The Jaunts of JeffB!

[SandalFan]

The dead LAST thing I need is to get in an accident and have to exchange insurance numbers while garbed in a skirt and heels. That would be a tad embarrassing. Food for thought.

And that's why I only wear men's clothes when street-heeling.

[JeffB]

Well, well! We sure do have some sharp-eyed members here at HHP! Heh! I've wanted to experiment with lipstick for awhile and thought yesterday was a good opportunity. And it wasn't an accident that I wore a shade that matched the shirt I wore because I wore said shirt when I bought the lipstick at Rite-Aid a couple of weeks ago, my goal being to blend in, not stand out, well, at least no more than I already do as a tall black man in a skirt and heels. All things considered, I thought I pulled it off well, given that was my first time having worn lipstick, and I thought it was fun too. Now, I'm sure everyone who saw me yesterday noticed, but no one said a thing, at least not to my face anyway. Perhaps I'll try some other subtle shades for public wearing in the future. TBG: To be honest, I would've been shocked if you hadn't suggested I wear boots. Patience, my friend, they're coming! HA! By the by, the woman's watch was another experiment, didn't pay all that much for it, just twenty bucks! SandalFan: Aww! Where's the fun in wearing men's clothing? HA!

[Thighboots2]

So Jeff, when you going to follow KH and Mal's lead and get down to the night/singles clubs and see how things pan out? It would be really interesting to see if you have the same sort of reactions that they have experienced. Simon.

[Bubba136]

8/25/2010: Postscript: While on my way back home, I passed by the scene of an accident, nothing serious, just a mild fender bender, but that did remind me of the importance of driving both carefully and defensively while on a jaunt. The dead LAST thing I need is to get in an accident and have to exchange insurance numbers while garbed in a skirt and heels. That would be a tad embarrassing. Food for thought.

After reading the above, I wondered why being involved in any one "true life" situation would be more embarrassing than being involved in any other, regardless of what a person was wearing?

I daily wear my woman's shoes in public. And, while I've occasionally thought of how I would feel/react if an unusual situation that exposed or brought added/unwanted attention upon me occurred or happened, my conclusion each and every time that I thought about it was that that is the chance I am taking whenever I leave my home and venture forth into great outside world wearing any style of woman's shoes.

Would I be embarrassed if something "untoward" occurred? Probably. But then, if I am willing to expose myself to disparaging, belittling, demeaning and humiliating comments from members of the general public while engaging in normal activity, why should I be more embarrassed if I become involved in something requiring "longer than" usual exposure? If I am, then I have no business dressing in any fashion other than what the general public accepts as "normal."

Personally, I feel that if anyone is going to wear any kind of "alternative" garments or footwear in public then they should be in a frame of mind to accept and handle whatever occurs without added embarrassment. If they are not, then they have no business venturing into the unknown dressed in any manner that would be even the slightest embarrassing.

[JeffB]

8/26/2010:

A new day, a new jaunt, and a new twist thrown in for good measure as I wore women's garments from head to toe. Here's my outfit:

A purple polo shirt from JCPenney, the long black A-line skirt from Old Navy (yeah, I know it's seen a lot of action lately, what can I say, I just LOVE wearing that skirt!), the Payless "Hazel" pumps, my short strap handbag and my new woman's wristwatch. As for my outing, I went to someplace new, a place where I've never even worn just heels before, never mind heels AND a skirt----a casino! To be more concise, the new Parx Casino near Philadelphia race Track in the Northeast. Ever since it opened, I had been curious about the place since I indulge in a wee bit of gambling from time to time, so, just for the sheer hell of it, I decided to make that a jaunt. Getting there took something like half an hour, from outside, the place looked plenty ritzy, complete with a humongous parking lot, climbing out of the car, I casually strolled to the casino and went inside where I was greeted by the typical bells and whistles and jangling of slot machines and the recently added action of table games like poker and blackjack. I must say it was mighty impressive.

