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Brittany And Simon, Helping Each Other	By : WarrenConey Category: +1 through F > Alvin & The Chipmunks Views: 1515 -:- Recommendations : 0 -:- Currently Reading : 0
Disclaimer: I am not in any way affiliated with the series, ALVINNN!!! and The Chipmunks (2015). The following is a non-commissioned work, created for entertainment purposes only.

Chapter List
- 1-Brittany And Simon, Helping Each Other
- 1
[This is the sequel to, Eleanor And Alvin, Helping Each Other. All my stories are written as ‘one-shots’, so you don’t need to read anything else, to know what’s happening in them. Enjoy.]

Brittany tried to gather her wandering thoughts as she headed up the stairs of the Seville house, to the boy’s shared bedroom. She thought of her failing grade and the threat of summer school, in her very near future. She had been studying for the past two weeks, hoping to learn just enough to scrape by on her upcoming test. But after failing a practice test, her sister Jeanette had made for her, she realized that the extra studying, would not save her. Determined to avoid summer school, she came to the conclusion, that the only way she would pass her test, would be to cheat. And so she slowly walked up the stairs, trying to think up a scheme that could convince her friend Simon, to help her cheat. Coming off the stairs, she steeled her nerves, knowing the key to convincing someone to do anything underhanded, was presenting the idea with charisma.
Brittany opened the boy’s door and was caught off guard, when she found Simon was not alone, but was talking with her sister, Jeanette. She walked in, watching Simon stack a few books on his desk in front of Jeanette.
“These are the ones you wanted, right?” Simon asked, as he handed Jeanette the small stack.
“Yes.” She answered before seeing Brittany out of the corner of her eye. “Oh, Brittany, did you need something?”
“Well, I wanted to ask Simon a few quick questions.”
“What did you wanna ask him about?”
“Oh, I just wanted some, personal advice.” Brittany told her sister as she walked up to the nearby window and looked out. “Take your time, I’m in no hurry.”
“You’re not-oh, I’ll be just a moment.” Jeanette said, getting the hint that Brittany wanted to talk to Simon, alone.
“I think the last one’s in my nightstand.” Simon said walking over to the side of his bed.
“What about the one I just lent you?” Jeanette asked.
“That one’s in the bottom drawer of my desk.”
“Okay.” Jeanette said setting her books on the desk and opening the drawer.
Brittany turned from the window and watched Jeanette reach down and shuffle through the bottom drawer. Jeanette was wearing a mauve skirt today and her blue satin panties, were peeking out from underneath. Brittany looked over to check on Simon’s search. She noticed that he had found the book and was staring at Jeanette. She saw his head tilt and realized he was trying to get a good look up her skirt. The two had been dating for a while and Brittany always wondered, how far it had gone between them. She and Alvin, had gone all the way, and had become very comfortable asking each other for sex. But Simon was looking at Jeanette, as if he was trying not to get caught, peeking at his girlfriend’s behind. When Jeanette came back up, he quickly looked away and by pure coincidence, Simon accidentally looked right at Brittany. The two were both surprised, Brittany smiled awkwardly, as Simon tried hide the embarrassment of being seen.
“Is that the last one?” Jeanette asked Simon.
“Um, yeah.” He handed it to her, trying to look casual.
“Thank you.” Jeanette gave him a peck of a kiss on the cheek. “I love you.” She said sweetly, on her way out.
“I love you too.” He sighed looking stiff.
I think I know, exactly, how to convince Simon to help me cheat. Brittany thought, feeling confident.
“So, um, what did you want to talk about?” He asked, turning to Brittany awkwardly.
She leaned her back against the windowsill. “Simon.” She started sweetly. “We’re good friends right?”
He sighed, putting his book on the desk. “What do you need...?”
“I’ve always thought of us, as real good pals.” She rambled sweetly. “And we’ve helped each other out, plenty of times.”
“Brittany…”
“I was wondering if you could, maybe, um, get me a copy of the grading sheet, in that class we have together?” She asked, with a sweet little smile.
“Oh Brittany.” He shook his head in disappointment. “Is this what a week of tutoring with Jeanette has taught you? Cheating?”
“Simon, you know I’ve been studying nonstop, but it just isn’t enough. I know I’m gonna fail this test and if I do, I’ll end up in summer school.”
“You know what they say, ‘that’s the way it goes’.” Simon told her unsympathetically.
“Oh Simon, have a heart. Isn’t there anything I can do, to get you to help me?” She pouted. “Please... I’m desperate...” She begged, giving him ‘the eyes’, the helpless wide eyed look they liked to give each other when begging for a favor.
