My Schoolgirl Session – Anything for Grades

My old client, Todd, called me with a new role play idea. We were once again going with the schoolgirl fantasy but this time, it was the forbidden territory of blackmail and BDSM punishment. Last time, we held a spanking session, but this time he wanted to do more. Since I loved our previous encounter, I agreed. We talked for a good hour on the phone, discussion boundaries, our desires and a safe word. Like the last time, we would pretend the hotel room was a classroom, but this time he wanted me to be there before him. I didn’t know the exact plot, he said it would be a surprise, instead I was going to go with an improvisation method “yes, and…”. Everything he says, I’d take as a true statement and add onto it.

I arrived for an outcall at the  Mayfair hotel and easily picked up the reservation. I went to the room, my client already placed the table and chair in the middle, in front of the counter. It created an illusion of a teacher’s desk and a student’s. I sat down and took out a book, to read while waiting for “my teacher”. A while later, I heard the door open and straighten my back.

“Hello, Miss Jenkins, nice to see you here so early,” Todd commented, stepping inside, “To what do I owe the pleasure?”

“I wanted to discuss my grades.” I shrugged and stood up, nervously playing with my short skirt. “Um… Passing grades, to be precise.”

“Oh, right, you’re not doing too well with these, are you?” he gestured for me to sit down, and stood leaning against the counted, towering over me.

“I know, it really wasn’t my year,” I sighed, but he raised his eyebrows, so I added quickly, “I was trying my best, though.”

“Of course, you all are always trying your best, and then,” he slammed his hand on my desk, making me jump, before adding calmly, “Failing.”

“I…” I felt tears forming in my eyes and swallowed nervously, “I’m sorry, professor. Please, if you’d just assign me extracurricular work, I’ll do anything to pass.”

“Anything?” he raised his eyebrow and sat behind the counter.

I felt a shiver rolling down my back, this role play was by far my favourite one, I was really feeling it.

“Anything, sir,” I nodded eagerly.

“Are you wearing underwear?” he asked with a slight, yet nasty, smile. He looked like a hunter, who had cornered his prey.

I nodded, and he held out his hand, “That’s mine now.”

I took off my panties and gave it to him. 

“Now, sit on your desk and open your legs,” he ordered me, and when I assumed the position, he continued, “Wider, I want to see everything… A bit wider… Yes, that’s perfect. Suck on your fingers, pretend it’s a cock, you love sucking on them, don’t you?”

I nodded, gagging on my fingers.

“Good whore,” he praised me, before giving me new orders, “Now, start fingering yourself. But, keep the angle right, I want to see everything.”

I started slowly touching myself, and then slid one finger inside my pussy. I felt my fingertip brushing against my g-spot with every move, and I moaned quietly. My second finger joined in, and I felt my juices flowing out. I lose all control over myself, going faster and more rough. Somehow, I managed to get the third finger inside, still moving in and out. I was just about to come, but he raised his hand up, gesturing me to stop.

“Undress,” he told me and waited as I did so, then he handed me a marker, “Brand yourself, write on your pussy that you’re a whore.”

I had to congratulate him on his creativity, his idea might seem degrading, but in this BDSM role play, it was extremely arousing. 

It was difficult to write anything at that angle, but somehow I managed to write the whole word, it was barely readable, but it was here.

“Use the market to fuck your ass while you finger your pussy,” he spat another order at me.

I leaned back on the desk and spat on the marker, I needed something to lube it with, and saliva was the best I could come up with. I started moving it in a circular motion around my tight arsehole, it’s been a long time since I had anal sex with a client. After a while, I slowly pushed inside, fitting half of it inside. I didn’t feel any pain doing that, only more pleasure.

He handed me my panties, “Feed your hungry pussy, slut.”

I took the panties and pushed them inside me, leaving a bit outside to easily pull them out later.

“Good girl, now lie on your back and put your legs up.”

After I got in the position, the marker almost fell out, but he was there to stop it. He started fucking my arse with the markers and jerking off.

“Hold your legs,” he told me, taking off his pants, “And move more to the edge, I want to fuck your filthy mouth.”

Once again, I fulfilled his requests. Then, with everything in place, Todd slowly pushed his huge dick inside my mouth. Immediately, I started gagging, but he didn’t care, he didn’t even stop, only pushing more. He reached behind and pinched my nose shut, his right hand still fiddling with my arsehole. He started fucking my mouth, faster and faster, until he was close to orgasm. Then, he pulled away, satisfied. 

“Beg, slut,” he said in a low, heavy with arousal, tone.

“Please, let me go, sir,” I stuttered and coughed.

“No, no, that’s not what I meant,” he laughed again and grabbed my hair, pulling on it, “Beg for my cum.”

“Please, professor,” I tried again, “Feed me.”

“Good girl,” he said and pushed his cock inside my mouth, pinching my nose shut again.

After a few minutes, he pulled out, letting me breathe.

“Are you close?” he asked, taking out the marker, I nodded, and he continued, “What do you want?”

“I want to come,” I whined, wiggling my hips.

“All you need to do is beg,” he said and smiled mischievously.

“Please, sir, use my holes!” I pleaded, I forgot all about the role play, I only wanted an orgasm, “Please! Please, sir! Use me like a whore and let me come!”

“Yes, scream for me, slut!”

“Please, fuck me!” I screamed at the top of my lungs.

He walked around me and pushed his dick into my dripping pussy, holding the panties with his thumb, to make sure they won’t get pushed inside. He pounded my wet hole at a fast, yet steady, tempo, letting me cum over and over again over his thick member.

Then, he abruptly stopped and walked around again. My legs were shaking, I was so tired I barely knew who and where I was, but when I saw his dick looming over my face, I eagerly opened my mouth.

He laughed shortly and jerked off, soon cumming on my face, covering it all with his warm sperm. I swallowed as much as I could, enjoying the fruition of our hard work.

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