After the events I have already related, I kept crossdressing in private, and even took (progressively) to wearing panties everyday, with very rare exceptions when I thought there was a good chance someone would see them for one reason or another.
Then came a period where I crossdressed less, I even refrained from any item of women's clothing for a year and a half (but thankfully didn't purge, just didn't touch my stuff) as I'd grown a beard and it just didn't feel "right" to dress in women's clothing with a beard, even when alone (I've since shaved that beard, and grew another, and shaved it, ...).
After a while, though, the desire to crossdress started becoming overwhelming, and I decided to let go of that pointless restriction placed on myself. Back to fully dressing in private, back to panties everyday. Nice poly satin or silk satin camisoles under my shirt and sweater in colder months, even at work (some people might've seen straps now and then, but said nothing).
On particularly cold days, I even wore pantyhose under my jeans and socks.
The covid lockdown, terrible as it was in many ways, had one upside for me (and I would suspect others amongst you): more time in skirts!
The first couple of months were blissful, I was in skirts everyday! Sometimes with a nice blouse, sometimes with a T-shirt when I had virtual work meetings scheduled (just have to remember never to stand up during the meeting).
This carried on as the restrictions lifted: full fem when alone or with my parents, male presenting (but with nice underthings) when in public.
Until I hatched an idea: instead of (poorly) trying to pass when crossdressing, I could aim for a deliberate "man in skirt" look.
I think part of the backlash against crossdressers is the idea that we're trying to deceive people, or trying to encroach on the realm of women. When we're clocked, our confidence is shattered and mockery ensues.
The covid lockdown had opened me to a reality I didn't want to give up; I don't want to spend the rest of my life hiding, only wearing the clothes I like on rare occasions.
And I can't transition, for social and financial reasons. I also probably wouldn't pass if I did, anyway.
So, why not go for a look where I'm not at all trying to pass, just wearing clothes I like? Specifically, I was considering making the outfits I wear when I have virtual meetings a mainstay: women's clothing below the waist, men's above, no makeup or wig.
Of course, the key would be to be confident about it, as if I was to wear skirts in male mode (Metal shirt, big beard) in public and show external signs of nervosity, I'd expect to draw much more negative attention.
And I think many others here would be nervous at the idea, so imagine how bad it could get when you suffer from a rather severe social anxiety disorder.
So, I devised a 3-step plan to acclimatise myself to the practice:
1) "The expedition" (silly name, I know, but I wanted it vague in case I mumbled it out in front of the wrong people).
2) "The road trip".
3) "Every day".
You read that right: the objective is to be in skirts every day in the future. I even have a deadline in mind: my 40th birthday.
It's an ambitious objective, with many obstacles, and I might not go through with it, but I'm sure going to try.
Between the 8th and 16th of July, I had an opportunity (for reasons too long and boring to delve into, I couldn't do it before or after) to put step 1) into action. So, I planned it for saturday 09/07/2022.
There were two objectives to this expedition: the first objective to try on a skirt in a store. Although I do the bulk of my purchases online, I'd gone to stores to buy women's clothes quite a few times (never used the "note" trick), with various degrees of anxiety. I had bought items, but never tried any.
Salespeople tended to think I was buying for my GF/spouse (or pretended to think that so they could sell me gift bags). This time, I would try it on, making it quite obvious I was buying for myself.
The second objective was to change back into it after paying, and leave the store whilst wearing it.
I'd planned it that way so that I had an out at any time (I could simply buy as usual or I could do the first objective but not the second), and if I went through with both objectives, I'd only have to walk back to my car in a skirt, a relatively short process.
As a bonus, I'd wear pantyhose, this time not covered with socks. I reasoned it was possible but unlikely for the hose to be seen peaking between my (men's) shoes and jeans. That way, if I walked out in a skirt, I'd have the appropriate hosiery on already.
On the day, I was anxious, but less than I thought. I planned on going to a mall removed from my own area: ~200km away, and on the other side of a national border (with a country that speaks the same language as mine (not English, I'll translate anything said), didn't want to risk communication issues).
