The Lessons Ch. 06

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Penny helps Teddy at the library.
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Part 6 of the 22 part series

Updated 11/02/2022
Created 08/19/2005
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Chapter 6: Penny Helps Teddy at the Library

I want to begin by thanking all of you who provided positive feedback and supportive suggestions. I can't tell you how encouraging that was. I do want to note though that much of the next five chapters were drafted prior to the suggestions, so please don't be annoyed or disappointed if a suggested story does not appear to be among them. I liked a lot of the ideas and am working on subsequent chapters that will incorporate them. I did try to incorporate stylistic suggestions (e.g., see material from Sack's How to Blow a Man in His Underwear). Finally, yes, a few of the original chapters were not classified correctly. I do sincerely apologize. In any case, please enjoy and vote!

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After Mr. Peters' class in which the boys provided samples of sperm for Miss Harding, Penny had been wanting to get Teddy alone. She was waiting for him when he came out of Miss Harding's Human Biology class, but he was not in a good mood. Miss Harding had used the sperm samples for the class, as she had said she would, but he found the whole experience to be embarrassing and frustrating. He had been paired with Sally Embretson, who found the exercise disgusting, and when she learned that the sperm they were studying was in fact Teddy's, she almost had a fit. Miss Harding settled her down, but Sally continued to make derogatory remarks about the "quality" of his sperm throughout the rest of their laboratory assignment. They almost failed the exercise when she kept insisting that she couldn't find anything in his sperm, arguing that it must be sterile.

Penny wondered if perhaps she should just leave Teddy alone, but she walked with him down the hall as he recounted his frustration and embarrassment. She reassuringly touched his arm as they walked, trying to make him feel better. She eventually said, "I would have been happy to work with your sperm, Teddy."

He turned to her and was softened by her affectionate smile. He then recognized how whiny and complaining he had been, forgetting about the fact that there was this pretty girl walking with him, a girl that only recently had been happy to give him a hand job and had even offered to do more. He realized the pettiness and selfishness of his behavior. "I'm sorry Penny. I'm ignoring you completely, and you're being so nice. I still haven't told you how much I appreciated how swell you were when Miss Harding humiliated me in front of the whole class."

Miss Harding had indeed humiliated Teddy, and Penny tried to make him feel better. "It really wasn't so bad, Teddy. In fact, I heard some girls afterward talking about it."

"Yea, I can imagine what that was like," he said glumly, immediately switching back to his self-pity.

"What do you mean?" she feigned ignorance. She knew full well what he was thinking. Miss Harding had made a point of the fact that he had a small penis, no bigger than 5 inches perhaps when fully erect. This didn't bother Penny and she didn't want it to bother Teddy. Teddy was so humiliated by the experience though that he couldn't even get himself to explain. Penny continued, "I heard what they were saying. They were talking about how sexy you looked. They had never seen a man's erection before and they were all excited about it. Tammie even said that it looked kind of scary."

Teddy wondered if Penny was just pulling his leg. He thought though that It was possible. Miss Harding herself had said nice things toward the end, and he knew that a lot of the girls were inexperienced. He could certainly imagine the little Tammie, or perhaps Tina, being impressed, even scared perhaps. But, they all had a good opportunity to compare sizes the next day, when all of the boys' erections were on display. Penny though had been nice to keep him turned away from the other students that time, so nobody could have directly compared him to anyone else. It was then possible that some of the girls were actually impressed. He was the only boy to show off the first day, and everybody, at least in Mr. Peters' class, had to show their things the second day. He began to feel better again. He turned to Penny, "Yea, Penny, maybe you're right."

Penny smiled at her success. She liked him a lot, and wanted so much for him to feel better.

Teddy continued, "Listen, we haven't gone out for awhile, you know. I was kind of wondering, maybe, if you might want to go to the Blue Moon on Friday." The Blue Moon was a dance club.

"I would love to go with you, Teddy. I was hoping you would ask." She leaned into him with her shoulder.

