The Jaunts of JeffB!

[Pumps]

TBG: Cool looking pic there, got a chuckle out of it, even though I don't wear heels around the house! Heh!

 

WarrenB: Thanks for the kind words. Much appreciated.

 

bluejay: Crazy weather, hasn't it? Glad you did get to go out.

 

Kilty: Nope, no burka! Sorry to have disappointed you!

 

Jaunt #256, 3/29/2015:

As promised, I didn't wait 84 days before my next outing, rather just twenty hours, braving sunny though chilly temps that barely reached 40 for a brief jaunt (more March Madness games were on tap starting at 2 p.m.) in my black leather jacket over a red turtleneck, a 15 inch denim skirt, black tights, the Pleaser four inch heeled thigh boots and my favorite black handbag. While it was considerably less than springlike, I was still fairly warm and protected from the elements as I headed westward into Springfield and Bed Bath & Beyond to stock up on washcloths and bath towels, it was shortly after eleven a.m. and there was a decent crowd in the store, no one paid me much in the way of attention as I entered the store and cruised the aisles until I found what I needed, then waited in line a good few minutes while other shoppers got a good look at me, as usual, adults never gave me so much as a second look while young kids gazed in curiosity and puzzlement, par for the course after all these years, so I was used to those reactions.

 

From there, I headed back into the city and to the main branch of the Post Office which was open on Sunday to buy a money order to send off to the state capital to renew my license tags. That proved to take a tad longer than I thought it would as a whole lot of people were there to take care of business, and, as a result, I wound up waiting in line for nearly twenty minutes before I was finally waited on, so I got to be on display for all to see. To be honest, I thought more about how I had to wait so long for service rather than the fact I was in the fishbowl, a lesson of sorts about avoiding the Post Office on Sundays unless I absolutely had to go there. Well, after I bought my money order, filled it out and dropped it off, I got back in the car and returned home for lunch prior to chilling out and watching all that good hoops action. Even though it was a short outing, it was still a good one, and even though it felt more like January than late March, there was no reason NOT to wear a miniskirt, mainly because I wanted to, and I look damn good in it. Just part of the joy of freestyling. More to come....

 

I really like this and the previous looks. I know for myself I prefer boots if I wear a skirt outside.

[JeffB]

Jaunt #257, 4/4/2015:

A combination of blustery weather and a picture by redandwhite in the Gallery section gave me the inspiration for the outfit I wore on my latest outing, that being my denim jacket over a black mockneck, a 21 inch stretchy denim pencil skirt from Old Navy, black tights, the Payless "Tara" boots and a black handbag. Even though spring has arrived, it was cool and gusty, so the outfit I put together made for a good choice, especially after how I liked redandwhite's combination of a gray skirt, black tights and matching boots. Regarding the skirt which I bought well over a year ago, it was comfortable and stylish with a rear slit (or, as they call it in the industry, a walking vent) and matched well with my tights and boots. The only thing more important to me than feeling good when I wear women's clothes is looking good and being appropriately fashionable.

 

My first stop of the day was to a branch of my bank to hit the ATM, parked half a block away and drew the curious stare of a homeless man sitting on a bench as I passed, after getting some cash, he stared again at me as I returned to my car. from there, it was off to my local comic shop, managed to find a spot less than half a block away from the store, I did get a couple of stares here and there, but that's okay, you have to get used to stares when out in public or you can't make freestyling work. After nearly half an hour in the store, including some chatter about the local pro sports teams, I indulged in a two block stroll through always busy and crowded Rittenhouse Square where I drew little attention, and that was cool with me too, being able to go about my business like everyone else. I swung by Barnes & Noble, spending close to half an hour there and leaving with a couple of sports magazines, returning to my car, it was over the bridge and into South Jersey, going to Wendy's in the Moorestown Mall area where I enjoyed a Baconator. Yum!

 

My last stop was to Sears for more shopping as I bought a nice blue twill skirt that came with a slim tan belt, I can see myself pairing that with a beige or tan top and those tan Payless loafers I bought a few weeks ago. Just like with most women, a man can never have enough skirts, and, as I probably mentioned previously, with winter looking to finally be gone, I'm eager to break out my spring and summer skirts for the season that's developing. More to come....

