Chapter 4: A First Date

Parking in the lot in front of the mall, they both left the car, locking it behind them. Rebecca quickly fell into step beside Jacob as she nervously reached out to take his hand, looking up and searching his face for confirmation that this was okay. He merely glanced back with a smile and nodded reassuringly at her probe, gripping her hand lightly in his. Giggling in nervous excitement, she asked, “Which store are we going to first big br-” She quickly stopped and corrected herself, “Jacob.” She blushed deeply knowing that he was her boyfriend right now, not just her brother.

“Well Rebecca, we’ll start with casual clothes for home and for dates. I want you to pick out something that you like, so you will pick out some clothes and I will tell you if I approved once you try it on. Just don’t forget that you are not just shopping for yourself anymore.”

Nodding, Rebecca listened to his words before he led them into a larger store with multiple styles. She was more used to baggy clothes from cheaper stores that she used to cover her insecurities, but now she knew that things like that would no longer be permitted; she represented her boyfriend and she needed to look good for him. Releasing his hand, she wandered over to the petite section, looking through the racks of clothing. Picking out a cute top, she looked nervously at Jacob, “Um is this-”

He quickly interrupted her and grabbed the top with a smile, “Pick out some clothes first and then I will tell you what I think once you try them on.” She blushed and nodded, picking out a few more bits of clothing, and even snagging some skirts and dresses.They were nothing like what she would usually wear, but she was not stupid, she still understood what looked good; it was just a question of if it looked good on her.

Jacob followed with a smile as Rebecca made her way to the changing rooms, his arms full with clothes. Depositing the clothing in the room with Rebecca, Jacob smiled, “Try on an outfit first, I have to go check up on something quickly.”

Rebecca nodded sweetly and closed the door as he left. He quickly made his way to a slightly more risque department and picked up a sexy red lace top and a pair of short short jeans. Holding it behind his back, he made his way back to the changing rooms just in time to see Rebecca emerge in a cute, white lacy top coupled with a black pencil skirt. Seeing her big brother, she smiled and twirled, feeling sexy in the tight outfit, “How does this look?”

Nodding approvingly as she showed off for him, he walked to her, “You look great! I approve” Glancing around discreetly, noticing nobody around, he wrapped an arm around her shoulder, still hiding the red top and shorts behind his back as he led her back into the changing room.

“What are you hiding behind your b-” Rebecca was in the middle of voicing her curiosity when she moaned as Jacob groped her tit. She quickly covered her mouth with both hands to keep herself quiet before slapping his hand away quickly, “W-what are you doing? W-we’re in public, someone could hear us.” Blushing and admonishing in a hushed whisper, she already felt her body heating up at his touch.

He scowled lightly as if to voice his displeasure, “Then you should hold back your moan of pleasure. I can’t help it if you get horny from just a simple squeeze of my hand on your tit.” He led her forcefully into the changing room, locking the door behind him as he reached around her shoulder again; This time squeezing harder on her tit and keeping his hand in place even while she whimpered. His voice was tinged with a pitiful sadness, as if his displeasure had passed to be replaced with a face of deep anguish, “Are you really not enjoying my company?”

Seeing the sadness overcoming his face, Rebecca felt a pang of guilt sting her heart, “Of course I’m enjoying your company! I-I love being around you. W-what did I do wrong?” She asked innocently, “I-I thought we were having fun, please, just-just tell me what I did wrong.” She begged quiveringly as she looked up to him, her hand nervous in front of her.

Jacob stuck to his guns, quickly coming up with some logic behind his actions, “I’m showing that I’m enjoying our date and your company.” He squeezed slightly harder onto her breast, eliciting a groan through grit teeth from her, “But you pushed me away. Am I only good for you when we are in the privacy of our house, or our car? Do you not want to show your love for me when we are not alone.” He sighed despondently, explaining his convoluted reasoning, “I mean I could understand slapping my hand away if this was not our first date, but you don’t even want to show our mutual attraction in public.”

