More First Times

Author's note: This story is a sequel to 'First Time Strip Poker'. Feel free to read this story without reading the first instalment, but it will make a lot more sense if you do. The full order of stories published with these characters can be found on my profile.

My thanks go out to Jim1855 for proofreading this story and making invaluable corrections and suggestions. Any mistakes that do remain are, of course, my own. Enjoy!

***

"Would you make love to me?"

Lin was looking at David with a nervous expectation, still lying on her side, clearly fully aware of the impact of such a question. David was not surprised that this was the favour she wanted to ask him. She had mentioned over the course of the night that she had had fantasies about him taking her virginity, and apparently had even thought about asking him whether he would be willing to. The erotically charged circumstances of the night, paired with the copious amounts of alcohol, must have finally given her the courage to take the plunge.

David hesitated. There were plenty of reasons to do it. First of all, Lin was an attractive girl. No point in denying that, especially now he had already seen her naked. Furthermore, he felt flattered that she had asked him. Who wouldn't be flattered when a pretty girl asked you to take her virginity?

Aside from the flattery, chivalry also played a part in the appeal of her proposal. She was unable to have a normal dating life, due to her meddling cousin and parents, so he was about the only choice she had. It made sense that she asked him, he was the only one of her male friends who was single.

On the other hand, she was a good friend of his, so things might get awkward after, especially as this was her first time. She might develop romantic feelings for him as a result of the shared intimacy, but because of her home situation, a relationship didn't seem feasible to David, even if he would develop romantic feelings for her, which at the moment he thought unlikely. So they would have to be able to deal with the fall-out of the event.

Then again, it had worked out well enough when he and Stephanie had slept together, all those years ago. There was no reason it should be problematic if they were clear on the terms of the night. He just needed to be sure she wouldn't regret this.

"Are you sure?" he asked her, looking straight in her eyes. "It's a pretty big step, wouldn't you rather wait until you met someone special?"

"David, not this again!" she exclaimed, "We've been over this before, with the kiss. I appreciate your concern, but I want to know what it's like to have sex. I'm twenty-one years old and have literally zero experience. Even more, I have no possibility in the foreseeable future to change that. Apart from tonight, the one night Mei has allowed me to leave the house. It feels like it's now or never, and I want it to be now. You're one of my best friends, I trust you. Show me what it's like. That's all I need from you."

"No regrets after?" he asked her.

"No regrets after," she reassured him, "Just this one experience, to round off the evening."

David smiled, convinced by her certainty. "Very well then, my lady. You shall have it."

He moved in, and gently put his lips on hers. She responded immediately, kissing him back hungrily, opening her lips open as an invitation for his tongue, which sensually darted towards her lips, touching them, and then retreating again. Lin wouldn't have any of this teasing, though, and opened her mouth further, sending her tongue out to chase his. She kissed him hard, with a longing passion, as though they were two lovers who were reunited after a long time apart.

Without breaking the kiss, David rolled Lin gently on her back and straddled her. His hands clamped firmly on either side of her face, he slowly withdrew from the kiss and looked deep into her eyes. They were confident, ready for whatever he was about to do.

David needed no further encouragement, and promptly kissed her again. Before she could respond, he had moved on from her lips, planting soft kisses on her cheeks, progressing towards her ear. He started nibbling on her earlobe, letting his tongue explore all the ridges, licking, biting, teasing. She moaned softly, indicating her satisfaction with his actions.

"You know," he said, "I've always thought you had very pretty ears."

"Idiot," she responded, chuckling, but then she sighed in pleasure again. "I never knew ears could be this sensitive."

David merely chuckled in response, before moving away from her ear, kissing her cheeks again, then her lips once more. This time he did stay long enough for Lin to respond, and they were making out again, as passionately as the first time they had done so, only a few hours before.

Before long, David started to move downwards, first kissing her neck, and then gradually moving lower. One by one, he opened the buttons on her pyjama top, exposing the bare skin underneath, and immediately smothering her chest with soft kisses. First he kissed her right between her breasts, which were still covered by the fabric, but soon he moved on to her midriff, kissing sensually and eventually, after opening the last button, he playfully stuck his tongue inside her navel.

