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The Jaunts of JeffB!


JeffB

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Over the years we may learn to feel more natural within ourselves, but it's really quite amazing to evoke that reaction in someone else. It's a well-deserved compliment Jeff.

 

Indeed it is, my friend. And when one rarely gets compliments from complete strangers, that makes the experience all the more enjoyable.

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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JeffB,

 

As usual you had a nice heeling jaunt. Great look BTW. I like to wear tights too, but usually under slacks or leggings. I haven't worn a skirt in a very long time, but I do wear leggings with a long polo shirt of fleece top. The very thin leggings are very much like tights. With that look I'm almost wearing a skirt, short one at the very least.

 

Happy Heeling,

bluejay

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Thanks for the kind words, bluejay. Tights add another layer of experimentation when it comes to fashion, deciding what they look best with, and that's all part of the fun!

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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Thanks for the kind words, bluejay. Tights add another layer of experimentation when it comes to fashion, deciding what they look best with, and that's all part of the fun!

An easier question is with what tights/leggings don't look good.   :penitent:

 

TBG

I dream of a world where chickens can cross roads without having their motives questioned.

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An easier question is with what tights/leggings don't look good.   :penitent:

 

TBG

 

Quite right, my friend! HA!  :lmao:

Jaunt #212, 3/16/2014:

With March Madness™ (the NCAA men's basketball tournament for the sports challenged) kicking off this coming Thursday, my weekends figure to be rather busy for the rest of the month, so I thought I'd get in a jaunt before spending my Saturdays and Sundays into early April chained to my couch, so I headed out in my black leather jacket over a black turtleneck, my 32 inch a-line denim skirt, black tights, the Pleaser 4 inch heeled "Vanity" knee boots and a black handbag. With temps barely into the low 40's with a good wind blowing, it was fairly chilly, but I felt nice and warm in my ensemble, having fully devoted myself to wearing skirts, I had to figure out what to wear with them in the cold of winter as well as the heat of summer, by wearing a longer skirt with tights and boots, I was properly prepared, and looking good for the environment.

 

My first stop was to a branch of my bank in the University City area as I needed to tap a cash machine for my next stop at the Post Office, hopping out, I passed a couple that paid me no mind, after getting my cash, I got back in my car and went to the Post Office as I needed to buy a couple of money orders. After feeding the meter, I headed in where there was a long line, some ten people ahead of me, but no one gave me so much as a glance as I got in line and patiently waited for my turn with a clerk. About ten minutes later, I was at the counter, bought my money orders, then walked over to a counter to fill them out, dropped them in the box and headed out. My next and final stop was to Best Buy in Springfield, walking inside, there was a fair sized crowd at just after 1 p.m., and the people inside barely noticed me, my objective there was to buy some speaker wire and a digital coaxial cable, but, since this was Best Buy, there was no going in, finding what I needed and going right back out, I spent well over half an hour in the store, and, as usual, it was enjoyable, and no one made a big deal about how I was dressed. If you're dressed nicely and appropriately, why should you be bothered, even if you're man wearing a skirt and heels.

 

While brief, it was a pretty good outing as I got to go out and about, dressed how I like, nothing more, nothing less. As for when my next outing will be? Well, that's anybody's guess. Heh!

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I don't want to LOOK like a woman, I just want to DRESS like a woman!

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WOW! I just noticed that I repeated an entire out that I had worn, being the black leather jacket/A-line denim skirt/Pleaser knee boots on 3/1 and 3/16! Same necklace too! Horrors! That's what I get for not paying attention enough to past jaunts!  :lmao:

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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WOW! I just noticed that I repeated an entire out that I had worn, being the black leather jacket/A-line denim skirt/Pleaser knee boots on 3/1 and 3/16! Same necklace too! Horrors! That's what I get for not paying attention enough to past jaunts! :lmao:

Obviously, it was a good outfit. Just don't let it happen again. ;))
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Obviously, it was a good outfit. Just don't let it happen again. ;))

 

Aye, aye, captain!

 

No problem with that, JeffB. I wore the same ensemble tonight that I wore on Sunday afternoon.