Blushing, she quickly shook her head, “No, no, that’s not it at all! I just-your touch, it-it makes me ache and I-” She looked down, feeling self conscious, “I’m embarrassed to get turned on in public. I mean, I-I can’t get these clothes wet before we buy them. I want you, always, I swear. I’m so sorry. How do I make it up to you?” Rebecca rambled on, feeling nervous that she had upset or hurt her loving big brother. She felt as if she was such an ungrateful bitch to always cause him harm.

“You worry too much about things that don’t matter.” He reached down and undid her pencil skirt deftly with one hand, letting it fall to the ground to reveal her panties as his other hand held the clothing behind her back. Holding her strongly to his chest with one arm, he sent the other to her vagina. She gasped and quivered beneath his touch as she felt his fingers start rubbing her pussy through her panties, “You should ache for me, even when we are in public and you should not worry about getting the clothes wet. Your panties are there to soak up some of your arousal and even if I don’t buy the clothes, someone else will enjoy your scent on them.”

“I-I do ache for you Jacob, so much.” Rebecca blushed deeply, feeling her embarrassment overpowered by the ache in her pussy and immediately started to feel her panties wet beneath his fingers. Stepping on her tiptoes, she gave him a quick kiss on the lips, looking at him imploringly, “I’ll do better, I promise! Just-Just tell me what to do and I’ll do it.” Begging, she had heard the fake disappointment in his voice and believed with all her being that it was real.

“I guess this is just another thing I have to teach you. “ He gave her lips a quick peck in return, “I can’t fault you for not knowing the proper procedure. I am just sad that you did not trust me enough to go against your initial thoughts and fears. Do you really think how I taught you to act was wrong? You can make it up to me by just trusting me, but in the meantime, I’ll help you get over your fears.”

Hanging the cold metal hangers on the back of her lacy top, she shivered and softly gasped as he continued to rub her pussy. “You are scared of getting horny and aching for me in public, so that is exactly what you are going to have to do.” Taking his now free hand, he placed it over her eyes, blinding her, “We will conquer your fears today. I’ll tell you what though, if you are a good girl and face them head on, then maybe I will reward you with an orgasm when we are going home. But for now, my sweet little girlfriend, tell me how you feel, spill your heart out so that I know how to help you.”

Shivering and blushing bright red, Rebecca wondered, her sight gone, leaving her almost completely filled with thoughts of her big brother. The sound of his voice, the touch of his fingers on her pussy, the feeling of warmth his strong body provided, and even the taste of his tongue and the smell of his entire being.

She panted slightly, her pussy throbbing at his touch, “Well, I-I’m excited, about being your secretary and getting new clothes, and-and of being here with you, and I like dressing up for you. I-I like being able to show off for you. Um, and I liked it when I got to hold your hand, I just-I’m not used to this kinda thing, especially in public. I was always told that’s the kind of stuff you save for when you’re in private, and I-I worried someone knows who we are might see. I mean, a-” She blushed deeper as his fingers became faster, “A brother and sister holding hands is one thing but-but the other stuff.” She kept her voice low, “Like you said, society would not approve.”

Pushing her slowly against the wall, holding her there steadily with his hands and chest as she whimpered, he gave her a quick but passionate kiss, slipping his tongue inside her mouth for a quick moment. Rebecca whined softly in need as her hips rocked against his skilled hand. “Jacob.”

“Rebecca, I don’t care who sees us, because if we can’t show our appreciation and love for each other in public, then what is the point of life? Of course we have to be more conservative in public but that does not mean we can’t show our love. I will protect you.” He brought his head to her ear and gave her earlobe a playful nibble, whispering right into her ear with his hot breath, “Your big brother will protect you, and I will do whatever is necessary to protect us and our happiness.”

Goosebumps rose on her skin as he whispered into her ear and her knees felt weak, “I-I love you.” Whispering those words caused her to flush bright red and tremble. She had said those words countless times throughout their lives, but this time felt far different, “Please. I-I love you. I will do anything to make you happy.” Reaching her hands up, she blindly gripped his shoulders and smiled softly, massaging them lightly, “You look after me so well and I-I feel so safe with you.”

