Ive not had much problem putting condoms on, sometimes it takes some work to get it over the head if he has a thick one but once its on then the length part is easy, if he's big and very hard i often find myself using my teeth to nudge the condom down the length then use my hands to slide it down further if he's long.
Some men seem to struggle maintaining an erection when the condom goes on so sex isnt possible. Sometimes what i then do is take the loose condom off continue to suck/lick then ask him if he likes 69, if he says yes i discretly reach for a condom while changing position, slowly sneakly get the condom out while your both giving oral, place the condom somewhere ready for when he's hard then put the condom in mouth and slide it down his length while you continue sucking him, say things like i cant wait to have you inside me, then turn around and lower yourself onto his cock and ride him asap to keep him stimulated - hard. Obviously do all the other things to turn him on like show enthusiasm that youre enjoying it a lot, look into his eyes, passionatly kiss him, feel his chest/nipples, get his hands to squeeze your boobs, rub his balls if he likes that, mourn etc.