Tutoring - How Hard Can It Be?

"Let's do something simple next."

"If we must."

"Portugal."

"Easy, that's the one on the far left."

"Spain."

"That's the one right next to it."

"France."

"Oh come on, I've been there. I think I can find it on a map."

"Andorra."

This gave her pause, the cocky attitude fell away and she looked down at her textbook. "The fuck? Is that even a real place?"

"It is," I answered her. We were set up in the study. It had been a few days since I had first arrived at Woodham manor and so far was making very little progress. Annie's "condition" came with no shortage of difficulties, most prevalent of which was just getting her to pay attention for more than a few seconds.

I tried not to indulge her cravings more than necessary, my intention was to wean her off the constant stimulation she was used to and get her accustomed to something more stable but that was very much still a work in progress.

"Where the fuck is it?" She muttered, staring deeply at the geography textbook in front of her. This was a middle school level assignment and she was still struggling with it. I don't know if it was due to her condition or just that nobody ever expected much from a spoiled rich brat like her. "There's so many places that aren't Andorra..."

It didn't help that she was always trying to tempt me when her cravings started to hit. Most of the time it didn't work, much to her frustration. Even now she decided to wear her private school uniform. A white button up shirt with the school's emblem stitched into the chest. A dark red tie with yellow stripes. Both the shirt and the tie were unbuttoned and loosened enough to show as much of her cleavage as possible. A pleated plaid mini-skirt that was most likely several inches shorter than regulation. It was accompanied by thigh high white socks and shiny black shoes. Her hair was tied in pigtails and she wore glasses that I was fairly certain she didn't need. Really going hard on the clichés.

Though my outfit wasn't much better. A black suit jacket that was neatly fitted to my figure with a maroon button up beneath. A black skirt to match the jacket that hugged my hips tightly and came down to my knees, which were covered by nylon stockings with black heeled shoes. My hair was tied back with a band and in all fairness I was also wearing glasses I didn't need but they tied the outfit together so nicely I couldn't resist. They were small with rectangular lenses that hung just below my eyeline.

Annie crossed her arms, and likely intentionally, pushed her tits together as she looked down that the textbook. "Fuck it, I give up."

I pointed to the larger map set up with a yardstick I had found, "Right here," pointing to the small country nestled between the much larger Spain and France.

"Oh fuck off, seriously?" She asked. "I can hardly see that, I thought it was a smudge on the map!" She looked back down at her book, "This one doesn't even show it! It's just like a little dot!"

"That's why we study," I said to her, lightly tapping the yardstick in my hand.

She groaned with exasperation, sitting back in her chair. "I fucking hate studying," She said. "It's so boooring!"

I glanced at my watch, it was nearing the end of the day and she probably wasn't going to get anything more done at this point. I could tell she was at least trying to apply herself, I had to give her that. I couldn't really blame her, I was also a terrible student in school. I suppose she earned a reward for her efforts.

"That's what happens when you're such a bad student," I said to her seductively. "You fall behind, and in my class, bad students get punished."

It took her a second to realize what I was going on about, but the confusion on her face melted to a sly smile. "Oh and what kind of punishment did you have in mind?"

I smiled before suddenly grabbing her by the back of the neck and forcing her to bend over the table. Her little skirt did nothing to cover her ass, which was only barely covered by a white cotton thong as Annie struggled beneath my grip. It was only an act, I could tell she was just playing along. "Ooh, what are you doing!?" She said weakly. Her acting could use some work as I yanked the fabric of her underwear up, pulling it tight against her, the white fabric disappearing between her asscheeks as I took the yardstick in hand and slid it against her ass, I imagine it felt cool against her flesh.

"Y-you won't get away with this," she said, struggling to keep up with the act. "When my father hears about this-"

I interrupted her with a prompt swat on the ass, not very hard, just enough to get her attention. Her voice shot up all the same.

