Sweet Jonathan Pt. 01

"Ahh, right. Well, we still need to get back on track somehow. Why don't you just be honest with her: you need an extra session before our test next week, and I offered to do one for free as a special exception. She can't be upset about that, right?"

"Yeah, I guess not. Okay then. Thanks, Miss Belsor. Well, bye."

"Goodnight Jona-"

He hung up mid-word. I chortled at that. Teenagers. Phone call decorum was a new and completely unexplored frontier.

The stress and waning adrenalin high from the last hour or so left me feeling exhausted, but the fact that my foolishness was unlikely to lose me my job would at least let me sleep peacefully tonight. It was getting late, so I washed and brushed, changing into my pajamas before climbing into bed with a new book.

As I lay there trying to absorb myself within the plot, my thoughts wandered to young Jonathan's quiet presence in my apartment that evening. The feeling of that solid, warm appendage - I'd come to accept that, given all the facts, it could be none other than his superlative cock - in my hand along with the powerful sound of him putting it to use in the bathroom had me reeling. Those brief moments were indelibly seared into my recollection, playing out over and over in my head and making me hornier by the minute.

Reaching under the covers and discarding my book, I pressed needy fingertips to my slit, arching my pelvis to feel the pressure on my clit more deeply. Untying the cotton pajama cord at my waist, I shimmied out of the pants and slid my palms up my inner thighs while bringing my legs together. They slid to my burning vulva, rubbing deeply into my engorged lips through the thin layer of cotton. My button felt swollen and longed to be played with, the fuzzy fabric sliding deliciously on the little head that peaked up from beneath its sheath.

Oh, Jonathan! I need to show you just how wrong that mother of yours is. Never, ever be ashamed of that magnificent cock, and all of the wondrous things you might do with it. All the blissful things you could do to me with it.

Yes, leave it to teacher. Miss Belsor will show you what a good boy you are. Show you all the splendid facets of a woman in the prime of her life. Take away the deep hurts inflicted by your unworthy mother, and make certain you never again call yourself disgusting or filthy. Dispel all those ugly thoughts about your body as an instrument of shame or guilt.

Come to me, lovely Jonathan, and take comfort and succor. I will draw you to my welcoming breast and bid you suckle, showing you what a loving creature a woman should be. Whisper sugared words of tenderness and passion in your ear to show you what a beautiful boy you are. To free the masculine and virile part of you caged within.

Yes, come to teacher.

A scene played out in my mind's eye then; the two of us picking up where my earlier indiscretion had left off. Our lips making contact. Mine plush, wet, and insistent; his tentative and shy but eager, responding to my cues with increasing fervor. My tongue teasing at his, leading him in the chase and revealing a world of oral delights. Large breasts pressing upon him with sublime softness, filling his head with thoughts of gentle, feminine things. Of what a mother should be. One hand cradling his head to reassure him and simultaneously halt his nervous retreat, the other questing for the prize he offered underneath the pillow that sat upon his legs.

Reaching his inner thigh, I found immediately the very subject of the lustful thoughts that had been plaguing me all evening. Massive and firm, it radiated heat, pulsing with the beat of his pounding heart. I caressed its length with a gentle touch and it responded, bucking at my hand like an angry bull yearning to be set free. Desperate to breach its confines and perform its raison d'etre within my fertile body.

As the fantasy unfurled, I reached to my nightstand and withdrew my largest dildo. A thick nine-inch model, I placed its head in my palm to gauge the size and authenticity of the simulacrum. It failed to measure up to my recollection, but it would have to do for now.

The students and faculty of Riggs High may have been completely in the dark as to just how wanton their senior class English teacher was, but if she had her way, a certain dark-haired boy with deep, sapphire eyes would soon find disillusionment!

Reaching down, I hooked my thumbs beneath the band of my panties and lifted my bottom from the bed to slide them down my legs, watching with interest as a strand of my arousal came away from my burning slot. I smeared the head of the dildo on the soaking crotch of my panties, and probed my gooey pussy with two fingers, adding to the lubrication of my implement. Groaning in pleasure as I pumped the substitute phallus within me, the stimulation of the evening had me nearly boiling over with lust. I hastily unbuttoned my top, letting my huge breasts loll to the sides of my chest under their substantial weight. Pinching one taught, thick nipple, I rolled it between thumb and forefinger, relishing the spike of pleasure it brought me while imagining the blue-eyed boy nipping at them gently with his teeth.