 

Happy Heeling,

bluejay

 

Ahhh! But did you do that on purpose, or by accident like I did?

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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In looking back through some of the posts , I think the outfit with the white belt,purse and Molly wedges is still one of the best looks for you. Then again I am also partial to the picture with the Black Molly and jeans. Anyway keep up the "Jaunts" , I have gotten some good ideas from seeing the pictures. Thanks !!!

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No matter, Jeff. If it worked well for you once, it's logical that it will work well again. Nothing wrong with wearing the same outfit twice, whether by accident or intentionally. Steve

  Well, if that's the case, perhaps I might do that again sometime in the future. Heh!  

In looking back through some of the posts , I think the outfit with the white belt,purse and Molly wedges is still one of the best looks for you. Then again I am also partial to the picture with the Black Molly and jeans. Anyway keep up the "Jaunts" , I have gotten some good ideas from seeing the pictures. Thanks !!!

You forgot about the white skort I wore with the matching belt, purse and shoes. I remember that was a fun outfit which I had worn to a local slots parlor. That reminds me to look for a white denim miniskirt to wear this coming summer.

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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11/02/2008

Because Thighbootguy clamored for them:

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That's right, friends, I finally broke out my thigh high boots (Pleaser Legend 8868 in black) and wore them on an outing today which I paired with my black leather jacket, a black turtleneck and gray, skin tight, men's lowrise jeans. After an unseasonably warm Saturday that saw a high of around 70, it was a good deal cooler today, perfect for wearing the boots. My travel plan was to the western suburbs and my first stop was at a Borders bookstore for some shopping and a hot cup of tea. After arriving at the store, it took a good ten minutes to get up the courage to leave the car as this was the first time I've worn thigh boots in three years, I was more than a little nervous and had to acclimate myself to wearing them again.

You see, it's one thing to discreetly wear heels under long pants or jeans, but with thigh boots, there's nowhere to hide, you're exposed for the entire world to see, that's what I had to get used to again, especially since this would only be the second time in my life I've ever been out in thigh boots. Finally I left the car and headed towards the store, the boots fit snugly and the 4 1/2 spike heels pleasantly sharp and loud on the gorund, silly as this seems, the clicking of the heels actually calmed me down and helped to build up my courage for this little adventure. Once inside the store where pretty much no one paid me any attention, I wandered the magazine aisles, picked up a few sport mags, then went to the store's coffee shop for that mug of tea to warm me up from being outside.

I sat with my tea and magazines in the lounge area, surrounded by several people, including a guy and girl in the early twenties, again, there was no hiding the boots, but I was now okay with that, I didn't mind being in that all too obvious fishbowl as I read and sipped my tea. Fifteen minutes in, the couple got up to leave, as they passed me by, the boy said to me, "Cool boots, dude!" I grinned and told him thanks. Didn't expect that, a compliment from a male on my wearing women's shoes, definitely a first for me, and I enjoyed that. After I finished my tea, I got in line to pay for my magazines, the cashier glanced down at the boots and grinned before ringing up my purchase. Having not just one person, but two acknowledge the boots was rather exhilarating to say the least. I got a kick out of that.

On the road again, emboldened from being in the bookstore, I drove to Best Buy for another James Bond Blu-Ray disc. For anyone who's ever shopped in Best Buy, the place can be packed on a Sunday, and that was the case here, but I just strolled in the store like any other customer, wandered around the aisles so I could be seen (but not acknowledgment of the boots) before making my purchase and heading out after a good twenty minutes in the store. My final stop was at Home Depot for fresh batteries to put in my smoke detectors, I thought I heard someone mutter, "Damn! I thought Halloween was over!" but I paid that no mind, after all these years, I've gotten used to odd comments on my footwear. After buying my batteries, it was back to the barn in time to gorge on the day's NFL action.

All in all, another good outing, but wearing my thigh boots made it just a little more special to me. It was a lot of fun to wear the boots and, at times, it was all I could do not to stare at my reflection as I looked damn good in them. Already, I can't wait for another opportunity to wear the boots!

Great job buddy!  I'm glad the guy had the balls to admit that he liked the boots on you...Most guys only "dream" of wearing such powerful sexy boots...Give yourself plenty of credit for having the balls to do it!  Wish I could go on a booted outing with you sometime..

