Testing Boundaries

“Would you like some water or something?”

Jacob looked up from where he was sitting on her brother’s bed, idly scanning the titles on a shelf of manga. Hazel put on her best smile, trying to look friendly. “It’s probably going to be a little while before my brother gets back,” she offered as an explanation.

Jacob shrugged. “Sure, why not.”

Hazel turned towards the kitchen to fetch a glass. Her heart pounded a little. It was always a treat when her older brother’s best friend came around; he was handsome, charismatic, and always had this... aura around him. A gravity. Hazel had definitely spent more time than she should watching him out of the corner of her eye whenever he was over. Her father wouldn't like it; she knew that much. If he knew what she was thinking... but whatever. He wasn't here right now. Jacob was.

She put some ice cubes in a glass and hurriedly filled it before heading back to her brother’s room and slipping inside. She shut the door behind her; Jacob had left it open, but it had a tendency to bang against the wall in the wind when it wasn’t secured.

Hazel handed Jacob the glass, lingering idly so that she could keep looking at him as long as possible. He was tall and broad—an athletic build; he was on the high school’s football team—with short dirty-blond hair that looked like it would be soft to the touch. He looked like the lead out of a teen rom-com, or maybe off the cover of a magazine somewhere. Hazel’s heart fluttered as he took the glass from her hand, his fingers brushing over hers in the process.

Taking the glass into his own hand, Jacob took a big gulp, his throat convulsing around the swallow, and set the glass on the windowsill behind the bed. He grinned at her, his mouth pulling up in his familiar crooked half-smile. “That uniform looks good on you,” he commented. “Very cute.”

“Oh this?” Hazel said, blushing. She was still in her school uniform; she hadn’t yet changed out after getting home. She held the fabric of the skirt out to the side with one hand. “Yeah, Dad insists that I stay in the Catholic school,” she said, rolling her eyes. “It’s so lame. Toby gets to go to public school with you, but I’m still stuck with the nuns.”

In truth, she knew that the uniform looked good on her. She’d put off asking for a larger one even though she’d had a recent growth spurt, because she liked the way the white button-up shirt stretched tight across her generous breasts and the skirt was starting to be just a little too short, showing a tantalizing amount of thigh. Feeling bold, she took a chance and sat down next to Jacob on the bed, wanting to prolong the conversation. “My Dad’s such a hard-ass,” she said, confiding. “He has all these super strict rules for me because I’m his ‘precious little flower’ or whatever.” She stuck out her tongue.

Jacob smirked. “Not a fan?”

Hazel smiled at him. She kind of wanted to bat her eyelashes, but she was worried it would come across as weird and cartoonish. She didn’t have much practice flirting. “Well, you know,” she said, trying to make her voice softer and lower, “I would much rather just go to school with you and Toby. It would be nice to get to see you every day, even if it was only in the halls or whatever.”

Practice or no, it seemed like she was getting the idea across; Jacob’s gaze sharpened on her quite suddenly, as though he was evaluating her in a completely different light. Another lazy, crooked grin stretched its way across his face. “Is that so,” he murmured. “I bet there’s all kinds of things they won’t let you do in Catholic school.”

“Totally,” Hazel agreed. She swallowed. “Hey, have you seen what my brother looked like in his old uniform? He was pretty cute too...” She shifted on the bed, bringing up her legs under her so she could prop herself up on her knees and lean over the bookshelf that butted up against the footboard. It had a lot of knick-knacks on it, including an old photograph of her and Toby together at St. Maria’s. She arched her back to do so, knowing that it would put her bottom pointing directly at Jacob, giving him an eyeful.

She hadn’t even manage to grasp the photo when she felt Jacob’s body lay itself over hers like a blanket, the heavy weight of his torso covering her back and his hips nesting against hers. She gasped as he pulled her backwards with a gentle pressure, sitting back down on the bed and tugging her into his lap, front-to-back. As he did so his arms came up around her, one encircling her stomach and the other her upper chest. She gasped again as his hand casually came to rest on her breast and then squeezed.

“I see how it is,” he murmured into her ear, making her shiver. “Feeling a little repressed with all those Catholic rules, huh?” His hand began to knead her breast rhythmically, while the other idly stroked up and down her hip and upper thigh. His face nuzzled into the crook of her neck; she could feel the barest light brush of stubble against the soft skin.

Hazel said nothing, unsure what to do. She hadn’t expected this to go so far so quickly. But the hands on her felt good, and his body was warm and solid behind her. She was surprised to find herself turned on by his bold forwardness. She bit her lip and decided not to respond, waiting to see what he would do next.