The dream sequence from the couch disappeared in a flash, and suddenly the fit young man was naked, advancing on my supine form on his knees. Pale, milky white skin clothed his slender frame, the subtle muscular build of a runner giving his form relief that I ached to explore with my fingertips. His towering cock was glorious to my sight, bobbing with his movements.

My eyes were fixed upon it, and in the dreamscape, I found my suspicions to be true: it was the most magnificent specimen of male anatomy I'd ever beheld. Praise indeed from a would-be member of Size-Queens Anonymous.

Plunging the now disappointing dildo within my depths, I fueled my own ardor, frantically working it in and out as deeply as I could, angling it up slightly in an attempt to hit that sensitive little bundle of nerves with each thrust. Eyes tightly closed, I visualized him atop me, ready to sink himself into my welcoming womanhood. I admired his gentle face and thick head of dark, wavy hair as he gazed at me with adoration. The look on his face was one of immense gratitude, happiness for being given the privilege of satisfying me, and I felt true affection for him in return. Confident as I was that this young man would never abuse me emotionally or physically. Would never shame me or take advantage of my regard, or leverage his relationship with me to gain standing with others. His eyes were filled only with gentleness and a desire to please.

Suddenly, I could take no more, and my climax was upon me, coming more powerfully and urgently than I had experienced in many long years. My toes curled as I experienced a bomb of pleasure explode in my nethers, shock waves of bliss radiating up my spine and down into my legs.

I lay back, spent, and resolved now to make this sweet boy mine.

*************************

The next few days in class with Jonathan were awkward. I had counted on this, but he steadfastly avoided my concerned glances, refusing to meet my eye. Eventually, as all things do with time, this passed. Within the week he had reverted to his previous tentative-but-polite demeanor.

I had devised a plan to win his affection, and in the weeks that followed, I began to lay the groundwork to execute it. My strategy, put simply, was to show him kindness. So unlike what he had received from the adolescent females at school or even his own mother, I would care for him as no one else did to repair his shattered self-image. Nothing overtly romantic or sexual, of course. I knew that he held himself, and in particular, certain parts of himself that made me tingle in my special places as I dreamed of them in bed at night, in disdain. He would never feel free to share that side of himself if he believed that he was such a low, disgusting person. This, I needed to change, and the first step was to build familiarity and trust.

Still, I had my vanity as a woman to preserve, and I delved within my closet for outfits that I hadn't worn in years. Clothing sure to inflame the minds of men, but specifically chosen for one man: young Jonathan. Each I selected in a bid to encourage more obvious signs of tumescence in my classroom. Low cut tops to emphasize my bottomless cleavage and skirts that clung to the sinful curves of my hips and tight buttocks. Heels to show off my well-turned calves and long, slender legs. For the first time in long years, I felt alive with passion for a man with whom I might truly grow to love someday, making the woman within me blossom for the whole world to see.

In between stealing glances at him to catch his classroom leers, I put much effort into building a bond between us. Over the ensuing weeks, I doted on him as a mother, older sister, or invested aunt would. I sent complimentary text messages to tell him how proud I was of his improving grades (which really were improving, much to my satisfaction as an educator). Sent him polite requests to stay after class from time to time just to say how handsome I thought a particular article of clothing looked on him. Praised his ability to speak up in class with increasing regularity. And perhaps most importantly, offering counsel - sound counsel, at that - for his endeavors to engage with female interests.

It seemed his crush, Isabel Tanner, was to be my chief rival for his affection, though neither teen knew such competition existed. I wasn't bitter or resentful of the girl, of course. I'm not some insane, possessive woman, after all. Isabel was a kind soul that studied hard, and I was confident that she would do well in life. She glowed with youth and had a gorgeous mane of fiery red hair, both of which I felt a shard of envy for. Yet I found solace in the fact that she possessed only a shadow of my curvy voluptuousness - the kind of curves that I knew lured sweet Jonathan's gaze.

