"Alright, Max," I said on the Teams call, "I shall be very happy to tutor you, but before we start, I need you to write a story, any story. Something you enjoy and are good at, and it doesn't matter what the subject material is. Once I have the story, I will be able to gauge how much support you need."
"Thanks, Mr. Jenkins, I appreciate your time, and I know my mum will be very happy, especially with the tuition fee you have suggested."
"You are most welcome, Max, and hopefully, we will get your grades up to where they should be. I suggest you email the story when ready, and then we can get together for our first session. Sessions, by the way, are face-to-face because it's more effective than on Teams."
"I get that, and thanks for being flexible, Mr. Jenkins."
"Alright then, I shall wait to hear from you. Bye for now."
"Bye, and thanks, Mr. Jenkins. I won't let you down." Max's response was enthusiastic, not entirely a common response, considering most pupils I tutored begrudged extra lessons outside of school time. In the interim, I had time to ponder what Max's writing skills would be like as an 18-year-old young man, and as it transpired, I didn't have to ponder long.
The next day, Max sent an email with his story attached. The subject line read 'Story for Mr. Jenkins,' and my curiosity piqued as I clicked on the email. The attachment was a simple Word document titled 'My Tighty Whities Adventure'. The title made me chuckle, and I couldn't help but wonder what kind of tale Max had conjured up. I took a sip of my morning coffee, the aroma of the dark roast wafting through the air and settled down at my desk.
I opened the document, expecting a short story with a few paragraphs at most, but to my surprise, it was a full-blown epic. The story began with a description of a mundane morning routine that quickly took a whimsical twist. Max's protagonist, a pair of white Hanes briefs named Timmy, came to life most unexpectedly. It was a refreshing and imaginative take on a seemingly ordinary object. As I read through the pages, I found myself drawn into Timmy's adventure, smiling at the playful humour and the sheer creativity behind the storyline.
But as the story progressed, the tone began to shift. The lines between reality and fantasy blurred, and the plot grew increasingly sensual. Timmy, the animated undergarment, found himself in situations that were more suited for a young adult novel than a simple homework assignment. Max's writing grew more vivid, his sentences painting a picture of a world where the most intimate of garments had feelings and desires. The vividness of the scenes grew more intense, and I could feel my cheeks flushing slightly as I read.
The climax of the story came when Timmy, feeling the warmth of the sun on his cotton fabric and the gentle breeze caressing his waistband, decided that he never wanted to be confined again. He begged Max to let him stay in his briefs form forever, frolicking in the meadow where they had shared so many adventures. Max, torn between his loyalty to Timmy and the practicality of the situation, tried to reason with his underwear. He described the comfort and freedom of feeling the air on his bare skin, the joy of their shared experiences, and the thrill of being seen by others in such a state of innocent vulnerability.
As I reached the end of the story, I couldn't ignore the tension in my briefs. Max's writing had an unintentional effect on me, and I found myself aroused by the sheer audacity of the narrative. It was clear that Max had a natural gift for writing, but the content was not suitable for our English tutoring sessions. I closed the document, feeling very flushed, and decided that this was a conversation that needed to be had in person. The line between student and teacher blurred for a moment, and I wondered if I was crossing a boundary by being so affected by his story. But I knew it was important to address the inappropriateness of the subject matter before we moved forward.
I composed an email to Max, keeping my language professional and neutral. "Thank you for sharing your story with me, Max. You have a strong creative streak and excellent writing skills. However, the content of 'My Tighty Whities Adventure' is quite mature for the context of our English lessons. For our sessions, I would like to focus on more academic and age-appropriate topics. I look forward to meeting you in person for our first session tomorrow. Please arrive at 3 PM sharp." I hit send and leaned back in my chair, hoping that my cheeks weren't still red.
The next day, Max arrived on time with an infectious cheerfulness. His eyes twinkled with excitement as he stepped into my study, the aroma of freshly cut grass and a hint of youthful sweat following him in. The room was a sanctuary of books and knowledge, with shelves groaning under the weight of classics and textbooks, a stark contrast to the whimsical tale Max had crafted and I had printed out with a view to being critical and rubbishing the whole story.
"Tell me, Max, why did you write such an unusual story?" I asked as he stood there in front of me.
"That's simple, Mr. Jenkins. I like Hanes briefs, or as you old timers would say, tighty whities. It's funny, I know, no one calls them tighty whities anymore and probably haven’t in thirty years, but I decided to use the nickname anyway."
