Jon's Lesson 
© 2001 Jude Mason. 
JudeMason@my-haven2001.com  


Melissa sat in the corner, very near the fireplace, sipping her white wine. She fervently wished that the wait was over, but she’d learned patience if nothing else with Jon. He seemed able to find ways to be late for almost everything. So why should tonight be any different? She finished the glass and ordered another from the young man serving. He grinned, a knowing grin she thought. Her growing annoyance was much too evident. Her tall slender body became stiffer the longer she sat looking out of the large window into the gardens. 

Halfway through the second glass, he finally made his entrance. Not quite as tall as Melissa and very slim as well, he hurried towards her. He’d allowed his wavy blonde hair to grow just a bit longer than was fashionable, at her request. The suit he wore,
although very masculine couldn’t hide what she saw in him. He neared the table and looked down at her, a look of concern on his face 

“Melissa, I’m really sorry about being so late.  Traffic you know, it was really bad all the way here and I should have started earlier. Can you forgive me, please?” His voice trembled with eagerness trying to placate her. He shifted nervously from one foot to the
other waiting for her to reply. Melissa continued to gaze out of the window, ignoring him for a minute or two. 

“Please Melissa, I’ll try to do better. May I join you now?” A hint of desperation in his tone made her smile. Turning to face him she tightened the corners of her mouth and snapped. 

“Forgive you. I’ve been sitting her alone, for almost an hour. Do you know what can happen in an hour? Do you realize how many men have been looking at me,    undressing me with their eyes while I wait for you? How embarrassed I was when the waiter asked if I’d been stood up?” Her tone left him cringing. 

What a mess he’d made of it this time, he thought. Hanging his head he remained quiet, knowing how useless it was to try and defend his tardiness. It just kept happening, he couldn’t understand why, but it did. 

“I prepared for you this time though Jon. If you wish to continue seeing me then you’ll comply with my wishes now. If not, you’re free to leave. I’m very sure I can find another man to fill my needs.” She left no doubt in his mind that she was serious.
Gulping, he lifted his eyes to meet hers, and quickly dropped his again. 

“Please Melissa, let me sit down before we go any farther.” He whined. 

“If your answer isn’t the right one Jon, you won’t be sitting down here. Now what will it be? Leave and I’ll never see you again, or stay and obey me.” She’d leaned back in her chair facing him. Long nylon clad legs crossed at the knee, one shoe pointing its toe at his crotch. Squirming, Jon quickly realized she meant every word she said. 

“All right Melissa, I’ll obey you. Now can I sit please? I feel extremely uncomfortable standing here like this.” Placing her half empty glass on the table, Melissa reached inside the tan leather bag on the table. A quick search, then her hand withdrew bringing
with it what seemed to be a bunch of leather straps. Then to his total horror, she spread it on the table  

“Please, Melissa, don’t.” Jon began. His face had turned a very bright crimson when he realized what it was. 

“Now then Jon, my pet, I want you to take this and go to the men’s room. Once there you will go into a stall and strip off your trousers and underpants. The underpants, put in your pocket or the trash; I really don’t care. You won’t be needing them for awhile.” 
The shocked look on his face fuelled her appetite for his lesson to begin. She continued at her leisure. 

“Make sure you’re erect, then put this on. If you comply quickly with my commands, I’ll stay with you. If you refuse or if I think you’re tardy I’ll leave. If I leave you now, you’ll never see me again.” She pushed the leather strapping towards him and waited.
She didn’t have long to wait. Moments later he reached for and took the small bundle into one large hand. 

“Yes ma’am, I understand. I know I’ve been very hard to deal with just lately. A lot’s been going on at work. I know that’s no excuse, but that’s all I have. I’ll try to be on time from now on. Honest Melissa, I’ll do better.” He tucked the small treasure into the
pocket of his suit jacket. He stood, as if waiting for something then. Melissa let him wait. For several minutes she gazed out of the window while he stood nervously in front of her. When she decided he’d stood long enough, she looked up at him and with a grin, nodded her head towards the men’s washrooms. 

