Chapter 9: Make up Exam

Oh fuck, the brush. I hate the brush! Tommy thought, staring down at the object that was now lying on the coffee table. I guess I should just be grateful it’s not the paddle again.

He had come down to the family room when Emily had called. Knowing that after the parents had gone (for their date night) and that he would soon be tested. He had been up in his room trying to get as much last minute practice in as he could. He believed he was ready, but you never knew when it came to his stepsister and what sort of trick she might have in store for him.

Seeing Tommy’s obvious trepidation, and still feeling a bit guilty for that trick she played on him, Emily says a little humbley, “Do you think you’re ready for your make up exam, or do you want another week of practice?”

“Still looking down at the dreaded brush, he announces, “No, let’s do it. I’m ready.” And he was too. He had practiced with the bra every chance he got this week. It took him awhile to figure out how best to go about it with only one hand, and even before that, he had to figure out what was the best way to set it all up so that it sort of simulated a bra being worn by a girl. In the end he had wrapped it around the back of his desk chair and used a stiff pillow from one of the downstairs couches to simulate the girl’s back. It wasn’t perfect, but it seemed to work.

Emily looked at her stepbrother from top to bottom, “Well, aren’t you forgetting something?”

Tommy himself looked down and then realized what she was referring to. He had been so hyped on passing this test that he had forgotten her one prerequisite. He started to strip off all his clothes, putting them neatly on the sofa.

Smiling now, watching him undress, Emily speaks, “Ok, we’ll repeat your test. Same rules apply, you still have five seconds, and as you already know, if you fail, it means another punishment session.”Looking up and down at the now naked boy, she gives him one last chance, “You still think you’re ready?”

Tommy found himself swallowing hard, but then replied, “Yeah, I’m ready.”

She steps forward, so that they were facing each other face-to-face, like last time, but this time she grabs his right hand and arm. “Ok, you can start. -- Now!”

He had already foresaw her forcing him to use his left hand, but what he did not foresee was the obvious one, that she’d keep her top on. Tommy, decided not to waste any time whining about it, and quickly wraps his left arm around her and pulled her forward into him, crushing her and her breasts into his chest, and then reaches for her shirt.

Emily surprised at Tommy’s newly aggressive tactics, she grins, before managing to remember to shout out, “Four!”.

Tommy roughly pulls the shirt out of her waistband, and then reaches under the hem.

“Three!”

Reaching under her shirt, for the clasp, he now uses the technique he came up with, and practiced, up in his room all week long. Using his thumbnail, he places it in the seam that was right next to the strap’s loops, while his forefinger and index fingernails held the other end firmly in place, this was the end that held the hooks. Using his thumbnail now, he pushes the loops past the hooks and they separate.

“Two!”

Feeling the two ends separate, Tommy, let’s go of both ends and cries out in exhilaration, “Did it!”, but then it hits him. His stepsister might not have appreciated his rough treatment he had just given her, and he starts to wonder what her reaction will be. He takes his hand slowly out from under her shirt, and releases her and then backs away, slowly, cautiously.

“Well done, Tommy.” Emily says, giving him a big smile, at the same time stepping back toward him so that they’re literally face-to-face again. “You’ve shown me you’ve mastered the bra.”

Tommy breathes a sigh of relief, and he had just begun to relax, with his face breaking out in its own smile, when he feels a sharp yank from down below. A hand had grasped a hold of his cock.

“Now let’s move on to the fun stuff, shall we?” Emily says. She then starts to walk, dick firmly in her hand. Out of the family room they go, walking toward the stairs. “Come on, follow me. I think it’s best if we continue this lesson back in my room.”

Tommy follows as best as he could. After all what choice did he have being led the way he was. She was still holding onto the cock, all the way out of the family room, past the dining room, and on until they reached the stairs, where she let go. But that was done only to adjust her grip from an underhanded one to an overhand grip. He knew he should be protesting this latest treatment. She didn’t need to do this, pulling him along the way she was. All she had to do was tell him where they were headed, and he, of course, would’ve followed her willingly, more than willingly. He found it very awkward going up the stairs. He was forced to take his steps one by one, with the cock firmly gripped the way it was. He had to time each one of his steps to match hers or he would feel a painful jerk. But instead of complaining, he accepted it, and stayed silent. He wondered why this was so. And then he came up with the reasons. One, he didn’t want to upset her in any way, being so close so getting something he had so looked forward to this past week, and two, although he’d be loath to admit it, it felt good having her hold him like this. His cock could sure attest to it. It was starting to emerge from its pre-testing jitterish flaccid state, to now a blood engorged one, and it was still getting stiffer. And it wasn’t only due to the knowledge of what he was soon to experience. No, instead it was due to that warm firm hand that had tightly engulfed his cock and that was controlling his every move. His every action, like he was some puppy on a short leash. Again he found, that for some reason, being humiliated and controlled by his stepsister was an unmistakable turn on for him.

