Damon just wants to make her cry. Everything he does works toward that goal. While she may be getting fucked and vibrated, it will never be enough to block out those intense canings and spankings.
And after a short trip through the wilderness he is going to lead her back to the barn and have his way with her some more. The iron brace that PD uses to restrain Dia is ideal for a number of interesting uses.
Veruca James is slowly and skillfully teased to the edge of orgasm over and over again, but denied permission to cum.Tied down to a mattress, knees spread wide and hood zipped tight, she is completely helpless.
Tess Dagger has been caught and put in a barrel. At first she struggles, but a weekend in isolation makes her more compliant. London pulls her head out of the barrel and locks her body inside. With her face completely at London's mercy Tess gets a face whipping. London isn't done. Tess is hung up like a piece of meat with a chain through her crotch. The pinching little links are attached to her wrist restraints so that every time she moves she tugs on her most sensitive bits. Then London starts her assault. She punches and canes Tess. Then she vibrates Tess' sensitive little clit. The barrel returns and this time just Tess' feet are exposed. London puts harsh clips on her toes and the tops of her feet then she whips and canes her sensitive soles.
She cannot be released from her shackles since she may try to escape, so PD has to use alternate means of getting her heart pumping. His chosen method is a combination of physical labor and physical pain.