My Session in a Skirt & Heels

[JeffB]

Well, everybody, I've finally gone and done it! Thanks to folks like Unknown and Since-I-Can-Remember who intrigued me greatly with their photos, I've followed suit. I bought a skirt, and took pics of myself in them and a pair of heels. Below are two of the pics. You can see the rest if you visit my website:

Before you ask, yes, those are my legs, and yes, I'm wearing not just any skirt mind you, but a black leather mini. Not bad, eh? As for how this all came about, allow me to explain. It was curiosity that led me to wonder just what I'd look like in a skirt, something I've never worn before, and since I was indeing to post pics of myself in one, I decided early on to buy a short skirt so you (and I) could see what my legs look like.

A couple of days ago, I drove to an outlet mall just outside the city and went to a store that specializes in leather clothing since I bought a men's leather jacket there several years ago. I knew they sold discounted leather clothing and thought it'd be neat to wear a leather mini, if it was affordable. Turns out it was as I found the skirt you see above (size 20, I checked sizing charts before I left home) for a respectable $59.99 and figured that would suit my needs. The cashier never gave me so much as a second glance as she rang up my purchase.

Back at home, I surfed online versions of women's fashion magazines for the poses you see me in. I wanted the poses to look their best, so I printed out several examples and practiced the poses in front of a floor length mirror in my bedroom until I felt I had them down pat. Then I donned my L'eggs Resilience pantyhose in off-black, the skirt, my Renetti five inch heeled pumps in black patent, set up my camera and went to work taking the pictures. It took a wee bit of effort getting both sitting and standing poses just right, even after practicing.

After taking a good dozen pics (six each sitting and standing), I uploaded them to my computer and picked the best four from each category which I've put up on my Photobucket webpage. I must say that I had a good deal of fun, both taking the pics and, more importantly, wearing the skirt. This might be vanity talking, but I surprised myself with how damn good I looked in the skirt, how it perfectly accented my long, nylon clad legs and the pumps I wore with them. To the novice looking at these pics, I dare say my legs might well be mistaken for a woman's!

All in all, it was one hell of a unexpected thrill to wear a skirt for the very first time, even if it was indoors. Well, that's it, folks! Please let me know what you think!

[Shafted]

(wolf-whistle) Nice gams Jeff! So how do you think the skirt will go over at the office?

[Tommy]

I think you just made an important step again

[rxrenesis]

Nice set of leg & heels shots Jeff. I see a legs & heels challenge about to jump off.

[JeffB]

(wolf-whistle) Nice gams Jeff! So how do you think the skirt will go over at the office?

Heh! Not in this lifetime! :rofl:

Anyhoo, thanks for the compliments, guys! Like I said, wearing a skirt for the first time was fun, and I was genuinely surprised at how much I enjoyed the experience. I don't think I'll ever go out in public in a skirt (even I'm not that brave!), but I can certainly enjoy taking pics indoors dressed in one.

[Bubba136]

Great pictures. Skirt looks good on you.

[micha]

Heh! Not in this lifetime! :rofl:

Anyhoo, thanks for the compliments, guys! Like I said, wearing a skirt for the first time was fun, and I was genuinely surprised at how much I enjoyed the experience. I don't think I'll ever go out in public in a skirt (even I'm not that brave!), but I can certainly enjoy taking pics indoors dressed in one.

Hey JeffB,

now you are disappointing me! Wearing as a guy a leather skirt in the office - that's really a challenge. But on the street - why not?

Last year I have bought a blue jeans mini skirt. I couldn't help wearing it outdoors. With a nylon pantyhose and beige velours stiletto boots. Ok, I didn't dare this performance in my direct neighbourhood but it was a funny experience

Otherwise I never dared to appear on high heels at work. But for good reasons ...

[Dawn HH]

JeffB:-) Mickey says..."when she was your age she only wished she had had legs that looked that great". FANTASTIC!!! Dawn says..."I thought I have good looking legs in a skirt, hose & heels, but I think YOU have me beat".FANTASTIC ALSO!!! Please don't let this be the last time that you wear a skirt. why not have some more fun & excitement & take more pics & don't forget about us all. Cheers--- Mickey68 Dawn HH

[since-i-can-rem]

wow, that looks great! Jeff, I think you feel like me? >ou could fall in love with your own legs.....

[JeffB]

To bubba, micha, dawn & since: Thanks for the compliments. I'm glad you all found my pictures favorable as I honestly didn't know what to expect when I posted them. As for wearing a skirt in public, away from work, well, I try to never say never about anything, but it would take a whole lot of courage to do something like that. It would have to be just the right situation and the just right outfit to make something like that work. It might happen sometime in the future, then again, it might not. But, in the meantime, I'll gladly take more indoors pics in the future.

