Chapter 2

"Okay," he nodded. "If you don't like anything or want to stop, just tell me, okay? And I will, at any moment. Just tell me if something doesn't feel good." He looked serious and she believed he would do as he said. She hadn't known him for very long, but for some reason she felt safe with him.

He started kissing her again, this time gentler, less urgent. He slowly went from her lips to the side of her face, placing soft kisses along her jawline, to her ear. He put her earlobe in his mouth and sucked on it gently. She jerked at the electric sensation that shot through her. She enjoyed what he did, a lot.

"Is it good?" he whispered hotly in her ear, and it made her shudder again. Apparently her ears were really sensitive. He barely started and already found an erogenous zone. Score. He patted himself on the back mentally. He continued sucking on her earlobe gently, while his hands went to her back and found the clasp of her bra. "Is it okay if I take it off?" he asked, his palm firm and hot between her shoulder blades.

"Yes," she moaned huskily in response. Relieved by the fact that they didn't have to have sex, she relaxed against him and was willing to explore and get a taste of what it might be like without actually risking anything. His fingers snapped the bra open in one expert move and she wondered how many times he had done this before. But her brain became fuzzy again quickly when he went down to kiss and suck on her neck. That part of her anatomy proved to be just as sensitive as her ears, and she felt dizzy with desire. His lips felt so good on her skin, she could barely form a coherent thought at this point. She idly wondered how someone who can't move one half of his mouth could be so good at kissing and necking. Her bra now hanging loose underneath her shirt allowed him more freedom and he moved his hands to her front to cup her breasts. Her nipples perked up at the contact and she pushed into his palms creating more friction. Her natural instincts took over at this point and she was grinding at his erection with a steady rhythm. Jess pulled away from her neck to look at her face, and she was completely lost in sensation, her eyes closed, eyelashes fluttering, cheeks flushed. She opened her eyes to look back at him, and they were dark and dazed. He slipped his hands from underneath her shirt and she whined in protest. He placed his fingers on the top button of her PJ top and asked if it was okay to undo it. She nodded and he proceeded. Slowly he undid every button, one by one, keeping eye contact with her, his smoldering look hypnotizing her. She was so aroused, she was trembling in anticipation of what would come next. He opened her shirt and pulled the bra upwards to look at the chest, finally seeing what he just touched. The sight of her nipples, hard and ready for his mouth, made his dick twitch. She was so beautiful like this, turned on, with her breasts out. He couldn't wait any longer and lowered his head, capturing her right nipple between his lips, sucking it into his mouth. Her whole body went taught as the sharp pleasure pierced through her at his touch. She let out a soft whimper and clenched at his waist. He went on covering her entire chest from underside of her boobs to her collar bones with opened mouth kisses. She was moaning and whining in pleasure non-stop, the sounds urging him on, making him even harder if that was possible. He felt like he was reaching the point of no return at the pace they were going and the sounds she was making. If she didn't intend to go all the way tonight, he didn't know if he could stop if she asked. But he let the thought slide for now. He kept caressing her breasts and she grinded against him, building up the pressure. He really wanted more, oh so much more.

"I want to see you," he whispered, hot and wet against her ear.

"Wha..?" she didn't think she understood what he meant. Her brain was so foggy with lust she could barely see straight, let alone think.

"Can I take off your pants? I wanna see you," he kept sucking on her pulse point and she found it hard to find reasons why he shouldn't see her like that. But something in her mind told her she needed to be careful, the hesitation reflected on her face. Somehow he seemed to notice her apprehension.

"Rory, have you ever heard me bragging about any girls at all?" he asked her. She shook her head 'no' after considering it for a second. Come to think about it, he really didn't do it. It was Tristin who loved to flaunt his newest conquests to the entire school. She heard rumors in the girls' locker room that Jess had a big dick and was a magnificent lover. But it was unclear who started those rumors. Jess, of course, had been seen making out with different girls at parties over the years, but he never once boasted about them, so his escapades were kept pretty much private. Rory didn't know about any official girlfriends. If anything, girls liked to talk about sleeping with him themselves, like it was considered a prestigious thing to boost their popularity. He never confirmed or denied anything, and stayed surprisingly tight-lipped about his love life.

"I don't kiss and tell. Don't worry, what happens between us stays between us." That seemed to reassure her and she let him keep going. He laid her down on the couch in front of him and slowly slid his hand down her body until he reached her core. He pressed down onto her cupping her through her pants and asked "Is this okay? Do you want me to keep going?"

She hesitated for a moment, but then nodded and whispered "Yes, keep going."

