Big Bang Theory - Penny Tutors Sheldon

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Penny helps Sheldon prepare for Amy.
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Part 35 of the 51 part series

Updated 08/17/2020
Created 01/23/2015
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shaggy77
shaggy77
594 Followers

Fictional story about fictional characters.

*****

After a short but tortuous separation, Sheldon Cooper had realized how much he valued the companionship of Amy Farrah Fowler, and they had gotten back together. Not one to dwell on the past, now the only focus in his life was securing opening-night tickets for the latest, much anticipated, Star Wars film. Joined by the remaining members of the "Four Nerds;" his roommate Leonard Hofstadter, Rajesh (Raj) Koothrappali, and Howard Wolowitz; they were all "on line" with a separate device trying desperately to reserve tickets the moment they went on sale. Sheldon, Leonard, and Raj all held doctorates and Howard was a noted aerospace engineer, but they were all reduced to childhood by their love for science fiction, and Star Wars in particular. Sheldon was nearly reduced to praying, something that was abhorrent to his scientific mind, when Howard finally managed to obtain the coveted tickets.

Later that day, Leonard's new bride and longtime neighbor Penny, reminded Sheldon that the Star Wars premiere was on the same night as Amy's birthday and that since they had only recently reunited it might not be a good idea to abandon her on her special night. Still totally clueless concerning human interaction, the Hofstadters had to explain to him how Amy would feel emotionally if it appeared Star Wars was more important to Sheldon than his girlfriend. Trusting their instincts, Sheldon had finally acquiesced and agreed to spend the evening with Amy.

The next day Penny was entertaining her best friend Bernadette (Howard's cute wife) when they heard the familiar annoying knock on Penny's door: knock, knock, knock, "Penny;" knock, knock, knock, "Penny;" knock, knock, knock, "Penny" and knew immediately it was Sheldon.

After toying with him momentarily, Sheldon entered Penny's apartment and without any preliminaries requested their opinion on his birthday gift for Amy. He gave them three choices, the first two being typically Sheldon: activities that were neither terribly personal, nor did they directly involve them as a couple. When they were rejected by Penny and Bernadette, Sheldon offhandedly stated that he guessed they could have coitus. The girls' jaws dropped open and Penny accidentally snapped the stem on her wine glass. Penny inquired, "that's a pretty big step for you Sheldon, are you sure?"

"Yes, I really want to show Amy how much she means to me," Sheldon replied. After both girls agreed that Amy had been looking forward to this gift for years, Sheldon stated, "well then it's settled, Amy's birthday present will be my genitals." Without further reflection or comment, he left the apartment.

That night the spirit of Professor Proton, dressed as Obi Wan Kenobi, visited Sheldon in his dreams and asked Sheldon, "what seems to be bothering you; these visits seem to be out of my control."

"Well hello Professor Proton," Sheldon greeted his favorite childhood TV star, "yes, you seem to only appear to me when I am struggling with a dilemma. You see I have decided to become intimate with my girlfriend, Amy Farrah Fowler, and now I am unsure how to proceed. I have never been very skilled at personal intimacy and I don't want Amy to be disappointed. Do you have any advice?"

"Oh, is Amy that hot blond I have seen in the apartment," Professor Proton excitedly inquired.

"No, that would be Leonard's wife Penny," Sheldon answered, "Amy Farrah Fowler is a respected neuroscientist."

"Oh right, just my luck...why can't I appear in her dreams," Professor Proton said, sitting on the edge of Sheldon's bed, "well, I know this would be a novel approach for you, but have you considered having someone more knowledgeable in this area tutor you?"

Sheldon thought momentarily and replied, "you are correct that it is extremely unusual for someone to be more knowledgeable than I, but I think your suggestion is valid. Thank you, you may go now."

Shaking his head as he faded, Professor Proton muttered, "if only it were up to me."

The next afternoon as Penny was practicing yoga in her apartment, she heard: knock, knock, knock, "Penny;" knock, knock, knock, "Penny;" knock, knock, knock, "Penny."

"Come in Sheldon," she granted him entrance and Sheldon came through the door with a worried expression on his face. "What can I do for you Sheldon," Penny asked, sitting on the floor.

"Well, I see you're performing some sort of ritual, so I will be direct," Sheldon answered. "You will remember that I have decided to become intimate with Amy on her birthday. The dilemma I have is that you may not realize it, but I am not exceptionally skilled at intimate contact. Truthfully, I am having some anxiety that I will be overwhelmed at the experience, and may actually disappoint Amy on her birthday. That would not be optimal."

