How about if sub #2 gets one peg off if he gets Kaiden to cum within a certain time and that peg is put on Kaiden, but gets an additional peg - perhaps on his balls - if he fails? Once Kaiden cums he'll either have both #2's pegs on him or #2 will have pegs on his balls as well as his tits depending on the time limits you impose. Then they swap places, no release of the pegs which are added as before. Perhaps his cock could be pegged as he's vibrated too as additional punishment for not getting Kaiden off in time.