I did get a few looks and glances from guards and other personnel, but that was it as the customers were busy gambling. After standing in line waiting a good ten minutes for a Parx Card, I went about my own business of waging war with the one-armed bandits, after little over half an hour on a penny slot machine (being smart, I kept my handbag in my lap so it wouldn't get swiped or wind up with someone's hand in it other than my own), I got lucky and wound up with little over $154 bucks. WHOO!! Big money for me since I rarely get lucky on the slots. After cashing in my winnings, I pocketed the Benjamin and played with what was left, spending a good two hours in the place where I had fun and was paid next to no attention before I decided to take my leave of the place. All things considered, I enjoyed Parx and plan to visit it again soon. Whether or not I return in a skirt and heels is purely up to my discretion. It was a great feeling to go on a freestyling jaunt to someplace new, the excitement I felt was palpable and made the experience memorable.

It was about three p.m. when I left, but I wasn't ready to head back home. It felt good to be freestyling, so I decided to extend my outing. So, after returning to the city, I headed into center city and my favorite comic book shop to buy this week's new books, took awhile to find a parking space near the store, but after I did, it was off to the store where I spent nearly half an hour in the store ogling over the new books and yakking with the staff about the latest and greatest comics, there were almost a dozen people in the store, but no one paid a whit of attention to how I was dressed, something I thought was cool. After leaving the store, I still didn't want to go back home, I was having too much fun, and that had everything to do with my outfit, the pleasurable feeling of the skirt swishing about my legs while I walked and, of course, the clicking of the heels on the pavement, all of which combined to make me feel good about myself and about being out in public dressed the way I want to dress, not how society wants me to dress. I love that boldness.

So, just for fun, I headed out to the western 'burbs, first to Subway for dinner, the place was empty at nearly six p.m., so I had the place all to myself while I ate my dinner sandwich. Then, it was off to Borders for some quality time in the lounge area with some magazines, including a Rolling Stone special edition on the 100 greatest songs by The Beatles which made for tremendous and fascinating reading. If you're a fan of the Fab Four, by all means, find that mag, it's great stuff! By the time I finally decided to call it a day, it was almost 8 p.m., pretty remarkable for me since I'm rarely out after dark, but I was plenty happy after one of my longest jaunts ever. It just felt so incredibly good to have spent the day in a skirt and heels and acting perfectly normal like it was no big deal to be a man who was boldly wearing women's clothes in public, and for me, it wasn't. This is me, this is who I am, and I have no intention of denying that truth. More jaunts to come!

[Thighbootguy]

"It was about three p.m. when I left, but I wasn't ready to head back home. It felt good to be freestyling"

Isn't it great when it works that way. I know for some of our members just the thought of going out is terrifying

Isn't it great when it works that way. I know for some of our members just the thought of going out is terrifying but they miss all the real enjoyment of being out. Enjoyment, rather than excitement, is the operative word. Exciting tends to raise your stress level where enjoyment tends to lower it.

Sounds like you had a great time and have found another fun place to go and looking good too.

[JeffB]

Isn't it great when it works that way. I know for some of our members just the thought of going out is terrifying but they miss all the real enjoyment of being out. Enjoyment, rather than excitement, is the operative word. Exciting tends to raise your stress level where enjoyment tends to lower it.

Sound logic there, TBG. I had so much fun yesterday, I just didn't want the day to end. And yes, I did indeed enjoy myself. In fact, as I was driving home last night, all I thought about was my next jaunt as adding skirts to the equation has increased my joy of freestyling exponentially.

[skirtedvik]

About your last pictures - This style suits you no matter what people think!Nice outfits.True freestyler...

[JeffB]

About your last pictures - This style suits you no matter what people think!Nice outfits.True freestyler...

Thanks for the kind words. I appreciate them. Yes, I certainly enjoy my current style which I do indeed think suits me well. And, more importantly, I'm having lots of fun with my freestyling.

[roniheels]

I love your new outfits. They look cool, comfortable, and should blend right into Autumn. When many us of wear high heels in public, without getting too giddy, you want to relay to the site members just how much fun, exciting, adventurous, and satisfying it is. You and many others who share their experiences with us are a continued inspiration.

I will be participating in a Walk-a-mile-in-her-shoes event and will let everyone know how it goes. I also have Thursday off work this week and I will be out-and-about all day in high heels. I'm always looking forward to those days and my agenda.

Thank you again for the wonderful post. Please keep them coming.