I reached the mall and browsed the wares. I had scoped a few items on the online shops of some of the stores, but I knew the inventory in the physical stores would be smaller, so I knew there was a possibiity of not finding anything of interest. Still, I thought there was a good chance.
As I went from shop to shop, I came the realisation that the few skirts present were either ugly (in my eyes) or very short. I left the mall and tried to reach other stores in the area, only to arrive too close to closing time. I prepared to leave, disappointed, when I decided to head back to the mall.
I spotted a store, close to the entrance, that I had not been to, so I went in, and lo and behold, a decent skirt, in two different colours (black and red).
On the way back towards the mall, I had psyched myself into doing when I had come to do, so I didn't hesitate much and head towards the changing rooms with 2 sizes of the red skirt in hand. Ecstasy at finally doing something I'd been dreading in the past far eclipses anxiety.
The salespeople saw me, but their only reaction was a greeting. I tried the skirts on, changee back into my jeans and bought both the red and black versions of the skirt. I asked the salespeople if I could go back to the changing room to wear the skirt out, and they acquiesced. They both had remained professional the whole time.
At that point, I was committed, I was going through with this mad idea... and so I did, I put on the black skirt (less conspicuous than the red one, plus it went better with my dark grey shirt) and left the store. I knew I had to project confidence, so I couldn't rush back to my car, mumble or scan my surroundings like a meerkat on the look for predators. I forced myself to walk slowly, look straight ahead, keep any internal monologue silent and not put my sunglasses back on until I left the mall.
I made it to my car with little attention from the other shoppers. In those few minutes, I was so happy to dress more freely than usual and so proud of myself for going through with this. I'd accomplished both objectives I had initially set.
I had conceived of a third objective on the way: to keep shopping in a skirt, but I didn't even remember it as I was leaving. Once I reached my car, it was too late to go back in. I drove home.
The outfit I wore as I left the store (minus the shoes) is attached, see "outfit1".
Once home, I went about cooking, eating and relaxing in front of the TV. Initially, I was really proud of myself (this was a victory over social anxiety), but after a while, I started feeling silly. I started thinking that, although people didn't react outwardly, a lot of them probably had a story to tell once home: "I saw a tall bearded guy in a Metal shirt and a skirt at the mall today".
Still, overall, I thought it had been a great day. Not many of those, so I savoured it.
A few days later, I started thinking I had another opportunity to accomplish the "bonus" third objective: the next friday (15/07/2022), after work, I would go back to a mall, this time much closer (but still over the border, to minimise chances to meet someone I knew), wearing a skirt from the start, and shop. I worked from home that day, so I wore my planned outfit all afternoon, ready to leave as soon as work concluded.
I had done a second pass on my leg epilation wednesday evening and temperatures had been rising all week, so I decided to not wear pantyhose. Went through quite a few skirt-and-T-shirt combinations, trying to select something that was neither too ostentatious nor too "grandma". I think I erred towards the former in the end. Since I'd be wearing a skirt all along, I had no reason to wear men's shoes, so I wore my pair of ballet flats. Unlike the first expedition, I needed a purse to carry my keys, documents (ID, driving license) and debit card this time (the one advantage of trousers over skirts: skirts rarely have pockets).
Work done, I hopped into my car and drove to the mall. I was more nervous than the previous time. This outing was definitely more daring than the prior one, for several reasons: I had no way of cancelling once I was in the mall, my skirt was shorter (and slightly shiny) and the chance of meeting people I knew, although still low, was higher. I don't know which of those reasons contributed the most to my increased anxiety, but there it was. So, I hesitated in my car for 5 minutes or more before taking the plunge. I left the car, walked through the parking lot and into the mall. As I'd done a week prior, I endeavoured to project confidence. I thought I was relatively succesful.
