Teaching Carol - S01 E05

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Teaching Carol - S01 E05

Read Story: SEASON 1 EPISODE 5

The knock, when it came, was a timid one. Good, I thought, and called, "Come in."

'Maria' opened the door a little, stuck her head in and said, "You wanted to see me, uh, Mr. Black?"

I turned to her and said, "Ah, Miss...Santiago, is it? Yes, come in." She stepped to just inside the door. "Close the door, please." She did so and stood there clutching her purse in both hands. I was pleased—she was doing a much better job than I expected. Or else she really was afraid.

I looked directly into her eyes—or as directly as I could through her glasses—and said, "I'll come right to the point, Miss Santiago. I saw you take something from someone's desk and put it in your purse."

She made an attempt at appearing shocked. "N-no, I didn't..."

"Well, if I'm mistaken then you won't mind showing me what's in your purse."

"I...I..."

"Miss Santiago, let me put it another way. Either I'm going to look in your purse, or the police are." 'Maria' looked blank. "Your choice."

She wasn't good at improvising, obviously, so I gave her a hint by holding out my hand. She looked down and mutely handed over her purse. I opened it and pulled out the CD player. I held it up. "This is a fairly expensive machine. I believe you can go to jail for stealing something like this." I waited for her reaction but 'Maria' was still stuck—so I gave her a lead: "Aren't you even going to apologize?"

She blinked for a moment, then caught on. "...I'm sorry..."

"Sorry you got caught, maybe. Well, you're going to be sorrier..." I put the player and the purse on the floor and picked up the receiver from the telephone on her desk. I was hoping she'd jump in and try to stop me, but she still needed help. I turned to her and said, "Can you think of any reason why I shouldn't turn you over to the police?" Still blank. I made it a little more obvious: "I'd be scared if I were you—jail isn't a very nice place."

Finally she got it. "Please don't call the police...oh god, I'm sorry! Really!" It wasn't very convincing, but it was a start.

'Mr. Black' gave her another hint: "I don't believe you, Miss Santiago. You'll have to do better than that." I sat back and looked at her as if I'd gotten an idea. "You know, if you can convince me that you're really sorry...I might let you go."

She floundered, "Well, I...."

I turned back toward the phone. "But if you'd rather go to jail..." I started to dial.

Finally she woke up a little. She grabbed my shoulder. "No!" I turned back to her and waited. She went on, trying to sound convincing, "I really am sorry, Mr. Black, honest!"

I waited for more, then shook my head as if disgusted and turned back to the phone. She actually managed to sound a little panicked when she stopped me again and said, "Please, Mr. Black! I'm sorry! What can I do to convince you?"

That was what I'd been waiting for. I put down the receiver and turned back to her. I pretended to think for a moment. Then I said, "Well, for starters you could beg my forgiveness." She started to reply, but I held up my hand to stop her and continued, "...on your knees, Miss Santiago."

Her eyes went wide behind her glasses, but I think she was glad to have some direction because she immediately fell to her knees in front of me. She looked up at me, and said, "Please forgive me."

Unfortunately, she smiled as she did so—Carol wasn't staying in character. I gave her a disdainful look. "You're not taking this seriously, Miss Santiago, but I can promise you that the police will—and it makes no difference to me whether you go to jail or not. Try again."

More seriously this time, she said, "I'm really sorry I stole the CD player, Mr. Black. Please forgive me."

I pretended to consider her performance, then shook my head and said, "You're still not convincing me. You're not really sorry." I waited a beat. "Get down on your hands and knees." Slowly, she did so, still looking up at me. "I think you need a lesson in humility, Miss Santiago. I want you to crawl all the way around the room."

She looked a little shocked. "Why?"

"Because I told you to. Go on."

And after a moment, she did. The room wasn't very large, it couldn't have taken much more than thirty seconds for her to make a full circuit, but I enjoyed watching her cute little behind moving under the pleated skirt, and the way her glasses slipped down her nose.

When she returned to her starting point I told her, "Turn around." When she had done so, I reached down and lifted her skirt, pulling it up over her hips. She reacted with indignation that was only partly feigned.

"No! What are you doing?" she said, reaching back with one hand and pulling her skirt back down.

I got up and went to crouch down in front of her. I was closer to her level but she still had to look up at me from her position. "What am I doing, Miss Santiago? I'll tell you what I'm doing." I leaned closer and said, "Whatever...I...want to." I let that sink in, then continued, getting so close that our noses almost touched, "...And if you want to stay out of jail, you'll do whatever I tell you to do. Is that understood, Miss Santiago?"