Jacob acutely felt the strain of his cock in his pants as he looked down. He took a deep breath and stepped back, stopping his rubbing of his little sister’s pussy and bringing his wet fingers up to her face in front of her lips, letting her smell her arousal, “I love you too Rebecca. I just want you to be happy and strong. So if you help me, help you, then you’ll have made me happy.” Taking his hand from her eyes and returning it to her back, he revealed his face showing an extreme tenderness.

Trembling at his words, Rebecca whispered weakly, “I-I’ll try to make sure I do everything I can to make you happy.” Gazing at his fingers wet with her arousal, she glanced at his eyes as she brought her delicate hands to his and whimpered softly, licking the juices from the tips of his fingers and sucking them clean. The action caused an extra pulse between her thighs and she felt her heart race. The look of tenderness on his face made her swell with devotion, “S-should I try on some of the other outfits now?”

“Yes.” Jacob gave her a quick kiss, taking hold of the slight tang of her arousal on her lips, “Let’s see what other outfits are able to show off your beauty.” Reaching behind her, he picked up the hangers from her back and quickly hid it behind his back, letting Rebecca catch nothing but a glimpse of red and light blue as he backed up, sandwiching it between his back and the wall

Rebecca now had ample room to change in the cramped room, but had no privacy as Jacob blatantly watched her. She tried on several pieces of clothing, some more conservative yet cute for days she would go out without her strong protector and some sexier ones for their dates when she would be on his arm. Nothing was too out there though; even though she was trying, her old habits could not be destroyed in one day.

She even tried on some professional outfits with a few stockings, preparing for when she would be her big brother’s secretary. Most of the articles of clothing received approval from Jacob and even though she had tried her hardest to pick ones that he would approve of, some still got rejected, “Well I think that does it.” Rebecca had long forgotten about the blur of red and blue that her big brother had hidden behind his back.

Smiling lightly, she got out of the last outfit and was wearing only her bra and still damp panties; Jacob suddenly stopped her as she was about to change back into her own clothes, a little tease in his voice, “Not quite. You still have to try these on.” Smirking, he exposed the hidden red top and short short jeans from behind his back, he held it up for her, watching as she widened her eyes. She had never worn something like it and all of her insecurities nagged at her in the back of her mind. However she still hesitantly took the small pieces of clothing from him all the same and slowly slipped it on.

The top was a small red off the shoulder crop top that fit snugly over Rebecca’s large breasts. Her face burned as she tugged down, her breasts straining against the lace and leaving little to the imagination. The intricate lace barely covered her chest and hung loosely off of her mounds, exposing her midriff and the underside of her white bra. The shorts were a pair of faded blue, torn short short jeans that barely covered half of her ass.

The outfit seemed to be on the edge of being slutty but not quite there, instead conveying a sense of elegant carnality, “Um-how-how do you like it on-on me?” She fidgeted nervously, searching his expression and wondering if he had suggested this top so that he could devour her with his eyes. The thought caused her heart to pound and he stepped forward with a joyous smile.

Giving her a quick kiss, Jacob ran his hands around the sides of her bare torso, “It looks even more beautiful on you than I imagined.” His eyes went back to admiring the frilly lace top as it stuck tightly to her breasts, the elegant lace guiding the motion of his eyes.

Giggling softly as he admired her, she sighed in pleasure as she felt his hands slide on her, “So-so this is one of the outfits I’m only to wear for-for you, I assume?” Teasing slightly, she giggled cutely, “I imagine if I walked out of the house like this without you, I’d have to keep a baseball bat with me at all times.”

Laughing with her, one of his hands reached down and slithered down under her panties and pressed deeply under her tight shorts, finding her pussy and rubbing it. She gasped and moaned as her hips rocked into his fingers as they rubbed her wet slit, “Oh no, not a baseball bat, without me, you would need at least a bazooka, maybe even two of them.” He massaged her pussy strongly as he teased, “With your hot body and this sexy top, you might even need one for me because even I have trouble holding back.” Leaning down, he nibbled at her ear, roughly pleasuring her pussy and clit, “I might just lose control of myself and eat you up.”

Giggling between panting moans, Rebecca opened her eyes to looked needily at him, “Well, I-I guess I’ll just have to keep this top on around you then. I-I love it when you t-touch me and-” She bit her lip as she blushed and moaned softly, “When you lick me, I-I want to feel your fingers inside me, big brother...” She begged, bucking her hips against him urgently as she kissed his neck, holding herself close to him.

