Well on Monday I did it. I went out in the wild for the first time as Jean. The original intent was only to go dressed to my therapist then straight back home. However there was also this dress I saw online you see, at my favourite retailer, only 20 min away from my therapist's office. So I really wanted to go try it on.
On top of that on the 60 mile drive to the therapist, I ended up having to go P really, really bad. I had to pull off in a service area/truck stop. There was NO WAY I was going to go into the men's room of a truck stop all dolled up! So I screwed together the courage and went into the ladies' room (which turned out to be empty). Quickly did my business (feet pointing the right, i.e. feminie, way!), got out, got back in my car, and drove on.
At the therapist I had a good session. I asked her two questions at the end. I first asked "what do you see sitting in front of you"? Her answer was unequivocal: "a woman". She added "a woman who like all of us has to work hard to look her best, but clearly, a woman". Second question, did she think I could go out to shop for my dress as I was? She said "I don't see why not".
So I again mustered the courage, drove to the shopping complex and got there 20 minutes before closing, and strode into the store head high, went straight to the counter, and asked the very young SA about the dress. We quickly found it on the racks in my size. I asked if I could try it on and she unhesitatingly said "of course!", and led me to the fitting rooms. It fit, I loved it (a nice pale pink patterned light summer dress), and bought it (I doubt she rarely saw such a decisive woman shopper!). Not once did she betray that she "read" me. I have no doubt she did, but to her credit just treated me like any of her other women clients. I walked over to a costume jewellery store a few stores down and did the same, and bought a nice necklace that I thought would go well with the dress. Quick trip to the ladies' again before hitting the road, and lastly near home, fast food drive thru as I didn't feel like cooking dinner (my wife was away overnight).
Well, my head didn't get bitten off. A few takeaways:
1) I was dressed conservatively in a skirt, blouse and blazer like a woman just finishing work in a client-facing office position, and it was near quitting time so I did not, at least clothes-wise, look out of place;
2) I acted like I owned it... walked confidently, did not hesitate to interact with the SAs; even if read, they probably figured this was someone serious about their identity.
3) It seems easier to shop en femme than in drab for women's clothes. In the latter cases, I always had to interact with the SAs about who/what I am, call ahead, etc., in order to have them comfortable with a man shopping in their store and trying on clothes; I was never turned away or treated with disrespect but I did feel the need to prepare the ground as it were. Dressed and acting as the woman I was that day, I seemed to "belong" more. In 2018 as more and more trans people come out of the closet, younger people seem more ready to accept us in the identity we are affirming, rather than the one we were born in. All of the people I interacted with that day (except my female therapist who is 71!), were young women.
4) In my early 60s, many women of my age don't look so great either... so maybe the line between masculine and feminine becomes a bit more blurred as we age; I'm just another ugly old woman! But it is easier to look better at this when young.
Nobody questioned my gender, nobody laughed, nobody turned up their nose. Either they don't care, or it doesn't matter to them.
I know iffy encounters do occur, but we shouldn't let that interfere with our freedom.
The ice has finally broken and I am from now on going to shop for clothes in my female identity as much as possible.
Originally Posted by Becky Blue