[JeffB]

8/28/2010:

A Saturday in late summer with the weather warm, the sun bright and the skies blue presented the perfect conditions for a casual jaunt. Here's the outfit I wore:

A black polo shirt from JCPenney, my 22 inch denim skirt, two inch heeled loafers from Payless, bare legs and my Buxton Bag. If the weather had been say, ten degrees warmer than the high of around 85, the black shirt might have been a bad idea since dark colors absorb heat, but with precious little in the way of humidity, it was safe to wear black, and that shirt paired well with my skirt. My goal for this outing was to push the envelope a little further than I had previously done, by cruising through a mall. The mall in question was Cherry Hill, after arriving just before noon, I took a few deep breaths to steel myself, grabbed my bag and left the car. I entered the mall through Penney's which emptied out near the food court, and that was the first place I went since I was hungry and it was time for lunch. The dining area was fairly well packed, but very few people bothered to even give me a cursory look as I stepped in line at Subway and ordered a footlong meatball sandwichich, casually went to a table, sat down and ate.

After I finished, came the next step, walking through the mall itself, crowded with people. But again, I garnered very little attention as I meandered my way through, no wide eyed stares, no gaping mouthed expressions, no neck twisting double takes, no wild laughter, nothing at all I found that to have been pleasurably surprising, and just plain pleasurable as I wasn't bothered or heckled. I would spend nearly forty-five minutes in the mall, most of that time in the Apple Store since I'm a Mac user. On my way back, I did some shopping at Penney's, buying a couple of new polo shirts, again, no muss, no bother, no nothing, I was treated just like everyone else. Upon leaving the store, I headed down the road to the Barnes & Noble bookstore near Moorestown Mall where I spent nearly an hour cruising the aisles in a far more quiet and serene environment than the crowded mall, but nothing changed as practically no one gave me the time of day, I just went about my business of checking out manga, graphic novels or magazines to buy.

Stop three was to Best Buy nearby, like the mall, there was a darn good crowd there, I spent another solid half-hour, ogling all the gadgets that I love staring at, to me, that's great fun, by the time I went to the check-out lane, I had Blu-Ray versions of the original Planet of the Apes (far better than the crappy Tim Burton remake) and House of the Flying Daggers. But my day wasn't over as I had one more push to do: wandering around downtown Philly. After driving back over the bridge into town, I steered towards Center City, parked near Rittenhouse Square and climbed out, my goal, to be seen and see what would happen. Walnut Street in downtown on a Saturday afternoon is a huge, writhing mass of people shopping, dining outside or chilling out in nearby Rittenhouse Square park, and there I was, pretty as you please, even though it was plainly evident I was sporting a skirt and women's shoes, and yet, nothing happened, again. Even though I was more than a tad nervous, I maintained my usual calm and casual air.

I spent nearly forty-five minutes in the area and found the experience rewarding as I mingled with that sea of humanity and no one gave a damn about how I was dressed. In short, I had a great time from start to finish on this jaunt which was an important one since I successfully pushed that envelope in my freestyling. More exploits to come.

[Bubba136]

That looks really comfortable, Jeff. It looks almost the same as the outfit that you wore on your trip to NYC a year or so ago. And, if I recall you didn't create much attention on that excursion either.

[roniheels]

That is a good looking, comfortable looking outfit. And it sounds like you had another fun, successful jaunt. I can se why you probably didn't get too many glances. The denim skirt could almost pass for long, baggy shorts. And with people in such a hurry these days, I can see why no one gave you a second look. Great post and may you have many future successful jaunts!

[JeffB]

That looks really comfortable, Jeff. It looks almost the same as the outfit that you wore on your trip to NYC a year or so ago. And, if I recall you didn't create much attention on that excursion either.

Well, given how jaded New Yorkers are, I could've worn a pink sequined evening gown with a Miss America tiara and no one would've given me so much as the time of day! HA!

Thanks for the kind words, roniheels. I think someone else had mentioned how that skirt could be mistaken for shorts. Perhaps! And yeah, that outfit was comfortable.

[ShockQueen]

Definintely a cool outfit, JeffB! I'd love to see some outdoor shots of your jaunts - sort of a 'travelogue' type of pic. Thanks for another incredible jaunt!

[JeffB]

Outdoor shots, eh? Well, I'll see what I can do about that!

