Scared as I Plan my First Outing

[SatinSarah]

I have an opportunity to dress and go out for the first time next week. I have been dressing for over 30 years and have never managed to find the courage to go outside yet! I did dress for fun as a student/ fancy dress but that wasn't the same.

I have been preparing my outfit and bought a coat last week. I only want to go for a short walk to know I can do it. I have a loving wife who knows all about my crossdressing and allows me to dress at home with her- but not with make-up wigs etc. we have agreed boundaries which I don't want to spoil. I get to dress with her fairly regularly - especially after Strictly Come Dancing when she knows I really enjoy the dresses!

I think I have attached a picture below of the new coat, shoes and jeggings I have bought.

I just need reassurance, tips and courage to step out. I think my make-up & wig if I get it right will be fine. I know from other posts that I just need courage to be myself and not to worry about what people think.

I am doing it at this time of year because it will be dark. I intend going out in a safe crowded area - perhaps into a few shops in London.

I am so excited but also scared. Please help me know I am doing the right thing!

[Shelly Preston]

Hi Sarah

All I would add is wear some sensible shoes. Heels look great if you dont have to walk too far, so go for a lower heel if you have any walking planned.

Otherwise the outfit looks great for shopping.

Have fun and try to relax you wil enjoy it even more.

[becky77]

If I was to go out and I haven't yet, not in public anyway. I would choose normal heels, I love heels and yours are eye catching and generally you don't want to draw any kind of attention, at least I wouldn't.
Otherwise what I can see looks great. Your braver than I am, good luck.

[kimdl93]

I agree on th shoes. Something a bit more sensible for that first step out. But I have another question. Is your wife OK with you stepping out the door? It seems that if she's not yet comfortable with wigs/make up, that she might have problems with this.

I can't tell you how to overcome her objections to seeing you in a wig...but maybe you should work on addressing her concerns, then take that step out together.

[Noel Chimes]

First of all is FULLY on board with the whole package? (make up, wig, etc.) You said that you two had boundaries. If she is in agreement with EVERYTHING, then go for it and have the time of your life. But be warned, once the cat is let out of the bag you won't be able to put her back. Welcome to the outside world.

[Gizmo, Debbie]

Looks like you are dresed to blend in so that good.
The first time you open that door your adrenaline is gonna be pumping and you will see and question the slightly of looks or actions you see from anybody..."did they read me?", "was that just a friendly smile or a i know what you are smile? sort of thing.
Go out fully expecting to be "read" ( cause it's unrealistic to think you won't be?). To then just complete ignore everybody. Keep your chin up and shoulders down and smile.

You CAN DO IT if you realy want to and i'm sure you'll be fine..

Enjoy the walk and we want to hear all about afterwards.

[Jana]

If you dress age and venue appropriate, have a good wig and decent makeup, you'll be surprised at how little attention people will pay to you. I must warn you, though: once you start venturing out of the house, you'll never want anything else! (and that's a good thing, because being inside the closet sucks)

[Erica Marie]

From the pic what I see I would never guess. I agree with some of the other girls, for your first walk in public you may want to go with a lower heel. Dont get me wrong, they match and look great with your outfit. But you may feel more confident if you dont have to worry about walking safely. Just a suggestion

[SatinSarah]

Thanks so much everybody - my heart is racing with excitement already. I agree about the heels. I have much more sensible ones and know I should wear them! I am comfortable in these heels and can walk easily but I think you are all right - these are for the 2nd outing!

My wife has boundaries about what she wants to see. She knows I am able to dress fully with make-up and wig at another property

[Melanie Sykes]

It's a lovely outfit, and your idea of going to a busy shopping area in London is excellent - much better than somewhere lonely. I think you'd be doing the right thing in wearing lower heels this time! Once you've done it once, you won't want to stop and will be looking for every opportunity. I know you'll enjoy it!

[Claire Cook]

I have an opportunity to dress and go out for the first time next week. I have been dressing for over 30 years and have never managed to find the courage to go outside yet! I did dress for fun as a student/ fancy dress but that wasn't the same.

I just need reassurance, tips and courage to step out. I think my make-up & wig if I get it right will be fine. I know from other posts that I just need courage to be myself and not to worry about what people think.

