Anal Academy

Disclaimer: All characters are fictional and are above the age of 18 years…

When the email announced that I would be the lead violinist in the most prestigious musical set in the country, I knew I had to get on a call with a close friend of mine, Milo Carpenter. 

Milo was a once-in-a-lifetime talent who had retired from actively playing to being the conductor of his show at only thirty years of age. He was the violinist I consistently looked up to and the same man I had a crush on for years. He was tall, with beautiful dark locs, and he never had a clean shave. 

His rough-around-the-edges demeanour drew me in, and as fate would have it, our paths crossed when a mutual friend introduced us at my college's “artists hangout”. We were instantly drawn to each other and kept in touch. Although I initially thought it was weird that he chatted with me like I was his friend and equal, considering he was ten years older and I was only twenty at the time, there was never a dull moment.

It started off platonic, with Milo inviting me to artistic group events where we discovered we had so much in common; This led us to planning paired activities, with me eagerly looking for how to dress to impress him or stealing a glimpse of his features up close. Milo made my heart flutter, and I couldn't help talking to him about everything and nothing every day. 

Soon, our conversations became more intimate, and our chemistry was undeniable. Naturally, holding hands and pecks evolved into steamy romp sessions where I’d scream his name loudly from pleasure. I unabashedly spent several months in and out of his bed, where he plastered imprints of his body in my mind. It felt right, not only because he was all mine whenever he was around but I loved showing him off. Unfortunately, my joys were short-lived because Milo did not think entering a defined relationship was necessary. He had his reasons, mostly because he travelled so much and didn’t believe in long-distance relationships, so we left it at that.  

After calling to tell him the good news, we agreed to meet as usual whenever he was in town, and he even suggested mentoring my plays during those few weeks! The idea of it sent butterflies in my tummy all over again. 

Being the lead violinist would be no easy feat because it would require a chunk of my time travelling and attending practice. So, as soon as I got off the call, I began practising in solitude to ensure I warmed my body back into the rigours of the season while also secretly honing my skills to make sure Milo saw me at my best when we finally met. 

As the days drew closer to our meeting, my self-training became more focused on scales and etudes, but spending no more than four hours a day to prevent my fingers from wearing out. Yet, all the while, my mind kept getting distracted. Just the thought of hearing Milo’s deep baritone voice, or seeing his chiselled face, or taking in the warmth of his soft masculine lips again, ohhh… I spent days recovering from the sensual aftermath. He was always the one who seemed to know how to push all the right buttons all at once,  making my brain go mush. 

–

That fateful evening had arrived. I received a text early in the morning from Milo to an old concert hall that was recently being renovated and under his supervision (hence the reason for his trip back this time). The only thing he had instructed me to bring along was my violin, but knowing us, I was sure the night would end with more than just us exchanging musical notes. I wore my shortest maroon gown to amp up the mood. It had a deep V accentuating my fairly large braless breasts, and if I carelessly bent forward, it would ride up, exposing the under cheeks of my ass. I paired it with black tights and heels, making my long legs seem longer and sheer enough for him to see my beautiful red lace thong panties. I made no effort to cover myself with a coat, hoping when he saw my daring outfit, it would turn him on even more. 

When I arrived at the destination, I was greeted by the entrance door, which was locked. I quickly sighted a small latch where a letter was written with instructions on opening the door and a map to get to where Milo was. I chuckled slightly and guessed the evening would be a private event. 

I went to the back of the concert hall, where a reasonably large music room stood. As I looked around and admired the rather dim room, I was drawn to the centre, where the lights enamoured a chair. I turned to the far right and saw a silhouette - I knew it was him. As I made my way to him, albeit slowly, he sent me a text message on my phone and signalled for me to read it,

"You should be at the centre stage, lead violinist. Sit down and play." 

Is this a part of his first lesson as a mentor? I wondered while walking up on stage and finding my way to the seat. The chair was positioned on a podium at a rather high level, and with my outfit, positioning myself to play effectively would mean he would have the perfect view of what was between my legs from where he stood. And although he was encased in the shadows, I knew his eyes saw me struggle and squirm to be a bit more decent. That was when I heard the word "Play" echo loudly across the room. 

My heart started beating loudly for some reason, and frankly, I was beginning to feel a bit flustered. I’ve played the violin in front of Milo a thousand times before, but this was new and never with this much intensity. I quickly crossed my legs, picked up my violin case and brought out the instrument, taking as much time as possible to tune it as my mind raced.

"There's no time to waste when you're lead violinist Lydia. Play." His baritone voice broke through the shadows. 

