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Night Before The Concert

The night before a concert, some of the girls decide to thank their friend's older brother
It all started with free concert tickets. Josh's sister and a friend of hers had managed to win four tickets and found two other friends to match the other tickets. All they needed was a ride, seeing as how none of them could drive yet, or at least they couldn't drive with other people in the car without someone over 21 being with them. Thus, they turned to Josh, Megan's 22-year-old older brother.

Being that all of the girls in the group were in the same after school activities, and family was often asked to come help with some of their events, they all knew Josh. In fact, he was rather popular with their group, always willing to help out, acting stupid from time to time to make them laugh, doing his best to cheer Megan and her friends up if something didn't work out for their group and team things. It also helped that he was good looking, in an average Joe kind of way. He was 6'4 with a little extra around the middle, but not much. He had brown eyes like his sister and dark brown hair that he had grown out into a ponytail, one of the few odd things about him that by now no one really questioned. Sometimes the different girls in their full group would either convince him or have his sister convince him to let them play with his hair, so long as they didn't take it too far.

Being the softy that he was for family and close friends, it didn't take long for Josh to agree to take the girls to the concert. It was a Saturday concert deal and his college and work schedules didn't include most Saturdays and Sundays. The concert was closer to his apartment than their parents' place, and because the parents had all met either him or most of Josh and Megan's family, they agreed to their 16- and 17-year-old children's requests to stay over at Josh's place the Friday night before, so long as Josh didn't mind.

Again, being the big softy that he was, Josh agreed, knowing that he had enough couches and even a blowup mattress that would give all four girls a place to sleep.

So, when the weekend of the concert came, Josh found himself inviting four 16- and 17-year-old girls into his apartment. First, of course, was his sister, Megan. Some say that because of the long hair, the siblings looked a little bit alike. She had wavy hair down past her shoulders and dark brown eyes that were hidden behind glasses most of the time. Megan was a little on the chubby side, but far from being overly so. She had an average pair of breasts and a decent enough figure, too. The only reason she was single was because she was shy most of the time.

With Megan was her friend who helped her win the tickets, Jamie, who everyone just called Jazz. She was what most people described as a punk or goth-style person. She was shorter than Megan by about three inches and had short hair that she would often change the color of and would spike randomly every now and then. Tonight she was sporting light red hair with it down and naturally smooth and soft-looking. She also wore glasses, but she wore them all the time. Her clothing style was mostly tight jeans of varying shades and stripped or random design shirts with long sleeves underneath, and she would, every now and then, wear black, fingerless gloves.

Next to come over was Bridgette, who the girls would call Bridge for short. Bridge was taller than the other three girls going to the concert and was very skinny. She didn't have the obviously well-developed body the average girl her age did, not that she hadn't had guys ask her out yet—her personality did draw in enough guys in to see her natural cuteness. Bridge had long, straight, black-as-night hair that she often wore a soft hat or hoodie over.

Last to arrive was Rachel, who also had a nickname of Rainy, or Rain for short. Rain was about the most average looking girl of the group. She wasn't the hottest girl in school, but she did have the cute bookworm look to her. Wavy, brown hair which was taken care of, average cute face, just an inch shorter than Megan, slightly larger than average 16-year-old breasts and a cute ass. Rain was the only one that would often wear skirts or dresses, which she wore and brought with her for the weekend.

By the time all of the girls were there, the mattress was blown up and off to the side for later, alongside the extra pillows, sheets and covers for when the girls decided to call it a night. Josh ordered pizza while the girls talked animatedly with each other while a movie played in the background, barely being watched. Josh would randomly throw his two cents in on their conversations, either being his opinion or making a joke that would often send the girls into a laughing fit. When he wasn't talking with them, he tried to give them their space to enjoy their time together as friends, knowing how much this night would mean to them down the road in life.

When the pizza arrived and they all sat to eat, Josh made sure to sit with them in order to talk and plan for the next day. He was sitting next to Jazz and Megan with Bridge and Rain across from him.

"Hey Josh," Rain started to ask, "Have you ever had this many girls over at your place like this?"

While it could be taken as an innocent enough question or be a jab at his love life, Jazz couldn't help but have some fun with it before Josh could answer. She smirked as she nudged him with her elbow, saying, "Yeah, stud, how does it feel having all these teenage girls staying the night with ya? Huh-huh?"

Blushing a bit at the obvious implications, Josh shook his head and said, "Ha ha, girls, very funny." This got all of them giggling as they looked at his blush and each other. Something they all knew about each other was that most of them were either single or stayed single most of the time, especially Josh. Even though he was a good looking guy that was in college, he, like his younger sister, was rather shy and didn't go out much. The few girlfriends he had had over the years Megan has either approved or disapproved of, and most of them were disapproved and watched very closely their whole time together.

And being the tight-knit group they were, most of their group, especially the four in the room, knew about the few girlfriends he had had. Thus, they were often among the many trying to encourage him or push him into going out and getting either a girlfriend or getting laid, which ever came first.

Before any more of the jokes they could think of came up, Josh decided to get some plans together. "Alright, we need to make sure we are ready for tomorrow. Because we will need to leave no later than ten tomorrow morning, let's get most of the showers out of the way tonight. This way we will all have hot water. That being said, I will be one that gets a shower in the morning because you do not want to deal with me in the morning until I've done something to wake me up."

