Best Friend's Kid Sister

by Storyteller4U

Copyright© 2013 by Storyteller4U

Romantic Sex Story: This is a light, simple story about a shy woman who confronts her childhood fantasy.

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   Consensual   Romantic   Heterosexual   Slow   .

"Cindy, I know you're hiding behind that door. Get a life, already. We don't need a shadow," said Ted.

"Ted, don't give her such a hard time. She just looks up to you and admires her big brother.

"Dan, I just wish she'd admire me from her own room."

"Should I or shouldn't I?" questioned Cindy. She mulled the question in her head as long as possible, but time was running out. It was now or never. "Here goes nothing (or everything)," she heard echoing in her brain. Picking up her cell phone, she dialed. "Hi Dan. You probably don't remember me, but this is Cindy Moore ... Ted's kid sister?" she added cautiously.

"I remember you, Cindy."

"Oh ... I guess I was quite the pest back then."

"No, Cindy, not at all. Let me share something with you. My dog constantly maintains a watchful eye over me, yet I couldn't love her more."

Cindy wasn't quite sure what to make of this comment, so she decided to just present her request. "Dan, I'd like to ask you something. Don't feel obligated to say yes."

"Cindy, I never do anything I don't want to do."

"OK," she said hesitantly. Strengthening herself inside, she continued, "Dan, I am to be presented an award by my company. Traditionally, the CEO hands the award to the recipient's spouse or significant other, and then that person places it around his or her neck. I don't have a spouse or significant other to turn to, but then I thought of you. You always came across as caring and considerate. I'm hoping you might be willing to do this one favor for me. It's not like this is a date or anything. You'd get to eat a nice meal, and nothing would be expected of you other than to fasten the award around my neck during the ceremony."

Cutting her off, Dan said, "I'd love to, Cindy."

Caught off guard by his response, Cindy stammered, "Thank you, Dan. I truly appreciate your willingness to do this. The function is this Saturday night, at the local Hilton. I hope you are free for the evening."

"I'll clear my schedule for you."

"No, Dan, it's all right. Don't clear your schedule for me. I'll find someone else," Cindy disappointedly said.

"Cindy, all I was planning was to continue working on the cabinet I'm building in my woodshop. I can do that any time. What time would you like me to pick you up?"

"5:30 would allow us to get there unrushed. Thank you, Dan. My address is 409 Maple Street #104. You have no idea how much I appreciate this. I'll see you then," Cindy quickly finished and hung up the phone. Her legs were shaking, and she didn't think she could hold herself together much longer.

While continuing to hold the phone in his hand, Dan thought in his mind, "I believe I have a very good idea, little Cindy."

Saturday evening went smoother than Cindy expected. She even found her legs stopped shaking, as Dan helped the evening's conversation flow. Eventually, it was time for the award ceremony. As she stood before the crowd, Cindy realized Dan's presence, next to her, helped her feel stronger. She knew it was silly to feel that from someone who was just doing her a favor, but she felt it anyway. She felt proud, as she held onto his arm, and her anticipated stage fright melted away. The CEO handed the award to Dan, after sharing with everyone what Cindy had done to deserve the honor. He mentioned her being 25 made her the youngest recipient of this honor in the 100-year history of the company. Dan moved close to Cindy, so he could fasten the ribbon's clasp behind her neck. The closer he got, the more intoxicated she felt by his manly scent. After fastening the clasp, he put his strong hands on her shoulders, looked deeply into her eyes, and then proceeded to plant the tenderest kiss she could imagine on her lips. "Wait!!" her mind screamed, "this wasn't part of the agreement." A hurricane blew through her head and body. Words couldn't come from her mouth. All she could do was smile. She was unable to say much, the rest of the evening.

When Dan dropped her off at her apartment, he said, "Cindy, thank you for allowing me the honor of accompanying you, this evening. I was very impressed to hear the CEO talk of your accomplishments. You've turned out to be a pretty amazing woman."

