Night strolls in high heels

Now, I'm not one to go out in public in heels in guy-mode to be seen.
But I do enjoy walking the trash down to the apartment dumpster, it's a 20 minute walk round-trip.

Just about 45 minutes ago as I was chilling in some Mary Jane heels, pajama pants, and a hoodie when I just decided to.

So leaving the heels on I changed into an ankle-length black skirt, keeping the blue hoodie on of course.
I had already been wearing the heels for hours at this point.

These were the heels:

https://www.crossdressers.com/forums...els&highlight=

I headed out at about 0520.
A few cars passed, no biggie.
As comfy as the heels are, they do become a little pain on the return, but I obviously don't mind.

Share your such adventures.

:)

That's quite a walk in those beige heels and to be already wearing them for a couple of hours, I'm impressed they must really be comfortable. Now I'm not sure about a hoodie and an ankle length skirt..... But I must say you did pull it off. Good job.

Mine was in a provocative short LBD when I was eighteen.
I turned a lot of heads and it was dark.
It was also just after six o'clock at night.
I would not recommend going out much later, dressed in this way.
I also had company following me to help in an emergency.
They got the best view as they could see all the reactions with me passing others in the street.
I only did this once. Yes it was on a dare......

I have often fantasized about how it would feel to dance the evening away then leave the club and feel the cool night air on my nylon covered legs. Then contently smile and listening to the sound of my heels on the sidewalk as I make my way back to my car.

I know it is just a fantasy but it is one I truly hope comes true someday.

(((((hugs))))), Olivia

Couple of Halloween visits to Disneyland dressed and wearing 4" to 5" heels. Must have walked 3 to 5 miles over those nites. Every step on the way back to the car was absolute torture!

But, would I take off those heels and destroy the illusion of a Disney Princess in the eyes of the youngsters there? Not a chance!:battingeyelashes:

Congratulations on the walk. Heels that high make walking any kind of distance a challenge for even expert heel people.
I have a couple of pairs over 4 inches but I dont like walking in them. But, oddly, I can go all day in a couple of pairs of pumps that are 3 3/4". Go figure.

A couple Sundays ago,, i took the dog for a walk, really late, like 11:30 in a pair of Jaclyn Smith mary janes with 3 inch heels. Loved the sound echoing through out the neghborhood. Michelle

Alice, those heels are too much for me. I think I would fall over or trip or somehow injure myself. You must live in a rather large apartment complex if it takes that long to dump your trash. When I take an evening stroll I venture out to the Proctor shopping area. It is a quiet residential area with several street of small stores. I usually park in a grocery store parking lot and go for a stroll. When I first started these strolls I wore a three inch heel. Well, walking in heels on concrete sidewalks is a killer on the shoes and the feet. Man made materials are not as comfortable as natural leather. Additionally, the clicking of the heels on concrete is deafening. If one is trying to not draw attention walking in heels is not the way to do it. I found a comfortable pair of black wedges with a 1 1/2 inch rise in the heel. The soles and heels have a noise deadening material. They fit well and enable me to stroll along for as long as I want. For me it is always a knee length dress with heels and hosiery and all the proper undergarments. Wig, but no makeup. Nobody is going to see me in the dark. I have found strolling in a gently falling rain is great. Using an umbrella comes in handy to obscure my obvious male face.

Decades ago I took an evening stroll in a nice solid bright red dress, red heels and nude hosiery, and, a blond wig. A pickup truck passed me going in the same direction. The driver gave me a honk and a holler. I just cringed and thought, what the heck would I do if he stopped and tried to pickup me up. That street was more of a thoroughfare in my neighborhood. I decided to switch to a older residential section of town where the streets are narrow.

For someone wanting to get out of a car, but, not take a stroll I always recommend fabricating small errands; dropping off books to the night return slot at the library, mailing a letter, getting a free newspaper from a box, buying a soda from a vending machine. I found over time the distance from the car to the destination increases.

I think the idea of the small errands is terrific! Just park as near or far as one is comfortable, and gain confidence over time.

Sami

One night while dressing I wanted to walk around the block, so I did in reasonable shoes. Then I decided to pull out the 5 1/2 “ rhinestone sparkle heels. Wiped out going down a hill! Thankfully the shoes came with a bag of rhinestones to glue back on and I wasn’t injured in front of my neighbors house!

Well you did good going that long walking in those heels. The higher the heel, the better the look, the less they are actually made to be walked in. Now are you going to make it a regular thing, this "trash" walk? Maybe you will build up and be able to do it easier with practice/training. But good for you! Sherrii

20 minutes to take out the trash? I would hate to be in that situation.

As for wearing heels to take out the trash, most women would not do that, especially if it was a 20 minute walk. It's not a crime however so if you enjoy it and it doesn't cause you problems, go for it.

Cool.

I just cannot be comfortable with heels of over 2 inches or so. Even with heels of around 2 inches, if I wear them, say, even for a few hours, to a bar etc, I often end up taking them off right after leaving the place, and then going home barefoot :)

I like to go out the front of my building and walk to the parking lot on the south side of it. Usually around midnight, when the only traffic is night shift and bar types going home. The sidewalk is right next to the street. I love the sound of my heels on concrete, as well as the feeling of headlights on me and the occasional honk.

Great pictures, Mirima!

Sami

Nice story Alice, sounds like you had a good time, geez your apartment building must be massive or you walk really slowly

Mirima, watch out you don't get mistaken for a hooker by the police or some drink guys looking to cause trouble. You do look good, just be careful. Sherrii.

