First Time Out In Public All Dressed Up

On Saturday nights my wife and I go out to a group gathering of friends. It's a cruise night. We all bring our cars and hang out together. It's a good time. This year we'll be cutting it off for the season in October, on the 30th. It was suggested that this year everyone dress up for Halloween. So we're dressing up and it will be my first time in public in women's clothing. I cannot wait!!! She's going to be in a suit and tie. I have black and chrome 6" heels, black stockings, a black pleather mini skirt, a satin white button down blouse (if it fits), and a black "duster". I bought these heart shaped earrings to wear too. Bright red. I might try and find some red press-on nails to add to everything, we'll see. Sad part is I'm not wearing any of it until the 30th, even though I really want to. I will try on the blouse when it comes in, but everything else will get seen together for the first time on October 30th. This weekend we're going to fit my wife with a black dinner jacket, and then go find some matching slacks for her to go with it. Match it up with a white shirt and black tie. We should look really cute together. I'm a bit scared and excited about it at the same time. I just can't wait!!! Did I say that already? :D When we're done, we might go hit the local casino. Might as well take advantage of a night out in a skirt with no judgement from anyone, right?

Lucky you.

Have fun!! You may realize that going out, in perhaps less striking clothing, is easier than you think!

Sounds like fun event and you have a great wife

It's going to be fun regardless what I wear. My clothes are just an added pleasure. I'm still a bit iffy about the casino part. However, if the cruise goes well I'll be mad at myself if we don't go out there. Yes I do have a great wife. As far as going out the rest of the year goes, I don't think it's a good idea. So since one night a year is better than nothing I may as well go for the ghusto huh?

Enjoy your first time out.

My first time out totally dressed with the intent of mingling with the masses was on Halloween although my wife has home sleeping in bed. Nice that you have a supportive wife. Enjoy the day.

It sounds like a fun evening! However you might want to try the 6" heels for a few hours some evening before you commit to wearing them for the whole evening. Especially if you won't be sitting in the car most of the time. Sherrii

Good advise. Thank you. I don't think it will be a problem though. I wear them for hours at a time already. I will bring a change of shoes though now that you mention it

Sounds like a fun evening. Enjoy! Would love to see a picture. I?ll never forget my first time going out. Scary, but fun.

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Originally Posted by lovesnylons

Sad part is I'm not wearing any of it until the 30th, even though I really want to.

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Why wait? Halloween is my one for sure night out dressed each year. I try on everything I'm going to be wearing many times during the month to minimize the possibility of a "wardrobe malfunction" on the night. During October, my only tolerant wife doesn't bat an eye as I walk around the house in hosiery and heels building strength and endurance for the long night.

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Originally Posted by NancySue

Sounds like a fun evening. Enjoy! Would love to see a picture. I?ll never forget my first time going out. Scary, but fun.

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I'm sure someone will take pictures. If there are any, and I get to see them I will share

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Originally Posted by Taylor186

Why wait? Halloween is my one for sure night out dressed each year. I try on everything I'm going to be wearing many times during the month to minimize the possibility of a "wardrobe malfunction" on the night. During October, my only tolerant wife doesn't bat an eye as I walk around the house in hosiery and heels building strength and endurance for the long night.

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That's a good point. The idea behind waiting is to be sure I don't mess anything up. However, I like your line of thinking better :)

Absolutely go, to the casino, to a restaurant, to whatever and wherever you wish. Only recently have I really pushed the limits and do you know what I found?

NO LIMITS! Just about, but I did go to Panera, first time sitting in a restaurant, many stops before that in malls and single stores (Lidl, JCP, Macy's, Marshalls, etc.), no one seemed to really notice or care! I even went to Target, tried on shoes and looked through the clothing, found a waist cincher in my size without a tag and walked up to the register, the SA smiled nicely and handled my transaction, I'm sure no one is going to ruin your night.

Just go for it, to have your wife (or SO) there with you makes you so lucky. So many of us are so jealous but please promise to just go enjoy it, the feelings and changes will make you wonder why you didn't do it years ago.

6 Inch heels without practice !!!!! Ouch, take some pumps with you so you can have a break if walking far, I can get about quater of a mile in 4 inch heels and thats after years of practice. Enjoy have a good time

I have years of practice in 6" heels. In fact, I'm wearing some right now :) I think I have like six pair? I will bring some tennis shoes with me though for driving. I want to be safe after all

Sound like you both will be "Crossdressing" You will both have fun.
SuziH

I never even thought about it that way. You are right!!!! Gonna be an even better night!!!!!