He started rubbing her through the thin fabric, palming her pussy, feeling the pants getting wet at the spot where they connected to her entrance. She spread her legs wider for him, whimpering and moaning softly. Seeing her reaction he slid his hand underneath her pants and underwear and cupped her bare skin. She was already so wet he could barely keep his restraint. He continued playing with her pussy, gently stroking the slit, spreading her juices everywhere, rubbing her clit, making her moan and writhe. Finally he pulled on her pants and she lifted her hips from the couch letting him take the garment off. She was left in her panties with a cupcake print on them that matched her PJ's. When she put them on before going out, she thought they were cute. That was before she started this sexy activity with Jess. Now she thought they were stupid, her face flushed in embarrassment. He looked up at her with that sexy ass smirk, but didn't mock her fashion choices. He nuzzled her vagina instead, taking in the scent of her arousal, and it made his pulse race. He hooked his fingers underneath the fabric and slowly pulled her panties off. And there she was. Shy virginal Rory laid bare in front of him. He appreciated the importance of this sacred moment. She'd never done this before. Nobody had ever seen her pussy before. She didn't wax, but her pubic hair was neatly trimmed into a triangle. He found that endearing. Her lips were pink and swollen with desire, glistening with her juices, inner smaller lips opening up like petals of a blooming rose. She looked perfect. He groaned at the sight and dove right in, sliding his tongue inside. Her legs spread wider on their own volition and her back arched at the exquisite feeling of pleasure. He kept going, probing with his tongue, and she was so wet, dripping, so sweet, delicious, it turned him on in a way he'd never felt before. He just kept licking, he licked and licked, not able to get enough, until she started moaning louder, but still the sounds were cute and small, it was driving him insane. He wanted to make her moan his name. Somehow it seemed important at the moment, to hear that, to be that guy she moans for, longs for, the first one she desires.

He put one finger inside, slowly, carefully, but she was so wet, he slid in with ease. She clenched around him at the pleasant sensation and whimpered, finally moaning his name. "Jess…"

"Fuck, Rory, you taste so good," she flinched not expecting any words at all, especially not such dirty ones. His dick was so hard, he was afraid he might come then and there, so he needed to take a break, to catch his breath for a second. He pulled away, and she was able to finally see his erection. He was wearing sweatpants and loose boxers, so his cock was not restrained too much, and it was clearly visible how much he was aroused. He seemed big and she looked at him hesitantly. "Jess?"

"Just give me a second... fuck… Rory… you have no idea what you do to me," even though he thought it was just impossible not to have guessed by the looks of his penis.

She sat up and reached out for his hard-on shyly. He stopped her hand as she was just about to touch him."Rory…" he growled in warning.

"I… I wanna… see you too..." she stammered.

He groaned and his head fell back on the headrest. "Fuck Rory, you can't say things like that."

"Why not?" She wasn't sure what she did wrong. She was so painfully naïve and oblivious in her inexperience, it was torture for him.

"Because my self-control is not as strong as you think."

"Why?" she asked. This whole situation made her feel on edge, excited and nervous.

"Are you serious? You taste so sweet, and it makes me so fucking hard. Look how hard I am right now, if you touch me I might just fuck you right here on the spot. So if you're not ready for more, I would advise you against coming anywhere near my dick."

"Oh," she's taken aback, but at the same time she's seriously considering going for more. Was she ready though? Was he really going to fuck her like he said he would? The desire to see his cock was too intense.

"Can I… uhh... can I do something else to make you feel good, without the actual sex, that is," she asked.

"Fuck… Rory, you're killing me."

She looked at him with those big blue eyes that darkened with desire. She wanted them to keep going, doing… well… anything… being with him felt too good to stop.

He opened his eyes and looked at her again. She looked so sexy, sitting in front of him with her PJ shirt unbuttoned, her nipples out, hard and pink, her pants on the floor, her pussy so open in front of him, calling for him, inviting.

He wanted nothing more than to free his cock from his pants and dive right in. But was she ready for it? There was a yearning in her eyes telling him she wanted something more. He took a few deep breaths and took her hand in his and put it on his bulge.

She gulped audibly as she felt it under her palm, hard and twitching, and so big, oh god, so big. She was nervous and curious at the same time. She gently stroked him through his pants.

He tried really hard not to shoot his load right then and there. He wanted to continue licking her but wanted her to touch him too. It was a tough choice. She became bolder with every stroke and after a few moments, pulled down his pants gently. He was wearing boxers but she tugged on them too in a sudden bout of confidence. She freed his cock and gasped. She'd only ever seen an erection in a text book in her health class, but it was a drawing not a photo, so she didn't really know what to expect. She also read about the average sizes of male and female genitalia, but Jess's cock looked bigger than average. The sight somehow made her mouth water and her pussy clench in longing. She took him in her hand but didn't know what to do next. So she just kept her hand there completely still, feeling his dick throb. He covered her hand with his gently and showed her how to rub him properly. They kept going in a steady rhythm until he couldn't take it anymore. This whole situation was too hot for him to handle. He wanted to fuck her but knew he couldn't, so he stopped her instead, and made her lie down again.

