My Session in a Skirt & Heels

[tightlevisandhhboots]

It's been a long time since I visited the site, but I saw this Jeff and had to comment....WOW!!!! For those that remember, I am the guy in the US military that likes to wear hhboots. My every day pair are 3 1/2" heeled cowboy boots. I also have a pair of 4" block heel boots. But I wanted to let you know Jeff, that I jsut got back from a trip to Alaska, that I wore my camouflage Utilikilt through three airports, and didn't get a single negative comment. In fact on my return trip, while waiting for my luggage to arrive at the baggage claim, several people came up and commented "It sure is great to be back in Seattle and to see those Utilikilts again" and wanted to know where I had been etc... Anyway I got comments rangine from "is that a new Military Uniform" to "Is that a REAL kilt" or "I've never seen a camo kilt!" But all very friendly. Of course I was only wearing sandles, and not heals, but it was fun none the less. What I did learn, was that you will never lack conversation when wearing anything "non-traditional" in public, especially at the air-port. Cheers, tightlevisandhhboots

[JeffB]

Hello, tightlevisandhhboots! Thanks for the kind compliment. I had no idea that pics of me in a short skirt and heels would go over so well with the folks here. Imagine that! Heh! Anyhoo, your travel adventure home from Alaska in that utilikilt was pretty darn bold! More power to you, my friend! And yeah, conversation about things outside "the norm" is always fun!

[Dawn HH]

Tightlevisandhhboots:-) It is good to have you back and posting with us again. Now since JeffB has broke the ice and caused you to post again...stay with us and keep on posting. Yes...and those pics that JeffB took of himself in a skirt, hose and heels really opened his eyes to the fact that he had been hidding an extremely fantastic set of legs under his long pants far too long. It also opened our eyes to the fact that if you didn't read the name of the person posting...you would have thought it was a woman after looking at those legs. OUTSTANDING!!! Cheers--- Dawn HH

[tightlevisandhhboots]

Thanks Jeff and Dawn! I have been quite busy with the military and family life, so haven't had alot of computer time over the last many months, but I just stopped in to see what was happening, and saw Jeffs pic!! I really like to wear my Utilikilt alot, as it really is very comfortable and starts a discussion where-ever I go wearing it. The only thing is that it is not as heavy as my traditional kilt and if the wind is blowing, it can turn into a kite and show what or what not you are wearing... I'll try to get on a little more as I won't deply now till the first of the year. Thanks again, tightlevisandhhboots

[JeffB]

You flatter me, Dawn! Thanks for the compliments! And yeah, those pics I took were quite the revelation. I had great looking legs and didn't even know it! HA! Anyhoo, more pics will be coming soon! No way will I hide my light under a bushel basket!

[Dawn HH]

JeffB:-) I'm up to more of your pics any time. Bring them on. Cheers--- Dawn HH

[Bubba136]

Me too. I agree with Dawn!

[JeffB]

Well, then I'll just have to do my best to accomodate you all. I had no idea my legs had become so popular here! HA!

:rofl:

[Jamie001]

Jeff, WOW! You really have great legs! They look like girl's legs and are really pretty with the pantyhose, skirt, and heels. Most girls would be envious of your legs. You really should wear the skirt, pantyhose, and heels to work. I am sure that you will get many compliments. Regards, jamie :0)

[luxxyheels]

You look nice Jeff .

[dr1819]

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!

Or just take a stroll...

[Skirted-UK]

Jeff I have to warn you that skirts can be very addictive! When I was at school in the fifties I was fascinated by the school secretary's long straight black skirt. when I left school I bought one just to see what they were like to wear. I have been unable to get out of them ever since. Over the years I have properly worn more straight skirts than most women. I started with skirts first, then got some heels to go with them, you have done it the other way around!

[rxrenesis]

Jeff,

Welcome to the skirt & heels club. I dug into the archive and came up with a few of my skirt & heel shots.

My 1st try a making a skirt from a pair of shorts.

What ya think?

rx

[Dawn HH]

Skirted-UK:-) I very well know what you mean by skirts becoming additive. I enjoy wearing mine very much and they are quite comfortable. Rxrenesis:-) You look good in a skirt and heels. Do you have any more pics for us? Cheers--- Dawn HH

[dr1819]

I hear you, Dawn. I am by no means effeminate! In fact, I present more like a rough and tumble kind of guy. But I've really grown fond of wearing ankle-length skirts around the house, usually with my 3-1/2" clogs, or on colder days, my hheeled boots. I wear skirts occasionally in public, but not normally. A skirt just stands out too much, where as many heels are easy to hide under long pants.

