Chapter 10: Fringe Benefits

Tommy was rubbing his ass once again, but this time it didn’t seem to take any of the sting away. She had used the hairbrush on him, and this time she really went at him, both his butt cheeks still felt as if someone was poking them with pins and needles. God how I hate the hair brush. He thought for the hundredth time.

The reason he had gotten in trouble this time, was that she had gone through his papers and found that he had gotten a C+ on one of his Spanish quizzes. It was his worst subject. He had gotten his Spanish past tenses mixed up. A stupid mistake on a stupid quiz. The thing about it though, in terms of his overall grade, was that the quiz didn’t even count for much in the larger scheme of things, but that made no difference to her. It seemed like Emily just liked to find any excuse on why he needed to undergo one of her punishment sessions. All throughout this latest one, she had berated him on how was he going to get straight A’s if he got grades like this. It was almost like she was looking forward in giving him that special reward she had talked about, which, he realized, kind of surprised him.

Emily, still sitting on the couch, leaned in a bit and finally slid the brush back on the coffee table, and declared, “Well I hope you learned your lesson.” And once again, her voice rang out disparagingly, “A C+. --- How could you!”

She was sitting, wearing just her blouse and panties. She of course had taken off her jeans before she had used the hairbrush on his ass. Not only did Tommy find her lower torso alluring, which he was staring at now, but so was her top. She was wearing one of those form fitting blouses. It seemed to hug her figure, and highlighted the shape of her breasts. The same breast that he had become so familiar with just the week before.

Emily finally let out an exaggerated sigh and continued, “Ok, now that we got that out of the way, let’s get back to our lesson plan for today.”

“While still rubbing his ass and staring at his panty clad sister, Tommy asks, “What are we going to do this time?” There was not the usual excitement in his voice, as his mind was still distracted by the stinging sensation covering both his butt cheeks.

Emily looked over to Tommy, and for the moment, just enjoyed watching Tommy’s discomfort. His unobstructed frontside was being displayed prominently before her. Prominent because both of his hands had reached back behind him to his backside. Those hands were busy rubbing up and down trying to ease the discomfort on his two ass cheeks, which inturn was causing his half-erect cock to jutt out obscenely. With every massage it would bob in front of her. She had to admit to herself, knowing she was the cause of it all gave her some perverse pleasure in a twisted kind of way.

Sitting there, still staring at that remarkable young cock, made her start to wonder. How long it has been since I’ve given a boy a blowjob, since I had felt a male member swell within her lips? How long had it been since she had actually grasped one in my hand and used it so I could lick off the bead of precum that always seemed to appear? How long had it been since I forced one down her throat, suppressing my gag reflexes, just so she could the moans and the guy’s fervid cries of pleasure from above? Staring at the young boys cock she contemplates. Maybe she should perform all these acts now on my brother now. A reward for his good behaviour and devotion he had shown me since we started this. But then she remembered what happened just the week before. How she almost blew it when she didn’t keep her own desires under control. Recalling this caused her to slightly shake of her head back and forth. No, I mustn’t! ... It would spoil everything. If I learned anything last week is that I have to stay disciplined. And anyway. A smirk slowly appeared on her lips. I already have a special plan lined up for today anyway.

So however reluctantly, she broke off this concentration on her brother’s johnson, and forced herself to look up to his face, “So you think you are ready for your next lesson?”, consciously forcing her eyes to stay fixed and not drift back down to the temptation below.

“Yeah, I’m ready.” Tommy replied back, and he was too. In fact, he had been waiting all week for this lesson, thinking this may be the week he’ll finally get to the part of her body he was really interested in.

“Good! You’re going to learn about the women’s legs.”

He felt his hopes deflate. It wasn’t what he had hoped she’d say, but he tried to keep any disappointment from showing up on his face. He was going to continue to be a good slave, after all, she was running out of body parts, and he knew, soon he’d get there. He just had to be a little more patient. And anyway, he really did enjoy these lessons, not only for the most obvious reasons, but also because he really was learning things. He didn’t know when he’d have a chance to try out any of his new skills on other girls, but when that day did arrive, he knew he’d be far ahead of the others boys he hanged with. Resigned to his fate he answered back, “Ok, you want me to get on my knees, like when I did your feet?”

“Yes, but first you’re to bring out one of our kitchen chairs and place it over there.” Pointing to the middle of the family room.

Tommy thought this was a strange request. Why didn’t we just do it with her sitting on the couch, like we had before? But he was beyond the point of trying to figure out everything his stepsister said, and he just dutifully went to the kitchen to retrieve one of the wooden chairs, and carried it back into the family room.

Getting up from the couch and moving over to the chair, Emily at first stands behind it, and placing both hands on the back rest, she says, “Ok, we will start with the feet. In that way, we’ll see how much you remember from that first lesson, but this time you to work your way up. All the way up the legs.” Emily then looked over to his face saying firmly and with an intimidating stare, But you’re to stop before you reach my crotch. --- Understand!”