“Well, what are you waiting for? I told you to go and put it on, not stand there gaping at me like an idiot. Move!” Her tone was harsh and he quickly spun on his heel and headed towards the far off corner where the lavatories were located. 

By the time he reached the door he was sweating. What on earth could Melissa be doing? What was he doing complying with her demands? They’d been dating for
several months and he knew she was a bit bossy, but this; well this was outlandish. He’d never dreamed of anything like this. Not that he’d admit it to anyone even if he had. 

Pushing through the door he was relieved to see the room was empty. Quickly he crossed to the stalls and entered one slamming the door shut behind himself. Then for a moment he stood with his back against the door, eyes closed and shuddered. Could he go through with it; did he really want to? These and more questions raced around inside his head. The sensation of his growing erection gave him the answer. Reaching into his pocket he pulled out the leather contraption.


With a faintly audible sigh he hung the straps over the hook on the back of the door. Slipping out of his shoes first, he stood for a second before continuing. His pants unfastened then dropped, followed by his blue silk boxers. He’d planned a very different evening that’s for sure. Folding his pants and shorts; he placed them carefully on his shoes. Taking the  black leather straps he maneuvered it to fit snugly around his shaft and behind his swollen testicles. It was designed to hold his entire package forward, making him appear even larger than he already was. Blood pumped into his prick and as he reached for his slacks he could feel it throbbing against his belly. 

The shorts set aside for the moment; he struggled into his dark grey slacks. His manhood stood straight upwards and when he fastened the top of his trousers was held flat against his stomach. There was no way to hide the bulge and he dreaded the walk back to the table. His shorts found their way into the pocket of his suit jacket and his shoes slid back onto his feet. He rubbed the front of his pants, gently squeezing himself. He’d never worn anything like it before and he was learning very quickly just how much he liked it. Taking a deep breath he opened the stall door and headed towards the door. Glancing into the mirror, he could see his erection quite clearly. Buttoning his
jacket hid the obvious bulge but did nothing to relieve the growing tension he felt. 

The walk back to Melissa’s table seemed twice as long as when he’d gone the other way. He was sure everyone was watching him, knew he had a harness squeezing him
and knew he had a huge hard on. Melissa sat watching him approach, a smile crossing her face. When he stood  in front of her he stopped, and waited.  

“Bit warm for the jacket isn’t it Jon?” She asked innocently. 

“Uuh! You know why I’m wearing it buttoned. Could I sit now, please?” 

“Take off the jacket first and give it to me, then you can sit.” Holding her hand out she took his jacket when he shrugged out of it. His hands moved self-consciously to cover the front of his pants. She motioned him to one of the chairs so he’d be sitting with his back to the room, but facing her.

“Take your hands away, I want to see what you’re trying to hide. Spread your legs and be still, and be quiet.” Her voice was very firm and he complied with her wishes immediately. Hands dropped to his sides and his knees spreading wide to show her the results of her commands. Leaning forward she reached for him. One hand cupped the bulge of his testicles and she could feel him throbbing. 

“Looks a bit uncomfortable Jon. Maybe you should unzip your trousers so I can have a look at it.” Melissa’s voice was hushed, but the words echoed in his mind. Unzip, how could he here? Her hand caressed then tugged on his tightly confined testicles making him shudder. 

“You mean here? Melissa, you can’t be serious? What if someone sees me?” Her hand tightened even more around his testicles. He cringed, his legs beginning to close. She kept up the pressure until his mouth shut. 

“Are you going to start arguing now Jon? Yes, I mean here, you’re facing me so no one will see, unless I wish it. I am very serious and if you don’t comply immediately I will leave.” She snapped harshly at him.


“Spread your legs and unzip your fly. Now!” He jumped slightly, his knees splaying wider apart. Then slowly, his hands moved to obey. Nervously, he looked around
to make sure no one was watching, then he unzipped his fly. He kept his hands over the gaping front of his pants, trying to hide himself. 

