EVERYONE IN THIS STORY IS 18 YEARS OLD OR OLDER.
Kate is a college senior who is intelligent, funny, witty, caring, loveable, and very attractive. She is a natural beauty, and Kate has alluring sexuality in everything she does; with everyone she interacts, there is an attraction to her, both male and female. She made everyone feel like the most important person in her life when she was with them.
Kate is 5′ 7″ and 110 pounds with a slender frame. Her boobs are shaped nicely and are well-proportioned to her body. She wears her straw blond hair in a ponytail. She did not need to dress provocatively to attract attention, as it is easy to imagine uncovering the delicious curves beneath whatever she wears.
Kate is home on Christmas break from college. She was shocked when she first heard her 18-year-old little brother talking about his upcoming date. Kate is four years older than Jimmy and thought of him as still just a baby, in her opinion. She used to babysit him when she was in high school. Jimmy was a scrawny little kid back then, and that is how Kate still views him now in her mind. He was starting high school when she left for college.
But now Jimmy is a tall, good, looking eighteen-year-old boy. He has an athletic build but only plays backup quarterback on his high school team, and his muscular six-foot frame is due mainly to his dedication to lifting weights in the high school gym. Jimmy counts many girls among his friends, but regrettably, none are his girlfriend. He has a way of turning girls into ‘just friends and has no idea why he always ends up in the ‘friend only’ category.
The question on Kate’s mind was what Jezebel would ask out a child. But no, it wasn’t like that. Jimmy had asked out her — Samatha, a girl from his chemistry class. He hadn’t entirely expected her to say yes, but she had, and now he came to his trusted big sister with questions. Questions about how to dress, act, and talk. Jimmy knew she would have the answers because she was a gorgeous young woman who had always had boys begging her to go out with them.
Jimmy had always viewed his big sister as a tall, sexy slender blond with tits that caught everyone’s attention. Her body is so well-proportioned she works as a model while attending college. Jimmy kept a secret stash of pictures of his sister modeling swimwear. By the time Jimmy hit puberty, he was already aware of how beautiful his older sister was, and he was drawn to her tits immediately, even though she was his sister. Jimmy secretly lusted after his big sister knowing it was wrong.
When Jimmy approached Kate with dating questions, she didn’t hesitate to answer his questions, and he took copious notes on Kate’s answers. Kate was impressed with his tenacity, and she had to admit that Jimmy wasn’t a baby anymore; he was a teenage boy bordering on becoming a man and more thoughtful and mature than some she’d dated herself. In Kate’s opinion, he was almost ready to date. Almost. But he still stuttered, fidgeted, and was still nervous. Kate wasn’t going to let that bird out of the nest and wouldn’t throw him to the other girl wolves until she was 100% certain.
That led her straight to a plan: a practice date. Kate decided they would roleplay a couple going on their first date. She told Jimmy they would use the kitchen table as a make-believe restaurant after everyone else had gone to bed. It was just roleplaying, so they wouldn’t actually go out together. But they did dress up.
As Jimmy stepped out of his bedroom, he was still arranging his tie. He wore neatly pressed slacks and a tucked-in button shirt, simple but classic. The shirt and slacks helped his blue tie stand out and emphasized how well it matched his eyes. He’d brushed out his usually-disheveled light brown hair, showing that he could tame it. Kate thought her little brother looked handsome. When she’d been his age, she wouldn’t have minded dating a boy who put in that kind of effort, who cleaned up that nicely. And she noticed that his cute blue eyes went wide when he saw her.
“D-Did you really have to wear that dress?” Jimmy grumbled.
Kate arched an eyebrow at him, hands on her hips.
“First lesson, little brother: you don’t greet your date by asking her, ‘did you have to wear that dress? Come on, try again.”
Jimmy whined like a puppy, but he knew what he was supposed to do.
“You look great, Kate. That dress is very…” He struggled for the right word. ” flattering.”
Damn, right it was. It was Kate’s favorite little black dress, and it hugged her hips, had a scooping neckline, and stopped just above her knees. She twirled her way toward him.
“Much better. And yes, I had to dress like this. If this Samatha is as into you as she should be, she’ll dress like this also. You need to be able to handle the sight of a girl’s cleavage.”
Jimmy blushed at the mention of cleavage and hurried ahead of Kate to pull her chair out.
“Not cleavage like yours,” Jimmy smiled, “Samatha isn’t that b-busty.”
