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"Good on you," Marcus said as he slapped Robert's shoulder in encouragement. "Well, how should we set the rules? The one with the lowest hand takes off one piece of clothing. Anyone out of clothing is out, the last one remaining is the winner. Does that sound right?"
Jenny announced, "A bit unfair for me, I'm wearing a dress. I'll win anyway."
Marcus went off to fetch the cards, leaving Robert to steel his nerves. He had always secretly wanted to open up more, to be more than a serious, introverted nerd. This is a good chance; besides, he wasn't going to do anything too crazy, he thought to himself.
Before long, the four of them were sitting in a circle and the cards were being drawn. The first few rounds proceeded rather evenly; all of them lost their socks. Marcus was the first who was forced to show any significant skin. The girls cheered on as he casually took off his shirt, revealing his muscular torso. There was a trail of hair below his navel, leading below his pants. Robert could not help admiring Marcus's well-developed pectorals and six-pack abs. He felt woefully inadequate in comparison.
Lara lost the next round and chose to remove her bottom, giving the others a view of her white cotton panties. Robert's turn inevitably came though, and he swallowed as he moved to remove his shirt. He felt even more nervous as Jenny urged him on, "Let's see what you've been hiding there!" He felt more comfortable though once his shirt came off and nothing dramatic happened.
"You have a nice body, Robert. Don't you think so too, Lara?" Jenny commented.
"Yeah, he's pretty cute," Lara followed up.
Robert did feel warmed by those compliments, regardless of whether it was sincere or said just to make him feel good. For a while, he could even avoid comparing his scrawny body, his flat chest and smooth stomach to the athlete beside him.
"Ah, fuck!" Jenny exclaimed as she lost the next round.
"Well, here goes," as she stood up, lowered her hands and began pulling her dress up over her head. First to come into view were her red panties, then her belly and navel, and then Robert looked on in shock as he saw her exposed breasts. They were medium-sized, and each topped with a dark brown nipple.
"Yeah, I didn't feel the need to wear a bra underneath this dress. I am so disadvantaged here. Of course, I'd have been out anyway. Well, you guys carry on," she said, seeming completely unaffected by her toplessness. Robert did his best to stop himself from staring, but he could not help his frequent glances at the first breasts he was seeing in the flesh. Everything about them was arousing to him, their shape and firmness, the sight of her areolas, the color of her nipples. And most arousing of all was the fact that they belonged to the girl he so admired. He wished to compliment her but the words stuck in his throat.
Marcus, though, was openly ogling Jenny, leading her to remark, "Haven't you seen them before, pervert?"
Lara was the first to propose continuing the game. "That's the three of us left, should we deal the cards again? Come to think of it, this game will end up being rather short, Jenny's already out and I'm just one step away."
Marcus chimed in, "We do have more clothes to wager if you like. How about we remove this underwear rule? Then Jenny could come back in."
"I'd be more than happy with that. It's not fair that I'm the only naked one here," said Jenny.
"How about you, though, Robert? Are you comfortable with this? I know it wasn't part of the initial rules." She added, "Don't let us peer pressure you into anything that you don't want."
Robert hesitated. No one had seen him ever naked except his parents and doctors and the idea of exposing himself in front of three others, including his crush, terrified him. Yet, this fear was also coupled with sheer excitement at the prospect. Maybe it would be fun to be naked with others of his age and doing such a daring act might even boost his confidence for the future. And the sight of Jenny's breasts had inflamed him with a desire to see her completely in the buff. She was only one pair of panties away from that. He stammered out, "Yeah, let's go ahead."
Lara lost the next round, and a small tinge of red entered her pale cheeks as her blouse came off, exposing her small cleavage and smooth stomach to the others. Robert had ardently hoped that Jenny would lose a round as soon as possible yet it was the two boys who lost the next two. Firstly, Marcus removed his shorts to reveal his briefs, a large bulge straining against them. Then, Robert unbuckled his belt and let his jeans fall to the floor. He hoped against hope that no one would be able to notice his erection that was clearly visible through his boxers.
Now three of them were only one piece of clothing away from full nudity. Robert prayed silently that he wouldn't be the first. After the cards were drawn and exchanged, he found himself with two pairs, of 10s and 5s. That should be good enough, he reassured himself.