"Let's get you out of this", he said, slowly opening her pyjama shirt completely, exposing her naked chest. Lin wordlessly sat up and shrugged off her top, before quickly lying down again, ready to enjoy David's sensual touch.

"I meant all of it," David said, and tugged on her pyjama bottoms. She raised her hips, so he could slide them off, revealing to him, for the second time that night, her neatly trimmed pubic hair and her soft pussy. She looked very vulnerable, naked and unsure of what to do, as if she was hoping she was still doing all right.

He had sat up taking off her clothes, though, and in this position, his erection could not be hidden by his own pyjama shorts. When Lin noticed what effect she was having on him, she seemed to relax a little.

"Apparently I'm not the only one enjoying this," she said teasingly.

"Why would you think otherwise? I have a beautiful naked woman in my bed, and she's mine to do with as I please," David responded, "Who would not be enjoying this?"

With these words, he took off his pyjamas too, and lay down next to her on the bed, slowly rolling her on her side and spooning her.

"I can feel your dick against my butt," she giggled.

He kissed her neck in response.

"Get used to that, missy. I doubt you'll ever lie in bed like this with a guy who hasn't got a huge boner."

He started caressing her body, first down her sides, slowly moving up and down, from her shoulders along her waist towards her ass, then over her thighs, all the way to her calves, and back up again. She shivered in pleasure as he passed over her waist. After a few minutes, he moved his free hands towards her breast, kneading them softly, playing with her nipple, occasionally kissing her neck.

"Don't forget the other one," she said, turning ever so slightly towards him so he could have better access. He moved over to the other breast, giving it the same attention he had given to the first, before letting his hand once again wander below, stroking her stomach. His hand moved lower, and immediately she opened her legs, tilting her hips slightly so he could reach her pussy.

She moaned as he slowly caressed it, turning her body towards him, giving him better access. She had turned over completely now, lying on her back, her breasts heaving as she moaned with pleasure. This was the sign for David to start his work in earnest, caressing her labia, and softly rubbing her clitoris, first slowly, and then gradually faster.

Lin responded well to his touch, moaning softly at first, but as his movements sped up, so did her breathing, and there was no doubt that she was approaching orgasm soon. She was not quiet about it either, moaning louder and louder, like she had done when he had eaten her out earlier that evening. David guessed that Stephanie and Michael, who slept in the adjacent room, could probably hear her, but they were past such embarrassment now, anyway. He kept his pace steady, slightly increasing the pressure on her clitoris every once in a while, as Lin completely gave herself over to her pleasure, bucking her hips against his hand to increase the pressure whenever she needed it.

"Ah... yeah, ... ungh... just like ... mmm.... that... don't stop... aah... now", she managed to say, in between increasingly breathless moans.

David continued obediently, softly pushing his body into the side of hers, his erect penis pressing hard into her thigh. Instinctively, she grabbed hold of it, and squeezed it hard as she finally came. She was arching her back, head tilted backwards, her hard nipples pointing at the ceiling. David slowed his movements to a halt as the bucking of her hips ground to a stop. Lin just lay there, panting, one closed fist grabbing a handful of the sheets, the other still firmly around David's dick.

"You're incredibly sexy when you come," he whispered softly, "just watching your naked body, your pleasure,... it makes me incredibly horny. All I want to do now, is keep that going."

With that, he tenderly pried her hand away from his member, and repositioned himself with his head between her legs, ready to pleasure her orally once more. He had just planted a kiss on the inside of her thigh when he felt her hand on the top of his head.

"You don't have to do that," she said, still slightly out of breath, "you've made me come twice tonight already, I couldn't ask for more."

"I want to," David answered, looking up, past her moist pussy, over her flat stomach, in between the mounds of her small breasts, topped by those delectable dark nipples, into her eyes, still half closed in pleasure. "I enjoy your pleasure as much as you do. And even better: the more turned on you are, the smoother it will go later." He kissed her thigh again, this time closer to her pussy.