"You're right," Penny admitted, rolling her eyes, "that does shock me. But what does this have to do with me?"

"I'm glad you asked," Sheldon continued, "you see I have been advised by a very reliable source that I should seek tutoring in this regard. Do you remember when I paid you $ 40 to give me acting lessons as a way to improve my teaching skills?"

"Yyyeeesss," Penny slowly responded, "where are you going with this?"

"Well," Sheldon told her, "I tried to think of someone I knew who had the most experience in this field, and of course I immediately thought of you."

"Let me see if I've got this straight," Penny indignantly replied, "are you suggesting that I give you love-lessons?"

"I would compensate you most handsomely," Sheldon suggested, "and I am not suggesting that we become emotionally attached; just clinical techniques. Well, what do you say? Amy is your friend also, and I'm sure you would like her to be pleased."

Initially offended by his inference of her vast sexual experience, Penny knew that Amy had been anticipating this encounter for nearly six years, and Sheldon was right: she didn't want Amy to be disappointed. Penny surprised herself by actually considering Sheldon's proposition.

"You realize what you're asking? If we do this, it will involve intimate contact and nudity between us," she inquired.

"Of course I have examined every aspect of my request. Have you ever known me to be anything but thorough? If you will recall, I have already seen you unclothed when you fell in the bathtub. I am prepared for the consequences, no matter how painful or distasteful," Sheldon replied.

"Well, thanks for that...you old smooth-talker. You sure know how to flatter a girl," Penny sarcastically answered.

"I will need your answer forthwith as Amy's birthday is in four days," Sheldon declared, "and if you respond in the negative, I will proceed to option number two: Bernadette."

"Aren't you concerned that if we do this, I may be the first woman you will have sex with and not Amy," Penny quizzed him.

"Oh, Penny, Penny, Penny," Sheldon scolded her, "are you not aware that in this society a man's first-time is not held in high regard...it is indeed considered trivial; and there is no physical proof as to a man's virginity. My only concern is that Amy's first-time be memorable in a positive way. Now I must have your answer."

"Sheldon, that is my only concern too, however I do have two conditions: one is that this will remain eternally confidential between us; and two is that since you are availing of my so-called experience, you will never again cast aspersions on my morals or sexual history," Penny demanded.

"I accept your conditions," Sheldon promptly agreed, "now when shall we begin."

It was agreed that they would start the tutorial the next afternoon in Penny's apartment. Normally, if Sheldon was home, so was Leonard, but luckily the timing was perfect. Leonard was working with Raj after work every day on a project involving the method and contents of a message to communicate with possible intelligent life in space. Sheldon could leave CalTech early each day and Leonard would never even know. They weren't concerned with being discovered because Leonard called Penny every day on the way home to see if there was anything she needed. Penny loved him for that; he was indeed the most thoughtful man she had ever known.

Another stroke of good luck was that Howard and Bernadette were currently preoccupied with the task of refurnishing their home, now that Howard had finally agreed to part with some of his late-mother's furniture. Amy had immersed herself in a new experiment involving Capuchin monkeys and had very little free time. Bernadette and Penny had informed her of Sheldon's intentions, and Amy was attempting to calm her excitement by preoccupying herself with work. They had even persuaded her to have a "bikini wax."

Before Sheldon's arrival the next day, Penny made sure to shower thoroughly and moisturize her skin in preparation for their encounter. She was well aware of Sheldon's fixation on personal hygiene and wanted to make sure he felt as comfortable as possible touching her body and having her touch his. To mask her guilt at touching another man, she fortified herself with a couple tequilas and persuaded herself that Leonard would want her to help their friends Amy and Sheldon. "Oh you lucky dog Sheldon," Penny spoke aloud as she gazed at her nude reflection in the mirror, downing another shot.

Her body was exquisite: her breasts a perfect 36 C with just a hint of sag, capped by large pink areola and gumdrop sized nipples. Her creamy skin, soft and smooth as she ran her hand down over her taut belly to her completely bald pubic area. She smiled as she thought of how much this turned Leonard on. Her mound was prominent with swollen puffy lips making for a perfect "camel toe." Turning, she admired her firm absolutely round ass cheeks above long, shapely legs. Suddenly she realized she was becoming aroused at the prospect of her imminent sexual encounter with Sheldon. "Must be the tequila," she mused, "I certainly don't find Sheldon attractive."

