The Jaunts of JeffB!

[scrappycoco]

7/4/2010:

And here's where I had an interesting little encounter. While fiddling with the Nook, I noticed out of the corner of my eye, a middle aged black woman dressed like someone twenty years younger in a purple midriff top, a matching short shirt and high heeled sandals gave me a noticeably sour look from twenty feet away before slinking off, but I paid her no mind as I was long used to such expressions. However, ten minutes later, that same woman walked up to me, hands on hips and looking annoyed, she asked me the following question: "Do you know who Mickey Mouse is?" Unprepared for such an unusual inquiry, I asked her to repeat the question, she said, a tad louder, "Do you know who Mickey Mouse from Disneyland is?" When I replied that I did, she retorted, "Good! Because he knows that he's a boy!"

Jeff I give you a pat on the back for how you handled the women:clap: I don't think I myself would have been able to handle her like you did. My thoughts or should I say comment to her would have been along the line's of " Since when did old women start shopping in the teenager's clothing? And didn't I just see you on people of walmart?" I know this wouldn't have been the best course of action to take, but when someone like that would have come at me and insult's me like she did you I would not be able to control myself! I guess that is my sarcastic nature who know? Anyway nice out fit and keep it up!

[JeffB]

skirtedvik: Yes, I've come around to the concept that the odd juxaposition of pairing male attire with female attire simply doesn't work, or, at the very least, it doesn't work well. That said, I'm starting to think I should go ahead and stock up on feminine tops since I'm wearing skirts almost exclusively these days anyway. scrappycoco: Well, I'm not a confrontational person by nature, so the snappy comebacks you mentioned would never have come to mind. Besides, I was so stunned by what that fruit loop had said, I'm amazed I managed to respond at all. It was just an odd experience from start to finish.

[JeffB]

7/5/2010:

Since I had the day off from work, and was eager to go on another jaunt, despite a forecast with temps reaching well into the upper 90's, I headed out that morning, wearing what I call my "monochrome" outfit:

A white ribbed shirt, my 19 inch black denim skirt from JCPenney, my black faux croc print handbag (I certainly do I enjoy the pleasant heft of a full handbag on my shoulder), bare legs and the Payless "Hazel" pumps which have been getting quite a workout of late, but I love those shoes and the delightfully sharp clicking of the heels when I walk. When I headed out shortly after eight a.m., it was already in the low 80's, so I know it was gonna be a steamy kind of day, and that made my wearing a white top essential since light colors reflect heat instead of absorbing same as dark colors do. So why didn't I wear a lighter colored skirt you ask? Well, I look good in black! Vanity after all! HA!

Stop number one was to a place I don't think I've ever haunted...Starbucks. But I decided to give the place, halfway between home and downtown Philly a try. Going in with the paper, it was refreshingly cool, just what the doctor ordered, there wasn't much in the way of a crowd because this was an off-day for lots of people, just half a dozen customers or so. I strolled up to the counter where I was warmly greeted by young lady with freckles and glasses, I ordered a tall lemonade and retreated to the lounge area to drink and read. There was no particular reason I chose to go to Starbucks, I just wanted to be seen. Some twenty minutes later, the young lady who waited on me walked up to me, curiosity written all over her face, predictably, she said she couldn't help noticing that I was wearing a skirt and heels and, predictably asked why. With a shrug, I said "because I like to". Then she asked if I worried about being laughed at because I was wearing women's clothes and shoes. I responded by asking if she gets laughed at while wearing jeans, which she was. She chuckled and said she didn't and I said, neither do I. She ended the chat by saying she had never seen anything like me before, but that I looked comfortable in my attire.

After yesterday's straight out of the Twilight Zone confrontation with that loopy woman in the Moorestown Barnes & Noble, this was a pleasant change of pace. About an hour later, I was on the road again, this time, I was off for center city and the Barnes & Noble, parking on the street in the downtown area was normally next to impossible, but since this was a holiday for most, I was able to park right in front of the store which sat across from Rittenhouse Square Park, a trendy spot in the downtown district where folks chill out and whatnot. After parking, I simply hopped out and crossed the street to the store and entered, when I'm in my comfort zone, I tend to forget that I'm wearing women's attire, I'm simply wearing clothes that society assigns gender labels to. While I turned a few heads here and there (again, I'm long used to that), I found a comfortable seat on the first floor and busied myself downloading a few e-books to my Nook which I brought with me, then went up to the third floor where the sci-fi and fiction books were to get a few ideas for new titles to add to my e-reading list. I saw myself as just another shopper enjoying some quality time browsing the aisles for books that I want to read. Nothing more.

