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I Like to Wear Skirts

Personal Stories, Advice, and Support 3,136 People

    pmtnga pmtnga 36-40, M 5 Responses Dec 26, 2015

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    LeahUK LeahUK 13-15, F 22 Responses Dec 27, 2015

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    I got some new items in today.

    A couple new skirts and new leather boots. This is my faux leather flare skirt I have with my new boots. They fit quite nice. I wonder if I should shave my legs lol. Might look nicer I suppose.
    djshire djshire 31-35, M 4 Responses Jan 29

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    OMG! Today was incredible.

    I completely dressed in a skirt and heeled boots while traveling through one of the busiest airports in the world: Atlanta Georgia. Never thought I'd be capable of doing it, but I did! Never had any comments, problems or snide looks at me. Even had a flight attendant tell me...
    shadowplt shadowplt 51-55, T 9 Responses Sep 21, 2015

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    This evening my two sisters

    and their husbands will see me wearing a skirt. They do not know I wear skirts. Wish me luck.
    deleted deleted 26-30 17 Responses Jun 3, 2015

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    I'm wearing my new plaid mini skirt

    now that I just picked up. I love it!!
    boypanty13 boypanty13 31-35, M 5 Responses Nov 2, 2015

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    Today begins my journey from me to Sherry.

    I'm traveling to reveal myself to my family and am scared sh..less. Tomorrow when my brother arrives, I'm planning to sit down with my parents and brother and reveal to them that I'm a crossdresser and TG. My therapist suggested that I start this process by revealing and...
    shadowplt shadowplt 51-55, T 12 Responses 1 day ago

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    Yesterday I went with my wife to see a marriage

    counselor and hopefully help us find a way to resolve our issues. Apparently, I'm the issue. I felt like she vented about my major problem and the Dr focused on it too. Then the dressing was brought up and that raised more questions. I'm going back to see him individually next...
    shadowplt shadowplt 51-55, T 10 Responses Dec 31, 2015

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    I went to a therapist today.

    Yea for me...I think. He was very much understanding and helped me a lot. I'll go back to him. What's weird is his gender neutrality and his understanding.
    shadowplt shadowplt 51-55, T 5 Responses Dec 29, 2015

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    I want all of my EP friends

    and those who read this to know I'm doing well. I miss being with my wife and daughter. My dressing isn't the problem. It's my other problem I have to deal with. Please keep me in your prayers. I thank you for your support and thoughts. I'm grateful to have a group of people who...
    shadowplt shadowplt 51-55, T 7 Responses Dec 7, 2015

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    Skirts

    I have a large selection of skirts in all styles and lengths made of a variety of materials.I have a number of flared mini skirts that look great with seamed stockings, they always turn a few heads.I have to the knee demure skirts for work.Generally I find skirts a very versatile...
    sally1981 sally1981 31-35, F 26 Responses Dec 27, 2011

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    I have the best family ever I'm a 45 year old

    man married to my wife and I have 3 kids two girls aged 22 18 and one boy aged 15 and they all know that I wear skirts and tights nothing else I don't want to be a woman I am just a man who likes to wear them , they really support me in doing this and I love them for it , I...
    deleted deleted 26-30 10 Responses Jul 13, 2015

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    Yesterday I had a frank discussion with my wife

    about our relationship, things happening in our marriage and where we're going from here. Today we're having a realtor come to our house to sign contracts and begin putting it on the market. My wife told me that I could wear whatever I wanted to the meeting. I was aghast. I'm...
    shadowplt shadowplt 51-55, T 8 Responses Jan 17

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    It is strange but I have personally never had a

    desire to be feminine or a girl as I am a bloke. Though I do respect other men whose views differ. However I do wear skirts at home, as I think short skirts could be designed for men. I have no particular chip on my shoulder about it though and feel equally comfortable about...
    littlegreyshorts littlegreyshorts 51-55, M 4 Responses Jan 31

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    janetjanet janetjanet 51-55, T 3 Responses Jan 19

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    I just got a text from my friend reminding me

    that I committed to a golf tournament tomorrow. He's a burly, barrel-chested, manly - man with a heart of pure gold and knows nothing about my feminine wiles, as far as I know. So my wife and I meet he and his wife for a night out, and he shows up wearing a kilt ! When I...
    JessicaDale JessicaDale 51-55, T 6 Responses May 8, 2015