[Thighbootguy]

JeffB - Looks great.  The first adjective that struck me as very handsome, but I struggled with applying that description to a gal... but then I'm not... hence my quandary.

 

I think the element that really made the outfit redandwhite posted was the black suede boots with the dark black hose/tights  The silver zipper gave a nice contrasting accent but the key was the matt finish of the boots not contrasting with the hose.  They have a nice heel too.  It was almost like the boots didn't stop.  Someday I'll find a pair of suede thigh boots.

 

I didn't expect to see you posting for yesterday with all the Final Four Madness on TV.  I don't normally watch basketball but I took your enthusiasm to heart and watched both games.   I figure if you're going to watch any sport, wait until the end of the season when the best teams are left playing each other.  I made some popcorn and opened a beer and actually enjoyed both games.    Like I said I don't watch much basketball and I did catch myself looking for the two minute warning. 

 

It did occur to me as I was watching, I'll bet JeffB is doing the same thing. 

[Puffer]

TBG:   These boots look like your style, although they seem to be stretchy matt fabric material rather than (faux) suede.   Perhaps you prefer something less clingy?   Nice though!

 

JeffB:   You might like them too.   I'm sure they are available in the US

 

http://www.ebay.co.uk/itm/Ladys-Boots-High-Heel-Thigh-High-Zip-Stiletto-Lycra-Pointy-Black-UK4-37-UK12-45-/161066958743?pt=LH_DefaultDomain_3&var=&hash=item258056bf97

 

 

[SkirtDude]

Fantastic outfit again Jeff! Love the stretchy skirt! I bought a blue chino one that was a 23 inch stretchy number. Looking forward to your next jaunt

[pebblesf]

Jaunt #257, 4/4/2015:

A combination of blustery weather and a picture by redandwhite in the Gallery section gave me the inspiration for the outfit I wore on my latest outing, that being my denim jacket over a black mockneck, a 21 inch stretchy denim pencil skirt from Old Navy, black tights, the Payless "Tara" boots and a black handbag. Even though spring has arrived, it was cool and gusty, so the outfit I put together made for a good choice, especially after how I liked redandwhite's combination of a gray skirt, black tights and matching boots. Regarding the skirt which I bought well over a year ago, it was comfortable and stylish with a rear slit (or, as they call it in the industry, a walking vent) and matched well with my tights and boots. The only thing more important to me than feeling good when I wear women's clothes is looking good and being appropriately fashionable.

 

My first stop of the day was to a branch of my bank to hit the ATM, parked half a block away and drew the curious stare of a homeless man sitting on a bench as I passed, after getting some cash, he stared again at me as I returned to my car. from there, it was off to my local comic shop, managed to find a spot less than half a block away from the store, I did get a couple of stares here and there, but that's okay, you have to get used to stares when out in public or you can't make freestyling work. After nearly half an hour in the store, including some chatter about the local pro sports teams, I indulged in a two block stroll through always busy and crowded Rittenhouse Square where I drew little attention, and that was cool with me too, being able to go about my business like everyone else. I swung by Barnes & Noble, spending close to half an hour there and leaving with a couple of sports magazines, returning to my car, it was over the bridge and into South Jersey, going to Wendy's in the Moorestown Mall area where I enjoyed a Baconator. Yum!

 

My last stop was to Sears for more shopping as I bought a nice blue twill skirt that came with a slim tan belt, I can see myself pairing that with a beige or tan top and those tan Payless loafers I bought a few weeks ago. Just like with most women, a man can never have enough skirts, and, as I probably mentioned previously, with winter looking to finally be gone, I'm eager to break out my spring and summer skirts for the season that's developing. More to come....

Those boots look fantastic on you buddy!

[Mr. X]

Good to see you out again doing your thing Jeff

[JeffB]

JeffB - Looks great.  The first adjective that struck me as very handsome, but I struggled with applying that description to a gal... but then I'm not... hence my quandary.

 

I think the element that really made the outfit redandwhite posted was the black suede boots with the dark black hose/tights  The silver zipper gave a nice contrasting accent but the key was the matt finish of the boots not contrasting with the hose.  They have a nice heel too.  It was almost like the boots didn't stop.  Someday I'll find a pair of suede thigh boots.