"Well, it's the moment of destiny," Marcus announced. "Lara, why don't you show us what you've got?"
Lara laid down three Queens. Jenny, in turn, grinned as she revealed her full house. It all came down to the two boys and Robert's heart thumped as he laid down his cards. His hopes were dashed though as Marcus slowly placed his cards on the table, with the words, "Sorry, man." He also had two pairs but of Kings and 8s.
Robert's head was spinning and he felt almost as if he was having an out-of-body experience. Like he was looking on from outside as the trembling boy stood up with all eyes on him. It was a stranger who put his fingers underneath his boxers, fumbling with them before finally sliding them down his legs.
Only when he felt the cool air on his privates did he remember himself. He looked down and saw his penis out in the open, stretching to its full extent, at a little more than 5 inches long. Robert had always been unsatisfied with its size and his shame was compounded by its public exposure. He hurriedly cupped his hands over his crotch, wishing that he would be swallowed by the ground. Why had he convinced himself that this would be anything but a terrible idea? What possessed him to think that others wanted to see his puny member? How would he ever look Jenny in the eye again? He stood there awkwardly, doing his best to conceal himself, his boxers still wrapped halfway down his legs. He expected to hear scornful laughter at any moment.
His hands could not cover everything and anyone who wished to could still see Robert's pubes, his balls, the tip of his cock. Jenny closed her eyes though with the others following suit. She said gently, "Robert, it's cool if you're not comfortable with this. You can dress up again and we won't look until that's done. I only caught a glimpse anyway."
Marcus followed up, "Yeah, this is just a silly game. You don't have to do anything that you don't want to."
These words had a soothing effect and after taking a few moments to calm himself, he decided that his reaction might be even more embarrassing than his initial exposure. Besides, everyone had already seen his nakedness and he would never be able to take that back. With the words, "No, it's alright," Robert slowly removed his hands, leaving his penis in the open once more. His heart skipped a beat when he noticed Jenny clearly looking straight at it before she raised her head and smiled at him. He sat down again, though he shuffled for a pose that might limit his exposure, but without too much success.
"Shall we continue then?" Jenny asked, deciding that it was best to move on from that episode and not put extra attention on Robert. Cards were dealt with the three remaining players. Lara was next to have to strip, she laughed as Jenny reached behind her to unclasp her bra. Lara's breasts were small but perky, with little pink nipples. "Nice ones," Marcus commented, drawing a small blush and smile in response.
Next, it was Marcus's turn to remove his last piece of clothing and he grumbled as he stood up, "Damn it, the only game I win at is basketball." Casually as anything, he took off his briefs, showing his penis to the room.
Lara gasped as she saw it, "That's the biggest one I've ever seen!" Marcus indeed had an impressive specimen, being 7.5 inches long and having a good thickness to supplement it. His pubic hairs were neatly trimmed short, accentuating his length even further. Marcus sat down with his legs slightly spread, seeming completely comfortable and confident in his nakedness.
"And why shouldn't he?" Robert thought. He admired the look of Marcus's huge cock and he could not help comparing it to his own, looking mournfully down at his groin. He had always considered himself to have a small penis and having Marcus's as a contrast seemed to drive that point home.
As if hearing his thoughts, Jenny said reassuringly, "Don't worry, Robert. You have a lovely cock as well."
Marcus added, "Yeah, we're just different, that's all."
"Well, it looks like it's just us two girls left then," Lara piped up, bringing their attention back to the game. Robert found himself ardently wishing that Lara would win. Would the winner even strip completely, he thought? That would somehow defeat the purpose of victory, wouldn't it?
When the round was over, Lara scowled as he laid down a pair of 3s. Jenny grinned as she revealed her own pair of 10s with a flourish. "Well, I said I'd win. I think I survived about 50 rounds in a row there," she declared. "Now off with it," she said turning to Lara. "Do you need my help again?" Lara made a token show of protest before she let Jenny slide down her panties.
Though disappointed that it was the wrong girl, Robert was aroused by his first real-life view of a pussy. Lara had a small, elegant slit between her legs, with her pink pussy lips being slightly visible. Her pubes had been trimmed into a triangle above her slit, and both boys were entranced as they saw that they were the same color as her red hair.