"I see," I said, trying to keep a straight face. "And the... er... undertones? Why do you like Hanes briefs so much to the point you write a story about them?"
"That's simple, Mr. Jenkins, and then he waded into a short lecture about the benefits of Hanes underwear. "Hanes white tighty whities, or men's briefs, are classic, full-cut design made from soft, pre-shrunk cotton. They feature a soft waistband that is designed to be plush and provide all-day comfort. The briefs also have a functional fly and no ride-up leg bands, which are guaranteed to stay in place. They also look fabulous on men. Much better than those boring boxer briefs."
I nodded, trying to keep my thoughts in check as he spoke so passionately about something so... unexpected. It was clear that Max had a unique perspective on life, and his writing reflected that. I couldn't help but feel a bit shocked, yet strangely intrigued. Here was a student, barely an adult, sharing such an intimate and unconventional interest with his tutor. It was a moment that was both awkward and fascinating.
"Do you wear traditional underwear?" Max asked me. "My father used to, but he's moved to boxer shorts, and I hate seeing him wear them. They're so boring."
I cleared my throat, trying to steer the conversation back to a more academic footing. "Well, Max, while your enthusiasm for the subject is commendable, I think we should focus on writing topics that are more suitable for our tutoring sessions."
"Why? Mr. Jenkins. What's wrong with discussing underwear as a writing subject, and by the way, you still haven't answered my question. Do you wear traditional underwear?"
Max's question hung in the air, and for a moment, I was at a loss for words. This was certainly not the direction I had anticipated our first meeting to take. But then, I recalled my duty as a teacher to guide and encourage, not to stifle creativity.
"Max," I began, choosing my words carefully, "while your story is certainly imaginative, the content is quite... personal. For our tutoring sessions, we should stick to topics that are more universally relatable and appropriate for academic study."
"But Mr. Jenkins," Max protested, his eyes sparkling with a hint of defiance, "why should my interests be dismissed just because they're not 'normal'? I've been writing erotic fiction for three years now, and I've got a following on the internet. It's a form of art, just like Shakespeare's sonnets or Tolstoy's love scenes, but no one bats an eye at those."
I took a deep breath, trying to maintain my composure. "Max, I understand where you're coming from, but the material you've shared is not suitable for our tutoring sessions. We need to focus on improving your comprehension and writing skills within the confines of the school curriculum."
"Please, Mr. Jenkins, can I show you because it will provide you with more insight about my ability. I can write normal shit, but I love to write......different scenarios."
I realised that Max was not going to give up on the subject, and I could see and feel his passion. "Very well, show me and then perhaps we can move on."
Max quickly walked around to my side of the desk and took control of my laptop, his fingers dancing across the keyboard. Within moments, he had pulled up a website called 'GayDemon'. The screen filled with a vibrant array of images and stories that were not what I had expected from a high school student.
Max's face flushed with excitement as he scrolled through the various authors until he came to his name.
"Here it is, Mr. Jenkins," he said, clicking on his profile. The screen filled with a list of story titles that ranged from "The Enchanted Briefs" to "Underwear Uprising". The genre of each tale was marked as 'M/M Erotica'.
Taking control of the mousepad, I opened a couple of stories that Max recommended, bracing myself for what I was about to read. The first one, titled "A Whisper of Silk," began with a poetic description of the fabric against bare skin, the sensuality of the scene palpable. Max's writing style was indeed quite sophisticated, and I couldn't deny the allure of his prose. His command of language and ability to evoke sensuality were beyond his years.
"I see," I managed to say, trying to keep my voice steady. "These are... quite... vivid."
"I know," Max replied. "Capturing the descriptive is always hard, but it's become much easier recently using my personal experiences as a guide."
"Ah, I see," I said, trying to keep my tone neutral. "Your storytelling has a... a distinct flavour to it."
"Thanks, Mr. Jenkins," Max beamed. "I do enjoy it."
I closed the laptop lid, cutting off the explicit imagery on the screen. "Why don't you write a story for me now and show me what you can do?" I suggested, hoping to redirect our conversation to a more suitable topic.
"Right, Max thought about now?" Max asked.
I thought for a moment, trying to come up with a topic that would challenge him but also keep within the bounds of our tutor-student relationship. "How about you write a short story about a pair of underwear that gains sentience during a laundry cycle?" I suggested, trying to keep my voice even.