 

I didn't expect to see you posting for yesterday with all the Final Four Madness on TV.  I don't normally watch basketball but I took your enthusiasm to heart and watched both games.   I figure if you're going to watch any sport, wait until the end of the season when the best teams are left playing each other.  I made some popcorn and opened a beer and actually enjoyed both games.    Like I said I don't watch much basketball and I did catch myself looking for the two minute warning. 

 

It did occur to me as I was watching, I'll bet JeffB is doing the same thing. 

 

Nothing wrong with being called handsome, heck, that's what I was, a handsome guy in a skirt and heels, nothing more, nothing less. As for Saturday's games, they didn't stat until six p.m., so I wa back in plenty of time for a nap prior to the opening tipoff.

 

TBG:   These boots look like your style, although they seem to be stretchy matt fabric material rather than (faux) suede.   Perhaps you prefer something less clingy?   Nice though!

 

JeffB:   You might like them too.   I'm sure they are available in the US

 

http://www.ebay.co.uk/itm/Ladys-Boots-High-Heel-Thigh-High-Zip-Stiletto-Lycra-Pointy-Black-UK4-37-UK12-45-/161066958743?pt=LH_DefaultDomain_3&var=&hash=item258056bf97

 

Hmm! Nice boots there I must say!

 

Fantastic outfit again Jeff! Love the stretchy skirt! I bought a blue chino one that was a 23 inch stretchy number. Looking forward to your next jaunt

  

I've had that skirt from Old Navy for well over a year and was looking for just the right time to show it off. Glad you liked it!

Those boots look fantastic on you buddy!

  

Good to see you out again doing your thing Jeff

Thanks for the kind words!

[SkirtDude]

Jeff, you inspired me to get a more stretchy type of pencil skirt, I bought some cute brown flats and asked my friend to take a picture of them with my new skirt. I think the watch is a bit bling bling but I was feeling daring

Looking forward to your next jaunt

[bluejay]

Looks nice. Kilty.

 

Hapoy Heeling,

bluejay

[JeffB]

Jeff, you inspired me to get a more stretchy type of pencil skirt, I bought some cute brown flats and asked my friend to take a picture of them with my new skirt. I think the watch is a bit bling bling but I was feeling daring

Looking forward to your next jaunt

 

The skirt looks nice, Kilty. Well done! As for the watch, you could try a slim women's style like what I wear on my outings.

[SkirtDude]

Thanks guys! I wanted to find a skirt that was a regular colour and hugged my figure, but felt the watch was a little bit out of place. Problem is with women's watches is they can be so tiny and hard to read. I know it's just a fashion accessory and I could take my iPhone out of my handbag and get the time, but a watch might as well be useful Still, fashion freedom is a learning curve

[LuvyourShoes]

Jeff, love it, as usual!

Kilty, I really like the outfit and flats!

[JeffB]

Kilty: Yes, fashion is indeed quite a complicated business, but fun to figure out.

 

LuvyourShoes: Thanks for the kind words. Much appreciated.

 

Jaunt #258, 4/11/2015:

Every time I willingly venture out into the public fishbowl wearing women's clothes and shoes, I never know what to expect, to some, that might be seen as a nervous, perhaps scary experience. Ninety-nine percent of the time, the public at large doesn't pay me so much as a moment's attention, despite how I'm dressed, and that's more than good enough for me because I don't actively seek attention, I just want to go about my business and be respected as simply another human being, nothing more, nothing less, but today, I had a most unique and memorable encounter that I'll explain a little later. As for my outfit, even though it was a bright and sunny Saturday, it was also very gusty with a bit of a nip in the air, so I dressed appropriately in my blue denim jacket over a magenta mockneck, my 21 inch black denim skirt, black tights, the Payless "Karmen" pumps in black patent and a black handbag.

 

My first stop of the day was downtown and my friendly neighborhood comic book shop, putting five bucks in the meter for nearly two hours worth of time, I hopped out and walked to the shop where I spent nearly half an hours and talked local sports with the staff, always an enjoyable thing, as I've said before, the staff of the shop are long used to the eclectic clothing I wear, so it's no big deal to them, I'm just a loyal customer, and that's good enough for me. Leaving the shop, I headed two blocks down into the Rittenhouse Square area and the Barnes & Noble where I spent almost another half hour perusing the magazine aisles and manga section before leaving with the latest Sports Illustrated, after I left, I crossed the street and entered Rittenhouse Square Park, crowded to the gills with people enjoying the nice weather, but I went ignored as I wandered about so I could be seen before sitting down on a bench to read my magazine, and be seen in a stationary location, no gawking, no double takes, no long glances, no pointed fingers, no giggles or chuckles, none of that stuff, just some pleasurable time spent with the public, and it was most enjoyable, just being able to be seen as just another person taking in the great weather.