It was right about here that she really seemed to begin to believe what was happening. Her eyes behind her glasses took on that same glazed, deer-in-the-headlights look that I'd seen before, and she hardly seemed to be breathing. After a long moment, her mouth opened slightly and she whispered, "Yes, Mr. Black."

"Yes...what?"

"Yes, I...I'll...do...whatever you tell me."

I kept my face right where it was and said, "Good. Now put your skirt back the way it was." And I waited while she reached back with one hand, and then the other, to pull her skirt back up over her hips. Then I stood and returned to my chair. I sat and looked at her for a few minutes, letting the silence and the fact that she couldn't see me unnerve her a little more.

Then I said, "Do you know, Miss Santiago, I really dislike pantyhose. I don't like the way they look and I don't like the way they feel to the touch. I think you should apologize for wearing them."

After a moment, she spoke, quietly. "I'm sorry for wearing pantyhose, Mr. Black."

"Take them off."

She had been expecting that, obviously, and began rising to her knees in preparatory to standing up.

"Did I tell you to stand up, Miss Santiago?"

She turned and looked at me, flustered, and said, "No, but I..."

"Get back down." She did so. "Put your head down on the floor." She slowly lowered herself until her forehead was resting on the rug. "Now—take off your pantyhose."

It was an awkward and humiliating process. She had to rest her weight on her forehead while reaching back with both hands and up under her skirt, which had fallen down again, to pull her pantyhose off of her hips and down to her knees. Only then could she lift herself back up to her former position and reach back one arm at a time to remove her shoes and then pull her pantyhose the rest of the way off.

When they were all piled up behind her feet I said, "Pull your skirt back up." Again she reached behind her and repeated the process.. Now her cute behind in pink panties was on full display. It was very tempting—I really wanted to run my hands over it—but I was trying to keep my promise not to touch her. So I settled for telling her, "Crawl around the room again."

There was no hesitation this time. She started off in the opposite direction, giving me a nice view as she headed out. She was of course facing me this time as she completed the circuit, and it was obvious from her expression that she had almost forgotten that this was pretend. When she had returned to her original position I let her wait for a few more minutes. Then I said, "Take off your skirt."

By now she had become accustomed to doing what she was told to do. So she lowered her forehead to the rug again—losing her glasses in the process this time—and reached behind her back to unfasten and unzip her skirt before pulling it down and off in the same way as she had her pantyhose. Then she put her glasses back on. And waited.

"Now your blouse."

She reached up with one hand to begin untying the bow at her neck, but I said, "No. Leave the bow. Just your blouse."

This time she took the precaution of removing her glasses and laying them beside her before lowering her head to the rug again and reaching behind her to unfasten the three buttons at her neck. Then she eased the bow above the collar of her blouse, reached back to pull the tail of her blouse up to her shoulders, then grabbed it by the collar to pull it over her head. It snagged on the bow and she had to struggle with it for a moment, but she finally got it off. She quickly smoothed her hair, restored her glasses and returned to her position. She looked very vulnerable on her hands and knees, wearing nothing but her bra and panties and that now silly-looking bow, the rest of her clothes scattered around her on the floor.

"Put your head down on your arms, Miss Santiago." She did so, and I enjoyed looking at the swell of her buttocks as they pressed against the fabric of her panties.

"Spread your knees apart." She moved them a few inches apart. "More." She complied, giving me a full view of the bulge between her legs. I looked more closely, and saw a darker spot there. Moisture. Ah-ha, I thought—I was right. Now let's see how far we can take it.

"Now, Miss Santiago, I want you to reach back between your legs with your right hand." She raised her head slightly and did as I'd asked, letting her hand rest palm up on the floor between her ankles. "And now, Miss Santiago, I want you to reach up with your middle finger...and touch yourself."

She jerked her head from her arm to look back at me and gasped, "Jon—I mean, Mr. Black! I..."

"Head down, Miss Santiago," I told her firmly. I watched as she fought with herself briefly...then slowly lowered her head again. Her right hand still rested on the floor. "I'm waiting, Miss Santiago."

This was another transition point, I knew. How completely had she surrendered her will to mine? I waited...and watched as her hand rose from the floor, even more slowly than she had lowered her head, gradually extended her middle finger...and brought the tip of it to rest precisely on the wet spot. I heard her take a sudden deep breath as she felt the moisture there, though whether of excitement or mortification or a combination of the two I didn't know—or care.

"Move your finger up and down, Miss Santiago." Slowly her hand began to move. At first it was just a slight up and down movement, just enough to show that she was following my directions. But as I watched I saw the strokes becoming longer, and that she was using more pressure. After some time she began a subtle back-and-forth rocking motion that matched the rhythm of her finger-strokes, and I heard her starting to make little noises—"Uh!...Uh!...Uh!..."—in the same rhythm. The wet spot between her legs got wetter and spread throughout the crotch of her panties.