Cindy didn't know what to say, or even if words would come out of her mouth, but she did squeeze out a quiet "Thank you, Dan." She attempted to turn and retreat into her apartment, but Dan's arm somehow appeared behind her waist, and she found herself being drawn close to his body. She shyly looked down; as she felt his strong muscles surround her. She felt his fingers gently touch her chin, and her eyes rose to meet his. Their lips touched, again. Cindy pulled away and disappeared into her apartment, tears streaming down her face.

Sunday, Cindy spent all day in bed. That was the only place she felt totally secure, fearful she would fall apart if she left the warmth of her cocoon of blankets. Upon returning to work, everyone asked her about the handsome man who accompanied her to the company dinner. When she shared he was just a friend, the typical response she heard was, "That's some friend, care to fix me up?"

By Wednesday, she could no longer live in denial. She called Dan. "Dan, I'm sorry I failed to more graciously thank you for accompanying me to our company's dinner. I truly appreciated everything..." After thinking for a moment, "Yes, everything."

"And I truly enjoyed being with you, Cindy."

"Dan, you're a well-educated and respected man, but what do you know about me?"

"Cindy, on Saturday, I learned you are a dedicated, creative, caring and respected employee."

"No, Dan. What do you know about me?"

"Do you really want to hear it?"

"Yes, Dan. I need to know the truth ... the whole truth."

"OK, Cindy. I first met you when you were 5-years-old and I was 10. I met your brother in my class, and we became best friends. Ted and I did everything together. Whenever I spent time at your home, I would always notice you shyly watching from behind some large object. You thought it hid you from anyone's sight, but I knew you were there. Ted would attempt to chase you away, but I didn't mind you being there. I could tell you had a crush on me, and I thought you were adorable. When I had the opportunity to divide up a treat for everyone, I always did my best to give you the larger piece, or the one that had a bonus attached. When I did reach out, in any way, you shyly looked away or ran to another room. I thought the feelings you felt would fade, as you got older, but I realized they didn't. I never saw signs of or heard you were interested in any guy. Your family just thought you were too shy to have a relationship. I remember one time I cut myself, when you were about 11. Without hesitating, you slid your slip off and wrapped it around my bleeding arm. I started to thank you, but you just ran into your house. I still have that slip, and it's something I've always treasured"

"I didn't realize I was that obvious. But, Dan, if you truly knew, what's the reason you never reached out to me?"

"Cindy, I understood your shyness, as I've battled my own shyness issues. I believed you just weren't ready for anything more than what you were already doing, and I respected that. Something deep inside me told me, when the time was right, and you were truly ready, you'd reach out and make contact with me. I didn't want to take any chance of chasing you off by showing interest before you were ready."

"What will let you know I'm ready?"

"Cindy, you just let me know ... by asking for the whole truth. I don't believe you would have asked before you were ready to hear it, and being ready to hear it I interpret as being ready to face your fears and desires."

"Dan, thank you for being so patient and kind. I've wanted to be ready, for years. Maybe I used the company dinner as an excuse, but I can't remember a time in my life when I didn't want you to notice me. Your unexpected kiss sent a flood of emotions rushing through me. This isn't just about me, though. Could someone like you truly want to be with someone like me?"

"Cindy, I can't answer for these hypothetical someones, but I know I would be honored to be with you. I'd love to take you on a real date, though. How about this Saturday."

"Yes, Dan. I don't even care what we do. I just want to openly acknowledge my feelings for the first time in my life."

"And I've looked forward to that, also. I've always wondered what lies behind that cute face."

"Do you really think I'm cute?"

"Actually, you used to be just cute. Now, you've blossomed into a truly beautiful woman, though I happily notice you haven't lost the cute overtones." Cindy was happy they were talking on the phone, so he couldn't see her blushing.

"Just tell me how to dress, and I'll look forward to Saturday." She blushed again, as she pictured Dan telling her there was no need to dress. Luckily, or hopefully, he couldn't read her mind.

"Let's do casual and enjoy a picnic," offered Dan.

"Only if you allow me to provide the meal," said Cindy, eagerly.

"That sounds fine with me, unless you'd prefer my specialty of peanut butter and jelly sandwiches."

"Let me do it. It's the least I can do, since you've been so considerate of me."