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Great job buddy!  I'm glad the guy had the balls to admit that he liked the boots on you...Most guys only "dream" of wearing such powerful sexy boots...Give yourself plenty of credit for having the balls to do it!  Wish I could go on a booted outing with you sometime..

 

Wow! Over five years ago! How time flies when you're having fun! Thanks for the compliments! It does take a certain amount of nerve to wear what I do, but once you've got it all together, it's pretty easy, and fun!

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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looking real good there jeff-now a-days I only wear my avatar boots around the house, I cant really do much street walking in them anymore (never really could to tell the truth) but when I do wear them in the house I enjoy them all the same.

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  • 2 weeks later...

Jaunt #213, 4/5/2014:

Saturday was nice and sunny, though brisk, thanks to a stiff breeze, but it was nice enough for a new jaunt as I hit the road in my dark brown pleather jacket (which I hadn't worn in awhile) over a brown mockneck, my 21 inch light denim pencil skirt, black tights, the Blondo 2 inch heeled loafers and a black handbag. I found it to have been a casual, yet moderately dressy outfit for a Saturday outing, the skirt I wore is fun for me thanks to the walking vent in back which, in my mind, lends an air of daring, and I felt totally comfortable in it, and while my legs look good bare, adding hosiery really makes them pop, lastly, the modest heels of the loafers sound nicely loud and sharp on the pavement, making the shoes a treat to wear. All in all, a good outfit to spend a day in.

 

My first stop of the day was downtown to visit my favorite comic book shop. Having parked nearly two blocks away, I got to enjoy a nice little walk to the place, and no one gave me the time of day, no stares, odd looks or giggles, after a good twenty minutes in the shop, I returned to my car, eliciting no excitement, swung by a convienience store for a newspaper, then hopped back in the car and drove over the bridge into South Jersey. I headed to Chick-Fil-A near Moorestown Mall, hopped right out and went inside, there was a fair crowd in the store at just after high noon, again, no one gawked or stared as I bought my lunch, sat down and ate while pouring over the sports section. After eating, I got back in my car and went to the Mall and it's recently rebuilt multiplex to see Captain America: The Winter Soldier, I did get a couple of stares from people in passing, but nothing more than that, but a twentysomething girl taking tickets smiled and complimented me on my pendant, I smiled back and thanked her. Feeling nature call, I went into the men's room to take care of business, passing two guys who ignored my appearance before taking in the movie which was great.

 

After the film, I left the mall and drove to the nearby Barnes & Noble where I spent a solid half hour amidst a pretty good crowd for a Saturday afternoon, but again, no one made anything of my appearance the whole time I was there, my final stop was at Best Buy which also had a good crowd, yet again, I garned no undue attention, save of course for salespeople who asked me for help, I marveled at Samsung's brand new curved 4K HDTV which had an incredible picture, and, at $4,999, it OUGHT to be incredible! Leaving the store with a new Blu-Ray purchase, I headed home to catch more of the NCAA men's Final Four. It was a good outing and I enjoyed every minute. No one made a big deal, or a small deal of how I was dressed, by acting perfectly at ease, I gave no one a reason to take undue notice of me. And yeah, it was great fun! More fun to come.

Jaunt #214, 4/6/2014:

Nothing like jaunts on back to back days to make a freestyler feel real good. Way back in the day in this thread, I used to devote Sundays to getting dressed up for outings, so I thought I'd return to that particular theme with today's outfit which represented a wee bit of experimentation, thanks to something new I wore: a plaid skirt. Some four or five years ago, I bought a 35 inch blue and black plaid skirt from Sears, mainly because it appealed to me, however, I never got around to wearing it because I wasn't sure of what to pair with it, at least not until today as conditions were just right, even though the sun was out, temps were only in the low 50's and it felt a good five degrees cooler, so I wore the skirt with a black mockneck, the Pleaser "Vanity" 4 inch heeled knee boots along with my Gloria Vanderbilt denim jacket and my faux black croc handbag which I hadn't used in awhile. Now, I never so much as leave my bedroom, never mind leave the house unless I'm 100 percent confident that I looked my very best, and I thought I did here.

