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JeffB

The Jaunts of JeffB!

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Bootking: Well, I'm sure that kid will think twice before being so silly! Heh! Meanwhile, it'd be cool to meet you if you make it to PA! Maximilian: Thanks for the kind words. I simply do the very best I can. Mustering the courage to go out in heels in an ongoing process for me, it's not something I can call up at the drop of a hat, each and every time I go on an outing, I have to summon that courage which often takes more than a few minutes before I hop out of the car and go out. However, once I do, suddenly, I feel good about myself and comfortable and whatever fears and/or nervousness I happen to have disappears and I have nothing but fun on my little adventures. I'm glad to be an inspiration to others and that they take cues from me and what I do on my outings.

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JeffB you are also an inspiration to me!! I understand what you say and what you feel when you need to take the courage to go out from the car. But after the first second you stand on heels, you are sure that is that you want to do and you start to walk proud and firmly, cli-cloe, cli-cloe

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JeffB:-) Very exciting and interesting stories. Can't wait to read the next chapter in the saga of JeffB out in public with heels and a skirt on. Cheers--- Dawn HH

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Jeff B ... Thanks for all of your posts. Your experiences inspire me to go to many different places wearing high heels. Keep up the great work and keep the posts coming.

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my6heels, Stilettoscot & roniheels: Words can't describe how happy I was to have read that my exploits have been a source of inspiration to you all. Hopefully, you'll be blazing trails in the future for newbies here who will draw inspiration from you like you did from me. Pay it forward, friends, pay it forward! :w00t2:

Dawn HH: Well, that outing in heels and a skirt IS coming! I see that as the last frontier in my ongoing exploration in fashion freedom, something I've been eager to do for some time now as I've been building up my courage to take this ultimate step. I'll be sure to let everyone here know how it all works out.

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Go, Jeff, Go. An inspiration to us all. Cheers--- Dawn HH

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12/13/2008:

Well, guys, I did it today! I finally did it! I went on an outing wearing heels....AND A SKIRT!! Below is my outfit:

Posted Image

Posted Image

If you were expecting something risque, like, say, a short skirt, sorry to disappoint, but that wasn't happening as I sported a sedate outfit consisting of one of my favorite wintertime sweaters, a calf length, A-line denim skirt from Sears and Payless "Tara" boots. For starters, it was pretty darn cold out today as the mercury never saw the high side of 35, so I wanted to dress warmly for what was a spur of the moment outing, also, by going sedate like I did, I felt that would give me more in the way of confidence for my little adventure.

My first stop was downtown Philly and my favorite comic book shop for this week's newest four color offerings. After finding a parking space some thirty or so feet from the store, something absolutely remarkable occured: I hopped out of the car almost immediately after I killed the engine and put "the Club" on the wheel, casual and casual could be. No five, ten or fifteen minutes spent mustering my courage, I just got out, in my long skirt and heels and went into the store. There were some half a dozen guys in the store yakking about the terribly disappointing Punisher: War Zone and I jumped right into the chat, nobody gave me and my outfit a second glance, and I was in there for a good twenty minutes, buying comics and chatting about superhero movies.

After leaving the comic shop, my next stop was over the bridge and into South Jersey where I went to Barnes & Noble bookstore near the Moorestown Mall and spent a good half hour there, browsing the manga and magazine shelves, I even took the time to enjoy a cup of hot tea, sat at a table, legs crossed, I was just another customer. Even though I was in a long line for close to ten minutes, no one gave me so much as the time of day, never mind any wide-eyed stares or double takes or anything like that. I found that to have been a delightful experience within an experience. There I was, in a crowded bookstore, a man wearing a skirt and high heeled boots and nobody that I could see gave a damn. Needless to say, that did wonders for my confidence.

Next stop: the nearby Moorestown Mall. Again, no hesitation, I just got out of the car and went right in, head high and acting bold, like I belonged there. And I did. Oddly enough, I didn't bother with lunch as I was too keyed up from energy to eat (but I'll soon correct that oversight, I'm starved), so I strolled through the mall, making sure I was seen by everyone in a holiday crowded mall. After buying a gift from Hickory Farms for a friend, I left for Home Depot to buy a new trash can for my kitchen, once again, jumped right out, went right in, bought what I needed, paid for it and then left for Best Buy to see what new anime was in, sadly, there wasn't any to buy, but I still wandered the aisles for a solid half hour before going home after a four hour outing.

I have to say it really felt damn good to be out and about in heels and a skirt. I felt bold, confident and empowered, and it was a hell of a lot of fun too. My only complaint was that it didn't occur to me to bring my camera with me so I could have my picture taken while outside, but I'll remember that for my next trip. Oh, yeah, I forgot to bring my handbag, fortunately, the pockets of the skirt were deep enough for my wallet and keys. Again, food for thought for my next outing. And yes, there WILL be a future outing in heels and a skirt!

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I like the story line as it unfolded in the comic book shop in downtown Philly. I think the fact that you talked to people on an extensive basis there really takes your street heeling to another level. Instead of merely being a spectator to other people's activities, you became a participant as well. Congrats.