Teddy reached for her hand, and she let him hold it. He felt a lot better now. He also liked Penny a lot. They had gone out a number of times, but he was always unable to openly express his feelings for her. He was just hoping that she would infer his feelings from the fact that they went out together. He had not even yet developed the nerve to kiss her. They did hold each other when they danced, but he would quickly let go when the song ended.

Penny had always wanted to do things with Teddy, sexual things, but she knew it was wrong for the girl to act first and Teddy couldn't even get himself to kiss her. She didn't know what to do to help him get the courage. One time, she had even unbuttoned her blouse all the down to the top of her bra. She didn't know what could be more obvious than that. The top of her bra was plainly visible. Teddy did steal a lot of glances but whenever she tried to get him to acknowledge where his eyes were peaking, he would just turn away and change the subject. Teddy would explain later that he just thought the open buttons were an accident and he didn't want to embarrass her by admitting that he could see some of her brassiere.

Penny began to wonder if maybe he didn't find her attractive. Maybe he didn't think she was pretty enough. Penny would not be described as a beautiful girl but she was still very attractive. She had a wholesome quality. She had long, straight blonde hair, curly bangs, pretty green eyes, smooth and pure skin, and plump, pink cheeks. She cursed the fact that the college would not let the girls wear any perfume, and at best only a little make-up. Girls like Wendy had no trouble attracting boys, with her big bosoms. Penny's breasts were somewhat on the small size. Not as small as Tina's or Tammie's, but not what one describe as full or large. Sara used her feminine wiles to get boys' attention, openly teasing them in the hallway. Penny felt that she couldn't do that, and, besides, such behavior might even scare Teddy away.

The hand job in class may have changed everything for them. She could openly play with his erection during class because Mr. Peters and Miss Harding required it. He would have gotten a bad grade if he didn't let her, and once he got used to her playing with him in that manner, she let him know that she was willing to do more; a lot more, and it was clear that he felt the same way. She was then grateful to Mr. Peters for the class exercise. She had very mixed feelings, to say the least, toward Miss Harding though, given her humiliation of Teddy.

Penny and Teddy walked down the hallway, openly and comfortably holding hands. It was now clear to anyone who looked that they were boyfriend-girlfriend.

"What about tonight, Teddy? Are you doing anything tonight?" She decided that she couldn't wait until Friday.

Teddy, however, explained that he had to work that night. It was his night to manage the reference desk at the library. His parents did not have as much money as most of the other students, and being in charge of the reference desk was one of his work study assignments. He didn't mind, as it was not particularly demanding. Very few students even seemed to use the library, partly because you could now get pretty much any reference material you wanted via the internet, and also because so many of the Templeton students didn't seem to even be that interested in their studies. He spent much of the time just catching up on his own homework.

Penny had forgotten about his work study assignment. "Oh, yeah, that's right." She was disappointed.

Teddy was also disappointed. He would so much rather spend time with her. Frankly, he wanted to do something for her to show his gratitude for how nice she had been to him the last couple of days. He was in fact planning on taking her out to dinner before the Blue Moon, an expense that wasn't that easy for him.

"Well," she suggested, "How about I come by the library and keep you company. I can bring my homework with me and we can talk, or something."

He was very happy with that idea. He wanted to let her know how he felt about her, and the library might be a good place for that. There wouldn't be a lot of pressure to have to talk all of the time. Most of the time they would be doing their homework, and when the moment was right he could tell her how he felt about her. He said, "Great, that's a great idea."

She smiled at him, and then let go of his hand to dash home to get ready. "OK, I will meet you there later." She waved goodbye as she pranced away. Teddy watched her bottom bounce as she ran off.

- - - - - - - - -

Later that evening, Teddy saw Penny walking toward him across the library. He was glad to see her. Work so far had been very boring. She waved to him as she approached. He smiled back to her. She sauntered up to the reference desk.

It was not in fact a desk. It was a three-edge, fully enclosed counter, which you entered through a swinging gate. Students were generally not allowed behind the counter. It held a considerable amount of files and documents that were only for the eyes of the administration, staff, and faculty contained within cabinets and drawers that occupied much of the space beneath the counter.

Penny leaned on the counter, smiled at him and asked, "Miss me?"

