I think every man has had the experience of having 'trouble' getting aligned with his lady for penetration at least once in their life.
It may take several attempts to get positioned for her honey hole, and I've always found it frustrating. It's like when you are so hot that you've just got to feel yourself in her pussy NOW, and anything that gets in the way is wasting time.
In any case, I've always thought this is what gives a cuck the most pleasure from guiding another man's hard cock directly to the target. We understand the urgency and desire to get in her pussy immediately, and whatever you can do to make that happen is appreciated greatly.
The exact same applies when you have to spread your wife's lips open. You visually sight the target, and can guide his weapon with precision.
The best thing about repeating the process if he pulls out of her pussy is that it shows the cuck is paying attention and is prepared and ready to help with anything at a second's notice!