"Your Daddy won't hear shit," I said, placing the yardstick back against her ass. "He said to teach you by any means necessary and if this is what it requires for you to learn, so be it." I swatted her again, a little harder this time. My other hand was still on the back of her neck and I felt her entire body tense at the impact as her voice cried out in a mix of pain and pleasure. "Do you understand?"

"I-" She started but I smacked her again, her ass was starting to turn shades of red. "I want to hear 'Yes Miss Maria' and nothing else." I smacked her again, "Do. You. Understand.?" Each word was emphasized by a slightly harder smack on the ass.

"Yes Miss Maria," She panted out. I let go of her neck, I knew she wouldn't move. She knew better than that. I rewarded her with another smack on the ass, firm this time. I could see her tense up, but her voice cried out like she was climaxing, it wouldn't surprise me if she was.

"Now, repeat after me," I told her. "I am a nasty little slut." Smack.

"I am a nasty little slut." Smack.

Who cares more about her pussy than my education." Smack.

"W-who cares more about.." she hesitated.

"Her pussy," I reiterated.

"Her pussy... than her education."

"Good girl," I told her, and smacked her again, hard. Her body shuddered and her voice caught in her throat. I waited for her to find her voice, to cry out. I was surprised at how well she was taking it. She hadn't yet used our safe word, (Velveteen), so I kept going. With both hands on the yardstick I swung. like a baseball player going for a home run, the smack across her ass rang out loudly against the walls of the study. The yardstick broke into two pieces as the other clattered to the floor. Her voice cried out loudly, her legs gave out and she fell to the floor. She was panting heavily, tears welled in her eyes. Again I waited for the safe word, but it didn't come.

"I-I'm sorry Miss Maria," she said, continuing the scene, even as tears streamed down her face. I could only imagine how sore her ass was. "I'll be a good student. I promise!" Her face was red and her makeup was starting to run, but if she wanted to continue, I wouldn't stop her. I sat in a nearby chair and crossed my legs, extending one foot in front of her.

"I'm glad to hear it," I said as I looked down at her. "But I think you need to prove to me how dedicated you are."

She didn't hesitate, with careful motions she removed the shoe from my foot and kissed the top of it. I could feel her lips against the nylon stockings. She moved up to my ankle, slowly moving up my leg with a trail of kisses to my thigh as I hiked my skirt up to allow me to spread my legs.

Beneath my clothes I was wearing a matching black lacy bra and panties with a garter belt. Annie's lips graced each of my inner thighs before landing between my legs. I smiled and stood up, forcing her to sit back on her sore ass. She fidgeted as I removed the suit coat, slowly unbuttoning the shirt and sliding my skirt off. "Let's hope you actually paid attention to this lesson," I said as. I slipped my panties off and beckoned her closer.

She stood on her knees in front of me as I guided her head to my shaved crotch. Her mouth opened obediently and her tongue met my pussy and slid against my clit as a moan escaped me. She had improved greatly in the past few days. The way her tongue worked the lips of my pussy, knowing when to go for the clit. I moaned more, I was starting to cum already. I gripped the back of her head and held it between my legs as I pressed myself against her face.

When my climax subsided, I released her. She panted as she looked up at me, her lips wet with a mixture of my juices and her saliva. Her eyes said she was waiting for the next order. "Get up and bend that ass over," I told her.

She slowly got to her feet, her legs were shaky but they held as she positioned herself against the edge of the table and presented her ass to me again. Her ass was a deep red color and I almost felt a little bad, maybe I had overdone it a little. I reached out to touch her, gently my fingertips trailed across her ass. She shuddered against my touch.

With both hands I grabbed her ass. She cried out and shuddered. "Do you like when I treat you like this?" I asked.

"Y-Yes Miss Maria," she responded.

"And why is that?" I asked.

"I'm a dirty slut, Miss Maria," she panted.

"Good answer," I said as I reached up to slide her underwear down. I didn't bother getting it all the way off as I exposed her ass and pussy. She was already soaking wet between her legs. I lightly smacked my fingers against her pussy, causing her to moan out. "And this is the pussy you're so obsessed with?"

