Chapter 8: The Pop Quiz

It was the following Friday. The parents had left for their date night and had left the two kids home alone again. Tommy was sitting quietly on the couch with the TV on, eager to see what his next lesson was going to be. He thought to himself, while staring numbly at some football pre-game highlights, Whatever was coming next had to be better than the feet.

He had to admit, though, that the feet didn’t turn out to be so bad after all. Reminiscing on the reward he received for doing such a good job of it. He was hoping he’d get something like that today. Just then he heard Emily come bouncing down the stairs.

Emily walked promptly into the family room, where she could see Tommy was conveniently waiting. She was wearing a form fitting light gray capri tights, her top just consisted of a comfortable loose white tee-shirt. and she also had a small bag with her, which she was carrying over her shoulders. She tossed the bag over to the floor against the back of the couch. It hit the wooden floor with a clunk, and then she announced. “So are you ready for your next lesson?”

Tommy had already turned to face his stepsister the minute he heard her, and upon hearing her question, he quickly turned off the TV, and replied with an unforced smile. “Yeah, I’m ready.”

“Good. Today we’ll be moving on to the breasts.” She saw Tommy’s smile grow larger, much larger. She grinned, inwardly thinking, Oh, not so fast my horney little brother. You’ll first have to pass my entrance exam. and then she said aloud, “But before you start cumming in your pants little brother, you must first show me you can master one thing, and that is the bra. Now stand up, and come over by me.”

Curious on what his stepsister was going to make him do, Tommy gets up and walks to the back of the couch, where Emily was still standing.

“First take off your clothes.”

Tommy starts to take off his shirt, but while doing so asks, “Why do I have to take off my clothes?” Emphasizing the ‘my’.

Emily steps toward the now shirtless fourteen year old boy; she takes her hand up to his face. Lightly brushing his cheek with her thumb she says, “If you haven’t figured it out by now, you have to strip, because it’s a prerequisite of mine.” And I like seeing you naked, Bro. She left unsaid. “Now don’t make me wait any longer. Strip off the rest, like a good little slave!”

Just feeling the touch of her hand on his face, gives Tommy’s cock a jolt. It’s like she possessed some strange power over him, and he finds himself stripping off the rest of his clothes, exactly as she had ordered. After his shirt, came his shoes and socks, which was quickly followed by his pants and underwear. He’s no longer bashful being seen naked by his stepsister, but instead feels some sort of inner thrill doing whatever she asks of him. After putting away his clothes on the couch he turns around and notices Emily was reaching for her own shirt. He sees her pulling her tee-shirt over her head, and Emily’s just left with a bra on from the waist up. He couldn’t resist staring at the two covered orbs, thinking this will be the first time I’ll get to see some real boobs.

Emily, pleased in seeing where Tommy’s eyes were drawn to, continues on to the next step of her scheme. “Now as I said, before we can start, you must first master taking off the women’s bra.” She then turns away from him, so her back was now facing him, and continued, “Now see that clasp?” Reaching over her back and pointing out the small clasp holding the two bra straps together. “I want you to unhook it.”

Tommy, with eager hands, reaches out and goes for the fastener. Maybe he was just nervous or wasn’t thinking straight, but unfastening the bra clip was a little trickier than he had expected. But eventually, after about ten seconds or so, and fumbling around a bit, he figured it out and with some relief announced, “Ok, I got it.”

“Now put it back on and do it again.” Emily orders.

He does what she asks. Hooking it back up took him two seconds, and once that was done unclasping it again took him only a second. “Ok, done.”

“Do it again!” She says.

This time it didn’t take him anytime at all. He was able to unfasten it and refasten it in less than a second.

“Again!”

So he does it again. By now he’s getting a little tired of this game. He wants to see those two beautiful breast uncovered, so after unclasping it and re-clasping it once again, he says with an exasperated tone, “Ok, I got it already!’ His voice conveying that he was no longer happy playing her game, and he wanted to move on to the real thing.

“So, you think you have mastered it?” Emily asks him pleasantly, still turned away from him.