“I do have a heart and that’s why I won’t help you cheat.” Simon said firmly. “Summer school will be unpleasant, however I’m sure you’ll be better off, for it.”
“Simon?”
“No, I won’t help you.” He said firmly. He sat at his desk and put his book in one of it’s drawers, paying no more mind to Brittany.
All right Brittany, don’t hold back, you’ve done this before. She thought, as she walked up behind his chair and wrapped her arms around him. “Simon?” She asked in a sultry voice. “Isn’t there, anything, I can do to change your mind?”
Instantly the poor boy’s nerves were wracked. He started to tremble like a prisoner in chains, waiting for his execution.
“I mean, anything...” She continued seductively. “I told you, I’m desperate...” She whispered.
He shook as her warm breath caressed his ear.
“It must be difficult for you, seeing how Jeanette, isn’t the most physical person in the world. I bet she has you just dying to know what it’s like.”
“I don’t know what you’re talking about...” He said nervously.
“Sex.” She said clearly.
He took a deep breath at the word.
“I’ll make a deal with you.” She said gently. “You help me pass this test, and I’ll set aside some alone time, for you and me. And we can do or try, anything you want, anything, I promise.”
“I can’t.” He huffed.
“Why not? Are you nervous about it?”
He pulled her arms off and stood up, taking a breath to calm himself. “Brittany.” He said turning to her, looking unimpressed. “I’ve done plenty of things I’m not proud of, but the one thing I will never do, is cheat on Jeanette.
“It’s, not cheating.” She answered, feeling a little frazzled by his unexpected response.
“And what would you call it?” He asked calmly, seeming to have regained his regular cool composure.
“I’d call it, two good friends, doing a very special favor for each other.” She said, trying to look confident.
“Oh? And what would Alvin say, if he found out?” He asked sternly, turning the question of fidelity on her.
“He would probably ask if he could watch.” Brittany said, with a dead serious look.
“Very funny.” He huffed.
“I’m not joking.” She insisted. “You wanna know something about Alvin? I’m pretty sure he’s been fooling around with Eleanor, while I’ve been studying.”
“What?” He asked surprised.
“Yeah, the other day Jeanette told me Alvin and Eleanor took a shower together, and I’m sure they’re not doing that, just to save water. Of course, I told Jeanette they did that because they’re comfortable with their bodies and wanted to save time. After all, I wouldn’t want sweet, innocent, Theodore, to hear anything bad about his Eleanor.”
“So they’re both cheating.” Simon sighed disappointed.
“It’s not cheating!” Brittany insisted. “They both want sex and can’t get it anywhere else. I’ve been too busy to spare time for Alvin and Theodore’s too shy to make love to Eleanor. I personally don’t see anything wrong with it, and I even told them that, this morning.”
“So you don’t care at all?” He asked, feeling unsettled by her attitude.
“Of course I care!” She snapped angrily. “I also told them, if I catch them together when I’m done studying, I’m gonna spay and neuter them!” She closed her eyes and took a calming breath. “But, until I have time for Alvin, I don’t consider it cheating.”
“Well, bad example...” He said, feeling a little color blind from the grey morality in front of him.
“Simon, you know you wouldn’t be breaking Jeanette’s trust, if you had sex with me, just once.” She pressed. “And you’d only be doing this, to satisfy your curiosity, that’s all.”
Simon stayed quiet, feeling as if she had read his mind. “But what would Jeanette say, if she found out about it?” He worried.
“She’ll never know, I’ll never tell her and neither will you.” Brittany said, knowing she had him now. It’s not cheating, it’s just a special little trade, between two good friends.”
Simon closed his eyes and took another breath. “...Alright.”
The last days before Brittany’s test, went by fast. As Brittany pretended to be studying, Simon worked on getting the test answers for her. Being a teacher’s assistant, Simon was able to get enough time alone with that week’s test, to take pictures of it’s answer key. After that, Brittany and Simon brainstormed a way to have the answers with her, when she needed them. Using a charm bracelet kit Brittany had, Simon made an answer key for her, out of colored beads. Each color bead represented a letter answer on the test, with one bead, for every question on the test. When the day of the test finally came, Brittany wore the answers to the test, wrapped around her wrist, in plain sight. With the answers literally, right in front of her, Brittany breezed through the long dreaded challenge.
It was after school and Simon returned home feeling upset with himself, already regretting the deal he had made with Brittany. He wanted to drop the whole thing, but he knew Brittany didn’t like the idea of, owing someone. He went up to his room, ready to grab a few things and then leave for the library, where he hoped to hide from Brittany and think of some way of getting out of their deal.
