He doesn't seem to mind but I wonder if that's being cruel?
Not at all! In fact, if you've 'studied' normal mating habits in dogs, you've already noticed that they themselves often end up doing it this way. The male will mount the bitch several times experimentally and unsuccessfully. He'll stab and quest around back there a few seconds, then hop down each time to do some more sniffing / licking under her tail, then he re-mounts. Sometimes this goes on forever, particularly in size-disparate pairings, ie. a large and small breed trying to do the deed. Those can turn into a mounting
frenzy, and become frustrating, very taxing on the male. Other males catch on quicker, say by the third or fourth-ish try, so your numbers are well within spec to my mind. But yes, unless they're incredibly lucky to strike gold on the first try, then there'll (almost) always be at least a few dismounts and retries before the breeding pair finally achieves intromission to the vagina -- and hilts it to the bulb immediately for that successful, lasting penetration building toward tie & orgasm. So kudos, you're doing it right!
In fact, I myself
deliberately use this technique, to replicate a normal experience for him -- and edge him into a fever pitch, making his eventual orgasm that much better! I discussed that here, when I was answering OP on the finer points of how I do foreplay & line-up with my guys as it pertains to avoiding the pain of os bone stabs:
The last two times I’ve been fucked by a certain dog his cock has sliced me open in some fashion. First time with him there was quite the pool of blood, second time was not quite as bad. This did not happen in the previous experience I had with a different dog. Curious if there is anything I can...
www.zoovilleforum.net
Lastly: if you were ever looking to add another male to the household and hoped for a lover who thrusted much longer than the average dog before tying and ceasing the action, I've got one word: bloodhound. Dunno what it is, but my experiences with this breed in longer thrust durations have been
wonderful. They're unexpectedly hung, sometimes monstrously so (and I'm talking up near mastiff proportions). You get a huge dick on a dog who knows best how to use it -- they keep up that pounding much, much longer than the average male of other breeds. You're never left wanting more after a bloodhound has at you. Its one of our best kept secrets: they make excellent, skilled lovers ?