SkirtDude

That is such a sexy skirt ♡♥♡ great ensemble and I love the shoes. Your confidence amazes me, even now I am still getting used to skirted jaunts, even in just a simple pencil skirt, or a regular denim knee length one. I wish I didnt give a damn and could block out those stares... its like they sometimes burn thru my soul... still you pull off this look so well! Looking forward to tomorrow's jaunt

Looking great! I wouldn't have the confidence to wear something so short, but you pull it off well, hon ★★★

You're smiling in your 3rd pic! You've got a cute smile and I looove those glases ♥♥♥ You have confidence and style, looking forward to your next jaunt

Looking great Jeff! Love this beige skirt! Really suits your complexion too. You're a snappy dresser ♥♥♥

JeffB,   Like many others I've been following your jaunts. Lead on.   I just couldn't put my finger on what it was about your pictures that bothered me, but I finally got it. Dude, you need to smile. Look like you're enjoying it as much as I think you are. You're probably just thinking about the blinking self-timer, but your expression says "YOU GOT A PROBLEM WITH THAT?!?"  

Don't read into it too much, ALL black women have that face... that is their smile or all they'll give you if they're in a good mood Looking forward to 200

@KiLty, No problem! I have a thick skin and wasn't at all miffed about what you said. All is forgiven. And I DID get your name right this time! Best, Steve

no worries I want to change my username as I'm now living full time as a woman :shock: No to be serious wanted something easy to remember me by as kilty does look a bit lame... (Jeff, thanks for letting me and Steve squat on your thread)

Jeff, looking good! You inspired me to perhaps try again... I put on a simple grey skirt and peep toe wedges and went for a walk up the road.. I didnt give a shit what people thought, I think the fear must be confronted. I may do some outings again soon, but in the meantime am looking forward to your 200th jaunt... @Steve, sorry I was a bit of a b*tch to you earlier... I want to change my username as it doesn't reflect the true me...

Kitty, I'm not going to try to convince you to keep wearing heels or skirts, but I do want to point out that it was something you set out to try to do, and if you give up, then the demons (in your head) win. That is not the outcome you wanted, nor does it have to be that way. Your destiny is still very much in your control.Steve

It looks like this heeling lark will be expensive, and if some aren't supportive of me on the forum, what hope do I have of convincing Joe Public about fashion freedom? Remarks like saying I'm 'giving up' doesn't help. I fit in better with kilt forums, what interest I had in heels has been killed off by 'suggestions' which seem more like thinly veiled criticism.I'm done.BTW for the final time my name is NOT Kitty.

.

I think i'll take it on board and blend in with what I observe local girls wearing - jeans and trainers it is then

I dont want to be that weirdo in the park, or anywhere else, so thats helped me decide heeling perhaps isnt my thing. Even the skirts is taking me outside my comfort zone to cross dressing. The Mrs isnt happy with it either, so I think my jaunting days are over for the coreseeable future. I want my family to be happy and that comes before anything else.

Those of you who are able to heel I admire your courage. There can only be one JeffB, I dont want to be a cheap imitation... ♥♡♥

I will observe from the sidelines for now. That run in was too much for me

Too bad.

Too sad,

for the lad,

who was had

by a cad

who was mad

at the fad

that's somwhat rad

to make him glad

to retreat to his pad.

Cool poem! I will show it to my counsellor today after I booked a session to cope with my trauma of yesterday's events...

Errr... Am I missing something? Heels were not worn during this 'adventure'.

Just to put your mind at rest, on my next brief outing early this morning to the same park (it was daylight this time, lol) I thought I'd try something a little more out of my comfort zone. Strappy heels! Teamed with a polo shirt and black pencil skirt (this one was different from my others, instead of a slit at the back, there was a large kick pleat, it almost looked kiltlike

I thought all black ensemble would look okay...

it was quite snug, but I thought I'd try a casual walk, as if I was wearing shorts. So out of the car and off I went, and I saw a girl jogging, she glanced at me, I smiled, she smiled back! That was a surprise. I continued on, and saw a park bench and thought I'd have a breather, and so I sat, legs crossed, and looked on eBay for the next bargain... I was rudely awoken from my browsing by a West Indian woman, in her 20's, calling me a 'chi-chi man' and she started hollering at the top of her voice. She was calling to a friend to come and take a look. Not wanting to appear on the next Twitpic or Instagram, I beat a hasty retreat (as demurely as one can walk quick in a pencil skirt and heels!) for the safety of my car. Once back home, my heart was still pounding, I'm not sure I'm up to getting verbal abuse just yet, and to make matters worse, my feet were killing me... I think somehow I can get away with the denim equivalent a lot better, unless this was a one off bad experience. I think heels are too uncomfortable for me, so I don't know how many outings I will participate. Heeling did interest me, but it's a world away from the kilt forums I've been on, and the nearest alternative (skirtcafe, filled with bigoted old codgers in unflattering clothes) didn't bear thinking about...