When he opened his door, the first thing he saw was Brittany, sitting at his desk reading one of his books, facing the doorway.
She eyed the door, then closed the book with a smile. “Hey.”
“Hey.” he answered, looking indifferent as he walked to his bed, put his backpack on it and started taking out a few books.
“After school I asked about my test.” Brittany told him. “And my teacher said I won’t have to go to summer school.”
“Well, that’s that, then.” He said dully, putting his books in his nightstand.
“Not exactly, what about you?” She asked warmly, ready to make good on a promise to her friend.
“Forget it.” He said, acting casual. “After all, what are friends for?” He grabbed his backpack and put it back on, ready to leave for the library.
“What’s the matter Simon?” She asked, making sure to stand in his way. “Are you nervous? Are you feeling guilty?”
“I don’t know...” He sighed. I just, don’t think I can do this.”
“Simon, I made you this offer, because you’re my friend and I care about you.” Brittany insisted. “You know, Jeanette’s told me about you two.”
This caught a worried look from Simon. “What did she tell you?”
“She says you’re always asking her to be, ‘more physical in your relationship’ and that she, ‘isn’t ready for that sort of thing yet’. I told her, she needs to try to meet you halfway. But if you have to sneak a peak up her skirt, when she’s not looking, then it’s obvious she isn’t trying.” Brittany said, sounding indignant. “Let me tell you something, for your own sake. The difference between friends and lovers is this; friends share some things, and lovers share everything, especially their bodies.”
“Brittany, there are reasons some people have trouble being physical in a relationship.” Simon told her, trying to temper her surprising mood.
“Yeah, and the only legitimate one, men can take a pill for.” Brittany huffed.
“Brittany, I get what you’re trying to do, and I thank you for it.” He said with a smile. “But I can’t do this, I wouldn’t feel right.”
Brittany felt deflated, she wished he would change his mind, but he was too devoted to Jeanette. Before she gave in, a strange idea popped into her head.
“Brittany, thanks for the offer, really.”
“Simon, I still owe you for your help, so hear me out.” She said, trying to keep him from ending their conversation.
“Brittany-”
“Trust me!” She assured brightly. “You come over to the tree house, at eight tonight. If you don’t like what I have in store for you, I’ll let it go completely and pay you back some other way, I swear.” She waited for his answer sweetly.
“And if I say no, you’ll let it be?” Simon asked with suspicion.
“If you say no to this, it’ll end there, no argument.” Brittany promised seriously.
“I’ll be there.” He relented.
“Perfect, bye!” She said, practically running out of the room on her way back home.
Simon was left wondering, what scheme was running through Brittany’s mind.
It was early in the evening, Simon had just finished his dinner and was trying to relax on the couch, watching TV with his brother Theodore. Eight o’clock had already come, but he had lost his nerve, and decided not to meet Brittany after all. I told her no in the first place and when someone says no, it’s final. He thought, trying to justify his decision.
“Oh, no, it’s no trouble at all.” The boy’s adopted father, Dave, said reassuringly on his phone, as he walked into the living room. “Don’t worry, I’ll send him right over. Simon, I have a favor to ask of you.” Dave said, ending the call.
“Is Miss Miller having trouble with her TV again?” Simon asked, with a sigh and a smile.
“No, that was actually Brittany.”
Simon’s heart sank. He knew instantly, Brittany had somehow convinced Dave to send him over.
“Jeanette and Eleanor are staying the night with Miss Miller and Brittany’s gonna be alone, so she asked if you could keep her company for tonight.”
“Um, I don’t know Dave.” Simon told him, trying to think of any excuse he could, to keep him home. “I mean, does she really, need, me?”
“Simon, I know It’ll be boring, but it’s just for the night, grab whatever you need and head over to the tree house.” Dave insisted in a firm tone.
“Huhhh.” Simon sighed disappointedly. He knew he couldn’t avoid her, so he packed a few things for the night and made his way over.
Simon made his way up the stairs of the tree house and knocked on the front door. Oddly, there was no answer, so he let himself in. “Brittany?” He called as he walked through the empty living room. He felt a knot in his stomach, spotting the the light at the top of short staircase that led to the girl’s loft, where their beds were. He guessed Brittany was there, waiting for him. He dropped his bag on the girl’s love seat and slowly made his way up to the open loft.