Blowing into her ear, he whispered roughly, “Well then, you will have to be a good girl if you want that.” He leaned back and pulled his hand out of her crotch to her obvious chagrin. Hovering his obviously wet fingers in front of her face as he smirked, he knew that her frustration would only build throughout the day, “You will only get to feel that pleasure if you show me that you can be a really good girl.”

She whined pitifully and pouted cutely as she quickly licked his wet fingers until he cleaned them of her juices. It was becoming almost like second nature to taste her pussy juices. Looking up to him, she bit her lip needily as she pressed her body up against his with an excited voice, “I’ll be a good girl, I will! I’ll be such a good girl for you big brother, you’ll see!” Giggling with youthful energy, she asked, “And when I start working for you, I’ll make you so proud!”

Jacob found himself infected with her vivacious energy and he couldn’t help but tickle her neck with his fingers, now wet with her saliva. Eliciting another bout of giggling from Rebecca as she writhed, he smiled, “You will start working for me soon then. I’m sure you’ll make me proud with your hard work and determination. Come on and change, we still have a few stores to go to before we can go home. So there will be plenty of time to show how good of a girl you are.”

Nodding quickly, she changed back into her own clothes and grabbed all of the hangers of clothes that Jacob had approved of. He followed her as she walked out of the changing room to the counter and stood back, blushing as her big brother paid. She felt like he was so sweet for paying for her clothes that certainly were not cheap. Cuddling up to him as he took back his credit card for the cashier, she ignored the consequences of being affectionate with him in front of a stranger and reached up to kiss him on the cheek, “Thank you.”

Smirking at the public display of affection, he reached behind her and wrapped his arm around her waist, “You are very welcome, my little cutie.” Jacob could still feel the invisible pain from his wallet as he put it away while Rebecca grabbed the bags and walked with him out of the store. She asked where they were going next and he held her tightly while responding, “Next, we have to get you some proper footwear. Something that will show off your beauty. Do you know where we could find that?”

Walking alongside him, she enjoyed his warmth while wondering, glancing every which way at the different stores, “Hmm.” She mumbled and looked at the footwear stores, thinking that they were not what her big brother wanted before seeing a female footwear shop and pausing, “A-are you going to make me wear high heels?” Blushing, she bit her lower lip, having only worn heels once to prom. Even then the heels were very small, perhaps less than one inch.

“Of course silly, how else are we going to show off your beauty? But I’ll still let you pick which ones you want.” He followed her line of sight and chuckled, leading her into the store after noticing the very feminine style of the storefront. He knew that his sister was prone to wear more functional footwear. Even her fashionable ones were on the moderately styled side.

Together they wandered the aisles of shoes and Rebecca quickly reached out for a pair of black mary janes which Jacob promptly refused, not even letting her touch them. With an embarrassed blush, she kept going before picking up a pair of black one inch heels and showing them to Jacob. She did not even get to ask before Jacob refused her again. With a groan and renewed sense of shame, she put the shoes back before grabbing a pair of red, two inch heels, “What about these?”

Jacob looked at them and relented, “Alright, try them on and we will see.” She relaxed slightly, thinking that she might have found a pair he liked and quickly put them on and shakily stood up to model them. She wobbled a little, feeling completely off balance but knowing that the heels probably made her legs and ass look even better. Biting her lip, she watched as he frowned slightly, and her heart began falling. Jacob narrowed eyes and shook his head lightly, “Try something else that has a bigger heel. These are not good enough to show off your beauty.”

Sighing, Rebecca stepped out of the shoes, “Um, O-okay.” Wandering around for another few moments, she picked up a pair of two and a half inch heels and quickly tried them on, standing up shakily as she modeled them. Her face turned a light shade of pink, hoping desperately that these were tall enough.

Jacob watched with a scrunched up face, taking a long moment to contemplate as his little sister wobbled unsteadily in her heels. He knew she was rapidly approaching her limit but he still encouraged her with soft eyes, “Try on a bigger pair.”