Her sweet little brother noticed how busty she was. Kate wasn’t sure quite how she should feel about that, but she found it put a grin on her face as she settled into her seat.
“Okay, Jimmy, if you can chill out about my boobs, you can definitely chill out about hers.”
Jimmy pouted behind his blush as he sat opposite Kate.
“A date isn’t just about boobs,” Jimmy said, “It’s about spending quality time together and getting to know each other. Or that’s what the dating website said.”
Kate had to laugh. So conscientious. Of course, Jimmy had done his research, and she expected he would.
“Well, that website is right. So go on, get to know me.” Kate grinned. “The best dates are basically a tug-of-war where you’re both trying to get each other to keep talking. It’s good to ask about her interests to get things started.”
“Alright.” He smiled at his sister and asked, “Have you had any good modeling jobs lately?”
Oh, that wasn’t fair. Jimmy already knew Kate loved her modeling work. But it still worked. With his encouragement, she launched into stories about the new spring fashion lines that are gaining a lot of attention for her in the fashion industry. Other modeling agencies are contacting her and offering more lucrative contracts. And Jimmy listened, his eyes bright and engaged. He asked questions — he even got her to go back and elaborate about the time she had a costume malfunction in front of a hoard of reporters. Kate admitted that it had been embarrassing but fun. Eventually, she had to stop to get a sip of water.
“Okay, so you’re not bad at listening. But you need to be ready to talk too.” She grinned like she was about to take vengeance. “How’s your search for a football scholarship going? I understand some big schools have contacted you with offers.”
Jimmy took a bit more prodding; he wasn’t used to talking openly about his football skills. He knew he was a gifted athlete but often got embarrassed when people made a big deal of his prowess on the football field. Jimmy would rather have people applaud him for his high academic achievements. But as Kate prodded him about his athletic skills, he gained momentum and grew animated. It was beautiful to see. He spoke about how his teammates acted in concert to make him look good, even though he was only the backup quarterback. Kate didn’t like hearing him dismiss his football skills, but the way he talked drew her in. She leaned in closer, just as engaged as he was. Then his words started to stumble as his eyes began to slip. Kate didn’t need to follow his gaze to know where her little brother was looking. She giggled, but she also felt a faint blush on her cheeks. Her little brother was looking right at her boobs. But… It’s okay, she told herself. It’s just looking.
Emboldened, she adjusted herself a little to show off better. Most of her hair was bound up in a French pleat, but she had two locks left free — one of natural light blond and one from her blue-dyed streak. That was a fad going on at her college right now. She nudged them to fall directly in front of her chest, framing it while she leaned more fully forward and said, “I’m sorry, little brother. Am I distracting you?”
Jimmy grumbled, pulling his eyes off her and onto the wall.
“No fair. Putting things in front of me that I’m not allowed to look at.”
“It’s not that you’re not allowed to look, Jimmy.” She poked his shoulder with her fist. “You’re not allowed to stare. It’s about balance. Look at my face, my chest, the wall, or your glass or whatever. But don’t just stare at one place. Girls get uncomfortable when you gawk at their tits.”
Jimmy’s eyes widened. He took that as explicit permission to look at his big sister’s cleavage. Even if she was his sister, that was a siren song no teenage boy could resist. At first, his balance was off, and he stared solidly for seconds, and Kate cautioned him again. But eventually, he got past that, and looking at her body became a component of their pseudo-date. They chatted, they drank, and her little brother sometimes looked at her tantalizing boobs. Just enough that she could feel his boyish attraction, could know he liked her body, and strangely that was a nice feeling. Kate was a beautiful woman, and her brother knew it. Kate had fun. If she’d had a date like this with any other boy, he’d surely get a second date. But when Jimmy yawned three times in one sentence, she knew they should call it quits.
“Okay, okay,” she said. “I think it’s time for you to practice walking me to my door.”
Jimmy’s smile widened as he giggled to himself, looking past her to the hallway. “What, like your bedroom door?” He asked.
She wrinkled her nose, poked out her tongue, and snickered, “For this roleplay, we will pretend it is the front door to my home.
“Are we really going to roleplay at your bedroom door what is supposed to take place at the front door?” Jimmy mumbled. “Shouldn’t we use our real front door?”
“No, Jimmy. My bedroom door will substitute as the front door in this roleplay. Come on, Jimmy; what takes place at the girl’s front door is a classic date move.”
