Dressing completely ridiculously without a care! Do u ever do that?

[docrobbysherry]

If you're a closet dresser like me, maybe that's almost the ONLY WAY u dress!?:devil:

I don't dress my age! I don't care about styles! I don't care if my outfit's immodest, overly sexy, totally inappropriate, silly, or even ridiculous! I don't care about passing! I don't dress to please ANYONE! Except myself!:battingeyelashes:

While I find dressing to go out VERY SERIOUS and STRESSFUL, dressing at home is the opposite! IT'S SIMPLY TOO MUCH FUN!:D

Do u EVER dress like that? Without a thot or care in the world? :straightface:

[Cheryl T]

I always dress without a care...just not in clothes that are in the category you indicate.
I don't find dressing to go out stressful or serious at all. For me it's pure enjoyment. Being able to be the real me for a while without worry is stress free.

[NicoleScott]

Doc, I dressed up in private for a long time, and there are no rules when dressing in private. But when the desire to go out overwhelmed my fear, I did try to "tone it down" a little, but found that unsatisfying. So I prefer to stay home and dress and make up in my preferred style, or go some place where I would be seen as a CD but accepted anyway, like a tg-friendly club. I did that, too, but still like the "home alone/no rules" dressups.

[Kaz]

Love it Sherry! When on my own my imagination can run riot! And frequently does! Whoops must get some work done! :)

[RileyEvans]

I do, I only dress in private and I dress in whatever I want no matter the style or lack of coverage.

[Kate Simmons]

I try RS but when it comes to trying to be the Playboy Centerfold for the month, I fall a bit short.:heehee::)

[LilSissyStevie]

Yes, I'm a complete disgrace to the respectable crossdressing community.

[Jocelyn Quivers]

Since I'm still in the at home/in door phase I'm wearing all of the age inappropriate, ill fitting, too small and tight, floozy, outfits I can so I can hopefully get this phase out of my system. The sooner the better.

[Cynthia Anne]

I dress to please only myself! If I feel like wearing a dress to town then that's
what I wear! May be the next day going to the same places I will wear jeans and a top! I please my self!

[docrobbysherry]

I always dress without a care...just not in clothes that are in the category you indicate.
I don't find dressing to go out stressful or serious at all. For me it's pure enjoyment. Being able to be the real me for a while without worry is stress free.
U r my heroine, Cheryl! I don't think I'll EVER feel relaxed when preparing to go out. Altho, I must admit I don't mind the stress if I get to hang with other cd.com girls when out! They're WORTH IT!:hugs:

I dress to please only myself! If I feel like wearing a dress to town then that's
what I wear! May be the next day going to the same places I will wear jeans and a top! I please my self!
Next time, try going there topless, Cynthia! At home, I often find THAT LOOK most pleasing!:D


I try RS but when it comes to trying to be the Playboy Centerfold for the month, I fall a bit short.:heehee::)
Well, as u can see, that never stops me, Kate! Maybe you're limiting yourself!?:heehee:
Let me add that your avatar is on MY LIST! If Sherry can't be Neytiri just once, I'll be made to suffer!:sad:
183958

[naye]

I do it 99% of the times, just put on any clothes that I like and just dont care how they looks on me, btw Im closeted thougj

[Princess Chantal]

Nope, I always dress conservatively to blend in..... Even if it means that I have to wear clothing that I don't have an appreciation for. I can't imagine dressing any other way
:heehee:

Okay I am kidding. I wear what I want when I feel like no matter how ridiculous it may look (private or not).... As long as it puts a smile on my face and satisfies my precious crossdressing time.

Be it looking like a hoochie mama street walker look, or a 70's Mary Tyler Moore lookalike, or big heavy 80's make up..... if I am in the mood to do it, I would do it

[joanna4]

Yes, I dress sexy and go out. Its definitely thrilling and I love to wear the clothes that I want and be able to go out. I like to feel what the women and girls feel when they where the exact same/similar clothes/outfits out to go shopping/clubbing.

[Eryn]

Sherry, whenever I'm shopping I always take a few things into the dressing room to help me live the teenage years my femme side missed. Yes, some of those items look a bit silly on a 50ish lady, but they are therapeutic to my soul.

(And some of them I look pretty good in! Too bad I have a 50ish head attached to a junior body!)

[Beverley Sims]

When I have time by myself I do experiment with dressing in some ridiculous attire.
Sort of fun sometimes and other times I think...
Why did I do that?
It hurts no one and you satisfy a curiosity.
Just part of the fun.:)

[Diane Smith]

More power to ya Doc, but for myself, once I started going out, I almost completely lost the desire to dress alone at home. Now, 99% of my shopping and dressing time is focused on actually going somewhere, either fancy or mundane. I do wear casual fem clothes at home (and always heels, have to stay in practice, you know), but don't really put any thought or effort into it.

- Diane

[jillleanne]

Good for you! I recall doing the same to some degree when I was in the proverbial closet, I suppose because of the limited time it affords, and for sexual gratification back then. Unlike you though, I have never felt stressed or anything negative getting ready to go out. Maybe because I do not need to rush, not sure. Often my s/o will pick out what I will wear out that day so it's no big deal I suppose. Yes, almost always with heels in or out.

[Mistybtm]

I dress any way I want at home not worried about passing I know i won't anyways so i do not worry about it.

[Foxglove]

Sherry, the very fact that I've abandoned drab is exciting enough for me. I'm not very adventurous and don't really have any plans to become so. I work from home so I can dress a lot, and when I do, I like to be comfortable. If it's a dress or skirt, I'm fine with that, whatever sort of dress or skirt it might be. I think a lot of cis-people would find me pretty boring in my drab life, and a lot of transpeople would find me boring in my trans life. I don't care. I'm happy these days, and isn't that what it's all about?

Best wishes, Annabelle

[cdterri]

I dress however I feel, from a cowgirl, to prom night, wedding night, steetwalker, maid, cheerleader etc. only two going to see it are my Wife and I. Just turned 65 by the way.

[Sarah Doepner]

It has been known to happen. In fact, it kind of drifted on my first time out of the hotel room, but I didn't realize it until quite a while later. My Bad. Most of the time now I just try to find workable combinations that I can pull out of the closet and jump into if and when the chance to get out arises. Of course sometimes that results in what may be a, ahem, a "Challenging" outfit.

[Claire_tv_uk]

oh my god, i do this all the time, crossdressing is pure fantasy to me, and i ever go out dressed, so i don't really have any rules to play by.

i've worn some silly combinations in my crossdressing life, i love the trashy look.

[Wonderwho]

I love the trash look, stockings, short skirt large breasts and ......... sorry I forgot this was about what I wear. The same thing but the body of a 60 year old has a tendacy to not carry the
hot young modern woman style. But what thw H**l this is my closet world and I will do what I want to in it. If you stay away from a mirror everything looks great!!!
My best to all, Wonderwho
Sherry, Welcome back, you sexy dog you.

[Lorileah]

Sherry we love you but I ain't buying the without a care part. You always look well put together.

I dress totally with care. I want to be noticed when I am out. I don't do the age thing either (who cares? I don't want to look like Hillary Clinton or the church lady).

Thanks for sharing the photos

[BLUE ORCHID]

Hi Sherry, aAs I dress in private I have many different styles of dressing what ever suites my mood.