Chapter 1: What a First Date is Like

Rebecca stared at her lithe, 5’4, fair skinned reflection in the full body mirror of her room. Her teeth biting her lower lip as she moved her head, causing her long dirty blond hair to cascade down the shoulders of her white sunflower dress.

Tugging upwards on the front of the dress to cover the bountiful cleavage of her 36DD breasts, she sighed despondently and shook her head. Nervously glancing at her clock, she took a deep breath and whispered as she rubbed her temples, “Still have time.”

Her face hardened slightly as she inwardly berated herself, ‘Just a first date, it’s not that big of a deal.’ She grabbed the hem of her dress and pulled it over her head, leaving her in only a pair of white cotton panties and bra. Tossing the dress onto her bed, she reached into her closet and grabbed an oversized grey hoodie and a pair of ripped black jeans.

Slipping this new choice of clothes on, she looked at her reflection and instantly felt a bit more comfortable and calm. Old habits were always a challenge to get rid of and years of being chubby and uncomfortable with her own body still haunted her. Even after an entire year, she still could not quite shake her former mindset.

Off in the corner of the room, in the doorway stood a tall young man with short brown hair and short, trimmed facial hair. He had been there for the past few minutes and had watched as his sister changed outfits four separate times before she seemed to finally settle on one.

Inwardly, Jacob disapproved of his sister’s choice of clothing, finding it a shame that she was hiding her attractive body. However he held back his thoughts, finding it not quite appropriate for him to say. Instead he simply walked forward to Rebecca who sat down on her bed with her eyes closed as she played with the sleeve of her sweater, seemingly fantasizing about something.

She did not notice as her brother approached, his bare feet making almost no noise on the hardwood floor as he finally stood in front of her. Abruptly, he bent down and placed his hands on her shoulders as he lightly said, “Hey Rebecca.”

She gave a cute yelp and jumped a little while her eyelids snapped open; her shaky azure eyes stared into her brother’s amber eyes. “Asshole.” She teased with a giggle as she innocently stared at her older brother, completely unaware that he was watching the entire time as she nervously changed.

“What’s up? I thought you were going to hang out with your friends today? Didn’t realise you were still home.” Rebecca scooted back on her bed as she spoke, sitting down in the lotus position as she leaned back on the wall. She looked at him, nibbling on the inside of her cheeks and still playing with her sleeve.

Jacob smiled as sweetly as he could to mask his mild irritation at having his plans fall through for the night, “I had to make sure my little sister would have a great first date. It’s my duty as a brother.” His irritation only grew mildly at the thought about her date with Chris. He felt as if his innocent little sister was being taken out into the wide world without him, and that irked him the wrong way.

Rebecca blushed with a soft laugh, waving dismissively, “You didn’t have to cancel your plans for me, silly. I’m a big girl, I can handle getting ready for my date with Chris by myself.”

In Jacob’s mind, Chris was a feeble and nervous guy, quite similar in disposition to his little sister. The truth was that it had come as a massive shock that he had even found the courage to ask her out on a date. ‘That brat actually somehow found the courage to try and steal my little sister.’

None of Jacob’s inner thoughts showed as he put on a teasing face and crawled onto the bed, sitting beside Rebecca, “My cute little sister has to be ready for the world of dating. What about you? Why are you getting ready so early? Nervous, are you?”

Rebecca moved over slightly, giving Jacob more room to comfortably sit as her face burned with embarrassment, “I am nervous,” She looked to her fidgeting hands and spoke shakily, “I can’t help it! I mean, last year, no one wanted anything to do with me, you know? I was invisible and I-I mean I just kinda got used to it. But now, after I lost all that weight, guys are flirting with me and I-I don’t know, it’s just weird. I don’t know what to do. I was so happy when Chris asked me out, I mean, I always thought he was cute, but-but I don’t know what I am doing. Like, what do I talk about? What do I wear? What if he tries to-to touch me?”

Rebecca rambled quickly, stammering through her anxiety with a bright red face, “I just-just want it all to go well, you know? I don’t want to mess things up.” Rebecca finally stopped talking, giving Jacob a chance to speak as she brought her eyes up from her hectic hands up to look at his face.