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Great Day Jeff!! You have more nerve than I do and my hat is off to you my friend. I can't believe you did even get a comment from anyone, but you do live in a semi large city and people are busier than where I live. Again my hat is off to you my friend.

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JeffB:-) Being a bit down to earth like yourself, the thought of you going out in a short skirt never entered my mind. Being that I have done that in the past, I can tell you that there sure is a lot of cold air that can blow up under a short skirt, especially if you are wearing panties and pantyhose underneath, and you were right to wear a longer one for the weather as I suspected you would do. Your outfit looks perfect on you as it would look on a female. It is a sensible look for the time of year and the weather conditions that you encountered. Cheers--- Dawn HH

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lol, I'm amazed he went out in that sweater! :w00t2: Kudos to you Jeff.

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lol, I'm amazed he went out in that sweater! :w00t2:

Kudos to you Jeff.

LMAO :lmao:;-) !!!!!!!!!!!!!

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It's called "diversion" -- wearing that sweater attracted peoples attention to it and kept them from noticing his skirt and boots.....:w00t2::lmao::lmao:

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First off...I like the sweater! I have a few similar sweaters, vintage from the 1980's that I like to call my Bill Cosby collection (for those who do not know what I am talking about, just check out Nick at Night sometime.) That's a great outing! You have wanted to do a skirt and heels for sometime and you did it with great confidence and style. I have noticed that my anxiety of getting out of the car has dissipated to practically nothing in the last few months, and the more obvious I show my heels, the less I feel it. Your conversation in the comic book store is a great example of how we are not defined by the clothes we wear as is the fact that you just went about your business for the day in the way you chose to! I am going to give every effort to getting out there in a skirt in the near future thanks to your inspiration. On a side note, I haven't been to Philly for years. The last time I was there was over 20 years ago (you know when Bill Cosby was the king of TV) and was wondering if downtown had changed much. Your reference to "the Club" makes me think that it hasn't. I have a great story about going to Temple University as part of a visiting pep band for the Atlantic 10 championships...but like I said, that's for another time...

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JeffB ... Great outing as usual. I liked your outfit, including the sweater. I too am a fan of comic books. I collected the old DC Comics back in the 60's, but gave them away to our neighbor's son who was mentaly challenged. I don't feel bad about that because he really loved to read them. I do still have a collection of old Marvel Comics from the 60' and 70's locked away in storage. You have once again inspired me to go to the comic book stores in town in high heels and see what I can find and any reactions I might get. Thank you again for sharing your adventures with us and Please, please, please keep them coming!!!!

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Thanks for the comments, everybody! I appreciate them! The experience of wearing a long skirt, feeling the denim swish about my legs as I walked, combined with the clicking of my heels was absolutely heavenly to me, and I loved it in ways I can't possibly describe. Makes me wish I had done this a long time ago!

kneehighs: My goal for my outings is to blend in with my surroundings, well, as best I could in a skirt and heels, and no one in the shop said a thing or looked at me oddly, mainly because I'm regular customer and visit there once or twice a month, so I'm fairly well known, and, as a whole, comic book fanboys like myself are a friendly lot which helped considerably! :w00t2:

secondtake20: I guess that living in a big city with it's "seen it all" mentality made what i did yesterday all the easier to have done. I think that being out and about at this time of year made things a breeze because the throngs of people out and about are more concerned with holiday shopping to pay much if any attention to a guy in a skirt.

Dawn HH: I'll let you in on a secret. If the temperature had been say, ten degrees warmer yesterday, I would have worn a shorter skirt!

Tech & Bubba136: Hey! Don't go dissing my sweater! It's been one of my faves for years! :lmao:

HappyFeat: Like most things I do, yesterday's outing was pure spur of the moment stuff, but I'm damn glad I went with that impulse because I had a fantastic time. Like I said, I had no idea wearing a skirt and heels was so much fun! If you ever decide to follow in my footsteps, I'm sure you enjoy yourself as well. I'm still amazed I felt less trepidation being seen in a skirt than wearing heels with pants. I can't figure that out. And you're right, the clothes we wear don't define who we really are inside, but are a part of our personality. By the by, Philly hasn't changed all that much, it's neater and cleaner, but still has it's rough spots.

roniheels: I've been a collector for a long time now, though nowhere near as rabidly as I used to be as my passions these days swing towards Japanese manga and anime. Meanwhile, I'll certainly do my best to keep the adventures coming!

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12/14/2008:

Since some of you guys dissed the sweater I wore yesterday (I swear, there's just no accounting for taste :w00t2:), I opted for a different sweater for today's skirt and heels outing:

Posted Image

Posted Image

As usual, I sported my black leather jacket over a thick black and dark green patterned sweater, a black, calf length knit skirt (with a slit in back), L'eggs black tights and the Payless "Tara" boots. Oh, yeah, since that skirt had no pockets, I brought along my handbag as you can see in the pictures. After yesterday's successful outing, I decided to push the envelope just a little further by opting for a clingy, dressier skirt, just to see what would the reactions would be, especially when paired with the handbag I carried. As for reactions: there weren't any.