Coming off the stairs, he saw someone on the other end of the room, she was bent over slightly, looking out the window and wearing a familiar outfit. Her dark brown hair, was put up in a big loose bun, with a long mauve ribbon holding it together, in a droopy decorative bow. She wore a powdery, plum blue, turtle neck sweater, that fit tight in some places, loose in others and absolutely refused, to look in any way presentable. Around her waist was a pleated mauve skirt, too short to completely hide her behind. Her partially exposed cheeks, looked delicate, tightly bound by a pair of pretty, powdery lavender, cotton panties. Below her eye catching hips and thighs, were white cotton leg warmers, scrunched up around her legs, stopping just beneath her knees. Peeking out from under her leg warmers, were a cute set, of powdery plum blue, slip on, tennis shoes.
Simon was breathless, he recognised Jeanette’s favorite outfit, from when they were a little younger. Did Brittany, talk her into spending the night alone with me? He wondered nervously, his heart beating with love. “Jeanette?” He asked gently as he closed the distance between them.
“...Um, not exactly...” Brittany said nervously, as she slowly turned to face him. “What do you think?”
Simon was amazed, it was remarkable how much Brittany looked like her sister. With her hair dyed brunette and naturally set in front, and a pair of big, round, pink framed glasses; Brittany looked almost exactly, like a slightly younger Jeanette.
It was almost perfect, but the color of the eyes, gave Brittany away. Jeanette’s eyes were a calm ocean blue, deep, like their quiet and thoughtful owner. And Brittany, was bright, playful and sometimes biting, like her crisp, icy blue eyes.
“Well...” He said, unsure of how to feel. “You definitely get points for creativity.”
“Simon, you don’t have to worry about cheating on me anymore.” Brittany said with a shy expression. “You can’t cheat on me, with me.” She told him, acting like Jeanette.
“Brittany…”
“Jeanette.” She corrected.
“Brittany.” He insisted. “You may look like Jeanette, but I love her and I can tell the difference a mile away.”
“Don’t think of me as the real Jeanette, think of me as a toy.” Brittany insisted, still trying to look demure like her sister. “And think of tonight as a game, where you make one of your fantasies about Jeanette, as real as possible. There’s absolutely nothing wrong with fantasising about your girlfriend, and tonight you’ll have the perfect little prop with you. I’ll be your living doll, you can pose me, cuddle with me, and play with me, all you want.” She said with an adorable smile.
Simon's heart was pounding and his stomach was tight, he didn’t want to say no anymore. It’s difficult for any male to separate love and lust, but it’s a dozen times worse, when that male is just a boy. He knew Jeanette loved him, but his heart and body were aching, to feel, that love, just once.
“Okay.” He sighed.
“I’m all yours, Simon.” She said trying to sound like Jeanette. “Hmm!” She squealed and flinched, as he plunged a strong kiss on her, while grabbing as much of her shapely, supple backside, as he could fit in both his hands. Simon pulled Brittany’s body right against his, squeezing her pert cheeks and pelting her lips with sweet, passionate kisses. Brittany was a little surprised by the intensity of the usually reserved Simon, but she enjoyed everything he was doing. She loved feeling their bodies pressed firmly together, as his hands explored her supple figure. Each grab flowed from, firm squeeze, to light tug, to gentle caress, all while their kisses became deeper and more humid. She especially loved it when he ran his fingers through the fur of her sensitive tail, every time he would handle it, her whole body would give a little shake. Everything he did, was sparking her own physical passion. She let out a deep sigh. I haven’t had sex for two weeks. She thought, realising how much she missed the indulgent daily routine, she enjoyed with Alvin. Brittany couldn’t stand the wait any more. “I’m ready.”
Pulling away for a moment, Simon held her hands, admiring the ‘living doll’ in front of him.
Brittany was next to her own bed, but was surprised when Simon lead her across the room, to Jeanette’s bed. The realization they would be using Jeanette’s bed, was almost like a splash of cold water to Brittany. She nervously laid down on her sisters bed, with a smile on her face, that was genuinely shy and awkward. I’m gonna have sex in my sister’s bed, this is so kinky. She thought, practically quivering.
“You’re a good actor, Brittany.” Simon told her, as he sat on the edge of the bed.
“I’m Jeanette, silly.” She reminded sheepishly. Brittany was far from being a virgin, but for some reason she still felt nervous. She figured it was the situation, pretending to be Jeanette, about to have sex in her bed. Ohhh, this is so kinky. She thought, taking shallow breaths as she tried to relax. In spite of her nerves she pressed on. Using just her feet, she slipped off her shoes and gently kicked them off the bed. With a few anxious huffs, she pulled her sweater up and over her head, knocking her pink glasses off with a ‘plik’. She dropped the sweater on the floor and grabbed her glasses from beside her and put them back on. Simon enjoyed seeing her simple, but cute, lavender bra. She easily reached behind her back and unhooked her bra, something she had done countless times for Alvin. With both hands, she slowly slipped her bra down her chest, treating Simon to a teasing show, as she revealed her small, but pert, young breasts.