I heard him take a few steps closer to me, and as he emerged, the dim lights in the room cast a shadow on his beautiful face. My heart skipped for a second, and swallowed hard as our eyes met. “Play” was all that kept ringing in my head. I steadied my breathing, took a deep breath and with my fingers on my violin, I positioned myself and began playing. 

I played my heart out to a classic piece from Tchaikovsky and slid in and out of rhythms flawlessly as practised. When my piece ended, I finally looked up in a daze. I had my eyes closed towards the end, lost in a trance of my own tunes, to find Milo right in front of me, staring at me stoically. He had breached the gap between us and stood about a foot away. His eyes were fixed on my outfit, causing my eyes to trace his, when I noticed my legs were astride and my gown had ridden up, bunching just before my crotch. I quickly crossed my legs and looked down at my violin.

"How well do you want to play?" He finally said after a few minutes.

"I want to be the best," I said quietly.  

"Just the best?" He asked again.

"Better than you," I smiled, giving him a slight smirk. 

"Really? Then you would not have worn that to a meeting we both knew would be a teaching session." He scoffed as he ran his fingers up my tights, causing shivers to run down my spine. 

"Did you go around town in this outfit? Without anything to cover up?" he whispered into my ear as I felt his hot breath against my neck. I clutched the violin and swallowed. 

"I thought you would like it. You said you wanted your women to be a bit more free." I said quietly, taking in his scent and wanting him closer. 

"That means you don't know me." He chuckled as his fingers continued to run down my thighs. "The first rule of being better than your mentor is to know him, and if you knew me, you'd know I don't like sluts.”

My brows contorted into a frown as I heard such derogatory words, but I knew my mind was fighting a lost cause when my crossed legs were now astride. Milo took the opportunity to stand between them. He gently raised his hands, brushed away my hair, and cupped my face while stroking my cheek. His warm lips fell on mine. He enveloped my upper lip, the lower one and returned to where he had started. I began to feel my panties get wet. He quickly grabbed the violin and returned it to its case. As he returned to kiss me, my hands began to stroke his taut muscular back, pulling him closer to me. Suddenly, he broke our kiss. 

“Are you ready to know me, Lydia? Are you ready to be the best?” He firmly but gently said.

“I am ready,” I said in a whisper.  

He smiled. “Close your eyes.” 

Obeying him, I felt him leave our embrace, but he soon returned as I felt a cool cloth, probably made of silk or satin, fall over my forehead and cover my eyes. I was about to say something when he pulled me back into his chest, squeezed my right breast and whispered into my ear, "Do not say anything." 

I became mute, relishing the baritone in his chest on my back. He placed his hands into mine and helped me down from the chair. 

"Follow my lead," he said. I had no idea where we were going, but he gently led me away from the light and into the shadows. With gentle nudges, he told me where to place my feet and halted me when we encountered an obstacle. It felt like a sensual dance. We finally stopped when he whispered, "We are here. Follow my instructions very carefully." 

I nodded, and before I could say anything, I felt myself being hoisted up by my ribcage with his firm grip. My legs instinctively wrapped around his torso, and my hands fell on his neck. I was a little surprised at how much I still trusted this man after all this time as he carried me effortlessly into the room. 

“Sit here for me.” He said as I felt his strong fingers trace down my ribcage into my waist and push me down gently onto a soft and wide padded seat that ran up the sides of my butt, it felt different. With one hand still holding my waist, he traced his fingers to mine and gently placed my hands onto a solid strap. As I grabbed onto them, it clicked in my head! 一 I knew I was undoubtedly on a swing as my feet were now airborne! This is new. 

As he pulled back slowly and left me alone, I found myself clinging on tightly to the solid hand straps and moving my hips around against the seat. That was when I felt a hard surface behind me that felt like what I assumed to be a large door. It held my position, and I adjusted myself to get more comfortable, with my gown slowly riding up even more, past my crotch and going midway up above my ass cheeks. 

“Lydia, I need you to know that I dislike mixing business with pleasure,” Milo whispered. 

“Why would you wear such slutty clothing and get me so hard?” He said in a hot breath as he kissed me again. 

I could feel his hands finally reach my pussy, and I held on the straps for dear life. I was sure that my juices had soaked through to the tights. His hands connected with my clit, and a throaty moan escaped my lips.  

I could feel Milo cup my face, and he kissed my moan away, only this time he took the blindfold too. When I met his eyes, I could see he was just as flushed as I was. His gaze was soft but fiery, letting me know whatever he would do to me would be solely for pleasure. 

“Are you a slut?” He said as his fingers reached my breasts and squeezed while rubbing my covered clit. 

“No, I'm not,” I whispered, thoroughly turned on. 

“Let’s find out.” He slightly chuckled. 

