic, being held instead of holding. Being kissed instead of kissing. Wow!
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 sliding over my lip gloss, then settling into a quiet moment of incredible intimacy, the sensation of my breasts caught between us, flattened against his solid chest; and through the soft folds of my skirt, the bulk of his thigh feeling warm and strong pressed against the inside of my own right thigh: years later the memory of that kiss and that hug and those quiet whispers against my ear still makes me breathe in short shallow gulps as I type this.
The first kiss. The first kiss. Is there anything quite like it? Well, there is, but, as Roberta said in her reaction to this topic, that’s another story.
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Cheryl Ann Sanders was a frequent contributor to Transgender Forum in the past. She has been absent for several years while writing and publishing a (quite successful) straight novel under another name.
Many also know her TG novel A Woman’s Passion written under the name Alan Barrie. It was at one time the bestselling TG novel of all times. Although more than 15 years old, it still sells in dribs and drabs on Amazon . Still others remember her essay that appeared here several years ago: …And What I Wore . An “occasional woman” at that time, this was a memoir of a weekend she actually spent as a woman with a man in New York City. That memoir can still be found in our archives. Unfortunately, the photographs that illustrate that archived version have been lost. A safe PDF version with its photographs still intact is available for download here . Cassie can be reached via email .
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I am a trans girl myself and I remember my firstn kiss how it was, It was with a blackman I had met at a bar , He kept looking at me and then he came over and ask me to dance! He was tall and handsome and I was so nervous , we ended up at a drive in movie. He parked in the back and ask me to come closer and I was breathing so hard , then he gave me the wettest kiss it was great, we kissed for 2 hrs and then we got a motel room, he fucked me for 2 hrs it was so wonderful, ill never forget it!

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