A Chance Encounter (remake)

They both looked at him with expectant eyes, which made him blush as well. "Well, don't push yourself, but... it is pretty hot."

The girls looked at each other again, nervously inched a little closer, hesitated, then closed the gap and kissed each other. After holding that timid kiss for a while, they both cautiously wrapped their arms around each other, smushing their breasts together. Their lips parted and they brought forth their tongues, caressing each other in a slow, sensual embrace. Chance, Megan, and Sophia watched on in tense silence as the two of them went at it. Eventually, they broke the kiss and withdrew from each other, both smiling bashfully.

"I guess that was... kinda nice." Sayako affectionately swiped a lock of red hair from Shelley's cheek and tucked it behind her ear.

"Somehow this feels weirder than everything else we've done tonight. But... yeah." Shelley idly ran her hand across Sayako's breast, giving her stiff nipple a gentle tug.

As if suddenly remembering their audience, they both let go of each other and turned back to Chance. "Right, um, what were we doing again?" Sayako chuckled.

"I think it's time to take their virginities, right Chance?" Megan cooed.

"Yeah. I'm more than ready." His cock had felt so drained before, but now it throbbed without any hesitation. "If you girls are still up for it."

"Oh, I'm not gonna back out now." Shelley rose to her feet to reveal that her snug white panties had a big damp stain on the crotch. Sayako quickly followed, revealing the same of her own black ones. They both hooked their thumbs into the waistbands and pulled them down in tandem, revealing two pale pussies with thick, glistening outer lips. Shelley's pubes were curly red, Sayako's silky black. "I don't know if I can handle riding you though," Shelley continued, squirming her thighs. "So you can go on top."

Sayako looked at the mattresses on the floor. "Maybe we can lie down side-by-side, so you can take turns? Would you like that?"

Chance had been expecting the difficult question of who would go first, but this was far better. "Yes, that's perfect." Megan and Sophia released their two-sided embrace of him, so he rose to his feet to stand before the two virgin girls. Of course, he still didn't have any confidence in taking charge. "Um, on your backs, I guess?"

"Can I make a suggestion?" Megan cooed. She lowered herself onto the mattresses and stretched out on her front, smushing her breasts beneath her body. Lying prone, she lifted her hips off the mattress a little and swayed her ass left and right. "How about this? Perfect for fitting side-by-side."

Shelley and Sayako looked down at Megan, then expectantly up at him. "Oh, um, yeah, that seems great," he said, thankful that he wasn't alone in this daunting task.

"Okay," Sayako said with a nervous smile as they both lay down. They looked at Megan and mimicked her position, arching their backs to raise up their butts. Once they were in place, Megan rolled over and sat up. Sophia sat down on the other side, ready to spectate.

"How does it look?" Shelley said over her shoulder.

Chance nervously eyed the full, firm asses of the two girls, so appealingly presented side-by-side. His cock throbbed hard as his mind raced with all the things he might do wrong. "Looks amazing. Um... Saya was first to suck me off. So Shelley will be first this time. Okay?" There wasn't much logic to that, but he had to choose someone, and he'd rather not interrupt the tension by making them play rock-paper-scissors.

"Yes, please," Shelley said with a grin.

"Sure, I'll just watch." Sayako smoothed out her hair over her shoulder to get a better view. "I guess I'll know what to expect."

He got down on his knees and straddled Shelley's legs, his cock looming over her lovely ass. He wanted to ride her so badly, but he had never performed the act of insertion himself. On top of that, her pussy lay hidden between her full cheeks and thick thighs, showing only a partial glimpse at her shiny pink folds.

Apparently, Megan sensed his hesitation, because she crawled up closer and took a hold of his cock. "I'll help you out," she purred against his ear. She slid the head of his cock between Shelley's thighs, where it touched upon the unmistakable wet heat of her pussy. Then she slowly moved it around for a moment, stroking it against her slick folds, until he felt his tip dipping into her snug entrance. "Now thrust."

"Thanks, Meg," he sighed as he slowly moved his hips forward and felt his cock sliding smoothly into Shelley's body. Megan retracted her hand, so he pushed even further, until his lap was pressed down against Shelley's ass. He couldn't see himself penetrating her, which made it strangely more intimate, but he could feel his cock throbbing against the snug grip of her pussy.

Shelley swayed her hips left and right, grinding her firm ass against his lap and his cock against her slick walls. "Feels nice," she cooed softly.

