The Lessons Ch. 10

Teddy did not find this to be particularly compelling, as Miss Harding had done precisely the same thing to him. In fact, under the pretense of needing to get a better grip of her butt cheeks, he slip his right hand down to the bottom part of her left cheek, thereby allowing the tip of his fingers to touch the lips of her pussy. His cock swelled with the contact. She felt so soft there, so intimate, and, he was excited to notice, she was quite wet.

Miss Harding raised her head in surprise with the touch, uncertain what to say. This was what she had been hoping for. She thought of turning to look at Teddy, to give him a smile of encouragement but she knew that Penny would notice. She instead just pushed her cunt harder into his fingers.

Teddy noticed the subtle movement and responded by lightly stroking the mound of her cunt, feeling the folds of her lips. He pressed his erection into her thigh. Miss Harding put her head down into the desk and smiled.

Penny saw where Teddy had placed his hand. However, she was not upset. She knew it was unrealistic to expect Teddy not to get excited by the sight of the naked Miss Harding. She was a very pretty and attractive woman, and she knew Miss Harding was a fantasy for many of the boys. As long as he did not get carried away with his actions, she would not be offended. In fact, she found this to be a nice present for Teddy. She was giving him Miss Harding as a toy for him to play with. What better present could he receive after Miss Harding had humiliated him in a comparable manner in front of the class. Besides, she was there to be sure that it did not go too far and to maintain the emphasis on humiliation and punishment.

Penny then placed the tapered end of the pole at the entrance to her asshole. Miss Harding's smile turned to an anticipatory grimace. She squeezed her butt shut.

Teddy felt the increased tension in the muscles of her cheeks as she tried to deny entry, and he smiled at the sight of her anus pinching shut, like a stubborn child who is trying to defy the inevitable.

"Miss Harding," Penny spoke, "the more you fight it, the harder it will be for you and the longer this will last. It's really up to you."

Miss Harding sighed. Teddy tried to encourage her by caressing the lips of her cunt, sliding his fingers along the folds and flaps of her wet lips. Miss Harding sighed again, this time with pleasure. She put her head down and relaxed her anus. Teddy could see the loss of tension. He nodded to Penny, who then pushed with the pole. It moved in about an inch.

Miss Harding scowled. It wasn't so much painful as it was very, very uncomfortable; like a hard and big turd trying to get in. It was tough enough trying to get them out; letting one in was extremely difficult. It just wasn't natural. She felt herself tensing up again, squeezing down on the pole. She tried to relax. She even lifted up on her heels to push her butt up higher, trying to make it easier for Penny to insert the flag.

Penny grunted as she pushed in a bit harder, shoving the flag pole in about 2-3 inches. She was pleased that it had gone in this far, but it didn't seem to be far enough. It wasn't the effect she wanted. She wondered what to do.

Teddy, on the other hand, was pleased. He found the sight of Miss Harding's distended asshole to be very erotic. He had a front seat in watching Miss Harding having to take something too big up her ass. She was an authority in their day-to-day lives, and a very attractive one at that, but now he had her butt cheeks spread open to watch her struggle to receive a flag pole stuffed up her butt. His only regret was that it was not his own cock.

It was Miss Harding's regret as well. She would not have minded having Teddy fuck her up the butt. She had never had anal sex before. She had made Ronnie lick there. She had stuck her finger up there to excite a man. Some guys had even used their fingers on her anus before. But never a erect cock. She thought it would be exciting but she was afraid of being hurt. Teddy, however, was probably too small to hurt her and she could have stopped him at any time. This was one reason she liked experimenting with the boys of the college. She was the one in charge, she could try new things without any lasting repercussions, and she could end it at any time. But, the presence of Penny was altering the whole experience. Rather than being the one in charge, she was the one being controlled, and in a very degrading manner.

Nevertheless, with Teddy playing tenderly with her cunt she was maintaining a sexual arousal, and being the one submitting was also strangely pleasurable. If only Penny would not require that she be so blatantly debased.

Penny came to a conclusion. She pulled the flag back out, much to the relief of Miss Harding. Teddy was disappointed, as it hadn't been in very long. However, the sight that greeted him with the removal of the pole was a pleasant surprise. After it was removed, Miss Harding's anus continued to gape wide open. He thought he might even be able to stick a few fingers in without touching skin. It was curiously appealing, like she was finally capitulating, figuratively and concretely opening herself up to him. But, then, it slowly squeezed shut, like the lens of a large camara.

