What would hurt more?

[John Cruz]

Heels or Converse? Im having an hour session with a mistress soon and she gave me the option of Heels or Converse which one do you think I should pick and why?

[Terry Patrick]

Converse are surprinsgly painful with the rubber sole. Most girls who kick me tend to do so in converse, though if they kick with the top of the foot it's fine. Heels tend to be quite hard so they'll hurt too. Either way, your calls are gonna hurt. Personally I love converse

[Silent Warrior]

For me, heels for the win. They set her foot up for the best contact. And then she can take 'em off easily, and ramp it up with some barefoot kicks. I don't know what it is, but every time a gal loses the heels and goes barefoot with me, the kicks get much harder, going into to the brutal zone. That usually happens when she gets a feel for what I can take, and then wants to push me beyond that. It can be overwhelming but is awesome at the same time.

[Cheryl Novot]

When I ballbust a boytoy I prefer heels.. both for offense and self defense in case things get ugly

[Hurts!]

most girls prefer  Converse  because they can have balance and get a perfect hard accurate kick in. where as hells they tend to miss a lot

[Donald Veracrow]

Tennis shoes always but barefoot kicks smack the most!