"I'm sure it will be as delicious to my taste buds as you are to my eyes." Red again. Cindy vowed to herself she would find a way to stop blushing before Saturday. "I'll pick you up at noon."

"Thanks, Dan. I really mean it. You're one of a kind, and I think you realize I've always liked what I saw."

Saturday came, and Cindy met Dan at her door with a wicker basket on her arm. Both had smiles on their faces. Setting the basket down, Cindy said, "Dan, I believe I owe you something, not that you expected to be repaid, but it's something I want to do." She then put her arms around Dan and kissed him with all her heart. While doing her best to catch her breath, after their lips parted, she continued. "Realize that was just a down payment. I still have many more installments to pay on what I hope will be a long–term indebtedness."

Dan smiled, and then said, "Me, too." Dan took the basket, Cindy took his hand, and then Dan led her to his car.

The picnic area Dan chose was lush and secluded. When they laid out their blanket and supplies, Cindy looked around and said, "Wow, this is beautiful."

"You sure are," he responded.

"No!" she exclaimed, as heat rose to her cheeks. "I promised myself I wouldn't blush today."

"And deny me your lovable vulnerable innocence? Cindy, I'm not interested in a perfectly packaged plastic ideal. I'm interested in you, red cheeks and all. Please be the woman I want, not the woman you think you should be."

"But, I don't want you to see me as just a little girl."

Dan looked at Cindy and started walking around her, touching her hips, back and arms as he circled. Standing close to her back, he took a handful of material from each side of her knit top and stretched the material back toward him, causing the material to mold itself over her small pert breasts. Looking over her shoulder, he admired the view, while saying, "Sorry, Cindy, other than that adorable twinkle in your eyes, I can't find any signs of a little girl. I'm jealous of this mesh that can enjoy what it merely hints at to me. I look forward to replacing this delicate material with my not so delicate hands."

Cindy took hold of Dan's hands and placed them firmly on her breasts. Looking over her shoulder at Dan, she said, "Dan, never deny yourself the desires I am capable of fulfilling, for I freely share with you all that adds to your life. I long to feed you the energy you so generously feed me. If my blushing feeds you energy, then I'll never hide it or anything else from you, ever again." Turning toward him, she unleashed the passion she had stored up over the years. When their lips parted, she said, "I am yours, Dan. Whatever enjoyment I am capable of bringing to you is less than you deserve, so I vow to continue what I can for as long as I can." She guided Dan down to the blanket, helped him stretch out and then climbed on top of him.

Dan loved feeling Cindy's body caress his, and her kisses were to die for. Knowing she had little if any experience with other guys, he figured her talent must be innate. He didn't care where her talent came from; he found himself lost in its pleasure. During one of the few moments Cindy allowed him to breathe, he said, "Cindy, my mom's not going to like you."

"Why not, Dan?" she questioned.

"Because you allow me to have my dessert before my meal."

Cindy smiled and said, "This can be our little secret from her, but you are welcome to enjoy dessert any time you wish. I place no limits and will never deny you."

Eventually, they took a break and brought out their meal. As they sat cross-legged and prepared to eat, they each looked at the other. Their eyes dropped, and smiles came over their faces. "I guess we won't be able to hide our feelings from each other, ever again," Dan said, as he stared at the growing dark spot between her legs, while she eyed the bulge she wondered how his pants could confine.

They enjoyed feeding each other the delicious meal. Afterward, they cleaned up and decided to walk off the food. The walk through the forest filled their senses. They felt themselves becoming more attuned with what surrounded them, as they found themselves becoming more attuned to each other. They couldn't seem to walk many steps before touching or kissing the other. They were unquestionably happy. As the sun dropped below the mountain ridges, they reluctantly packed up and headed home.

When Dan walked Cindy to her door, she asked, "May I offer you something." When he asked what his choices were, she answered, "coffee, tea or me," with a smile. Dan didn't hesitate as she held the door open to him. Her apartment was small, yet comfortable.