[JeffB]

8/29/2010:

Just a short jaunt today as I sought to break in the new shoes I bought at Payless on Friday. Here's the shoes:

These are the Dexter "Karma" pumps, and here's the outfit I paired with them:

A white polo shirt from JCPenney (bought on Saturday), the 20 inch black skirt from Old Navy, bare legs and a black handbag. I found the shoes to have been very comfortable, thanks to the roomy, rounded toes while the four inch heels (measured from the back) made for easy walking, and were delightfully firm and solid sounding on the pavement as I walked. Anyone familiar with me knows I like my heels good and loud, and these shoes made the grade in my book. I only made two stops today as I went back out to the western 'burbs, my first stop being to Subway in Springfield for lunch. What can I say? I love Subway! The store was empty as I entered, so I had the place all to myself as I placed my order (a six inch turkey breast and black forest ham on wheat) and ate while reading the sports section. After I finished eating, it was off to Borders for some reading. As usual, I parked a good distance from the store so I could enjoy a long little walk and enjoy the authoratative sound of the heels on the pavement.

Just as I reached the door, it opened and two black women around my age came out, one, her hair mostly gray, looked me up and down, then said, "First time I've ever seen a man in a skirt. You look nice, honey. Love the shoes. Where did you get them?" When I told her they came from Payless, she said she would have to look for a pair the next time she was in a store and thanked me for the info. I grinned and returned her thanks for the compliment. Her friend chuckled, saying she'd break an ankle wearing heels as high as mine and was impressed with my skill. I replied that all it took was lots of practice, and she laughed, agreeing on that point. Not bad. Always cool to get a compliment, and I felt good the whole hour plus I was in the lounge reading magazines. That little encounter was more proof that there are openminded people in this world who are willing to accept alternative forms of fashion, especially older people who should be more narrowminded, but those ladies were clearly the exception to that particular rule.

I was still feeling good as I left the store. The more I go out on jaunts in heels and skirts, the more comfortable I become, I still feel I have a ways to go before I feel confident enough to go anywhere, but I'm not going to push myself, I'll just let things come in their own good time, and have fun in the process.

[Heel-Lover]

Hi Jeff, Awesome report. Love the heels and love the skirt. You're absolutely right about the more you wear them the more you comfortable you become! I too love the sound of my shoes - why not let them be loud? - High heels are a 'loud' looking statement shoe anyway - so it suits them to be loud. Your skirt length is my favourite length too - and you're lucky to have good legs to let you wear a mid-thigh straight skirt like that! I approve of the handbag touch - its practical and it coordinates/ balances the look! Awesome reading. thanks Heel-Lover

[JeffB]

Greetings, Heel-Lover! Thanks for the kind words! I forgot to mention this in my report, but I initially thought about pairing the new shoes with dress pants, but the look just wasn't right, in my mind, those pumps worked best with a skirt, and since I regularly wear them on my outings now, it was a logical choice for me to have made. I also feel lucky to have the legs to wear skirts, just wait until Fall arrives, the weather cools and you see me wearing hosiery! Whoo!

[JeffB]

8/30/2010:

Well, here I go again with yet another jaunt, my FIFTH in the last six days, and I'm certainly having a whole lot of fun! Here's today's outfit:

A forest green polo shirt, a 20 inch button down black denim skirt (both from JCPenney), the Payless black "Hazel" pumps, bare legs and my black handbag. Once again, I decided to push the envelope a tad by going into Center City, returning to Rittenhouse Square where I was on Saturday. Unlike then, it wasn't nearly as hustling and bustling with people when I arrived around 10:30 a.m. since today was a workday, after parking and feeding the meter, I casually strolled a couple of blocks down to Barnes & Noble and went in to upload a couple of e-books to my B & N Nook™ e-reader. With a tall glass of iced tea, I sat in the lounge area and read a couple of chapters of the original Frankenstein (which I downloaded for free) for about an hour, which was about the time I had on the meter. Not wanting to wind up with a ticket, I returned to the car and zipped over the bridge into South Jersey for some more goofing off.

