I administer a few fun punishments to my sissyish boyfriend, but this one is my favorite:
Note: He doesn't do anything to warrant these punishments. I guess I'm just mean like that ;)
I'll dress my boyfriend in a sexy but sweet outfit. Usually a short skirt, soft lacy panties, a tank top, and a cardigan. I'll do his makeup and nails too, and claim that we're going to have a girls night. But after a little while, I take out his red anal vibrator and make him sit on it. I turn it on the lowest setting and tie his hands behind his back. I leave the room and go to my kitchen to prepare a lovely sissysnack. It's two scoops of ice cream with a banana in between, covered in hot fudge and whipped cream. Oh, and utensils aren't allowed during the consumption of this delicious phallic sundae. So I return to the room and make him eat it with his hands behind back. I tease him about how much he loves this cock-shaped sundae as I change the settings on the vibrator. After he comes, I'll scold him about being so messy. Then I'll clean all the ice cream remnants off of him and take him out of his sexy outfit. I'll put him in thick diapers and plastic panties, and a silly dress. I spend much of the remainder of the night rubbing his sore bottom and teasing him about being such a little bitch.