"Miss Harding," Penny ordered, "get up onto your desk, on your hands and knees."

Miss Harding was hoping that it would now be largely over; that the removal of the flag pole was the end. She looked back at Penny, giving her a pleading expression of surrender. She didn't want anymore. "Wasn't that enough?" she asked.

"Just a bit more, Miss Harding, and you will be done." Penny still held the flag in her hands.

Teddy let go of her butt cheeks and moved back. Miss Harding slowly stood up. She was glad to be able to stretch her back. She looked at Teddy, hoping that he would intercede on her behalf. Teddy, however, had his eyes on her wet cunt and wasn't paying much attention to her discomfort. Miss Harding sighed. She stepped out of her panties and climbed onto the desk, posing like a dog on her hands and knees.

Teddy had a big grin. Miss Harding's bottom was now much higher, providing him with an excellent view. Her butt was too high for him to fuck her, but he wouldn't mind using his fingers, and even his face. He turned to Penny to learn what she had in mind.

"Miss Harding, keep you butt up in the air and put your head down on the desk. In fact, push your ass up as high as it will go."

Miss Harding complied. This posture was even more revealing than earlier. However, she hoped that at least the task would be more sexual. She knew that Teddy now had a very good view of her cunt, which she also knew was quite wet with arousal. She wanted to ask him to use his mouth on her, maybe even to have sex with her. Maybe Penny would consider that to be degrading. If Penny thought that she would hate it, maybe she would make Teddy fuck her.

"Please, Penny, this is so embarrassing for me. You're not going to make me have sex are you? You're not going to let Teddy do things to me, are you?"

Teddy quickly turned to Penny, hoping that this was indeed her intention. Penny, however, was not so easily fooled. She knew that Miss Harding would enjoy having sex with Teddy. That would not be a punishment.

"Maybe I will." She paused, knowing that Miss Harding was waiting for the instruction. "Spread your cheeks with your hands, Miss Harding."

Miss Harding complied. She got a good grip on both cheeks and spread them wide, opening to full view her asshole and cunt. She didn't mind. She thought that perhaps she had fooled Penny, and she liked showing off to Teddy. She knew that he was dying to have sex with her. She was in a very servile and shameful posture, but if that was what was necessary, she would grovel. She would pose like a bitch dog, presenting herself for sex.

Penny, however, did not have that in mind. She walked up behind Miss Harding and with one smooth movement shoved the flag pole back down into her rear. Miss Harding's head shot up in shock and pain. She let go of her ass and grabbed the desk to keep from falling over. Penny grunted and groaned, straining to plant the flag in her ass, as Miss Harding grunted and groaned as well, straining to receive it.

"Penny, please, it's just too big." She panted, shifted her weight, offering her butt up higher, trying to relax her asshole. "I already did this; unh, my, oh my, it's so big."

"Just about, Miss Harding," Penny replied. It was like she was trying to plant the flag in hard dirt that just wouldn't accept it. However, with one last hard shove, she believed that she had gotten enough in. She let go and stepped back.

The effect was good. Miss Harding was kneeling on her desk, her butt raised high in the air, with an American flag planted in her ass. The pole was a bit precarious, but it was staying put. Her efforts to get comfortable were also having the effect of even appearing to be waving it.

"Don't let it go, Miss Harding," Penny commanded. "You know that you can't let the flag touch the floor. So, keep a good grip on the pole."

Miss Harding did clamp down hard on the pole, but also covered her face in shame. It was so agonizing to have the pole shoved up her butt, but even worse to be so humiliated in this manner by Penny. "Why must you treat me like this," she pleaded.

"You know full well, Miss Harding," Penny replied. "Now wave that flag for us with your fat ass." Miss Harding acquiesced. Moving her butt back and forth, waving the flag in the air with her hips. Penny couldn't suppress her laughter. Teddy also had to smile, but didn't laugh out loud, feeling more sympathetic with Miss Harding's embarrassing predicament and, frankly, he did not consider her ass to be fat. It was considerably bigger than Penny's, but not at all chubby. It had a nice, firm shape, and very appealing with a pole lodged down into the crack, the flag waving in the air as she provocatively circled her ass.

