I Like to Wear Skirts

Personal Stories, Advice, and Support 3,002 People

    Jess: bought this cardigan to go with the dress

    and heels. Perhaps wearing this outfit to Vancouver on the ship.
    shadowplt shadowplt
    51-55, T
    2 Responses Feb 28

    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
    7 Responses Sep 21, 2015

    As I sit here tonight,

    I begin to wonder if my lifestyle is one I want to continue? I love who I've become, I like my lifestyle, but I've lost the most important and positive things not in my life.
    shadowplt shadowplt
    51-55, T
    3 Responses Mar 21

    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
    deleted deleted
    26-30
    5 Responses Jul 27, 2015

    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
    6 Responses Nov 12, 2015

    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

    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
    4 Responses Nov 18, 2015

    Yesterday was a good day

    for me and a bad one too. Good day: I invited my daughters over for a taco dinner night. Just a time to be with them and converse. Had a great meal and just chitchat. Before dinner, I had texted both of them and asked if they minded if I wore a skirt and my boots. Both said...
    shadowplt shadowplt
    51-55, T
    4 Responses Feb 3

    I am so relieved, excited

    and full of wonderful feelings. Today while we (my brother and parents) sat making small talk, I worked up the courage to come out and tell them I'm a crossdresser. That I've harbored these feelings for years and have decided to act upon those feelings, openly. That it's costing...
    shadowplt shadowplt
    51-55, T
    8 Responses Feb 13

    Just sitting around the apartment waiting to

    start dinner. It's been a beautiful day of doing nothing but breaking in my new heels and dreaming of being at Esprit with my EP friend.
    shadowplt shadowplt
    51-55, T
    5 Responses Mar 13

    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 Feb 11

    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
    1 Response Feb 12

    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
    36-40, F
    14 Responses Oct 1, 2014

    Please, if you like my posts,

    responding would be a great thing. Please just don't heart.
    shadowplt shadowplt
    51-55, T
    4 Responses Feb 27

    I love to wear a skirt with my stocking

    and high hills and have someone slide there hands between my legs
    janetjanet janetjanet
    51-55, T
    1 Response Apr 19

    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
    8 Responses Jul 13, 2015

    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
    4 Responses Jan 31

    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

    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
    7 Responses Feb 12

    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
    19 Responses Jun 30, 2015

    Got these heels today too.

    Jess: believe it or not, they're quite comfortable since I've been wearing heeled boots and have gotten used to walking on a toothpick.
    shadowplt shadowplt
    51-55, T
    2 Responses Feb 28

    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
    5 Responses May 8, 2015

    hi i m bottom ,guy .

    though i dont do it regularly , but one day , out of my curiosity ,i tried it . It was my sister 's miniskirt . And it was looking pretty hot in me , i can felt my thighs grinding with each other . it was good . i may try it gain
    wanttobeexplored wanttobeexplored
    22-25, M
    4 Responses Feb 13

    What saddens me the most about my pending

    divorce isn't that I'll never forget that I love her, it's the missing of interacting with my daughter. I think, but don't know for sure, that my soon to be ex wife has influenced her against me. Certain things tell me that. I'm good with who I am and whom I'm becoming, I just...
    shadowplt shadowplt
    51-55, T
    3 Responses Mar 20

    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

    I'm on the last leg of my flying journey.

    Going home. I've been dressed for the entire trip except when I first got to my parents place. Once I found out that they're supporting of my dressing, I changed into my skirt and heels. We went out and about their city, shopping, dining and sight seeing. Never once this weekend...
    shadowplt shadowplt
    51-55, T
    3 Responses Feb 15

    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
    19 Responses Jul 30, 2014

    My school skirt is too small

    for me now - getting told off by teachers because it's "too tight". Apparently I'm showing things off that I don't want to be showing off.
    LeahUK LeahUK
    13-15, F
    9 Responses Jan 16

    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
    6 Responses Jun 3, 2015

    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
    29 Responses Sep 13, 2015

    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

    Tried on my daughters skirt.

