Sweet Jonathan Pt. 01

Writer's Note: Sweet Jonathan is a romance tale from the point of view of Mia Belsor, a curvy thirty-something English teacher divorcee who finds herself attracted to her tutoring charge, Jonathan. Jonathan, she finds, is gifted in all the ways she prefers, but suffers from very poor self-esteem.

This will be a bit of a slower burn, but the intention is to wrap it up in just a few installments, unlike my previous works. Themes/tags include: Romantic, Older Woman Younger Man, Masturbation, Big Breasts, Big Cock, Cum, Teacher

All Characters engaging in sexual activity are 18 or older.

Please, if you enjoy the story, I would greatly appreciate your feedback. Thank you!

Chapter 1

For the fifth time that evening, I ignored his clumsy attempt to inconspicuously check out my breasts.

"Jonathan, focus. I know you can do this. What does Holden feel when Stradlater takes Jane out on a date?"

"Frustration?" the young man offered.

"Go on..."

"and um...inadequacy?" he said, finally meeting my eye. The uncertain-yet-hopeful gleam in his cobalt blue gaze was all-too-typical and evoked a desperate need to urge him on. But I did him no favors by making things too easy on him, which made being able to give him genuine praise all the sweeter.

"Excellent! See? You're getting it. You just need to pay attention."

He mirrored my sunny smile, a seldom-seen dimple appearing on his left cheek.

It was hard to deny the small thrill I got at seeing his rare unveiled happiness. The way it lit up his pale, finely featured face and touched his eyes was quite disarming. He was more striking than ruggedly handsome, but I wondered again how someone like him could be afflicted with such a lack of confidence. His presence in my English classroom was that of a ghost; from the moment his slender six-foot frame trundled in and huddled behind his desk till the bell sent him loping onward to the next class.

"Thanks, Miss Belsor," he looked away again, remembering some well-entrenched habit to retreat from my gaze, "it's just because you're such a good teacher."

I felt my insides warm, but I gave him a sober look. "Don't sell yourself short, Jonathan. You need to have more confidence. You're doing great; be proud!" Reaching under the table, I tried to give him an encouraging pat on the knee, but in doing so, my fingers grasped something that was not a part of his leg. I pulled my hand back sharply, offering a perfunctory apology. The contact made him jerk reflexively, and his other thigh slammed into the leg of my dining room table, sending the English text tumbling to the floor.

"Ow! S-sorry!" he stuttered, reaching to pick up the book.

He said something else, but I missed what it was, too focused on the feeling of whatever I had touched. My mind whirled, trying to postulate what it reasonably could have been. I knew what it felt like, but there was no way it could have been that... It would have had to reach nearly to his knee! And it was too big around, too. He must have had a small apple in his cargo pocket. Or maybe a packet of tissues.

Shaking myself, I pushed back from the table. "Why don't we take a break?" I said, avoiding looking at him while still feeling a vague impression of what I'd touched in my hand. I moved into the kitchen, heading for the fridge. "You want something to drink?"

"Uh, sure. Thanks."

"Coke, or Fresca?" I asked, leaning in to see what I had. "...or iced tea?"

"Whatever is good."

I sighed at the indecisiveness that seemed to plague his gender, grabbing a Fresca as he'd seemed to enjoy it before.

Setting the drinks on the end tables in the den, I beckoned him to the couches, "C'mon in, have a seat. Excuse me for a moment, I've gotta use the little girls' room."

He hadn't moved from the table by the time I'd made my way to the powder room. Locking the door behind me, I pulled my pants down and sat, looking at my left hand as if it held the answer to the mystery while I relieved myself. Maybe it was the cold drinks from the fridge that put it in perspective, but something occurred to me: it had been warm.

Did I dare to hope that shy young Jonathan was packing what I thought he might be? Just the thought of it sent butterflies fluttering through my stomach.

Ever since I left the asshole, Nick, my god-awful mistake of a husband, I'd hadn't met a man that could satisfy me. And I'd learned the hard way how Nick had carried all of the personality traits that usually accompanied such an endowment.

But even if it were true, what then? The reality of our student/teacher relationship brought my fantasy plummeting to Earth. Would it be worse to know what he was and be unable to do something about it, or not know and wonder if there existed a man that could live up to my towering standards?