In fact, Teddy had been thinking a lot about Penny. She had been so nice to him the last few days and he really hadn't done anything in return. He had therefore stopped at a florist on the way to work and bought her a small vase of flowers. He pulled it out from beneath the counter and handed it to her: a vase of lilacs, her favorite flower (at least that is what he recalled her saying in class). Her eyes lit up, and she beamed with surprise and appreciation.

"Oh, Teddy, what a nice surprise!" He had never previously expressed much affection. This was out of character and it was even well conceived. She really did love lilacs. She smelled their sweet scent. She dashed around the counter before he could tell her that she was not allowed back there, and gave him a big hug.

He was surprised by her reaction. It was just a little vase of flowers. They weren't even particularly expensive, but she acted like it was a new car. It helped him to appreciate how important it was for her to actually hear how he felt about her. He had been assuming that she understood, but it was evident how much better she felt when he was more verbal, or, at least in this case, more demonstrative. However, he felt rather self-conscious about her embracing him like this in public.

"They're so pretty, Teddy, I love them. You're so sweet." She picked up the lilacs again and delighted in their scent. She sat down on a stool behind the counter. He decided to not make an issue of the fact that she was behind the counter. He was just glad that she was willing to share in the boredom of his job.

Penny sat on the stool and grinned at him, swinging one of her legs playfully. "Has work been real boring today, Teddy?" she asked.

"You're telling me," he replied. "I think I have had only two requests so far this evening, and I've been here for over two hours. You can see that there is hardly anybody in here." They had a good view of the main floor. The head librarian, Mrs. Baxter, was across the expansive floor, managing the periodicals. There were stacks of journals along the sides and within the ample space of the center were rows of tables for studying. Yet, there were only a few students in sight; most of the seats were empty.

Penny was now alternately swinging both legs. "Maybe my man needs some cheering up?"

Teddy liked it that she referred to him as her 'man,' and he smiled at her. "I would like anything other than this, but there is nothing one can do in a library, other than study."

Penny hopped off the stool and stood next to him. "Well, I know something I could do." She reached down and rubbed her fingers along the front of Teddy's pants.

Teddy quickly pulled away in shock. "Penny," he quietly admonished, "Not here, people can see." It was bad enough that she was behind the counter. Touching him there was clearly over the top.

Penny, however, was not to be denied. She stepped up to him again. "Oh posh, Teddy. The counter is above your waist. Nobody can see what my hand is doing," and she again stroked the front of his pants. She smiled flirtatiously at him, daring him to say no.

Penny couldn't actually feel anything through his pants, at least for awhile. Teddy was entirely limp and his little penis was well hidden beneath his slacks and briefs. However, Penny pretended that she was stroking something, not entirely sure what she was feeling, hoping that it wasn't something in his pocket.

Teddy could feel his heart racing and maybe even some sweat on his brow beginning to form. He wasn't getting excited sexually. This was just too dangerous and weird, but its weirdness and dangerousness were themselves exciting. He didn't pull away this time but he continued to argue with her. "Penny, you should stop that now, somebody is bound to see."

Penny frowned and pulled away her hand. She had noticed that he didn't seem to be getting an erection; perhaps there was no point. She returned to the stool. She kept her back turned to Teddy and bent over, placing her elbows on the stool rather than getting back on it. She turned back to Teddy and grinned, "Am I being a bad girl, Teddy? You think maybe you should spank me?"

Teddy's jaw dropped. Her pose was provocative, with her plaid skirt draping so nicely across her rear end. She was even subtly wiggling her bottom back and forth.

Penny remembered Miss Harding suggesting that Teddy liked to be spanked. She wondered if maybe he also liked spanking girls.

Teddy looked hastily around the library to see if anyone was noticing what Penny was doing. Nobody seemed to be looking. "Penny, keep your voice down. We're in a library, you know."

Penny had to admit that she probably should have spoken more quietly. She looked around the library herself, seeing whether anybody was paying any attention to them, still swinging her hips at Teddy, her plaid draped bottom waving back and forth as she surveyed the library. She reached up to the counter and brought down the first book she could find. She opened it up and pretended to read. "Nobody can see me very well at all back here," she whispered with mock annoyance to Teddy. "They can probably just barely see my head." She briefly went up on her tip toes to accentuate her upraised fanny.