Trying her best to mimic the picture of Amy and Sheldon's encounter that she had envisioned, Penny put on the most plain pair of panties she could find (although they were still quite sexy): a silky pair of light blue bikinis and the most "frumpy" nightgown in her drawer: the matching silky nightgown that reached her knees. "At least they're not see-through," she reasoned, noting that she still looked incredible as her nipples poked against the silky material as it caressed them. Throwing on an old flannel robe, she straightened the bed covers because, "this is Sheldon we're entertaining," she thought.

Knock, knock, knock, "Penny;" knock, knock, knock, "Penny;" knock, knock, knock, "Penny," she heard and rushed out to the living room to greet her pupil.

Opening her door, there stood Sheldon dressed in trousers and a "Flash" t-shirt. "I didn't know what I should wear," he announced as he entered.

"That's fine," Penny assured him, "now before we get started let's get something straight: I am the teacher and you are the pupil. You must agree to put yourself in my hands, both literally and figuratively, with no reservations or hesitation. Hey, I used the word literally correctly."

"Congratulations," Sheldon countered in his deadpan style, and "agreed."

"OK, since I can't imagine either one of you going berserk with passion and ripping each others clothes off, I am guessing that you will probably agree to get undressed and get into bed together," Penny stated.

"Fair assumption," Sheldon agreed.

"So let's go into the bedroom," Penny suggested, "and yes I showered and put clean linen on the bed." When they reached the bedroom, Penny shed her bathrobe, threw it on a chair and urged Sheldon, "why don't you get undressed down to your underwear and join me in bed."

"Fine," Sheldon replied as he began to undress; neatly folding his trousers and shirt and carefully placing them on her chair. As she climbed under the covers, Penny noticed that Sheldon's "tighty-whities" were quite baggy, not "tighty " at all; like they were two sizes too large. He crawled under the covers wearing his plain white underwear and undershirt.

"OK, today's lesson will be on foreplay. This should be very important since it is Amy's first time. You know about foreplay, right? You two have kissed," Penny inquired.

"Oh for goodness sake," Sheldon replied disgustingly, "of course we have kissed; at least a half dozen times. I am familiar with the courtship liturgy: kissing, foreplay, coitus."

"Oh how romantic," Penny sighed, "I am going to demonstrate some advanced kissing techniques. You understand why it is necessary for Amy to become aroused, right."

"Yes, yes...arousal...secretions...lubrication. I can read you know," Sheldon scolded.

"Just one more thing Sheldon," Penny added sarcastically, "during our lessons, the less you talk...the better." Before he could respond, Penny grabbed his head between her hands and planted her lips on his, mumbling, "just follow my lead." She began to kiss him passionately, grinding her lips into his and eventually beginning to probe his mouth with her tongue. When he failed to reciprocate she released him and instructed, "I said follow my lead...and don't worry, I have a new, unopened bottle of your favorite mouthwash in the bathroom. Now let's try again, and this time loosen up."

"Have you been drinking," Sheldon inquired, "I taste alcohol."

"Oh sweetie, do you even have to ask," Penny answered.

After several attempts, Sheldon finally began to respond and when Penny closed her eyes she actually began to enjoy "making out" with Sheldon. "One thing Sheldon," Penny suggested, "I know I have always preferred it when the man closes his eyes while kissing...Amy may also."

"Funny you should mention that," Sheldon responded, "Amy actually suggested the same thing. I shall attempt to remember that technique...although it makes me feel vulnerable."

"Try not to think of kissing as a technique," Penny suggested, "try to just go with the flow.

Now I'm going to remove your t-shirt and you will caress my shoulders and remove my nightgown in a similar manner." As he sat perfectly straight, Penny lifted his t-shirt up over his head and carefully tossed it on the foot of the bed. She could tell he was distracted by the presence of the un-folded shirt and directed him, "go with the flow...don't ruin the moment with your obsessions...now you may reciprocate and remove mine."

Penny raised her arms over her head and Sheldon, surprisingly gently, grasped her shoulder straps and pulled her silky nightgown up and off. Mimicking her motion, he tossed it onto the bed at their feet. Noticing that Sheldon was staring at her (seemingly) perfect, naked breasts, Penny spoke up, "you know it's not polite to stare...but what are you thinking?"

"They're asymmetrical you know," he stated matter-of-factly, "the left areola is slightly more elliptical than the right."

"That's the first complaint I've gotten," Penny stated, twisting her torso from side to side causing her wonderful breasts to wobble, "these puppies have gotten me a lot of free drinks. Now remember what I said about ruining the moment. When you first see Amy's breasts, make sure you praise them...not find flaws. She is very insecure about her attractiveness and you need to reassure her."