Jacob couldn’t hold back a bolt of laughter that escaped his lips at her rapid fire questions, especially after her last question, “Chris touching you? Yea right, he might have grown balls big enough to ask you out but he would never cop a feel. Besides, even if he did, I would just break his hand. Only I can cop a feel.”

Jacob’s laughing words abruptly froze as he realized what words had just escaped his lips. He stared strongly into his little sister’s bright blue eyes and found no revulsion at the thought; feeling almost as if it was not only his right, but his duty as well. Coming to terms with that, he felt as though a switch was flipped in his mind and after a short pause, he mildly asked, “What would you do if he did cop a feel though?”

She let him tease her with his words, used to it and not giving it much thought until his final question which surprised her. She looked back down to her fidgeting hands as her cheeks continued to burn, “I-I don’t know, honestly. No one’s ever tred. I mean, I-I kissed a guy once, in the fifth grade, but I-I’ve never done anything else.” Rebecca scrunched up her burning face as she realized she just inadvertently confessed her virginity to her brother.

Jacob found himself surprisingly irritated that his sister had already kissed someone and scooted towards her, almost touching her head with his face. His voice was teasing, able to easily mask his irritation, “Oh yea? How did you kiss him? What was it like?” He felt the need to know just how much of his little sister was taken by someone other than him.

Jacob found a strange possessiveness growing inside him as he scooted forward, his thighs and legs touching Rebecca’s as he realized something. He wanted his sister all to himself. He wanted her to be his in every aspect. Along with that growing desire, his cock also grew semi-erect, bulging against his jeans.

Rebecca blushed as Jacob moved closer, “Don’t tease me.” She whined cutely and pulled up her legs so that her knees rested against her chest, “I dunno, we just kissed. It was the kinda kiss we used to give mom and dad when we were little. Just like this,” She made an exaggerated kissing face at him, “We didn’t use tongue or anything like that. I-I mean he tried, but I didn’t let him. It felt gross at the time.” She shook her head in denial.

Jacob felt a small modicum of his irritation fade away at her words, ‘Only an innocent kiss.’ Noticing her turtle-like position, he laughed slightly and moved in front of her, spreading his legs on either side of her and trapping her, “Gross at the time?” Jacob said in mock curiosity, “So now you don’t think it’s gross? You mean you want to kiss a guy and use your tongue to play with his mouth, swapping spit with him?”

Rebbeca felt extremely embarrassed despite the fact that she knew he was only kidding; she spoke up with as much confidence as she could, “Well, for your information, yes, yes I do. I think it would be fun.” She moved her legs forward as much as she could in Jacob’s entrapment and straightened her back, “People do it all the time in movies so there must be something good about it.”

Rebecca crossed her arms over her large chest, giving a soft and cute snort, barely containing a smile and a giggle, “Why do you even care anyways? Go away, be a loser somewhere else.” She teased with a giggle, the hot blush of her face not receding.

“There is indeed something good about it, you don’t know what you’re missing. In fact I could go for it right now.” Jacob made an exaggerated kissing face at Rebecca, “Come kiss, kiss, kiss.” He said as he made a funny kissing face, leaning forwards into her as she offered no resistance, “Come, or big bad brother will cop a feel.” He waved his fingers about in a jokingly threatening manner, holding his face between her knees.

Rebecca laughed at his antics and rolled her eyes exaggeratedly as she tried to move away, “You dork, come on, stop that and move.” In response, he only trapped her even more with his hands before she whined in defeat, unable to get away, “Fine, fine. I’ll give you a smooch, you poor lonely creature. It’s probably the most action you’ve got all summer.”

She leaned forward and gave him a quick peck on the lips before pulling away. It didn’t feel weird to her at all considering how close they had always been, “There, now will you let me go, you meanie?” She stuck out her tongue playfully at him.

Jacob laughed at the quick peck, finding much more enjoyment than he ever remembered when they treated it as a greeting when they were little. Now he was even more sure that he wanted her more than ever; he never wanted to let her go, “Never.” He said teasingly before grabbing her hands and asking offhandedly, “How much do you know about what happens on a date? Did you talk to anyone, or have you just built up fake expectations from pop culture?”

