IndyShellie28 said:
Over-your-knees (OTK) spankings, administered with a wooden paddle as if your budding sissy-cuckold were a small child, would constitute suitably-humiliating punishment.
A possible strategy would be to grade him on his housework at the end of each day, with his grade based on how well he carries out his assigned chores (use a checklist). Then, if his grade-point average for the week is suitably high, as defined by you, give him a maintenance spanking... not too severe... to remind him who's in charge.
If, however, his grade-point average for the week is too low, give him a relatively severe spanking with your wooden paddle — one that really reddens his bottom, and perhaps even reduces him to tears. Fairly soon, you should find the quality of his housework improving, perhaps dramatically.
After you have finished spanking him and he has done some "corner time" (perhaps ~20 min. with his nose in a corner), I suggest fucking him anally with a suitably-sized strap-on. If you haven't done this previously, you should probably start with one that's relatively small, then work up in size as he becomes accustomed to it. If you use a vibrating strap-on, the vibrations on your clot may enable you to orgasm while you're fucking him. That should also result in "milking" your duck, such that prostate fluid drips out the end of his chastity device. (This may require fucking him anally for quite a while, perhaps ~30 min. initially, but as time passes you may be able to "milk" him in progressively shorter time periods.)
See, for instance:
Strapon primer:
http://www.take-it-like-a-man.com/index.html