contemplating venturing out with the wife

[Shelby]

No, not yet; we might venture out in the Spring........who knows? You're right about being lucky; I can't imagine trying to explore this side of my personality with someone who is not supportive.

[Ralitsa]

Why wait for spring? In spring you will want to wear a light skirt and top, open toed shoes....
In winter it's easier to get away with a sweater and jeans, or sweater dress and boots. Not saying you should hide behind your clothes, but we've all done it.
For a first time out, I'd think winter would be an easier time.

And Eileen has very good advice, pick a place where you're not likely to cross paths with the problematic demographics. Starbucks is a good choice for a first time. Plenty of weird people there, nobody cares, if they care they should go somewhere else. Coffee shops in general are like that. I'd be willing to bet that Starbucks is just itching for a chance to challenge the NC law in court - and they have the money to do it too.

So it doesn't need to be a major outing, just go out for coffee one morning.

[Emily]

For a first time out, I'd think winter would be an easier time.

Agree 100% Sometimes the layers just help!

[Anne Bonny]

A supportive and encouraging wife...why not go out!? She is there with you...go for it!

[Shelby]

I guess I am waiting until I can get a better handle on my look before venturing out and trying to pass as a woman. Keep in mind I am still very new to this and don't have an extensive wardrobe nor and I very well versed in the intricacies of applying make up.

I hope to be able to start experimenting on a more regular basis very soon which will help me get more comfortable in my own skin.

[Anne Bonny]

I call the problem shyness because it is quite similar...we feel everyone is focused on us and thinking negatively...it's not true for the most part. Many never notice us, some do and only a few really think negatively but mostly to their selves.