 

My first stop of the day was to the west and Best Buy in Springfield as I was in the mood to buy something, and it's hard NOT to do that when in there. I spent close to thirty minutes in there, and no one gave me the time of day in my outfit, I was just another shopper, and that was fine with me, after leaving the store with the Blu-Ray version of Kill Bill (part one and two), I headed downtown to for another experiment: to be seen. It took a wee bit of time to find a parking spot near Rittenhouse Square, perhaps THE busiest spot in downtown Philly, what with the park that attracts scores of people, especially on a sunny and relatively mild early Sunday afternoon. Feeding the meter, I strolled down the street to a nearby Barnes & Noble, ignored by other pedestrians and went in, the store was plenty packed, but no one bothered to notice me as I strolled through the store, after buying the latest Sports Illustrated, I left the store and slowly strolled through the park, packed to the gills with people, finding an unoccupied bench, I sat down, crossed my legs and read my magazine, staying in one place for well over thirty minutes, dozens of people, young and old, male and female passed me by and no one, and I mean NO ONE noticed me at all. I found that mildly surprising, yet wholly satisfying as well because I was given my space like every other person, despite how I was dressed.

 

While I was very pleased with how well things went, I'm smart enough not to let that success go to my head because I know there's plenty of places in this city where the end result would have been anything from disastrous to horrific, there are places I don't dare go in freestyling mode, so I stick to venues where I feel comfortable and safe. And that's what makes what I do all the more enjoyable.

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I don't want to LOOK like a woman, I just want to DRESS like a woman!

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JeffB,

 

Those were two great looking ensembles, you wore on Saturday and Sunday. Sounds like you had a great time out and about in your skirts and heels.

 

I enjoyed reading about your jaunts, as I always do. Keep them coming.

 

Happy Heeling,

bluejay

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Thanks for the kind words, bluejay! Yes, I'm certainly having fun, in fact, I'd even go so far as to say I'm having MORE fun since I've gone all skirts on my outings. Can't get enough of them! And I'll keep the jaunts coming.

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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Looking great as usual, JeffB.  Thanks for sharing your jaunts with us, truly an inspiration.  

 

While I was very pleased with how well things went, I'm smart enough not to let that success go to my head because I know there's plenty of places in this city where the end result would have been anything from disastrous to horrific, there are places I don't dare go in freestyling mode, so I stick to venues where I feel comfortable and safe. And that's what makes what I do all the more enjoyable.

This is excellent advice as well.

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Jaunt #215, 4/10/2014:

I'm home today because I have to do prep work starting this afternoon for a colonoscopy tomorrow, but, with the weather sunny and mild though breezy, I decided to head out for a brief outing, wearing my Gloria Vanderbilt denim jacket over a red t-shirt, my 21 inch black denim pencil skirt, the Payless "Karmen" pumps in black patent and my favorite black handbag. I saw this as a casual but dressy outfit for my little venture, and when I wear a skirt and heels, I want to look my best. As for the Karmen pumps, like the other two pairs I had worn, they were very comfy and easy to wear with their three inch heels that made the sort of loud, sharp clicking sound on the pavement that I love.

 

My first stop was to a branch of my bank in University City to tap the ATM, after I parked, I hopped right out, fed the meter and walked some fifty or so feet to the bank to use the machine, passing several people who paid me no mind, though I did get a turned head from a motorist. After leaving the bank, I headed to the main branch of the Post Office little over a mile away to take care of business, after I parked, I jumped right out, fed that meter and strolled right in, my wait wasn't all that long, just under ten minutes before I was waited on to buy a money order to renew my newspaper subscription, there were three people behind me, but no one looked at me the whole time I was there, and I acted just like everyone else, and I was grateful for that, to be treated no differently from everyone else in the place. After leaving the Post Office, I drove into Center City and to Rittenhouse Square where I spent some quality time this past Sunday. It took some fifteen minutes to find a parking spot which was a block away from the Barnes & Noble, once I did, I got out, fed the meter and strolled to the store where I spent some fifteen minutes before buying another sports magazine and I retreated to the park to read.

