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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
@cassiesanders Thanks for sharing Cassie.
Never had this experience but been approached a couple of times in a nightclub. Cut both of them off politely but immediately.
Can I ask did he know you were trans when he first started talking to you? Did you tell him or was there a moment of realisation? Did it change his attitude to you? Did both of you chat about the issue?
How did the night end? Did you feel safe?
Sorry for all the questions, just curious about your experience.
B x
Yes, Bianca. He knew from the start, if for no other reason, because of the club we were in that night. He (we, actually) scrupuously avoided the subject, both sharing (enjoying) the conceit that I was simply a woman spending time with a man that night. That "first kiss" night went just a bit further. But I have another multi-part post you might enjoy called "and what I wore" that (umhhh) goes further.
@cassiesanders Thank you so much for sharing Cassie. Yes I guess the fact that you were in an establishment perhaps frequented by our community made the situation easier. How exciting it must have been for you.
I think I still have a huge barrier up from an acrimonious divorce (nothing to do with Bianca who was born post divorce). I probably cut situations like that off immediately for fear of rejection. And perhaps feel that I can keep the dream alive in my head that on those occasions Bianca does get out to play, that I am Bianca in all my feminine glory. I have always went to my favourite club in the city, not known to be a gathering place for LGBT+ community, but did strongly support the LGBT+ month last year, flags and all. I remember the first time there en femme asking if it was OK to use the ladies bathroom, the young female assistant seemed perplexed ‘why wouldn’t you?’ I thought ‘surely she must know! Are they so accepting it is not even an issue in here. Probably helped make it my go to on a night out (along with great music and cocktails 😂)
If a guy did approach me the questions in my head would just blow my mind,
’Does he know?’
‘Does it matter?’
’Is he gay?’
’Does it matter?’
’What are his intentions?’
’Is he just trying to be friendly?’
’Do I want to flirt?’ (could be fun)
’If I do will it be misconstrued?’
etc etc
But yes sometimes wonder what this situation would be like from a woman’s viewpoint.
B x
@cassiesanders 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.
Crystal
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.
Thanks for the great comments, Anita and Alicia, et. al.
Subsequent to this, but not many times, and not for many years now, I have, as they say, gone much further than this. I have some of those experiences as journal entries, but I'm afraid that Heaven is not a place for those to be shared!
Let's just say that I found it as unexpectedly "fulfilling" (or even more so) as was that first kiss. There is simply no feeling as quite as feminine as being a woman with a man in a romantic situation.
Loved the article Cassie. Rings true for many of the girls who come to CD Heaven. Still just a fantasy for an old lady like me. But I still dream. Love to read about some of your other further experiences. Where can we find them? I may become an LI girl myself over the Summer as we intend to buy out by our daughter ad grandson on the North Shore. I hope to join Femme Fever when we do move and make my public debt at age 70!
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.
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 didn't bring any male clothes with me. Just female clothes and accessories.
The first two days were great. I went shopping for souvenirs and clothes for the stay. The second day I went on a sightseeing bus tour of the Keys and it was enjoyable.
No one questioned me about my sexuality and I was accepted by everyone as a single girl on vacation having a good time.
I knew that there were guys looking at me but I dismissed them as I wasn't interested in any of them.
The week flew by and on the last night before I was going to be leaving i went to a club to listen to a band that I wanted to hear.
I was sitting alone listening to the music when a guy about my age came over and asked me if I wanted to dance with him?
At first I refused but he was persistent. He was good looking and had a nice smile so I accepted his request and got up to dance with him. He held my hand and we went to the dance floor and began dancing.
He was a excellent dancer and I was enjoying dancing with him. After we danced for a while we went back to my table and talked. He was very respectful and he made me laugh at his jokes and I was finding it hard to believe that I was actually glad he had asked me to dance.
We danced some more and when the last dance of the night began it was a slow romantic song. He put his arms around me and I moved close to him and put my head on his shoulder. I could feel the heat of his hand touching my waist and other hand that he was holding mine with. The song ended way to soon and we stood there looking at each other.
He put his hands on the cheeks of my face and brought his lips to mine and kissed me standing there on the dance floor.
I didn't expect him to do anything like that but I was secretary glad he did. His lips weren't soft like a girl's lips are but instead they were thin and masculine and Iiked to be kissed by him
Cassie, my toes curled in my heels as I kissed him back and i
put my arms around him to keep him from pulling away from me
I never dreamed that I would kiss a guy but here I was hoping that he would kiss me some more
He walked me out to my car and kissed me goodnight and I kissed him back.