Who was I kidding, I had to know!

Finishing up, I returned to the den to find Jonathan sitting primly at the far end of the couch with an accent pillow in his lap, looking around the room as if to signal that his mind wasn't still reeling from my touch. I chuckled softly to myself. Poor, simple Jonathan.

Despite all of it, I bubbled with excitement for the next part of our tutor session: the goss. Each Tuesday and Thursday we got 90 mins of one-on-one time that his mother paid me for, but this was our little secret. After the first couple of sessions, it was obvious that I couldn't keep him engaged in English and Calculus for an entire hour and a half, so I decided to break it up and give him some time to talk.

Mia Belsor, Guidance Counselor.

When we'd started these tutor sessions a couple of months back, it was like pulling teeth to get him to open up. Eventually, he relented somewhat under my innocent questions, happy to find an uncritical listener. As for yours truly, a 34-year-old woman that hadn't been on anything remotely resembling a successful date in well over two years, I ate it right up.

Picking up the soda from the table, he thanked me and cracked the top. I did the same with my tea, pulling my long legs up next to me on the couch to get comfy against the armrest.

"Well? C'mon... Dish!"

He gave me a small chuckle and started talking of small things in his clipped way. Comments about how harsh some of the other teachers were with the delinquents, what so-and-so said about who's-her-face online, and how crazy he thought his friend Scott was for planning to ask Allison Chance to the dance.

All the while I sat back and sipped my iced tea, projecting interest even for the topics I found dull. Knowing that he likely needed this release just as much - if not more so - than he needed the tutoring. His usual hunched posture irritated me, perched at the edge of the couch like a nervous bird. I had made it my mission to get this boy to come into his own, now more than ever before, but he was proving to be a tough nut to crack.

"Why?" I asked, "What's wrong with Allison?"

The look of distaste at my question about his attractive female classmate had me giggling inside, knowing how simply his mind worked. I chastised myself for thinking how delicious it would be to run circles around this boy.

"Allison?" he spluttered, face reddening, "She's! She's...not a nice person." He said in his usual succinct way, eyes taking in the floor once more.

Oh, my sweet sweet boy, always struggling to express yourself. His blush was just as much teenage lust for an attractive female as it was anger and frustration at her bullying. I felt pity for him and wished I could give him a comforting hug without it being inappropriate.

Growing up was never easy.

"Look, don't worry about Allison. High school girls think they have the world figured out, and they couldn't be more wrong. Believe me, I would know. Someday you'll have girls like Allison dancing to the beat of your drum," I leaned over and put my hand on his knee again - the other one this time - managing to hit my target, "What matters in love is that you're a good person and you always respect women. Eventually, girls figure out that swagger and aggression aren't all that, and that quiet confidence, strength of character, dedication, and kindness are the real prizes, and I have a good feeling that you've got those where it counts. Well, maybe with a smidge more confidence," I held up my thumb and index finger close together, smirking, "but you're a catch, Jonathan. I mean that." And I really did mean that, if what he had in those trousers was what I suspected he had. "With those eyes and gorgeous head of hair you've got, I know plenty of women that would be quite interested in getting to know you.

"Heck, if you were ten years older, I'd be right there with 'em." I shot him a wink.

Did that cross the line? Maybe. Probably. But this boy's psyche ached for praise like a farmer's crop in drought thirsting for life-giving rain.

He blushed deeply, picking at the pillow fringe, but I gave him a moment to absorb my words. Soon his eyes tracked from the floor back to my face, taking in my expression. Testing it for sincerity. His desperate hope almost broke my heart. Seeing the truth, he gave me a small grin, still as red as a ripe cherry.

His leg was warm under my hand, and I resisted the urge to give him another squeeze to take the measure of his muscle. He was thin but wiry, and I felt strength in him that years on the soccer field had developed. The thought of biting that adorable dimple on his cheek popped into my head unbidden. I had always found Jonathan attractive, but more as someone I admired from afar, and just in a general sense, like how one might find a particular sunset beautiful. It was never something I felt desirous of myself. But now... Well, I was looking at the boy - the very developed boy - in a whole new light.