“Drop your hands Jon. Straight down, hold the seat of your chair. That’ll keep them out of my way. Now be quiet.” His hands dropped to the sides of the chair grasping it tightly. Melissa hadn’t stopped pulling and teasing his testicles throughout. He was flushed with excitement, as well as embarrassment but continued to comply with her wishes. Then she reached inside. 

“Melissa, please! Don’t, you’ll have someone looking. Please stop.” Desperately he tried to persuade her to quit her tormenting. She still held him by the testicles; her hand gripped tighter to control him. He gasped when her other hands encircled his shaft then
pulled his prick out into the open. Then with practiced ease, she pulled upwards, bringing his tightly harnessed balls tumbling out as well. 

“Now isn’t that a pretty sight. My but you are excited aren’t you?” She teased him mercilessly. Pumping his shaft slowly from the leather bound base up to the plum coloured head soon had him moaning. 

“You’re going to learn to be on time Jon. I’m sick and tired of waiting for you. Whenever we go out together you’re late. From now on, you’ll do as I tell you or
you’ll be on your own. I won’t put up with it any longer. Do you understand me?” Her fist moved up and down as she lectured him. His lack of punctuality was the last thing on his mind at the moment. He desperately wanted to cum, but he was totally embarrassed by the entire situation. His eyes dropped to watch her hands on him. His lack of response earned him another ball crushing grip as he watched and groaned softly, praying no one would hear. 

“Ahh! Yes, I understand, oh God, Melissa stop!” He clenched the cheeks of his butt in a vane attempt to ease the pain. The tight strap around the base of his erection kept him hard, agonizingly hard. The large head of his prick looked red and angry, its tip wet with pre cum. 

His mind was in turmoil. He’d never been so totally humiliated before, but he’d never been so turned on before either. He felt as if he were going to explode into her hand. He gritted his teeth waiting, praying, wishing he was anywhere but here. But also, much to his surprise, not wanting to be anywhere else. 

Melissa loosened her grip on his testicles, and watched as he sank into his chair with relief. She also noted how horny he was. More so than she’d ever seen him before, that was for sure. His prick throbbed in her hand but she had no intention of allowing him that pleasure quite yet. He needed to learn a lesson first. 

She let go of him, completely, and sat back in her chair to see what he’d do. Nothing for seconds, then he raised his eyes to hers, begging without uttering a sound. He dared not move, or she’d leave and he knew it. So he sat there fully exposed while she drank the remainder of her wine. People moved around but none close to them thank heavens, he thought. His erection sagged just a fraction while they sat, him eying her
and her ignoring him. Or so it seemed to him. 

When she’d finished her drink, she motioned the waiter over to their table, covering his groin with a napkin. It barely concealed him, and he stared at nothing while she asked for the bill. 

“Nothing for the gentleman?” The young man asked quietly. Jon sat as if deaf, afraid to breathe. The seconds dragged on, until finally Melissa rescued him.


“No, nothing. He’s not much of a gentleman either.” She quipped. His face flushed crimson once again, but he dared not argue with her. The thin linen draped over his manhood would take very little to be dislodged. 

“Thank you ma’am, I’ll be right back with your bill then.” And the young man turned away. Jon listened as his footsteps receded, then disappeared. 

“You’re awfully quiet Jon, cat got your tongue? I think you’re beginning to enjoy this somehow. Feeling submissive are you?” Her voice, although soft, could be heard several feet away, and he feared others would hear her. His fingers had tightened on the seat of the chair, aching with the pressure. His penis however, had hardened to its maximum girth and ached. 

“Melissa, please, enough. I won’t be late again, I promise.” 

“I asked you if you were enjoying this. Your cock says you are. Look at it bobbing and waving around. You’d better learn some control or that napkin will drop.” Her meaning was very clear and he moaned. 

“Yes, I’m beginning to enjoy it. Now may I cover myself properly?” He agonized over his situation, but also he was thrilled beyond belief. 

“No. You just sit there and be quiet for now. Do as you’re told and everything’ll be fine.” The last was spoken quietly, and then Jon heard footsteps approaching. 

