"Maybe because I'm not trying to leave you with a sore ass this time?" He murmurs, smiling and burying his head in her neck, his teeth digging gently into her skin. He pulls his fingers out and lines his bottom dick up with her asshole. "Now relax... This might hurt just a little bit." He says, pushing into her tight ass as slowly as he can, not more than half an inch at a time. His free hand reaches up and starts groping a breast, squeezing and kneading it as he tries to take it slow and not ram himself into her like every muscle in his body is screaming at him to do.