First Time Out in a Skirt

[JeffB1959]

To be honest, I didn't think I'd get to do this so soon after joining this board, but on Saturday, I finally took the BIG step by going out in a skirt. Below is the outfit I wore on my little adventure. Unfortunately, I forgot to pack my camera, otherwise, I'd have an outside shot to accompany this piece. Damn! Definitely next time.

Anyway, I headed out early on Saturday morning, say around 8 a.m. and drove to a downtown park that normally wasn't too crowded at that hour on a Saturday. Easily the hardest part of the entire exercise was getting up the courage to actually get out of the car, I don't mind admitting I was shaking and very nervous, no, let's call a spade a spade, I was scared stiff. Even though I used to be a crossdresser and ventured out in public dressed as a woman in daylight numerous times, this was wholly different, I didn't have a wig and makeup as a disguise to hide behind, I'd be exposed to the world, and that was quite unnerving to me.

It took a good ten minutes to get up the courage to finally get out of the car, put some coins in the meter and go about my little exercise of walking around the park so I'd be seen and see how passersby would react (Oh, before I forget, I had sunglasses on to hid my identity as best I could. yeah, I call that paranoia too!). Yes, I did get reactions as I wandered around, mostly in the way of turned heads and double takes from other pedestrians, heard a random giggle and someone saying in a hushed whisper, "Damn! He's wearing a skirt!" But I ignored it all and went about my business. I was still nervous, but didn't let it show.

After around fifteen minutes or so of walking, I sat down on a park bench and (keeping my legs together) pretended to take in the scenery while people passed by. Wearing the sunglasses enabled me to observe passersby without them knowing, I got more turned heads and stares here and there, but people also walked by without so much as a second glance, which was a good thing, if someone came up to me and asked why I was wearing a skirt, I don't think I could've responded properly as I was still nervous. After ten minutes on that bench, I decided I pushed my luck long enough and returned to me car and returned home.

All in all, it was an interesting and exhilirating experience, being out in a skirt, an experience that was both thrilling and a tad unnerving. I'm not sure I really relaxed the whole time, perhaps that led to people giving me the stares and whatnot, I don't know, but at least I did it. What do you think of my outing, folks?

[crfriend]

[...] Easily the hardest part of the entire exercise was getting up the courage to actually get out of the car, I don't mind admitting I was shaking and very nervous, no, let's call a spade a spade, I was scared stiff.

Well done, Jeff. Well done, indeed. You've just broadened your horizons a bit; the fear the first time is normal. but it eventually wears off. I was exceedingly nervous early on as well, but am now of the "Oh, so what, if you have a problem with what I'm wearing, it's just that -- your problem" crowd.

After around fifteen minutes or so of walking, I sat down on a park bench and (keeping my legs together) pretended to take in the scenery while people passed by.

Now, do precisely the same thing whilst wearing tr*users. See what sorts of behaviours you see around you. It may surprise you that most of them will be identical. You'll hear laughter, you'll hear an occasional odd comment and snippet of conversation, and everything else that's audible -- there's just one difference: you're now more aware of it.

Really, most folks just don't care, and those that do usually won't say "boo" to you.

[JeffB1959]

Well done, Jeff. Well done, indeed. You've just broadened your horizons a bit; the fear the first time is normal. but it eventually wears off. I was exceedingly nervous early on as well, but am now of the "Oh, so what, if you have a problem with what I'm wearing, it's just that -- your problem" crowd.

Yeah, the very first time is always the hardest. Even though I knew that going in when I went on my outing, getting out of the car was still quite a little struggle, fighting the omnipresent fear of the unknown since this was virgin territory for me, having absolutely no idea what to expect. However, you're right, the majority of people I encountered never paid me any attention, in a funny way, I was surprised that not everyone noticed me. But, now that I've got that first outing under my belt, and, having discovered that wearing a skirt as a guy in public wasn't nearly as terrifying as I thought, I can't wait to do it again!

[Kilty]

Well done, mate!!

Now I've plucked up the courage to put a pic on the site for the first time,
here's me in my new kilt.... I think the black look goes well...

Unfortunately, I've had to update my pic and disguise my face due to getting threats from people in my area. I ventured out in my kilt and a hooded youth threatened to stab me . After hurling abuse at me and calling me a 'battyman' I decided I won't be as brave as Jeff here...

My girl isnt so keen on me wearing it, even though I feel more relaxed in it. I told her its so things can B-R-E-A-T-H-E and of the health benefits but she's still unconvinced... (sigh)

kilty

[JeffB1959]

Yo, kilty!
Not bad, my friend! Not bad at all! Your look suits you as there's nothing wrong with basic black. Thumbs up to you!

