If your sissy has sensitive nipples like me, here is a good procedure for you to try on him.
Get a set of nipple suction tubes, the kind you pump by hand. Place the cups on your sissy and pump them 20 times or so.
Wait for half an hour or 45 minutes until his nipples are dark, swollen and distended. This in and of itself is pretty intense.
Put on a pair of plastic gloves so you don't get any bad effect, and get some serrano chile peppers. Cut a one inch piece off and score the end with a knife so it will splay out.
Pull the suction cup off the nipple of your choice. Hold a finger on either side of the nipple and press down towards sissy's chest to further elongate the nipple. At this point the cunt boi will be writhing.
With nipple fully distended, take the chile and insert the tip of the nipple inside it, and press in. If you scored the chile right, it will be taking his swollen nipple inside.
Once fully inside, crush the chile & nipple HARD! Press it, twist it, squeeze it in. Sissy will likely be making noise now, tie down cunt boi if necessary.
Take a second chunk of chile and repeat, with more intensity this time. Leave some of the seeds clinging to the nipple and the irritated skin around the areola.
Repeat with the other nipple. If you leave the seeds on, they will continue building heat and irritation for 40 minutes or so. Its best to leave then on!
When you allow sissy to wear clothes, he will be painfully aware of his nipples.
If you are feeling mean, you can do the same thing to the glans (cock head), shaft, scrotum, and if you are really mean, you can make a ureteral insertion of a q-tip that has been rubbed in the chile juice/seeds.
After all this, you may also insert your still gloved (covered with chile residue/seeds) finger(s) into the slaves rectum
It will remind him of his place in life!