Story of a Boy

"You remember your safewords?"

"Yes ma'am."

"Remember what we discussed over coffee? My rules?"

"Yes Ma'am."

"Good. Now strip and let me see you." She smiles a tiny smile then. A bit of mischief behind her calm, stern exterior.

He doesn't feel particularly comforted by that, however. It feels like having sex for the first time as a teenager. Anxiety gnaws at this stomach, and he finds it a little hard to concentrate. He takes off his clothes one by one, as he is told though. He has thought about this exact moment for years now, dreaming about it over and over again in the depth of night, superimposing his fantasies onto reality and wishing both were true. He has come too far to back away now. Besides, she is good and kind, and he trusts her to take care of him.

"Kneel."

He drops onto his knees a little clumsily.

"Recite back my rules."

"I shall be respectful at all times ma'am. Follow your orders immediately. No touching myself or you without permission. If anything is wrong, raise the issue with you using safewords ma'am." Simple. Right? What can go wrong?

"Good boy. Now relax."

Her first real order and he is already struggling. How to relax in this context? Nothing he has learned in the past 30 years prepared him for this particular moment. He tries to focus on his breathing, but all his senses feel hypersensitive. Everything feels a little too bright, a little too much.

She watches him for a moment before coming closer. She is still dressed, but she presses her body against his. He could feel her easily through the soft fabric. She holds him close and let him rest his head on her tummy.

"Touch me if you want."

He reaches out tentatively, first with his hands around her waist, and when she does not reprimand him, he let his hands wander, up and down her back, down her ass and legs. She feels solid and warm under his fingers. Strong but soft to the touch. He feels his arousal perk up and crowd out the anxiety.

All too soon, she pulls away to sit down on the bed.

"Crawl to me."

He does and is rewarded by her guiding his head between her thighs. He is fully aroused now, so close to her, feeling her, smelling her, seeing her up close. His throat feels dry and his cock is painfully hard. He dares not touch though. A new form of torture.

She pets him a little.

"Are you good at pleasing women?"

He isn't sure about the answer to that question. He always approached sex as just something to do, to release pressure, to gain some physical satisfaction. He isn't an inconsiderate lover, but he also never put a tremendous amount of thought into it. Subconsciously he always knew, the physical act of sex can only give him so much satisfaction, so he never examined it too closely, until it was no longer possible to ignore his submissive instincts. The women in his past liked him, a few even loved him, and he loved some of them back when they were together. But he never felt truly satisfied. He isn't sure whether he truly satisfied them either.

"I am not sure ma'am. I am not sure if I would be good enough to please you?"

She looks down at him, not unkindly. "Good. I like honesty. Now give it a try. I will punish you though if you fail."

He feels his chest tighten and blood pound in his ears as she says that. Damned if he isn't a pervert, to be so aroused by the thought of her finally punishing him, putting a claim on him, with marks and bruises for all to see.

He sets about licking her. Cautiously at first, trying to listen for her reactions. She grabs him by his hair soon enough and gives him explicit orders on what to do. She tastes nice as well. The smell and taste of her soon become overwhelming. The sound she makes, her moans and breathy instructions to lick faster or slower or harder or softer...

She makes him keep at it for a long while, but he doesn't feel the time pass. He is too engrossed in the moment, with the thought of pleasing her, the thought of making her cum. She does cum after telling him to lick harder at a certain spot, holding his head down in between her thighs so he can hardly breathe. Her juices rub all over his face as she rides her orgasm. He is so hard now, even a light touch would push him over the edge. He desperately wants to rub himself a little, but he keeps his hands in place around her thighs. She has told him not to touch, and he won't disobey her.

"Not bad. Aren't you a smart boy." She smiles at him. He smiles back shyly, happy that she is satisfied.

"Now, I want you to lie down on the bed, while I get cleaned up. You are not allowed to move or to touch yourself. Understood?"

"Yes ma'am."

He listens to her footsteps as she walks to the bathroom and turns on the shower. He dearly wants to touch himself. He hasn't felt this desperate since he was a teenager, seeing naked girls for the first time.