He kissed my forehead and left the room, returning with a pair of scissors. Before I could say anything, I felt the cold edge of its rounded-tip blade against my skin. He never broke eye contact and kept giving my lips airy kisses as he ripped away my dress, tights and panties, leaving me in tatters. My body relished the feeling as my clit jerked from the cool breeze, and my nipples stood at attention. 

He moaned in my ear as he sighted my naked body and leaned in to kiss me again, this time more fervently. 

“Since you have decided to look like a slut, I will fuck you like one.” He finally moaned in my ear and stepped away from me. 

Milo picked me up easily from the swing with one swift move, placing my feet gently on the floor. I wasn’t even aware I had lost my shoes in our rendezvous until my feet had touched the ground. Slowly, he spun me around, and his hands guided my back to his chest. Gently, he peeled off the rags from my body and, with his fingers, made gentle circles around my shoulders and upper back, kissing my nape and tracing it down my spine, making me shiver from pleasure. 

Taking the swing seat and bringing it over my head towards my chest, Milo positioned it against the bottom of my bosom. Unsure of what he had planned, I stiffened, but he allayed all fears when he brushed my hair softly behind my right ear and with a hot whisper, he mouthed one word, “Relax,” causing my body to soften instantly. Leaning me forward with one broad palm resting against my back and another against my left hip, Milo instructed, “Hold onto these straps and bend over for me,” causing me to obey immediately. With the seat positioned comfortably below my chest as I looked down towards the ground, I found that I was in an almost standing doggie position, yearning for his next anticipation. 

As he gently leaned me over, my legs parted with my ass right before him. I could feel his hardness as I pushed back against him, hungry for more attention, but he knew how to tease me and kept pushing me away. Soon, I felt something slippery on his hands as he grabbed my ass cheeks firmly, causing me to match his ragged breathing as he massaged them in between squeezes.

Decisively, his fingers reached the engorged lips of my pink slit, which was now saturated with the heavy flow of my warm juices. The combination of pain, pleasure and nasty words created a cocktail of moistness, and Milo knew just how to make me coo as he circled around my nub, playing with varying pressures and intensity. 

A loud moan escaped my lips as he pushed me further into the seat and hoisted my ass higher. He tactfully dragged his finger upward along the valley between my ass cheeks. I felt him bend, and I could swear he was looking at my ass hole. I wondered if he enjoyed watching the pulsating motion of it. My question was answered when he circled the rim with the pad of his thumb and gave my entrance a light push.

“Fuuuccckkk,” I yelled. With each circular motion, Milo could see me shiver. They grew more profound when he simultaneously slid his fingers against my flushed slit and back up to my cheeks.

"Look at you, groaning under my strokes like the little slut you are,” Milo laughed, applying more pressure with his finger against my hole. He then traced his other fingers to explore the opening of my pussy. 

"I’m your little slut”, I belted out, unsure where that had come from, but he seemed pleased because he pushed his full finger length deeper into my ass hole and pussy and whisked them out of me with one quick pull. I jerked up in pleasure.

Using both hands, Milo pulled my ass cheeks apart as he leaned down to lick up all the juices from my pussy entrance to the rim of my hole. He took his time and licked all my crevices like he was entitled to them. I knew he could feel my breathing get harsher, and he knew I was close to cumming when he lay a wet, smacking kiss on my rim before rising to his full height.

Milo then pushed his finger into my ass hole and slapped my ass repeatedly with his free hand. 

"What the fuck are you doing to me, Lydia?" He asked in grunts. 

I moaned in ambiguous syllables as Milo slid his levelled digits in and out of me. He swatted an ass cheek again, and I was sure pale handprints would be left behind.

"I can’t seem to get enough of you.”  He said in a low tone. 

Pulling his wet fingers from my love hole, I felt him part my ass cheeks again and dribble more slippery substance into me. He used as much of it to prime me and then said smoothly, “Are you ready for your finale?” 

I nodded almost comically as he placed all three fingers and a fourth into me while another hand expertly rubbed my clit simultaneously. The sensation of being stretched out in my love hole caused my eyes to roll to the back of my head, and that was when I felt my orgasm rising! My body shivered even more as he thrust and rubbed against me faster and faster, matching each breath. Once again, I gripped down hard against the hand straps and cried,  “Oh god, oh god! I’m cumming!” Without a moment’s notice, I came, quivering hard, thankful that Milo held onto my hips as my knees caved in.

Resting my body weight against the soaked-up swing seat and catching my breath, I heard Milo chuckle as my juices trickled out of me, planting kisses of praise on my ass cheeks and lower back. 

“Welcome to your first lesson, lead violinist,” Milo said softly. 

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