Teach Me Ch. 02

The weekend flew by, filled with tons of masturbating. I got so bored with the same masturbation techniques, I started to edge myself. Making myself wait longer and longer to come until I exploded in ecstasy. I imagined someone fucking me senseless, a strange man I had never met. It made me feel dirty afterwards, so I would shake the thoughts, but later they would come back like a train running through my mind.

Jeni hadn't texted me and I hadn't texted her either. I didn't want her to know I was planning on going. I didn't want any more details, I just wanted it to be a surprise. No more talking myself out it.

Sunday night, I was riding my dildo suctioned to the headboard of my bed. I backed up over and over, impaling myself on it. My phone chimed and I ignored it. I rubbed my sensitive little clit and squeezed it in between my fingers, shocking myself. It was taking so long to come; I almost gave up. An image of a tall, muscular strange man I had never met before sliding his cock in and out of my hot pussy, and I exploded. I came hard, pushing the dildo in and out of my pussy still to draw out my orgasm. Once it had subsided, I collapsed into my bed and fell asleep after a little while.

I woke up to my alarm at 7:30 and rolled out of bed groggily. I remembered what I was doing suddenly and was wide awake. My stomach roiled and I felt slightly nauseous. I showered, meticulously getting ready for my 'appointment.'

Once ready, I headed out the door and drove downtown to the address Jeni had provided me. I brought identification just in case I needed it and also left a note on the counter with the address. You know, just in case I was kidnapped and murdered.

The drive was peaceful, but I was full of anxiety. I chewed my lower lip, humming some song on the radio playing in the background. I got a lost once and was thankful I had left early. Finally, I pulled into an oversized parking lot. I found a space after some time and sat in my car for a few minutes, contemplating. I almost turned the ignition back on and drove right home. But I didn't. I forced myself out of the car and across the lot.

I got to the door and reached out, hand shaking. I steadied myself, gripping the handle, taking a deep breath. I swung it open and walked through the foyer with an air of confidence I didn't really feel. Fake it until you make it Cas.

I reached the front desk sitting in the middle of a large and open lobby. Everything was immaculate, in its place. The woman behind the desk was gorgeous and I felt myself fidget with insecurity. I looked up coyly and asked the woman what floor the suite number I was looking for was on.

"Sixth floor," she answered in a curt but pleasant voice.

I nodded and thanked her, walking to the elevators. Once inside, I let out a whooshing breath and leaned my head against the elevator wall. Fuck, I hope I'm doing the right thing.

I reached the sixth floor, and walked out into a long corridor with doors on either side. I walked slowly, trying to collect myself. Upon reaching the door, I was breathing steadily but my heartbeat was a wild bird caught in my chest. Beating, beating, beating to get out.

I raised my hand to knock and the door opened before I could even touch it.

"Oh-"

"I'm sorry, didn't mean to scare you." A deep mellow voice drawled in a slight southern accent. I looked up and up into the dark eyes of the most handsome man I had ever laid eyes upon. I blushed deeply, looking down to hide it. He chuckled and my head snapped up, eyes narrowed.

"What's so funny?" I asked with an attitude.

"Nothing, nothing at all. Would you like to come in? You're right on time. I was waiting." He wore a smirk on his face, and I could already tell he was a jackass. One of those tool bags that knew they were hot and flaunted it. Relished in it.

I pursed my lips and made a sound of disapproval but followed him inside. He was wearing blue jeans and a white t-shirt. Bare feet. He was tanned and toned. Dark hair, dark eyes. I was mesmerized by his looks, but I was sure I wouldn't like him as a person.

"Would you like something to drink?" At least he was a good host.

I shrugged. "Sure." I was unamused already by this entire experience and regretted even coming. I just have to make some excuse to leave.

He handed me a glass of water and directed me to sit on one of the black leather couches in his living room. I expected it to be an office, but it was more like an entire apartment. I felt a little more comfortable as I sat down and looked at my surroundings. He had good taste. Rustic décor that gave the place a homey kind of feel.

"So, it's Cassy, right?" He sipped his own water, sitting on the couch across from mine.

"Mhm." I nodded, setting my glass down in the side table next to me.

He nodded as well and set his glass down, mirroring me. There was an awkward silence for a minute or so, when I just had to break it. I looked up to him staring at me with that smirk on his face.

"Um, so what is this all about?"

He raised an eyebrow. "You don't know? Why are you here? Let's start with that."

"I asked first."

