Wednesday, July 1, 2020

Chat Me Up Redux – Part 1

My recent Chat Me Up post received a bunch of Comments that you can read at the bottom of that post. It also generated a batch of emails, which you can read following this period.


I have a few minutes to chat about this topic, however I really need hours of therapy to pull back the layers of the onion.

I have always loved getting flattering emails from men about my photos, it definitely stirs something inside. Over the years I have had some very personal exchanges with these guys. I always cut them off rather quickly because of how fast they escalated, and because how much I enjoyed them.

I believe I have always suppressed my feelings for men because of cultural taboos, but now at this age I can say that I'd be happy as a woman with a man.

Now your question was about being approached by men, I can recall two incidents worthy of mention.

First in Toronto Canada, I was waiting in the hotel lobby and a guy asked if I was  Lisa Somebody? I said no and we started chatting, the hotel parking, cold weather, and he ended with introducing himself and inviting me to meet later that evening for a drink in the hotel bar. I felt a wave come over me, like never before, I was just so filled with joy. That said I was scared crazy and hid in my room that evening.

The next time was in Madison Wisconsin, I was supposed to meet another girl like us at the bar, she never showed, but I struck up a conversation with a guy about 10 years younger than me, and we talked about hi-tech and then he started getting  a bit drunk and started telling me about problems with his wife. He put his hand on my knee a few times and I brushed it away, however I can say it was arousing. It was so validating that he was attracted to me as a female. Someone he knew came into the bar and he disappeared...

Paula Gaikowski

๐Ÿ‘  ๐Ÿ‘  ๐Ÿ‘ 

Hello Stana

In regard to your blog about men.

Not been approached for a good while but when I was younger , and then confident , I wanted to catch peoples eyes at times when out as Diana (and to some degree even now if I am dressed well and know I look good) .

I used to go many Crossdressing events/balls and so some regular ones too !!  – and many were in hotels.

On two occasions in the public bar going to the event entrance I have been noticed.

First time I was wearing a quite striking outfit , and felt great. The man concerned saw me enter the bar ( and me him) then he watched me move through.

Naturally I smiled , and when I was close he asked me to stop for a drink.  It was nice but I did the lady like “ Thank you but I am meeting someone” . It was good ego boost.

Second time I stopped at the bar to get a drink going to the entrance. While the barman was pouring the wine. I felt a arm go around me waist.

Slightly shocked it took resolve to remain calm. So I turned my head to look at the person. Man about my age. He looked at me and asked “ Hello darling let me get that for you “

My first thought was “ Yes, I’ve cracked it”, swiftly followed by “Shit I don’t want this”. When my drink arrived , I handed over the money telling my intruder “ No thank you I am with someone”.

Peeled his and off my waist , grabbed the wine and left.  [ If he had followed me into the event he would have had a shock]. Again great for me ego.

I may have mentioned the episode below to you before, so apologies if I have.

The only time it went further was purely by accident, not design. As I mentioned above I used to go to events and balls, mainly in London.

As a single girl , the Beaumont Society had a buddy system where fellow crossdressers would escort you on a night out. I used to have a regular man who was willing and perfect. Army man , married with 2 young kids, and nearly 6ft tall.

This event was a “normal” dinner dance that we got free tickets for.  As was usual I had hired an evening gown. In this instance an amazing silk/satin gown , and I felt truly feminine in it ( stockings and suspender lingerie !!). When he collected me he was impressed and said I looked gorgeous, which any girl wants to hear. He took me to the event. All went well as we were good friends. Food over ,  and as on previous occasions,  we were on the dance floor having a boogie when the music slowed. He took me into a waltz style hold , nice and close, for a slow number. And it felt really good. He was relaxed , his body next to mine, and the music played. He started to caress me through the silk/satin, which felt glorious and pull me closer. I was enjoying that. So after a minute or so I looked up at him. he looked down at me and then without any warning – he kissed me. And I mean really kissed me , pulling me closer. I reacted and kissed him back. All I remember was this was serious passionate kissing and nice !! All of sudden he stopped and pulled away. A look of horror on his face. He just said  “ Oh my god I am very sorry” and ran off. I was still in a stunned state and slowly walked off. It was only then the realisation of what had just happened struck me.  I had been by kissed a man , kissed him back and enjoyed it !!! Needless to say this did create a massive level of confusion , one that never went away. Was I a man who liked to dress and pass as a woman or a woman who had the wrong body.

We had to have a very long and open chat when we finally were back in our seats (and strong drinks).  We agreed to never talk about it to anyone. He was terrified I would tell his wife or make trouble that had kissed another woman with feelings. ( not withstanding I was really a man). I was more than happy to agree as confused as to why I kissed him back (and enjoyed it)

On reflection I think it was because I felt truly a sexy woman. I had dressed in a very sexual manner with the silk lingerie under that silk/satin dress , and the professional make up lady had made me look very attractive. I felt sexy when I saw the how I looked.

So I think feeling like that had stirred me and obviously stirred my date. So when we were body to body , his arms around me and the dress gliding over me , it only took him caressing me to take me over the edge and make him aroused. That one moment was all it took and Wham !!!   As you can see it had a huge effect on me. Although I have never experienced anything remotely like it again with anyone.

Even now many decades later whenever I think about that or read it - everything comes flooding back. Very emotional. Its hard to explain how I feel.

One part is very proud that I must have looked very feminine and sexy that a married man thought enough of me to lose control and kiss me.

Another part thinks was I at that point in life really a woman in the making , should I have taken the next step?.

I did consider that perhaps I was a homosexual after all but that was soon dismissed as don’t like men much anyway.

I think its a difficult area , one I have never resolved. I always wanted to convince a man I was really a woman and having done so to the ultimate degree I have made life more complicated.

I have a feeling I told you all this before but as it was relevant to your blog and I was sat at the computer I typed it from memory.

I may have given you the more detailed version previously which would have been copied from the book I wrote to record all my life events

Hope all is well in Connecticut

Love Diana x

๐Ÿ‘  ๐Ÿ‘  ๐Ÿ‘ 

Source: Rue La La
Wearing St. John

Karl Davies
Karl Davies femulating in a 2018 episode of British television’s Shakespeare & Hathaway:Private Investigators


  1. I have watched this episode of Shakespeare and Hathaway -- good episode of a pretty good show and they treat cross dressing with respect. It now seems like you need to subscribe to BritBox to see it. ~~sigh~~

    1. It is also available on Amazon Prime Video for $2.99 (that’s how I watched it).

  2. Diana,
    I would say do not worry too much about it. So few of us are 100% ANYTHING. If you are 99.9% straight male CD, you are straighter than most men out there, but 1 in a thousand men can turn you on. You found yourself in the thousandth man's arms that night. He felt he had a desirable woman in his arms, so he kissed her. Natural. He turned you on, you kissed him. Natural. He was married, so it went no further. He probably thinks you you every so often too.