for anal, a strap-on is a must for you; for maximum humiliation it should be larger than his dick, perhaps much larger. Then you have something to work towards. But start small, ice cubes, a few pencils, or a small plug are good starter options.
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Likes:
Light to moderate pain - Giving dares - Asking questions
Dislikes:
Hard pain - Jacking off - Semi-public - Wedgies
Hates:
Extreme pain - Urine - Full Public - Involving other people
Limits (Will never do these)
Permanent damage - Involving Family - Scat - Involving Animals - Crossdressing - Eating Gross stuff
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