Frowning with a nervous sigh, she saw the encouragement in his eyes and felt her dread abate somewhat. She put on a pair of bright blue three inch heels, wincing as she struggled to stand up and model them for him. Pain cramped her toes and heels, but she struggled through the pain, looking to her big brother with hope as she unsteadily walked at a snail’s pace, “Jacob I-I don’t think I can wear anything bigger. These-these hurt a lot.”

Stepping to her, he lightly stroked her face soothingly, the heels still not letting her face rise even with his, “I know sweetie, I know. It hurts because you are not used to wearing them. If you wore bigger ones, you would look absolutely stunning, but even in just these, you still look beautiful.” He gave her a little peck on the lips as he pulled you into his chest, stroking her back soothingly, “You have to endure this pain and for now, let’s find some more pairs like this one. I know you can endure this, I wouldn’t push you further than you could take it.” He took her hand into his and squeezed it reassuringly while looking into her eyes with a smile.

“I’ll try for you.” Nodding as he spoke, she disliked the shoes already, never having been good with pain. However with her big brother there holding her hand, it made it a little easier. At least with this, she felt as if her pain was worth something. They wandered about the store looking for a couple more pairs of heels in the same size as she modeled each one. After picking up a few pairs, Rebecca put on her old shoes and was ready to leave when Jacob told her to sit down and wait for him to come back.

She blushed and obeyed with a nod, feeling like a child waiting for her parents as she looked around idly. After a few minutes, Jacob came back with a large box. Showing them to Rebecca, she widened both her eyes and mouth, knowing there would be no way she would be able to walk in them. They were a pair of sexy black gladiator style stiletto boots with eight inch heels, “G-god Jacob, these-these are basically stilts.” She looked up to him, and he gave a serious look, telling her to try them on. Shaking her head with a soft sigh, she took off her shoes once more and slipped her bare feet into the new shoes; lacing up the thin, crisscrossing and interweaing straps, they ended up lacing up to just under her knee and she grabbed onto Jacob’s extended hands.

Holding on desperately for balance, she could barely stand, “Whoa, whoa!” Wiggling and looking at him, now only a bit shorter than him, she pouted, “I don’t think I can do this. I-with my luck I’ll break my ankle.” She placed her hands on his shoulders as he put his hands on her hips.

Glancing down, he loved the way they looked and gave her a deep kiss, teasing her gums with his tongue. He excitedly stated, “You are absolutely stunning. I don’t expect you to wear these when we go out just yet, but we are buying them. I want you to work towards being able to wear them so I want you to try these on at home whenever you get the chance. Just sit with them and get used to being sexy while wearing them before you even try walking with them.”

Wiggling her lower lip between her teeth at his words, she wondered at the fact that her big brother really liked her wearing something like this. Nodding with a soft sigh, she blushed minutely, “I mean. I can try.” Jacob gently helped her sit back down and let her put her old shoes back on.

“That is all I ask, that you try and become the best that you can be. I will take care of the rest.” Picking up the boxes, Jacob brought them to the cashier and paid for them, feeling another sting in his wallet as Rebecca blushed at his generosity. Exiting the store while the both of them carry bags, Jacob sat down on a bench in between the stores while Rebecca followed his lead and sat beside him, “Let’s take a quick break before we take these bags to the car and go to the last store.”

Wrapping one arm around her waist, Jacob placed some bags strategically to conceal her groin, “I told you earlier that you should ignore your fear and ache for me, even in public and should not worry about getting wet. Well, we can’t get much more public than this.” He motioned to the environment around them.

Rebecca raised an eyebrow, feeling her heart start to pound at what he could mean, “Jacob, what-” Her eyes abruptly widened and she shut up. She could feel him scoot closer and slither her hand onto her pussy, massaging it over her jeans.

“So let’s start facing your fear.” The bags obscured his hand as he massaged her, making it invisible to the passerby’s eyes, but her reactions to his touch however were not. He whispered into her ear, “You have to try and control yourself, we are in public after all.”

Goosebumps rose on her skin as she felt the pressure of his hand between her thighs, “Fuck. I-I’m trying.” She blushed bright red as she barely whispered and grinded her hips against his hand.

