My little sister has a female friend who has been her "Best Friend Forever" since they were both about seven years old. I have fond memories of the girl coming over to my parents' home see my sister, and the fun things they did together - including sleepovers and participating in group activities with our family. More than 40 years after they met, they are still best friends.
This woman was like another little sister to me when we were growing up together. And honestly, if there had been a few less years difference in our ages (I'm 5 years older), and if she hadn't been inclined to think of me only as her 'big brother from another mother', I wouldn't have minded dating her myself, when I was still in high school. She got married soon after she graduated from high school, they've had a son and a daughter, and she and her husband are still quite happily married today. I haven't seen much of her or her husband in person since I moved out of the area more than 30 years ago. I last saw her and her husband when I was in Oregon for my father's funeral and interment at the cemetery, in 2012. We're Facebook friends (on my male side), and I consider her to be 'extended family'. But I have no romantic interest in her, nor does she with me. There is absolutely zero chance of anything intimate ever happening between us - first, because she is married and I have a strict policy against messing with married or partnered people, and second, because she, like me, is over 50 and probably not interested in being intimate with anyone other then her husband (and maybe not even with him, at her age). We're friends, but we don't see much of each other in person. I simply know her as 'my sister's best friend forever'.
Of course, she doesn't know about my feminine side... My accepting and openly expressing the girl inside me developed after the last time we saw each other in person.
Well, yesterday I got a request from her for a personal favor. It's the first time she has asked for a favor from me since I was in high school, decades ago. Her job is to help to put on some sort of educational seminars, and her work on those takes her all over the region, going to each town where a seminar will be held, with a team of other people, and spending a week there doing the seminar. Normally, they either put her up in a hotel, or arrange for her to stay with a family in the town where the seminar is being held. But in July and again in August of this year, she is scheduled to work at seminars in the town I have moved to, and her organization was unable to hook her up with a hotel or a host family. So she reached out to friends, starting with me, for crash space. She knows I am living here now, and that I have a lovely new home, with plans to be able to accommodate visits from friends. The town I am in is a good hour and a half drive from her home. Much too far to commute to the seminars from her home.
Now, I am certainly not going to turn her down. And she really won't have much impact on us during each visit. She would arrive mid-week in the afternoon, drop off her stuff and go to a pre-seminar coordination meeting with her team at the seminar site, and then to dinner with them, returning to our home after 10 PM. For the next 5 days after that, including both days of the weekend, she would rise fairly early, probably leaving before 7 AM and grabbing coffee and pastries on the way to her seminar, and not return until after 10 PM. We will set her up in our studio, which has a private entrance, a toilet and a sink, as well as a mini-fridge, microwave and hot plate. There is no shower or bathtub in the studio though. She will only need to come into the house to use the bathtub and shower next to my daughter's bedroom, or to use our hot tub in the back yard to relax after a session, late at night. It's possible that on one of those nights she might forgo dinner with her team and have dinner with us instead, if my daughter and I are open to eating a late dinner, after 7 or 8 PM. Or I might get to chat with her over a cup of tea after 10 PM, if I choose to stay up on one of those nights. But for the most part, we'll hardly know she is here, and she won't have much time to objectively look at me and notice any feminine aspects about me. She would leave on the morning of the day after the seminar.
For her first visit, with as little contact as she will have with us, my feminine side probably won't even come up. I can easily enough refrain from doing any girly stuff at the times when she will be at our home, and there will be no need for her to even look into my bedroom or bathroom, aside from an initial 'tour of the house'. At worst, she might get a good look at how little body hair I have now if I share the hot tub with her late one night. I'm expecting it to go similar to my last weekend's overnight visit with my two sisters in law and their husbands, in their town. No one noticed how my nails were done or that I had earrings, and my sister's BFF will see less of me than my sisters in law or their husbands got to.
The second visit could be more tricky. Saturday of that second week-long visit is the "Pride Festival" in my town. I'm planning on attending the Pride festival as Ceera, and probably helping to run a table there for one of the LGBT groups that I am part of here. There will probably be other LGBT events that week I will want to attend en-femme...
I can probably just time things so my 'girly time' is happening while my sister's BFF is at her seminars. Or if I do get back en-femme at a time when she is around, odds are good that she will be in the studio, and unable to see me arriving and going through the main part of the house and into my bedroom, to change back to male mode. The studio has no windows facing the driveway or the front of the house.
The challenge with all this will be that if she does notice my earrings and nails and shaved body hair, or catches me in other girly things or fully en-femme, what will she tell her best friend, my sister, who does not yet solidly know about my girly side? There's probably a better than 90% chance that by the time this lady arrives, my sister will have mentioned to her best friend the girly things my sister noticed on her own recent visit to my home, but didn't have a chance to talk to me about. Especially once her BFF mentions that I will be giving her crash space like this. I do not believe the request for crash space was initiated solely or even partially as a means for her BFF to snoop over here. But between now and the visits, my sister might ask her BFF to keep her eyes open and clue her in to what she might notice.
In a way, I hope she does at least ask about my nails during the first visit. Then, depending on how that goes, it might not be an issue if I choose to have a more girly polish on my nails for the next visit.
Life shall continue to be interesting, as I dance along the edge of disclosure. There is no need to force the issue. But if it happens that I get outed to my sister's BFF, I won't blame her if she tells my sister. I could hardly expect best friends to keep a secret like that from each other. Not when it is something about her best friend's brother!