I arrived at the B & N store near Moorestown Mall a little after noon, since I wasn't hungry, I skipped lunch and read some more until about 12:40, then packed up and went over to the mall to catch the 12:50 showing of Sly Stallone's latest popcorn flick, The Expendables which I thought was a hoot and a half. Ahh! Nothing like an afternoon spent watching 1980's action heroes blowing stuff up and killing bad guys! Tons of fun! After the flick ended, I passed by a trio of teenagers, one boy and two girls in the lobby, don't think any of them were older than 14 or 15 if that, well, they promptly broke out laughing when they saw me, but I didn't say anything or even turned around to acknowledge them, that would've been a waste of time, and life's too short to engage lowbrow fools in senseless banter. The funny thing is that while I was neatly dressed, those kids looked like total slobs. Maybe I should've laughed at how THEY were dressed.

I could've stayed in South Jersey longer, but I wanted to get back over the bridge and into Philly before the traffic snarled up since it was in the early stages of rush hour. Still, it was another enjoyable outing, one not even those teen turds could spoil with their laughter. I'm sure I gave them all a cheap thrill, and by nightfall, they will have totally forgotten about me, given the ridiculously short attention span today's teens have. Another day, another successful outing.

[roniheels]

My friend, you are on a roll. Those are some great outfits coordinated with your high heels. And your jaunts have been interesting, informative, and entertaining. Keep up the great work and keep having fun.

[Heel-Lover]

Hi Jeff, Well done yet again! Those heels are so cute. I just love fine stiletto style medium heels like those, they are just so cute. Only prob is not getting them stuck in pavement cracks!!! Cheers Heel-Lover

[JeffB]

roniheels: Thanks for the kind words! I have been having fun of late, and, at the risk of being dreadfully repetitive, adding skirts to my outings in heels is the reason for all the fun. I feel at home and at ease wearing skirts in public, and it's rather exciting too! I'm glad that I've kept you reading with my little adventures. I'll do my best to keep you and everyone else reading! Heel-Lover: Yeah, I love those pumps too! The three inch height is perfect for more casual outings and they're so easy to walk in too! Makes me wish I had bought an extra pair as I've been wearing them to death lately! Those devilish pavement cracks are indeed a menace to be avoided at all costs!

[skirtedvik]

8/30/2010:

Well, here I go again with yet another jaunt, my FIFTH in the last six days, and I'm certainly having a whole lot of fun! Here's today's outfit:

A forest green polo shirt, a 20 inch button down black denim skirt (both from JCPenney), the Payless black "Hazel" pumps, bare legs and my black handbag. Once again, I decided to push the envelope a tad by going into Center City, returning to Rittenhouse Square where I was on Saturday. Unlike then, it wasn't nearly as hustling and bustling with people when I arrived around 10:30 a.m. since today was a workday, after parking and feeding the meter, I casually strolled a couple of blocks down to Barnes & Noble and went in to upload a couple of e-books to my B & N Nook™ e-reader. With a tall glass of iced tea, I sat in the lounge area and read a couple of chapters of the original Frankenstein (which I downloaded for free) for about an hour, which was about the time I had on the meter. Not wanting to wind up with a ticket, I returned to the car and zipped over the bridge into South Jersey for some more goofing off.

I arrived at the B & N store near Moorestown Mall a little after noon, since I wasn't hungry, I skipped lunch and read some more until about 12:40, then packed up and went over to the mall to catch the 12:50 showing of Sly Stallone's latest popcorn flick, The Expendables which I thought was a hoot and a half. Ahh! Nothing like an afternoon spent watching 1980's action heroes blowing stuff up and killing bad guys! Tons of fun! After the flick ended, I passed by a trio of teenagers, one boy and two girls in the lobby, don't think any of them were older than 14 or 15 if that, well, they promptly broke out laughing when they saw me, but I didn't say anything or even turned around to acknowledge them, that would've been a waste of time, and life's too short to engage lowbrow fools in senseless banter. The funny thing is that while I was neatly dressed, those kids looked like total slobs. Maybe I should've laughed at how THEY were dressed.

I could've stayed in South Jersey longer, but I wanted to get back over the bridge and into Philly before the traffic snarled up since it was in the early stages of rush hour. Still, it was another enjoyable outing, one not even those teen turds could spoil with their laughter. I'm sure I gave them all a cheap thrill, and by nightfall, they will have totally forgotten about me, given the ridiculously short attention span today's teens have. Another day, another successful outing.

Maybe a "women's" top might be a better option.I liked your style with the purple one, may be buy something else like a nice blouse.