Rebecca sighed exaggeratedly at his teasing, but paused at his question, raising an eyebrow in confusion, “Well, I mean in movies, it’s sweet and romantic and people always have a fun time. Chris said he wanted to go see a movie. It’s been forever since I’ve been and I’m excited, I’m even hoping he’ll hold my hand, and maybe,” She blushed and looked away to the side into her open closet, “Maybe he will even kiss me goodnight when he drops me off.” She gave his hand a nervous squeeze.

Jacob smiled slightly, knowing that all of her information was only from fiction, “You are so innocent.” Rebecca grumbled a denial at his words but did not directly interrupt as he continued, “If all you have to go on is movies then you will be surprised when you head out tonight.”

“What do you mean?” Rebecca asked as she tilted her head and raised her eyebrow in confusion. Jacob took a short pause, choosing his words carefully as he began to craft his elaborate fabrication.

“They have to take out the real exciting parts of dates out of movies so that they can widely market those movies. If all that Chris takes at the end of tonight is a kiss, then even if he might like you a little, he is just leading you on.”

Jacob knew that Chris would probably lack even the courage to take a kiss let alone more; Jacob was taking advantage of the trust that they as siblings had built over their entire lives. Rebecca bit her bottom lip before asking gently, “But Chris is a sweet guy, I mean, he knows I’m a virgin so he won’t do anything to make me uncomfortable.” She said innocently.

“Virgin or not, if you are having a good date, there is only one way it should be going.” Jacob squeezed her hand reassuringly as he continued his lies with false sincerity, “Here, I’ll show you what I mean.” He let go of her hand and moved over to sit right next to her, looking into her eyes as he spoke, “This is what you see in the movies.” He raised his arms and paused for a moment before lowering his arm and placing it on her shoulder.

Rebecca nodded eagerly, cuddling up close to him as he explained. ‘This is not so bad.’ She thought to herself.

“However, reality is different. If he likes you and is enjoying your date, he will do this.” Jacob bent his arm down, wrapping it around Rebecca’s neck as he placed his hand on her large breast. He held her in place as he gently grabbed her breast and continued to speak as he groped her, “And that is why I asked what you would do if he copped a feel, because if the date is going well, then he should be copping a feel many times.”

When she felt his hand grab her breast, she froze before letting out a soft, barely audible whimper as her nipples quickly hardened in response, “Many times?” She bit her lower lip as a blush once more graced her cheeks as she realized Jacob was not letting go and still kneading her breast. Biting her lips to silence her soft pants and whimpers, she looked at him embarrassedly.

Her big brother was fondling her breast, but it didn’t feel wrong. After all, they were always so close and he was just preparing her for her date. The sensation still affected her, arousing her even as she internally made excuses for it.

Jacob felt his cock hardening even more as he groped his little sister’s breasts, “No, not throughout the entire movie. Guys like touching tits, but doing it continuously for an extended period is tedious. So, although he might be touching you for the entire movie, I don’t think he will be groping you for the entire movie. Groping your tits is basically a guy’s way of saying that he is enjoying your company.” He paused for a moment before realizing he might be painting himself into a corner and quickly adding, “At least for the first date that is, because depending on the relationship, the actions will change.”

Rebecca nodded as he smiled reassuringly and her eyes glazed slightly in pleasure as her cheeks flushed bright pink. His groping never ceased as he continued, “For now, we will just focus on first date etiquette. For example, if you catch him looking at you while he is groping your tit, you can show him that you are enjoying his company by giving him a deep kiss. It should be passionate and last at least a few seconds.” He never looked away from her face as he explained.

She swallowed nervously, her eyebrows furrowing as she looked away from his penetrating gaze, “But I-I’ve never really kissed a guy properly before and this-this is a big date. What if I’m not good at it and I mess up?” Rebecca sighed softly as she looked back to her caring big brother, “How do you get good at kissing anyways? I-I mean I’ve practiced on my pillow but it’s not like my pillow can tell me If i’m good or not.”

Jacob’s smile widened ever so slightly at his little sister’s plight, “Practice makes perfect, and the only way to practice something is to do it.” He paused as he contemplated his words, “Here, just pretend we are on a date right now and just try it. I’ll help you out as much as I can and we will practice to perfection.” He chuckled and added, “Or at least something close enough.”