Dick still in hand, Emily leads the young teenager into her bedroom, she finally lets go, and says, “Sit down there.” Pointing over to the edge of her bed. After seeing him sit down, she takes off her blouse and then takes off the already unclipped bra. Walking toward him she asks, “Have you ever felt a real breast before, Bro?”

Tommy just shakes his head, eyes transfixed on the two beautiful orbs on her chest. He was feeling nervous, but he was excited at the same time.

Emily smirks at his response, and says, “Didn’t think so. Ok, give me your hand.” She takes the outstretched hand, and places it on her left breast. “Go ahead and feel it.”

Tommy just lays his hand on it, afraid to do anymore but to touch it.

Snickering at her step brothers trepidation, Emily finally says, “Go on Tommy, squeeze it a little, it won’t break.”

Tommy does as directed, squeezing the breast softly with his hand and fingers. He couldn’t believe it, he was copping his first feel of a girl’s breast. It felt wonderful, so soft, so warm, and it was so beautiful. His cock was fully engorged now, stiff as a board, not that he noticed anymore, all his attention was on that one thing. (Well two things.)

“Now take your thumb and rub the nipples. Stimulate them.” Emily says, continuing her instructions.

Tommy does, and immediately notices the nipple harden and swell.

“The nipples are the most sensitive thing on the breast, see how it grows and gets hard. Almost like your little prick.” Maybe it was due to seeing the excitement in his eyes as she went about teaching the young boy, but Emily felt her lower extremities start to respond as well. “Now pinch the nipple with your finger and thumb, but not to hard.”

Tommy does so and Emily surprises herself when she lets out a small moan, before recovering and responding with a, “Yeah, that’s good. Now do it to the other one.” When Tommy follows the instruction, by reaching out with his other hand so both breasts were being stimulated at once, Emily tilting her head back in pleasure, sighs, “Yeah, that feels real good.”

They continued this for a bit more, with Tommy getting more and more comfortable doing what he was doing. He noticed how the nipples had grown harder and now jutted out. He also noticed that the nipples weren’t perfectly symmetrical. The right one was a bit larger than her left one was. He wondered if this was true for Emily, or were other girls like that too

“Ok, now that you know what they feel like, I’m going to lie down in bed, and then I want you to lie down on top of me, so you can start to practice using your mouth and tongue.”

Emily gets on the bed and lies down, then taking her pillow, she uses it to prop up her head, so that she could still get a good view of Tommy. “Ok, I’m ready, come lie on me so that you head is lined up with my breast.”

Tommy had never been on top of a girl before, he felt his cock throbbed in anticipation. Slowly he positions himself over her, propping himself up by his arms, afraid to come on down for fear of crushing her.

Taking her hands she grabs his head, and pulling him down the rest of the way, saying with more than a little impatience, “Come on, Tommy.” Forcing him to press his weight on top of her. His head ended up being sandwiched between her two breasts. Tommy was just content to stay there. He could feel her left breast which was pressed against his nose and mouth, while her right breast was pressing the back of his head. And with his ear now pressed into her chest, he could even hear the beating of her heart, that seemed to be beating a little faster than normal.

“Go on now. Show them how much you like them. Kiss them.” She instructs.

He starts kissing the side of the breast his mouth was pressed against and then lifts his head some. Turning his neck around, and propping himself up by his forearms, he started to continue his kissing on the underside of the breast and then moves on up toward the side facing the outside of the bed. Emily just lies back, enjoying the boy’s pattering of kisses all around her breast. She could tell Tommy was getting more adventurous as he had started to move his kisses toward its peak. Slowly kissing around the areola and then finally giving the protruding nipple a light kiss.

Emily, yearning for more, grabs the back of his head and said, “Go on, Place your mouth over it.” Still pulling his head in. “And suck it, as if you were still a little baby.”

So Tommy does so. Opening his mouth, he engulfs as much of the breast as he can and starts sucking it further into his mouth. He couldn’t believe he was actually doing this, something he had only dreamed of doing was actually coming true.

“Stimulate the nipple with you tongue, now.”

Tommy, still sucking the breast into his mouth, starts to rub the tip of her nipple with his tongue. Back and forth it went across the tip, back and forth. “Oh yeah, that’s it.” Emily groans out. “That feels real good.” And it did feel good. It felt so good to have a mouth on her breast once again. “Tommy!” She says in a pouty voice. “Don’t forget the other one. She feels left out.” She then reaches out and grabs his left earlobe pulling it toward her other breast.

Tommy consents and starts to work on the right breast now, covering the areola and nipple with his mouth, he licks his broad tongue up and down on the nipple, while at the same time he reaches up with his right hand and starts to softly pinch the left nipple that was now all slick with his slavia.

Emily found herself slipping more and more into a dreamland state, as the young boy continues to please her and her two breasts, and finds herself saying, “Yes, that’s the way Tommy. Keep the other one company while your mouth and tongue stimulates this one.”