"Ah!" Calista starts, reacting instinctively to the slap. "Leaving my skirt on, huh? It does look pretty good on me." She lets out another gasp as the chill is fingered into her, preparing her virgin ass to receive Lee's endowment. She tries her best to relax her ring, having read that it eases insertion during some "research." Hands gripping the sheets tightly, she lowers her head to join them, thinking Lee will enjoy the sight even more as his length prods her rear. "F-fuck!" Overwhelmed by a pain she was decidedly unready for, Calista's suddenly glad she looked away from the man, not wanting to show the intense, shooting hurt stemming from her hole. It wasn't supposed to hurt this much! Thankfully, the sensation is brief, only lasting a few tryingly long seconds before fading into a content fullness. She can't tell how much of Lee's cock is actually inside her stretching hole, but it already feels so much deeper than her own fingers could ever reach. Catching her breath, she raises and turns her head to face Lee again, giving a small nod. "Go ahead, but please be gentle." She concentrates on keeping her sphincter as relaxed as she can, given the circumstances, to stave off any lingering pain as he begins to rock back and forth.