Between that and some casual perusing of magazines back on the first floor, I spent nearly an hour there, no interruptions or anything like that. By the time I left, it was around ten thirty, I decided to head out to the western 'burbs to kill a little more time before lunch. After stopping off at a gas station to fill up, it was off to Best Buy to ogle at gizmos, a favorite hobby of mine. Granted, compared to everyone else who wandered the aisles, both male and female, I was perhaps more than a bit overdressed, but hey, I didn't mind that, call it the price I pay for always wanting to look my very best. I spent nearly an hour there before coming out with a trio of Blu-Ray discs, and then, I headed down the road to Subway for lunch before calling it a day and heading back home. All in all, it was a good outing, despite the heat, an outing made even better by that chat I had with the girl in Starbucks. The difference between what happened on Sunday and what happened today was like night and day, proof positive that some are closeminded towards men breaking the shackles of conventional fashion while others are open to the concept.

[danielp6406]

Greetings JeffB :-)

Two great outings you did yesterday and today.

I like both skirts. The long skirt is very nice.

( You are giving me the idea to try one to see how it is like ... )

As always, I admire your confidence and assurance on your outings.

A note about you last outing with the short skirt: You are wearing a white tee shirt ?

Maybe the t-shirt is too "relax" to wear with such a nice skirt and heels ?

What about trying a white blouse next time ?

Happy heeling and please keep posting !

[JeffB]

A note about you last outing with the short skirt: You are wearing a white tee shirt ?

Maybe the t-shirt is too "relax" to wear with such a nice skirt and heels ?

To answer your question, it's hard to see details in the picture, but that shirt was ribbed, giving it a more fashionable appearance than a plain old T.

What about trying a white blouse next time ?

I'm thinking of taking that suggestion under serious consideration!

[Thighbootguy]

Going out sure is contagious, isn’t it. Sounds like you had a grand time and the black and white outfit looks good. I studied graphic art for a while and quickly learned I didn’t know how to work with color. I also didn’t study long enough to learn how to either. But with that caveat, maybe a red belt or a plain gold necklace, would have added a bit of splash.

[Heel-Lover]

Hi Jeff, Love both looks! Well done. Your longer skirt has a lovely shape to it and your belt and top coordinated really well. The second look with the shorter skirt and white t-shirt looks great. A mini skirt style in my opinion is ok with a t-shirt like you've done because its more casual than formal. A formal skirt look is usually just on the knee. I can't wait for summer here because I know what the shorter skirts are like to wear, they're quite cool (in more ways than one) and its nice to get your legs out (esp. since guys fashions are quite the opposite). You've got the skirt lenght just right, I find any shorter can be a nuisance for practical purposes and you've a great pair of legs! Your heels are cool, nice and pointy and they suit the outfits well. A great pair of ensembles!! Heel-Lover

[JeffB]

7/11/2010:

After a soggy and downright miserable Saturday with rain a goodly portion of the day, Sunday turned out quite nice, still hot, but not as oppressively humid as it had been during the week. So, with that in mind, it was time for a jaunt, and this one turned out to have had a special significance for me, given my outfit as, for the first time ever, I wore nothing women's clothing from head to toe:

A blue women's tee from JCPenney, the long black Old Navy skirt, my faux croc print handbag and the Payless "Hazel" pumps. Oh, yeah, and for whatever it's worth, I wear women's French cut briefs under my clothes. A comment by kneehighs about the shirt I had previously worn with this skirt prompted me to buy a few tops from the women's side of the store and see how one of those would work with the Old Navy skirt which I've fallen in love with because of it's light, breezy feel and how it swirls about my legs as I walk. I'm quickly starting to think of this as my favorite summertime skirt. In fact, I might just go back to Old Navy and see about getting this is another color, like blue or brown. But I digress, I felt no apprehension about going out and about dressed entirely in women's clothes, I was at peace and comfortable in what I wore. if anything, this might well have become the next phase in my ongoing exploration of fashion freedom.

Anyhoo, as for my jaunt, I headed east. Newspaper in hand, I headed for the Starbucks store near downtown where I spent a delightful hour with a tall lemonade while reading my paper, the store was fairly full, mostly with young people, probably college students, but no one made a big deal about how I was dressed, even while I sat among them. Oh sure, they probably had some interesting thoughts rattling around in their heads as they saw, casual as can be, legs crossed in a feminine manner and having a good time catching up on the news, but hey, I can't stop anyone from thinking. I might just make that a regular stop on my jaunts from this point on. From there, it was off to the wilds of South Jersey where I headed for Barnes & Noble in Moorestown to see if there was any new manga in stock, a nice little breeze blew the skirt like a flag while I walked to the door, catching the attention of a couple who did a rather comical double take as I strolled by. They didn't say anything to me, and I didn't say anything to them. Two ships passing in the night.