Simon sighed as he watched her, the petite girl in front of him, was an absolute treat for the eyes. He took a nervous breath, then began taking off his clothes. He kicked off his shoes, unbuttoned his pants and slid them off.
Brittany was just as nervous, if not more so, as she slowly slipped her panties off and dropped them over the other side of the bed. She left her skirt on, feeling too shy to show her vulva to her friend.
Simon paused for a moment, but then slipped off his underwear, revealing a lively erection.
Brittany watched with a nervous swallow. Oh wow, he’s really serious. She thought awkwardly, as the reality set in. He’s really gonna do it with me. She closed her eyes, nervous at the thought of having sex, an emotion that the bold girl hadn’t felt, in what seemed like forever.
Simon gently placed himself on top of her and began giving slow, feathery kisses to her neck. His kisses wandered down to the top of her chest, teasing Brittany with the promise of his warm lips moving to her young breasts.
“Hey...” He interrupted his gentle display of friendly affection, for a moment. “...You don’t have to do this for me.” He assured with a warm look.
Brittany’s heart melted at his genuine concern. “...I want to.” She said with the most innocent look in her eyes. She leaned up and gave him a peck on the lips, then wrapped her arms loosely across his back and tried to pull him down.
His hands caressed her upper arms, as he brought himself down again. Starting where he left off, he scattered a few delicate kisses down one of her young, supple breasts. Reaching her nipple, he teased her with a kiss, just to the side of it, then again, with another kiss to the opposite side.
She sighed as her passion continued to rise. It’s kinda romantic, how he takes his time, just to help me get in the mood. Brittany thought. I wish Alvin was this considerate, with him it’s just a few kisses and straight to the action. “Mmmh.” Brittany sighed, trying to signal him to move on.
Simon got the hint and closed a kiss, slowly around her firm nipple, giving it the slightest pull, as he drew his lips away.
“Hah!” Brittany shivered as she cradled the back of his head with both hands.
He switched to her other breast, giving it the same treatment, as he began caressing her side with one of his hands. He gently massaged her side, his hand flowing back and forth, as it made it’s way down past her hip, to her thigh.
“Hmmm.” She sighed, trying to hold her already feverish passion in. Damn it, I want him to just, fuck me, right now. She thought in a hot huff. But I have to be patient, I’m sure if he was with Jeanette, it take her a while to warm up. I got to give Simon a chance to practice for her.
Simon was caressing her thigh and would slip his hand under her skirt now and then, teasing her inner thigh.
She spread her legs slightly, almost ready to beg him to end their foreplay. After a few more moments of his kissing and caressing, Brittany just couldn’t wait any more. She grabbed his teasing hand and held it firmly. “Simon, I’m ready, please.” She called, too hot for anymore of his romantic maneuvers. The sassy girl needed sex, she had put off sex with Alvin for two straight weeks, while she studied. For an energetic and confident girl, who just before, had been having sex every day, two weeks felt like forever.
Simon flipped her skirt up, at last getting a look at her young vulva. Her bare feminine cleft had a simple beauty, that only a passion driven boy, could truly appreciate. After admiring Brittany for a moment, Simon brought his hips forward, resting his member atop her mound.
Brittany felt him pull his hips back slowly, his penis gently dragging against her sensitive clitoris. She licked her lips anxiously, nervously craving what would come next. “Huh.” She sighed as she felt his tip pressing into her wanting mound.
Feigning confidence, Simon pushed into her, with one smooth motion. Instantly he felt her soothing warmth and the welcoming squeeze of her inner walls. “Huhh...” He panted softly, almost losing his balance from the overwhelmingly luscious massage, her experienced feminine muscles, forced onto his sensitive virgin member. “Oh, wow...” He trembled at the new experience.
“Hmmm...” Brittany hummed with lust, as she groped at her friend, from within. She grabbed the sheets tightly and took a few hot breaths, remembering how much she enjoyed having her squeezing inner folds, wedged apart by a firm, hot, penis. The two kept their eyes shut for a while, each one needing a moment to calm themselves.
When Simon opened his eyes, he saw only Brittany, her convincing disguise, failing to hide the sweet and devious girl, from him.
She reached up and placed a hand on his cheek. “Take your time.” She said looking at him with the warmth of a true friend.