Jenny remarked, "Alright, guys, don't let your eyes pop out. I knew you'd love that! Doesn't she just have the prettiest pussy? And her fire-crotch! You won't see that very often."
"Well, they haven't seen yours yet," Lara responded.
"Trying to get me to strip too, are we? I did win fair and square. I have no problem saying you look better than me down there. To tell the truth, I'm actually a little embarrassed."
"Come on, Jenny, you know you want to. I know you want everyone in the world to see you and Robert here hasn't yet."
"You make me sound so promiscuous." However, she continued with a smile, "You got me, I do want to get naked. If only so nobody complains about unfairness."
Robert's blood raced as he processed these words and he realized that his fantasies were coming to fruition. So many times, he had undressed Jenny in his mind and felt guilty about it. Now, here she was willing to expose herself completely right in front of him. He watched, enraptured, as Jenny stood up, allowing Lara to return the favor and slide down her panties
Jenny's pussy was somewhat obscured by her rather wild, unkempt bush. However, as she spread her legs to step out from her panties, Robert managed to catch a glimpse of her pussy lips. He forgot his sense of propriety and continued staring at Jenny as she sat down, trying for a more thorough view.
"You've really let yourself go," commented Marcus, referring to her bush.
"Yeah, I've been too lazy to work on it lately. Looks awful, I know," Jenny replied, without having an actual hint of embarrassment.
Lara contributed, "Well, it looks like not everyone agrees. Robert's just been staring at it the whole time."
Robert blushed as he was found out. Jenny caught his gaze and smiled enticingly at him.
"Like what you see, Robert? At least someone appreciates me." Saying that, she used both hands to spread her pussy apart. Robert nearly choked as he had a direct view of Jenny's light red lips and opening.
All too soon, though, the moment was over as Jenny moved her hands away. "God, I don't know what came over me. I'm not usually that open," she said with a laugh. "Well then, what should we do now?"
The few seconds of silence that followed were abruptly ended by Lara. "I'm really horny," she declared.
"Well, aren't you always? Anyway, that's not a suggestion," Jenny responded.
"Hey, you're just dripping," Lara fired back, as her fingers went through Jenny's bush and into her pussy. "Well, I'm just saying, there are two of us girls here, and two boys."
"Well, that's me busted," Jenny giggled. "And of course, the boys are obviously excited too," she laughed again, pointing at the two erect cocks. "It'd be nice to tire ourselves out before bed."
Marcus entered the conversation, "Hang on, are we really doing this? I'm in, of course. How should this work, though? The four of us split into pairs?"
Lara continued, "I was thinking more about taking turns with each other."
"Looks like Lara's here not content with just one cock," Jenny commented. She turned towards Robert, still with the same enticing smile she wore earlier, "Robert, are you in as well? Not to pressure you or anything but it would be so nice if you joined us."
Robert could barely believe what he was hearing. Since he had first become interested in sex, he had reconciled himself to remaining a virgin for the foreseeable future. Sex, to him, was something that happened to other people. And now he was facing the immediate possibility of having sex with the girl of his dreams. He could never have imagined as he woke up this morning that the day would end this way. His body was crying out for him to agree, his mind hesitated. He had no moral issue with such activities, but did he really want to have his first experience in such a manner, in a small crowd with zero privacy? Was that really the intimacy he craved? The sight of Jenny's sweet smile and her delectable body, however, inflamed his lust and overpowered his other considerations. He found himself slowly nodding.
"That's great! Let's get started then," Jenny announced excitedly. She caught herself for a moment, "Of course, any one of us can stop at any time. I remember when I was fucking Ben, it was only my second time. He was halfway in me when I just felt so scared all of a sudden and asked him to stop. He was so upset," she laughed, "but that didn't matter. Pardon my rambling everyone, should we get down to it?"
Marcus said, "We're taking turns with each other, right? How long should they take? Should we say a minute?"
"Yeah, that sounds right. Could we hurry up? I can't wait anymore," Lara said excitedly while shuffling towards Marcus.
Jenny fished out her phone from her dress on the floor. "Let's make out to start. Well, I'm starting the timer then."