Relieved by the easy insertion, Chance shifted his position, planting his hands next to Shelley's shoulders. It felt weird, being in control like this. Weird but good. "Tell me if I go too hard, okay?" He started a slow thrusting motion, stroking his cock in and out of her just two inches at a time. "Or if I do anything that doesn't feel good."

"I will," she moaned softly as she arched her back a bit more, lining up her pussy with his cock just right.

Chance felt certain that if things had been different, if this was the way he was losing his virginity, he would embarrass himself by climaxing about now. Thankfully, the desensitization from two orgasms was still helping him out immensely. Still, he felt an instinctive urge to speed up, to pound Shelley hard and fast until he emptied his balls into her womb. But he couldn't do that. He had two girls to satisfy, so he had to take it slow.

He focused on doing long, deep thrusts, that way he was less tempted to go fast. He pulled back as far as he could without risk of slipping out, then pushed all the way in, pressing his lap firmly against her ass. When he did, he could feel the tip of his cock kissing the fleshy barrier of her womb. "You feel great, Shelley," he sighed, wanting the inexperienced girl to feel validated.

"So do you," she purred, lovingly smiling back at him over her shoulder.

As much as he would love to keep going, they had agreed to take turns. He would have to do short rounds, as Megan and Sophia had done earlier, so he could hopefully keep them both warmed up. A daunting task, but he didn't want to keep either of them waiting for long. "Alright, time to swap." He carefully pulled his cock out of her, then let it rest on the firm cushion of her ass while he looked at the other girl.

Sayako had spread her legs a little, snaked her arm beneath her body, and was stroking her pussy with two fingers. "Oh, is it my turn?" she perked up excitedly.

"It sure is." He unstraddled Shelley and took up the same position on top of Sayako, who withdrew her hand from her crotch and eagerly raised her butt for him.

"I'll help you put it in," Sophia cooed as she shuffled closer. She grabbed his cock, gave it a few loving strokes, then guided it right up against Sayako's pussy.

"Thanks," he moaned softly, feeling in disbelief at how well they took care of him. He took a deep breath, then carefully thrust into Sayako's body. She was a little tighter than the others, but just as sopping wet, so he smoothly slid all the way inside. "Feels good?" he asked before proceeding. She nibbled on her bottom lip and quietly nodded her head, while shifting her position to better align her ass with his lap.

He resumed the same slow, deep thrusts that he had started with Shelley. Sayako's butt was softer than Shelley's, which made the ebb and flow of his thrusts feel a little different, though equally wonderful. Knowing that he had switched from one pussy to another made the whole experience more electric, made his cock feel more sensitive as it ground against the slick inner walls. This was the fourth woman he'd had sex with, which was a baffling thing to consider given that number had been sitting at a solid zero until today. He tried not to dwell on that, or else he'd surely get too carried away to focus.

"You feel great too, Saya," he moaned, punctuating his words with a deep, lingering thrust that ground his sensitive head against her cervix. He wanted to be gentle with her, but the urge to ride her harder and faster was building up.

She responded with a muffled moan of her own. "You can go harder if you want," she purred, almost as if she could read his mind.

He hesitated in his thrusts. "Are you sure?"

"Uh-huh. I'll warn you if it's too much." She showed a naughty red-cheeked smile that made his cock throb inside of her.

"Okay..." He slowly pulled back, then thrust inside forcefully, creating a soft wet slap against her ass. She let out a soft gasp but didn't complain, so he repeated the motion, starting a steady rhythm of forceful thrusts that made her full, soft ass wobble with the impact.

Chance found himself letting out a series of soft moans as well, to mingle with Sayako's as their bodies slapped together again and again. This felt almost obscene, for him to be in control of such a gorgeous girl, taking her for his own pleasure. Surely, a regular guy like him didn't deserve to be in this position. Yet here he was, loving every second of it.

He could have continued fucking Sayako for as long as his cock would let him, but he wouldn't let himself get carried away. He looked over at Shelley, who was pleasuring herself with her fingers while watching the two of them intently. Clearly, she was overdue for her turn.

He gave Sayako one last forceful thrust, then carefully withdrew from her. "I'll be back soon." He dismounted her and clambered back on top of Shelley. Without missing a beat, Megan grabbed his cock and lined it up against Shelley's pussy, letting him slide all the way inside of her with a single smooth thrust. He sighed in satisfaction as the wet heat engulfed him again. Perhaps he could have done the insertion himself at this point, but this was undoubtedly more fun.