His heart ached from the love she gave so openly. He looked down at her, with the eyes of a hurt puppy. Leaning in, he gave her a gentle kiss. She placed her arms around him and returned his kiss a dozen times over. He began to move his hips back and forth slowly, trying to savor the new and somewhat intense, sensations he was feeling. As he gently pushed against her, she brought her knees up, keeping her feet on the bed, as she slid them closer and spread them a little wider. Simon took advantage of her new position and pushed himself into her, as deep as he could.
“Hmm.” She sighed quietly with pleasure, pressing her thighs tightly against him, making her inner space, as narrow as she could in that position.
“Hah...” He panted, struggling with the added stimulation. Not only did she feel almost tight to him, but she gave a surprising bit of pull with her inner muscles. To Simon, Brittany’s velvety folds, felt wonderfully snug, warm and moist. He trembled with every move he made, feeling as if he was already at his limit.
“Simon.” Brittany called for his attention gently, after seeing the tension his face. “Don’t move for a bit.” She gently pulled him closer. “Relax, tell me how you feel.” She advised warmly.
He carefully laid down on her, with his head beside hers. Brittany, I don’t think I can last.
“Jeanette, silly.” She reminded as she cuddled with him. “And it’s okay if you don’t last long, I just want you to enjoy yourself.”
He held her tightly. “I just wish things were different.” He sighed as if he carried the weight of the world on his shoulders.
“You just keep trying, it’ll get better for us, I promise.” The faux Jeanette insisted.
“Hmm-hmm-hmm!” Simon laughed gently. “You’re really doing this, huh?” He asked happily as he lifted himself up. “You’re a real friend, Brittany.” He said looking down on her with a warm smile.
“‘Jeanette’, Simon, ‘Jeanette’.” She insisted as she pointed to her face with an adorable, mousey smile.
He lowered himself for a kiss. “Tell me what to do for you.” He said gazing into her crisp, ice blue eyes. “I want you to enjoy as much as I do.”
Brittany felt touched by his concern for her. “Oh, Simon... Lay down on me.” Brittany invited, as she pulled him closer.
“Like this?” He asked as he kept his body just barely on hers.
“No. All the way, I wanna feel all of you, on me.” She insisted. “Don’t worry, I’ll be fine.”
“Okay, but tell me if you need me to get up.” He said resting his body gently on hers.
“Mmmh... just like that.” She sighed as she wrapped her arms around him, and squeezed her thighs together, even tighter.
“Ohhh, you feel amazing, I really don't know if, I can keep going.” He sighed, pushing himself up with the slightest of shivers.
“Alvin says that all the time, it was a bit of a problem for us. But I’ve been working with him on that, he’s gotten much better at controlling himself.” She looked up at him with sheepish embarrassment. “And he really needed it, you were almost an uncle, twice. Just pay attention to how tense you’re getting.” She advised warmly. “When you feel the tension building up and you know you’re getting close to finishing, just slow down to an easier pace and breath deep. You wanna move slow, but keep moving, so you don’t lose all the pleasure, built up between you both. Breath gently and deeply, in through your nose and out through your mouth. And don’t get distracted by it, keep your focus, on you and the one you love, at all times.” She said, relaxing as she looked deep into his eyes. “When you ease up on the physical side of things, that’s the perfect time to let a girl know, how much you care about her. Look in her eyes, caress her, give her plenty of kisses, and make sure you tell her how you feel.”
“I wish Jeanette was more like you.” He blurted out thoughtlessly, in an intimate moment of honesty.
For a split second they were both surprised, but Brittany quickly pulled him down for a kiss. “And I wish Alvin was more like you.” She confessed, refusing to let things get awkward between them. “You’re a great friend, Simon and I’m glad we got to try this with each other.”
“Thank you, Brittany.” He said trying to hide the embarrassment on his face.
She wrapped her arms around him and pulled him down again. “Come on Simon, keep going.”
Simon laid himself back down on her, as gently as he could. “Like this, right?”
“Hah, just like that.” She sighed passionately wrapping her arms tightly around his back. “I wanna feel your body, right on me.”
Simon started thrusting slowly, back and forth, making sure he wasn’t too close to an orgasm. With the tension of his member at a place he felt confident with, he began to move with purpose. He started tilting his member at different angles, searching her for any sensitive spot inside, that was unique to her. Although he was a virgin, he did know a fair bit about sex, almost entirely from reading. On his bookshelf, hidden in plain sight, he kept a translation of the Perfumed Garden. What his family thought was a book of Arab poetry, was in fact hundreds of years of intimate advice and now he was using that advice. He varied how deep and fast he would thrust into her, trying to pick up on the small cues, that would assure him he was doing something she enjoyed. He felt her inner folds squeezing firmly against him now and then, but he knew he wasn’t doing enough to impress her. Unfortunately for him, Brittany was a nightmare to please physically, something his brother Alvin knew, all to well. Simon had an idea, he put his legs back further, to the point where he was practically pushing with his toes.