[ChristopherJ]

Easily the hardest part of the entire exercise was getting up the courage to actually get out of the car,

I agree with that 100% Jeff. I am scared/nervous/terrified . . . whatever - every time that I go out in a skirt - just as it come to getting out of the car. As I am more used to it now, it literally only lasts 5 seconds - and then I'm off down the street - wearing a skirt and feeling very relaxed about it. It gets a bit easier every time.

Sunglasses are definitely a good idea - while you build up your confidence. One of my defences to start off with was to carry a camera - as i thought that people would think that I was an eccentric arty type . . . . Oh dear - I'm giggling at my own idiocy as I type that. But we all have to find our own way with this - and that was how I did it the first few times out. Also, I have found that it is best to be bold - i.e. not to sort of sulk about in the corner as if you are doing something shameful, but to be very upfront about who you are and what you are wearing. I find people seem more accepting of me then.

Good luck for next time!

Kilty -

Thanks for posting that photo.

I think you look great in that outfit. I like the kilt very much - and I don't wear them. That is just the right length for you - in my opinion - and the whole outfit looks very well balanced.

[JeffB1959]

I agree with that 100% Jeff. I am scared/nervous/terrified . . . whatever - every time that I go out in a skirt - just as it come to getting out of the car. As I am more used to it now, it literally only lasts 5 seconds - and then I'm off down the street - wearing a skirt and feeling very relaxed about it. It gets a bit easier every time.

Sunglasses are definitely a good idea - while you build up your confidence. One of my defences to start off with was to carry a camera - as i thought that people would think that I was an eccentric arty type . . . . Oh dear - I'm giggling at my own idiocy as I type that. But we all have to find our own way with this - and that was how I did it the first few times out. Also, I have found that it is best to be bold - i.e. not to sort of sulk about in the corner as if you are doing something shameful, but to be very upfront about who you are and what you are wearing. I find people seem more accepting of me then.

Thanks for the comments. When I think back on Saturday's little outing, words fail to describe just how petrified I was while I sat in the car, trying to build up the nerve to get out, but I managed, and the rest was history, and it turned into quite an experience. A question: did you wear a miniskirt on your very first outing, or something more conservative like I did? I would agree that being bold is the way to go, show the world that you're not afraid to wear what you like and what you feel comfortable in, not to mention being comfortable in your own skin. Already, I'm planning my next outing as I'm eager to go out in a skirt again. Hopefully, I won't be so nervous and I can actually enjoy my outing! Heh!

[sapphire]

Jeff & Kilty,
Yotionsu both look great! Kilty, the basic black combo works well for you and the line of the outfit compliements your body type very well.

Jeff, a big congratulations for your outdoor excursion.
Diana

[ChristopherJ]

A question: did you wear a miniskirt on your very first outing, or something more conservative like I did?

Yes - I wore a mini skirt on my first outing. In fact, this was the outfit:

http://farm1.static.flickr.com/115/3134 ... 58.jpg?v=0

Dig the legwarmers! (cringes in embarassment) I don't wear that particular pair anymore, but I like legwarmers with short skirts.
And the tights! I had forgotten those. I had a pair of 13 year-old girls come up to me and say that they really liked my tights. I'm still not sure if that was a good thing or bad thing . . .

I was perfectly happy to wear a short skirt on my first outing around town as - IN MY MIND - short skirts look less 'feminine' than longer skirts. This is entirely my own view, but as a result I feel far more comfortable in a short skirt than I do in a knee length one. Weird - isn't it? But we all need to go with what we are comfortable with.

[dragonfly63]

You Look Great!

[JeffB1959]

A question: did you wear a miniskirt on your very first outing, or something more conservative like I did?

Yes - I wore a mini skirt on my first outing. In fact, this was the outfit:

http://farm1.static.flickr.com/115/3134 ... 58.jpg?v=0

Dig the legwarmers! (cringes in embarassment) I don't wear that particular pair anymore, but I like legwarmers with short skirts.
And the tights! I had forgotten those. I had a pair of 13 year-old girls come up to me and say that they really liked my tights. I'm still not sure if that was a good thing or bad thing . . .

I was perfectly happy to wear a short skirt on my first outing around town as - IN MY MIND - short skirts look less 'feminine' than longer skirts. This is entirely my own view, but as a result I feel far more comfortable in a short skirt than I do in a knee length one. Weird - isn't it? But we all need to go with what we are comfortable with.

Well, color me greatly impressed! That pic was mighty impressive, even though the legwarmers psoitively screamed "1980's"! Heh! Still, I admire you for the courage of your convictions by going out and about in a miniskirt. And I agree, we all have to comfortable with ourselves and do what works best for each other. I don't know if I could go out in a mini, but I'll keep that in mind for a future outing. Many thanks for sharing that cool pic!