Jeff, don't bother with wool-knit versions of the pencil skirt, they stretch out and lose shape... regular tailored ones look good, with a decent split at the back for movement Looking forward to your next jaunt, I'll get off your thread now

Thanks guys! I'll see what I can do when it comes to my outings, I have to get my breath back from yesterday's excitement!

Kilty, I was just having fun..... I love the "British English," some would argue, the real English. Last week I was at Pebble Beach and a gentleman with a very heavy British accent axed me where the "car park" was. I smiled, looked puzzled and axed him what a "car park" was, then started laughing. He then said, "parking lot." We all laughed, he made comment about American English being different, and I sent him on his way to the "car park."

Back to topic, I don't wear skirts - only gals shoes - how strange - ha ha. Have fun in you outings!!! sf

It's nice the variety in fashion, if you do a Twitter search on 'man skirt', it seems we're not the only ones heeling or pushing the envelope when it comes to fashion freedom. The whole UK English and US English is a strange one... I didn't want you thinking I was going to a 'chemist' to pick up some crack cocaine in a bad part of town (South London), lol

Are you sure your location is in the UK? LOL

Yes we have a lot of American members but this is a UK based site and so you don't need to try so much to be so "transatlantic"

You will be surprised, no shocked, by how accepting neighbours can be!

Blimey! I never knew it was a UK site... I didn't want to patronise our neighbours across the Pond... I'll talk about usual stuff like 'rubbish', 'Tesco', 'skip' then... BTW I love your avatar, you've gotta tell me where you got that gorgeous skirt I'm in London, what part of the UK are you from? Sorry my pics come out sideways, it's something to do with the camera on my tablet when I typed the first post...

'

To me this outing is identical to someone's first outing in heels, the feelings and fears are all the same. If one can go out in a black denim pencil skirt then one can go out in heels, the two are interchangeable. Moreover, I would say that you either wear heels or a skirt, wearing both, especially for a first outing, is just too much for anybody IMO.

In a dark park at night the last people you fear are the police, they are less likey to demand an explaination for the way you're dressed."

Thanks for the kind words and support. I was even going out of my comfort zone being dressed the way I was at night, my outfit was cute, but any pervert could have been lurking in the park when I had to pee. I won't take such risks, and will heel in the street.. that's right @euchrid, heel and I thought I would tidy myself up before posting another possible outfit... these shoes are a struggle to walk in, I'm as graceful as a newborn cow in these...

One day, I may try teaming a pair of jeans with heels, but my figure is good in a skirt or kilt...

Sorry for the dull 'selfie', (all my flat is magnolia, landlords love it) I didn't do a whole body shot, but I was thinking of this pinstripe skirt and the heels, though it's really pushing the envelope for me, I may wear it on my next jaunt...

I think you're reacting out of context. Euchrid's remark was in response to Foxyheels's post from what I can see.

ok.

Errr... Am I missing something? Heels were not worn during this 'adventure'.

I made up for that by wearing a pair of boots when I met my neighbor... the boots I was planning to wear, a smart pair of brown ones, need re heeling, so I just went in sneakers. We all have to start somewhere, put the gun down and chill out. I didn't realise I would get heckled for this, its put me off the whole thing. When I've worn sneakers with kilts, I have never faced any problem. I know its High Heel Place, but in the context of trendsetters like Jeff, I can change my footwear now and then, surely? Show some ♥

Its a good idea for a thread, yesterday's brief excursion was so nerve wracking for me. It will get easier I know. I'm in a dark blue pleated skirt today, its very comfy, but a little floaty as its a 22 inch. I went to put the trash out this morning and didn't realise as I got to the dumpster a gust of wind caught the back and was worried my neighbor could have caught a view which horrified me... I pulled down the back and tried to style it out like nothing happened. He said he liked my skirt which was a surprise, it definitely wasn't a kilt as it was pleated all the way round, but it did have a tartan check. We then had a chat about cars for five minutes... perhaps this anxiety thing is a waste of time. It seems as much a non event than if I was in a kilt or even jeans. Thankfully he said nothing about the 'wardrobe malfunction'... floatty short skirts take some getting used to... I was wearing my black boots with small heel, though the neighbor said nothing about those either

A pharmacy, not a chemist like Samuel L Jackson in disastrous movie Formula 51... I'm not off to a good start if all thats remembered is a lesson in British English :sigh: Hopefully the nerves will get easier if I get out there more... I'm in two minds as I worry about the time my journeys will take up, and have a major project at work to complete so we'll have to follow JeffB gor now.,.