"Teddy," Penny thought out loud, "I wonder if we should take a picture of this. Don't you think this would be a good picture for the school yearbook?" Teddy had to laugh at that.

Miss Harding, however, again raised her head in shock, almost dropping the flag to the floor.

"Watch it Miss Harding!" Penny warned. "You can't let it touch the floor."

Miss Harding quickly resumed her abject position but protested, "No, that is going much too far. I will not submit to that. This exercise begins and ends in this room. That is our understanding."

Penny fully agreed, but she wanted Miss Harding to feel under her thumb. "Well, I will agree to that, but you have to agree to one last exercise."

Miss Harding sighed. She couldn't imagine anything worse than a flag up her ass, but she had to decide soon. She didn't think she could hold it in much longer. She felt like she had to take the biggest dump of her life or, more accurately, like she was half way through her biggest dump in her life and couldn't finish the job. "Yes, fine, I agree," she acquiesced.

"Excellent," Penny replied. "Actually, it isn't even anything new. I want you to provide the specimen."

There was silence as Miss Harding thought it over. Peeing in front of two students would be humiliating, but, frankly, less shameful than her current posture, and all the forcing in and out of her ass, clenching and relaxing her sphincter, had also had been providing indirect stimulation of her bladder. "Yes," she reluctantly obeyed, "I will provide a specimen, but that has to be it."

Penny didn't consider Miss Harding to be in any position to be making demands, but she carefully removed the flag. Teddy again enjoyed the sight of her asshole gaping open for awhile after the pole was removed.

Miss Harding breathed a tremendous sigh of relief with the removal of the flag. She brought her hand back and massaged her cheeks, trying to ease the discomfort. She even briefly felt her anus, wondering if any damage had been done. It felt sore, but no stinging or painful sensations that suggested any real harm.

"Are you concerned we injured you, Miss Harding?" Penny asked.

"Well, frankly, yes," she admitted, hoping that Penny was beginning to have second thoughts.

"Teddy, why don't you take a look to see if she is ok."

"Sure," Teddy quickly replied, although worried that he had probably revealed too much enthusiasm.

Penny, however, was not troubled. She accepted that Teddy would find a lot of this to be arousing. As long as it was within her control, she didn't mind. She also thought that Miss Harding would find such an inspection to be embarrassing and, an examination was an appropriate complement to Miss Harding's use of Teddy in class.

Miss Harding spread her cheeks for Teddy. A broad smile crossed her lips and she buried her face in the desk so that Penny would not notice.

Teddy felt like a boy at a candy store. His face was now just inches from her asshole, and he gleefully explored with his index finger the crack of her rump and the puckered lips of her asshole. He pretended to be looking for abrasions or lesions, but he was instead just enjoying the sensation of exploring and feeling the crevices and nether hole of Miss Harding's rear end.

He even looked in close at her asshole, exploring how difficult it would be to get his finger inside. He was surprised that there was any resistance, given what had just been there seconds before. Miss Harding, however, relaxed her anus and let him in, giving him a brief, quiet sight of pleasure as his finger slipped through her sphincter. Teddy wiggled his finger around in her butt, enjoying the tight grip of her anus. It was like it was caught in one of these "Chinese" finger traps. Miss Harding playfully relaxed and tensed her sphincter, encouraging him to continue his salacious exploration.

During this time Penny was returning the flag to the stand by the door. When she turned around, she could see Teddy amusing himself. She didn't intervene. She figured that he deserved as much entertainment with Miss Harding's body as he wanted. She did not feel threatened by it. She knew that Teddy was her man, and that he would only be grateful to her for being able to use Miss Harding as Miss Harding had used him. This would go far in helping him overcome his humiliation.

Teddy turned so that Penny could not see precisely what he was doing. He used his other hand to explore her cunt. Miss Harding openly gasped, and spread her legs farther to give him more room. She was very moist and Teddy had no difficulty sliding his finger down into this smaller crack. He noticed how much more fleshy were Miss Harding's lips. She even seemed to have flaps hanging out from her slit. He explored up and down the slit until he found her hole, and then slowly circled, screwing his finger into her cunt, using his thumb to rub and pressure her clit, still keeping the finger of his other hand deep in her ass.

