His balls must be bursting with little cummies now, so it is time we did something about that. I suggest you untie him at this point. As this is the first of his 2 nights of torment, he can’t have a full orgasm. That would be too much pleasure for a little submissive. We want him to experience the frustration of a ruined orgasm.
As a result, keep rubbing his cock against your pussy. Depending on how close he got to orgasm whilst you were, you may want to fuck him some more too, but get him right to he edge. Remind him he needs to tell you when he is close.
When he tells you he is close, the fun really begins. Lie on your back and make him kneel inbetween your spread legs. Continue rubbing that cock against your pussy, asking him to tell you if he is going to cum. Rub is against your arsehole too to drive him wild with excitement too. Tell him to hold it back cumming as long as he can. Tell him he isn’t allowed to cum, or he will be punished. He will be made to eat it all up. Keep going, and keep asking him to tell you when he is going to cum. Ask him if he’d rather cum and eat it up, or not cum at all. I bet at this point he’ll say anything to cum.
When he says he is going to cum, or on the first evidence that he is about to, LET GO! Your aim is to get just one stroke over the edge. He’ll get to cum, but with no orgasm. How frustrating! Let that cum drain out of his cock all over your pussy and arsehole. No touching allowed from either of you.
Tell him he has been a naughty boy, and that he wasn’t to cum. His punishment, it is lick every last drop of cum off your pussy and arse. Tell him to get his tongue inside both to make sure that he had got you nice and clean. It up to you whether you want him to keep going to orgasm or now. Ask your little sissy boy if he likes the taste of cum!