To outward appearance, Isabel was completely oblivious to Jonathan as the two sat through my English class, but I caught the lingering looks she cast in his direction when he put his books away, and flinty, frustrated glares when he stared at my tactfully revealed cleavage. That sort of thing might slip by young Jonathan, but it would never escape my vigilant scrutiny.

They were on friendly terms, and he had recently worked up the nerve to invite her to study at his home, which she'd accepted. I'd coached him on how to achieve some degree of familiarity with her, and he'd been grateful. The night after the 'date' - as I rightly referred to it given how she no doubt considered it - we had a tutoring session that proved to be a watershed in my journey to win the young man's regard.

"So, are you going to keep me in suspense? How did the date with Isabel go?" I urged, literally on the edge of my seat.

We were early in our session of 'couch time' for the evening - sessions that, I recalled, had seemed to grow longer and longer over the past weeks without either of us (or Jonathan, at any rate) realizing it.

"Miss Belsor," he whined, "I told you, it wasn't a date, it was a study session."

"Yeah, yeah," I waved that off, "Okay fine, have it your way. How did the study session go?"

"Pretty good, actually. I touched her casually from time to time, just like you told me to, and it was great! I was so nervous she would get offended or angry, but if anything she seemed to like it!" He gushed, clearly far more comfortable to express complete thoughts around me than in weeks prior, "Like one time, I sort of fell into her to grab her upper arms gently after I told a joke, and she got the biggest smile."

He was giddy with happiness, and my heart soared, doubling in size despite the amateurish way he'd implemented my advice.

"Jonathan, that's fantastic!" I said, reaching over to give him a congratulatory rub on the back, the irony of the moment not lost on me. "See? I told you she liked you!"

His expression sobered, and he ran a hand through his thick wavy hair, momentarily distracting me. "Well, I'm not sure about that... I mean, she seems to like me okay. But whether it's 'like me, like me'," he air-quoted, "or just 'friendly like me', I'm not sure."

Oh, dear God. I almost felt pity for the poor girl. She was probably bashing her head into a wall last night trying to judge how much more obvious she could be without slapping him upside the head and matter-of-factly telling him that he would, in no uncertain terms, be joining her to the dance next month as her date, and that yes, she expected the flowers, corsage, and the whole girlfriend treatment.

"Jonathan, Jonathan, Jonathan..." I shook my head despondently, "What am I going to do with you?" I muttered, looking up as in supplication to a higher power for assistance. "She "likes you, likes you'," I mimicked him, "you big dummy!"

At first, I became distracted by his goofy grin, but I quickly realized that he was staring directly into my eyes. Unabashedly staring. Those gorgeous lapis lazuli gems looked directly into my soul, enchanting me. He was always so timid... This was real progress! In celebration, I caught myself pushing an errant curl of his unruly hair behind his ear.

"Have confidence, Jonathan," I murmured, "she's yours for the taking if you have confidence."

The look in his eyes was inscrutable, but he hadn't looked away. My heart leaped at the moment we'd just shared.

"So," I said, breaking our connection, "what's your next move?"

He deflated at that. "Hmm, I'm not sure."

"Well, you'd better think of something, because if you care about this girl, you've got to keep after her. No need to be anxious about it though, just take it one day at a time, and text her about small things. Trust me, she wants you to text her." Weighing his reaction carefully, I could tell that wasn't quite it though. There was something else that was making him nervous about spending time with Isabel. I looked at him with concern. "Jonathan, are you alright? You look tense." I said, giving him a little friendly rub on the arm.

He swallowed, nodding. "To be honest, I kinda am."

"Go on."

"Well," he chafed his arm in apprehension, "it's about my, uh, condition." He glanced at his lap, and then back up at me.

Alright, now we were getting somewhere. I'd been waiting impatiently for the right opportunity to get him to open up to me about this, but knew that he had to initiate the conversation. If I were to do it, he'd almost certainly clam up.

"Condition? I'm afraid I don't understand."

"Uhh, yeaaahhh..." he trailed off, falling back into his old habit of staring at the floor. My heart broke to see these patterns still prevalent after how far he'd come over the last weeks and months. Looked like I was going to have to help him along a bit.

Very gently, I said, "Jonathan, does this condition perhaps have to do with the fact that you're always covering your lap with a pillow?"

He looked down at the aforementioned pillow and sighed in frustration, eventually nodding resignedly.

