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!?

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!

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

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

[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.

[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!

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!

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

Well, as u can see, that never stops me, Kate! Maybe you're limiting yourself!?
Let me add that your avatar is on MY LIST! If Sherry can't be Neytiri just once, I'll be made to suffer!
73510-205-001f.jpg

[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


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.