This situations sort of reminds me of those Role Play conventions where folks take a vacation and go out and dress up as Sailor Moon or whatever. To be honest, in your situation, it seems like a healthy idea - a group of friends who take a good trip every now and then and dress as their preferred role for a bit, letting off the steam and having some fun. And then when you get back home, it's back to the male role and providing support and stuff for your female partner. Sounds like a typical couple, though with a straight couple, that vacation may be more along the lines of a group of guys hitting Vegas for a couple nights...

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Sometimes, when one has lived life up until middle age and is scared to change the norm, just breaking things up every now and then, like a vacation with some RP friends, or a few nights out on the town with that group, can make life seem worthwhile. Sometimes it's not always best digging into one's most secrety desires and seeing them all come true at a time where you're already older and transitioning fully may not be the best decision, especially with a family at stake. Taking things more conservatively can be a healthy option; there really is so much pressure to go through with something completely just because everyone else gets to, but that's not always the exact life everyone should have.