Lesson Two: Pain

Sometimes it is harder to deprive oneself of a pain than of a pleasure — F. Scott Fitzgerald

The memory of my first encounter with Jacob weighed heavily on my mind.

Anticipating my next lesson left me restless. I was still agitated by the state I had been left in after the first encounter and the way he had nodded politely, as though bringing a casual conversation to an end, before quietly excusing himself to meet his next appointment. He had left me without any regard to the silver vibrator still neatly tucked inside of me.

I remember the moments it had taken for me to collect myself. Unnerved as I rose from the table, my clumsiness betraying me to suspecting onlookers. By the time I had reached my Rideshare, the presence of the vibrator had been impossible to ignore. Sitting in the back of the car, every bump and turn that slightly shifted my body left an agonizing, undeniable need to come that I had felt with every fibre in my body.

The day of our next appointment had finally arrived. Slipping my black lace panties up under my skirt in preparation, I glanced at the silver vibrator sitting on my nightstand. My eyes had wandered to it longingly over the last week and I had valiantly fought the urge to use it. I wondered if Jacob would finish what he started. I wondered if I should bring it with me. I had wondered many things over the last few days, feeling the suspense of what was to come. Would it be me?

I walked the cafe, ready for the days lesson. Jacob sat waiting with a book in his hand. Perfectly composed and poised, the picture of elegance. His blond hair was tied back revealing the shaved sides. My insides did a backflip at the sight of him, making me me moan under my breath. Jacob’s eyes met mine as I approached.

Rising he leaned in and kissed my cheek, “hello darling, are you ready for your second lesson?”

I nodded, inhaling the sweet scent of him. Taking my elbow, he lead me out of the cafe to a waiting car.

“Where are we going?” I asked confused. Nudging me along, he smiled, “Today’s lesson does not involve questions.”

As we rode in silence, I scanned my surroundings for anything I might recognize for a hint of our destination but found nothing familiar. After a drive of 10 or so minutes we turned onto an industrial road and the driver stopped in front of a gray stone building with towering double doors. The number read 365.

Jacob slipped his hand in mine as he lead me out and I decided then and there that I would willingly, and happily embark on any adventure with this man.

We walked through the doors, they appeared to be heavy and cumbersome but Jacob handled them as though they were designed specifically for him. The vast gothic structure imposed power and beauty with its vaulted ceiling and light, airy interior. If it weren’t for Jacob pulling me along, I would have surely stayed and admired its beauty indefinitely.

Crossing the marble floor, we approached a reception desk. At its center sat a perky brunette with the greenest eyes I had ever seen. She was dressed elegantly, in a dress that hugged her body in ways that left little to the imagination.

“Hi Jacob.” She winked and smiled beautifully as we walked passed. She eyed him hungrily as we passed but never straying from the task at hand; Jacob lead me to an elevator and the doors opened for us on cue.

Within seconds of stepping in the elevator, his beautiful face appeared three inches from my own, his hands were placed on either of the wall behind my head. “Ask me!” He whispered in my ear. I looked at him blushing, remembering the brunette we had just passed but responding defiantly. “Ask you what?” His body pressed into mine and I began feeling the heat rise inside me. “Ask me if I fucked her.” I could feel his arousal growing against my leg and it took all I had not to reach down and press my hand against him.

The elevator door opened, and Jacob pulled back. Regaining composure, he took my arm and lead me out into a long concrete corridor. Next we entered a loft space that had been converted into an stunning office space. The windows were enormous, letting in a breathtaking amount of natural light. A mahogany desk sat in the center of the room. It was neat and clear of objects save for a laptop and a few open books. He had a large bookcase off to the right that held a selection of old typewriters. I imagined they had taken the home that had once belonged to all of the written volumes that currently lay scattered across every other surface in the vast room.

Standing in place, I took it all in. I could feel Jacob’s steady gaze as he deftly poured two glasses of whiskey for us. “Did you touch yourself?” Meeting his eyes, I shook my head no.

He looked at me with approval and handed me the glass. Swirling the amber liquid, I inhaled the sweet smell of Jameson. Bringing the glass to my lips, letting the liquid fill my mouth, I held it for a few seconds enjoying the slow burning sensation on my tongue before letting it slide down my throat. Jacob watched me curiously, as he rubbed his lower lip with his thumb. “How do you feel about physical pain?”