“Oh, don’t pull out.” She whined.
“I won’t.” He assured as he put more of his weight on his elbows and pulled himself up, trying to rub his pelvis as firmly against hers, as much as possible with each new thrust.
“Oooh...” She cooed, finally showing some signs of deep pleasure. “That's kinda nice...” She sighed as she swung her hips up, trying to meet his thrusts halfway.
Simon felt proud of himself, he knew the grinding press of his pelvis, would give her the extra pleasure she was acing for. He tried to thrust as deep as he could, even though his new position had him agonizingly close to slipping out of her. He was confident that he could keep up the pace without losing control.
“Hah! You’re teasing me so much...” She shivered as she tried to meet every thrust halfway with a heavy swing of her hips. She loved the constant rub she was getting on her clit. The teasing tickle within the very rim of her wanting womanhood, was enough to get the poor girl’s blood feverishly hot. “Ohhh... Simon, kiss me!” She begged, feeling dizzy from the pleasant heat within her.
He adjusted himself just enough for a kiss, without letting up on his constant rubbing and prodding. The two met with a few haphazard kisses, neither willing to break the rhythm they had settled into.
“Hahhh... hmm...” Brittany languished in pleasant torment, the tension of her clit growing more with each movement. “Faster...” She panted breathlessly. “Simon... faster…”
Simon did his best, to give her what she asked for.
“Oh, ha, hmm...” Brittany squirmed beneath him, feeling the tension between her thighs about to break. She huffed deeply as she readied herself. “I’m so close. I’m so close.” She practically whispered in hot anticipation.
Simon wanted to slow down, but refused to let up, knowing if he could please Brittany, he could definitely please Jeanette.
Brittany huffed with passion as Simon began moving even faster. “Hmmm-rhhhmmm...” She practically growled, as she felt herself reach the breaking point. “Umm, huhh... Ha! Hummm-mummm! Ohhh!” Brittany nearly screamed with pleasure, as her body began to dance to the rhythm of a pounding orgasm. “Humm-muhhh, Hahhh!” Brittany heaved sighs of heavy pleasure, throwing her legs up and wrapping them around Simon, as tightly as she could. She hooked her arms over his back and griped his shoulders as tightly as she could. Although she was smaller, she was still stronger than Simon, she used that strength to pull him down on her and hold him firmly in place.
Simon relaxed, understanding Brittany’s obvious signal to stop moving.
“Mmm... ohhh...” She murmured quietly to herself, as she slowly came back to her senses. It took her more than a moment to compose herself. “Well...” She panted weakly. “That was alright, for a start…”
“Hmm-ha-ha-ha!” Simon broke out laughing at Brittany’s joke.
“Hmm-hmm-hmm!” Brittany giggled along with him, as they held each other tightly. The two enjoyed the cozy heat of each others bodies for a while, until Brittany slowly unwrapped herself from her friend, as she finally began to relax in earnest.
Simon had recovered some of his stamina and the gentle warmth of her inner space beckoned to him. He pulled back, setting himself into a new position and then slowly pushed himself deep inside her.
Brittany gasped as she pushed her hands against his hips. “Oh Simon, no... I, can’t. I’m too sensitive for more...”
“I suppose this is a good place to end things.” He said, pulling his member from Brittany’s tender warmth.
“Wait, not yet.” Brittany said, patting the side of the bed. “Lie down.”
"Brittany, you don't have to-"
“Aren’t you my friend?” She insisted with a caress of his cheek.
He laid down next to her, anxiously.
Brittany sat up, pulled Jeanette’s glasses off and gently dropped them over the side of the bed. “Guess I don’t need these anymore.” She sighed, considering her attempt at roleplay a failure. She shuffled over to his legs, then laid down on her on her side, resting her top half on his thighs, her face, right next to his penis. Balancing herself with an elbow on the bed, she leaned over and grabbed his member with her free hand and brought her mouth down on it.
The warmth of her mouth was heavenly, the feel of her hot tongue pressing firmly against the sensitive underside of his penis, was enough to bring him right back to the edge of orgasm. “Ohhh, Brittany! That feels so good!” He whimpered through the excitement of another new sexual experience. “I can’t do this anymore.” He sighed with hot lust. “I’m gonna finish in you mouth if you keep this up.”
“Don’t worry.” She assured. “Let me me help you.” She told him as she held his penis firmly in her hand and began sucking on the tip quickly.
“Oh Brittany, you really don’t have to do this!” He said trying to push her back.
