A bit of ...anal sex... - Sex Stories

A bit of ...anal sex...

... a few moments and he pulls out of me slowly. "Oh, god, I'm sorry, your dresser-" I put my fingers on his lips. "Stay with it, baby, stay with it!" He grins. "Well, I hope you realize how important it is for you uphold our standards, and I..." he says nothing more as his cock is already in my mouth, I know it'll take a few minutes, but I'm up to the challenge. I gently lick it, lick his balls, caress his thighs with my fingers as he cools off, and then I can get him hard again. It's only a matter of a few minutes and he's growing in my mouth, and work him gently and he's rock hard again, and it's time for my introduction....to a bit of anal play...... "That's excellent work Janet, and I think you understand, but I really want to make sure this lesson sinks in properly." He pushes me to the bed. "Get on your knees, if you're going to be that kind of girl, you'll do it properly!" he snaps. He gets on the bed and gets behind me and I feel him squirt some lube on my ass as his fingers gently rub it in to me. Even in a role playing scenario, he's gentle where it counts. "If you're going to take cocks, you'll take them every way your headmaster wants them, is THAT understood?" "Yes, Headmaster!" I feel the head of his cock line up with my waiting ass and he ever so gently pushes it in a little at a time. "You okay?" he whispers. "It's all good baby!" I whisper back. "OOohhh Headmaster, it's so big! You're hurting me!" He drives his cock all the way inside me, but carefully, and ...

... holds it inside of me so I can get used to the situation. It feels....wonderful, and he does feel huge, but I like the sensation of my ass being full. He slowly starts to fuck my ass and I push up against him to get all of his cock in me. "You like your ass fucking? You like being that kind of girl?" "OOhhh yes, Headmaster!" He starts to pick up the pace, and now he's giving me a good ride. I LOVE having my ass fucked by him, and then his hand slaps my left ass cheek. "You like it when your Headmaster fucks you good, you little slut, DO YOU??" "Yes, yes I do, fuck me harder!!" he does and he does and he does, after his first, he's good for a bit, and I'm getting all of it!!! The slaps add to it as each one is like a little electric shock to me, and I wonder what else might feel like that? As good as it feels though, I don't feel like I'm going to come, I feel....like my orgasm is somehow blocked? He's pounding away and I enjoy each deep stroke, but coming may be an issue as I realize he's not far off from coming himself and I really want to come from this! Just as he goes into his final strokes and I hear him groaning I reach back and rub my pussy for a second and I......explode with an orgasm that I shriek out as he pounds me to a stop. "Aaaaaaaahhhhhhhhhh!!!!" He holds me tight as I come and we've almost achieved simultaneous orgasm from anal sex! We sit there for a moment and he very carefully pulls out of me and I notice he's got a towel at his side in case there's any mess ...