"Spread your legs for me Rory," he said, and continued where he left off. Now that he was licking her again, she seemed even wetter than before, obviously aroused by the sight and feel of his dick in her hand. He sucked on her clit, making her howl. Suddenly, she was not so opposed to the idea of sex. He kept eating her out, her whimpers and whines getting louder, her pussy getting wetter by the second. She trembled as he put two fingers inside. She wondered what his cock would feel like. His fingers slide in so easily, with no restraint, as they were all coated with her juices.

"Fuck, Rory...you have no idea how much I wanna fuck you right now... So wet... You're so fucking wet... fuck!" he took his fingers out and sucked her juices off his hand. She saw it and whimpered at the sight, it looked so hot. She'd never been so aroused in her life. She reached out for him and took his fingers into her mouth, licking them clean. And he almost came seeing her lusty expression. She was surprised with her own taste, but not at all disgusted. When she sucked on his fingers he kept thinking it was his dick she was licking. When she was done he covered her mouth with a hard bruising kiss, letting her feel her taste in his mouth, showing her how much he wanted her. She pulled him closer on top of her and his tip bumped against her clit and they both moaned. At that moment she decided she wanted him.

"Jess?" She asked timidly. "Do you... Uhh… do you … have a condom?" she whispered in his ear.

"What? Why?" He was confused by the question.

"I wanna do this... with you… right now." He looked at her, her eyes wide, but she looked serious, determined even.

"Are you absolutely sure?"

"Yes…" She blushed hard.

He reached for his pocket and took out a foil wrapper. It was a last minute thought to put a condom into his sweatpants. He wasn't sure how this night would go, so some natural instinct urged him to be prepared, just in case. Who could've thought it would actually come in handy tonight.

"Last chance to say no... it's gonna hurt… Most likely…" He only ever slept with one other virgin before, so he didn't have a whole lot of experience like that. But he knew for a fact the first time for girls could be very far from pleasant, even if it happened in the loving relationships with long term boyfriends. And much less with some random guys at slumber parties. He felt responsible for her now. It was entirely up to him to make this experience as enjoyable for her as possible.

"I wanna do this, I want you," she was obviously scared, but for some reason the idea of walking out of this room without knowing what it's like to have him inside her pained her beyond belief.

He rolled the condom on and sat back, pulling her on top of him. "Maybe it will be better this way. You can stop any time you want, okay? If it hurts or you change your mind," he told her gently brushing her hair out of her face.

She nodded in agreement, but didn't move. "I... I don't know what to do…" She was blushing at her inexperience. But at the same time she felt safe with Jess. He didn't look like he was mocking her. His look was sincere and focused on her.

"It's fine, I'll guide you," he took her by the hips and gently moved her in position straddling him, so that her pussy was right above his dick. He took it in one hand and navigated her hips with the other, when his tip touched her entrance they both moaned. He helped her move her hips back and forth rubbing her slit and clit against the head of his dick, getting the arousal back, he wanted her juices flowing again.

They kept going like that until she was moaning out loud like before. She grabbed onto his shoulders for support and marveled at his strength. He was bumping his head continuously into her clit and she felt like she couldn't take it anymore, she wanted something inside, something bigger than his fingers, she wanted his dick. So she started to move more forcefully and the head of his cock slipped inside by accident. She froze but the feeling was pleasant and he helped her rotate her hips which stimulated her entrance. It felt so good; she wanted more so she slowly started to lower herself onto him more. He was so big, he was stretching her out forcefully and it felt a little weird. He was definitely bigger than his two fingers. She sank down some more until she reached a certain limit where it seemed to not go any further. She stopped there and looked at him questioningly.