He gave her clitoris a small kiss, softly and tenderly, and the slight moan this elicited told him everything he needed to know. With her hand still resting on his head, David went to work, first licking the outside of her labia, moving his tongue up and down, and gradually moving towards the centre. Then, he finally reached her clitoris, his touches provoking another series of moans.

"How does this...mmh... feel even better than ... the first -- oh - time?" she managed to gasp between moans.

"I just keep getting better," David answered with a grin, before going down on her once more.

"No, seriously, this feels way better than before."

"It's probably because there aren't any people watching this time. It's just you and me. Relax, and enjoy the ride."

With that, David resumed his licking. Lin immediately responded to his gentle, exploring tongue, her head turning one way and the other in pleasure, her petite breasts rising and falling with every moan that escaped her mouth. He was tasting her tangy juices before long, and had a sudden flashback to earlier that evening, when he had been eating her out as well.

The idea that he had given her her first real orgasm -- masturbation aside -- turned him on more than he would have thought possible. Even though he had already come earlier that night, thanks to that amazing blowjob from Ashley, his dick was rock hard and aching for attention. David slowly inserted a finger in Lin's pussy, which was dripping wet. She moaned even louder as he moved his finger in and out of her vagina, her second orgasm coming ever closer.

"Oh god, that feels amazing," she moaned, "Do another one."

He added a second finger, and it sent her over the edge. She emitted a guttural moan, and at the same time clamped her legs around David's head. As the orgasm washed over her, her pussy became even wetter than before, and he could feel her vagina contracting around his fingers. She seemed to keep coming forever, her back arched and her head snapped back, while her thighs still kept David in a headlock.

When finally she relaxed her legs again, David wasted no time. She was wet, she was relaxed, she wanted it: she would never be more ready to have sex for the first time than at that very moment. He slithered out of bed while she was recovering to find the emergency condom he always had in his bag, and quickly put it on.

"Are you ready?" he asked her, as he leaned over her.

"More then I'll ever be," she answered.

He kissed her softly on the lips.

"Just remember," he said, "Whenever you want to stop, we'll stop. Just say the word."

"Thanks," she replied. "For all of this. I couldn't have imagined it any better."

"Hey, that's what friends are for," he said.

He guided his penis towards her waiting opening, and inserted it slowly. He gasped as the warm tightness of her pussy enveloped him. She was so wet he slid right in for about two inches, before the narrowness of her hymen stopped him. David's instincts screamed at him to push himself all the way inside her, and only with a lot of restraint he managed to stop himself from forcing his dick violently into Lin's narrow pussy.

Instead, he pulled back slightly and started to move the tip of his penis in and out of her. She sighed deeply, and grabbed his waist with both her hands, guiding his movements.

"That's nice," Lin whispered hoarsely, "I always thought it would hurt".

"I'm not nearly all the way in yet," David responded, "This is just the tip. I want to go step by step."

"Go on," she said, "I want to feel all of you."

David started to push slightly harder. He could feel his penis force its way through, her tight avenue reluctantly opening as he slowly thrust into her. Lin's face was screwed up now, no longer relaxed and overcome by pleasure but in discomfort, pain even. She was whimpering softly. David ignored all his instincts, and stopped his movement immediately, holding still once more, partly inside of her.

"Does it hurt?"

"Yes," she groaned.

"Want to stop?"

"No, keep going, it'll pass. Just be slow and careful."

David resumed his movement, pushing deeper inch by inch, halting each time to give her body time to adjust to his girth. Every time he continued, a small whimper of pain escaped Lin's mouth, but she didn't say anything. When he was completely inside her, he stopped once more, and kept still.

"I can't go any deeper. Does it still hurt?"

"Yes, but not so much anymore. How does it feel for you?"

David smiled. "You're really tight, but that's normal for your first time. Your body has to adjust to something new. Do you want me to start moving again?"

She nodded, and he pulled out of her in one smooth movement, almost completely. He could see her relaxing a bit as he pulled away, and bracing herself again as he made to enter her again. It went smoother this time, but Lin was clearly still in pain. By the third time he entered her, however, she had opened up most of the way, and she sighed as he slid in her, slowly but without hesitation, and then pulled out once more.