You can dress like a hooker, you can't have sex for money! Cops are not going to hassle someone dressed a bit racy unless you are loitering and flagging down passing cars. I do agree about getting hassled by some drunk guys thinking they found a party girl that turns out to be a dude in a dress!

I think the longest I've spent in heels is about 40 minutes, looking at doing an errands trip next week wearing heels though.

After a night on the town wearing high heels it's a common sight to see girls with heels in hand,just giving their poor feet a rest,just another one of those little things that we can experience just like Gg's

On a works do,after a few drinks I slipped a female colleagues heels on and had a dance.other folk there thought it was just a drunk guy doing something mad.But a few of my colleagues (who know about Sophie) joined in and danced with me and we shared knowing smiles :)

Nice. I also love night walks fully dressed. Sometimes I walk for 3 or 4 hours in 4 inch heels.

I have walked all day in heels. Got to say that it may hurts after a while. But No issues.

Sounds DANGREROUS to me. But then again I am "too chicken" to go out in the day time, much less the night. Especially by myself. To ME, anyways, just going out dressed at all seems to be Bravery or foolishness, putting both my reputation and life at risk. (but this is my opinion as a "closeted" CD)---------I would think it was "Risk taking behavior", and I can see how one could get a HIGH from it.----With less serious consequences than doing something like SKYDIVING or Mountain Climbing---a couple OTHER things I would not even THINK of doing. ;)

Yes, it's risky even if you take all safety precautions. It could ruin your life or at least have serious consequences if you get caught by people you know or get physically harmed or robbed. But it's fun doing it and it's still less likely you get caught ta night than during the day.

I've also discovered the excitement of taking night walks Marina and I can tell you it's exciting as hell. I love the sound of my heels echoing up and down a quiet street. And I haven't even felt the need to disguise the fact that I'm a man: https://www.crossdressers.com/forums...-What-a-thrill.

Incidentally, my other hobby is flying my homebuilt aeroplane (the main reason I replied to your thread). I love that as well partly for the element of danger, but also that it's something that most people never experience. The appeal of both is somehow similar for me.

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Originally Posted by Alice_2014_B

Share your such adventures.

:)
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I strolled with a fellow CD Sister around the neighborhood where my local CD support group held their meetings at, when fully dressed a few times. It's an older neighborhood just off Monroe Ave in Rochester, NY and we stuck to walking on the side streets. It was dark out and at a glance, we simply looked like two ladies taking an evening stroll. I was a bit nervous, but at the same time it felt good and so did the breeze blowing up my dress and feeling my slip rub against my stockinged legs and the click, click click of our heels on the sidewalk! Maybe I'll do this again!

I suppose it depends a lot where you do it. Wien (Vienna), at least in Josefstadt where I live, is the most unthreatening of cities. I've seen cross dressers in daytime and nobody really seems to care. I actually suspect that, were I to find a suitable group of youngsters, they might even enjoy having me along as a kind of token eccentric. I've certainly been adopted more than once by youngsters when I've gone into a bar after work (suited up). That's the kind of person I am and Vienna is that kind of place.

Unfortunately, I might not discover whether my hunch is correct because I'll be moving to Stockholm soon.

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Originally Posted by MiniRock

I'd say go for it Sherri. I suppose it does depend a lot on where you do it though. Wien (Vienna), at least in Josefstadt where I live, is the most unthreatening of cities.

Unfortunately, I might not discover whether my hunch is correct because I'll be moving to Stockholm soon.

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Thanks for the encouragement, Tina! Things are actually getting better nowadays for folks like us! I'd have to drive into the city though, to where the accepting neighborhoods are. I currently live in a suburb of Rochester and there's no sidewalks out here and it would look strange to see a well dressed women in heels walking along the side of the road. :)

I'm planning on moving soon as well, out to Colorado Springs. Be careful in Stockholm, I've read that the crime rate is increasing there.

Thanks for the warning Sherri. I've heard that Swedish cities in general have changed beyond recognition in recent years. I'll post something when I see what it's like.

I have walked outside at night to my mailbox. It was late at night and in winter when all neighbors windows would be closed. I just love the sound of heels on a hard surface.

The last time that I tried walking around the neighborhood late at night, I encountered a big dog blocking the sidewalk a couple blocks along. The dog knew that no one walks around the neighborhood at that hour. It did not matter how I was dressed. I did not belong in its territory and that was enough for the dog. I calmly turned around and slowly left, slow enough that the dog did not give chase.

Walking late at night in high heels is going to cause suspicion, especially if you're also wearing a miniskirt and other "hooker" apparel. Yes, it's not illegal to dress like a hooker, but you're quite likely to be stopped and checked out by the police. Also, normal women do not walk alone late at night, especially dressed as a hooker. There's a pretty good risk of one or more guys mistaking you for a hooker and that can lead to all kinds of problems.

It's far safer to walk in broad daylight in a crowd of people. Not dressed as a hooker of course, but dressed as a woman. You wont be stopped or attacked on a busy city street in the daytime or in a crowded shopping mall.

Nobody will mistake me for a hooker! I dress sexy, but pretty much in line with the girls in the club down the street. And when I come out the door, it's only about 30 feet to the parking lot entrance, and I walk with a purpose. I definitely don't loiter about, I've actually had cops go by me 3 times without any problem. I also do more walking as of late during the morning time as there is more traffic, and when one would figure there would be less chance of complications, like drunks pulling over. Yet while I dress more conservatively, the two times someone has slowed down and asked if I needed a ride were both in the a.m. Here is an example of my night and day walk apparel. I think you can guess which is which!