 

With fifteen minutes left on my meter, I left the park and returned to my car, whether or not anyone took pictures or video of me, I have no idea, don't care either. Back in the car, I drove over the Ben Franklin Bridge and into South Jersey, namely the Chick-Fil-A near the Moorestown Mall, and it was there that I had that unique encounter I spoke of earlier. The store was fairly crowded as it was just past 12:30 p.m., following a brief wait, I placed my order, got my meal and sat down at a table to eat. While I was enjoying a chicken salad sandwich and reading about Friday night's Phillies win over the Washington Nationals, someone lightly tapped me on my left shoulder, I turned to look and found myself facing a New Jersey State Trooper, a Latina in her late twenties, she had a sort of, well, melancholy look on her face and a small, brief smile, in a choked voice, she said that she admired me for being who I was, something her younger brother lost his life for being. At a loss for words, all I could do was thank her for what she said, with tears in her eyes, she pressed a Chick-Fil-A gift card in my hand, thanked me again and left the store. On the back of the receipt, she wrote the following: "Hi, thanks for being who you are. Lunch is on me next time. Have a blessed day."

 

I was quite stunned, not knowing how to take it all in. Did she think I was gay? A transgender? I had no earthly idea. Look, I don't pretend to be anything more than just a middle aged male who wears women's clothing, nothing more, nothing less, but that encounter with the trooper left an indelible impression on my mind, hell, I've been thinking about it ever since. I guess I can occasionally promote strong emotions in people, simply by how I was dressed, something I never knew I had the power to do. Heady stuff indeed. From there, I drove to the nearby Best Buy, my last stop of the day to wander the aisles of electrical and electronic goodies for well over half an hour, always great fun before going to the register with a new keyboard for my computer. Another enjoyable outing, one made truly memorable after my encounter with that trooper. More to come....

[Thighbootguy]

JeffB - The outfit looks great.  It's a fine combination.  I'd suggest a shorter denim jacket that falls about at the waist like of the skirt.

 

As for your encounter with State trooper... That had to me a moving experience.  I understand your being at a loss for words.  It is hard for most people to wrap their head around a guy wearing women's clothing in public without trying to assign some justification like being gay or transgender.  I don't think too many boys are killed just for being a "free spirit" without having expressed their freedom in some manner of which the community dose not approve.

 

Jaunt #258, 4/11/2015:

Every time I willingly venture out into the public fishbowl wearing women's clothes and shoes, ,... I don't actively seek attention,

 

I disagree with your analysis.  I think the word "actively" is the key.  When you go out you do seek attention, but "passively" may be a more accurate description.  If you weren't seeking attention you wouldn't care what you wore, and we know the effort you make to look good.  Wearing good looking clothes is an attention getting device.  Also, if your goal was just to wear women's clothes and shoes, you would wear them around the house and while watching TV.

 

Looks like there is hardly room for the new keyboard on your desk.

 

 

Lastly, at $2.50/hour for parking, leaving 15 minutes on the meter seems like extravagant spending.

[JeffB]

TBG: That was a Misses size jacket from Sears which doesn't offer tall women's sizes, I don't think I could've gotten a shorter jacket unless I opted for Petite, and I seriously doubt that would fit.

As for the encounter with the trooper, that had taken me aback big time. I try as hard as I can to anticipate all manner of questions or comments people might pose to me when out and about so I don't sound like a stumbling fool, but that lady certainly accomplished that because I never thought she'd broach that sort of topic. Speaking of which, yeah, I guess it's still something of a stereotypical mindset that a man wearing women's clothes in public is either gay or transgendered, something that's not at all true, but the mindset still exists, but, freestyling folks like me are doing all we can to dispel that.

Lastly, you have a point there about being passive in regards to seeking attention while in public, whether I want to or not. If I tend to overdress on my outings, and I've done that lots of times, it's because I want to look good and present a proper image as a man in women's clothes and shoes. As for the meter, the parking authority here in Philadelphia (I call them The Parking Authority Gestapo) are, how shall I call it, overly enthusiastic about ticketing drivers, this is no exaggeration, it's like their soldiers appear out of the clear blue when time expires on meters. Better to be early than late.