He resists by counting backward from 1000, trying to structure the code he left unfinished at work...

When she comes out again, she is naked, and all the hard work he put in to dampen his arousal goes straight out the window.

She climbs over him easily and looks at him with a mischievous smile. "Now, let's see how you are doing."

She rubs gently along his cock with her fingers, and fondles his balls, slapping them lightly from time to time. It takes all his self-control not to cum right away, but he can't stop himself from begging. "Please ma'am. Please let me cum. Please." He is usually not bad with words, but in front of her, he seems to have lost all higher mental function.

"You want to cum? Have you been good enough?"

"I. I am not sure ma'am."

"You have been good, but not yet good enough to deserve an orgasm in my presence. You can leave now, and get yourself off when you are alone, or you can stay and be played with. I may or may not let you cum though."

There is no hesitation in his mind, although it takes him a second to find his breath. There is no way he would voluntarily leave her right now, with her perfect naked body in front of him and her slender fingers rubbing gently up and down his shaft.

"I wish to stay ma'am."

"Well then, let's see how good your self-control is." She puts some lube onto her hands and continue rubbing more vigorously. He has to call out for her to stop immediately. He is too close. She frowns and slaps him hard on his balls. That hurt. But even the pain makes him want to cum.

She gives him a bit of a breather before crawling further up his body, with her face close to his, and starts kissing and touching him on his face, his neck, pinching his nipples gently and then harder and harder with each pinch. He bucks against her from time to time, involuntary responses from overstimulation. He dearly wants to touch her back, hold her, kiss her full on the mouth, and drown in the taste of her. But he is not allowed, and she does not seem to be in the mood to give him any more favors.

She kisses further and further down his chest, his tummy, and then his cock. Soft little kisses, before taking him fully into her mouth, sucking gently around the tip, licking him, nibbling just slightly with her teeth. She does this slowly, deliberately, watching his every reaction. He grips at the bedsheets desperately, trying not to buck or force more of himself into her mouth. All he can think of is the need to cum. Every other concern has fallen by the wayside. It is sweet torture, but torture nonetheless at this point. He has never needed to deny himself for so long.

"Please stop. Stop. Stop. I can't."

She pulls off quickly and watches his cock twitch in vain, for that last little bit of friction.

She smiles. Satisfied for now.

"Come and take a cold shower. It doesn't really help, but it is the best you are going to get."

The cold shower does soften his cock a little, but his arousal is still a burning physical pain.

"Now go and build that piece of code you have been talking about. You have an hour while I do some work as well. Then I want you to come down for lunch. You are not allowed to touch yourself at any point. If you need the bathroom, come and ask me for permission. Understood?"

"Yes ma'am."

It was the most unproductive hour he has ever spent coding. Normally he gets into the zone pretty quickly. He loves puzzles and he is good at solving them. He can lose himself in the code for hours without breaking concentration. But this time, all he can think about is her naked body, her taste, her fingers around him.

The problem with being completely distracted, however, is having nothing to show her afterward, when of course, she wants to see progress. She is in slacks again, and a pair of gauzy leggings that hug her body and show off her slender figure.

She is not pleased and frowns when seeing the dozen or so lines of code sitting all alone on his computer.

"Is this what you can manage in an hour?"

"No, ma'am. I can do more..." He feels stupid saying that when obviously he couldn't.

She just raises one eyebrow.

He feels his cheeks glow. He is a diligent person, and good at what he does, so he has never been caught short in such an obvious way before.

"Get on your knees."

He drops to the floor and looks down in shame. He is behaving like a teenager. It is embarrassing.

"I do not tolerate incompetence. Do you understand?"

"Yes, ma'am. I am sorry. It was..." He can't explain what happened.

"This type of poor performance needs to be punished."

"Yes ma'am."

"Crawl to the bedroom, strip, and lie face down on the bed."

It takes a bit of time since crawling is more difficult than it seems, especially on the hardwood floor. But even then, he has to stew in his own embarrassment for a good 15 min before she comes into the room.

He doesn't move from his position, but all his senses are focused on her, her footsteps, the touch of her hand on his back, his buttocks, his legs.