Miss Harding gripped the desk with her hands. "Teddy, this is so embarrassing, don't do such things to me."

Teddy stopped, feeling that he had been caught with his finger in the cookie jar. Penny, however, did not object. In fact, she said, "You let him do whatever he wants, Miss Harding."

Miss Harding smiled. This was the punishment that she had wanted. She continued to feign protest, believing that her expressions of humiliation would have the effect of Penny letting it escalate. "It's not right. You shouldn't do that, you know you shouldn't do that" her voice weak and her breath panting. "This is so wrong," she sighed, as she began to slowly circle and nudge her posterior to complement movements of Teddy's fingers.

Teddy was enthralled with the effect he was having. He was actually making the untouchable Miss Harding excited with his touches. He felt like a sexual artist, manipulating her cunt and asshole with his fingers; her most personal parts displayed just inches from his face. She was literally bent to his will, and he was taking full advantage. Exploring a woman's full cunt, making her squirm with pleasure, plunging his young fingers in and out of her sloppy wet cunt. Even the sounds were arousing: the squishing and slurping of his fingers sliding in and around her cunt.

Miss Harding knew that the sounds were obscene, and that her own behavior was obscene. Her butt was raised in the air, wiggling around with the ministrations of the fingers of one of her students. She could never deliver another lecture to Teddy without blushing. Imagine what he will think when she bends over in front of him to pick up an eraser. But, she wasn't going to think about that now. Now, she only wanted to enjoy his fingers, obtain relief, and end the humiliation. She began to openly thrust and pound her rear end on his finger.

Teddy's eyes widened in surprise and shock at her wanton abandonment. He never thought a grown woman, and certainly not a teacher, could be so crude and indecent. He so wished that they really did have a camera. He wanted this to stay in his memory for years. He shoved in three fingers of his hand into her cunt. He could barely fit just one in the cunnie of Penny. He was literally fucking the cunt of Miss Harding with three fingers, moving them around and around, screwing them as well as plunging them deep inside, still keeping a finger of the other hand well embedded inside her ass, moving it in and out as well, grinning all the time, feeling his cock straining in his pants, wanting so much to release it and plunge it alternately into both holes.

"Teddy, please, oh my," Miss Harding exclaimed loudly, raising her head in a growing level of excitement, holding strongly onto the edges of the desk in an open display of sexual excitement, her ass jutting out in wanton arousal and desire. This was enough for Penny.

"That's it, Teddy. I think she's ready."

Teddy stopped and looked back at Penny, keeping his fingers inserted.

Miss Harding groaned in disappointment and frustration. She kept her hips moving on his fingers, but this just had the effect of moving his hands around rather than getting him to continue.

"Let her go, Teddy." He reluctantly withdrew his fingers. The fingers being removed from her cunt made a slurping noise; the finger of his other hand made a popping sound as he plucked it out of her asshole.

"Get off the desk, Miss Harding, and provide us your specimen."

Miss Harding crawled off the table, feeling sweaty and exhausted with her sexual excitement, and a bit embarrassed to have behaved so much like a slut in front of the two of them. She kept her head down and moved to the beaker. She squatted down on the jar, spreading her legs wide for each of them to see. She now indeed felt like a cheap slut.

"Wait for my command, Miss Harding," Penny commanded.

Miss Harding looked up at Penny, worrying that there might be something even more to this task. Her current deportment was explicitly shameful, squatting down on the floor, wearing only a bra, her legs wide open, her cunt gaping open, exposed, and clearly very wet from Teddy's manipulations; and, she was about to pee in front of two of her students; what could be more shameful?

"I believe that you have inadvertently aroused my boyfriend, Miss Harding. He is not usually aroused by old women, but I suppose that any boy would become excited by your obscene display. I believe he needs relief and it is only appropriate that you should receive it." Penny walked up to Miss Harding and motioned Teddy to join her.

When Teddy stood beside her, Penny instructed him to take out his penis. He was very glad to do so. He had been feeling desperate to get relief and it was apparent to him now that he would. He proudly removed his stiff, hard cock from its confinement. It was so nice to get it out in the air, now poking directly at the face of Miss Harding.