I spent a good half hour or so in the store, picking up a couple of manga titles and otherwise enjoying the experience of being surrounded by books. Ahh, bliss! And no crackpot lady chiding me with a Mickey Mouse reference like last week. From there, it was off to the nearby Best Buy to see what was new there. Being in a quiet, sedate atmosphere like a bookstore is one thing, but a large, noisy and crowded big box like Best Buy was quite another, and I'm sure I turned more than a few heads during the time I spent there, but no one said so much as a peep while I wandered the aisles. Despite the fact I probably came across to them as an oddity at best, a nutjob at worst, given how I was dressed, people gave me my space like they would any other human being, and that's just what I was. Who cared if I wasn't dressed in the way society says I should dress. Kill that noise! I'm having much more fun turning convention on it's all ear!

It was fun, pushing the envelope just a bit further with today's jaunt. There was no self-consciousness, just a sense of contentment because I chose to present myself in the way I wanted, not how someone else believes I should. And if I gave the people who saw me a cheap thrill and something to talk about with their friends for a few minutes, then I'm glad to have livened up their dull and insignificant little lives. I'm just spreading cheer and good tidings everywhere I go! HA!

[Bubba136]

JeffB. While I commend you for your courage and nonchalant manner going about your business while dressed in skirts and heels, I really don't like the last outfit. It's too boxy looking. No shape. Take a look at the white t-shirt and black skirt you previously wore. The clothes fit your frame better. You have some "shape". Clean lines and neat in appearance. Just my opinion.

[JeffB]

JeffB. While I commend you for your courage and nonchalant manner going about your business while dressed in skirts and heels, I really don't like the last outfit. It's too boxy looking. No shape. Take a look at the white t-shirt and black skirt you previously wore. The clothes fit your frame better. You have some "shape". Clean lines and neat in appearance. Just my opinion.

Hmm! Interesting! Never thought of it that way. Clean lines, eh? Well, that's certainly something else to take into consideration. To be honest, I never thought of myself as having some "shape". Heh! Anyhoo, thanks for the comments.

[Heel-Lover]

Hey Jeff, Well done! I love your look! I know what Bubba means in his previous comment as I think the same of myself sometimes when I dress similar to you but.... you just can't beat the feeling of wearing a nice pair of heels and skirt openly and honestly as we do. Even my most fitted outfits don't give me any real 'shape' and I think this is a good thing for men in heels because I certainly am not (and I imagine you aren't either) trying to be too overtly sexy. I do enjoy being a flirt at times because ... well because I can ... if I feel like pairing a short skirt and very high heels. Unless others are getting out there like us they won't know what I mean, won't know what they're missing. Cheers Heel-Lover

[skirtedvik]

That is better - the top suits you in my opinion!I wear even more "feminine" looking tops.The only condition is that they must not have bra-like parts (or cups) in them.Some models have integrated such parts and they are completely unappropriate for a guy.Apart from that all "female" upper clothing is appropriate for men. Remember that you must compare yourself and your look to other males (wearing similar items) and not to women.

[danielp6406]

Greetings Jeff :-)

The blue women's tee from JCPenney is much better looking than the white t-shirt.

Maybe next time, you would like to try one size smaller to see (and feel) the difference ?

Well done !

[rxrenesis]

Greetings JeffB, Nice outfit. I wanted you to know you've inspired my skirt wearing. Did a road trip not long ago and wore a skirt the entire trip. I was able to shoot a few pix on a pit stop. rx

[JohnH]

Greetings JeffB,

Nice outfit. I wanted you to know you've inspired my skirt wearing. Did a road trip not long ago and wore a skirt the entire trip. I was able to shoot a few pix on a pit stop.

rx

No big deal for me. I wear a skirt almost all the time!

[shortskip]

Hello Jeff, I think the same as Bubba said... Many pictures in the past gave a better shape of your body and your stile. Shortskip

[JeffB]

Well, having sported a belt helped a good deal with past outfits I've displayed, giving me that so-called "shape". However, I felt more comfortable without the belt in my last outfit, and considering how hot it was that day, that meant a whole lot to me. To be honest, I'm not sure I can achieve a true "shape", be nice to try, but I'm not going to obsess over it. In any event, I appreciate all your comments in this matter. By the by, rxrenesis, nice pics, my friend!

[pumplover]

Just say want to say thanks Jeff. I do like reading about your little jaunts

[JeffB]

Just say want to say thanks Jeff. I do like reading about your little jaunts

Glad to be of service! Thanks for the kind words!