[unknown]

wow, that looks great!

Jeff, I think you feel like me? >ou could fall in love with your own legs.....

I can attest to this, if anything.

That skirt shot is immediately 1000x better than the rest of your gallery. Looks like there's no turning back-even if it stays at home.

I'm glad I can help be an inspiration, though.

[Thighbootguy]

WOW Jeff. Those poses look great and a leather skirt is the way to go. I have several leather skirts ranging from very short to ankle length, but I rarely wear any of them outside. I wear a 14 - 16 so I have been able to find them in thrift stores, usually for under $5. I really enjoy wearing them, but it’s not the image I’m ready to present in public. I understand what you said about wearing a skirt in public, “but it would take a whole lot of courage to do something like that” and have some agreement with that but it is really more about being comfortable with the image and enjoying presenting it. You wear heels to work and I wear thigh boots in public so I don’t think it’s a courage thing.

[Shafted]

Heh! Not in this lifetime! :rofl:

Anyhoo, thanks for the compliments, guys! Like I said, wearing a skirt for the first time was fun, and I was genuinely surprised at how much I enjoyed the experience. I don't think I'll ever go out in public in a skirt (even I'm not that brave!), but I can certainly enjoy taking pics indoors dressed in one.

Not to worry, neither would I.

[LuckyLad]

Very good effort Jeff. I know why you wanted to buy and try a skirt and it is really the only one way of properly showing off your heels. Hey, your happy, the worlds happy and no-one has died! Do what you want, when you want and how you want, life is just too short! - A bit like that skirt Nice one Jeff Lucky

[Bubba136]

Now, to find a nice blouse to go along with it....something with long sleeves, perhaps? As far as wearing the skirt to work, I would guess there is already an office pool on, since you are already wearing heels, hose and woman's underware, how long it will be before you appear in a dress or skirt and blouse......or, perhaps a nice woman's business suit. (Just kidding - but, wouldn't be surprised, either )

[Dawn HH]

JeffB:-) I can readily go along with what LuckyLad has said about life being short as some of us are on the low side and some of us are on the high side. One thing for sure...none of us know just how long we will be able to remain on this immortal coil, and we aren't supposed to know. So, there is just one thing for us all to do...enjoy wearing our heels as often as we can and as long as we can and I, for one, sure am trying. Isn't it just amazing how a pair of hose and heels can reshape ones legs? It sure has reshaped your legs and I'll say it again...you have a fabulous pair of legs of which none of us were aware of, not even you, because they were always hidden under pants. Now, since the cat is out of the bag...er...pants, let them forever shine in all of their glory. Congrats and enjoy, enjoy, enjoy!!! Cheers--- Dawn HH

[JeffB]

Thighbootguy: I've thought about what you said, and I think you're right. Perhaps it isn't a matter of courage, but the comfort level of the image itself. I don't see any men in skirts during the course of my travels, and it would be difficult to find an environment here in this city where I could safely wear one in public.

To everyone: Thanks for the compliments. Thinking back to my photography session, more than a few times, I found myself gazing at my reflection in the mirror and saying to myself: "Are those my legs? Wow!" To be honest, I never knew I could look that good in a short skirt! Needless to say, it was quite a revelation, and I enjoyed every single minute I wore that skirt!

To Bubba: Heh! I wouldn't know if there's a pool to determine if I'm gonna wear a skirt to the office, though it wouldn't surprise me if some of my co-workers wonder, even if just to themselves if I might well show up in one. To be honest, I have thought about swapping my men's dress pants for women's. If I can find the right inseam, given my height, I'd certainly do that!

[Bubba136]

Hey Jeff, as Confucius is credited with saying: "A journey of a thousand miles begins with a single step." So, first inseams and then seamed stockings.....what can I say....except isn't that the same path you traveled to wearing your 5" pumps at work ?

[WarrenB]

[dr1819]

Heh! Not in this lifetime! :rofl:

Anyhoo, thanks for the compliments, guys! Like I said, wearing a skirt for the first time was fun, and I was genuinely surprised at how much I enjoyed the experience. I don't think I'll ever go out in public in a skirt (even I'm not that brave!), but I can certainly enjoy taking pics indoors dressed in one.

Hmmm... I think how one goes about it might influence the effect.

There are three approaches:

1. Wear a skirt dressed as a woman.

2. Wear a skirt dressed as a woman from the waist down, like Dale Miller http://www.skirtman.org/cindex.html

3. Wear a skirt dressed as a man, except for the skirt. Usually, more masculine, gender-neutral, unisex skirts work well, here. One example is the Macabi skirt, worn by males and females alike, particularly on the trial, rafting, canoeing, cayaking, etc: Macabi Skirts for Men. Other skirts, like those from Menintime or Utilikilt, will also fit the bill.

