There's the strapon, of course. Make him ask you and thank you for it. There's also making him wear girl things underneath in public, and teasing him mercilessly - call him miss tinklepanties.
make him eat his own cum whenever possible. If he uses a condom, he drinks it. If he cums inside you, he licks it out. he can also give himself a facial ( try getting his plugged butt in the air, so his cock points down at his face.
Plug him up whenever, for any infraction. Use larger plugs for larger offenses.
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Diapered Sissy or harsh Shemale mistress - which side will you see?
Likes: Diapers, Crossdressing, Wetting, Humiliation, semi/discrete public, plug/anal, dares conditioned on outcomes (getting something done, sports games, etc).
Dislikes: Messing/laxative, Bondage, Cum Eating, Wedgies(don't get it), edging
Limits: super public, enema, putting food/etc in my diaper, illegal, family, pain, anything likely to cause illness or be permanent, orgasm control
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