For me the funniest thing during my transition phase, before I went full time, was at a staff Christmas lunch in 2013. It was a freaking hot day (Sydney, summertime) and all the women were wearing great summer dresses which in itself was a bit depressing to me since I couldn't, but I kept telling myself "next year, you will too". Now about two days earlier I had given myself the gift of a full body wax... arms, legs, chest, underarms, butt... uh, TMI maybe... and I was wearing a short sleeved shirt and a pair of knee length shorts. It was post lunch and we were all sitting around a large coffee table, chatting and drinking when all of a sudden one of the women suddenly commented on my legs being smooth and hairless. She was a cyclist and wondered out aloud if I had shaved them for cycling as many guys also do that. With a huge grin I said "nope, full body wax".
This was clearly very fascinating to the female contingent around the table (comprising about 85%, I think). She wanted to know why and I just laughed and said "why not?" Three women there (including my boss) who already knew I was trans and that I was on HRT and in the process of transitioning were kind of in on the joke but said nothing. The other women were really fascinated while the two guys, both of whom were very hairy, seemed to blanch a little. A "man" getting a wax job is still fairly unheard of after all! The first woman asked if she could have a feel of my legs and I said "be my guest" and she did. I know that sounds a bit weird or kinky but considering we were all a bit tipsy, very relaxed and friendly and I had a huge crush on her it was one of the happiest moments of my life!!!!

It was great being the centre of attention of a bunch of women like that, I was so close to just blurting out that I was trans. Considering I had a number of drinks in me by that stage it was amazing that I could keep my mouth zipped!
Anyway, it was a fun and funny little moment... still makes me smile fondly. When I came out at work three months later and transitioned to full time I think it really answered a lot of questions from that Christmas lunch!