She bit her lips and felt her body burn with embarrassment as he admonished her, “You’ll have to try harder because everyone is walking by and glancing at you. What do you think everyone else thinks, seeing you acting like this, blushing and grinding against my hand.” He whispered softly into her ear, tickling it with his breath while secretly giving a death glare at any passerby that dared to look at them. Most of them quickly looked away when they noticed his glare, “Look at them, looking away so quickly. They know what is happening and they are embarrassed.”

Blushing deeply, Rebecca’s body trembled as her eyes scanned the crowd, watching as people quickly averted their gaze, “I-I’m sorry. I’m-I’m trying so hard.” Whispering between soft pants, she ceased her hip movements, trying her best to keep still as her big brother rubbed her sensitive and aching slit beneath her jeans. She felt herself reaching a rapidly approaching climax and quickly gripped his knee, “B-big-Jacob, please. I-if you keep d-doing that, I’ll cum.” She panicked as she tried her best to keep a neutral expression, her heart pounding in her ears as her eyes and hips shook.

Jacob slowly ceased his movements, taking his hand away as he whispered his hot breath into her ear, “It’s good you told me, because I did say that you would get that pleasure only if you were a good girl, and the day is not yet done.” He took his hand away and stood up, smirking down to his little sister, he offered his hand to help her get up, “However so far, you have been a very, very good girl. For now, we’ll just take the bags to the car and then we can make our way to the last stop.”

Blushing softly, a swell of pride filled her, “I-I did good?” Taking his hand to stand up, she blushed bright red while glancing down to her crotch. Even though it did not show, she felt self conscious, as if any moment her arousal would wet her jeans. She held Jacob’s hand and covered her crotch with bags as they walked out of the mall, depositing all the bags, “Where are we going next?”

Smirking, he winked at her, “Underwear and lingerie.” They walked back into the mall while holding hands and Rebecca glowed with nervous excitement, “I-I’ve never been in a real lingerie store before.” She glanced back at the car packed with her new clothes and she felt excitement twist her stomach even more, thinking about how she would wear them and make her big brother happy.

“In that case, we will enter the first one we see. It will be a surprise for us both, so let’s go crazy and buy you a bunch of different kinds. It will be a shopping spree.” Giving a kiss to her forehead and eliciting a giggle, they wandered back into the mall, entering the first lingerie shop they came across.

Rebecca’s eyes widened at the vast array of lingerie on display, most of a naughtier nature than simply something to cover one’s body, “Oh my.” Blushing, she let go of Jacob’s hand and walked over to a shelf of skimpy panties, most of them mostly see through and some even having a split in the middle, “Um.” She pointed while looking at him with a giggle, “Doesn’t that, I dunno, kinda defeat the purpose of panties? How does that cover anything?”

Jacob stepped behind her, wrapping his arms around her and letting his hand find her pussy as he started discreetly rubbing up and down her slit where the hole on the lingerie would be. Widening her eyes, she squirmed and whimpered beneath him. She felt fascinated with his uncanny ability to make her feel like a captured and scared animal while at the same time looked after and safe, “Not at all, because this is lingerie. Lingerie is meant to be more than just panties, more than just used to cover you.”

He spotted one of the two female employees in the store waltzing over and he silently and calmly signaled to her with his free hand and his face that they were alright. She smiled professionally with a nod as he leaned in and whispered into Rebecca’s ear, letting his hot breath tickle her, “Lingerie is sexy because it adds an elegance and teasing to your being, helping you embody sexiness without just being naked. That fabric is meant to act like decoration to a beautiful pair of tits and pussy, showcasing to people the prize. Remember, lingerie is not meant to cover, it’s meant to entice. You want to be sexy and enticing, don’t you?”

She licked her lips a little subconsciously as she whispered up to him, “I think I understand. I do, I-I want to look s-sexy for you, b-big brother.” She looked around, realizing her mistake but noticed there was nobody around them and Jacob was not admonishing her. She thought for a moment and reasoned that it was okay to call him her brother as long as no one heard. Glancing at the various articles of lingerie, she curiously asked, “What do you want me to wear?”