He steadied himself in preparation, firmly planting his hands and knees. "I'm gonna ride you like I did with Saya, okay?"

"Yes, please," she cooed, nibbling her bottom lip in excitement.

He eased into it with a few slow thrusts, but then resumed the same quickened pace, slapping his lap against her ass while plunging his cock deep into her sopping wet pussy. Her toned ass was firmer than Sayako's, didn't wobble as much with the impact, but the wet slapping sound it made was no less satisfying.

While he was focused on pacing himself, Megan crawled up in front of him on all fours. "Hey, stud. Think you can multitask?" Before he could process her question, she pulled in close and pressed her lips against his.

His thrusting motion faltered as she captured his attention, but then he reasserted himself, resuming the steady rhythm. He parted his lips for her and their tongues met in the middle, engaging in a passionate kiss. This double-sided stimulation was suddenly a lot harder, now that he was the one doing the work, but he loved it all the same. Thankfully, Megan seemed unbothered by his tongue being clumsier than usual, and readily took control, guiding him into a sensual dance.

They went at it like that for a while. He felt almost in a trance as he enjoyed Megan's mouth and Shelley's pussy side-by-side, accompanied by the sound of Shelley's soft moans. It was a miracle that he was able to sustain this, that he still didn't feel his orgasm approaching. Admittedly, under normal circumstances, he probably wouldn't even be sustaining an erection right now, so shortly after two powerful orgasms. These girls were running him ragged and he was loving it.

He no longer had a good sense of how much time had passed, but he decided on a whim that he should switch again. It took a bit of willpower to stop, but he pulled away from Megan's lips, then out of Shelley's pussy.

"Don't make me wait long, okay?" Shelley purred lovingly, reaching between her thighs to caress herself in his absence.

"I'll do my best." He gave her butt a playful squeeze and dismounted her.

As soon as he crawled on top of Sayako, Sophia once again guided his cock to its rightful place. As soon as he was balls-deep inside, Sophia embraced and kissed him, pushing her huge breasts against his chest and her tongue into his mouth. He moaned against her lips, caught off-guard by her enthusiasm. He couldn't take up his normal position like this, but he didn't want to push her away either, so he improvised.

He wrapped one arm around Sophia's waist, holding her close as he accepted the deep tongue-filled kiss. His other hand, he placed on Sayako's hip, giving him some leverage as he started thrusting his hips in short, fast motions. It was an awkward angle at first, but Sayako adjusted her position to accommodate him, and soon his cock was smoothly plunging it and out of her sopping wet pussy.

"Feels good," she cooed softly between strained moans.

He couldn't answer her, but he moaned affirmatively against Sophia's mouth while lovingly squeezing Sayako's hip and speeding up his thrusts some more, frantically humping against her ass. As they fucked like that for some time, it was all starting to catch up with him. The caressing embrace of two pussies, the loving kisses of two women, not to mention Sophia's curvy body grinding against him... the tension in his balls was finally starting to rise.

It took a considerable amount of willpower to deny his imminent release, but he had to do it. After a final flick of the tongue, he gently pushed Sophia away, then withdrew his cock from Sayako's body, which left it throbbing forcefully against the air. "It's... Shelley's turn again," he said, breathing heavily as he dismounted from Sayako and straddled the redhead.

With Megan's help, he swiftly plunged back inside of Shelley, which made her purr in delight and squirm beneath him. Megan then embraced him for a kiss as well, just as Sophia had done. He accepted the kiss for a few seconds, but then gently pushed her away. "Meg, I do love... this..." he said bashfully, gesturing at the entire situation. "But I need to focus on Shelley's pleasure or I'm going to bust. Okay?"

Megan blinked for a moment, but then smiled affectionately. "Oh, yeah, of course. We are pushing you kinda hard, aren't we? I'll just sit back and watch you fuck Shelley's brains out." She gave him one more quick kiss, then sat down on the mattress and crossed her legs, looking at him with a playful little smile.