“Yeah, I understand.”

After the near disaster of last week’s session, Emily knew she had to do something different. This forced celibacy of hers was getting harder and harder for her to take. And the truth be known, the boy was getting to be too good. She knew that having him go about pleasing and worshiping her body, and having her to wait for the lesson to be done with before she could alleviate her pent up yearnings and desires. It was getting to be too much. No, that will no longer work. She concluded. It was becoming sheer torture. She knew she needed to attain some more immediate relief, but that still didn’t mean she wanted to divert from her carefully laid out plans. So she decided to stir things up, just a bit, just enough to satisfy her repressed needs, and at the same time it will serve as a nice addendum to Tommy’s own lessons.

As requested, the chair was positioned right in the middle of the family room, giving Tommy plenty of room to work. She takes her hands off the back, circles around to the front, and sits her panty clad ass on down. Now looking over to her brother, she reflected with more than just a hint of enthusiasm. Ok, let’s find out if Tommy can keep his dick under control, and his mind on his task.

Tommy moved in position himself before his sister and went straight down to his knees, kneeling before her, and looks up to her, waiting.

Emily’s face cracked a smile. She couldn’t help herself but to be amused, looking down on her younger brother, kneeling there, and waiting on her command to start. She felt like some royal sitting on her throne ready to announce a command to one of her adoring subjects. And it felt so good! Really good! With a tight regally grin, she nods her head at her brother and says, “Ok, you may now begin.”

Now given his release, Tommy places his hands on her right foot and gingerly lifts it up. At the same time his face had bent down and he starts by kissing her toes and then slowly moving up his kisses up on the foot. He continued to place these kisses on her foot while intermittently rubbing and caressing her foot lovingly with his hands, but also, from time to time, the side of his face.

“That’s it Tommy, nice and slow. A girl wants to feel every part of her body is special.” Emily pipes in from above him.

Out of reflex, he glances up to her as she hands out her latest critique. It was at this point he noticed that her right hand had moved. It was no longer just resting by her side. Instead both the hand and fingers had drifted down toward her middle, on top of her panties, right over the crotch. And the hand’s fingers weren’t sitting still either. They were slowly moving and stroking lightly over the fabric, obviously trying to stimulate what lay underneath. He found that he couldn’t help but stare at those fingers, like they were some rhythmic hypnotist’s watch, only instead of passing back and forth before his eyes, the fingers were moving the other direction, vertically. They were moving up and down, up and down, over the panties and that beautiful crotch of hers.

A voice rang out, “Always remember this is not a race. It’s a seduction.” breaking him out of this reverie, A smile had suddenly appeared on Emily’s face. Not that Tommy would see it. She thought. She could see where his eyes were glued to. Her plans were already starting to come to fruition. But she decided to be magnanimous (This time.) and concludes her comment with a stern warning. “You’re not done yet Tommy!” She warns him. “You hardly even started, so get off your lazy ass and continue.”

It was hard for him to tear his eyes off that hand of hers, but that’s what he forced himself to do. Convincing himself he’ll be traveling in that direction anyway, and if he was good, followed her directions, and did a good job, then that hand would be sure to stay where it was, and he’d get to see more of what it was doing. Also, maybe, by that time, it may even be doing more. This thought made Tommy more determined than ever to redouble his efforts. With his hands still holding her right foot, gently and reverently, he bent back down and started to softly reapply soft kisses upon it, and he slowly work his way up. He passed her ankles and began to move his kisses and administrations to her lower leg, and calf.

As he worked his head underneath her calf he found he was at a better angle now, so he glanced up to see what that hand of hers was doing, and he was pleasantly surprised to see the light petting had now fallen out of favor. Oh the hand was continuing on her crotch and her fingers still continued to rub itself down there, but the digits were doing so more firmly now, so much so that he could see the panty fabric was folding inward. The direct center of the cloth was being pushed within the tight confines of her two lips. This in turn caused her trimmed pussy hair to spill out on both sides of the panty’s crotch covering. He could swear that he could even start to smell her too, that wonderful fragrance of hers. A fragrance that he had become so familiar with. He quickly averted his eyes, before she caught on, a reconcentrated his efforts to the task at hand.

Emily couldn’t help but feel her body respond. She didn’t know if it was just due to her own hand giving her this nice sensual massage, or maybe it was seeing the Tommy, still on his knees, ass still displaying that nice pink glow, doing his best to please her. At the very least, his efforts were sure adding nicely to the whole experience. Tommy is so good at showing his submissive side. She mused. I wonder if any of his future girlfriends will ever find out this propensity of his ... If any will take advantage of it. She jokingly concluded. Well if they don’t, it will be at their great loss.

Emily noticing Tommy’s face and kisses were at her knee now and starting to move on to her thigh, “You’re doing good. Remember it’s a girl’s inner thigh that’s the most sensitive part of the leg.” She continues with her sage advice. “You’ll want to turn up your passion there, and make sure you spend some extra effort on this area.”