"Cindy, let's sit on the sofa." He sat down, and she followed. He put his arm around her shoulders, and she moved in closer. He took her hand and held it tenderly. "Cindy, I don't want you to feel rushed or obligated, in any way. The only demand I place on you is the continued sharing of your sweet smile. Never feel you owe me anything or you should do anything. Whatever we share must be mutually desired and enjoyed. I don't care what you've heard guys want or expect from women. I only want to share in your comfort and love. Though the physical connection is very enjoyable, what I value most is the emotional connection. Sharing your thoughts and feelings with me will bring me more joy than any type of physical gymnastics or performances. I'm open to and will enjoy the physical expressions you lovingly desire to share, but they will happen when you are ready, not before. Let's learn to appreciate each little step rather than seeing how fast we can do everything that's possible to be done. I can tell you want to give yourself to me, and I appreciate your desire, but it takes time to learn to appreciate the subtleties of love. If you go to a buffet and eat quickly, you'll find yourself uncomfortably overstuffed before you realize you have reached your limit. Let's take our time, so we can understand and get used to each new step."

"Dan, it's true I feel this intense need to prove my feelings to you. I want to show you I'll never hide or deny you anything. Though this is a strong desire of mine, I also have fears. Though I've studied all I could, I've never actually had any experience with another person. I want to be everything for you, but I fear my inexperience and less than ideal physical attributes will leave you disappointed. Maybe I feel a desire to rush, as I need to learn how you see me, and whether what you see is what you want to see. Not till my company's dinner had I ever felt tender lips on mine, and only my hands have experienced direct contact with my femininity."

"For someone so inexperienced, you share amazing kisses."

"I actually spent many hours studying movie love scenes in slow motion, practicing kissing my hands and arms. I'm happy you like the results. This is just one example of the reassurance I seek. I passed this test, but will I pass the others? I know I'll experience pain when you enter me, yet I look forward to that pain and can think of no one else I'd want to share that experience with. Oh, Dan, I just want to measure up in your eyes. I don't care what others think; I just want you to feel fulfilled by what I have to share."

"Cindy, make your hand into a fist." She complied, with a confused look on her face. "Now quickly force a finger from your other hand into the small opening encircled by your thumb and forefinger."

"Ow, that doesn't feel very good."

"Now let me see that fist." With his tongue, Dan slowly lubricated and slid into that opening. "Which did you prefer?"

"As if you need to ask. You already know the answer."

"Yes, but I want you to know the answer."

"I obviously preferred what you did."

"What I did was to take my time, gently introducing myself to you, so you could get used to me and be comfortable with my presence. Cindy, this is what I want for us. I don't want you to spread your legs and tell me to get it over with already. I know you feel safe with me, but I also want you to feel comfortable with me, which requires time to get to know each other and become familiar with each other. Today was a beautiful start, and I believe you are ready for us to go a bit further, but let's take it slow and easy, so every experience we share takes our relationship to a wonderfully new dimension."

"Dan, thank you for opening my eyes. All I wanted to do was to please you, but I now realize if it doesn't work for me, it won't work for you. If this is a taste of love, I'm hooked. We've done enough talking for tonight. Let's share love, now."

Cindy looked up lovingly into Dan's eyes, watching them grow in size as they approached her to allow their lips to once again meet. Dan showed her how intimate a kiss could be. The variety he shared far surpassed the limited options she saw in movies. Every time she thought he had taught her all, he shared a new one. While he kissed, his hands touched her, giving her sensations she never experienced while practicing with her own hands. She didn't realize how sensual an arm or shoulder could feel. When his hand approached a breast, he sensed her tense slightly. "Cindy, I know you have no desire to withhold anything from me, but I sense your breasts are another area where you may have some self doubts."

"Let's put it this way, Dan. I'll never get an invite to the Playboy mansion."

"And what leads you to believe quantity is better than quality? Let me see what we have here. Mmmm. The ideal size, shape and density."

"Dan, please remove my top, as I don't want anything to get in the way of your exploration. I want you to know me as I truly am, warts and all."