"Oh, so you like to play games, do you?" He raised his eyebrow again, full on smiling.

"Maybe."

"Well, this is basically a program for people who are.... not very talented at sex. I'm a teacher, I teach you how to fuck and we have fun during the process. Some people need a month, others need six, it just all depends. No names, no connections or relationships. It strictly business."

"It that all? You seem to have that rehearsed."

"That's the gist of it. Today's screening shows me what you need assistance with and what you don't."

"And what does todays screening consist of?"

"Oh, I let you fuck me," he said matter-of-factly.

I gawked at him, totally caught off guard. "Me fuck you?"

"Ouch, don't hurt my pride or anything." He put his hand to his chest.

"Oh, please. You know you're gorgeous." I rolled my eyes to the ceiling.

"You think I'm gorgeous?" He feigned sincerity and I almost vomited. "No, really. You do?" He looked serious now, head cocked to the side.

"Well, yeah, look at you." I scoffed, waving my hand at him.

He looked ot be in deep thought for a moment and then shook himself. "Well, thank you. That means a lot."

"I just meant that you want me to do all the work? On the first appointment?" I wondered out loud.

"Well, yeah. How else would I know what you need help with?"

I thought about that for a minute, chewing my lower lip. When I looked up, he was watching me.

"Shall we?" He stood, holding his hand out for me to take and I tentatively took it, standing.

He led me to his bedroom, which was elaborately decorated, it was dark with dim lighting. The four-poster bed has black silk sheets and looked like a bed fit for a princess. He led me to the bed and pushed me down on it.

He bent to take my shoes off and I let him. He placed them across the room and walked back slowly, looking me all up and down. There was lust in his eyes, and I blushed.

"Does the rest of you turn red too?" he looked down towards my sex and I blushed deeper.

"I guess you'll find out," I managed to get out with a false air of confidence.

He snickered and reached up to unbuckle my jeans. I put a hand on his shoulder. "I can get undressed myself."

"Of course, but what kind of gentleman would that make me?" He cocked his head, I bit my lip, he watched this and as he did, his nostrils flared out as if he was having trouble getting enough air. He looked away from me and I stood to make it easier for him to shimmy my pants down my legs. His face was right next to my sex, which was throbbing painfully now and dripping wet. He wasn't as bad of an asshole as I initially thought, but he was still somewhat cocky.

This was insane, letting a stranger pull off my pants, not to mention having sex with said stranger on the first 'date.' I had never done anything like this before. But I couldn't help the thoughts swirling in my head, the things I thought of while masturbating all weekend. A perfect stranger taking care of me sexually. And here he was.

I sat back down once he had my pants off, folding them neatly and setting them on a chair across the room next to my shoes. He lifted a brow and motioned for me to stand back up.

"My panties too?" I reddened.

He didn't say a word, just kneeled on the floor before me, waiting. I sighed and stood back up, letting him hook his thick fingers in the hem of my panties and pull them down slowly. They brushed gently down my legs like a whisper.

He stood and lifted my arms, taking my shirt and bra off in one swift motion. I gasped and went to cover my nakedness before he could see. He caught my wrists and held them, taking me in, his gaze sweeping up and down my bare body. I looked away, biting my lip. He let go of my wrist and caressed my cheek, turning my face towards his.

"My turn to bite that lip," he whispered gruffly.

He moved in closer and took my lips between his perfect pearly teeth, squeezing ever so gently. I moaned quietly into his mouth at the gesture. He let go and backed his face away, looking intently into my eyes, shaking his head. His dark wavy hair fell into his eyes and he brushed it out of his face, sighing.

"This isn't how this is supposed to go. You're supposed to do all the work. But I just wanted to see what makes you tick. You liked that, didn't you?" He was still caressing my cheek.

"I didn't know I liked that, but yes," I breathed.

"Do you like pain?" His eyes flashed in excitement I thought.

"I'm not sure," I lied.

"You're making this very difficult for me, you know that?" He didn't look angry, but more so concerned.

"I am? Oh, whatever. You just bit my damn lip," I exclaimed.

He answered by spinning me around so that I was facing the bed and he laid down in front of me, taking his clothes off.

"Oh, I can help with that."

"Yeah? Go ahead." He swept his hand his hand over his body, looking amused.

I pulled off his jeans and shirt and folded them neatly liked he had. But I had no idea what to do next. It had been well over a year since I'd had sex last. And the few times I had had sex, it was pretty awful. The guys had always taken charge and it was always so fast, I didn't even have time to react. This time would be different, I would show him I wasn't a complete rookie.

