Anne

"I am going to take your ass," I told her, keeping my voice gentle, but making sure that she could look into my eyes and know I meant it.

She had to strain to look at me, but she was meeting my gaze. She was tied up, her wrists cuffed to the bed, lying on her stomach, her head turned sharply to the side in order to see me.

She moaned a little. It was barely audible, but I could hear it.

I knelt so that she wouldn't have to strain, and ran my hands down her bare back. She shivered a little as my fingers moved against her skin.

I smiled at her, as calm and reassuring a smile as I could.

I said, "You want that, don't you?"

She licked her lips. Her wrists strained against the cuffs. She did not speak.

I said, "Don't you?" My voice was sterner now.

Her brown eyes looked huge and frightened and she said, "Yes."

"Good girl," I told her. I rose and moved towards her ass. I picked up the lubricant from the floor.

No one had ever taken Anne's ass. She had confessed as much to me, confessed that she was frightened, scared it would be painful. She loved some pain, of course—she loved to be spanked, to be punished, to be humiliated. She loved to be made to kneel before me and beg for my cock. But something about the pain of being taken anally was too intimate, too personal for her. So I knew that she would be very frightened.

She was beautiful, splayed out there on the bed, completely helpless. I took her legs—I hadn't tied them—and repositioned her so that she was kneeling. I said, "Are you ready, sweetie?"

It was a formality, of course, but formalities are everything in sex, sometimes. She moaned, and I took it for a yes—she knew I would. I put some lube on my fingers and moved them into her asshole. She flinched a little bit, and I made a mental note of that. I spread lube as best I could in and around her anus, making sure to coat it heavily, and then I stopped and moved back to stand by her head again. Her head and eyes were down, and she was squirming a little.

"Look at me, Anne," I said.

She followed orders, still squirming.

"Stay still," I told her, letting some of my anger show.

She froze. She knew the tone. She knew what it meant.

I said, "Why did you flinch when I touched you, Anne?"

She said, "I don't know."

I moved quickly, then, reaching underneath her and grabbing her left breast in my right hand. She moved up as far as she could, repositioning herself, not daring to impede my access to her. I had trained her well.

I said, "You know you're not to flinch. You know I don't like it."

She said, "Yes." She looked very frightened.

I was stroking her breast now, teasing it, enjoying her discomfiture as the nipple expanded beneath my fingertips. I pinched the engorged nipple, hard, and she made a little sound.

I said, "You know you have to be punished for that, sweetie. Don't you?"

I pinched her nipple again to emphasize the point.

She said, again, "Yes."

I smiled. I did love her very much. There was something wonderfully tender about the moments when she accepted her punishment. Even spanking her was an act of tremendous intimacy, as she allowed me to access her, to control her, to take her in the most literal sense of the word.

I said, "That's better." I kissed her lightly on the lips, and then harder. She opened her mouth, and we kissed for a few moments. I moved my hand away from her breast, stroking her hair, holding her face against mine. I said, after the kisses had abated, "How high can you count, Anne?"

She shivered in absolute terror. I said, "How high?"

She knew I did not like to repeat myself. "Ten," she said. "I can count to ten."

"Ten is good," I said. In truth, I hadn't expected her to volunteer anything over five. "The hairbrush or the crop?"

"No, please! Please!"

"Which one?" I asked, getting exasperated.

"The brush," she said. "The brush."

"That's my girl," I said. I took the hairbrush off her nightstand. "Kiss it for me," I said, presenting it to her.

She did as commanded, and I moved behind her. "Now count," I ordered her. I took the hairbrush and smacked her with it, giving her no time to prepare herself.

"One!" she shouted.

"That's very good," I said. "You barely flinched at all that time. You feel better, don't you? Knowing how much you've pleased me?"

"Yes," she whispered, so softly I could barely hear her.

"Yes," I confirmed. "Are you ready for your next one?"

"Yes," she said again.

I let her wait for a moment, and then the brush came down again on her beautiful pale ass, reddening it for a moment. I stroked the redness, wishing that we did not have to waste time with such preliminaries, wishing I could simply take her ass right that second. But rules are meant to be obeyed, always.

I continued to hit her, and she continued to count. By the time she got to nine, her ass was reddened, and she was crying freely, tears pouring down her face, and I stopped for a moment, going to her, drying her tears, kissing them.

I said, "You are going to have to get a little more comfortable with this. You're still thinking of it as pain."

"It hurts!" she nearly screamed.

I did not match her frantic tone. "It's supposed to hurt," I told her. "You know that. But it's more than that. It gives me pleasure, because I know you are accepting the pain for me. You are, aren't you?"

"Yes," she said. She was quieter now.

"Good. I know you want to be a good slave. You just need more training. But you're getting better." She didn't say anything. "You know that, don't you? You know I'm very pleased with your progress."

"Yes," she said again. "I know."

"That's good. Now, you have one more to take. But I think you need a few extras, just so you can get accustomed to punishment. It bothers you too much, and we can't have that, now can we?"

She did not answer, but I didn't insist on one.

I said, "Just ten extra, Anne. And each time I do, I want you to thank me, for allowing you to please me by accepting them."

I did not wait to see if she understood. I was beginning to enjoy myself, truly beginning to take as much pleasure in her punishment as I was going to in a few moments by taking her ass.

She moaned deeply as I repositioned myself over her ass, and then I brought the hairbrush down again.

She jerked sharply against her bonds, but immediately afterwards she murmured, "Ten. Thank you."

I smiled and picked up the crop. Without a word of warning I brought it down on her reddened ass.

She screamed in agony. I waited for the scream to subside, and then said, "What do you say, Anne?"

"Eleven. Thank you."

Again the crop came down, and again after that, until she had counted all the way to twenty.

"That's very good," I said. "You deserve a treat."

I grabbed her reddened ass cheeks and pulling them apart. She moaned, and I ran my fingers against her asshole.

She flinched again, and I said, "Later," putting as much menace as I could into the single word.

I reached one of my hands beneath her, moving it against her pussy. She was soaking wet. I picked up the keys to her cuffs, and, leaning over her body, I uncuffed one of her wrists. I whispered, my mouth near her ear, "Touch yourself." She didn't need any more encouragement than that. I moved up, and as I did she began touching her clit, urgently.

I said, "Are you ready?"

She moaned. But I wasn't asking for permission—I was asking to inform her that I was ready.

I spread her ass cheeks again and I took her anal virginity, entering her. She let out a little yelp as she felt my cock enter her, pressing against her, filling her. I pistoned against her, rocking back and forth, as her hand ran against her clit and I kept my fingers on her reddened ass, now and again enjoying her moans of pain as I ran my finger across one of the red welts I had created in our earlier games.

I came soon after, as did she.

And as we lay there, spent, with one of her hands still cuffed, I said, "You know you flinched before, when I was about to fuck you."

"I know," she said.

"Later you'll have to be punished for that. You know that, too."

"I know," she said again.

"In public, I think," I said, smiling at the thought. "You'd like that, wouldn't you, sweetheart? To have vibrators shoved deep inside your ass and pussy while we took a walk down the block?"

She stayed silent a moment, and then she said, "I'd love it if you loved it."

She really was learning. I kissed her, untied her, and held her, stroking her, running my fingers soothingly against her reddened ass, and thinking that in a day or two the welts would clear up, and we could begin her training again.