After Dan slowly slid the top over her head, Cindy stared straight ahead, totally aware of her full exposure. "I hate to have to break the news to you, Cindy, but these aren't warts." Dan's touch convinced her he definitely wasn't settling for an inferior product. His pleasure was real, as was hers. She looked down lovingly as Dan tenderly suckled on her nipple, and, for the first time in her life, felt she was exactly as she wanted to be. She couldn't believe any other shape or size could possibly feel any better than hers were feeling, right at that moment. She was happy. She was fulfilled. She never wanted this moment to end. Unfortunately, the date did come to an end, reluctantly for both of them. Dan promised the anticipation of each new step would help in their receptivity and pleasure. As an example, he shared, "A balloon is less likely to break when you blow it up slowly, as compared to using a high-pressure line." As they stood up, Cindy slowly turned, giving Dan a completely revealing view from her waist up. She knew he enjoyed what he saw, so her self-doubts and hesitation disappeared. She felt happy to share his obvious enjoyment. It now was clear to her how sharing the joy of a loved one could bring more joy than was possible through self-serving actions. She loved the way Dan looked at her, looked at her as a real woman, and she was enjoying being a woman. She lovingly gazed at Dan as she spread her arms. He didn't resist her invitation for their final embrace of the evening. As they hugged and kissed, Cindy wanted to study and memorize every aspect of Dan's lips on hers, but found herself distracted by the sensations of his hands on her bare back. This was another lesson to prove the value of taking things slowly, no matter how eager she felt.

Cindy and Dan enjoyed the newness of everything they experienced, whether activities in public or loving in private. They were growing together on a firm, well-developed foundation. No doubts or instability could be found. On one occasion, at her apartment, Cindy asked Dan his thoughts on pubic hair. She didn't have a lot of hair, but she wanted Dan to be pleased with what she did have. "That all depends on what we have to start with," Dan responded.

"Well, you're a lot of help," she coquettishly pouted.

"Cindy, let me tell you a true story about Michelangelo. He was once asked how he brought forth the magnificent statue of David from a block of marble. He responded that David was already in there, waiting to be freed. All he needed to do was chip away what was not David."

"Will you be my sculptor, then, Dan?"

"I'd be happy to," said Dan, "but first tell me a bit about what I'll find."

"It's sparse and just growing on my mound. I don't know what else to add."

"Then put on a loose skirt, with no panties, provide me with the necessary tools, and I'll set to work. Just promise me you'll keep your knees touching each other. I don't want to be distracted. We'll save that for another day."

"Dan, do you realize you are driving me crazy with my desire for you?"

"I'm sure my desire matches yours, but you've confirmed our slow progress is leaving you with no insecurities or confusion, and that is my priority. After each step, we both feel more assured that we belong together."

"OK, Dan, I appreciate the way you take me by the hand and introduce me to this scary, overwhelming yet very desirable concept of love. You've helped me to not question whether I measure up or might be doing something wrong. My wondering is about future sharing, but I feel no doubt about anything we've already shared. It just seems like we are traveling at a snail's pace. I do see progress, and realize we've come a long way, but I want you so badly. I long to experience us blending together as one, believing the blending will only add to each of us as individuals, subtracting nothing. Each time you leave, I am left with this pent up energy that requires masturbation to be released. The explosions I experience are so much more intense than anything I experienced before you first placed your lips on mine. I'll go along with your guidelines, today, as long as you agree to spend the night with me this Friday. I need to finally experience falling asleep in your arms."

"You've got a deal," Dan said with a smile.

Cindy bounced off to her bedroom to prepare herself. "I'm ready," she called from her bathroom. When he arrived in the bathroom, he found Cindy sitting on the counter, wearing a sweater and knee length skirt. "I was tempted to go topless, but Mr. Wonderful, here, doesn't want to be distracted. Is this conservative enough?"

"Cindy, when I see or think of you, the last word that pops into my mind is conservative. I look at your sun-streaked brown hair flowing with its many caressing fingers of love, your sparkling eyes, your impish grin and I feel energized beyond words."

"OK, Doctor, I'll leave you to your surgery and do my best not to distract you." She leaned back and closed her eyes. Dan ran his hands firmly up the sides of her legs, lifting her skirt as he progressed. When her mound was revealed, Cindy let out a gasp. Cindy felt his gaze on her face and said, "I know, I know, I'll try harder."

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