[rxrenesis]

Thank Jeff. That's my new toy. rx

[JeffB]

8/25/2010:

After a month and a half layoff (thanks to busy stuff and just plain laziness), I finally went out on a jaunt. Here's what I wore on my outing:

My magenta polo shirt from Old Navy, the 37 inch black A-line skirt from JCPenney, off-black L'Eggs pantyhose (the first time I wore hosiery of any kind in months), the Payless black patent "Lance Flex" pumps, my black faux croc print handbag and, something new, a woman's wrist watch I bought from Sears a few days earlier. Oh, yeah, there was one other thing I wore on this outing, can you figure out what it was? And does anyone think I was crazy for having worn this item that I wanted to experiment with? Admittedly, I was probably a tad overdressed, but I felt like dressing up for my first outing in almost two months.

So I drove out to the western 'burbs, even though it was overcast and looked like it could rain any minute, but it never did. My first stop being to a gas station to top off the tank, no biggie, then I headed to the strip mall in Springfield and Borders Bookstore, my favorite haunt when I head westward. As usual, I parked a goodly distance from the front door so I could enjoy that little walk, complete with the delightful sound of my heels clicking on the pavement and the pleasant swish of the long skirt as I walked. The inside of the store was fairly full, what with shoppers coming and going, but, armed with several Mac based magazines, I retreated to the lounge area where I read for little over an hour. The atmosphere was, as usual, calm, quiet and serene, perfect conditions for reading, while I did get a stare here and there during the time I was in the store, no one approached me and was left alone. Again, no biggie. After buying an Iron Man graphic novel, I headed out, even got a nod and a smile from an older lady I held the door open for.

Stop number two was to Bed Bath & Beyond where I sought a small folding table for me to use in my living room to eat TV dinners on while watching TV. After entering the store, I boldly walked up to the first salesperson I saw, asked her where the tables was and was given directions, I made a note to stroll towards the aisle I sought, if but for no other reason than so I could be seen, after picking out a nice little table ($9.99 before taxes), I got in line at the check-out, paid for my purchase while being treated nicely by the clerk and went about my way. My third and last stop of the day was to Best Buy which I loved wandering through because it's fun. I got a few stares and a double take here and there, but nothing more than that, I acted as calm and casual as I usually do, I was just another shopper, despite how I was dressed, nothing more, nothing less, oh, yeah, as usual when in Best Buy, a couple of those friendly blue shirted salespeople asked if I need help, but I politely declined. I left with a copy of Clash of the Titans on Blu-Ray.

After so long away from my adventures, it felt darn good to have gotten back in the saddle. However, I will admit to having felt more than a little nervous at first, I attributed that bit of anxiety to my long absence from freestyling, but I recovered quickly and felt good the rest of the outing. The nervousness I experienced also reminded me of what it was like to be in the fishbowl, of being exposed for the world to see, and that can be a bit unnerving. Now if I were doing the "stealth thing" as in only hiding heels under long jeans, it wouldn't have been a big deal, but since I regularly wear skirts with my heels, there was no place for me to hide, so the only thing I could do was go out, be seen and let the chips fall where they may. Does what I do take a considerable amount of testicular fortitude? Most definitely. Am I brave, given what I do? I suppose so. However, none of that took away from the fun and enjoyment that came from being on a jaunt, and I hope to return to a regular schedule of outings in the future. Something I look forward to.

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.

[Diablo]

Great story Jeff, and with that, you look great on the pictures! I don't think you're overdressed like that. I mean, it's only lipstick, right? Looks good on you, I must say. I noticed most of the men don't have the lips for it (too small) but you certainly do! I noticed because I like wearing lipstick myself too, although not in public. I'm always surprised to read that almost noone seems to notice. I mean, don't people look at others? I certainly do, but maybe that's because of my fascination for shoes... You've got nothing to worry about for looks, I'd say

[Thighbootguy]

JeffB – I like the overall look, but I do think a nice pair of boots (the taller the better) would improve it. (You would be disappointed if I hadn’t said that.) The watch is a nice touch. I’ve thought about it a couple of times, but since I don’t have a goal of “trying to pass”, I have stayed with a male watch. I’m not suggesting that is your goal. Sometimes my watch the only thing from the male side of the store I have on. As for the lipstick… moderation is a good thing, at least at first. Most of us don’t start with 5” stiletto pumps and I think the same idea applies with makeup. Go easy and work your way into it. I’m sure others can offer good experienced advice. Somehow this icon seen appropriate -- As always - Enjoy.

[Henri]

You're wearing lipstick. GREAT touch. You carried it off nicely. Bravo my firend. Henri

[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.