"I am going to punish you now. You will count and thank me after each strike. Understood?"

"Yes ma'am."

The is no more warning before the first strike hit. Probably a paddle or something. Whatever it is, it hurts a lot more than he imagined in his fantasies. She knew how to beat boys, and she isn't holding back just because this is his first punishment.

In between the shock and pain, he forgets to count. And the second strike lands even harder, as a warning.

"Two!" He shouts before belated adding a thank you

"The ones you don't count out loud don't count. We start back at one, so pay attention."

The third stroke lands on top of the first one with a loud thwack, and the pain is even worse.

"One. Thank you, ma'am." He counts, desperate to get through this. He did not realize it would hurt so much. It seemed arousing in his fantasies but the reality of being spanked hard by someone who is obviously in no mood to show mercy is very very different.

She gives him ten. Twelve counting the first two. At some point he gets genuinely worried he isn't going to be able to take what she wants to give. He really wants to though, to please her, to show her he obedience, to be her submissive, to be worthy of her.

The next thing he feels is her hand on his sore ass, gentle, soothing, comfort after the pain. She pets him on his ass, up his back, and down his thighs. From time to time, her hand rubs lightly on his balls and his perineum. This also feels nicer than he imagined. His fantasies have plenty of sex and punishments, but just the gentle calm of her presence and being petted by her feel amazing.

"How are you doing?" She asks

"I feel fine. Ma'am." His voice is a little tight and rusty, but he feels fine now. It is nice even, in the warm afterglow of a good solid beating. He feels oddly relaxed and content.

"Come for some lunch then."

She takes him to the dining room, where food is already laid out on the table. Nothing fancy, but he is plenty hungry now to eat it all. There is only one chair though, and he looks to her for guidance.

She sits down primly and motions for him to go over, and then for him to kneel by her. She then proceeds to feed him by hand, little bits of food from her fingers. This reminds him of his childhood when he used to sneak food to his dog underneath the kitchen table when his parents' attention was turned. It is oddly comforting somehow. She is taking care of him. Making sure his needs are met. He can just be the pet, and not worry about anything. He tries his best to show his gratitude, licking her fingers as he takes the food. Sometimes she lets her hand linger a little, and he licks and sucks on her fingers, hoping it would please her.

After most of the food is gone, she puts some of the messy plates on the floor and orders him to lick up the rest. He is a little embarrassed but does it anyway. It is probably no worse a breach of etiquette compared to all the times he shuffled sandwiches down his throat with coffee while coding with one and a half hands in order to meet a deadline. And he is just her pet now, and a pet should do what he is told.

She cleans up after and takes him back to the study.

"I am going to do some more work now, but since you obviously can't be trusted to do yours', you can spend this time practicing licking pussy."

She ties up his hands behind his back before making him kneel on a cushion in front of her chair. It is an especially designed chair with the seat open in the middle, so he can reach her even as she sits there and works away on her computer. She makes him practice for a while, adjusting the height and position to make sure he is not straining anything other than his cock. Then she puts a heavy collar on him and locks his head in place to a pair of cuffs on her thighs. He can still move his head back enough to breath and to speak, but not much further. With his body chained up this way, he would struggle to stand up or escape even though he is considerably stronger physically. He feels a little scared for a moment - what if she wants him to do this for longer than he feels comfortable? What if she wants to do other things to him? There is no escape now.

But he tries his best to focus on the task at hand and soon loses himself in the feel and taste of her. She does taste amazing. She is wet even before he started, and it didn't take long for his face to be covered in her juices.

She doesn't provide many instructions this time but focuses on her work instead. He tries his best to lick, sucks and nibble based on her instructions earlier.

She works for a while, and then casually puts her foot in between his legs, pushing her toes against his leaking cock. He can't help but rub himself against her. Somewhere in his consciousness, a brief flicker reprimands him for his lust and embarrassing behavior, but the thoughts of how good it feels soon crowds out the shame.

With his head locked in place and her foot just a little too far for sufficient pressure, he can't do much other than leak pre-cum all over her stockings. It is maddening, to be so aroused, but missing just that little bit more pressure to cum.