She batted his hands away quickly with a sassy look. “Mmh!” She kept his tip close to the edge of her tongue, barely keeping her lips over it. She waited impatiently as she worked his shaft with one hand and began to fondle his balls with the other. She loved giving a blowjob after sex, there was something about the sudden intensity of catching an orgasm in her mouth, that made her feel incredibly aroused.
“Brittany! Uh! Hmm! Huhhh! Muhhh!” He tried to warn her one last time, as he broke into a strong orgasm.
Brittany’s heart fluttered when she felt his hot semen, leap onto her tongue. “Mmm...” She sighed, loving the salty taste and slimy texture, as she continued to suck him gently, taking a moment to swallow, now and then. She didn’t truly enjoy the way it felt or tasted, rather, she enjoyed that it meant she was pleasing someone sexually, which left her with an odd sense of accomplishment.
“Ohh...” Simon moaned slightly, as Brittany made certain she took every single drop from him. He pushed her away gently and she let go of his now, overly sensitive member.
“So, how was it?” She asked as she wiped her mouth proudly.
“It felt amazing...” He sighed breathlessly, feeling heavy and tired.
“Thanks.” She said, as she crawled over and laid down next to him. She noticed he was avoiding her eyes. Brittany could tell, he was already worrying about Jeanette again. “Simon, come here.” She told him, as she coaxed him to her, by putting her arm around him. “Come on, lie down, right here.” She pulled his head down on her chest, his face ended up comfortably pressed against one of her petite breasts.
“Brittany... can I talk to you...?”
“No, not about that.” She said holding him gently.
“Can’t you give me, any advice?” He asked with a hug. “Brittany, you know her better than I do…”
“Just keep trying, be patient, little by little, I’m sure she’ll come around, she loves you.”
“But, I’ve been trying…”
“Shhh... I said we’re not talking about that.” She said, gently stroking his hair. “Just relax... everything is going to work out for you, I just know it will. She assured with a love of a sister.
The soothing warmth of her embrace and the reassurance of her words, were enough to put his troubled heart at ease. Before he knew it, Simon had drifted off, into a comforting sleep.
The next day, Simon was feeling a little more confident. He decided Brittany was right, he just needed to keep trying to help Jeanette feel more comfortable with physical affection. It was the middle of the afternoon and Simon was with Jeanette in the boy’s room, talking about what their plans for the summer would be.
Near the end of their conversation, Brittany let herself in and glanced around for a moment. “Hey, have you guys seen Alvin?” She asked with a hint of suspicion in her voice.
“He’s not here, as far as I know.” Jeanette answered.
“I better not catch him hanging around Eleanor.” Brittany said to herself, with a slightly annoyed look.
“Why not?” Jeanette asked cluelessly.
“Actually, he was with Theodore the last time I saw him.” Simon told her.
“Oh, well, I have all summer now, so he better make time for me.”
“I’m gonna get going, then.” Jeanette told Simon as she grabbed her leather satchel from beside his desk. “I wanted to stop by the library before it closes.” She leaned over and gave him a peck on the lips.
Simon put an arm around her and pulled her close, giving her a full kiss on the lips. Brittany smiled as she watched, finding the gesture romantic.
“Simon!” Jeanette complained, as she pulled away. “Stop it! You’ve been acting, very bold, all day and you know I don’t like that.”
“Sorry.” He said looking deflated.
Brittany couldn’t stand listening to Jeanette scolding her loyal, loving boyfriend. “Jeanette, what is wrong with you?” She huffed at her sister. “He loves you and he just wants to be closer to you.”
“This isn’t about how much he loves me.” Jeanette defended. “This is just about how much, physical attention, he can get out of me. I know he’s my boyfriend, but just because we care about each other, doesn’t mean he needs try to, do things, with me.”
“You have to stop getting on his case about it, Jeanette! He’s a boy! He’s supposed to try to, ‘do things’, with the girl he cares about!” Brittany snapped.
“This is just like last time!” Jeanette countered. “You’re giving the same argument, all over again!”
“Because it’s the truth! And the truth doesn’t change, just because you don’t like it!”
Jeanette slung her satchel over her shoulder. “I am, not, doing this!” Jeanette insisted with a quick turn of her back, as she started out the door. “You’ve already chewed my ears off about this before!”
Brittany huffed as she followed her sister. “Oh, I haven’t, begun, to ‘chew your ears’!”
All the way down the stairs, the girls could be heard, sweetly squeaking their argument.
Simon sighed with a smile. “You’re a real friend, Brittany.”
- 1
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Brittany And Simon, Helping Each Other