I went to a strip mall in a western suburb of Philadelphia for my outing. My first stop there (after ten minutes of courage building) was a Hallmark store where I spent a good twenty minutes picking out Christmas cards for family members, then it was off to Borders right next door. After picking out a magazine devoted to the Nintendo Wii (which I'm planning to buy myself for Christmas), I got into a ten minutes conversation with an older black woman about Barack Obama, she absolutely gushed about our incoming President and we talked about the tremendous significance of Obama winning the election and how he has to hit the ground running to deal with all the problems facing the country. At no time did that lady give my outfit so much as a second glance.

After bidding her goodbye, I went to the instore cafe where I bought a tall iced tea and sat in the lounge for a solid half hour reading the magazine while sipping my tea, legs crossed like a woman, acting as casual as one could be----and no one gave me so much as the time of day, never mind any funny looks that would be associated to seeing a man wearing a skirt and high heels, a handbag in my lap to boot. That's why I've come to really enjoy going to bookstores like Borders and Barnes & Noble, where I can do whatever I want and not be bothered. I felt so at ease the whole time, I actually forgot I was wearing a skirt, that's how comfortable I was while I was in the store. I then got in line which was fairly long, bought the magazine and left for the return trip home.

After back to back outings, wearing a skirt in public became as natural to me as breathing, and that amazed me. And, yes, it's a great deal of fun too! Already I can't wait for my next outing!

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lol, ditch the sweater, any sweater and try a shirt.

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lol, ditch the sweater, any sweater and try a shirt.

Be glad to----come spring! Right now, it's cold outside! :w00t2:

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JeffB :-)

Another great outing. Congrats :w00t2:

Too bad you did not bring your camera with you in your bag.

I'm sure many of us would like to see some picture of you outside.

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JeffB:-) Boy!!! Tech sure is tough on you about your sweaters. I see nothing wrong with your outfit, but try a shirt and maybe Tech will smile on you for once. You know---some guys are quite comfortable wearing sweaters, some are not. Now---I have nothing against anyone wearing sweaters, it's just that they are too warm for me and make me sweat bullets. Maybe that is why they are called SWEAT---ers. When your hot, you are HOT!!! TEE! HEE! Cheers--- Dawn HH

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JeffB:-)

Boy!!! Tech sure is tough on you about your sweaters. I see nothing wrong with your outfit, but try a shirt and maybe Tech will smile on you for once.

You know---some guys are quite comfortable wearing sweaters, some are not. Now---I have nothing against anyone wearing sweaters, it's just that they are too warm for me and make me sweat bullets. Maybe that is why they are called SWEAT---ers. When your hot, you are HOT!!! TEE! HEE!

Cheers---

Dawn HH

Nothing against his sweaters, but a sweater really isnt "heeling" material really. Heels seem to command a certain amount of "smartness" yet while I'm sure we all have our own "favourite sweaters" (I know I do), they just dont seem to live up-to the statement that a pair of smart heels is making.

Its like, top half "couch potato, at home comfy" and bottom half "smart, out shopping, kinda casual.

When its cold, a nice shirt, with a smart cardigan can look pretty smart. (Not the wooly one your gran knitted either) lol

Jeffb, I'm not trying to knock you mate, like I said, kudos for effort, but just looks odd.

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O.K. Tech---I can see your point. BTW---I don't even own a sweater myself. Cheers--- Dawn HH

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While I tend to agree that the sweaters Jeff selects are "kinda" bland and "old fashioned," I actually believe the darker colors draw less attention and suite his complexion and build a lot better than brighter colors would -- especially in wintertime. Actually, if you just look at him from the waste up, there is nothing unusual about his appearance that would cause anyone to take a second look. From the the waste down, however, he looks comfortable dressed in the outfit he's wearing. So, even when someone bothers to take another look, and they digest the entire overview, he just appears to be a man wearing a skirt and high heel boots and so comfortable and "nonchalant" in his demeanor, that the "blend between male and female attire becomes "workable" and natural appearing. Keep on keeping on, Jeff. "U da man!"

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My, my, my! So much discussion over a mere sweater! Meanwhile, there's been very little chatter about the skirt and heels. Just what I hoped for!! Despite wearing articles of clothing and footwear seen more on females than males, I always endeavor to blend into my surroundings as best I can, hopefully to the point where no one pays any attention to my wearing a skirt and heels. All this talk over my sweater justified my successful strategy. By the by, Bubba, your dissemination of my outfit was outstanding! Thank you very much for your unintentional cooperation, everyone! Perhaps I'll invest in women's tops and sweaters to wear on my outings! Heh!

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Outstanding outing JeffB! Nothing is better than just doing your thing in a natural and relaxed way. The skirts work for you and you wear them well. Just as you posted, even here when the discussion turns to your tops, away from your bottoms, then you prove the rule that a guy in a skirt is no big deal!

Perhaps I'll invest in women's tops and sweaters to wear on my outings! Heh!

I gotta warn you that this is a slippery slope...for me it was women's jeans and pants and now I have basically two wardrobes! However many of the pants I wear on a regular non-outing basis, but removing gender form clothing can get very expensive!

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I'll invest in women's tops and sweaters to wear on my outings! Heh!

Jeff, that is plan!!

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