Snap out of it, Mia! Control, woman, you're twice his age! Mentally, I shook myself, letting go of his leg and dispelling the wholly inappropriate thoughts of comforting this boy in ways that his mother would have been right to report to the school board.

"T-thanks, Miss Belsor. That means a lot coming from a beautiful lady like you."

My eyebrows rose at his unexpectedly bold compliment. I knew my charms. The eyes of the male students - and staff, much to my chagrin - at Riggs High never failed to find my womanly attributes throughout the school day. But the guileless praise of this powerfully shy young man had me dizzy with pleasant feelings.

I turned to give him a wide grin from the side of my eye. "Flatterer."

"It's true!" he blurted in the way that 18-year-olds are wont to do, "You're the nicest teacher, and so smart and pretty. Even the girls say so. They're so jealous of your..."

I hadn't thought it was possible, but his blush got even deeper, and I caught his darting glance at my chest. I'd always tried to downplay them with my attire, at least after Nick, but there was no way to hide the overabundant bounty I'd be blessed with. I pretended not to notice him pushing down on the pillow in his lap.

"Er, sorry. My Mom's right. I do say stupid things all the time." He shook his head.

Just then, I had a devilish thought: what would it feel like to tease him a little?

"You know, Jonathan," I said, sliding down the couch to get closer, "I don't think you say stupid things." Placing my hand on his thigh under the pillow, I gave him a meaningful look along with a light squeeze. "On the contrary. I think the things you say can be very...sweet."

Inside, I was torn. Why was I being cruel to this young man? I knew I needed to stop, and that I was really crossing the line here, but a part of me relished the power I held over him. He just looked so frightened and adorable, I wanted to eat him up. His eyes darted to my lips and taking his cue, I leaned in, closing my eyes to continue the charade.

As the distance between us closed, the spongy softness of my right boob pressed deeply into his left arm. His shallow, rapid breathing and trembling arm were a sweet potion to the predator inside that I had never known was a part of me.

Suddenly, he hunched over, pushing down into the pillow in his lap with his forearms as his shoulders tremored forward.

Oh my God. He just...

Jonathan sat there, quivering and curled in upon himself, making it abundantly clear what he now experienced.

"Oh, shoot!" Springing from the couch, I flew to the kitchen to spare him the further embarrassment of having to ride that out right next to me, "I just remembered that I left the milk out! I'd better go put it back in the fridge."

Standing in the next room, I stared at the wall for a moment in disbelief before I shook myself out of it, puttering around making noise so it sounded as though I were busy with some chore. Every action was autonomic as my insides went chilly with guilt and fear. I'd used that poor boy to feel good about myself. Why? Because he was kind and gentle, and the furthest thing from a threatening male I'd ever seen. Nick's polar opposite in every way. What a wretched woman I was. Fear for the trauma I was even now causing the nice young man gnawed at me, and the prospect of losing my job didn't help. How could I make this right?

The sound of the bathroom door closing from the other room announced that it was probably safe to return, so I did.

"Everything okay?" I called.

"Yeah, sorry, I just have to use the bathroom real quick." His reply was muffled by the sound of the ventilation fan.

"Take your time."

Chewing my lip, I searched for how to handle the situation to avoid embarrassing both of us even more. 'It happens to lots of guys'? Too disingenuous. 'You're just young'? Too condescending. 'It's not a big deal'? No, that'd just call more attention to it. Probably best to just ignore it and move on.

But I needed to make sure that he would be discreet with my brazenness. My silly, stupid teasing. One whiff of that reaching his mom or the school and I was finished. I'd seen it happen plenty in the news. At least he wasn't a minor, so it wouldn't land me in jail, but there was still the teacher/student impropriety thing.

He was gone for quite some time, and I started to wonder if he might need a change of shorts, but I didn't have anything that would fit him, regardless. I busied myself with looking over the textbook for the coming session to see what we could cover before we broke for the night.

Soon enough I heard the sound of the toilet seat lid flipping up, and immediately after, a loud splashing noise. Dear Lord! Was that the sound of him peeing? It was like someone had set a garden hose nozzle to 'Jet' and was spraying it into a bucket of water! I had no idea why I'd never noticed it before, but the fantasy of what I'd grasped earlier making that sound had me suddenly flushed with arousal.