Again, I went from shop to shop. I overheard comments, all negative, but hushed. I caught glances. Salespeople were all professional, though. I had half-expected to be expelled from some shops, but was pleasantly surprised that they all either greeted me, ignored me or offered assistance.
As I was leaving a store, I noticed a woman filming towards my direction with her phone. Deliberately filming me, or was it incidental? I don't know. All I could and can hope is that the video didn't end up on some social media site. I kept shopping. Heard a man behind me shout "this one's for you" to his friend ahead of me. I don't know if he was jokingly referring to me or talking about something else entirely (an item in his hand?), as I didn't turn back to check. Most people did not visibly or audibly react, though.
In the end, I bought a satin nightie, at a significantly reduced price. The saleswoman made no comment on my outfit, but for once didn't go through the "gift bag and ticket without prices" charade. I eventually left, having spent an hour or so in a skirt in public.
Even with the slight negativity, I was elated at my trip. Pride and a sense of freedom dominated. A picture of that outfit is attached as well, see "outfit2", and "shoes" for the flats.
After eating, I was going to try my new nightie on (didn't dare try lingerie in a store), but found a sewing mistake. I had to go back to the store.
My window of opportunity was running out, so it'd have to be the next day (15/07/2022), in the morning. I wasn't completely annoyed at that prospect: I wanted to go back, this was a nifty excuse.
I quickly decided on another outfit (different skirt and shirt, same shoes) and planned for the next day before going to bed: I was going to try to take things even further, by going to street shops in a skirt. Scoped the wares online once more to see which shops were interesting. I don't know why I considered that more daring, the street is no more public than a mall, but I did.
The next morning (16/07/2022), I went back, more confident than the day prior. I was amused at the notion that the saleswoman would see me in a different skirt. No chalking it up to an occasional fancy this time. I exchanged the nightie (the saleswoman was again very professional), left the mall and headed for a commercial area of the city. Again, I hesitated in the parking lot, but eventually set out. I was in the street, in broad daylight, in a skirt!
I went to several shops, not finding much of interest.
I crossed a weekly market to go to another street. Here, I had my most negative reaction of the day: as I was walking by his stall, a man very loudly exclaimed "what is that?" in a clearly disapproving and angry tone. This time, it was obvious he was talking about me. My intention had been to ignore any negative reaction, but I reflexively turned my head to see who'd said that. He kept staring. His headgear identified him as a muslim and apparently he considered a man in a skirt to be "haram", even if that man harms no one and doesn't share his convictions. I walked on, shaken but undeterred.
I eventually ran into a small store that had pretty dresses, and took one into the changing room. It was too small, and the store only carried one of each dress, all of them in similar sizes, so no luck here.
As I was leaving, a woman asked me to grab a dress that was hanged too high for her reach. Not the first time I'm asked to grab items from high places, but that was the only real interaction with a non-salesperson of these trips, so I enjoyed it. She, apparently, didn't see me as a freak, or could overlook it.
I kept shopping, eventually buying some panties and pantyhose (advertised as "ladder-resistant", hopefully the reality matches the advertising), then went home. The outfit of that day is attached, as "outfit3".
Overall, I consider those outings a success. Sure, there'd been a few bad events, but I was able to keep the anxiety at bay (something I always struggle with) and a feeling of freedom dominated. Also, the breeze playing with my skirt as I was walking on the street felt very nice.
I really needed to share these events with other people, so here they are.
As for steps 2 and 3: step 2 involves a 2-week long vacation in which I plan on not even bringing any trousers, but it will only happen in roughly a year. I already know the destinations I plan to visit and events I plan to go and timetable I plan to follow, but I won't go into details at this juncture.
Step 3 involves slowly introducing my new look to people I know: family (beyond my parents), friends and colleagues (hoping the bosses have no objections), all that before my 40th preferably. Again, details can wait.
Will I go through with steps 2 and 3? Maybe not, but I'm going to try. It's worth it. I can't keep living just to meet other people's expectations, I have to start living for myself a bit.
Originally Posted by Heather76
