Flies do it upside down
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I note that there have been several examples of insects in situations like this on WordPress. It’s not surprising as insects’ life spans are generally very short. The corollary of this is that if you spend time taking photographs of insects it will not be long before you observe the same.
In a similar fashion damselflies and dragonflies are beautiful creatures to see and photograph, but they are also brutal carnivores. In fact I was shooting a fly and a damselfly flew in and ate it.
The only challenges here are: having enough depth of field to get both parties in focus; setting a high enough shutter speed to avoid blur and getting enough light.
In most cases this interaction takes place in a small space, and it is therefore possible, not easy but possible, to use a tripod.
And by the way flies do it in any orientation they like. Vertigo does not seem to be much of a factor.