His hand never stopped groping Rebecca’s breast, going against what he said about it being tedious. However neither of them really had the wherewithal to notice the contradiction. She nodded and took a deep breath, “Okay, I-I can do this.” Whispering, she turned to look at Jacob before looking away with a quick giggle, blushing brightly as she covered her face with her hand.

“God this is so weird. Okay, okay. I’m sorry. Let me try again.” Rebecca turned to face Jacob again, taking another deep breath while trying to trick her mind, ‘It’s not your brother. It’s Chris.’ Reaching out her trembling hands and placing them on his chest, one hand slid up to tangle in his hair as she leaned forward. Pressing her lips to his, she gave him a chaste kiss, her eyes closing as she gently parted her lips. Giving a slow and deep kiss, a soft whimper left her lips as he continued to knead her breast.

She pulled back, flicking her tongue against his lower lip as she gently moaned, “Oh Chris.” Jacob enjoyed the innocent kiss, but cringed physically as he heard his little sister call out Chris’ name. While only blaming her slightly, he instead found his irritation with Chris growing ever greater.

“Using your tongue at the end was a good idea, as for the rest of it.” He paused, pacing his words to hide his foul mood, “I can’t fault you. It being your first attempt after all. However, I’ll tell you how to do better.”

Rebecca frowned, embarrassed that she was disappointing as her face burned with shame, “Oh, I-I’m sorry.”

Hiding his irritation behind a mask of indifference, he declared, “First off, I am not Chris and you shouldn’t pretend I am or else when you see him, you will instead see me.” In his mind however he added, ‘Or even worse, you might see him when you are with me.’ He continued, “As for the kiss, you have to be more passionate with your actions. Remember, you are using your actions to respond and tell the guy that you are enjoying his company just as much as he is enjoying yours. Try again.”

Rebecca silently listened to her big brother critiquing her kissing skills and bit her lower lip. She waited until he finished his explanation before she nodded and laughed awkwardly, “Yeah, it would be kinda weird if I was kissing him and saw you. Okay, I-I think I’ve got it this time.”

Rebecca took a deep breath and tried once more, pressing her lips to his as her eyes fluttered closed and she used the groping of her tit as fuel for the passion she felt. Her lips trembled as she moaned against him, hungrily devouring his lips and swiping her tongue along his lower lip. Jacob consciously held himself back but still clenched down slightly harder on her breast. Without pause, she drew his lower lip between her teeth to nibble and suck on it, releasing it and gently flicking her tongue against his with a strangled moan.

The sensation of his lips against hers making her innocent body react, her virgin pussy pulsing with need as she slowly pulled away. Breathless, with her glistening pink lips swollen she asked hopefully with her heart pounding, “How was that?”

Jacob had to consciously hold himself back as he kept a mild demeanor, barely showing his growing arousal and hiding it behind a mentoring tone, “That was much better, but I think you are still holding back. Try once more, this time try to be as wild and passionate as you can, go crazy like an animal.”

Rebecca nodded still somewhat breathless as she took a deep breath, trying to reach inside herself to find that wild passion and unlock it. Letting out all the years of repressed sexual need, she kissed her big brother fiercely, no longer holding back and letting her shackles of innocence fall.

She grabbed his T-shirt and tugged him towards her, forcing him to lay down on her as she wrapped her arms around him; He was surprised but allowed her to act how she wanted as her tongue invaded his mouth and she ravaged his mouth with her tongue. His hand miraculously stayed on her tit, but now, his weight was bearing down on it. One of Rebecca’s hands tangled in his hair while the other clawed at his shoulder. Her tongue swirling around his before drawing it between her lips to suck it in long hard pulls.

She finally broke apart from him, her eyes glazed over with need as she blushed, “Oh, sorry. I-I kinda just lost myself for a second.” She spoke while crawling out from under him as Jacob’s arm finally left her breast.

He smiled and laughed lovingly at her glazed eyes and flushed cheeks, “It’s alright, that kinda energy would be great for sex, but for now we are still at the teasing stage.” He sat back positioning himself against the wall as Rebecca followed and sat beside him once more.

“Now you know the energy you should be bringing. Let’s try once more. What I want you to do is take that energy that you just showed me and hold it in your mind. Ball it up and using nothing but your mouth, let that energy explode out.”