After what seems like an eternity, she unlocks his collar and his hands and pulls his head back by his hair. His jaws feel sore, as does his back and legs. It must have been a while.

"Get down on all fours and lick up the mess you made on my leg."

He bends down and laps at her leg with his face burning. He is behaving like an untrained dog. How could he? He tastes himself together with the taste of her, all intermingled in this mouth. He was never a fan of licking up cum, the once or twice he tried. But he finds he doesn't mind now when she is there commanding him.

"Good boy. Now crawl to the bedroom and lie face down on the bed."

She comes to the bedroom shortly after, puts down some things on the bedside table and ties his hands back up again. He lies there trying not to think of his cock, but soon enough, a cold, slippery finger starts probing at his ass.

He has fantasized about this for a long time but gets a bit nervous as her finger gently probes in and out of his tight hole. She pats his bum a little. "Relax. I know what I am doing."

He tries to physically relax, and after all they have done, he finds it a lot easier to let go. Her finger moves slowly further and further inside and wiggles a little. Soon enough, a shot of arousal runs through him. That particular spot she has started rubbing, first gently and then more vigorously, in response to his gasps, moans, and incoherent begging, his body tenses to the rhythm of her ministrations, as sweat rolls down his back. He so desperately wants to cum now he probably would have taken his cock into his hands if they weren't tied behind his back. As it is, he can only rub himself against the sheets. She sees that and sits on his legs to prevent him from moving too much. She also stops and starts at irregular intervals, teasing him, making him twitch and whine and beg, but never quite enough to allow him release. He feels desperate, and a bit high, but most importantly, so in need of cumming.

She stops, after the fifth time bringing him just to the edge but not over. He can only lie there and breath. His throat is dry from all the begging and moaning.

"Good boy. Let that be a lesson in self-control for you."

"Yes. Yes ma'am." he somehow grinds out.

"Now I want you to lie here and think about how you should focus on my pleasure at all times."

She puts a blindfold over his eyes and pair of noise canceling headphone in his ears, rolls him onto his side, gives him some water, and then leaves him to just lie there.

He thought he would die from frustration at his point. He tries to focus on her, but his mind still wanders to just now and earlier in the morning, when she was touching him, touching his cock, her fingers inside his body. He can't help it, and his cock twitches helplessly at those thoughts. Lying on his side, he can't even rub himself against anything anymore.

She comes back after a while and looks at him. His cock is still half hard and there is a wet spot underneath it. She smiles a little and slaps him on his balls. It hurt, but not too much. She didn't put that much force behind it.

"You obviously can't focus can you?"

He opts for shaking his head. He is a bit dazed now. It has been a long day of new experiences and emotions and he is getting a little tired.

"Hmm. " She unties his hands and tells him to roll over onto his back, with his hands by his sides where she can see them. She then proceeds to lube up a prostate massager and insert it into him. She turns it on.

"Now, let's see if this helps to increase your concentration."

The massager is set at a regular interval. Couple minutes on. Couple minutes off. He wants to crawl out of his skin. She sits close by and rubs his cock when the massager is on, and he begs incoherently to be allowed to cum, but she always stops at the last minute. She amuses herself like this for what seems like forever. He gives up hope finally. His body is her plaything. His reactions amuse her, but his enjoyment or satisfaction is inconsequential.

She looks at him intently and asks "Do you want to cum now, or be allowed to sleep in my bed tonight?" Earlier in the day, he probably would have asked to cum. But after this last session of her wringing the last bit of sensation out of his body, he wants to be with her, hold her close and feel the warmth of her through the night.

She smiles at his answer, genuinely pleased. She takes out the massager, and cleans up a little before coming back to lie down beside him. She holds him close, her soft body tight against his, and kisses him on the mouth, in full, lingering kisses. She lets him hug her back, lets him wrap his arms around her slender body. He wants to hold her so close, at some point she had to tap him to get go a little. She looks at his face, and leave little kisses all over. He feels high. Everything feels surreal, but the solid weight of her is right there, emanating warmth and comfort.