“Your bill ma’am, will that be everything for you; and your companion?” The sarcasm couldn’t be missed, but Jon couldn’t raise his eyes. 

“Yes, thank you, that’s everything. Time to go Jon.” Smiling innocently at him, she rose to her feet. Jon’s mouth dropped. He couldn’t get to his feet, not now, not like this. He sat incredulous, while the waiter turned and hurried away. 

“You will not do up your slacks. I don’t care how you leave, but if your slacks are fastened, I’ll punish you.” He looked up into her face and saw the determination there. Gulping, he nodded his head. Then taking his jacket from the back of her chair he laid it over his arm. If he were careful he’d be fine. Draping it just so, he was hidden. He rose to his feet and followed Melissa to the front desk. 

He held his erection close to his belly as he walked, preying that no one would notice. The sway of her rear enticed him more than ever, and his eyes seem glued there. She of course knew he’d be watching, deliberately accentuating each side ways undulation.
She stopped abruptly. He bumper into her stumbled then stood stunned. Melissa spun around and smiled wickedly at him. Then, let her eyes slowly drop to the jacket he held tight. He knew what she was thinking, and he
also knew he just couldn’t do it. 

“If I told you to give me your jacket, would you do it?” The silence lasted until Jon had to breathe again. A gasp, then he closed his eyes as if in prayer. 

“Please, I can’t you know I can’t.” 

“Only you say you can’t Jon. If I said, right now, give me your jacket, would you hand it to me?” The smile she offered him was almost cruel. He dropped his gaze, defeated. 

Yes, I’d hand you my jacket Melissa.” Barely a whisper, the words seemed to come from someone else’s mouth. He stood as if in shock, which in a manner of speaking, he was. The realization that he would calmly hand over the only thing covering him shook him badly. He’d never felt so confused before in his life; turned on and weak at the knees, at the same time. Taking a deep breath, he shuddered, then raises his eyes slowly to hers. 

“Please don’t ask me to Melissa. I’d do it, but there are people here who know me and I’d be ruined.” She spun on her heel, heading for the entrance, and left him standing there. Gulping, he followed her again, his eyes once more dropping to the curve of her
bottom. Straightening his back, he meekly followed her once again finally catching up to her at the till. She handed her credit card over and waited patiently while it was processed, then signed her name quickly. Card quickly found it’s way back into her wallet, and that slipped into her bag. Jon stood behind her to the right, heeling her without even thinking about it. She did though, and glanced back at him before turning
towards the door. Stopping, just before it she waited.


“Well?” She demanded. Gasping, feeling the utter fool he quickly strode past her and opened it. Melissa stepped through into the warm evening air, then turned and headed towards her car. Jon, still holding his jacket against his groin rushes after her. 

“Melissa, how much longer are you going to keep this up?” The whining qualities in his voice became an irritant all of a sudden. She came to an abrupt halt then spun to face him. 

“Jon, you’ve been inconsiderate and rude to me for too long. If, and it’s a very big if, we are to continue you will do as I tell you to or I’m through with you. I’m fed up with your rudeness, and won’t have it any longer. Got it? Your choice.” Harshly, the words spat from her lips while he stood, gaping at her. 

“Melissa, please, you can’t mean this. We’ve got along really well haven’t we? I’ve paid for my mistakes surely with this little episode of public humiliation; don’t carry it any farther.” His tone belied the nervousness he truly felt as he tried to bluff her.
The erection throbbing against his belly signified its approval of their new relationship. 

“Jon, don’t push me. I’ve had enough of your attitude and could very willingly walk away right now. If you want to continue with me, it will be under very different circumstances. No more expecting me to do your bidding. Wait for hours while you think of yet one more excuse for being late. I’m tired of picking up after you when you come to see me. I’m just plain fed up. Either you listen to me or I walk.” Her heart
beat faster as she felt the anger rise inside. Jon stood just two feet away, his jacket pressed hard against his crotch. His eyes dropped then, and she knew she had him. In a quivering voice, his answer came as no surprise to her. 