Reluctantly I got in my car and drove to my motel tingling all over and wondering what would happen if I wasn't leaving for home in the morning?
Hope you enjoyed my first kiss experience
Stay safe and enjoy your next kiss
Janney--
I LOVED your account. It was soooo similar to mine! There is, again, simply no feminine feeling quite like that one, is there?
Your absolutely correct. There's nothing that compares to the feeling of that first kiss. It sort of confirms that you are a desirable feminine girl
How beautiful Cassie , a memory to have forever xx
You're right, Tiff. It's been a long time since that first kiss, but I can remember (feel) it like it was yesterday.
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
Daisy,
It was my first, but it wasn't my last. I'll just say this: if you are open to it happening, it probably will. (Especially since you're so cute!)
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 months. I love kissing and fondling but sure is exciting to do in public . It makes one feel so attractive and desired and really helps the ego
Yep, Deborah.
I have to admit that you put your finger on it. It's wonderful for two ways: it's soooo nice in and of itself; but also, it's so validating, isn't it?
@debbiedd Deb, my first guy kiss was very similar to yours. It was not my first time kissing a guy but my first time as a girl. A totally different experience.
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
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
That, I think, was just bad luck, Stephanie.
My memoir was of "my first," but not my last! (I would guess I was kissed by a total of somewhere between five and ten men over 30+ years.) It's true that some men are much better at it than others; but I never had one who was as off-putting as yours. And it really can be very sexy and validating.
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
I remember that club, Karalyn's Oasis, Terri! And there was a restaurant on 23rd Street called East of Eighth that several of us would go to for dinner before that club. Seems like a million years ago, seems like yesterday.
I also went to East of Eighth and I met Terri at CDI in NYC where i went for years.
Gee Terri, given your good looks, I bet you were a gorgeous young woman. I'm surprised it didn't happen often in your life. So many of us are taken by surprise when we realize that our thoughts and feelings as women run deeper than we know.
Exactly, Arlene. It never occurred to me before it happened that I could be so comfortable with it.
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-
The first time a man kissed me was about 7 or 8 years ago. I had a girlie weekend away and on the first night, I met a man I had chatted to quite a lot online. He was with someone else, but at the end of the night, I bumped into him again and we chatted for a while as we had a couple of drinks,
As it was very late and I was up very early that morning, I got up and bid him goodnight . I leaned down to give him a goodnight kiss on the cheek, but he turned his head and kissed me on the lips!
It was just a 'mwah' goodnight kiss, but was still a kiss! I left to go to bed feeling a bit shocked but also a bit excited and definitely with a smile on my face. He is still a good friend and I have met him a few times since then.
I might have had a few 'making out' type kisses with different men since then!? 🙂
Cassie
You write very well and the reader has a very good sense of where you've been and how you feel.While I've NEVER given in to a man, I actually (and very surprisingly) could relate to what you're describing. Just for the utterly feminine feeling it brings. Not there- at least not yet and probably never.
Loved the story though
Abby
Thanks, Abby. For me, too, now, it's only in memories. But those memories (and journal entries I re-read every once in a while) stay sweet.
I had met this man (he was younger than I) for lunch several times. It became obvious after 2 or 3 meetings that he hoped for more than just having lunch together. This was outside of my comfort zone. After few more meetings at which he continued to ask for a kiss I did consent for some "thank you" type kisses. Eventually, I told him that I was not going to be able to give him what he wanted and that it was not fair for me to continue to see him under those circumstances. He always treated me as a lady and I enjoyed being with him.
Carole, even just that though, in my opinion, is a very special kind of memory for a crossdresser. As they say, there is nothing that a crossdresser can wear that is quite as good as having a good-looking man on your arm as you walk down the street!
Just had to smile when I was watching television show Highway Thru Hell
Two men working on recovering a wrecked truck and afterwards one of them said
You'd be surprised what two men can do
It made me think about what I did on vacation with a man who I met with.
I guess that you can read between the lines and figure out what we did
Hey Cheryl Ann. I think that you really did read between the lines about what we did
There really is nothing like that first kiss when dressed as a girl, my knees really did go weak, and my heart skipped more than one beat. You never forget that feeling. So happy for you that you know that feeling of being desired.
Stay safe
Evelyn x