Teddy had to admit that she might be right about that. The stool was well below the top of the counter, and her head just barely came over the top. Her bottom, however, was almost as high as her head. He wasn't entirely sure that nobody could see her bottom, which was being rather provocatively exhibited.

However, Penny raised the stakes by reaching back and pulling up her skirt, revealing her panties. "Penny," Teddy gasped. He looked rapidly around the room. Nobody seemed to be looking. He wasn't sure what to do. He didn't really want her to pull her skirt back down, but this seemed awfully risky to him.

Penny was holding the skirt so that much of her bottom was evident, and she was wearing really cute panties. They were pink with lettering across her bum. Written in light blue script were the words, "I'm a very naughty girl."

Teddy was both shocked and amazed. She looked back at him and smiled, again wiggling her pink bottom back and forth. "I bought these for you, Teddy, do you like them?" She had indeed bought them for him that very afternoon. She had gone to an adult novelty store, which was pretty risky for a girl from Templeton. However, she had worn a large coat and scarf, just in case she came across anybody that she knew. She found it really exciting to be wearing the panties and had been looking forward to showing them off to Teddy.

Teddy liked them a lot. Now he could feel his cock beginning to harden in his pants. He really didn't want her to pull the skirt down now. Her little derriere was so nicely wrapped by the tight pink cloth: so round, so alluring. He had never thought Penny could be so brazen. She was being a naughty girl; maybe one that deserved a little punishment. He could even see the outline of her little cunnie between her legs. He realized that he would indeed like to give her a little playful spanking; any excuse for being able to put his hand on her soft, smooth cheeks. But, she was taking such a very big chance.

"You know," she teasingly suggested, "If you come over here you can protect me from getting into any trouble. They won't be able to see if you covered me up." She gave him a little grin. She even stuck one finger in her mouth, looking flirtatiously at him in an innocent manner, yet still showing him her naughty panties. Teddy quickly walked up behind her and reached for her skirt.

"Not with that, honey." She handed him the book. "You can read the book on my bottom." She placed the open book across her lower back. He pulled it down so that it covered her exposed fanny. "You have to get closer to be able to read it," she taunted. He moved up against her. His crotch was now in contact with her soft tushy. Teddy leaned in even closer, feeling his growing erection against her cushy cheeks.

They both found it very erotic. She rubbed her fanny against him. "Teddy," she exclaimed, although quietly, "Is that your ruler in your pants, or are you also being a naughty boy?" She turned back to look at him. "You're not trying to take advantage of me, are you?" She wrinkled her brow as if she was actually offended.

Teddy was enjoying her role playing. He pushed his crotch harder into her backside, openly rubbing his erection against her supple cheeks. He even squatted a bit to try to get his erection against the mound of her cunt, although he found that this position was quite awkward. "I think it's you that is being naughty," he quietly retorted.

"Well, then," she said, "Why don't you, spank me?" She smiled and pushed back into his crotch.

Teddy stepped a bit to the side, tilted the book up slightly with his left hand, and gave her a few gentle pats on her bottom with his right hand. She giggled and said, "That's not a real spanking, Teddy. You're just playing with my bottom. Mr. Peters wouldn't do that."

He couldn't argue with that, but there was no way he could get away with a real swat in the library.

"That's ok, though, sweety, you can just play with it if you want."

Teddy did like looking at the writing across her bottom, it made her impish pose even more tempting. He looked at the sweet curves of her rump as he stroked and fondled her cheeks. Simply the fact that she was wearing such panties was enticing. He realized that apparently he didn't know her as well as he thought. Penny had tried to entice him a number of previous times but he never seemed to get the message. Now her bawdiness was written explicitly across her tush.

"A penny for your thoughts, Teddy." Penny noticed that he was deep in thought, staring at her bottom as he explored the smooth curves of her cheeks with his hand.

Teddy was unsure if he really wanted to tell her what he was thinking. What he wanted was in fact Penny. He was thinking how neat it would be to touch her between the legs, or maybe even get his hand under her panties.