With no protest stopping them, his hands continued to roam her body. The top one began to slowly, methodically undo the buttons of her uniform shirt—one, two, three—until it was open enough to slip his hand inside and into her bra. She groaned as his fingers sought out her nipple and began to play with it, pinching the nub and rubbing it between them. Meanwhile his other hand rubbed up and down her thigh, up and down, until it slowly began to pull up her skirt and creep beneath it. Hazel pressed back against him involuntarily.

“Feels good?” he breathed into her ear with a chuckle. “I thought you were showing off for me. Heh. Always wandering by when me and your bro are studying, wearing that cute little skirt. You were hoping I’d do this to you, huh?”

His hand crept further up her thigh, up and up to the joint of her hip until it was brushing over her underwear. Then it shifted further between her legs, until his cupped hand was pressed over her cloth-covered crotch. She felt his lips curving on her neck as he simultaneously squeezed her breast and applied pressure to her nethers, kneading them both. She gasped as pleasure rocketed through her, throwing her head back against his shoulder.

“Atta girl,” Jacob murmured. He continued his ministrations idly, apparently in no hurry, his hands groping her possessively above and below, for several minutes. Hazel felt a stirring twitch in his lap underneath her. She blushed, realizing she was making him hard. She felt a strange thrill of triumph that her body was able to arouse him in this way.

“You’re gonna have to change your underwear after this,” Jacob teased. “You’ve totally soaked these ones through. In fact...” he paused to lick a stripe up her neck from the shoulder to the corner of her jaw. “Why don’t we get those off for you?”

“Oh, I don’t- Wait-” Hazel tried to protest, but Jacob was already shifting her weight so he could pull them down, lifting her torso with one hand and yanking the fabric down her thighs with the other. He didn’t bother to pull them all the way off, leaving them twisted half-way down her thighs instead. This was further than Hazel had planned to go; a little over-the-clothing groping was one thing, but actually getting naked...

Her eyes widened as he set her back down. Apparently in the process of maneuvering her weight, he’d also unzipped his fly. She could feel the soft, smooth flesh of his erection under her bare legs. This was definitely more than she’d bargained for.

He was rocking back and forth underneath her, his hard cock frotting against the bottom of her thighs. She heard him groan low in his throat. “That’s more like it. Now, sit up a little bit so I can get an angle to get into you.” He started to pick her up again, positioning her.

“No!” Hazel protested hurriedly. “No, wait! Please don’t! Stop! You can’t go in!”

Jacob hesitated for a moment, and then started to pull her back down against him. For a second she thought he was ignoring her protests, but instead he positioned himself so that his cock pierced up through her thighs, lodging between them and sliding along the slick flesh. The pressure of his member was tight against her pussy and clit, and she groaned involuntarily as he began to thrust between her thighs, sliding his cock up and down. Her skirt blocked her view, but she knew that if it hadn’t, she would have been able to look down and see the head of his dick peeking up at her between her legs.

“Why the hell not?” Jacob growled as he continued to slide himself through the trail of her copious wetness. “You some kind of tease? Gonna get a guy all worked up and then not put out like a prude?”

Hazel gulped. “It’s not that I don’t want to-” although she kind of didn’t. “It’s just that...” she blushed. Her father’s voice rang in her ears, his endless lectures on how precious her virginity was, the importance of saving herself and her purity. “I’m a virgin,” she admitted. “I’m supposed to protect my precious flower.” She bit her lip. Jacob’s thrusts continued, rocking her steadily back and forth on top of him. Both his hands rose to her chest, cupping one of her breasts in each hand and squeezing. She gasped. “My father would absolutely kill me.”

Jacob’s face was back at her neck, licking at it again as his words vibrated against her skin. “Who cares?” he muttered. “How the hell is he gonna find out?”

“He checks every night.”

Jacob’s movements suddenly stilled, coming to rest with his body still wrapped around her like a blanket. “He does what?”

“He checks,” Hazel repeated, unsure what the problem was. “He’s a doctor. Every night he examines me down there to make sure I’m still a virgin.”

There was a long pause before Jacob said, “That’s fucked up.”

“No it’s not,” Hazel insisted. She thought about their nightly routine. It was almost comforting at this point, the way her father would come into the room, closing the door behind him, and wait for her to spread her legs beneath her nightgown. He would kneel beside the bed, and she would feel his confident, methodical finger enter her and slowly inspect her insides, verifying her purity. When he was done he would smile at her and pat her head, congratulating her on maintaining her virtue. Sometimes, if she had been wet enough for the inspection that he hadn’t required lube, he would then present his finger in front of her for her to lick off, popping it into her mouth. She was well accustomed by this point to swallowing the taste of herself from her father’s digit. He always seemed so proud of her when she did.