"Sorry, not complaining, merely making an observation," Sheldon apologized.

Penny took Sheldon's hands in hers and placed them on her warm, soft breasts. "You need to caress them softly...even kiss them," she instructed, "all in the name of foreplay."

She began to rub his nearly hairless chest, hoping he would respond in kind...and he did.

He ran his baby-soft hands all around her beautiful tits, massaging them and weighing them...bouncing them in his hands. He held them in his hands like grapefruit and ran his thumbs over her now erect nipples. Penny was relieved because she had half expected him to show up wearing latex gloves. He seemed to be mesmerized by her gorgeous tits and she asked what he was thinking.

"They are strangely pleasing," Sheldon admitted, "remarkable in their smoothness and texture...like those anti-stress balls filled with gel. I think I am beginning to see why men find them so irresistible...besides the Oedipal connotation, of course."

"Oh you sweet talker," Penny answered, "now try to squeeze them, kiss them and focus on the nipples...again, I assure you they are clean."

Not bothering to verbally respond, Sheldon pressed her breasts together, squeezing them into one mound of flesh; then beginning to knead them like bread dough. Penny had stopped caressing Sheldon's shoulders and chest and just sat back to enjoy his attention. He leaned forward, stuck out his tongue and reluctantly licked her left areola like an ice cream cone. After repeating this several times, he duplicated the technique on the right (the more round one) and then, without direction, he took her pink gumdrop between his teeth and nibbled. Penny's body shivered at his stimulation and she felt her crotch growing involuntarily moist. "Oh shit Sheldon," she groaned, "that is very good...Amy will enjoy that."

"I must say Penny," Sheldon confessed, "I do like the scent of your body wash; and the more I contact your breasts, the more I seem to enjoy it. Judging by your breathing pattern, I would say that all that is written about the foreplay-ritual is correct."

"I think you have pretty much mastered the breast aspect of foreplay," Penny declared, "are you ready for the next step: hand to genitals contact?"

She could swear he was reluctant to release her breasts, but he dropped his hands and agreed, "if we must...I do want to please Amy."

"OK then," Penny continued, "just so as not to shock or surprise you; I am going to caress your tummy and work my way down to your groin...when I'm done, you will do the same to me. When you are with Amy, this should be done together, but for now I just want to show you the progression." Penny leaned into Sheldon and started to run her soft hands along his midriff. This area was still under the covers and when she slid her hand inside his underpants she received the shock of her life. When her hand made contact with his penis, she discovered the most enormous hunk of flaccid cock that she had ever felt. Now she knew why his shorts were so baggy. She tried to stifle her surprise, but couldn't as a faint gasp escaped her lips.

"What's wrong Penny," Sheldon asked, "did I do something wrong?"

"Ummm, no sweetie...it's just that...ahh, are you aware that your penis is larger than normal," Penny answered.

"Well, since I have very few, if any, intellectual peers, I guess it stands to reason that I be superior in every aspect. I am aware that my penis is at least twice the listed average size. I hope this will not be a problem," Sheldon declared.

"Not for me," Penny chuckled, "but Amy is in for a big surprise. I think it's time we shoved the covers back so we can lose our underwear."

"You are the teacher," Sheldon declared smugly as they shoved the sheet, blanket and bedspread down to the foot of the bed.

Penny kneeled between his legs and, as he lifted up to assist her, began to slide his underpants down his pasty white legs. She caught her breath when she got her first glimpse of his penis. It lay between his legs like a dormant anaconda. Still flaccid, it must have been a good nine inches and as thick as a salami. He had been circumcised and his crown was large and purple.

Seemingly in the distance, she heard Sheldon mock her, "you know it's not polite to stare."

Crawling up between his legs, Penny grasped his huge cock in both hands and began to stroke it, "I don't know if Amy will know enough to do this, but you can show her how. I assume you masturbated as a kid growing up."

"Oh goodness no," Sheldon admitted, "mother would have never permitted it...you know, a sin before God and all that rhetoric. Puberty was nothing more than an inconvenience for me. I was just receiving my Bachelor's degree when I developed pubic hair." As Penny slid her tiny hands up and down Sheldon's snake, it began to stiffen. "Oh my," Sheldon exclaimed, "I believe that is the first time that has happened; except, of course, for nocturnal penile tumescence...which is perfectly normal you know."

shaggy77
shaggy77
594 Followers