“All right Melissa, you win. I’ll listen to you and do what you tell me. I’m sorry for the treatment I’ve given you. I’ll do anything you want.” 

“That’s more like it. Now hand me your jacket.” Cringing, then checking around the parking lot, he held the jacket out to her. Both hands quickly dropped to his crotch trying to confine the raging hard on thrusting out from his middle. His face flushed when
he saw her eyes lower to inspect him. 

“Yes, I see you’re beginning to like this a lot. Put your hands behind your back and keep them there until I tell you otherwise. Very good Jon, now to my car.” She turned and walked towards her car and he hurried after her, his erection swaying and slapping his thighs. 

By the time he’d made his way to the passenger door she was in the drivers seat, ready to leave him standing there. He prayed she’d stop and let him in. He stood outside the door not daring to move his hands from behind his back. Turning, she watches him
standing in the window then motions for him to get in. Relieved, he opened the door. 

“Hold it, right there. Now then, unfasten your slacks.” Her tongue flicked over her lips as if anticipating the taste of something good. Jon unfastened the button and allowed his pants to fall to the cement. He straightened and she watched the blush become more severe. 

“Please, can I get in now?” He pleaded. Grinning, she reached out and tapped the pulsing head of his erection. It bounced upwards slapping at his belly. 

“Take off your pants.” 

“Oh God, no! Please Melissa, don’t do this to me.” She sat waiting, her fingers again flicking at his tip. Thirty seconds later he still hadn’t answered her, so she left him. Sitting up in her seat properly, she turned the key and put the car in gear. 

“Stop! Okay, you win! Anything you want. Just don’t leave me here, don’t leave me.” He lifted one foot and kicked it free of his pants, then stood on the other leg. Struggled for a moment then pulled his leg out.  Soon he was done and he straightened up, his prick was so hard it stood up against his belly. His testicles thrust towards her being help out by the harness she’d given him. 

“I want you to tighten your harness.” Without another word, he obeyed her. His fingers pulled and stretched his sack, forcing his testicles to bulge lewdly out. It took a minute or so, but he managed to tighten the straps. 

"Nicely done Jon. I see you’re learning. Took you enough time though. Spread your legs and masturbate for me. Don’t cum or I’ll be angry with you. That wouldn’t be good right now.” He sighed as he grasped the shaft and began slowly pumping. He was incredibly  turned on and close to coming even before he touched himself, now, he gritted his teeth. His balls ached to be emptied, feeling as if they were being held in a
vice. 

“In the glove compartment there’s some lube, get it’ Jon leaned into the car, retrieving the large tube of KY. He stood up again and looking at her unscrewed the lid. A small mound filled the palm of his hand then he tossed the tube onto the seat. 

“Jon, you made me wait an hour for you tonight. I think you’ll give me one hour of a show. One full hour, and if you come before I tell you, there will be trouble.” Slowly, and with great care he began to cover himself with the slick lube. He knew he’d climax
if he wasn’t careful and dreaded whatever torment Melissa might dream up for him. The gel felt cool against his heated member and he sighed, slipping his clenched fist down the shaft. The straps of leather held him very tightly. The head of his prick tingled
as his fist passed over it on its trip upwards. She had him continue for several minutes, always keeping an eye open for someone passing by 

“I think you’d best get in before someone comes along and sees you. Unless, of course, that’s what you’re trying to do.” Melissa chuckled when he scrambled into
the car finally permitted to hide his nakedness. Then sitting beside her he stroked himself; bringing himself to the edge, time after time, while she sat and watched. Jon couldn’t believe the feelings coursing through his body as he obeyed this woman.
He’d never felt anything even remotely like this and he wanted it to go on forever. Trembling with excitement he ached to climax but waited, at her command. Each time he felt the churning in his balls he tightened his grip, squeezing himself hard to delay
his pleasure for her. The minutes dragged on and he wasn't sure how much longer he’d be able to last. The tensing of his butt threatened to take him that tiny bit too far and he groaned, trying to hold off 