I got up on the high bed awkwardly, straddling him even more awkwardly. So much for being sexy. He grunted as I got myself in the correct position, leaning on his torso for support. He wasn't kidding when he said I'd have to do all the work.

I stayed there for a minute, covering my boobs with my hands and feeling embarrassed. He took my hands from my chest and guided them down to his. "You can touch me, you know."

"O-okay," I stammered.

He laughed, "I won't bite, I promise."

I moved my hands over his firm, muscular chest, feeling his pecks and abs. He had a god-like body, it was beautiful. I kept feeling his chest, when I felt his hand nudge the small of my back, guiding me lower onto him. I allowed it and slowly bent over him, until my lips touched his chest. I opened my mouth and licked once. I surprised myself by the act of it. I trailed my lips up his torso, licking here and there, tasting.

I stopped when I got to his neck. I froze completely, unaware and trepidatious to do what I thought I should next. I lifted my head slightly and looked at his mouth, there was no smirk this time. His lips were parted slightly, he was panting. I took it as a good sign and lowered to kiss his full lips. He welcomed my mouth to his in a wet embrace. If sparks could fly in that moment, they would have.

We kissed for a few minutes, both of us panting, chests heaving. I lowered my head and bit his neck, which elicited a gasp and moan from him. Suddenly I realized something and stopped abruptly. I raised my head and asked, "What's your name?"

He laughed heartily before answering, "Mathew. But you can call me Mat. Now please, continue," he commanded, I obeyed.

I lowered my head again and bit at his neck, a bit gentler this time. He seemed to like that the first time. He gasped and made sounds of approval deep in his throat. It made me wet, and I was already soaking and throbbing. I couldn't take anymore, so I raised my hips and lowered by ass onto his dick, just to get a feel for where I needed to aim. I lifted my hips and reached under me with one hand to guide him inside me.

He entered me with an audible pop. I sucked in air and hissed through my teeth. He was big, and I was unaccustomed. I let myself adjust for a minute before lowering further onto his member. He stretched me wide, and my walls were crammed. I had no idea what to do next, so I just bobbed up and down shallowly on his cock, it was starting to make me shudder in pleasure. It was the best sex had ever felt. I moaned and threw my head back so I wouldn't have to make eye contact with him.

Suddenly, he grabbed my waist and twisted me off him. He laid me on my back on the bed and pummeled me. He shoved his thick cock deep inside of me to the hilt and I cried out.

"You can take it can't you, good girl?" he soothed, smoothing my hair back from my face. "Look at me while I fuck you," he demanded.

I looked into his eyes and cried out again at the sight of them. He looked almost like he was straining, the cords standing out on his neck. I reached up to put my hand on his chest, he grabbed both my wrists and pinned them above my head. He kept pounding into me until I felt something strange, like a warmth spreading through me. It exploded and I saw white. It rushed through me from my pussy and out through my limbs.

"Fuck!" I cried out. "Oh my God!"

He smiled and pounded into me even harder, drawing out my first orgasm from a man. I was relishing in it, throwing my head side to side and practically screaming. He slowed a bit when I had finished, grunting. He slid out of me gently and twisted me around again so that I was bent over the bed. He got off and pulled my legs across the bed, so that my ass was perked up in the air for him.

"I love your ass, I wish I could fuck it," he moaned.

"I'm not ready for that," I said with wide eyes.

He laughed, "Another time then."

I shivered at his words and his touch along my spine. He slid back into me and reached under my belly to play with my sensitive little nub. He twisted it between his fingers and pinched and pulled gently. I was gasping and moaning like a wild woman by the time I came again. This time, he came with me. He spurted inside of me, filling me up. Fuck, I'm not on the pill.

He pulled out of me with a wet squelchy sound and pulled me to him, turning me around. "That was phenomenal," he whispered against my hair.

"Will the cum stay in me or should I pee?" I asked naively.

He belly laughed at this, "That's what you're thinking about after that amazing round?"

"Well, sorry, I didn't know," I retorted angrily.

"Go to the bathroom and clean yourself up and meet me back out in the living room. We have much to discuss."

So, I headed to the bathroom and cleaned up, peeing and wiping myself fresh. I stopped in his bedroom first to get dressed and met him out in the living room. He was still naked.

"You put those back on for me to take off, huh?" I gawked at him.