 

For nearly half an hour I sat on a bench in the park reading, legs crossed, acting casually while I read, and, just like on Sunday, no one gave me the time of day be people who passed me by, even though I wore a shorter skirt than on the previous outing that rode up on me while I sat. And yet, nothing, no notice whatsoever, that made me feel positively delightful, it was sunny, the weather mind and I was sitting in a park wearing a skirt and heels, going ignored by passerby. That was so cool. I could've stayed there for much longer, but I had to head back home to start the prep work for tomorrow's procedure. While the outing was brief, it was enjoyable, I'll definitely have to return to the park on future outings because it's a great place to spend quality time. And with the weather warming up, it'll be time to break out my miniskirts for the season to come!

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I don't want to LOOK like a woman, I just want to DRESS like a woman!

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I am a fan of shorter skirts as apposed to long ones.  So your new outfit totally work for me!  Well done!

 

Thanks for the kind words. I'll certainly be wearing shorter skirts now that spring is here and summer is not far behind. I can't wait!

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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Jaunt #216, 4/12/2014:

Yes, spring has truly sprung in these parts, and with a forecast filled with sunshine and warm temperatures, I went on my first jacket-less outing of 2014, wearing a black polo shirt, my 21 denim pencil skirt, the new Payless "Margaret" espadrille wedges which I just got the other day and my trusty black handbag. I'm sure others will agree that there's nothing more fun than breaking in a new pair of shoes, and I was eager to take these beauties out for a spin as they look very sharp and stylish and were easy to walk in, thanks to the three plus inch woven wedge heels, oh, yeah, the criss-cross black patent peep-toe upper was also appealing to me and made these shoes such fun to wear as they went well with my skirt, making for a nicely casual Saturday outfit.

 

After driving into town and parking half a block away from my favorite comic shop, I hopped out, fed the meter and went to the store, attracting no attention, following some twenty minutes in the store, I left, and as I crossed the street, I was stopped by a smiling twentysomething young woman who said said my shoes were pretty, then added that she was jealous of how I could walk in them, saying she'd fall flat on her face if she wore them. I smiled back and thanked her for the compliment. It had been quite some time since someone complimented me on my shoes, and I thought that little interaction was cool. Encountering someone openminded enough to say something nice about my wearing women's shoes made me feel quite good. Returning to my car, I motored over the bridge and into South Jersey where I had lunch at Boston Market near the Moorestown Mall, it was a quarter past twelve, so there was a decent crowd in the store, but no one said a thing while I dined. Then, I headed to Barnes & Noble where I did get a long look from an older couple leaving the store as I entered, otherwise, nothing newsworthy during the thirty or so minutes I was there.

 

Leaving the store with a couple of sports magazines, my final stop of the day was to Best Buy which I just can't stay away from, no matter how hard I try, strolling in, I saw there was a good crowd for a Saturday afternoon, but I was given my space by all the shoppers for the thirty minutes I spent there before going to the register with a Doctor Who DVD. Upon leaving the store, I made a beeline back home to watch the Flyers play Pittsburgh, and the orange and black won over the Penguins in overtime. WHOO!! Another great day wearing a skirt and breaking in a new pair of heels, what more can a freestyler ask for?

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I don't want to LOOK like a woman, I just want to DRESS like a woman!

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JeffB,

 

Nice look today. I'm glad you enjoyed yourself out and about today. Looks like spring if finally here.

 

Last night, while attending a dinner in the NYC area, I saw  at least three ladies, already wearing white pumps and white sandals. Heaven forbid, it's not even May yet and certainly not even close to Memorial Day, for the traditional wearing of white shoes. I can't wait to wear my white heels, but will wait till at least mid-May to do so!

 

Happy Heeling,

bluejay

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Last night, while attending a dinner in the NYC area, I saw  at least three ladies, already wearing white pumps and white sandals. Heaven forbid, it's not even May yet and certainly not even close to Memorial Day, for the traditional wearing of white shoes. I can't wait to wear my white heels, but will wait till at least mid-May to do so!

 

Perhaps those ladies were mavericks who thumb their noses at conventional fashion mores and march to the beat of their own drummers instead of blinding following the calendar. Hey, more power to them.