Jacob snorted. “If you say so,” he muttered. He resumed his thrusts between her thighs. Hazel sighed in relief. At least he seemed willing to go along with her boundaries. This much she could handle. It was a little... intense, but she could handle it, and this way she wouldn’t be accused of teasing him. She relaxed into his touch.

“So then,” Jacob said against her neck, “all that matters is that we do something your daddy won’t be able to notice, right?”

Without any further warning, Hazel was thrown forward on the bed, onto her hands and knees. Disoriented and off-balance, she barely had time to get her bearings before she felt Jacob behind her, hands on her buttocks, pulling them apart, and the light pressure of his cock head against the pucker of her asshole.

“Wait, n-” she started to protest, but it was too late. Jacob’s cock was already parting her, pushing its way into her ass, well-slicked from her own juices. She let out a strangled groan as she was breached. He forced himself into her mercilessly, without pause, sinking in slowly millimeter by millimeter. She felt a choking sensation in the back of her throat as she was filled inexorably by the spear of his organ.

“See?” Jacob said cheerfully as he finally bottomed out inside her ass, his balls coming to rest against her weeping vagina. “This way you keep your precious purity. Daddy never has to know.” So saying, he began to thrust into her.

If being filled had been a tortuous splitting sensation, the motion was even worse. It was all Hazel could do to hold on as Jacob fucked her ass with confident, deep thrusts. He paid her little attention, except to lean forward enough to put a hand on the back of her head and hold her down. His cock plundered her, taking all the pleasure he desired and leaving none behind. Hazel wanted to protest, but she couldn’t find the breath for it; she was seeing stars.

Jacob continued to pound her, filling her over and over like he was punishing her for something. Her rear hole was stretched wide, wider than she’d even realized it could be, until she felt like she was going to break in half. Behind her, Jacob was laughing. “I knew you had it in you, slut,” he said approvingly. “Does that feel good, huh? Taking a cock up the ass?”

All Hazel could do was groan. Jacob’s thrusts sped up, ramming into her with such force that he had to put both hands on her shoulders to keep her from sliding forward on the bed. His cock was a jack-hammer, splitting her apart. She worried she was going to pass out.

Then, finally, he stilled, She felt his balls twitch as he filled her rear passage with his cum. He seemed to come for ages, holding them both steadily in position with his cock buried inside her as deep as it would go, emptying himself. Wave after wave of heat bloomed in her as his balls loaded her up with sperm.

Finally, after far too long, he slipped out and fell back, sitting down on the bed. “Fuck yeah,” he wheezed. “Now that’s the stuff. Damn. Let me know next time you want me to plow you like that again. Happy to help.”

Hazel could say nothing, lying collapsed on the bed and trying to get her breath back. After a moment, she heard Jacob say, “Oh, shit!”

Suddenly his hands were on her again. Hazel had little idea what was happening as he yanked her back up into a sitting position, hurriedly pulling up her panties and smoothing her skirt down over them.

A few seconds later, just after Jacob had pulled his hands back, Hazel realized what was going on. The doorknob turned and it began to swing open, revealing her brother Toby standing in the room’s entrance, looking surprised to see her there.

“Hey Haze,” he said curiously. “You okay? You look a little flushed?”

“U-h-hmmm?” Hazel managed. She ran a hand self-consciously over her messy hair.

“Hazel was keeping me company while we waited for you,” Jacob said casually. He showed absolutely no indication of their previous activity, somehow astonishingly still neat and put-together despite the wild abandon with which he’d been slamming himself into Hazel’s ass only moments before. He grinned over at her. “But she was just leaving, anyway.”

“O-oh,” said Hazel, still in a daze. “Yeah. Right.” She cleared her throat. “I was.”

She stood, trying to hide the shakiness in her legs. As she did so, she felt a trickle of Jacob’s cum begin to leak out of her ass and down into her underwear. She looked down so her brother wouldn’t see her blushing. “E-excuse me!” she managed before shoving past him into the hallway.

She went immediately to the bathroom to shuck off her clothes and step into the shower. Turning her back to the spray, she bent over and slid two fingers up her own ass, opening it up to let the water cleanse her. Clenching her jaw, she set to work cleaning away any trace of evidence out of her well-ravished hole.

After all, it wouldn’t do to let her father discover a man’s cum inside her when he came to inspect her later that night. She had her purity to maintain.