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Exploring

Posted: Sun Mar 22, 2020 11:55 pm
by hiddenheels
Hello... I'm new here, and am still exploring myself in terms of fashion. Been into high heels as long as I can remember, and have a large collection at home, which I try to wear outside as often as possible - given restrictions with family and work, this is once-every-other-week thing, sometimes out at night, a few times to coffee shops. Always under boot-cut women's jeans, that hide the heels with only about 1" of the heels showing. When in coffee shops, I usually go in, buy stuff and sit down to work, at which point the heels are pretty much visible, but I don't flaunt it. I have stubble on my face, and I don't even try to pass as a female.

About a month ago for reasons I can't remember, had a few hours of personal time, and I tried on a mini-skirt to see how it would look with heels. Never experimented with it before, and didn't know what to expect really. I really liked it, and ended up buying a few skirts at a second-hand store. Not the greatest skirts, but they were a good place for me to start. Both were mini skirts. A few days after that, no one else was home and I had some time to explore different heels with pantyhose and my two new-to-me skirts. I experimented a bit until I was happy with it. But boy was it an overwhelming feeling!

Up to this point, I've ventured outside in heels, with the heels always under jeans. Even then, it's usually difficult to get out of the car, but I usually manage after I stop thinking, and "just do it". But now I'm standing in front of a mirror, with my 4" stiletto heel boots, black pantyhose, and a gray mini-skirt, finished off with a white T-shirt and a short black jacket, and I stopped thinking straight. The look was amazing. I grabbed the car keys, drove about 15 minutes away to a neighborhood I've walked in a few times in the past (in heels & jeans), and without barely any self-talk got out of the car and started walking. In a mini-skirt. With the heels completely visible. And it was so liberating! I can't remember the last time I felt such freedom. Some cars passed by, some of the trip was under heavy lighting with apartments nearby, but I didn't meet anyone.

It all felt like a dream, but it was so awesome! I don't know how I went from "let's hide those heels as best as possible" to "let's wear a mini-skirt with 4inch stileto heel boots". All in a span of a few weeks.

Since then I've been doing a lot of soul searching, about what I want, who I am, what I'm trying to represent and the image I wish to portray. I'm straight, and do not wish to pass or become female, that's not changing. I'm just a guy who wants to borrow some stuff from the female side of the closet.

Since that walk, I've bought a few more second-hand store skirts. I also completely accidentally came across a store with a clearance section where skirts were 2-for-$5, and I ended up buying a few right then. I guessed at my size, but for that price I couldn't pass it up. One skirt looked so amazing (sort of like this, but much lighter brown: https://d2h1pu99sxkfvn.cloudfront.net/b ... GO9/P0.jpg]! I had to go out again in it, and I did. Another walk after night-fall, 15 minutes or so. During this outing, I made mental plans to go back to that clearance and look through the selection more methodically (2-for-$5!!), but decided to push myself and wear that skirt during my trip. A few days later I ended up going back to the store, wearing that skirt, beige pantyhose, brown jacket, brown ~2" chunky heel boots. Stood in the parking lot by my car for a few minutes before having the courage to go in. But I did go in. Looked through the racks, picked like 20 mini-skirts that looked like they would fit, went to the fitting rooms, and tried them on. Ended up buying like 7? A few other customers were in the store, but it was actually very liberating looking at skirts while wearing one! I didn't have to pretend... "This is for my GF, can she bring it back if I guess the wrong size?". And I could try them on without worry or shame! No one said anything.

I haven't been able to recreate this type of experience since then, this virus derailed all my plans. My family doesn't know. My wife would have deep problems with this, she's been struggling with the heels throughout our relationship.

Having said that, I was able to go out one night a few days ago. Recently I bought a red plaid mini-skirt (my all-time favorite look), something like this [https://www.trashandvaudeville.com/medi ... _zoom1.jpg]. Black pantyhose, 4" stiletto heel boots, white T-shirt and black jacket. The look was simply amazing. The skirt very comfortable. It took a bit of effort to get out of the car, but I ended up walking around several blocks, including by a large road, for 30 minutes. It was dark, and I was stressed out of my mind for the first 5 minutes or so. Then I started relaxing and enjoying it. It was an amazing experience...

I don't know where this is heading, but so far it's fun. I've read quite a bit of this forum, and hope to contribute my share...

Re: Exploring

Posted: Mon Mar 23, 2020 2:32 am
by Jim
Welcome to Skirt Cafe. Thank you for the great introduction. Sounds like a good start, with one exception.

I would recommend being open with your wife. When she finds out you've been hiding this it could really hurt the relationship.

Re: Exploring

Posted: Mon Mar 23, 2020 3:07 am
by Faldaguy
Welcome aboard -- it is sometimes a rocky ship, but a pretty solid hull. You will find a lot of heart-felt exploration about these topics, as well as practical advise -- so explore some of the old posts and you may find some inspiration and words that speak to you and your condition. [Kenny Rogers, said it well:

Yeah, yeah, oh-yeah, what condition my condition was in
I pushed my soul in a deep dark hole and then I followed it in
I watched myself crawling out as I was a-crawling in
I got up so tight I couldn't unwind
I saw so much I broke my mind
I just dropped in to see what condition my condition was in
Yeah, yeah, oh-yeah, what condition my condition was in

I'd echo Jim in that secrets in marriage that may upset your spouse are not good for you. Try to find a route you can be more open with her. You can reassure her all your male bits and desires are still working in her favor, but you are attracted to the freedom, comfort, & option of expression that heels, skirts and the flair that cannot be found within the limits of traditional men's clothing. You will need to find your own words, for your own situation, but if possible, trust in her for the import of your relationship -- even if you end up in disagreement, get it out in the open. Meantime, you will find some good reading herein.

Re: Exploring

Posted: Mon Mar 23, 2020 8:23 am
by Sinned
I'd echo the advice about including YOH in the honesty about your skirting but be prepared to make some concessions in the short term. It may be a shock to her and be prepared for the fact that she may never be comfortable with your skirt wearing.

Re: Exploring

Posted: Mon Mar 23, 2020 1:48 pm
by Epiceneguy
Hi hidenheals,

Welcome, I'm a new guy here myself, just want to say you're well ahead of me, I still only wear around the house and in my garden but thanks to all the chat and support on here I am looking at venturing out at some point.

Re: Exploring

Posted: Mon Mar 23, 2020 3:48 pm
by Happy-N-Skirts
I suggest going on a hiking trail in a skirt. No one knows you and no one cares. You can space yourself as far as you want to or you can be friendly. I like to ask people where they are from. We have visitors from all over the country and all over the world. I carry a camera and very often I meet people who would like me to take their picture. Since I carry a camera then I must know how to take pictures. I love the stimulation of going for a walk while wearing a skirt. My wife often goes with me, also in a mini skirt. She thinks it's funny to reach her hand under my skirt, or if I bend over or am up on a ladder she thinks it's funny to reverse roles and peek up my skirt.

Re: Exploring

Posted: Mon Mar 23, 2020 11:13 pm
by pelmut
Happy-N-Skirts wrote:
Mon Mar 23, 2020 3:48 pm
...She thinks it's funny to reach her hand under my skirt,
I had no idea just how upsetting that could be until a very close woman friend did to me once as a joke.