Tommy grinned, for that advice sounded good to him. What better way to find out what her hand was up to then move his effort there. Not only that but my nose will be up closer to detect her wonderful effervescents.

“I know where your eyes want to go Tommy, but stay focused on the legs.” She continued. Her fingers were done now with just teasing her lips, and slipped further down to her vagina now. They were forcefully trying to push the panty material inside her. The strain on the material caused the panty crotch to fold up completely upon itself, not only giving her inner lips a nice stimulation, but her clit as well. As the fingers thrust into her receptacle, the fabric started to absorb the fluids that were slowly trickling out now. “Don’t worry though.” She added. “If you continue to do well in your lessons you’ll get there too, some day.” At the same time another voice was saying inside her head. Or go on Tommy. Get distracted! Get distracted, so I can place my little slave across my lap again. Only this time I’ll use my hand to smack that cute little ass of yours.

Down below the boy was trying his best to keep himself focused. Thinking things like, Come on Tommy, do as she says. If you don’t, you’ll just find her using that brush of hers on your ass again. If you do a good job, then you’ll eventually get up there and you will be able to see what that hand is doing when it’s just inches away, and anyway, she does have a great pair of legs. Just concentrate on the legs.

Emily was once more amazed on how well Tommy was actually performing. He was turning out to be so much better lover than any of her old boyfriends. He actually listened to her, and did what she wanted, and when she wanted, all in order to please her, and not to just get his own rocks off, as had been so evident from all her past experiences with the opposite sex.

Obviously her plan to tempt him was not working. Not yet at least. And just thinking about her entrapping him, so that she could again have that naked boy’s body lying prone, across her lap, with his hard cock pressed against her thighs, and her palms striking down on those two soft, round, meaty buttocks of his, while at the same time lecturing him on all his male failures and weaknesses. All these thoughts were adding to the greatly pleasures that she was feeling.

But fuck! The boy was good! She thought once more, as she spied the boy’s head and felt his lips brush against her inner thigh. Noticing that every once in awhile this young novice would mix it up a little. With slow seductive licks with his tongue, light nipples with his teeth, or soft caresses with his face and cheeks. And never once did she notice him get distracted from his primary task. Oh, she could see him glancing, from time to time, to her pussy and hand, but he never did stop pleasing her. So she decided to step up her game as well.

With his head and efforts concentrating on her thigh, so close to her pussy, this was the optimum time to step up this game of distraction. Not that she minded much, for she was selfishly eager to take her pleasures to the next level as well. After all, by this time she was quite horny. Her panties were clearly showing evidence of this, as they had gotten quite damp with her own fluids. She didn’t know what was turning her on more, she contemplates, Was it because of Tommy’s efforts?, My hand’s? Or was it just because she was actually getting turned on by her own exbititionist, teasing behavior in trying to entice and lure the younger boy into my trap.

She waited. Biding her time and waited until she saw Tommy’s eyes glance up, to spy on her crotch and pussy. At that moment a voice rang off in her head, Now Emily! Now!

Her hand grabbed both sides of the crotch material of the panties and squeeze them together, she then pulled them aside exposing a now slick pussy to the teenager’s eyes. Now, with pussy exposed, her fore and middle fingers slid back into her lips. Sinking slowly down through her slit, carefully prying her lips apart. Deliberately, she exposed the pink inner flesh to his eye.

She was enjoying this, really enjoying this. Enticing her faithful little vassal. Seeing him struggle to complete the task he had been assigned. Her bare fingers continued sliding back and forth over the lubricated flesh, while the palm applied its own pressure, pressing down and in, trying to stimulate her clit.

She could tell her latest expedition was having its effect. His kissing had stopped. His eyes were opened wide and completely glazed over as he stared. And with his face resting on her thigh, his mouth was hanging open and drool was starting to seep out. Oh god, this was so hot. She thought both exuberantly, and somewhat callously.

But then her plans crashed down in flames. For it was then the boy did something completely unexpected, shocking even. All of a sudden she saw him come shake out of his stupor, and after turning back his head to kiss her inner thigh one last time, he then took his lips off her thigh. (His face was only inches away from her crotch.) He then pulled himself back, and lowering his head back down, he bent down to her other foot. (Her left foot this time.) Picking it up gently, Tommy started to place his lips back down on the top of her toes. He started giving applying light kisses to her toes, just like he had done before on her other one.

Seeing her well laid plans going for naught, conceding that her attempts to entrap the boy had failed completely, but instead of being disappointed, Emily felt a euphoric high. She had actually done it! She had turned the boy! She proclaimed to herself, and then thought of what she had accomplished. The boy had changed from being one of those lecherous male teenagers, only intent in pleasing themselves, to now a completely dutiful one. One that put her wishes and needs before his. She felt a surge of pride and excitement, and assured herself. If I could do it to Tommy, then I bet I can it to other boys as well.