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

A bit of ...anal sex...

... look as good as possible for my man. He's got a few surprises coming tonight. "You ready, sexy?" I call out. He's ready, and out I step. I hear his breath let out, ending in a low whistle. "Oh. My." His reaction is not unexpected. I'm not wearing lingerie, my usual, and I'm not naked. I'm dressed in a white and plaid schoolgirl outfit, but it's not the slutty kind, it's a legit, and somewhat conservative one. White knee highs, plaid skirt, white top, and underneath it's equally conservative, plain white cotton bra and panties. I'm wearing only a touch of lipstick and eyeshadow, and my hair is in a very plain ponytail, with only a white scrunchie and a white plastic barette with only plain silver studs in my ears. My contacts are out and my old glasses are back. I look so nerdy and plain, and hopefully, innocent. "You wanted to see me Headmaster? Miss Taylor said it was about some rules that had been broken?" I leave this wide open for him, and I hope he has fun with it!! "Why yes, yes, I've heard that some of you girls had been getting well, a bit rowdy. Now I don't know what's going on, but I know we have very high standards here, and I expect all girls to live up to them." "I don't want to be in trouble, my parents will kill me!" I whimper. "Well, let's see, right off the bat, I do smell wine on your breath. Janet, do you think this is acceptable behavior for young ladies?" "No, I just wanted to try it. I've never drunk before." "You also realize we check out girl's ...

... computers? I know you've been looking some things are very inappropriate for you!" He's getting into his role quite well. I'm also getting wet, this is kind of fun! "Headmaster, I'm so sorry, please don't tell my parents! Please!" "I have standards I'm supposed to follow, too, you know. Last month, you served two detentions, and that didn't seem to stop you. I think maybe a different punishment is needed." "Anything, Headmaster, anything! Please!" I'm not so bad of an actress, I think I'd be pretty plausible here. He shakes his head. "I'm not sure what to do, nothing seems to work for you....unless we try something old fashioned." "I'll do it, I beg you." "Well, then we'll try it. Over my knee young lady. We'll see if some old fashioned discipline works for you." I've never done anything like this, but I'm soaking wet now! I assume the position over his knees and he yanks up my skirt, and softly caresses my ass. Then his palm slaps it hard! I let out a yelp as I didn't think he'd spank me that hard, but another follows quickly! I started this game, I'll see it through! A total of 20 and he stops. "Well, let's see if you're ok, I do need to be concerned about my girls' health." He slips my panties down and caresses my ass again, and this time a finger slides into me as I've got a bit of lube in me. It feels soooo good. Then his fingers go further and he slips them into my soaking pussy. "What is this? This is supposed to be punishment, young lady, not some sort of....kinky fun! What ...