Max's eyes lit up at the challenge. "Oh, that's brilliant, Mr. Jenkins!" He quickly positioned his laptop on the polished mahogany table and began to type. His fingers flew over the keys as he spun a tale of 'Randy the Reckless Briefs', a pair of underwear that comes to life in a world of socks, towels, and other garments. I watched him, fascinated by his ability to weave such a vivid and engaging narrative on the spot.
Without warning, he started to unbutton his shirt. "What are you doing?" I asked, my voice catching slightly in my throat.
Max looked up from the table, a mischievous smile playing on his lips. "You said I should write a story, but I can't write properly when I'm all dressed up. It's like the fabric is... stifling my thoughts."
I couldn't help but watch as Max shed his shirt, revealing a toned torso that made my heart skip a beat. He was more than just a student in need of tutoring; he was an enigma wrapped in a teenage body. His confidence was intoxicating, and his willingness to bare himself so openly was both thrilling and disconcerting as he slipped his shorts down, only to step out of them, leaving them as teenagers would, crumpled on the floor.
Max returned to the table in nothing but a pair of those infamous white Hanes briefs, his new story already unfolding in my mind's eye. His body was a canvas of youthful vigour, the contours of his muscles speaking of countless hours spent in the sun, playing sports and exploring the boundaries of his sexuality. The fabric of his underwear clung to him like a second skin, hinting at the treasure that lay beneath.
As he wrote, the room grew warmer, not just from the summer heat but from the tension between us. His fingers danced over the keyboard, his eyes focused on the screen as he crafted his tale. I tried to concentrate on the words he spoke, as he verbally described the story he was weaving, but my gaze kept drifting to the growing bulge in his briefs, evidence of his arousal. It was a stark reminder of the power of words to evoke passion, even in the most innocuous of settings.
I shifted in my chair, trying to discreetly adjust myself as my underwear grew tight. My thoughts were a jumble of confusion and desire, the line between student and teacher blurring with each passing moment. The fabric of my trousers felt rough against my skin, a stark contrast to the softness Max had described so eloquently in his story. The ache grew stronger, a pulsing throb that I could no longer ignore.
I was absorbed in my thoughts when Max declared, "Finished."
He turned the laptop to face me, revealing his new creation. "Randy's Awakening" was a whimsical tale of a pair of underwear that comes alive during a laundry cycle, exploring the domestic world with childlike curiosity. The story was devoid of the explicit content from his previous work, but still held the charm and vividness of his writing style.
Max stood up, his erection visible through the fabric of his Hanes briefs. The damp patch at the front grew by the second as he stood hovering, his excitement for his new story evident. The room felt charged, the tension between us thick enough to cut with a knife. The creativity in his eyes had transformed into something more primal and raw.
"Wow," I murmured, taking a deep breath to steady myself. "Your ability to create such a... vivid world is truly astonishing, Max. There is nothing I can teach you, I feel. You are a wonderful writer, and I suspect, destined for greatness, and I will suggest to your mother that she is wasting her money seeking extra tuition."
Max beamed with delight at my comments as I stood by the window, gazing into the garden, praying my erection would subside.
"You have the same problem I do, Mr. Jenkins," Max declared.
"What's that?" I challenged him.
"You like the story as much as I do," he responded. "I can see your delight in my story."
I turned towards the young man, my erection as evident as his. Max's eyes grew wider, and for a moment, we both just stared at each other, the unspoken understanding thickening the air. "Mr. Jenkins, you said you can't teach me, but I think you can," he murmured, his voice a mix of excitement and challenge.
"And what would that be, Max?" I asked, the words barely a whisper as I tried to maintain my professional demeanour.
Max took a step closer, his confidence growing with each heartbeat. "You know the kind of stories I write, Mr. Jenkins," he said softly. "But it's just fantasy. I'm still a virgin, and I thought maybe... You could help me understand more, so my writing can be more realistic."
I felt a mix of horror and fascination at his words as my facial colour turned to that of beetroot. Had he deduced my orientation from my reaction to his story? Was this all some sort of elaborate scheme? Yet, his earnestness was hard to ignore, and the thought of guiding him through his sexual awakening was.... "Max," I began, my voice quivering slightly, "that's not something I can help you with."
"Why not?" he asked, his voice still holding that same childlike curiosity.