[JeffB]

rxrenesis: Well done, my friend! Your pictures looked pretty darn good! Your attempt at transforming shorts into a skirt wasn't too bad at all. I seriously doubt I could do anything like that! So I'd have to settle for buying from a store! HA! Skirted-UK: Yeah! I agree that skirts can be addictive as I've been thinking a lot of late about where I can safely wear one in public, something that's intrigued me greatly ever since I took those pics. I've been thinking that with just the right sort of outfit in the right setting, it could work. luxxyheels & Jamie001: Thanks much for the compliments!

[Skirted-UK]

Jeff, If you want to wear a skirt out, do it at night at an isolated location. Drive out into the country and go somewhere that's not lit and were you cannot be surprised by vehicles. Get yourself a long woman's raincoat in a dark colour and a headscarf to cover your head. If you come across someone in the dark, all they will see is someone in a long coat, wearing a headscarf and automatically think it's a woman. Always wear black or dark navy, it makes you look smaller and merges into the darkness. Don't wear short skirts, they stand out and attract attention. Long slim ankle length skirts are best, at night its difficult to discriminate between a long slim black skirt and black trousers. Leave home in something unisex, like a black turtle neck sweater and tracksuit bottoms, take your skirt and heels in a bag. Its easy then to swoop clothes when you get to your location. Enjoy!

[JeffB]

Those are some interesting suggestions you made, Skirted. Sounds like you put a lot of thought into your ideas. It would be rather fun to give this a try down the road, just to see what would happen.

[Skirted-UK]

Jeff,

If you want to wear a skirt out, do it at night at an isolated location. Drive out into the country and go somewhere that's not lit and were you cannot be surprised by vehicles.

Get yourself a long woman's raincoat in a dark colour and a headscarf to cover your head. If you come across someone in the dark, all they will see is someone in a long coat, wearing a headscarf and automatically think it's a woman.

Always wear black or dark navy, it makes you look smaller and merges into the darkness. Don't wear short skirts, they stand out and attract attention. Long slim ankle length skirts are best, at night its difficult to discriminate between a long slim black skirt and black trousers.

Leave home in something unisex, like a black turtle neck sweater and tracksuit bottoms, take your skirt and heels in a bag. Its easy then to swoop clothes when you get to your location.

Enjoy!

Its a well tried and practiced operation. But do leave the car a long way from were you are going to wear your skirt as cars attract cops. I use a bicycle.

[jim]

Well I gotta say that your skirt wearing trips are just about as clandestine and perhaps even more organised then some OP's I've been on! :rofl: Hey Jeff... Just to be doubly sure no one sees you in a skirt, you could always HALO into your preferred AO at O-Dark-Thirty and then a 3 man extraction team could pick you up by Zodiac at some prearanged coastal RV point when you're done. PS....dont forget to remove all the tags from your clothing and if captured, we here on the board will disavow all knowledge of your mission. jim

[Dawn HH]

WOW, Jim!!! Were you once a special ops man? This message will self destruct in 5 seconds. TEE! HEE! Cheers--- Dawn HH

[JeffB]

Well I gotta say that your skirt wearing trips are just about as clandestine and perhaps even more organised then some OP's I've been on! :rofl:

Hey Jeff...

Just to be doubly sure no one sees you in a skirt, you could always HALO into your preferred AO at O-Dark-Thirty and then a 3 man extraction team could pick you up by Zodiac at some prearanged coastal RV point when you're done.

PS....dont forget to remove all the tags from your clothing and if captured, we here on the board will disavow all knowledge of your mission.

jim

Yo, Jim! You wanna know what's scary about what you said? I understood you perfectly! I was in the military (Navy), so I'm up on all that Spec Op lingo! Ahh! the memories!

:rofl:

[Bubba136]

pick you up by Zodiac at some prearanged coastal RV point

And get those thighboots, striking high heels and leather skirt wet?

Whaaaaaaaaats wrong with you man? A high altitude baloon extraction, using a specially modified C-130 would be easier on the clothes. :rofl:

[jim]

Were you once a special ops man?

Dunno 'bout any of that stuff ....( but I was a Boy Scout once and durring summer camp we would do "panty raids" on the girls dorm, so dose that count?)

Whaaaaaaaaats wrong with you man?

Well douse me with a bucket of prop-wash and slap me up-side the head!