"Yes, Mis Maria," she said between moans. I slipped a finger into her, causing her to moan more as moved in and out of her for a moment before withdrawing. Now that same finger, coated with her warm fluids, and prodded her asshole with it.

"And this ass?" I asked, "I bet you get a lot of use out of this too?" Slowly my fingertip pushed into her.

"Y-Yes! Yes Miss Maria" she groaned as my finger stretched her a little, slowly working it into her until it was as deep as it could go. With my finger up her ass she was putty in my hands. I teased her like that for a moment before pulling out.

"Let's see what these holes can do then," I said as I dug around in a black bag I had kept to the side of the room. From within the bag I withdrew an anal wand. A long black piece of silicone formed into a line of large rounded sections about the size of a kiwi fruit, it ended in a large ring. Alongside a bottle of lube that I used to cover the tool, as well as pouring some over her asshole, I pressed the head of the wand against her ass, prodding it slowly until her ass opened for me, allowing it inside. Again and again she took each section one at a time, her voice groaning out each time.

I knew she could take it up the ass but this was a bit deeper than anything I had used on her previously. At the last two sections I seriously thought she'd be at her limit, but to my own surprise she managed to take them. As the last section slid into her ass, I could see her body spamming lightly, knowing the process had made her climax. "It's so deep!" She managed to pant.

"You'll get used to it," I said, reaching into the bag again. This time I pulled out a dildo, already fastened into a strap-on harness I slid it on, grabbing my temporary fake duck and lubed it up as well before guiding the tip to her pussy.

"Oh god," Annie gasped as the head slid in, I slowly pushed the shaft in until my hips met. Her ass, pressing against the wand's ring, pushing it against her ass. "Oh my god," Annie gasped again, panting heavily, but still no safe word came. So I continued.

I reached down and grabbed both her pigtails in my hand, pulling hard and forcing her to lead back against me as she cried out. My other hand gripping her hip I started thrusting. I wasn't easy on her, thrusting hard right out of the gate. She was doing well but I had the feeling she might break soon. I was pushing her a lot harder today than I have previously.

With all of this stimulation it wasn't long before she was cumming again, her entire body froze up and she cried out. If the dick I was using was real it probably would have been enough to make me cum in her. But I held it inside her until her body relaxed and she collapsed against the table. "I think that's enough for today," I said as I slowly withdrew from her, pulling the wand from her ass and helping her up.

"That... that was," she panted as she leaned against me.

"You did very well," I told her, "I'm surprised you didn't use the safe word."

"I...I might have forgotten what it was," she admitted, "but it's okay. I'm glad I didn't use it. I can't remember the last time I came so hard. I thought I was going to pass out."

"Well, let's get you washed up," I told her. I gathered our things and clothes and helped her walk to my room. Ever since my first night she had been staying with me instead of her own room. We squeezed into the standing shower in the bathroom and washed ourselves. When we were finished, dinner had been delivered on a rolling cart. It just so happened to come with an ice pack I had requested earlier, though I never told them exactly why we would need it.

We didn't bother with clothes after the shower, we sat on the couch, Annie sitting on the ice pack as we watched television together. Once dinner was finished, Annie laid her head in my lap, but it wasn't long before she was asleep. I let her lay there for a few hours as I gently ran my fingers through her hair until I myself got tired.

Annie was completely out and didn't even stir as I got up and carried her to the bed, tucking her in.

I was about to step over to the other side and climb in myself when I noticed something. The closet door was left slightly ajar. I didn't remember leaving it like that and walked over to it. Normally I would have closed it and thought nothing of it, but there was this draft that was coming in from inside.

Finding it odd I opened the closet door and stepped inside, inside the closet, at the far end I could see there was a small opening in the wall. I approached it and pushed it open further. It led to some kind of secret passageway, it was then I realized why it had been left open like this.

Someone was watching us...