I've worn skirts in public a few times, and usually find something that's nondescript, like a darker pair that's indistiguisable from shorts or pants, save for the single opening. Worn with flat sandals, the ankle-length skirts draw the least attention of all. People are actually quite used to seeing men in skirts, from movies, National Geographic, etc. The collective memory from ages past has not yet been lost from public memory.

What I haven't done is skirts and heels, as that simply communicates a visual message which goes against how I view myself.

[Danielinheels]

i really did make that face.

[JeffB]

Hey Jeff, as Confucius is credited with saying: "A journey of a thousand miles begins with a single step." So, first inseams and then seamed stockings.....what can I say....except isn't that the same path you traveled to wearing your 5" pumps at work ?

Quite true, bubba. I like that analogy you made. Three years ago, I never would've envisioned wearing five inchers in public. Who knows where I'll be three years from now!

Hmmm... I think how one goes about it might influence the effect.

There are three approaches:

1. Wear a skirt dressed as a woman.

2. Wear a skirt dressed as a woman from the waist down, like Dale Miller http://www.skirtman.org/cindex.html

3. Wear a skirt dressed as a man, except for the skirt. Usually, more masculine, gender-neutral, unisex skirts work well, here. One example is the Macabi skirt, worn by males and females alike, particularly on the trial, rafting, canoeing, cayaking, etc: Macabi Skirts for Men. Other skirts, like those from Menintime or Utilikilt, will also fit the bill.

I've been to Dale's website and even played the clip from the Sally show and I'm amazed at the strength of his conviction to wear skirts and heels full time in public. I'm sure he must've caught holy hell in the beginning, but he's doing what he loves, so more power to him. Your suggestions have merit, especially suggestion number two. For sure I'd never wear a skirt at the office as I treasure my job too much to risk losing it, but away from the office, well, who knows! Perhaps it would be wrong to say I'll never do it because there's no telling what the future may hold!

[Dawn HH]

WarrenB:-) NICE! Very nice. Great looking legs. Isn't it amazing? JeffB has just found out just how fabulous his legs look with a skirt. Cheers--- Dawn HH

[JeffB]

WarrenB:-)

NICE! Very nice. Great looking legs. Isn't it amazing? JeffB has just found out just how fabulous his legs look with a skirt.

Cheers---

Dawn HH

Well, it was quite an earth shaking revelation to discover that I do look good in a skirt. Something I honestly never thought was possible. And yes, I loved the feeling that came from wearing it. Suddenly, I'm eager to buy another skirt and take more pictures!

[rxrenesis]

Jeff, Go for it. A jean skirt is a nice addition to your collection. rx

[JeffB]

Jeff,

Go for it. A jean skirt is a nice addition to your collection.

rx

Not a bad idea, rx! I'm interested to see what other styles will look on me. However, I have this nagging feeling I'm only gonna want skirts that end above the knee so I can show off my legs!

:rofl:

[Dawn HH]

JeffB:-) Nice idea...go for other types of skirts, especially above the knee styles. With legs like that, I would want to show them off also. BTW...skirts look good with knee boots too. Hint, Hint!!! Cheers--- Dawn HH

[JeffB]

JeffB:-)

Nice idea...go for other types of skirts, especially above the knee styles. With legs like that, I would want to show them off also. BTW...skirts look good with knee boots too. Hint, Hint!!!

Cheers---

Dawn HH

Can't argue that, dawn! Anyway, I'll do some shopping for another skirt or two this weekend, then take more pictures. Crazy as this sounds, I have thought about going out in a skirt and heels of late, not to the office of course, but a non-work setting, maybe to a restaurant or something. It's hard to believe I'm contemplating such an action, and, to be perfectly honest, I don't know what's driving this sudden interest. Perhaps folks out there can offer a suggestion or two.

[Dawn HH]

JeffB:-) What's driving all of this? I call it Highheelitis. Wanting to explore all of the options available is of the essence. Once you have seen your legs in a skirt, hose and heels...that's very heady stuff for sure. Cheers--- Dawn HH

[JeffB]

JeffB:-)

What's driving all of this? I call it Highheelitis. Wanting to explore all of the options available is of the essence. Once you have seen your legs in a skirt, hose and heels...that's very heady stuff for sure.

Cheers---

Dawn HH

Thank you for the diagnosis, Dr. Dawn. Heh! And you hit the nail right on the head, this is most definitely heady stuff. I've found myself thinking a lot about wearing skirts ever since that photography session last week, about how good my legs looked in that mini and about future picture taking sessions as I have a goodly number of ideas in mind for new pics to take. I also think about how I wished I discovered this a long time ago, and about whether or not I could make wearing a skirt in public work, and where I could wear one. Yep, heady stuff indeed!