Eventually, Jonathan emerged, visibly flustered and unable to look up from the floor. The tall young man tried to put his back to me as he moved briskly to the dining room, doing his best to cover his crotch with his hands. I made a show of studying my can of iced tea while I heard him scrambling to gather his books.

"Something the matter, Jonathan?" I inquired innocently, "Won't you come sit down?" I patted the couch.

"I can't." He spluttered, "I-I'm sorry, I just can't."

When I looked up, I found him lowering his packed backpack to his waist to conceal his shame, but not before I caught a glimpse at his shorts. They were soaked! It looked like someone had hit him with a water balloon right in the groin.

I stood there, trying to tear my gaze away, but unable to keep myself from staring as he shuffled to the door. My prying eyes didn't matter in any event as the boy steadfastly refused to look even in my general direction on his dash to the door.

"Jonathan, wait!" I called after him, "I'm sor-"

The front door slammed, cutting off my attempt to apologize for my ill-advised shenanigans.

Hearing only the ticking clock in the still silence of my apartment, the guilt that crushed me felt like a tangible thing. That young man would probably be describing this night to a therapist many years from now. I had to make it up to him somehow, and I couldn't wait until tomorrow.

Frantic now, I dialed his cellphone. He picked up after only a few rings, surprising me.

"Hello?" His voice was low, timid.

"Jonathan, please don't hang up. You left before I had a chance to apologize." He said nothing. "I acted very poorly and made you...uncomfortable as a result. By rights, I should be fired from my job as your teacher for what I did. I'll understand if you want to report me."

Silence. My heart was pounding with fear at the possibility that he might do just that, but I owed it to him to be honest about the situation.

Hearing no reply, I continued, "I-I want you to know that...you shouldn't be ashamed about what happened tonight at all. I caused th-"

He cut me off, blurting out, "No Miss Belsor, it's my fault! You're perfect and kind, and I did that filthy thing..." His words were barely more than a whisper at the end, "Please just don't tell my Mom. Please? I'm begging you."

"Jonathan, there is nothing to feel badly about," I asserted emphatically, "And it is most certainly not filthy! If it'll set your mind at ease, I promise that I won't say a word about this to your mother, but I'm the one who should fear the consequences of her finding out about this evening. Why on Earth would you worry?"

"Are you kidding?" his voice was strained, incredulous, "She'll kill me! She says I'm a disgusting mess when I have my episodes. If she found out that I'd done it in your home, she'd kick me out, I'm sure of it."

I blinked. 'Episodes'?

"Kick you out? You can't be serious! Jonathan, I don't want to make you uncomfortable talking about this, but you must know that what happened is a perfectly normal thing for a healthy young man to do."

"You don't understand. Ugh, this is unreal." I heard him lean back in his seat in frustration, "I can't believe I'm talking about this with you, Miss Belsor. The Miss Belsor, of all people. I'm so embarrassed I could die."

He was right. I really didn't understand. What kind of nonsense was that mother of his putting into the boy's head?

"Jonathan, you are not a disgusting mess. I'll say it again: this is normal for teenagers, and it certainly isn't the first time I've been audience to it. More than that, this is my fault, not yours. I'm starting to think that maybe I should resign..." I said in a speculative voice, feeling my guilt double with the manipulation.

"No! Please don't do that, Miss Belsor. You're my favorite teacher. I don't know what I'd do if you left. I'll never say a word about any of this, I swear."

"That's sweet, Jonathan, but I'm the adult here, and I'm not sure if I'm comfortable with us keeping this a secret. I committed a serious ethics violation." I let that sink in for a moment, and felt even worse when I continued, "On the other hand, if it'll spare you embarrassment to keep this between us, I suppose that's more important."

His sigh of relief on the other end was audible. God, I was sick. He had no clue that I'd played him like a fiddle.

"Thank you, Miss Belsor, thank you! I swear, I won't tell a soul."

"Alright, Jonathan, then I will keep silent as well if that's your wish."

"Please," he said resolutely.

"Well, that's settled then. But we didn't get a chance to tackle that Calc work. How about we set up an extra study session for this weekend so I can make it up to you. No charge, of course." I offered.

"Um, I dunno, Miss Belsor. If my mom found out we were doing a make-up session, she'd probably just ask questions."