Tutoring Session

Jay showed me into the office. I am not sure why he needed to talk. Most of my cases are already wrapped up for the week. He looks at me through his glasses.

"Rich, I'd like to take your temperature on something," he says taking out his phone. "What do you think of Maria?"

"She's a good paralegal," I say. "I worked with her on the Wilkinson case. Have to say, she's probably the reason we won."

He nods, "Right, but you know what I mean."

Yes, yes I do. A few weeks ago, after we won the Wilkinson case a few of us were caught on camera at a gas station celebrating like frat boys. Maria let her hair down and took off her bra dancing for us. Her nice full tits were bouncing to the beat. It was glorious. But a week later the boss had me to his house and let me have Maria. That was an experience.

I closed the door and took a seat, "I, um, I think she's amazing. Why do you ask?"

"Would you like to date her?" Duh.

"Associates can't date paralegals; those are your rules, not mine."

"There may be a loophole. I want her to get her law degree. You're right, she is competent, but shall we say her priorities are not in order. I think you can be a good tutor. Make sure she passes, by any means necessary."

We shake hands and I straighten my tie. The boss tells me that she'll be leaving the office to go to school full time at his expense. This could be fun.

Maria,as it turned out, was a good student. She would show up at my office after hours and we would discuss her classes and her assignments. She had her priorities mostly straight. I stole a few touches here and there, but she didn't seem to mind.

The boss set up rules and regulations for how to handle Maria if she, in his words, slipped up and sent me an email before all of this started. I tried to discuss it with her, but she stopped me stating she knows his rules and she was okay with it.

A few months in, she showed up half an hour late. Her black hair was wet and up in a bun and she was wearing bright pink yoga pants and a yellow tank top. Her black bra was poking out ever so slightly.

"Rich, I'm so sorry. I had a bad day and laid down for a nap."

I try to hide my amusement. I have been waiting for this. "Well, why don't we talk about it?"

She pursed her lips and tilted her head, "Well, I mean, I just..." she stopped and looked down before she blurted, "I failed my criminal law test."

"Oh darling, that sucks. You know what this means, right?"

Her lips quivered but she nodded.

Damn. Being late constituted a spanking, a swat for every minute late. But failing a test, that was another story. I crossed to my filing cabinet. It held a wooden paddle I was to use if needed. I palmed it, but I didn't like the weight.

"Maria, we're going to go off book. Don't tell Jay."

She looked up at me with those big, brown eyes and nods. I motioned to the table the boss ordered and she dutifully bent over. My stomach jolted at the sight. She was nothing if not compliant. How far could I take this?

I slid my belt from the loops and laid it on her back. Then I pulled her yoga pants down, her ample firm ass was already bare. I was okay to do this, just nervous.

"Are you ready?"

Maria sounded a little annoyed. "Yeah."

I took my belt in my hands and cracked it down. She yelled out in pain but I saw a hint of a smile on her face. I could feel my pants tighten with arousal.

"1," she counts under her breath.

Omg. I have to do thirty of these? I crack on quickly until her bottom is red and we get through the thirty. Plus 5 more for that little burst of insolence. She sighs and takes a huge breath. I hear her sniffle.

I rub her hot, pink cheeks and pull her pants up.

"Are you okay?"

Maria looks at me with tears in her eyes, "I'm okay."

"Are you going to be on time next time?"

Gulping trying to re-catch her breath she nods.

I return to the filing cabinet. I get out ties, hand cuffs, a riding crop, lube and a metal buttplug. I lay my tools out and sit at my desk.

"I need you to strip naked now. Come stand in front of me so I can watch."

She stands up, kicks off her shoes, and the tank top follows. She unhooks her bra and I have to sit on my hands. I want to feel those perfect titties with the perfect little nipples in my hands. But not yet. She has shaved bare since last I saw her naked. Pushing my desire away, I tell her, "Back in position."

Back to the table she goes. I tie her legs to the posts and secure her arms in front of her.

"What was your grade?"

"34 out of 100," she whispered.

"Dang, girl. That's sixty-six more with this little thing," I said twirling the riding crop in my hands. Maria just closes her eyes.

I lecture her on the importance of college and how it was rude of her to repay her Uncle's kindness by failing so badly. She is in tears by the time I am through with her muttering sorries left and right.

"Sorry will not help you now," I finish my lecture with a firm swat of the riding crop on her pussy.

"OWWW, MOTHERFUCKER," she screamed angrily.

I breathed in, 1..2..3, and did it again on her thigh. She howled. I hated how much I loved it. I caught the other thigh and alternated about forty swats.

I finished out on her pussy but at that point I could hear the crop come down with a splat. And her howls became pleasure filled.

Her pussy was puffy and just begging for some cock. I toyed with it watching her squirm. Then I took the lube and poured some on her ripe little ass. I started to rub it and pressed the butt plug right in. She was moaning and groaning like she enjoyed this punishment. Maria lifted her head the best she could.

"I'm not allowed to cum."

"You better cum." I retrieved my aching cock from its prison and slid into Maria. She's tighter and more sensitive. But I could feel her holding it back every time I thrusted into her. So I leaned down and whispered in her ear, "Cum for me, princess."

Goddamn, did she ever listen. I felt as if my cock was in a vice grip. Her body and the table trembled as her orgasm kept going. I had to stop for a second.

"Everything alright?" Maria purred.

I untied her and snatched her up by her neck and gestured with my eyes. She squatted before me and licked from the tip to the shaft before she wrapped those luscious lips around my member. She took it deep. I watched her masterfully please and taste herself on me. Her right hand slipped between her legs after a bit but I couldn't have that. I greedily wanted to feel all of her orgasms that day.

I pulled her up to me and kissed her deeply while pushing her back down on the table. I pushed myself into her hearing her sigh in relief. I pumped slowly until she was on the edge then I quickened my pace. Maria yelled out in pleasure. I stopped and went slowly again. She grabbed my neck when I was close and she was on orgasm number four. We finished together as she whispered "Rich" into my neck.

All of the sudden the air was thick with feelings we both knew we shouldn't act on. Maria stammered out, "I...I'm going to get dressed. Can we tutor tomorrow? After class?"

I just nodded my head yes and stood there stupidly watching her leave hoping it would not be the last time.