Poor Pepper, her skin was as red and flushed as her hair right now, and he was sure she may have worked up a bit too much, but she knew better than to do that. At least she was breaking to get water. He kissed her briefly before she got off the bed and moved int position between Steve's legs. Stroking himself a few more times, he then rubbed some of the lube from his fingers around his ass, then pushed the tips of his own fingers inside. "Relax...I'll go very slowly," he said as he pressed the head of his cock right against the tight ring. One hand on Steve's knee, he used the other to guide himself as he pushed, feeling the resistance against him though he kept on, pressing a little harder until he breached his head inside of him, then giving him time to adjust before he slide another inch into him.