"I see. We're friends, aren't we Jonathan? Won't you talk to me about this? I don't bite."

"Yeah, definitely, Miss Belsor, we're friends. But you're...you. It's like going to the doctor, you know?"

I tilted my head in confusion. "I'm sorry, I'm afraid I don't."

"Okayyy, so let's say you needed to go in for a colonoscopy, which would you rather have performing the procedure: a wrinkly old dude who you can be comfortable around, or a hot young guy that gets you going?"

I laughed, "I see your point. But what does that have to do with me?"

"C'mon, as if you don't know..." he looked extremely skeptical.

"Know what?" I prompted. It's okay, Jonathan, you can say it...

"Because you're like my dream woman. You're perfect in every way! You're like the moon; you're untouchable."

My heart stopped beating in my chest while fireworks exploded in my mind. It felt surreal to hear the young man I'd become so taken with say those words.

Pull yourself together, Mia! You're acting like some lovesick teenager yourself! Strangely, though, I did feel like a teenager. Just like back in high school, wanting so badly to hear that the boy that I liked felt the same way I did. I wanted to remind myself how silly I was being, but my rational side had completely flown the coop; I felt like I could float right out of the room. Something halfway between a squee and a giggle was bubbling up inside me, and I had to make a real effort to suppress it to avoid dying of embarrassment. I needed to keep the upper hand here!

"Sorry, Miss Belsor. That was inappropriate, I know..." he backpedaled.

Oh, no! My mind was a fog of pleasant endorphins that his sweet words of praise had delivered to me, and I was having trouble tracking the flow of conversation. Snap out of it, you silly woman!

I shook my head, finally mastering myself.

"No," I placed my hand on his, looking into his eyes, "it was sweet, what you said. I...thank you. That's the nicest compliment anyone's paid me in quite a long time."

He seemed incredulous at that. "Really? No way! I bet guys tell you stuff like that all the time."

"Actually, no...they don't. They might act like it, but that's a very different thing to a woman, believe me."

He smirked, and I felt like swooning at the roguish cast it lent his face. "Well then, I guess I'll have to do that more often, won't I?"

"My!" I made a show of fanning myself (which was only half-show, in truth), "You're quite a charmer, aren't you?" I laughed to take some of the heat out of the room, and then sobered, thinking about the leap I considered taking next.

I psyched myself up. Should I say it? This would have been the perfect moment, after all. The perfect setup. Just six little words, and nothing could ever be the same between us again.

'But what if I weren't untouchable?'

But I didn't. I chickened out and said nothing. Visions of a nervous Jonathan retreating into his shell, unable to react at all, and eventually pulling away from our friendship entirely out of discomfort, terrified me. The more I thought about it, the more confident I was that I'd made the right choice. He was far from an emotionally healthy, well-adjusted young man with enough self-confidence to be able to put himself out there and meet me halfway in a real, adult relationship.

My emotions were on a rollercoaster of insane highs and terrifying lows, leaving me feeling drained, but I realized that although he wasn't yet ready to accept me romantically, that didn't mean that I couldn't leverage what had transpired to move forward on other fronts...

"Boy, I'm thirsty, how about you?" I asked, dispelling the sexual tension from the room with my mundane request, "I got some Oreos at the store today. Want some?"

"Mmm, Oreos!" he gushed, "You know it, thanks!"

After I'd returned, I set the tray down on the coffee table and handed him the plate of cookies. Now for a different tack in my attempt to get him to tell me about his problem.

"So. I understand you don't feel at ease telling me about it, but can you tell me if this is a medical problem? You called it a 'condition.'" I furrowed my eyebrows.

He nodded, twisting off the cap of the black and white cookie and licking the cream filling out. I smiled at his youthful antics.

"I'm not sure if it's a medical problem, exactly, but it's definitely gross. My mom tells me that all the time."

"Stop that," I said harshly, "that is not true, and you know that. We've spoken about this before, and I've told you that what your mother has said to you about this is wrong, Jonathan. It's very wrong. What that woman did to your self-image by filling your head with tripe like that is absolutely deplorable!" He recoiled a bit from my anger, but I needed him to understand how strongly I believed this, "I realize that it will take time for you to come to truly accept what I'm telling you, but I want to hear you say it."