    Kept it on for about an hour while I did some laundry and made my bed.
    mat2Robin43 mat2Robin43
    51-55, M
    9 Responses Apr 18
    shadowplt shadowplt
    51-55, T
    Feb 12

    Is this an acceptable length skirt

    for a school? I need opinions x
    LeahUK LeahUK
    13-15, F
    18 Responses Feb 6

    I'm excited. Yesterday I had the most beautiful

    and amazing day. I finally went out dressed in a skirt in my hometown. I've worn a skirt in airports and while flying to other places before, but never just around doing day to day stuff. I Ate dinner at Golden Corral, no one commented, watched a movie, not one person said...
    shadowplt shadowplt
    51-55, T
    6 Responses Oct 11, 2015

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

    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
    4 Responses Jan 22, 2015

    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
    16 Responses Jun 3, 2015

    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
    jpeck1 jpeck1
    41-45
    1 Response Feb 15

    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
    4 Responses Feb 12

    This is one of my formal outfits

    for Esprit in May. Just got it tonight. Jess. This is for you gurl.
    shadowplt shadowplt
    51-55, T
    6 Responses Feb 27

    Why, as I grow more accustom to wearing a skirt,

    dress and heels, do I begin to want to expose myself to the world. I grew up a guy; have lived as a guy and married had a child (whom I love as Dad) and because of my femme self want to wear "women's" clothes. I know I'm not alone in this, yet I feel as though I'm abnormal and a...
    shadowplt shadowplt
    51-55, T
    2 Responses Feb 28

    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
    16 Responses May 21, 2015

    Tonight I discussed with my wife,

    my dressing. We had a very fruitful conversation. More later. To my friends, thanks for the help.
    shadowplt shadowplt
    51-55, T
    4 Responses Feb 24

    Evening wear as I relax

    and watch movies. Hope you all enjoy.
    shadowplt shadowplt
    51-55, T
    4 Responses Mar 20

    I had to go to the storage unit

    and drop some things off and pick up some other things. I put on my bra under my Hawaiian shirt on the way over. When I went in the office I think I caught the receptionist checking out the bulges in my shirt a couple of times. Then I went out back and changed into a skirt and...
    Sharon03 Sharon03
    61-65
    7 Responses Jan 9, 2015

    Yesterday I drove my daughter to her State USA

    swim meet and sat in the stands watching her excel. She set some personal records in her events. I'm a very proud dad. Having said that, I also wore my heeled boots, mascara and very femme clothes. My daughter complemented my choices and was fun to be with. Between the AM and...
    shadowplt shadowplt
    51-55, T
    6 Responses Feb 27

    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
    3 Responses Feb 3

    Follow up to my last post: My daughter swam in

    the state meet and I'm so proud of her. She did very well. I got to be myself traveling there and back and really enjoyed the swimming. All the kids did well. The more I'm out as myself, the more I feel as though I'm comfortable with it.
    shadowplt shadowplt
    51-55, T
    4 Responses Feb 21

    Ok before I get to bed tonight,

    I just have to say how proud I am of my daughter. She's in the finals for the Oklahoma state swimming meet. Yea
    shadowplt shadowplt
    51-55, T
    5 Responses Feb 19

    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
    4 Responses Dec 7, 2015

    Went to the city today

    for some shopping for Esprit. Found this jeans dress/skirt. Works with tights and/or nothing on the legs. Found a pair of heels also. I'll post that in a bit. Jess: Gurl you are going to have to play catch up 👠👗💅🏻❤️
    shadowplt shadowplt
    51-55, T
    3 Responses Feb 28

    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
    25 Responses Dec 27, 2011

    I love to wear a nice skirt

    and stocking and high hills just to finish the look
    janetjanet janetjanet
    51-55, T
    3 Responses Feb 28
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