I better do it gently now

I've already taken a big risk in just shoving it in her unprepared anus. She took it surprisingly well, which is nice but I won't risk that again. Sure she's warmed up now so it should be better, but I can always push for more later on of I start slow.

I place my spongy head against her pink rosebud and it immediately tenses up. I can get her peep out a "sorry". She starts relaxing and I start to wiggle my cock around digging carefully into her tight little hole like a drill.

Just having my head press against her like this drives me crazy. "Mmmh fuck" I moan as I enjoy myself. Maisie misunderstands this for irritation.

"I'm really sorry, maybe it's just better if you force it in? I don't think I can relax enough, your cock is just too big." She sounds almost ashamed and I feel sorry for her.

"No Maisie it's okay! This can take time, you got an unbelievably tight ass but don't forget I've already been in you once." I calm her.

"Yeah but to get there you had to use brute force remember and while it hurt like hell then. Now you've warmed me up and I'm ready for it. So I'm willing to give it a new try!"