Dinner out for Amy!

Having been to a few pub night dinners with the (Xpressions) group, which after just a few visits, I’d become very comfortable with, I got wondering about doing a bit more. The pub night venue had been carefully chosen a long time ago and remains the same place every month. This is because it’s in an accepting part of town, the room is private, with a private washroom to use, and to change in, as I’ve described before. So, for those girls who are just learning, or testing the waters, it’s about as safe as you could possibly get outside of the privacy of a home.

They also have monthly dinners, but the venue varies and can be anywhere in this big city, however, it’s not the same kind of the protected environment that we enjoy upstairs in the pub. With the experience and confidence I’d gained with doing the pub nights, along with help from the others about presentation and makeup, my femme appearance was getting better. I wouldn’t say that I was truly “passable” (I think it’s a bit of an overworked term here), however, I was at least to the point where it wasn’t glaringly obvious that I was simply a guy in women’s clothes.

January 2021 Live Session - cdh

We don’t always need to be passable, however, I think for most of us it’s like a Holy Grail. To go out into the world in public and be taken for what we want to be, or for some who which that may not be possible, but to look as good as we can and invite attention – positive attention that is.

For some reason, as of late, I am driven to push my femme boundaries further by going out more and by going to more public places. I’m now feeling I’m ready for another step forward to a more public place though still with the security of being with my fellow crossdressing friends. However, I decided to sign up to go out to dinner to a really nice restaurant with a few of my crossdressing girlfriends and to try to work out the other logistics of going out on this public trip.

The biggest problem was at this particular time, one of my kids was back at home in between college terms. None of my kids know about Amy, although my wife knows and is supportive. So, getting ready at home was an issue. I would have to get into Amy mode somewhere else and then I’d have to change back into male mode before turning home. The good news was the fact that one of the other girls came to my rescue by letting me change at her place. From there we planned to drive together to the restaurant and meet the rest of the girls. This arrangement also gave me kind of a double check on my appearance, just to make sure I looked just right before we left for the restaurant.

Visit Transgender Heaven

For tonight I had a new cream-colored wide knee length skirt with a black lace hem along the bottom. I paired the skirt with a white top embellished with gold thread. And as usual, I had on my padded panty, waist cincher, and breast forms to give me some feminine shape underneath my clothes. Through the days leading up to the event I was quite a bundle of nerves, and even didn’t sleep well the night before.

Even though it wasn’t the first time I’d packed Amy up into a gym bag to be released later, I still went a bit crazy making sure that I had everything I needed –  forms, pads, and I almost forgot my wig! That would never do! A nice, respectable looking middle-aged lady with short grey hair with a guy cut! Wouldn’t be a good look for Amy at all!

When I arrived at my girlfriend’s house, I changed into Amy and was told by her and her SO that I looked fine. The SO quite enthusiastically proceeded to do my nails and helped me with my makeup. Having my nails done was a first for me today. This process was very relaxing after all the previous worry. After being suitably dolled up, it was finally time to leave for the restaurant.

When we got there, I was getting quite nervous again. This is a normal state of mind for me when I get to a place in Amy mode. I’m usually not too bad during the trip but when I get there and have to get out and go in, it gets to me again. However, this time there was myself and others travelling in one of the other girl’s car, so unless I wanted to sit in the car, and go hungry, I had to go in.
Though having some more experienced company helped, it was still nerve wracking to walk in through the main entrance past many other patrons and a group of men sitting together to get to our table. Like times before, we got a few looks from the guys, but we just held our heads up, looked straight ahead, and calmly walked through. No idea what they thought, and it really doesn’t matter.

As expected, we had our own table but just at one end of this rather upscale restaurant. At least the tables weren’t too close together, however, the place was rather busy because it was a Saturday night.

The wait staff were without exception, pleasant and courteous. The food was excellent, and I got to know a few other girls who like to do the dinners but not the pub nights. As the evening wore on, I was again beautifully relaxed and enjoying my time as Amy, then before I knew it, it was time to go.

So, it was back to my friend’s place where I removed all my girly things, (except for undies!) makeup, and the hardest part was the nail polish. She did a thorough job, with primer, polish, and clear coat. They were beautiful but destined not to last!

Though in a very different way, I’ve found that the saddest part of crossdressing is when I take my bra off. That’s when it really sinks in that I’m going back to guy mode and I’d be interested to hear if any of you other girls find the same thing happening to you at that time in the process. As for my wife, and most other naturally born women I’ve known, they can’t wait to get their bras off at the end of a day! However, for many of us crossdressers, it’s the other way around. As for Amy, a bra is a potent symbol of womanhood.

It was finally time to get into my car for a very mellow hour’s drive home.
Once again, this was a big step forward for me, a new barrier crossed, and some important confidence gained. All thanks to all those other girls who helped me and with which I wouldn’t have been able to make this next step without them present.
One usually wants to have a nice appearance, but the most important thing is to have the confidence to just get out and be oneself, whoever that is at the time!