Robert gulped as Jenny walked towards him, her whole body on display. He couldn't think straight as Jenny sat down close to him. Out of the corner of his eye, he could already see Marcus and Lara going at it, their mouths open as they hungrily locked lips. In front of him, he could see Jenny's face approaching his before stopping midway, waiting for him to make his move. She looked more beautiful than he had ever seen her, she was smiling softly while looking deep into her eyes. Instinctively, Robert began moving his head towards hers, stammering as he asked, "Jenny, may I kiss you?" He could hear giggling from the others as Marcus and Lara interrupted themselves to watch them. Jenny's eyes seemed to be shining as she responded, "Of course you may," and then closed her eyes to invite him forward. Finally, Robert closed the distance and tenderly placed his lips on hers.
This contact lasted only a second but it felt like an eternity to Robert. He was overwhelmed by the fact that he was really kissing Jenny, that they were both stark naked, that they were doing this in front of an audience. Robert smiled widely as Jenny opened her eyes and smiled back. "You have such a beautiful smile, Robert, you should do that more often." The sound of the timer, however, interrupted this dreamlike state.
"That was too short. Well, I guess it's time to swap," Jenny said as she restarted the timer before scooting over to Marcus. Her place was taken by Lara, who showed no hesitation in taking the initiative and planting her lips on Robert's. As he experienced his second kiss in quick succession, Robert felt conflicted about kissing somebody else. He did find himself enjoying the feel of her lips, which were even softer than Jenny's. Robert kept his eyes open, and directly in front of him, he appreciated Lara's pretty face, her glasses still covering her eyes. He also could not resist glancing across, where Marcus was French-kissing his crush. He felt a tinge of jealousy though his rational side managed to suppress this. It would be silly to feel entitled to her, especially as he himself was currently kissing another girl. He continued with the closed-mouth kisses, feeling a little embarrassed by his lack of skill.
Again, the buzzer sounded and the two girls backed off, huddling together again. "Well, that was fun! What's next?" Lara asked.
Jenny's response was swift. "These two cocks have just been begging for attention the whole time. Do you think we should help them along? Or maybe we should do nothing and see if they'll cum on their own."
Robert self-consciously noticed that the tip of his cock was already wet with his pre-cum and indeed felt as if he could ejaculate at any moment without any more stimulation. He also felt an overpowering urge to jack off. Glancing to his side, he again looked on at Marcus's large erection, wondering if he felt the same way.
Jenny laughed as she restarted the timer and started crawling towards Robert, giving him a good view of her luscious back and butt. Robert again felt as if he was in a dream. Surely Jenny wasn't about to actually touch his cock? For a moment, he wondered if this was an elaborate prank, could the three of them have planned this? Maybe they were setting him up only for Jenny to withdraw at the last moment, and then they would laugh at him for thinking that he was worthy. But then, he knew Jenny and Marcus, and surely, they wouldn't be capable of that? These thoughts raced through his mind as Jenny wrapped her hands around his shaft, and Robert exulted in the feeling of being touched there for the first time.
His doubts only fully evaporated though, as Jenny flashed him a dazzling smile, saying, "I've been looking forward to this," before taking almost his entire length in her mouth in one go. The feeling was incredible, Robert's cock had never experienced such warmth, such moisture. More than the physical sensations, and amid his other feelings, he felt such joy at the intimacy. "Jenny's actually giving me a blowjob," he thought. He closed his eyes and thought he might be dreaming, but no, when he opened them, there she still was with his cock in her mouth. He let out a moan as Jenny sucked her way up his shaft, pausing for a moment to lick the underside of his cock. So engrossed was he with Jenny's attentions that he barely even noticed the audible sounds of Marcus's own moans as Lara fellated him.
Jenny went on to run her tongue all over Robert's shaft while cupping his balls. Then, she was at it again, opening her lips wide to envelop his penis. It was at this moment, that Robert lost control. He was feeling such pleasure that he could hardly think. With a cry, he unloaded spurt after spurt into Jenny's mouth. She remained in place, taking his entire load before withdrawing.
After recovering from his orgasm, Robert looked down at Jenny's pretty face and felt mortified. How could he have done this to her? "Sorry, sorry," he hurriedly said. "I should have warned you."