“Yeah, it’s easy.” Tommy says assuredly.

“So sure are you? You want to put a wager on it?”

Taken completely aback by her question, he says hesitantly, “What kind of wager.” He was still staring at her bare back, and asking himself, What is she up to?

“I’ll give you five seconds to unclasp my bra. If you’re able to do it, we move on to the breasts. But if you fail, then, it means you’ll we’ll be having a special punishment session, which in fact you’ll be deserving, because of that know-it-all attitude of yours. --- Agreed?”

What did she mean by ‘special’ punishment session. Tommy thought. Tommy was ashamed to admit it but picturing himself naked over his step sister’s thighs again did give him a slight thrill, but the ‘special’ part of it generated a little fear in his heart. “What do you mean by SPECIAL punishment session?” He parrots out loud.

“Oh no Bro! You’ll only get to know that, if and when you lose.” And then just to push him over the edge she decides to egg on the fourteen year old. “Sounds like my stepbrother becoming a bit of a chicken shit now. What is it Bro? You want to chicken out, or do you want to move on, so we can carry on with our lessons?”

Tommy didn’t like being called a chicken. Especially by a girl, even if she was his older stepsister, so with his machismo getting the best of him, he announces, “Ok, I’ll do it.” Still thinking whatever was the punishment she planned to met out, it should be a non-issue as he had mastered the thing anyway.

Hearing him accept her challenge, she felt a tingle all over, right down to her pussy, thinking to herself, Oh, you boys are so easy to manipulate. Hiding her grin, she turns around to face him.

Tommy’s eyes of course was drawn immediately to the two lovely covered tits. He wasn’t sure what size her breasts were in terms of bra size, not being well versed in bra sizes, but they were about medium he’d guess, just large enough that he’d so that they’d fill his hand. He was almost almost salivating thinking about it. Wondering what her nipples were going to feel like when he put his mouth and tongue on them. Thinking to himself, God this is going to be great. I can’t wait to see them uncovered, and suck on those nipples.

Emily seeing her step brother’s hypnotic stare, just grins, thinking, Oh, you’re so dead. She then reaches out and grabs his left hand, with her right, and holds it down in front of her. “Ok, you got five seconds. You can start NOW!”

Her order, jolts Tommy out of his trance, and he tries to lift his left arm, but she immediately jerks it back down. He finds he’s now in a position where he can’t even move around her to see the bra strap, as she’s still holding on to his arm firmly in front of her, so he in turn had to stay directly in front of her.

“Hey, that’s unfair!” Tommy cries out in a whine that sounded more like a little boy’s, instead of a teenager’s, that he would have insisted he had become.

“Remember Bro. Most of the time you’ll be busy kissing the girl. You’ll not only have to learn to unfasten her bra without looking, but many times you’ll only have one hand available. You better get going.” She reminds him and then shouts out, “Four!”

Knowing it would be pointless to argue with her, Tommy quickly reaches around with his right hand, and starts to grope for the clasp. “Three!” He finds it and he starts to fumble around with it. Trying to figure out a technique to unclasp the hooks with just his thumb, forefinger and index finger. “Two!” He could see it’s not working. Desperate now, Tommy roughly grasp the two bands tightly together, hoping that maybe giving the straps so much extra slack that the hooks would unclasp on their own, “One!” He thinks/hopes that may do it, and then lets go. “Zero!”

Feeling her bra still firmly in place, Emily smiles and says nonchalantly, “You failed your test Bro.” Instantaneously the calm voice changes over to an indignant one, “Obviously you haven’t learned a damned thing.” She reaches out for his ear, grabs it, and started pulling on it. “Come here.” Dragging him toward the back of the couch, she pulls his head down. “Bend over the couch.”

Out of self-preservation, he obediently bends himself over the back of the couch, lest he lose his ear.

Letting go, Emily then takes her hand, and pushes his head firmly into the cushions. His head was turned, so that his right side of his head, the one with the sore ear, was pushed down into the sofa. She shouts down, “You are to keep in this position until I give you the ok to get back up. Understand?”