P.S.: My new keyboard isn't quite that elaborate. Heh.

[Thighbootguy]

JeffB -  The style of jacket I had in mind is called a cropped denim jacket (I had to look that up).

 

Cropped Jacket Image

 

Like yours only ending at a line created bu having the bottom 2 or 3 buttons cut off.

[SkirtDude]

Jeff, I would not get too bogged down in the whys and wherefores, it could be that the state trooper liked you ♡

Jokes aside, sadly in our culture as people of colour, and Hispanic culture, guys just don't do that sort of thing without repercussions, either being ostracized, beaten up, accused of being gay, or worse. Look at the rough time Will Smith's son Jayden is getting now since he came out saying he prefers wearing women's clothing and has been seen openly in skirts and dresses. Sadly they are scared that society is trying to weaken or emasculate black men by getting more of them to wear women's clothing... from Yung Thug to Elephant Man, they are unsettled about those they looked up to embracing a wider range of fashion options. Even Usher is getting teased for wearing a kilt when he did a gig in Scotland. I think it's good its happening and the more men are seen just going about their daily routine in skirts instead of the regular jeans, the more they will have to get used to it and realize the world isn't going to come to its end... I note from your jaunts it's only the insecure in the safety of a group or from a passing car that shout things at you or laugh.

Your style suits you and now I understand the type of skirts you wear, having preferred the smarter 'office' type or more formal pencil skirt in the past, it seems chino or denim pencil skirts are more masculine and suit men better for day to day stuff. I'm buying more chino skirts and save the formal skirts for evenings out like if I am invited to dinner. For most house parties, I would wear a more casual skirt like a denim pencil or chino.

I enjoy your jaunts and you never know just who else out there does and may be now adding something more suitable to their clothing range like a skirt for the first time

Jealous also that you can get 2 hours parking for 5 bucks... in London, it's at least 5 bucks for half an hour, and the gestapo watch you by CCTV camera or chase you on a motorcycle to fine you if you exceed your time

Perhaps you should really push the envelope and go formal like TBG or myself in a tight sexy dress

Looking forward to your next jaunt

K

Don't worry about the encounter with the trooper... here's a pic of my new heels (teamed with my new stretchy chino skirt and grey tights) to take your mind off things

K

[AZShoeNut]

A great experience with the trooper. I feel for her and without too much assumption I suspect that your choice to wear what you enjoy helped her reconcile the loss of her brother in some way. Maybe consider it a Godwink for boldly expressing that which makes you shine.

[bluejay]

That was a nice look, JeffB.

I disagree with THBG, advise of wearing a shorter, cropped jacket. That jacket looked just fine with your ensemble It was not too long.

And your encounter with the Trooper, was certainly, a unique experience.

Thanks for the post and the pics too.

 

Happy Heeling,

bluejay

[JeffB]

Kilty: You're right about how men of color and Latinos do have it rougher than most when it comes to sexual preference and transgender issues. On the VERY few occasions (few enough to be counted on one hand with fingers left over) I had been heckled while out and about, it had been blacks who did the heckling, but I don't worry about that. As for my style, it's all about looking as nice and proper as possible when in public, I've come to truly appreciate pencil skirts for the slim and sleek profile they afford me, even denim styles make me look sharp, but I do have a few dressier styles which I've worn in the past and will wear again. As for wearing dresses on future outings, stay tuned!

 

AZShoeNut: Perhaps I did help that woman just by being there and wearing what I like, an experience I never expected to have taken part in. All things considered, that makes me feel good.

 

bluejay: Thanks for the kind words.

[mtnsofheels]

Hi Jeff,

 

Good for you being who you are and enjoying your outings. Good lookng outfits you continue to wear, you look really good in them.

Fantastic encounter with the State Trooper, very awesome experience to say the least. It would be so good to catch up with here and have a

engaging talk with her. Certainly the curiousity has gotten to me about her story, it was wonderful of her to share what she did with you.

It just goes to show all of us that just being ourselves and standing up for what we wish to wear and present can have untold benefits.