4/13/2014

With the weather nice today, I decided to go on a SUNDAY DOUBLEHEADER!

 

#217, Morning:

At around seven a.m., I headed out to the supermarket, whether I go jaunting or not, I always go shopping early on Sunday before the store gets crowded. For this outing, I wore my Gloria Vanderbilt denim jacket over a brown t-shirt, the Old Navy 20 inch khaki skirt, the Payless "Jefferson" wedge pumps in brown and my chocolate brown handbag. Just a casual sort of outfit for an early morning expedition. After arriving at the supermarket, I hopped out, grabbed a cart and strolled on in, not much of a crowd, just a few people at this hour, so I went about my business of grocery shopping, taking my time as I was in no hurry at all as I strolled the aisles. As is often the case, going down the frozen food aisle was a chilly proposition with all that frigid air on my bare legs, but I found it rather invigorating. By around quarter to eight, I was done, paid for my purchases and left, no big deal at all.

 

#218, Afternoon:

The afternoon jaunt served one purpose, to break in another new pair of shoes from Payless, they being the "Nicole" platform wedge sandals which I paired with a blue polo shirt, my 21 inch black denim pencil skirt (I've arrived at the conclusion that I look great in pencil skirts and will wear them more often) and my black faux croc handbag. My first stop was to my home away from home, yes, Best Buy (Springfield), after parking, I hopped right out and headed in, the sandals were an absolute dream, ridiculously easy to stand and walk in and very comfortable to boot, oh, yeah, they looked great on my feet as well, and that's got me to seriously considering a pedicure as I can see myself wearing the Nicoles and the other sandals in my collection throughout the spring and summer. Walking into the store, there was a fairly good crowd for just after twelve noon, and even though the heels were only four inches, it still felt like I was standing head and shoulders over everyone in the store, I did get a few stares here and there, but no one made a scene.

 

After checking out with the Blu-Ray version of Star Trek Into Darkness, I left for lunch. I drove down the road to Subway where I enjoyed a six inch meatball sammich in almost an empty store, then drove to Bed, Bath & Beyond to stock up on bath towels before heading home, the whole time, I was amazed at how easy, and how much fun it was to wear those kicky shoes, kinda makes me wish I had started wearing platform sandals long ago. Well, that's it for now, I'm sure this won't be my only Sunday Doubleheader now that spring is here.

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I don't want to LOOK like a woman, I just want to DRESS like a woman!

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JeffB,

 

You had a great outing today. The pencil skirt worked well with your ensemble, this morning. Great choice of colors.

 

Your afternoon ensemble was equally well put together. I like the wedge heel sandals. And yes it's time for you to get a pedi, to really highlight your feet in your sandals. Take it from Steve and myself, a pedi and polished toes adds a lot to wearing sandals. I gets lots of compliments from the ladies with polished toes. My favorite colors are red and hot pink. Hopefully on Tuesday, I will be getting my first pedi of the spring. I'm looking forward to it!

 

Happy Heeling,

bluejay

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Thanks for the kind words, bluejay! I work hard to put together outfits that help me look my best when out in public. As for that pedicure, I'll definitely see about that. Heh!

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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I'll reinforce what Bluejay said. I was never a fan of pedicures - until I had one! Then I was amazed! The process was wonderful, with a very enjoyable and relaxing foot massage. The finished product - the artistically done toenails - was so much better looking than what I had before. I even get my fingernails colored now! I don't go for the bright reds and pinks like Bluejay does. I stick with more muted colors like metallic copper and satin dusky rose. My friends think I'm weird, but they thought that before anyway, and they're still my friends - I haven't lost any because of my choice to color my nails. The main thing is that my wife likes the way I take care of my nails! Grooming is important to her, and colored nails show the world you care about the details. So go for it, Jeff. Ask the women in your office where they get their nails done and to recommend a good salon. Go there, walk in like you're a customer (!) and enjoy the experience. Tip well if they do a good job and you'll be welcome to come back again and again. The gals at the local salon love me! Maybe it's the chocolate candy I bring that has something to do with it!

 

Steve

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