The Next Step, and Amy says Goodbye to an Old Friend

By the time the next month’s Pub Night was due to roll around, I had been out exactly twice. The first was Pub Night, and then at a small gathering held at a CD friend’s place. All went well both times, even though it had been stressful at first, but that of course made me hungry for more. I was determined to go to the next one, but I had a problem with my face.

You see, that guy seems to really like the beard he says he’s had for 40+ years, and he’s rather reluctant to shave it off. Of course, I try to be a nice girl and not trouble him too much. Though by now, I certainly felt as if it was starting to cramp my style!

After a lot more thought and soul searching, we were able to reach an understanding of sorts; it’s only hair, and if I look awful, then a few weeks of not shaving will solve the problem. So on a Sunday evening, shortly before the next Pub Night, I did just that. Although I had been wearing it very short for quite some months, I could not believe the difference it made in my appearance! I thought I looked weird, but also much younger, too. My wife also couldn’t believe it, and my kids wanted to see pictures of the new me right away.


I’d first grown it, back in my twenties; I did it in part to add a few years of apparent age to me, and I had a running joke for a while that I’d shave it off in 20 years or so to look younger again. It took me double that time, but sometimes I do tend to procrastinate too much!

Shaving every day wasn’t the chore I was afraid it might be, and I’m very fussy, shaving mornings and evenings. I emailed one of the experienced girls I’d met and told her about the new me. I asked if she would help me with makeup before dinner, to which she gladly agreed.

The day of the event finally arrived, and now knowing a bit more about the lay of the land, so to speak, I didn’t arrive as early. I was underdressed to make it much easier to change into my femme clothes. With it still being cool weather here, I wore a light jacket, which tended to cover up the slight bulge made by my padded bra. I planned to wear a long black skirt and long sleeve red sweater. With my forms in, I manage to gain a “C” cup. With an improved padded panty, pantyhose, my wig, and some jewelry to round out my attire, I would be presentable.

Really, I didn’t have anything more than small “A” cups, but as a guy, and having a totally flat chest, I was still rather conscious of them. Even so, I was still more than an hour early. I went into a nearby coffee shop for a coffee and snack. I took off my jacket and sat with my unseen bra and those little boobies in full splendor. No one paid a second glance my way; I was just another coffee drinker on a busy afternoon in the city.

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After making my way over to the pub, I met up with my friend, who taught me a few makeup basics after I’d changed into my female clothing. When I saw myself in the mirror, I was amazed at the difference that some foundation, colour, and eye makeup made in my appearance. My first reaction was noting that I looked like my mother! (Not a bad thing, actually).

When I made my appearance downstairs I received several compliments. I wasn’t as nervous as the last time; it helped that some of the girls I’d met last time were there again, and they made me welcome at their table. After a nice dinner and some good conversation, it seemed too soon for the evening to end, but end it did.

I’d made the decision to drive home totally en femme. A few of us left at the same time, and what a feeling it was walking out through the main part of the restaurant and out into the street! I felt as if everyone was watching me. In truth, a few certainly noticed us, but no one said or did anything out of place. What do guys do, they look at women, so to get a few looks from men while dressed as a woman is totally normal and is something one should expect.

I did what any GG would do; kept my head up, kept walking, ignored the few looks that came my way, and walked confidently to my car. In this part of the world, at this time of year, it’s well after dark, and though not an unsafe area, one needs to exercise caution, like any woman should.

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With it being a long drive home and late at night, I decided to pick up a bit of refreshment to help fight the inevitable fatigue. There is a place that is an hour or so from home that I often stop at. This time of night it’s normally quiet. It has a drive-through window, but of course, I decided that I should up the ante a bit by actually parking and going in to order in person. I pulled in and was able to park right by the door. It’s well lit, and I nearly chickened out sitting there straightening my hair. It would be disappointing if I didn’t walk right in, and I didn’t want to miss an opportunity, so I gathered my courage and got out of the car.

There were a couple of people in line in front of me, but it didn’t take long before it was my turn. I tried to pitch my voice a bit higher than usual when ordering. I got my hot tea and headed back to the car. One of the best things to occur happened on my way out of the store; a young man held the door open for me!

In all, a few more boundaries were crossed, some barriers broken, and however one wants to phrase it, I got that amazing sense of peace and contentment, which seems to come over me with this. The feeling lasts well into the next day. I’m enjoying this journey as Amy stretches her boundaries, and I hope you are enjoying my recount of them as well.

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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.

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Olivia Livin
Trusted Member
4 years ago

Although I totally missed it when I saw you just after the great shave, it does make you look younger and easier to do the make-up lol.
Being out and about is just like the early shopping days isn’t it Amy. It’s enjoyable, addictive and gets easier with every success. I love hearing stories like this, and knowing that they are helping some of the readers move a little further along the path.

Active Member
4 years ago

Lovely to see Amy develop and try her wings.

Trusted Member
4 years ago

Each step outside the shadow and into the sun any one of us makes, is a giant leap forward in the “normalizing" of us. I used to be on the alert when going out; watching my surroundings constantly and ready to go primal if needed. So, far, only once have I met with unpleasantness. Over the course of a few years now, I too notice that I am not being noticed nearly as much as my self conscious mind would like to imagine. Seems like really, no cares…99.99% of the time, I am treated with respect and kindness and ow… Read more »

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Kim Paige
4 years ago

Great story Amy! Thanks for sharing!

Paula Malmborg
Active Member
4 years ago

Great story Amy thanks for sharing

skippy1965 Cynthia
Trusted Member
4 years ago

Amy-great article -thanks for sharing! It’s so good to hear of other members’ early times out. For me it reminds me of my own early forays (I just got back from vising Atlanta and watching my Hokies throttle GA Tech in football while in full Cyn mode). But it’s also inspiring for those who are teetering on the precipice– wanting to venture out but afraid of the consequences. Reading your story COULD be the impetus to give them confidence to try it!

Gemma McDade
4 years ago

Hi Amy, that is a truly encouraging story, thank you. I’m also in the early states of setting my female self free so your updates really help me see what might be possible. Thank you so much and keep the updates coming! Gemma.x

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