The more I find recently is many tips and words read all say the same, "just be yourself and go forward", "show yourself for what you are"

are so applicable and real right now.

As always, your are inspirational!

[JeffB]

mtnsofheels: Chances are I'll probably never seen that woman again as I saw that as a one in a million sort of encounter, but I'm okay with that. Meanwhile, I agree that being myself and doing what I like can indeed reap incredible benefits. As for who I am, I've already said this, I'm just a middle aged guy who likes wearing women's clothes and shoes, nothing more, and I'm fine with that as well. Still, it's good to know that I can be an inspirational figure for folks like yourself.

[JeffB]

Well, I've gone ahead and put away my sweaters, turtleneck and heavy winter skirts and brought out my lighter, spring and summer skirts along with my warm weather tops, including fifteen tanks in various styles and colors. Oh, yeah, with the warm weather here, that also means dusting off my wedge heeled platform sandals! Can't wait to wear them on future outings!

[JeffB]

Jaunt #259, 4/18/2015

Yesterday was easily the best day of the year so far, what with plenty of sunshine and temps that flirted with 80, EIGHTY! With that in mind, I happily went on a jaunt, dressed for the nice weather in a coral colored tank top with a lace insert, a knee length, button down denim skirt, the Payless "Nicole Chopout" platform wedge sandals and a black handbag. Needless to say, I felt damn good wearing that outfit and it was great to be out and about in sandals, and I plan to wear them lots this season. Anyhoo, I drove into center city, parked a block away from my friendly, neighborhood comic book shop, put five bucks in the meter for two hours of parking time and walked down to the shop where I spent nearly half an hour, chatting with the staff about the new Daredevil TV show and the trailer for 2016's Batman v Superman: Dawn of Justice (for the record, we weren't all that impressed).

 

From there, I took a stroll to Rittenhouse Park, absolutely jam packed with people enjoying the nice weather, despite my outfit, especially the brightly colored top, no one gave me so much as the time of day, finding a bench near a shady spot under a tree, I sat down, broke out my Barnes & Noble nook™ (that's an e-reader if you're curious) and read for about an hour and half while scores of people walked past, no of whom took any notice of me. It was very relaxing and pleasurable, reading, taking in the surroundings and just enjoying being among the masses, short and sweet, it was great fun. With fifteen minutes left on my meter, I leisurely strolled through the park, letting people see me, again, no responses which was cool with me, I was just another person taking advantage of being out in the fine weather. Back in the car, I drove over the bridge into South Jersey and Barnes & Noble for some quiet time, bought a sandwich and a bottle of lemonade and sat down with my e-reader and finished the book I was reading, spending nearly an hour there. My last stop of the day was to the nearby Dick's Sporting Goods where I bought a new air pump for my bicycle, and then, it was back home.

 

This was easily one of my most enjoyable outings as it felt great to be out in warm weather attire, and I enjoyed wearing my platform sandals which are such fun shoes as well. Of course, it goes without saying that being in a nice skirt that looks nice on me is what ties everything together. Something tells me this is going to be a great season for jaunting. More to come....

[SkirtDude]

Cute skirt, Jeff! I have always feared these as I'm afraid of a wardrobe malfunction and buttons popping open showing more than I wished to This and skirts with the slit at the front rather than at the back isn't for me, but that's just a preference. Lovely top as well as the sandals ♡

[JeffB]

Cute skirt, Jeff! I have always feared these as I'm afraid of a wardrobe malfunction and buttons popping open showing more than I wished to This and skirts with the slit at the front rather than at the back isn't for me, but that's just a preference. Lovely top as well as the sandals ♡

 

The possibility of a wardrobe malfunction never occurred to me when I bought that skirt, and I have three more just like it, I love the simplistic, casual styling with the front buttons, none of which have ever popped, and I'm fortunate for that. Glad you liked the top and the sandals.

 

And now, it's time for the first Sunday Doubleheader of 2015!

 

Jaunt #260, 4/19/2015, morning:

With the sun up, I headed out to the supermarket shortly after 8 a.m., attired in my denim jacket over a brown t-shirt, the Old Navy 21 inch tan chino skirt, the Payless "Genevieve" loafers in cognac and a brown handbag. I've been eager to take the new loafers I had bought little over a month ago for an outing, and I'm happy to have made the purchase as they were supremely comfortable and stylish with the gold buckle on top, and matched well with the tan skirt. These shoes also came in black, but Payless didn't offer them in 13 wide, a pity because I would've bought a pair if they had.