[JeffB]

8/31/2010:

A few months ago, I mentioned that I had bought a pair of capri pants which I planned to wear on an outing with heels. Well, here's that outfit for today's jaunt:

A blue polo shirt, the aforementioned capri pants (both from JCPenney), the Payless "Hazel" pumps, bare legs and a new short strap handbag as the strap on my previous one had broken the other day. I'm sure everyone here is shocked thinking, "Wow! Jeff's not wearing a skirt! Is he sick or something?" HA! Nope! I just wanted to take those capri pants for a spin and see what they were like. Well, they fit snug but not too snug and were quite comfortable to wear. Also, at the risk of sounding boastful, I thought they looked good on me with my long legs, pairing them with heels only improved the overall image. So, today, I headed out west again to the Borders inn Springfield, but this time, I had my laptop with me and I spent nearly four hours in the lounge indulging in some writing. The store was rather quiet, more quiet than normal and that leant to a relaxing experience as I busied myself tapping away on my machine. By around two, I decided it was time to eat, so I packed up and went down the road to Subway for a late lunch.

My next stop was further out west to Micro Center (a computer store chain) where I needed to buy a USB hub for my computer. Just like Best Buy, I love to wander the aisles and ogle at stuff, the store was mildly busy with customers, but while trying to decide what hub to buy, a guy purposely stared down at my feet as he walked by, openly frowning as he did. Even after he was a good ten or so feet away, he looked back to stare again at my feet. he didn't say anything, didn't giggle, chortle or chuckle, he just stared. I'm sure I must have made for quite a sight. And wouldn't you know it, just a few minutes later, another guy stared at my feet, looking openly perplexed. I found it rather humorous, if anything, I thought people would take notice more of my pants than my shoes, oh well, what do I know? Heh! That just goes to show that society still has a wee bit of a hangup over men wearing women's clothing and/or shoes, if a woman were seen wearing combat boots or wing tips, no one would give her so much as a glance, but a man standing tall in high heels is still something of an oddity to the world at large.

Well, that's the world's hangup, not mine. This is the main reason why I go to great lengths to look as stylish and tasteful as humanly possible when on my outings so I can present a proper and positive image of a true fashion freestyler instead of being seen as some sort of freak or deviant just because I choose to wear women's clothing and/or shoes. While to tiny segments of the populace with closed minds who are unable or unwilling to expand their horizons, they'll see me as an object of derision regardless of how well I'm dressed, but to those willing to accept alternatives in fashion, perhaps they'll see me and say, "Who cares if he's wearing a skirt and heels, he looks good!" That's my goal.

[Mr. X]

Very nice outfit Jeff. It is quite stylish. And it suits you to a tee. The blue colour of that top is great and it really suits you. And those capris look great too. Capris are hard to pull off. I have seen many a women wear them even though they shouldn't. I have tried them and they don't always look right on me either. It takes a certain body to pull them off. Apparently you have one of those bodies, well done!

[danielp6406]

Greetings JeffB :-)

A nice outfit and matching heels.

I bet the two guys looking at your feet were saying to themselve

"I wonder how it would feel like to wear these shoes. What a lucky guy he is.."

Well done !

[roniheels]

Love the capri's, the top, and the high heels. And the reactions from the guys, like you said that's their problem. Best to you on your next outing.

[Thighbootguy]

JeffB -

The capris look fantastic! I like that look even better than the skirt especially with the pumps. I think it was the combination of shoes and capris that caught the guys attention. The capris are slim and emphasize the leg and the heel has a similar effect of emphasizing the leg, and as you have pointed out those legs don't look bad to start with.

I was going to relate my experiences wearing capris but since I was wearing them under thigh boots, it isn’t quite the same thing. The tight pants emphasize the leg but so do the boots. I find capris very comfortable to wear, with or without boots.

[Steve63130]

Nice outfit, Jeff. I also like the capris better than skirts on you. It's definitely more attractive, especially with heels. Staring doesn't mean disapproval. Nor does frowning. It was apparent that these guys have only two pigeonholes in their heads - one for men and one for women. What was observed didn't quite fit into either hole, and the perplexing frown could have been more of an indication of frustration and not understanding than one of disapproval. Unless you open a conversation and ask what the other person is thinking, you can't know for sure. Capris are fun. I own 3 pair myself and enjoy wearing them! Keep up the good work! Steve