Advice

[Natalee Brooks]

Hi Ladies,

Got 2 current issues in facing.  First, there is a local toy shop that I go to for clothes toys etc. The shop owner there is super sweet and friendly.  She’s been super helpful for me helping me get new heels, clothes, etc.  She knows that I’m a crossdresser and is totally ok with it.  I’ve worn an outfit underneath my clothes twice now to go shopping at her store and I want to show it to her but I’m unsure how to go about it.  Any tips/advise?

Second,

I’m going on a vacation back home and seeing friends and family.  I have an old friend that I’m stopping to see.  He and I have fooled around some in our past.  Now there’s a chance to re visit our situation that never had closure from before.  What should I expect or not expect going forward with this visit.

[Laura Lovett]

Hi Natalie

As I know nothing about your situation, I cannot advise on the 2nd issue – but, for the first, there are 2 nice ways to play it:

First, and this is what I would do, since she knows, you could ask straight out if she would mind if you came into the shop dressed.

Several years ago, my chiropractor, who has two businesses (the second being a more exotic version of massage!) asked me if I wanted to have a massage from her newest employee, who is a trans girl.

I declined, for personal reasons, and said straight out that I would rather turn up wearing a dress myself – which, of course, is the truth!

She laughed long and loud, then said “I’d really like to see that”.

Naturally, I obliged, much to her surprise and delight, and now she insists that I go to my sessions as Laura, and only calls me Laura in communications and in person.

Before each session, we have a cup of herbal tea and a girl chat – it’s so lovely to have someone who has completely accepted this side of me!

The second approach, since she knows, could be just to turn up in your outfit and surprise her.

If you’re not fully mentally prepared, it could be awkward, so you’d need to be in a calm place inside – difficult when your heart is pounding with adrenaline, but nevertheless exciting, and not as safe as the first option!

So, it depends on how you want to play it.

Obviously, I’m only pushing towards what worked so well for me – but I hope this helps, and have fun. I am sure it will be a blast!

Especially the walk from the car to the shop – assuming you do that rather than go in underdressed and remove the drab in the changing room, although whatever makes it work best!

Hope it goes well, and DO report back!

Love Laura

 

[Sutekina]

For store girl, ask if you can show yourself dressed because you want her opinion and advice.

[Natalee Brooks]

Thank you Sutikena!  I hope it is that simple.

 

[Jones]

For the store I would just ask her if she would like to see you enfemme on your next visit. For the friend I would take an outfit in the car and ask him if he would like to fool around with you dressed.

[Natalee Brooks]

Hi Jeannie and Laura,

When I return home, I should have a new pair of heels waiting to be picked up and that’s what I’ll do.  I’ll ask if she would mind me coming in dressed so maybe we can find me some actual going out clothes and makeup.  All I have is lingerie and there’s a few festivals and parades in NOLA where wearing lingerie is fine but I have only a couple of shirts and jeans that just aren’t really good for going out.  IMO. As far as my friend, I did that Monday and he turned me down but left me with hope, so maybe it’s just not the right time.  Mardi Gras 2022 is coming up soon and he’s never been.  I think that’s when it might happen.  He’s fine with me dressing up for him and he says I’m beautiful but he’s still grieving over the loss of his wife last year. I am respectful and understanding of that too.  We talked alot Monday and cleared the air between us.  It felt good too.  So, fingers crossed, I can at least get my shop keeper to keep helping find my inner woman and maybe even be a better and more thorough woman when he comes down for MG 22.  I’ll follow up next week on my shop friend.  She’s been a breath of fresh air lately being understanding and so helpful finding heels for me since I do wear a size 16 heel.  She’s a wonderful woman and I’m thankful I found her.  Y’all have a great day.  Thanks for all your support and advice. It helps.

Peace n love 💕,

Natalee

[Jones]

😊💋

[Author]

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