"It's... inappropriate," I managed to reply, my eyes drifting to the floor.
"But Mr. Jenkins," Max said, his voice low and persuasive, "You're the only one who's seen my work. Who else can I trust, and I can see you are as much aroused as I am?"
He took another step closer, his hands reaching for the waistband of his Hanes briefs. With a confident push, they slid down his hips, revealing the full extent of his arousal. The room grew even warmer, and the sound of fabric sliding against skin was the only sound that pierced the silence. His cock bobbed free, hard and eager, and I found myself unable to look away.
"Oh my god," I thought to myself, "what the hell is happening?" as I lifted Max, my hands clutching his naked buttocks as I lifted him onto the mahogany table, laying him on his back as his cock pointed towards the ceiling of my study.
His skin was soft, the light dusting of hair on his legs and chest standing out against the stark whiteness of the briefs he had been wearing. His eyes were wide with a mix of excitement and apprehension, but his smile was full of confidence and determination.
"I want this," Max whispered, reaching out to me, his hand landing on my crotch, feeling the outline of my erection through my trousers.
I swallowed hard, trying to compose myself. "Max," I began, but he cut me off with a finger to my lips.
I couldn't resist him anymore. The boundaries that had once been so clear had blurred into nothingness, leaving only the raw desire that pulsed between us. With trembling hands, I unzipped my trousers, allowing them to fall to my ankles, thereby permitting my feet an exit plan. My Fruit of the Loom briefs hid my erect cock as Max's eyes widened even more as he took in the sight, his hand reaching out to touch me.
I leaned over him, my body trembling with need. "Are you sure about this?" I whispered against his lips.
Max nodded, his breath hot against my skin. "I trust you, Mr. Jenkins," he murmured. "I want to learn from you."
I kissed him, our tongues melding together as I explored the softness of his mouth. My hands roamed over his body, tracing the lines of his muscles, the curve of his hips, and the warmth of his cock. His skin was like silk under my fingertips, his scent a heady mix of sweat and teenage lust.
With a gentle tug, I pulled my shirt over my head, feeling the coolness of the room against my bare chest. Max's eyes never left mine as I stepped closer. He gasped, his hands reaching up to touch me, exploring the contours of my body with a hunger that matched my own.
The sound of fabric tearing echoed through the room as my briefs gave way to Max's attempt to tear them from my body, sending a bolt of desire through me. He was beautiful, a young god laid out before me, and I couldn't wait to claim him.
As I stood there, between his dangling legs, I reached for the bottle of lube in the fruit bowl that sat on the table, something I kept for... personal reasons. Max watched me with wide eyes as I squeezed a dollop onto my fingers. "You're going to need this," I murmured, my voice thick with desire.
His eyes never left mine as I reached down, coating my cock with the slick substance. The sight of his waiting body was almost too much to bear.
"Please," Max begged, his hips bucking upwards. "I need you."
And with that, I knew there was no turning back. I repositioned myself between his legs, my cock poised at his entrance. With one last look into those trusting eyes, I pushed forward, feeling the tightness of his body initially resisting my invasion attempts, but after a while and repeated attempts to edge inside him slowly, his muscles yielded to my attempts.
The sensation was overwhelming, a mix of pleasure and pain that had me biting back a groan. Max's eyes squeezed shut, his body tensing as I inched my way in, giving him time to adjust. His breath hitched as I reached deeper, filling him.
"You're so tight," I whispered, my voice strained with the effort of holding back.
Max nodded, his teeth digging into his bottom lip. "It's okay," he panted. "Keep going."
And so I did, my hips moving in a slow, steady rhythm that had us both moaning in pleasure. His legs wrapped around me, his heels digging into my back as he urged me deeper.
Our bodies moved together, a dance of passion that seemed to have been choreographed by fate itself. The sound of our skin slapping filled the room, punctuated by our gasps and moans. Max's youthful exuberance was infectious, and I found myself lost in the sensation of his tight warmth enveloping me. His hands clung to the edge of the table, knuckles white with the effort of holding on as I pushed into him with increasing force. His eyes never left mine, the trust in them unwavering despite the discomfort that was surely written across his face.
I leaned down, pressing my forehead against his, feeling the beads of sweat that had formed on his skin. "You're doing so well," I murmured, trying to soothe his pain with gentle encouragement. His eyes searched mine, looking for reassurance that this was what he wanted, that this was right.