I watched in silence as her strokes became faster, and her grunts more intense. When I judged that she was about to climax, I stepped quietly in front of her, crouched down near to where she still had her head down on her left arm, and said loudly, "Miss Santiago!"

Her head jerked up, her eyes wide and startled at seeing me so close. She was breathing heavily through her mouth, and her face and the hair around it were sweaty. I couldn't see but I was willing to bet she had quickly moved her hand from between her legs.

I gave her a moment to focus on me, then I said, "Tell me, Miss Santiago...Does it embarrass you to be down on the floor like this...in your underwear...having to touch yourself while I watch?"

Carol knew I was talking to her—that this wasn't part of the scenario—even though I was still calling her Miss Santiago. She tore her gaze away from mine and looked down. After a moment I heard her say, in what sounded almost like a moan, "Yes."

"I think you mean, 'Yes, Mr. Black."

"Yes, Mr. Black."

"And you feel...ashamed? Humiliated?"

This time her answer was barely a whisper. "Yes...Mr. Black."

"Look at me." She raised her eyes to mine, fearfully. "Now. I'm going to ask you something and I want you to tell me the truth." I paused, then, holding her gaze, said, "Do...you...like it?"

At first her eyes went wide...then they filled with tears. Her lower lip quivered. "Ohhhh!....Y-y-es!...Yes, Mr. Black!" she gasped, and quickly put her head back down on her arm and cried.

I gave her a few moments, then said, "Miss Santiago!" She raised her face to mine again, her face red and tearful. I rose and grabbed a tissue from her desk, then crouched down and gently wiped her face and held it to her nose, saying, "Blow." When she had done so I tossed it aside. Then I knelt down and kissed her gently on the lips.

Then I returned to my crouching position and said, "So, you've learned something about yourself, Miss Santiago. That's good." She continued to look up at me from her near-prostrate position on the floor, her eyes still slightly tearful. "I want to ask you something else, Miss Santiago—and how you answer is completely up to you." I leaned down until my face was again close to hers and asked softly, "Do you want to be humiliated...some more?" Then I waited.

For a moment she looked desperately into my eyes as if seeking something—an answer, permission. Then, holding my gaze, she said, "Yessss..." hissing it between her teeth.

She hadn't said 'Mr. Black' but I let it go. Instead I said, "Say it, Miss Santiago."

Her breathing began to get rough again. She licked her lips. Looked down. Looked back up at me and quickly said, "Humiliate me."

I held her gaze as I replied, "Miss Santiago. Where are your manners? Say 'Please'."

Her eyes closed for a moment, as if she were in pain. Then she opened them again. "P-please....humiliate me." She stopped, then added, "Mr. Black."

I sat back and smiled at her. "Good. Take off your bra." I waited while she put her head down and went through the necessary maneuvers. When she was done I said, "Now pull your panties down half-way and continue what you were doing."

She moaned out loud...and complied. I rose and went back to my seat to watch. The area between her legs was already slick and shiny with her moisture, and there were beads of it glistening in the small black tuft of wiry hairs that was just visible in the shadows beyond.

She was moaning and sobbing in equal measure as she fell back into the rhythm she had been using before. I waited until her middle finger—and indeed, the ones on either side of it—were covered with her moisture. Then I said, "Put it inside, Miss Santiago."

By now she was so lost in a fever of desire that she didn't hesitate even slightly; and without the smallest change in her rhythm she inserted her middle finger into her vagina and began moving it in and out. I watched as she arched her back and began thrusting her hips back and forth to meet the inward stroke of her finger. By then her moans had modulated into one long spasmodic cry. Again I waited until I was sure she was seconds away from a climax, then quickly stepped in front of her again and called out, "Miss Santiago!"

This time she gave a small scream as I snapped her out of her erotic trance. Her small breasts were heaving beneath her, their nipples erect. Her eyes as they turned up to mine were pleading, feverish. "Oh, please!...." she whimpered. "Oh....Mr. Black...please..."

I cut her off. "Not yet. If you behave yourself I'll let you finish." She stared at me. "Get up on all fours again." Slowly, she did as she'd been told, her breath still ragged, her eyes still fixed on mine. "Put your glasses back on." She did so. "Follow me." I walked slowly around the room and she crawled after me, moaning quietly, her movements hampered by the fact that her panties were still halfway down her thighs. I made her crawl all the way around the room twice.

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Teaching Carol - S01 E04

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Teaching Carol - S01 E06

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