"This is the part where it hurts," he said softly. "We can still stop, you know," he whispered, gently rubbing her bare back. Even though he felt like his dick might explode if they did. She gulped and shook her head in refusal. She wanted to do this. So she kept lowering herself but it wouldn't budge. Then she put more strength into it and just tried to sit down. A sharp pain shot through her. She stopped, crying out, a single tear stained her cheek. Jess looked at her pained face and rubbed circles on her hips trying to soothe her. She stilled on top of him, but didn't get off of him nonetheless. She was panting hard trying to calm herself. She knew it would be painful, but it hurt a lot more than she thought. She didn't play any sports or use tampons, so her barrier didn't get a chance to be stretched or ruined in different circumstances that would prepare her better for this experience. Him being bigger than average didn't help either. Meanwhile Jess felt like dying. She was so fucking tight and she was in pain, and he couldn't do anything about it. He tried to take deep breaths through his nose to ease the tension. Finally Rory felt like the pain subsided some, so she decided to try again and dropped down some more. He felt gigantic inside her, tearing her apart, but it didn't feel too horrible anymore. So she went all the way down until he was buried to the hilt. She stilled again trying to get used to the feeling of him inside, of being so full, stretched out. Her brows were furrowed in concentration, eyes closed. Jess was panting heavily… He'd only been with one virgin before and it was a long time ago. He didn't do virgins anymore. So this experience was somewhat new for him too. He desperately wanted her to carry on, to move, to do something.

"Rory…" His voice was strangled. He gripped her hips bruising her. She didn't protest, but that set her in motion again, so she rotated her hips, grinding on him. He moaned out loud. Then she tried to lift herself up and his dick slid almost all the way out of her, leaving just the tip inside. That felt really good and Rory kept going like that, all the way down and then almost all the way up increasing the speed. But it got too intense for Jess. He felt like he was a virgin himself again, the tightness of her pussy almost unbearable. He tried with everything he got to hold off until the end, to prolong this for her. He would've preferred short thrusts while buried deep inside, rather than his whole length being rubbed continuously. This always made him cum a lot faster. But apparently it felt better for girls and Rory naturally chose this course of action because it eased the pain away, bringing pleasure instead. But she was on top, so he couldn't really control what she wanted to do, plus it was her first time. It was about her, and if she wanted to do it like that, it was her right.

"Rory... Fuck... Rory... " He was so close, he was about to come, but she was nowhere near there yet. It was her first time, and he didn't want to shoot too early, but he couldn't help it. She was so tight and he had been secretly dreaming about fucking her for so long. He put his hand on her neck to get her attention. "Rory… I'm so close, too close..." She looked up at him. She wasn't in pain anymore, and she wanted to carry on with the same motions. His length felt incredible sliding all the way in and then almost all the way out.

"What...are you saying?" Her breathing was labored. She looked at him in confusion.

"I'm saying I'm about to come... but you're not…"

"Oh..."

"Please Rory, let me come, you're so fucking tight, so wet, it's so hard to hold out… fuck... I'll make it up to you I promise..." His words turned into moans.

"Okay…" She was intrigued and aroused by the sounds he was making. With a low guttural moan he stilled underneath her as he came. His hands gripped her hips tightly preventing her from moving. She stared at the look of pure rapture on his face and marveled at the fact she made him feel this way. He looked magnificent. She wanted to see more of him like that.

When he was done he carefully pulled out and took the condom off disposing it in the nearest garbage bin. The maid would be surprised in the morning, no doubt. After all, the library would be the last place at this house that sex usually occurred. Rory was disappointed it was finished so early, she would have loved to continue, but then he came back to the couch and pushed her gently on her back and spread her legs again lying in between them. Without giving her a chance to prepare, he attacked her slit with a ferocious kiss and kept on licking and sucking on her clit, inserting two fingers and moving them in and out, until she exploded in her first ever orgasm on his tongue with a loud moan. He sat back looking down at her, her whole body flushed with the prettiest shade of pink, eyes closed, chest heaving, nipples hard. He was mad at himself for not being able to hold on for longer and shooting off like a thirteen year old. He didn't expect it to feel this good. But at least he managed to make her climax anyway. Her breathing slowly evened out and she opened her eyes. He had a soft look on his face she didn't see in school, and she smiled at him, and he smiled back with his perfect crooked smile. She sat up and leaned in to kiss him on the lips. Her movements were gentle and his heart clenched at this tenderness he felt towards her and at the vulnerability she allowed him to see. When she pulled back he murmured softly against her lips.

"Do you wanna go to sleep?"

"I think so, yeah." She nodded. He stood up to retrieve her pants from the floor and she blushed again, suddenly realizing she was half naked while he was still fully dressed. She put her pajamas back on awkwardly and buttoned her top. He tugged the blanket from under her and then took her hand in his pulling her to stand up. Then he went to lie down on the narrow couch and patted the place right next to him inviting her to lie down. She climbed the couch and he grabbed her in his arms making her lie almost completely on top of him and then covered them both in a blanket. She sighed in content and stretched to kiss him on the lips.

"Good night," she smiled at him, her face happy.

"Night," he smirked at her playfully and hugged her closer. She rested her head on his chest and soon was lulled to sleep by his steady heartbeat.

To be continued…