"Yes," he breathed, his voice strained but earnest. "More."
Our connection grew stronger with each thrust, the barriers of our roles as teacher and student shattering as we became two men, lost in a moment of pure carnality. I picked up the pace, driving into him with an urgency that I hadn't felt in years. His legs tightened around me, his nails digging into my back as he met each of my movements with a roll of his hips that sent electricity through my body.
Max's body began to quiver, his breath coming in ragged gasps. I knew he was close, as I pounded his prostate, his inexperience making it all the more intense. I reached down, wrapping my hand around his cock, stroking him in time with my thrusts. His eyes went wide, and with a keening cry, he came, his orgasm painting his stomach with ropes of white.
The sight of his release pushed me over the edge, and with a final, powerful thrust, I buried myself inside him, filling him with my release. We stayed like that for a moment; our bodies joined in a silent testament to the power of desire and the unpredictable paths of human connection.
As we both caught our breath, the reality of what we had done began to sink in. Max's eyes searched mine, looking for a sign that I regretted our encounter. But as I gazed into those pools of innocence and passion, I knew that I could never regret this moment. It was a gift, a shared secret that had brought us closer than I ever could have imagined.
I pulled out gently, the feeling of emptiness that followed making my heart ache. "Max," I whispered, "I think we should..."
He put a finger to my lips, shushing me. "Don't ruin it," he said, a soft smile playing on his lips. "Let's just enjoy this for what it is."
And so we did, for that one perfect moment, before the inevitable storm of guilt and consequences crashed down upon us. But in that brief period, as he lay on the table, surrounded by the scent of sweat and sex, we were simply two beings who had found solace and understanding in each other's bodies.
Gently, I pulled Max up by his arms, lifting him off the table with a strength fuelled by passion. He straddled my hip, his legs wrapping around my waist, his buttocks encased against my hands. I couldn't help but feel a sense of possessiveness and awe at the beauty of his youthful form.
For the first time, I kissed him with passion as his fingers played with my nipples, and then I asked, "Max, what else would you like me to teach you, to make you a better writer?"
Max's cheeks flushed, his eyes dropping to the floor. "Well, Mr. Jenkins," he began hesitantly, "I know that my descriptions can sometimes be a bit... lacking. In my stories, I mean." He took a deep breath, his voice gaining strength. "I want to learn how to write about intimate moments with more... realism, and so, your homework is to read my stories and to point out, with personal tuition, the proper way to be a better lover."
The irony of homework wasn't lost on me as I looked at him closely, trying to find any doubt if he wanted to continue what we had started. Finding none, I kissed him again, mumbling, "Okay, I shall, and I suspect this won't be the last time we share moments like this."
Max kissed me on the cheek, saying, "Thank you and thank you for making the lesson so practical."
"Thank you, Max," was all I could say as he shuffled off my lap, picking up his discarded clothes.
As Max dressed, I couldn't help but feel a sense of pride and excitement at the prospect of guiding him through the intricate dance of intimacy. His innocence was intoxicating, and his willingness to learn from me was both flattering and arousing. As we moved into the next phase of our relationship, I knew that we would be venturing into uncharted waters, but I was ready to navigate the stormy seas of desire and education together.
I showed him to the door and patted his bottom as I said goodbye. The door being now closed, I returned naked to my laptop, lifting the lid and navigating to his profile on GayDemon, reading the synopses of each story. I found one that caught my attention, Canoeing Can Be Fun, and I settled down with a glass of wine to read it, making a mental note of improvements that the author would benefit from knowing.
The silence of my study was broken by the sound of my telephone ringing. It was Max's mother, Mrs. Taylor, whose voice filled with excitement and gratitude. "Mr. Jenkins," she gushed, "Max has told me all about your lesson and how much he enjoyed it. He said you're a brilliant teacher, and he's already learned so much!"
My heart skipped a beat, knowing I was naked, as I tried to keep my voice steady. "Ah, yes, Mrs. Taylor," I replied, "Max is a very dedicated student. I'm thrilled to see him taking his writing so seriously, and rest assured, there's always room for improvement, but your son will get there."
I said goodbye to Mrs. Taylor and returned to my homework, reading the selected story and making a mental note that Max clearly enjoys being outdoors. I sat back in my chair, pondering whether there was mileage in reenacting the scene with Max as I read the final line and closed the lid.
