Jilling Off

I’m a smart woman. I’m a feminist. So why are all my fantasies so demeaning towards women?

I know Dan Savage would suggest that we fantasize about the things that scare us most, but I don’t think that’s a good enough explanation.

Please insert your thoughts here.

We liked to play games, and that is why I found myself standing outside his door in a borrowed school uniform. I knocked, hestitantly, uneasy in the short short skirt.
“Enter”, he shouted, brusquely.
“Excuse me Mr. Vigeland, I was told that you wanted to see me?”

“Ah yes, Miss. MacIllewan, I’ve had several complaints about you from the other students”. He stood up from behind his desk.

“Complaints, sir? What about?” I put my hands behind my back, coyly, and turned one foot on its side, dropping a hip.

“It’s about your uniform,” he says. “It’s far too short and inappropriate. It’s unseemly for a girl your age to be showing as much… flesh”. He lingered on the last word, as his eyes raked me up and down.

“But sir,” I said, “you know I’m on a scholarship, and I can’t afford to buy a new uniform”.

“It’s the rules,” he said. “Your skirt should come down to your knees. Bend over and touch your toes,” he commanded. I did what he said, and through my legs I saw him come and stand behind me.

“It’s as I thought,” he said, grabbing the bottom hem of my skirt, one finger drawing a circle on my white underwear. “You’re going to have to be punished, Miss MacIllewan. Stand up again”.

“Oh no sir, please don’t,” I begged, sinking to my knees. “I’ll do anything to get out of the punishment”.

“Rules are rules, don’t think I take any pleasure in this. Now grab the edge of my desk. I’m going to have to give you a spanking”.

With his breath hot against the back of my neck, he pushed me down roughly so that my face was buried in the piles of books on his desk. He nudged my knees apart, and roughly pulled down my cotton briefs. Then he paused.

“We have to have rules and regulations, MacIllewan. This is for your own good. You can’t go on parading around like this.”

His hand came down sharply across my bottom, the slapping sound echoing across the room. A jolt of pain shot through me, leaving a tingling feeling. Again and again his hand came down, and I cried out. He gripped my shoulder with his other hand.

“Take your punishment like a good girl,” he said. “And I won’t have to tell the principal. You wouldn’t want your scholarship revoked, would you?”

“No sir, please don’t tell the principal. I’m sorry, I really am”.

“You should be,” he said, still holding my shoulder down. “Don’t you know what such a short uniform does to a man? You’ve inflamed me.” He pushed against me, and I felt his errection straining at his crotch. “You need to learn about life, young lady”.

“Please teach me, sir,” I begged. I felt his weight move away from me.

“Turn around,” he said. “I want to see your face so I can see how sorry you are”. I turn around slowly, leaving my panties pooled around my ankles.

“You’re not sorry at all!” he says suddenly. “You meant this to happen. Look at how loose your tie is, and how many buttons you have undone. I bet you’re not even wearing a bra, you hussy. So many dress code violations. I really am going to have to report this”.

“I am sir, I am. Look!” I unbutton the last three buttons of my shirt, revealing my red lace front hook bra.

“take that thing off immediately! That’s the colours of our rival house,” he says, stepping in closer to me, unhooking it before I have a chance to, and pushing me back onto the desk. My shirt and tie slide down my arms and I shake them off.

Now I sit topless on his desk, shivering under his gaze. The cool air brings goosebumps to my skin, and my nipples harden. “I’m sorry Mr Vigeland,” I whisper. “Please don’t report me. I’ll do anything”.

“There’s only one thing for it, Miss MacIllewan,” he says. “I’m obviously going to show you why we have these rules. I have to show you why you need to cover yourself up.” He takes my hand, and puts it on his crotch. “This is what you do to a man when you reveal your flesh like this. And now you need to deal with the consequences.”

He unbuttons his fly, and pulls out his cock, gloriously thick and errect “Have you seen one of these before?”

“Only in pictures, sir,” I stammer, trying to conjour up a blush.

“Then this is going to hurt you, but believe me, it’s going to hurt me a lot more,” he says, spreading my legs, and pushing himself inside me.

I let out a gasp, “Oh Mr. Vigeland,” I cry, “You’re hurting me, it’s too big!” He grunts “This is your punishment,” and thrusts harder into me. I put my arms around his neck, pulling him against my body and cry out again. “Fuck me harder Sir! Teach me again” before a giggle escapes me, which he smothers with his mouth.

One of his hands roams up to sieze my breasts, while his other spasms, knocking books onto the floor. I lock my ankles behind his back, pushing him deeper and deeper in. He kisses my neck. “Call me sir again,” he commands, panting. His cock slides in and out of me underneath my tartan skirt, and he pulls my hair so I arch my back as he runs his mouth down to suck a nipple.

“Oh sir,” I moan, “please don’t report me. Please, oh sir, SIR” An wave takes me, running up and down my body, and I scratch his back with my nails as I come, one glorious orgasm after another. With a cry he comes too, and we lie back against the desk, smug in the aftermath of a lesson well learnt.