Shocked in how fast things had turned, and still feeling a pain in the ear, that she almost tore off, with a little bit of a boy’s fear, Tommy meekly replies, “Yes, I understand.” He couldn’t believe how her persona had changed so quickly. Thinking to himself, I swear, she’s a regular Doctor Jekyll and Mr. Hyde. He sees her face disappear behind the couch, and then hears the bag unzip, the same one that she had thrown on the ground. After a bit he hears her say, “Now place both your hands behind your back.”

Without a moment’s hesitation, he places his arms behind him, and then feels her capri tights press against his bare naked thighs as she leans over him, and his right arm is jerked firmly behind him to the center of his back. He’s feeling a different kind of vulnerability now, naked, bent over, with her groin pressed against his backside. Shamefully, he feels his dick starts to stir.

When Emily had reached down to her bag, she had pulled out an old hair scrunchy. After securing his right arm with her left, she puts the scrunchy around his right hand, and taking it, twists it around, once, twice around his wrist, nice and tight. She then twist the other loose end a couple of times, and then forces that end around his left wrist. The scrunchy was acting like a cheap pair of handcuffs, binding both his hands together. Oh, she had no doubt that if he really worked at it he could force his hands loose, but that wasn’t the point. The point was for him to know that’s how she wanted him, and for him to break his bonds would be for him to break his covenant with her. She had a good feeling he wouldn’t be doing that. Not when he knew it might risk the good things to come. But just to remind him of that fact, she steps back and reaches behind her, unsnapping her bra, and then taking it off, she takes it and leans over his left side and drapes it right over on top of his head, saying to him, “I’m going to give you my bra to practice with. So after we get done here, you are to take it up into your room and use it to improve your technique.Then if by next week you’ve MASTERED it, we’ll be able to see if we can finally move on with your lessons. Does that sound fair to you?”

Knowing he had no choice in the matter, and knowing she always wanted an answer, Tommy obediently replies, “Yes, that sounds fair.” He was feeling the bra on his face, a cup on each side. He stares up with his uncovered left eye trying to get a glimpse of his now topless stepsister, as she was still leaning over him. Unfortunately the bra strap was right over his eye, completely blocking his vision. All he could see was the top of her head.

“But right now this bra is to serve a secondary purpose.” She continues. “It will show me if you’re really serious about carrying on with our agreement. If you are going to accept that you are my slave, and by being my slave, will accept all your deserved punishments. So, here’s the test. If during this punishment, that bra drops off your head, then I’ll know you’re not serious, and you really don’t want to continue. We’ll stop this game, and you’ll give me back my panities, and you can go back to being a lazy ass self, including not doing anymore of your homework. I’ll even let you take the easy way out now if you want.” She pauses for a moment before continuing with the question. “Do you want to give me back my panties now?”

Tommy felt a pang of fear grow within him, not because of what was coming next, but because Emily was actually thinking of ending this whole thing of theirs, he quickly responds, “No Sis! I don’t want to quit. I’ll take your punishment.” He replies back with just a hint of panic showing in his voice.

“So you still want to be my slave?”

With no hesitation, Tommy cries out, “Yes! I still want to be your slave.” Her right hand slams down on his ass. SLAP! “Well, we’ll see about that.” Then without moving her hand off his ass, she gives the reddening buttock a hard squeeze. Letting go, Emily steps back and then kicks at his left foot, and yells out authoritatively, “Spread those legs wider, slave!” Obediently, both of Tommy’s legs spread out wide.

Bending down to her bag again. She reaches in and brings out her next object. It’s a paddle, a ping pong paddle. She had to borrow it from her friend Stacy, as her family had never owned a ping pong table. At the time, she made up this phony ass story about needing it for some art project. If Stacy only knew. I wonder what she’d say? She kids herself amusingly. She’d been planning this whole thing all week, and seeing her plans come to fruition, without a hitch, she could feel her own juices start to flow.