Rebecca blushed with embarrassment at how overexcited she was, “Good thing I didn’t try that with Chris.” She giggled as Jacob’s eye secretly twitched, “Okay, I’m ready. I’ll get it this time for sure.”

She leaned in slowly and cupped his cheek with one hand while the other slowly threaded through his hair. Her body relaxed against him as she sighed and whimpered into the kiss, trying with all her might to pour out her passion as her tongue teased his lips. Quickly invading his mouth and doing battle with his tongue. She explored his gums, her tongue wiggling about into any crevice it could find before she finally pulled away with a smile, “I think I got it.” Rebecca bounced up and down on the bed happily, her breasts jiggling under her sweater.

Jacob laughed with her as she bounced, “Yea, I would say you got it. However, you still have lots to learn.”

Rebecca tilted her head and questioned his words, a bit of her excitement dissipating, “I do?”

Jacob continued, “Yea and I don’t want you to be taken advantage of on your first date; So, what would you do, if for example, the guy does this.” He quickly slithered his hand under her sweater and bra, looking into her eyes as he gave her bare breast a rapid couple of squeezes.

Rebecca let out a trembling gasp as her eyes widened. She quickly tugged away and slapped his hand away, “H-hey.” She bit her lip to keep it from trembling, “You-you gotta warn me.”

Jacob felt equal parts sadness and excitement at her reaction as he quickly formulated his response, “You won’t get any warning in reality. But at least you know where to draw the line. That kind of brazen action is at least reserved for the second date, most certainly not the first. However if a guy does that on the first date, you had better react more strongly. I’ll only let it go because you are practicing with me.” Jacob kept his calm exterior as he adjusted himself, hiding his almost completely hard cock.

Rebecca just shook her head, mumbling, “Chris wouldn’t, he’s-he’s respectful.” She looked down to her hands which were once more fidgeting when Jacob rested his arm on her shoulder anew.

“On a first date, what do you think happens after the movie Rebecca, after you both show that you enjoy each other’s company?” He lifted her chin, her meek eyes locking with his in response.

“Um, he-he drops me off at home?” She spoke questioningly, “Then we go on a second date next week?” Her innocence showed on her face as she looked unsure of herself, “Am I wrong? W-will he try to-to touch me like-like you did? I-I’m not sure I’m ready for that.”

Jacob continued to avoid using Chris’ name as he explained, “If your date really likes you, then after the movie he will take the initiative to give you a kiss, kind of like this.” He leaned over and held her chin, pressing his lips to her. She froze and closed her eyes, following his lead while returning the kiss, a soft whimper leaving between their entangled lips. Quickly, his tongue invaded her mouth and explored her gums and teeth before entangling her tongue.

Finally pulling back after a long moment, he continued as Rebecca’s heart pounded out of her chest, “The first date is about showing mutual attraction, then acting out a gentle passion. However after this kiss, your date will ask you for something. How he asks will change, depending on the guy but he will basically ask you to suck his cock. Are you ready for that?”

Her eyebrows furrowed slightly in worry and shook her head with a whisper, “No, I-I don’t think so. Why-why does it have to go so fast? I mean, can’t we just enjoy each other’s company. Going from kissing straight to-to that is too much.” She looked away, “Is-is that what he expects me to do? I mean, I-I don’t have to, do I?”

“Not on your first date you can’t, on later dates you can simply enjoy each other’s company if you want, but the first date is a dance of mutual attraction. If he is not acting like this, then he does not like you enough.” Jacob pulled his little sister into his body and stroked her shoulder reassuringly as she snuggled up to him. Her arm wrapped around him as she pressed her head to his chest.

“You should calm down though, it’s only a blowjob, you aren’t expected to have sex on your first date. However, like I said, this dance is about showing your attraction to each other. You don’t have to do anything, but if you enjoy your date, then you should use your actions to show that you like him.” He rested his head on hers as he comforted her with more lies.

She sighed, “It’s just-It’s not fair. I mean, I like Chris and all, but-but I don’t know. I don’t think I like him enough to do all that just yet. You know? I mean, I’d rather just get to know each other better and stuff.” Feeling hopeless, she sighed once more, “When he asked me out, he-he was staring at my chest pretty hard. He could barely look in my eyes so I guess-I guess I should’ve seen this coming.” Taking her head from under Jacob’s, she looked at him, “What do I do?”