“Please Melissa, I’m sorry, let me cum now. I’m so close, I’ll do anything you say, just let me cum now.” Jon’s desperation made him sound like he was growling 

“Oh dear, you’ve still got almost six minutes Jon, you better hold off just a bit more.” Leaning back against the drivers door Melissa allowing her knees to part  slightly. Then she raised her skirt just enough to show Jon the scrap of cloth covering her sex. Damp
from her own excitement, she reached down and caressed herself. A small shudder coursed through her body as she gave herself the first small release. Jon sobbed
his fist tightening on his prick; his eyes glued to her crotch. 

“Don’t you dare cum yet Jon. Three minutes, that’s all you have to wait. If you cum too soon, I’ll be very upset and you’ll be punished. “ Sternly, she admonished him. Then, with a wicked grin, she squirmed and wiggled out of her silky white panties. Holding
them out to him he could smell her excitement, which only added to his own 

“Here Jon, I want you to cum on my panties. Let’s see, you have two minutes. Think you can do it? Rub them over your prick; do you like the feel of them?” Her
eyes glazed with excitement at the control she had over this man. With a trembling hand he grasped the offered slip of cloth. Carefully he wrapped them around his prick and began to caress himself with them. 

“Aahh! Yes, I like the feeling of them. Oh God, let me cum now Melissa. Please, I’ll do anything. I’ve never felt like this before.” 

“Now stop. Take your hands away and put them behind your back Jon.” Melissa snapped sharply at him. A cry escaped him but he complied, reluctantly. She grasped
him firmly and stroked his length, very slowly tormenting him. Her panties covered the crown and were wet with the copious amount of pre cum he’d produced. 

“I want you to cum now Jon. It’s time.” No sooner had she given him permission than he began to climax. His body jerked uncontrollably as his erection throbbed in
her fist. She pumped him dry, the crotch of her panties filled with his offering. He gasped with each eruption, his thigh muscles tensed. Melissa continued to stroke him until she saw him cringe, his pecker now over sensitive. Releasing him she pulled her panties off and handed them to him. Shocked he took them, wondering what new torment she had for him. 

“Messy, Jon. How am I supposed to wear them like that? You’d better clean them for me. Lick your cum off them, there’s a good man.” As he bent to obey her, she
continued. “I think you might be an acceptable companion, with some training. Useless for a while though, shame. You seem to be enjoying yourself, something new for you. I’m going to leave you now Jon; I want you at my house bright and early tomorrow
morning. I expect my panties to be freshly washed and you to be harnessed. Eight o’clock sharp or there’ll be trouble. I’m sure you understand. Where’s your car?” The question surprised him, the entire conversation took his breath, but he pointed across
the lot at his small import. His mouth was still busy in the crotch of her panties. Looking over towards his car she nodded then began to speak again. 

“Good, you can get out now. I’ll allow you to take your slacks but not to put them on. I hope you’ve learned something today Jon. I won’t put up with any more of your misbehaviour again.” 

Looking up into her eyes Jon for the first time seemed to really understand his new place in life. He couldn’t meet her gaze for long, dropping his eyes to stare at her legs. His erection had waned but not totally disappeared. He would have loved to continue
but he’d been told now to leave her.

“Yes, Melissa. Thank you and I’ll do as you’ve instructed. I can see I’ve been less than what you want. I’ll do better.” His heart was still beating fast as he took his slacks and opened his door. 

Melissa watched her new toy as he made his way quickly across the parking lot. He would be at her door at the specified time, attired in whatever she requested.
Straightening her skirt she began the short drive home wondering how he would train. 

The end

©2001 Jude Mason. All rights reserved, not to be reproduced in any form without the permission of the author.

About the author: Jude Mason has been writing most of her life, but only since finding the internet has she dared to share her erotica. She's been published in Amatory Ink with, 'Dance of Submission,' has her own website ~My Haven~ and works hard to improve her skills as an erotica writer.