"The pain has gone," she whispered, smiling weakly.

David didn't respond, but continued his movements, in and out of her. She felt amazing, the perfect mix between tightness and smoothness, and he was glad that he had already come once that evening, as the stimulation of her tight vagina would probably have caused his orgasm too soon for her to get any enjoyment out of the experience.

He remembered the first time he had had sex. It had been with Julie, his first real girlfriend, and it had been her first time as well. She had been on the pill, so they hadn't used a condom, and even though he had tried to get her as ready as humanly possible, she had still screamed loudly as she had penetrated her. Even worse, he had come after only about five thrusts, completely overcome by the sensory overload it had been, just as the pain caused by his penetration was fading away. She had had her hopes up about her first time being magical, and sometimes he still felt bad for letting her down. Of course, they had sex more successfully after that, but you can't experience your first time twice.

He was determined not to have the same thing happen with Lin, and he paced himself, moving in and out of her slowly. Apparently, the pain had stopped pretty quickly, and now Lin was obviously getting some pleasure out of it, too. Her whimpering had been replaced by soft, high-pitched hums of satisfaction, every time he moved into her. She had her eyes closed, and her nose crinkled in enjoyment whenever he pushed deeper inside.

Before long, Lin started moving her hips to meet his thrusts. David looked down at her, from top to bottom, seeing her face screwed up in enjoyment, her mouth slightly open as she groaned in pleasure. Her small breasts were moving up and down as her breathing became harder, her hard, dark nipples inviting to be nibbled, if only he were able to reach them. Looking down, past her flat stomach, he could see his dick completely disappear into her moist pussy as her hips came up towards his, enabling him to get deeper inside of her.

A change seemed to have come over her. Now that the shock and the pain of her first penetration was over, she seemed to have lost all reservations and was going for it with her body as well as with her brain. She had grabbed hold of his hips even firmer, and was pulling him towards her, faster and faster, showing him the rhythm she needed him to follow.

As the tempo of their thrusts increased, so did the noise Lin was making. She was moaning louder now, and for a second David worried that Stephanie and Michael, who were sleeping in the next room, would hear her. These thoughts of caution were soon driven from his mind, however, when Lin suddenly tilted her pelvis and wrapped her legs around his waist. David would have been surprised by how supple she was, if he were not engrossed by the wonderful feeling this deeper penetration awarded him. He could feel his orgasm approaching with the new stimulation this angle afforded. Lin, too, was apparently reaping the benefits of her position change, as she was now screaming loudly every time he bottomed out.

"Oh, yes! Fuck me, David! Fuck me hard!"

She pulled his body towards her with a renewed energy, drawing him in over and over again. Lin's sexual awakening had brought out a new side in her, one David had never imagined existed. The passion and vigour with which she was slamming his body into hers, the volume of her pleasure, the twisting and heaving of her lithe body underneath him,... It was beyond his wildest expectations, so different from the timid way she usually acted.

He had imagined sex with Lin before, of course, but in none of his fantasies she had been this wild. She had always remained mostly passive and pretty, like a superior being who allowed him to do what he liked, but out of grace rather than out of her own desire. This Lin was completely different, she was more like a goddess unleashed, aware of what she wanted and doing whatever it took to get it.

He was approaching his zenith quickly now. The combination of the visual stimulation provided by Lin's writhing body, the sound of her screams of pleasure and the rapid movements of their lovemaking was quickly becoming too much for him to handle, and with an animalistic grunt, he came for the second time that night. He held himself still, buried deep inside of her as wave after wave of pleasure washed over him.

"Oh!" Lin exclaimed in surprise, "I can feel you come!"

David didn't reply, but collapsed on top of her, sweating from the exertion. She wrapped her arms around him and hugged him tightly.

"Thank you, David. I'm so glad we did this."

"No complaints here, either," David grinned, as he disentangled himself from the hug and slowly slid out of her, taking care to take the condom with him. He knotted it up and wrapped it in some tissue, before lying back down next to her.