As suggested I should try my own thread... so here goes... I needed to get some medication from the chemist, there is a 24 hour one so I set out... I was nervous, but I am still seeing if this jaunt lark is for me... Dressed in one of JeffB's favorites, I donned a black polo shirt, my new 23" black denim pencil skirt and sneakers (in case I have to run from anything like my fears, lol)... I walked to my car, a pair of guys passed me, I noticed their conversation stopped... nevertheless I opened my door, put my booty in, smoothed the back of my skirt, kept my legs together and swung them in and set off. Heart was beating like it would explode but as many say there is nothing to fear except fear itself... I abandoned my trip across town, my nerve went, but stopped at a country park and went for a short walk... I shouldnt have drunk a large bottle of coke, nature was calling. I was scared as I was in a park (not a soul about, but didn't like the idea of cops appearing from nowhere) as I had to crouch near a bush, hitch up my skirt and take care of business... I felt exposed. I will have to not get in such a predicament. From there I headed to a supermarket, and was going to buy something, but the security guard gave me such a dirty look, I thought I would call it a night... I dont know if you can add pics from the mobile app, but I took a couple of me on my way in the car, and walking (briskly) down the street... and in the park... I tried a "selfie" but it was too dark... Kilty Heres a pic...

_{Okay, I get the hint, you don't want me around anymore (runs out of room sobbing) I may start my own thread, though it won't be as good as yours... BTW I did wear that cardigan as it was a lot cooler yesterday... it was raining too, but I was indoors for most of my trip to the mall}

(blushes) Thanks so much for the kind words, Shafted and JeffB... ...

hey just a little disclaimer (I won't delete the pics) but the control slip had some sort of "bottom uplift" panelling on it which made it look like I've got granny panties on as well as being too hard to move around in if worn at knee length. Unless I'm wearing it wrong, I was surprised it was so tight even for a size 8 I can at a push fit into a size 8 skirt though I'm usually a 10 (heading to 12 and need to diet), and in regular jeans a 34. I went on my first real long public outing to a large out of town shopping centre (Lakeside) yesterday, wearing my cardigan teamed with a short navy pencil skirt, though I wore different shoes... I tried pop sox and trainers, like what a girl would wear to the office before popping on her heels... I was aiming for a casual look,though I think the look may have backfired... I felt very exposed and the skirt rode up a little, and I had to keep pulling it down every so often

though sceptical at first I know proper underwear does make a difference and makes things look a lot more presentable than before. I didn't bother with a slip on such a warm day. My heart was pounding as I left the car and went inside the mall - a group of teenagers passed me, looked, but said nothing. I walked around for 20 minutes or so, went to an ATM to take some money out, but had to answer the call of nature. I need advice from skirted members here as I felt a bit out of my comfort zone. Had I been in a kilt, I would have walked into the men's, but this time I went in the disabled toilet at McDonalds after ordering a takeaway... It's the whole skirt up panties down sit and pee stuff I'm still adjusting to (sorry for the graphic picture, but I can't think of the best way to explain)... In a kilt I don't feel as worried as kilts although uncommon are seen as just smart menswear... do most of you guys when skirted just say to hell with it and use the men's and find a stall? I just was very anxious. I bottled out of buying a dress in one shop, was worried about asking to try it on as I didn't want to upset any ladies using the changing rooms (it was busy), though the sales assistant, despite the confused look on her face was very helpful. I think I'll stick to eBay for now... Once back home, I was glad I pushed myself out there, but I'll never have the same confidence as JeffB does, or some of our more experienced members...

Does this anxiety subside after a while? Oh, and one other thing - is there a short window of time which after a while we cannot edit posts or amend them? I tried to amend something recently and couldn't. Jeff, sorry for hijacking your thread, I just thought I'd share my first jaunt if I may use the word, with you

Kilty: By all means, let me know what happens with the brief and how it works with that beige skirt. I agree wholeheartedly with what you said about skirts being comfortable, especially on hot, humid summer days, I feel so much cooler, even moreso than when wearing men's shorts. I've mentioned this more than once, but I almost never wear men's shorts beyond my front porch or to a store around the corner because I don't feel at ease in them, not even knee length cargo shorts, but I've worn skirts as short as 15 inches everywhere without a care in the world. As for a jaunt in a knit pencil skirt, that will be coming soon.

Jeff, I got my briefs and control slip today, but I ordered the wrong size I'm at least a size 12 in these, the 8 shipped is too difficult to move in (let alone pull up quick enough when nature calls) so I'll save it for cold winter days... it can stretch to knee length but that made me shuffle around like Kim Kardashian so I wear it at the length you see in the pics...

wheras the briefs kept my cargo.... er... secure

I feel so self conscious in that beige skirt now (and its a magnet for dirt, smh) that I don't wear it out much...

but I've got a nice grey one

You'll have to show us your new pencil skirt and tell us of your latest jaunt....

that shows what a good job the underwear now does... I didn't realise so much is needed for this Fashion Freedom carry on