He swallowed as he realized the high expectations he had taken on. Suppressing his doubts, he planted his hands next to Shelley's shoulders and resumed his thrusting motion. A few long, slow thrusts at first, to make sure he was no longer overstimulated. When he found it safe, he sped up, once again filling the air with the wet slapping sound of his lap hitting her ass. "Let me know what feels best, okay?" he panted while looking at her pretty green eyes, or rather the one eye he could see. "Faster, slower, whatever you want."

"You got it," she purred, pushing some red curls from her face so she could better look back at him. "Feels good so far."

He nodded at her with a nervous smile as he dutifully continued riding her. Although the pace of his thrusts was quick and forceful, he did his best to maintain a steady rhythm. That took some focus, preventing him from getting carried away. He felt sure that he wouldn't last very long if he allowed himself to devolve into mindless, frantic thrusting. All the while, he ran his eyes all over her, admiring her beautiful body. Her round ass, her slender back, the way her breasts bulged out to the sides as they smushed against the mattress.

"Hey, Chance," she moaned softly, her breathing now heavy and strained. "Could you, maybe... get closer?"

He didn't quite understand what she meant at first, but when it clicked, he eagerly obeyed. Slowing his thrusts, he lowered his body on top of her, planting his elbows on the mattress so he could bring his head close to hers. From this position, he had to make shorter thrusts that ground his lap against the cushion of her ass. It didn't produce the satisfying slapping sound, but he loved the feeling of her soft body pressed against his. Seeing the opportunity, he snaked his hands beneath her body and cupped her breasts, gently squeezing the soft flesh and feeling her stiff nipples grind against his palms. "How about this?" he whispered against her ear.

"Perfect" she purred, turning her head to rub her cheek against his. "Maybe... a little harder?"

He repositioned his knees for better traction, then redoubled his effort, riding her even more vigorously. Shelley responded with a series of strained moans, while arching her back and squirming her thighs. He was pleasantly surprised how well he could feel her bodily reactions now... and how well she was responding in general. "Are you close?" he moaned softly against her ear.

"I think so..." she whimpered. "Just... keep going..."

That was music to his ears, because as much as he would like to, he didn't have a lot of time to keep trying. He felt the tension in his balls looming, threatening the approach of his third orgasm, the one he probably wouldn't recover from. "Okay," he whispered as he squeezed her breasts more firmly and focused all his will on maintaining the same steady pace. It felt increasingly unmanageable, but the thought of what would happen if he climaxed now, if he left her disappointed right on the brink, that gave him the strength to keep trying.

Thankfully, the miracle he was hoping for happened just in time. Shelley gasped as her body tensed up and her back arched even more. Suddenly, her pussy was clenching and pulsing around his shaft, just as it had done for Sophia and Megan. He thrust all the way inside once more, then held it there, letting her orgasm wash over him. It was tempting to keep thrusting, to make it as intense as possible for her, but he felt sure that he would climax along with her if he did. It was hard enough to resist already, the way her quivering pussy massaged his cock, as if begging for his seed.

Eventually, the throbbing of her pussy ebbed away and Shelley took a deep breath. "I think you did it," she chuckled, playfully grinding her ass left and right against his crotch. "That felt really good, Chance."

"I only barely made it." He leaned in to kiss her cheek. "But you're welcome." He paused a bit longer, to make sure that a sudden movement wouldn't make him climax, with how sensitive his cock had become. Then he carefully pulled it out and sat up.

As it turned out, he had become quite blind to his surroundings while in the thick of things, because he only realized now that Sayako had changed position. She lay on her back with her legs spread, while Sophia sat next to her, stroking Sayako's pussy in slow circles with two fingers. Sayako had one hand on her own face, as if hiding in embarrassment, and the other placed on Sophia's breast, gently squeezing the soft flesh as she squirmed and moaned softly.

Sophia saw him looking and showed him a naughty smile. "Chance, I kept her warm for you," she cooed. "I think she's quite close to busting. Wanna finish her off with your cock?"

He throbbed so hard at that invitation that it was almost painful. "Oh, wow, thank you. I really need the help." He shuffled closer and loomed over Sayako's supine body. She looked up at him, red-faced, nibbling on her bottom lip in anticipation. Hesitation made him look back up at Sophia. "Can you still finish her off if I fail?"

She chuckled a little. "Probably. But I think she'd really prefer to cum on your cock. Don't you, Saya?" The other girl nodded her head assertively. Sophia showed a teasing smile. "Go get her, soldier. I have faith in you." She gave him a quick kiss, then withdrew her hand from Sayako's crotch.