 

Anyhoo, there had been a good crowd at the market as evidenced by the cars in the parking lot when I arrived, but that was no deterrent as I hopped out of the car and walked on inside. Strolling the aisles at a leisurely pace as I sought the items on my list, I barely attracted any stares, which I was used to, after about half an hour or so of going about my business, I went to the check out lane, paid for my purchases, bagged my stuff, then left the market, pretty as you please, I was just another shopper, and that was good enough for me, I expected to be treated no differently from anyone else, and that was all I wanted.

 

Jaunt #261, 4/19/2015, afternoon:

The afternoon outing was a dirt simple case of having a screaming need to go out in a skirt and heels which had been on my mind from the moment I got back home from the supermarket. Despite plenty of sunshine, it was cooler than Saturday, even at high noon, so I headed out in my black faux leather jacket over a red t-shirt, my 16 inch black denim miniskirt, the Pleaser "Legend" thigh high boots and a black handbag. Admittedly, it had been quite some time since I last wore the five inch heeled boots and had to remember to take things slow at first until I had reacclimated myself to wearing them, but that didn't take long and I was having fun in them.

 

Heading west into the burbs, my first stop was to an Acme supermarket to shop for a couple of items I couldn't find on my shopping trip that morning. I also had to remind myself to take smaller, deliberate steps with a slower gait inside the store because of the polished tile floors, but I managed quite well while I looked for the items I sought, Fiber One protein bars and barbecue rice cakes, standing in line for a few minutes, I paid for my items and departed, having barely attracted any attention the whole time. Back in the car, my next stop was down the road to Best Buy, there was a fairly good crowd in the store as I entered, but that was no big deal to me, as I strolled the Blu-Ray aisles, I caught the attention of a black lady in her late fifties (I guess) who looked up at me and grinned, saying, "You're pretty tall, and those heels make you even taller." I grinned back and said, "I just want to stand above the crowd." The lady chuckled and said that I did. After another twenties minutes or so of wandering, I bought an anime title and left.

 

By that time, I was walking with a noticeable strut as I was having lots of fun wearing those boots with my short skirt, I felt good, damn good, because I was doing what I loved, freestyling, showing the world that a guy can break gender rules when it comes to clothing and look great in a skirt and heels when he puts his mind to that task. And that's my driving goal, to look my very best when in public, anything less would be a failure for me. More to come....

[Mr. X]

Loving the outfits Jeff!  Especially the latest black and red outfit.  It has an edgy rocker vibe to it.  Luv it!  If you ever go to a heavy metal concert you totally need to wear this lol  You would fit right in!  Again, well done!

[SkirtDude]

Love the tan skirt! You look so at ease in both outfits (though I'd struggle in those thigh high boots), and nice there was a positive comment. Tells me that really no one cares if you dress well and just go about your business. The tan skirt looks comfy, too it made me put on my one - I'm getting there with the poses and since joining a gym I'm feeling slightly more confident about my legs when I go out and about

Looking forward to your next jaunt as always

[bluejay]

JeffB,

 

Love your enbsembles that you wore this wekend. They all look great in you.

 

I have to agree, that your last ensemble with the red and black leather and thigh boots is a real "sizzler" look!!!!!!!

 

Today, I also did two heeling events too, just like you. First time out wearing, capri leggings with a pair of pumps, for my afternoon outing. Still too cool here, to be wearing sandals out, but hoping to do so soon.

I also bought a new off white, jean skirt, knee length, to wear out when it warms up.

 

Thanks again for the post and you great pics.

 

Happy Heeling,

bluejay

Love the tan skirt! You look so at ease in both outfits (though I'd struggle in those thigh high boots), and nice there was a positive comment. Tells me that really no one cares if you dress well and just go about your business. The tan skirt looks comfy, too it made me put on my one - I'm getting there with the poses and since joining a gym I'm feeling slightly more confident about my legs when I go out and about

Looking forward to your next jaunt as always

Kilty,

 

That skirt looks great on you. As I've been reading more of us men, here at HHP, are taking up wearing, skirts.

 

It's a lot of fun to wear a skirt out, with my heels.

 

Happy Heeling,

bluejay