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Wanting to go out for the first time

11 Posts
11 Users
45 Reactions
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Posts: 4
Lady
Topic starter
(@marriedcrossdresser513)
Eminent Member     Illinois, United States of America
Joined: 10 months ago

I've never left my house when I've been dressed up but really getting the urge to do so. 

Looking for advice on what to wear and any tips to make it successful

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10 Replies
3 Replies
(@tubbydullard)
Joined: 2 years ago

Honorable Member     Citrus hills, Florida, United States of America
Posts: 333

@marriedcrossdresser513

Oh Please DO IT! IM DRESSING in dresses, skirts. Night gowns bras panties, wigs, jewelry, AND EVERYDAY NOW.

I HAVE straight women now donating Maxie skirts to me. And offering advice about all sorts of feminine skills, how to sit, keep your knees together when you wear those skirts,  don't pad your bra too big, it won't look  normal etc. It's such a wonderful world Being Stephanie, I'll never go back to drab dressing.  AGain.

I offer you encouragement, get out and do it man.You will love it.The excitement will put a smile on your face.You can't remove.!

 

 

 

 

 

 

 

 

 

 

 

Https:// 

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 4016

@marriedcrossdresser513 Whatever you do, OWN IT!

Your attitude and confidence will help you carry off whatever you are wearing. If anyone says anything to you, complimentary or not, respond respectfully with a smile. If it fits, use some humour.

If you don't want to stand out, figure out how you can be stealthy.

If you do want to stand out, then do it with class.

You know what is in your wardrobe, to carry off what you want to do.

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Lady
(@darbygirl)
Joined: 10 months ago

Eminent Member     Massachusetts, United States of America
Posts: 22

@marriedcrossdresser513 

Hello Kayla, I'm Darby and I've just joined the site. I've dressed for years but only started venturing our in the past 20 yrs. Having been a commercial photographer for my career, I've worked with some amazing makeup artists, one in particular who worked at my studio for several years.

Makeup is important and there is so much info, techniques and people showing beautiful information on YouTube!!! Eye lashes, mascara, eye shadow and lipstick will certainly get you started and feeling pretty!

The first times I ventured out was before the internet but I had clothes, wigs (OMG way to many wigs!!) and could "blend in" with what I had. Going out for night drives (taking those little steps), several times and then after 3 or 4 drives, going out and stopping for gas and cigarettes and then driving down to NJ from Massachusetts was an absolute joy at night!

Now, I just jump in the car to the mall and if a guy whistles, sometimes I'll go over and tease him, flick my hair... or recently do a Mae West routine. I also get a good laugh... at a guy's expense, when I'm walking down the mall with my heels clicking (I have always love that sound!) and a guy with his girlfriend/wife pass me and I hear a "thud".. and I say to myself, well, there's another guy that turned his head and looked at me a second time and got hit by his lady! LOL

You know, it's the little things that let you know that you really do look good LOL!

It's all fun and I think every one of us who have experienced going out... sure it is crazy, your heart is beating out of your chest but each time you do go out... know this that your building confidence and practicing makeup and walking and mannerisms and are getting more and more comfortable with yourself and being out and about!

Highly recommend going out, slowly at your own pace and enjoying every experience!

Hugs,

Darby

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Posts: 59
Guest
(@Anonymous 95775)
Trusted Member
Joined: 10 months ago

I’m just like you. I got a makeover in a distant city, but I knew too many people at the conference hotel so abandoned my plans. I doubt I’m recognizable, but also confident I would not pass. I’m excited to hear the advice. Thanks for posting this. 

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Posts: 7829
(@aliceunderwire)
Illustrious Member     Near Burlington, Vermont, United States of America
Joined: 5 years ago

Hi Kayla,

Often it’s best to blend in when you venture out.  I find most people are more absorbed in their own thoughts and don’t even look at you.  So do some scouting to see what women your age are wearing running errands, catching a bite to eat or enjoying a cup of coffee.  And use that as a starting point.

Alice

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Posts: 1069
Managing Ambassador
(@melodeescarlet)
Famed Member     DC/Baltimore, Maryland, United States of America
Joined: 2 years ago

@marriedcrossdresser513 I think it depends on where you're going, who you'll be with, and how you want to present yourself.