Kate paused, and Jimmy had a big grin on his face. Suddenly, she wasn’t sure about being in a romantic situation with her little brother. “Forget what I just said about a classic date move, Jimmy,” she amended and blushed.
Jimmy knew what she’d almost said. It sent a fresh blush over his cheeks, but he didn’t back down. “Alright, then.” He pulled her chair around to help her get out. “Lead the way to your front door. And, um, how did I do at dinner?”
She appeared to be giving it serious thought as she strolled, trying to milk the hallway for as long as a driveway.
“Pretty good so far, Jimmy. Your conversation was balanced, and you refrained from staring at my tits. However, you could have touched me more, though.”
“Wait, what? Touched you?” Jimmy’s eyes dipped.
Kate rolled hers and said, “Not those, silly. I mean light stuff, and you could’ve held my hand or touched my shoulder or arm.”
She demonstrated, fingers running along Jimmy’s sleeve.
“Oh, right. Or maybe, like, your hair?” While they lingered by her bedroom door, Jimmy ran his fingers along that free, blue-dyed lock.
Kate’s breath caught in her throat. That touch was so affectionate that she felt the moisture wet her panties. “Yeah, that’s good.”
“But…” Jimmy hesitated. “What if Samatha doesn’t want me touching her like that?”
Jimmy was right. Kate wasn’t just training him to satisfy her tastes; she was getting him ready for Samatha, some other girl who would probably steal him away. She took deep breaths to calm and control the jealous fury which was suddenly in her chest. Kate gave him a sweet smile.
“That’s why you keep it light. If you touch Samatha’s arm and she doesn’t like it, read the signals and stop. But be gentle, and any girl should like it.”
Any girl. Jimmy knew that meant her, too. Both his hands fidgeted in front of him as they stood by her bedroom door. He could feel himself getting an erection and tried to hide it from Kate.
“So, how do I say goodbye at the end of a date?”
Yes, Kate thought. There was still one more thing she needed to teach Jimmy before their date ended.
“You don’t say goodbye; you say goodnight,” Kate said nervously, “And if you’ve shown your date a good time, it might go something like this.”
Kate froze, and they both stood awkwardly at her bedroom door. It’s okay. Kate tells herself as she rises on her tiptoes, puckers her lips forward while reminding herself it’s roleplaying and it’s just a kiss.
Except it wasn’t even that. Jimmy wasn’t of what she was doing, so he didn’t close the distance. He just stood there, staring, wide-eyed. At that moment, Kate realized she’d have to teach her little brother about not leaving a girl hanging.
Jimmy eventually caught on and pressed his lips to hers. It was clumsy, his lower lip on her chin more than her mouth, and it was too soft and hesitant. And it was almost far too awkward.
Kate almost called a halt to the roleplay then and there. But… It’s okay, she thought to herself. It’s just a proper goodnight kiss this time. But it wasn’t a good kiss, and she couldn’t let Jimmy believe it was.
“Not like that, Jimmy. You kiss your date like you mean it and want it. More like this.” Kate took a deep breath and sealed her mouth over his, tight and greedy.
At first, Jimmy just stood dumbfounded, not participating in the kiss. Then he joined in, his eagerness making up for his clumsy inexperience. His cock became rock hard, and he tried to keep her from feeling it. Eagerness? Was he just kissing her like she’d told him to, or did he really want her?
But Kate did feel his hardness against her. When the kiss broke, Kate’s head was spinning with possibilities. They still had much more of the date left, and it filled her mind so strongly that she didn’t even think to make justifications. She just opened the door behind her and exclaimed, “And if you’re really lucky little brother, she’ll invite you in.”
Jimmy was in shock, but he followed her into the room. With the door closed behind them, Kate gave her brother more kissing practice. Plenty more. She wasn’t sure whether she’d got his first kiss, period, but she absolutely got his first French kiss in a breathless tangle of tongues.
Kate’s body grew hot, feeling Jimmy’s hard cock against her, hearing his soft and boyish whines of pleasure. Too hot to be comfortable with clothing. She threw caution to the wind. First, she let her hair down, blond and blue curls tumbling to her chest. Next went her sexy black dress. Even once she’d unzipped it, it fits so tightly that it took some peeling and wriggling to get it off. Then she found she was uncomfortable with his clothing, too, and worked open his shirt’s buttons.
That got Jimmy’s attention. He pulled away from her kiss and wanted to ask what she was doing, but was speechless when he saw her hair down, and she was in only her lacy, black underwear.