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    It's not an issue for me,

    though. I'm a woman. But I still love wearing skirts. I love wearing those dyed gauze skirts with a halter top or a cropped baby tee, & bare feet!
    MeghanL MeghanL 26-30, F 7 Responses Jun 3, 2015

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    I love wearing my skirts

    and shoes. of course there is a thong . found some cork clogs at family dollar for 8 bucks. they are cute.
    jpeck1 jpeck1 41-45 Jan 30

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    There I was. Sitting at my apartment watching TV

    when my door bell range. Now I'm wearing my skirt and heels when I answered the door. It was the post lady asking a question. We talked for a bit and as she was leaving she said,"Have a nice day sir.....er Mam.". Kinda made my day.
    shadowplt shadowplt 51-55, T 4 Responses Feb 3

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    Called Dillard's this afternoon.

    I asked if they do make-overs. The answer was yes. I asked if they do it for men; again yes. I then asked if I could come in and learn how to do it. Yes. How much does it cost? Free. I'm going to do it for the experience.
    shadowplt shadowplt 51-55, T 6 Responses Nov 18, 2015

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    I'm glad I found this page.

    I'm a straight guy who has always had a thing for skirts ever since I was a kid. I do own a few that I bought online. My favorite one is a black faux leather flared knee length skirt. I wear it around the house often but I don't have the courage to wear it in public. Although my...
    djshire djshire 31-35, M 4 Responses Jan 25

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    Ok, here goes.....It's official,

    I'm getting divorced. My soon to be ex-wife and I had dinner together last night and discussed our situation. It was a very frank and quite relieving talk. Nether of us is upset, hurtful towards one another, or wanting to have hard feelings; we're just not compatible in our...
    shadowplt shadowplt 51-55, T 12 Responses Jan 20

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    Well the cats out of the bag,

    I crossdress. My wife knows that, doesn't like it. We're going through a separation/potential divorce. I'm saddened that's how 16 years of marriage ends up. I've screwed up by not being able to to be honest with her. To you guys who are scared of the truth to your wives, be...
    shadowplt shadowplt 51-55, T 9 Responses Jan 15

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    I know a lot of girls prefer to wear pants,

    but for me, skirts are almost always nicer to wear. If you don't wear a fitted skirt, I find my legs can move more easily when I'm wearing a skirt, maybe because the fabric's not trying to stay still on my legs? I also really like the... "ventilation" one can get with a skirt...
    deleted deleted 26-30 5 Responses Jan 22, 2015

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    Today I put on my Wolford 20 sheer hose

    and a black denim skirt with flats. My wife wanted to visit her friends house but wanted me to drive her there so I had to take her there and back about 30 minutes each way. I decided not to change into male clothes but stay in my tights and skirt. She didn't say anything about...
    deleted deleted 26-30 21 Responses May 21, 2015

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    Just finished the first leg of the trip.

    All's been going smoothly so far. My confidence is growing as I'm out and about the airport and on the plane.
    shadowplt shadowplt 51-55, T 2 Responses 23 hrs ago

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    Just an update for those of you keeping score.

    It's been a little more than a month since my wife and I separated. I've missed her very much and unfortunately not missed some of the things that made us drift apart. I'm enjoying the freedom to be myself and dress how I wish. Most days I'm wearing women's clothing: panties...
    shadowplt shadowplt 51-55, T 7 Responses Jan 9

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    just tonight I worked up the courage to step

    out in a skirt and wedges and walk around the block it was a little scary and got the heart rate going but nothing bad happened was seen by a few passing cars it was a fun time
    jamie172 jamie172 46-50, T 7 Responses Jul 27, 2015

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    Wearing this skirt, I went to Buffalo Wild Wings

    for dinner. Got several complements from the wait staff.
    shadowplt shadowplt 51-55, T 6 Responses Dec 23, 2015

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    Well today's interaction with my therapist was

    interesting. I'm femme and always will be. More later.
    shadowplt shadowplt 51-55, T 2 Responses 1 day ago

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    Ok then....Today was a most illuminating day.