I am so excited but also scared. Please help me know I am doing the right thing!

Hi Sarah,

You are indeed! Yes, don't go with those shoes the first time. The coat is really nice. You'll have all of the juices going, you'll be nervous but just remember that the hardest part is that first step out the door. I think all of us remember our first time, and as others have said, when you're done you'll be looking forward to the next time -- enjoy!

[linda allen]

I agree on th shoes. Something a bit more sensible for that first step out. But I have another question. Is your wife OK with you stepping out the door? It seems that if she's not yet comfortable with wigs/make up, that she might have problems with this.

I can't tell you how to overcome her objections to seeing you in a wig...but maybe you should work on addressing her concerns, then take that step out together.

As usual, Kim nails it. Is she going out with you? Does she know (and approve) if you're going out alone?

And the shoes - unless you're 5'2" tall, go for something more conservative. I suggest flats or one or two inch heels at most.

Have your wife check your makeup. If she suggests changes, do it.

[bridget thronton]

Enjoy you can do it

[Jenniferathome]

There is no reason to be scared, as you have read here many times. If you don't want to attract attention, will your outfit blend in where you are going? Do women wear heels where you are headed? Go do some people watching in this location on the same day/time to see what works. When you go, walk with confidence.

[LaraPeterson]

Love the heels and the coat. . .go for it! You ARE going to be nervous, you WILL likely stumble, someone might even notice you. So what. Be yourself and enjoy yourself. You have obviously worked hard for this moment. It's yours and don't let anybody take it away from you. The world awaits. . .Sarah is going to be surprised how much she likes it!

[Beverley Sims]

I would be scared of falling off those high heels.
You look great, London has always been friendly to me in the evenings and I have had a good time out.

[Closettran]

I like your outfit Sarah, it's smart but won't look out of place at all, and like others I would go for a lower heel. I wore just ballet pumps when I went out earlier this week, which were probably too far the other way, not really the kind of thing most GGs would wear in the winter but all I had. I would have killed for a nice low-heeled ankle boot!!

Hope to see some pics of you out and about.

J xx

[Launa]

You'll do fine. I have been out about 8 times now and its getting easier each time.

[SatinSarah]

Wow you look amazing - I can't believe you haven't been brave enough to fo out yet looking that good!

[GondorRachel]

"It's a dangerous business, going out your door. You step onto the road, and if you don't keep your feet, there's no knowing where you might be swept off to."

I like the outfit, and not knowing your heels experience over long distance/different surfaces, can't say whether those shoes are a good idea. I know that for my first outing in public I wore sneakers (pink, but flat). I also went with a friend, for both moral support and strength in numbers. I have since gone a few more times, each time gets easier (though still scared each time.).

[Diversity]

Hi Sarah,
With a new coat and being in a safe and crowded area, you'll most likely be fine if you dress to blend in and do not dress flashy. Deep breaths, relax, and stready as you go! Don't be too hurt if people don't appear to notice you, as it only means you're doing a great job!
Good luck!
Di

[Aylineira]

Have fun with it! Remember that nobody is actually looking at you unless you give them a reason.. so relax!!

[Angela Campbell]

Yes it is frightening....but it is also wonderful too. I have gone out a few times and every time is just as stressful as the last. I still love it though!

[roby54]

I have been out and about,at first i just wore a skirt or boots,ten some makeup and boobs,the other day in omaha on a Sat morning i was out for 4 hrs,I went to 3 Kohls stores a Burlington Coat factory.2 Tuesday mornings stores in a dress with boobs ,makeup,my purse and just shopped like the woman i was.No one said anything.i did have one sales woman that frowned some as i bought a dress,Alot of how we feel we do to ourself,and it does not hurt that i do not live there but i do not think it would make a difference,Now i am 6ft tall and 275 lbs so i am not a small girl to pass very well,so i have to just do it

[AllieSF]

Great advice for such a big first big step. My only recommendation is to take small steps while actually out and about. Small steps help you slow your pace like a woman and help you to truly enjoy the moment and all the other wonderful sites to be seen. You look fine to me and please do not hesitate to look others in the eyes and when they smile at you, don't nod your head as us males are likely to do, just smile right back at them. You will do great and please let us all know how it goes.