When you girls go out in public, do you feel more comfortable being with other crossdressers or flying solo by yourself?

Do you girls get really nervous while you’ve got your girl on and just before you make your public appearance around a bunch of people you don’t know?

Do you girls have sort of a total let down when at the end of your time of crossdressing you remove your bra? Most genetically born women can’t wait to get that darn bra off and it just seems to be the opposite with us – we can’t wait to put it on!


Thanks for taking time to read my article and please feel free to answer any of my questions posed above!

Sincerely, Amy



More Articles by The Author

The following two tabs change content below.

Amy Myers

I'm 60+, hetro, married, and love dressing up! I keep saying and feeling like I'm new to this, but I have dressed from time to time since my pre teens, but just late 2018 it seems to have become of a bigger part of me, rather than just a role I played from time to time. I'm interested in music, cars, photography, and plus other interests.

Latest posts by Amy Myers (see all)

5 1 vote
Article Rating
Notify of
Inline Feedbacks
View all comments
1 year ago

Well done again Amy. I do know well the feeling of taking my bra off at the end of a long day wearing it and love having that so feminine experience but it really does not bother me as the bra really doth not maketh me a woman, lol. I am Linda however I am dressed and she is me as well as ‘him’, we really are one and the same whatever the presentation? I enjoy getting dressed and made up but I like more being out in the world as a woman. You had a lovely time out and… Read more »

Rochelle Mills
Active Member
1 year ago

Wonderful story, Amy! So glad to hear you have found a couple great groups of CDs to socialize with. It is so refreshing to go out en femme with CD friends and SOs for shopping, dinner, nightcap, etc. I hope your story encourages others to seek out CDs in their areas for some fun evenings out. Even though I’m from a smaller metro area, I am grateful for some sisters I’ve met through this platform who like to go out on a regular basis. Like you, I started just going to a regular pub nights at a friendly local LGBTQ… Read more »

Rochelle Mills
Active Member
1 year ago
Reply to  Amy Myers

Yes, Amy, I agree! You really don’t know what you don’t know, until you make an initial connection or two to other CDs in your area. I have made a great group of new friends over the last several months. Although meeting others on this platform is great, nothing can replace the in person connection with kindred spirits. So wonderful and enriching. Kinda wished I had gotten out the door sooner LOL.

Alicia C
Active Member
1 year ago

Having recently done my first solo daytime bright lights trip, I’d say the hardest part was committing to the day and gurl mode on. Once the make up started, I knew I was all in for the event. I went to a couple local places like walmart for girl items and found myself rather relaxed. Did I get made ? maybe once or twice but so what, they kept to themselves perhaps curious more than anything. Confidence will carry you through the day. It is much easier having your CD gang for regular daytime outings which are also much fun… Read more »

Active Member
1 year ago

Dear Amy, How nice to see you grow into a confident and outreaching woman. Though it is now over seven years since Marianne made her first public appearance, I can still remember both the anxiety and the elation. With one wonderful exception, l have always gone solo. It may seem scary, but as l normally dress to blend into the crowd and easily pass for a woman, I have rarely drawn any attention whatsoever. My favourite activities are shopping and dining out, but I have also been to the movies and even attended curch at the Christmas Day morning service… Read more »

Nix Knickers
1 year ago

Dear Amy;
Have no fear, you do not look like a guy in girls clothing, you look like a group of girl friends out for a nice evening out together. I bet you have a lovely time.

I love a full padded sporty bra myself, the breasts can look real by themselves. The tighter the straps the better.

Sometimes though a nice silky-satin cammy can feel nice without a bra.

Lots of love;


Nix Knickers
1 year ago
Reply to  Amy Myers

Dear Amy; The sweet pleasure of your reply to my comment about your post is thrilling, I hope that we can chat together as friends again soon and discuss our girlie thoughts and desires. Satin camisoles are one of the few items of underwear I can wear out in public, under my male drag. I have worn a bra out also but I get some strange looks from other people, perhaps I am just being a bit self conscious. I will post my photograph soon, I still have to work out how to size it right so it fits the… Read more »

Hannah Feldman
1 year ago

Thanks for the lovely story, I’ve never done a night out like that before, wish I could. I know the let-down going back to guy mode. One time I’d had the home to myself for a sufficiently long time that I’d put all guy clothes away and out of sight for 5 days while I was in Hannah mode. The let-down when I had eventually to substitute pants for a skirt, and remove the bra was so depressing.

skippy1965 Cynthia
Trusted Member
1 year ago

Living alone, I am free to dress most of the time when I’m off work and since my hair is my own, it really doesn’t take much to “f;lip the switch” so to speak from stealth cyn mode that I do at work and pool o full Cyn mode; just pop in forms , brush my hair down from the ponytail and switch to more femme earrings, and add lip gloss. So I am usually keeping my bra on except at work and pool. “Like times before, we got a few looks from the guys, but we just held our… Read more »

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?

Create Account