    I went to work as usual and got done as usual. After work, I had an appointment with a lawyer specializing in divorce. She wasn't all that helpful unless I retain her for a lot of money. I went over to my soon to be ex-wife's place. She offered me a meal which I greatly...
    shadowplt shadowplt 51-55, T 5 Responses Jan 25

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    Well, I've made it to my destination in one

    piece. Decided to not drive out to my parents house this evening. Just tired of traveling. So I got a hotel room near the airport. Will drive out in the morning and have a discussion with the folks and my brother. Really felt comfortable in a skirt and heeled boots today...
    shadowplt shadowplt 51-55, T 3 Responses 16 hrs ago

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    Yesterday I decided I would change into my

    skirt at work. I just happened to have one in my briefcase, well, you do, don't you?! So I walked through the office and out into the car park to my car. I drove home and when I got home and was greeted by my wife she just said, oh, a skirt at work today? I said yes. Later we...
    deleted deleted 26-30 5 Responses Jul 19, 2014

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    This is the skirt I wore today.

    I'll be sad to take it off at the end of the day.
    KatieTreat KatieTreat 51-55, T 28 Responses Jun 30, 2015

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    Wow, just spent a s--- load of money to attend

    a conference in May where I get to spend a week with a bunch of people like me. I'm going to Esprit 2016. I'm scared, hopeful and wondering just what the heck I've gotten myself into. Jess, if you read this, message me and tell me I'm not going to be doing something wrong.
    shadowplt shadowplt 51-55, T 5 Responses Jan 31

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    I've discovered something about myself today

    and how I feel about my soon to be ex-wife's feelings about my wearing a skirt. I don't care how she feels about it. If I embarrass her, then I guess she still cares somewhat. But really, who's to care her or me? I'm the one who has to live with myself and the consequences of...
    shadowplt shadowplt 51-55, T 7 Responses Jan 24

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    Yesterday my life has changed.

    My wife and I had a "discussion" about my wearing skirts. She was very upset about my wearing them and doesn't like it at all. I tried to reason with her, but it doesn't sway her feelings. When I said that she can wear whatever she wants: jeans, tennis shoes, tee shirts, and guy...
    shadowplt shadowplt 51-55, T 37 Responses Sep 13, 2015

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    Well, I'm convinced the world (at least around

    where I live) isn't as asinine as the TV and news would have you believe. I went to the city today dressed in a skirt and heeled boots. As I've said before, no make up, breast forms or pretending to be what I'm not. I was accepted in every place I went; the mall, conscience...
    shadowplt shadowplt 51-55, T 1 Response Jun 21, 2015

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    I have discovered this last weekend

    that I love skirts even more than I thought. I have always worn hose with them in the past. most often thigh highs. However, my girlfriend painted my toes and I was wearing a skirt while letting them dry. Also I ran around the house doing a bunch of things and realized that with...
    hosedsailorboy hosedsailorboy 41-45, M 7 Responses Jan 25

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    I'm so into pantyhose lately,

    I just can't stop! Today I am in a blk cocktail dress and hose just cleaning and doing my thing at home. I'm so tempted to go out dressed I'm just not confident enough for the daylight ( I have done nights ). I just wish for that nylon shimmer in the sunlight and for a lady to...
    VeronicaNpantyhose VeronicaNpantyhose 36-40 9 Responses Nov 12, 2015

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    Ok then. This doesn't have much to do with

    skirts, but I bit the bullet this evening and had my ears pierced. Should be an eye opener tomorrow at work and when my daughter and wife see it. Can't wait for the criticism and geers.
    shadowplt shadowplt 51-55, T 4 Responses Jan 27

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    shadowplt shadowplt 51-55, T 1 day ago

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    Not quite sure where to put this post,

    but I think this will do just fine. Saturday I painted my toe nails a nice light purple sparkle color. Just having some fun and didn't think about it. Today I had a Dr's appointment for a full body scan of my skin. (I've had melanoma and some other skin cancers. ) Well I'd...
    shadowplt shadowplt 51-55, T 2 Responses Apr 13, 2015

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    Well I tried on my first skirt today in 10 years

    and I wanted to know what y'all think about this outfit that I might get
    deleted deleted 26-30 24 Responses Jul 30, 2014

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    I like to be naughty some days

    and go without panties. It is a rush when you know something that no one else knows. Especially when it a naughty one. I like to sometimes be a lot more naughty and in public I will slowly uncross my legs to change legs crossed. Nothing like a small tease.
    kittyluv78 kittyluv78