“Wow.” That was all he said.
Kate quickly reverted to an experienced college woman. A lust-filled woman who knew what she wanted and needed. She smiled at Jimmy, tension humming through her skin.
“Much better, little brother. And that’s how you should react to your date dressed up all ‘flattering’.'”
“Uh-huh,” Jimmy grunted, his mind still blank. He moved willingly, letting her draw his shirt off and reveal his muscular, young torso. Jimmy had trouble with his balance, his gaze stuck on her body, and this was the first time he had seen his older sister in her underwear.
Kate’s little brother was looking at her in her underwear, and a corner of her mind whispered guilt. She shouldn’t be doing this. But it felt so gratifying to see the awe on Jimmy’s face and know that whatever happened with Samatha, these moments belonged to her and her little brother. There were still so many firsts she hadn’t taken, anyway.
It’s okay, she told herself. Jimmy will need to practice, and it does take practice. She took his hands and guided his arms around her, to her back where her bra clasped.
“Push the ends of my bra strap together,” she whispered to him. “Get the hooks out of the clasps, and it’ll come off.”
The promise of her bra coming off made Jimmy eager. Too eager, and it took a full minute of fumbling before she felt the release of tightness. She stood still as it slid off her pert, womanly breasts and revealed rosy nipples, already tight with excitement.
For a long moment, Jimmy couldn’t even say ‘wow.’ His first time seeing naked breasts in the flesh overwhelmed him. They may have been his sister’s breasts, but Kate knew how nice they were, and she’d been proud of them for years.
“Can…” When he finally spoke, his voice was inaudible and he had to swallow before he tried again. “Can I touch them?”
It’s okay, Kate told herself while she retook his hands. I don’t want him to be rough and grabby, do I? I must teach him how. She pushed his hands onto her breasts.
“Be gentle, Jimmy. But not too gentle.”
She needn’t have worried. Jimmy was delicate with her, squeezing and probing at the flesh that so easily overfilled his hands.
“Soft,” he murmured. “They feel so… so soft.”
And his smooth, gentle hands felt good to Kate. Even down to her panties, she still felt too hot for clothing. Her hands slowly left him and slid down to that last garment. When she caught herself hesitating, she told herself, It’s okay. You’ve seen each other naked before. Though back then, he still had been a baby. He was still half-dressed, and the front of his slacks looked uncomfortably full and tight. Kate stared into his eyes as she unbuckled his belt. The weight of the items in his pockets caused his trousers to fall to the floor, leaving him in only his boxer shorts.
Now, she had a teenage boy grow short of breath as he looked at her. His hands still on her breasts, he looked down between her thighs, gaze tracing over her smooth-shaven, flushed folds. He didn’t say a word, though she could see he wanted to. It’s okay, she thought, and her brother does need to learn about foreplay.
She parted her thighs, inviting him. “Touch it, Jimmy, but gently; it feels good to your date and helps her warm up.”
Not that she thought she could warm up much more without catching fire. Her brother explored her folds with one careful finger. Even that soft touch made her gasp. She took his hand and led him to her bed. Getting Jimmy to lie down with her didn’t take much coaching. Kate’s head tipped back against her pillow. As his finger eased inside her, she had to bite her lip to keep herself quiet. Mom and Dad wouldn’t understand that it was just practice.
But it wasn’t just practice. Kate was teaching her brother. His touch already felt good, but she knew how to improve it. She touched his wrist and said, “Turn your hand over. Palm up. And c-curve your finger like you are beckoning me to come to you.”
The second Jimmy did as she asked, the lucky bastard hit her G-spot. A squeal burst from her mouth before she could stifle it. He stopped instantly, panicked. “Are you alright?”
“Yes. Don’t stop, Jimmy.”
She was surprised by the tone of yearning, of need in her voice. But it was still just a lesson, just teaching her brother how to please women, she told herself.
“You can put another finger in, too. I can take it. And don’t forget my breasts.”
Kate worried that maybe he wasn’t quite ready for multitasking, but the reminder was all he needed. Both hands moved in concert: one stirring two fingers inside her while the other massaged her breasts. His eyes barely lifted from her body, watching what he was doing, and he moaned with a growing desire for his sister.
It’s okay; she told herself as her hands went to his boxer shorts. He just needs some help getting comfortable. Her hands moved like she was in a trance as she pushed his boxer shorts down and off.
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