I took a moment to think, then. I knew I could take a significant amount of pain, I was very resilient, however I was unsure of how I wanted to answer his question given the context of our meeting and my lack of experience at this level. As usual, the look in my eyes must have given me away because rather than wait for an answer he beckoned me forward to the couch. I stood before him as he sat and delicately slid his hand under my skirt. His fingers slid over my thigh and up the curve of my ass and I enjoyed watching as he closed his eyes in silent appreciation. Using his free hand he brought me down and bent me over his leg.

“Is this ok, Taryn?” My heart raced as I nodded. My body tensed as he caressed my ass and I prepared for what was to come. The fist blow surprised me, its force causing me to flinch. Running his hand between my legs, he suddenly stopped, making me smirk. “Taryn is the vibrator inside you?” I didn’t respond, trying to stifle a defiant giggle. Jacob slapped my ass several more times, increasing the force behind each blow with the intent to punish. “I did not instruct you to insert it for this lesson.” Lifting me from his lap, he placed me on my knees between his legs.

“Remove it!” He ordered grabbing hold of my shoulders. Feeling scolded, I spread my legs apart and did as I was told. The bullet was wet between my fingers as I placed it on the table behind me. Wrapping his fingers around my neck, lightly but securely, Jacob’s eyes peered into me as he reminded me “In Lesson One, we learned that I make the rules and you must comply. You must comply, Taryn!”

He let go of me and I immediately stood, needing a moment to collect myself. I walked across the room sipping the whiskey slowly to cover my frustration. I felt childish, why couldn’t I just do what I was told? Why did I always have to make my own rules?

Lost in thought, I didn’t see the book on the ground. I tripped and the glass slipped from my hand shattering around my feet. I dropped to the ground without thinking and began picking up the broken shards, slicing my palm as I did so. Everything happened so quickly, and I cried out in pain. Jacob was at my side then, whisking me off the ground and sitting me on his desk. The cut was deep, and blood seemed to be everywhere. “Don’t move.” He left but returned swiftly from the kitchenette with a clean towel and a bottle of alcohol. Within seconds he was pouring the alcohol over my hand and I gritted my teeth to hold back a cry. Jacob grabbed my chin, “Stop, Taryn. Focus. Endure the pain, feel it. You control it, it does not control you.”

Slowing my breath, I forced myself to focus before looking up at him again. I was sitting on the edge of the desk and Jacob pulled me suddenly forward towards him. I immediately wrapped my legs around him in response and felt a ripple of excitement course through my body. I was confused by the pain searing through my hand and the desire that flared back up – the need to have him penetrate me. Jacob leaned in and began kissing me. I shivered as he slipped his tongue in my mouth, making me wrap my legs around him tighter. He allowed me a moment to indulge and then stopped me, taking my hand in his. He wrapped it in the towel, making me cry out as he applied pressure. “Control it, Taryn!” Continuing to apply pressure, he took my free hand with his and pressed it to his bulging erection. I could feel it throbbing under my hand, making me forget the pain in my other. I stroked the length of it, appreciating what I could feel through his jeans. He pressed his lips once more to mine, making me moan loudly and tighten my grip on his cock. Locked in a moment between pain and pleasure, I was filled with the desperate need to come.

“Please, Jacob!” I begged, “make me come.” Sliding his hand inside my panties, I felt his thumb graze me. My hips bucked forward urging him to continue, to press harder. As if to indulge me, he slid the tip of his index finger inside me followed by another, then another. I pressed my head into his shoulder and whimpered as he left his fingers just barely inside me, perfectly still. Resting in place. I needed him to go deeper, I wanted to feel him push in and slide out. I wanted to come and in that moment, I would have done anything for the release.

“Taryn, do you want to come?” I looked straight at him, “Yes, Jacob, can I please have your permission to come?” For a split second he hesitated, then pulled his fingers out to my absolutely dismay. “No, Taryn. You were a bad girl. You will not come today.” I sat there stunned as he took a step back.

“It is time to get you cleaned up. We shall resume our lesson next week.”

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