What the hell was I thinking Bubba !

Saltwater dose play havock on leather and I should have known better than to have even suggested such a thing.Your method of extracting the skirt wearer would be, as you say "far easier on the clothes" even if a tad riskier to the wearer.

If JeffB decides to run with your suggestion, I do beleave a large diaper and a 6 pack of TP would be handy things to bring.

jim

[Skirted-UK]

Jim You may well jest, but you have to plan for the unexpected. About 7 years ago I bought some 3" block heel pumps to wear in the country. That week I was doing a job at the other end of the county and had to come back over the moors in the evening. I thought it would be a good idea to take the pumps and a skirt and try them out. On the way back I stopped by a lake and hid the van off the road so that nobody would see it. (or so I thought) I changed out of my Jeans about 100 yards from the van and hid them in the bushes. I started up the track, wearing a black turtle neck sweater and a long straight black skirt, with my new 3" pumps. When I got to the top of the hill overlooking the lake I was surprised to see in the moonlight, that the Park Ranger's Land Rover was parked in the car park and he was looking around my van with a torch. No problem I thought, I will wait until he has gone, then I will go back and change. But after half an hour he is still there and the Police have now turned up and start looking around with powerful lamps. Fearing the imminent arrival of the Police helo, complete with thermal imaging camera I decide to make a fast exit and head for the woods in the valley below, putting as much distance between myself and my van as possible. I am now not very happy, as stumbling around in the woods in the dark, in a tight skirt and high heels is not part of my master plan. I got about a mile up the valley before I had to repeat the whole journey and retrace my steps. When I got back to the top of the hill, the Police had gone, but the Park ranger's Land Rover was still there! I had now been stumbling around the moors in high heels and a straight skirt for over 2 hours and the novelty was starting to wear off! It was 2 O'clock in the morning before the Ranger finally left and I was able to change and go home. But that was not the end of it. The next day the Police phoned my Boss and wanted to know what the Van was doing there at night. Apparently the Park Ranger thought that I was poaching fish in the Lake!! I had to come up with a Cock & Bull story that I went for a walk to freshen up after a long drive and got lost in the mist. All the blokes at work thought it was hilarious! Now had I thought it through before I started, I would have left my jeans somewhere were I could have got to them when the ranger turned, changed and walked back if nothing had happened. So you see, you need to plan these things! Hmm, a 3 man extraction team in a Zodiac. Damn, why didn't I think of that!

[jim]

That’s quite a predicament you were in Skirted and understand your need to plan. I also fully appreciate the fear and apprehension you were experiencing at the time. As you say,if the cops had brought in a FLIR unit you would have been screwed for sure but so would breaking your ankle and being medivaced out by helicopter. Brother… would that have made the papers or what. I'm glad to hear the situation resolved it's self tho and did so with out you being "sprung". Most here know how powerful the desire to wear heels is, but I feel it should be a gratifying low impact pass time not an extreme, hi risk body wrecking sport akin to mountaineering and bungee jumping... In saying all that..I wish you good luck with your skirting. Jim

[Shafted]

Skirted, Your story is a classic example of the nature of a clandestine outing, and is exactly why I would recommend heeling in plain sight. It's a lot more embarrasing if you're doing it in secret and get caught, than if you're doing it confidently for all the world to see.

[Skirted-UK]

Skirted,

Your story is a classic example of the nature of a clandestine outing, and is exactly why I would recommend heeling in plain sight. It's a lot more embarrasing if you're doing it in secret and get caught, than if you're doing it confidently for all the world to see.

Unfortunatly I have yet to get my head around that!

[Dawn HH]

Jim:-) Panty raids? Now that sounds interesting and they should count, I would think. When was the last time that you were on one? I don't think that I could handle a panty raid these days. Those girls get pretty heavy when you have to run with them over your shoulder. TEE! HEE! Skirted-UK:-0 Wow! What an adventure you had. Even with planning, you still run into problems. I'm inclined to go along with what Shafted says and stick to daylight heeling in the towns and malls. Cheers--- Dawn HH

[Skirted-UK]

Jim:-)

Skirted-UK:-0

Wow! What an adventure you had. Even with planning, you still run into problems. I'm inclined to go along with what Shafted says and stick to daylight heeling in the towns and malls.

Cheers---

Dawn HH

That might be ok in the States, but here in the UK we have a problem with Drunken yobs looking to start trouble.. It's also set to get worse in the coming months with the introduction of 24 hour drinking.