My very first time out was Pride. Knowing I'd be among open minded people, I opted to make a bold statement, but for that crowd that was 'fitting in'. If you're going to the grocery store then you'd likely want to tone it down some and fit in with that crowd.

If you haven't worked on your makeup skills, then I'd start there first - or have someone do it for you. I believe it will be the first thing people look at.

Otherwise - absolutely, make a little plan and go for it! 🙂

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Posts: 812
 Leah
Baroness
(@leah63)
Noble Member     Minneapolis, Minnesota, United States of America
Joined: 7 years ago

All great advice,  know the area you are going to be appropriately dressed to blend in...unless you want to stand out...lol.  Depending on how passable you are, you will be nervous regardless. You will feel like everyone is looking at you.  The hardest part is shedding our male walk and mannerisms.  It does get easier each time and it is VERY exciting

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Posts: 1118
Duchess Annual
(@firefly)
Noble Member     Panama, Panama, Panama
Joined: 7 years ago

You have already received better advice here. The environment in which you are going to present yourself is important. As many ladies here know, I was fortunate that my first time was at Keystone, in the company of people like me and in a very accepting environment. It made it easier. 

Prepare well with makeup. I had never made one so complete. Use simple decorations. A knee-length suit or skirt. I wore elegant clothes because it was a dinner out. Depending on what you are going to do you could go casual. When you're ready, don't think too much and go out. Enjoy it. It will be a lasting memory.

Gisela

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Posts: 2172
 J J
Lady
(@jjandme)
Famed Member     California, United States of America
Joined: 5 years ago

Wow, there are so many options and ways to go about this. The most important thing is to jist do it. 

I could write a thousand words on this based on my own experiences, and the experiences and posts of others.

As I see it there are two main options, the subtle stap by step approach, or the go all out approach. Of course there are an infinite number of steps inbetween the two.

One can start small and build. Just go for a drive partially or fully en femme, usually at night. Then maybe stop for gas or a quick trip to convience store. Maybe step up by taking a walk in a safe placeat night. Just add a little more with each attempt until you are comfortable.  The other end of the spectrum is to just go out fully en femme. Maybe start with a dressing service to get your outfit and make up just right. Some .even arrange a tea or drinks together for moral support. I version of this is going to a CD event so you are surrounded by like minded people.

My two biggest take aways is one, this is an extemely fun and rewarding thing to do, and two, nobody cares. I do not pass close up (but I think I am passable just at a glance), but I have never had an issue or comment except for compliments.

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Posts: 130
Duchess
(@theapat)
Reputable Member     Massachusetts, United States of America
Joined: 1 year ago

Dear Kayla,

I needed to figuratively hit the replay button on the DVR in my mind... The FIRST TIME, I remember being all dolled up, sitting in my auto, adjusting the rearview mirror, admiring my feminine finish, putting on a touch up coat of lipstick, hypnotized by my dangling ear rings, finally starting the car, opening the garage door, hyperventilating with excitement, and finally backing up and out of my garage ONLY TO CLIP/CHIP my driver side mirror frame.  Not an expensive repair but I quickly 'picked up the pieces' and decided to venture out. I guess it was akin to Alan Shepard's suborbital flight. Barely 15 minutes in the car, heading to a nearby shopping mall, then getting out of the car, pretending I was checking on my front and rear lights. I'll never forget. Scoop neck top, Miniskirt, Nylons, Pumps, being outside, winter, the sensation, the reality. I walked to the store front only to pretend I forgot something in the car. Back in the car. Mission accomplished. I didn't want the night to end. Drove home. Opened the garage door. Laughed at the side mirror incident.

Nothing like pouring a glass of wine at the end of your 'first flight' (NO MATTER WHERE YOU GO OR HOW LONG YOU ARE OUT) and celebrating your accomplishment. THUMBS UP. Be patient with yourself. Baby steps. Everything in time. You'll be navigating the globe before you know it. YOUR MISSION to the MOON will be one we'll all want to hear about.

Stay Well, Keep Safe, God Bless, and Continue to Enjoy what you love doing.

Sincerely and With Love,

Thea

PS....OH and take plenty of pictures....for the memory and for analysis.

 

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