Jacob swallowed deeply, a nervous excitement threatening to shine through, “You are only scared because you have never done it before. The best way to cure that fear is to just expose yourself and do it. Like with the kissing, you had done it years ago in fifth grade and felt grossed out by the thought of using tongue. However you slowly built up an expectation about how good it could be until finally, now, when you were looking forward to it. You just need to take the leap and do it, but it may take more practice than with the kiss.” Rebecca listened to his words silently, finding the logic in his words as he paused to let her digest them.

After a long pause, Jacob decided to push a little; he took a long breath before sighing heavily, as if to express resignation, “Fine. Fine, I’ll let you give me a blowjob to get some practice. But only because you are my lovable little sister, otherwise you would have been on your own and would have had to have had a couple dates to figure it out.” He spoke out as if what he was doing was a great favor and poorly trying to hide his apparent exacerbation.

Rebecca winced at his words and instead of refusing outright like a normal person, she apologized, “I’m sorry. I don’t mean to put you out you know? I know you’ve got better things to do. I’d appreciate the help but-but isn’t this a little far? I-I mean, I don’t want to be ungrateful, but although all siblings practice kissing at some point, this-this is.” She gestured vaguely with her hands, unsure what to say as her face burned, “I mean, I’d be-be pleasing you. Wouldn’t that be weird for you, I mean, knowing it’s me?”

“We are both full grown adults, just because you are my adorable little sister does not change that. Incest is in fact common in human biology, having an innate attraction to those you are related too. I won’t let a stupid social stigma stop me from helping out my little sister.” Rebecca felt her big brother pat her head as he continued.

“In fact that stigma was originally there because of biological incompatibility among relatives. However there is a way for humans to know if an incestuous relationship would in fact be good biologically; If someone’s natural smell is nice to you then you are biologically compatible with them.” He smiled at her with a teasing grin, “So, are we biologically compatible Rebecca?”

With widened eyes, her heart pounded as she thought about this new information; unable to think why her brother knew so much about this. It was not obvious, but even Jacob realized after he spoke that his attraction to his little sister was not something that came up out of the blue, “Um,” Rebecca stammered for a moment as she thought back to the past.

She remembered some times when her big brother came out of their home gym and realized that she always found his sweaty scent mixed with his cologne pleasant. She froze at the thought before denying it with a dismissive wave of her hand, “I-I-I mean, I dunno.”

Jacob laughed at her nervous actions, “You know the truth but you’re too embarrassed to admit it. Aren’t you just adorable.” Leaning his mouth down to her ear he whispered, his hot breath tickling her ear. She shivered and felt goosebumps rising on her skin, “I’ll tell you how I know you like my smell.” He paused, teasing her with the silence, “It’s because I find you- “ He took a languid sniff, “-positively delectable.”

She groaned in abject shame and Jacob laughed with a beaming grin, “Look Rebecca, we are brother and sister, yes, but we are also biologically compatible. So why should we adhere to an antiquated social stigma meant to protect our genes, when we know that our genes are not in danger. Just follow logic.”

“Come on,” He laughed and shook her teasingly, “I’ll teach you how to give a blowjob and I won’t find it weird, so neither should you.”

Rebecca shook slightly, feeling terrible and filled with shame; Jacob’s laughing making it worse, as if he was laughing at her. She shook her head and pulled away, “You-You’re actually arguing for this?” Quirking her eyebrow, she sighed, “I-I-This is making me feel weird.” The fact that her big brother seemed so cavalier about this only increased her worry and confusion. Fidgeting, she wondered if she was the odd one; did other siblings do this?

“I’ll, um, take a raincheck I think.” Trying to gently reject him, she moved as if to get up from the bed when Jacob quickly grabbed her shoulder and pulled her back into his chest.

“Not a chance girly.” She yelped in surprise, her heart hammering wildly against her chest as she was forcefully held, “Since it has already come to this, if I didn’t help you, you would be clueless. And I won’t let you make a fool of yourself, especially not after I decided to help. So, since I am helping, I’ ll make sure you’re prepared properly.”