Halloween should be renamed, "National Crossdressers Get a Hall Pass Day." Good for you to take the initiative to share that with your wife. I'm sure you will have a blast. Don't worry about judgement, it's ever-present, like the air we breathe. No use worrying about that. Just enjoy yourselves.

Halloween was my first time going out dressed. What a blast. I forgot to fill the car with gas before we got dressed so we had to stop on the way. I asked the wife to pump the gas and she informed me since it was my idea to dress as a french maid I had to get out and pump the gas while she went into the stop and go to get some soft drinks. Damn was I nervous standing beside the car. She came back to car laughing saying a couple of guys wanted to know if she and her friend wanted to go to a private party.

Oh I intend to do all my shopping for the day in my skirt for sure

you may want to try on those heels before then

Every year about this time people start talking about going out dressed (as a woman) on Halloween. And yes, you can do that.

The problem is, if you are an experienced crossdresser, you will probably do too good a job and people will suspect that you don't just dress as a woman once a year. What "normal" guy has a nice wig, silicone breast forms, hip and butt padding and can easily walk in heels (and even has heels of his own)? What "normal" guy knows how to apply makeup?

If you don't want people to figure out that you are actually a seasoned crossdresser, you have to do a lousy job of dressing. Cheap wig, ill fitting clothes, balloons for boobs (too big and too high), no hip and butt padding and stumble around in ill fitting heels. And that's just no fun.

Now if you're going to a bar or an event where nobody knows you, go ahead and dress. They will figure it out but since they don't know you, it won't matter. If you will be with family or friends, I would think twice about this. Unless you don't care.

Krisi, your observations are spot on, made that mistake once at the local fancy dress, I stood out like a sore thumb!!! Especially carrying drinks from the bar in heels, nothing spilt !!, fortunately not in that circle of friends or that town. even some of my casual friends didnt recognise me and mistook me for a woman. So dont be to convincing if your supposed to be in fancy dress.

I agree about halloween. I couldnt go out and do a lousy job, its all or nothing. I dont want to be outed either though , so i havent done halloween.
Yet..

I have done the Halloween dress up. My lovely wife and I came up with the story that she did my make up, clothes were rented and she made me practice in the heels for the last couple of weeks. You could also say the clothes and heels came from goodwill, even the wig. Your SO or a female friend did your make up. Be sure to complain about the heels and exclaim that you don't know why women wear them.

wow have fun and post some pictures

I truly ENVY you and your opportunity to express yourself, wish I or WE could join your event.
Although too many guys dressed up might draw the wrong attention, and give the wrong message.

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Originally Posted by RachelB.

I have done the Halloween dress up. My lovely wife and I came up with the story that she did my make up, clothes were rented and she made me practice in the heels for the last couple of weeks. You could also say the clothes and heels came from goodwill, even the wig. Your SO or a female friend did your make up. Be sure to complain about the heels and exclaim that you don't know why women wear them.

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You can't say anything to anyone who doesn't ask. Most people will just make a mental observation of how well you pull off the "woman" thing and decide that this is not your first time dressing as a woman.

I have been on the other side of this as the observer.

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Originally Posted by Krisi

You can't say anything to anyone who doesn't ask. Most people will just make a mental observation of how well you pull off the "woman" thing and decide that this is not your first time dressing as a woman.

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Agreed. This has been my experience.

And if asked, excuses like, "my wife suggested/asked/forced me to" or "I lost a bet" or "someone else did my makeup" or "heels are hard to walk in" (after you've effortlessly worn them for hours) will be dismissed as an insincere dodge.

Shakespeare exposed this subterfuge with a simple statement in Hamlet 500 years ago: "The lady doth protest too much, methinks"

At a party once a woman soon-to-be-friend asked if I had on a bra. When I said yes, she asked, “Did you buy one?”

Any further protests that it was “just a costume” we’re met with her [probably correct] observation that no one buys a bra to wear once…..Blushing the color of an apple didn’t help!

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Originally Posted by Alexis00

At a party once a woman soon-to-be-friend asked if I had on a bra. When I said yes, she asked, ?Did you buy one??

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Friends like that are hard to come by, and need to be cherished. I had a neighbor woman that encouraged & supported my desire to dress, but she passed way too soon.
She did share her "hand-me-downs" and often would gift me her clearance rack finds that put a smile on my face. I really miss our friendship & connection.