I carry pepper spray all the time and have background in Kyokushinkai, Taijiquan (Chen) and Xingyiquan (more than two decades). Pre-transition there were couple of cases when I interfered into ongoing streetcrimes (three guys in their very early 20-ties) taking on one drunk and looked angry and mean enough to scare them off. I had fights with several people who were intended to take me down and 4 guys could not pin me... I was also able to deal with two average dudes with minimal training with getting myself punched once or twice.
So, a couple of months ago I asked my best male friend to do some friendly spar and we agreed that I wont do any dirty fighting, like kicking him in balls, shin-kicking or trying to get my elbow into contact with his jaw. So, my options were somehow restricted and he has some decent background in grappling. As soon as he was able to break the distance, he grabbed my arms and it was over very quickly with him pinning me down on the floor. We both agreed though that while he was going for that grab, I had plenty of options to unleash some pain onto him, but we agreed beforehands not to. So... my conclusions were that two guys would now be a serious problem unless I am able to deal with one of them very quickly (pepper spray?) and if I can, I should not try my chances to get into hand-to-hand combat even with one male assailant, cause his level of aggression will be much higher due to testosterone advantage, plus he will have extra strenght and psychological advantage (the last one if quite an interesting point, cause my friend admitted that he did not considered me a serious threat anymore and was actually holding himself a bit, whereas for me, as soon as he was literally in my face, he suddenly looked much larger and scarier then he used to be... and I used to give him some HtH lessons like 5-6 years ago...).