Megan shook her head and said, "Oh, you girls do not want to see that. Just remember, do not talk to him until he's either showered or had something like tea or coffee. You either won't get a response or you'll get a glare."

Chuckling, Josh said, "You know me too well. Anyway, make sure you have all your stuff together before you get ready for bed tonight and make sure to throw away all your trash." Gathering his own trash as an example, he said, "Now, I'll mostly just stay in my room, so if y'all need anything, just come knock. Sis, you good out here?" At her nod, Josh stood up and threw his stuff away heading to his room.

All the way from standing up to closing his door, all four of the girls called out random thanks. Some were serious, others were joking or leading, the rest varied between the two. When they were alone, they turned back to each other and continued to talk about all kinds of things, and it wasn't long before they came back to Megan's big brother.

"He's so sweet, doing all this for us," Bridge said as they started to talk about Josh, knowing he wouldn't hear them from his room.

Jazz nodded and said, "Yeah, he is. How big did your eyes have to get for him to give us a ride and let us stay here, Meg?"

"It wasn't that bad. I did have to beg a little bit," Megan said, using her finger and thumb to exaggerate the 'little bit' part, "But he didn't mind, so long as he didn't have work or plans. You know I tried harder to get him to try and ask a girl out to join us?"

"Yeah?"

"Oh, yeah."

Rain spoke up at that point, asking, "Well? What did she say?"

Throwing her arms up in a big shrug, Megan said, "He finally asked her, but she couldn't make it. And the whole time before he asked her he would tell me that it was just one of those 'friend zone' things. Turns out he was right."

"Damn," Jazz said, Bridge and Rain nodding to her one word reaction, "So, please say he at least got laid before that happened?"

"Being that I'm his sister and he doesn't like to tell me," Megan said in a sarcastic tone, "No, he didn't. I'm really tempted to make him an online dating ad and find him someone."

"It's really weird," Bridge started, "I mean, he's cute, and really sweet, too."

"Maybe we can find him a girl at the concert!" Rain said, holding a finger up like the idea was an epiphany. "Do you know what kind of girl we can look for, Meg?"

Scoffing a bit, Megan said, "Yeah, girls like you guys to start with."

There was a pause for only a couple of seconds. When the other three realized that Megan wasn't going to explain what she meant, they asked her.

She merely shrugged before saying, "Well, I heard him talking to my mom last week saying that he's more popular with our girls than he was with girls when he was in High school. So, I guess we could try and find someone that would fit in with us. I mean, he likes you girls enough."

"Really..." Jazz trailed off.

Bridge, noticing her tone, asked Jazz, "What are you thinking?"

"Me?" When Bridge nodded, Jazz just said, "Well, if he likes us, why not us? Hell, I'd love to get with a guy like that."

"Yeah, I guess..." Bridge trailed off, giving it some thought.

Megan looked between them, but didn't say anything. This was her brother, but she did want him to enjoy himself sometime. She definitely wasn't interested in her own brother, but maybe... Wait, what was she thinking? He was about 6 years older than all of them.

Rain found herself agreeing with her two friends, saying, "We did say he was good looking. And he's been really nice and sweet by doing all of this just for us."

Okay, she just had to say something now. "Guys!" Megan said, getting all their attention, "You realize your talking about dating my older brother, right? My in-college, older brother?"

"Right," Bridge said after she thought about it, "I guess the age difference and us being in high school would kinda put a damper on that..."

"On dating it would," Jazz said, letting the thought hang in the air. It didn't take any of them long to see what Jazz meant by that. And none of them said anything in protest against the idea.

Megan took the pause after Jazz said that to look at all of her friends. All of them had this look in their eyes and she could tell that they all were thinking about the idea of having sex with her brother. The funny thing was, while she didn't have the same exact thought, she was thinking something similar. If they were interested and wanted to, then maybe...

"Okay... If y'all really want to, then I need to know a few things," Megan said in a low and slow tone. When neither girl said they were or were not agreeing to anything, she took that as a sign that they were serious.

"First, don't expect anything serious. For now, its just this once until you talk to him about it. Any problems with that?"

No one spoke.

"Second, if you even think you'll get pregnant, don't... you know, let him finish like that. None of us, not even Josh, needs that."

By now everyone was blushing, even Megan. But she had at least one more thing she had to say before she let anything happen.

"Last, do not let things be weird from now on. We can't tell anyone about this and if you think you'll act any different around him or each other afterwards, then don't do it. Okay?"

Finally a reaction. All three girls nodded their heads. Looking at each other, they all knew that the others wanted the same thing. And no one was speaking out against it for any reason.

"Al-" Megan swallowed to keep her throat from being any more dry, "Alright, I'll go tell him to come out here with y'all. I'll just... stay in his bedroom tonight, and be out of the way. If anything happens, it'll be up to y'all, okay?"

Again, another nod. Megan merely nodded herself and got up to go to Josh's room. Before she left them completely, she heard her best friends all say thanks in some quiet way.

Knocking on her brother's door, she heard the lock unlatch and watched as the door opened to reveal her beloved brother. He said her name and asked if everything was alright. Searching herself quickly, Megan found that yes, she was alright with this. So she made it happen.

"Josh, the girls want to see you in the main room. Alone."

Josh raised an eye brow in confusion before saying, "Why? Is something wrong?"

"No, no, nothing wrong. Its just, they want to see you for a bit. I'll just hang back in here for now, okay? Promise not to mess up anything."

Josh thought about it for a second before shrugging and said, "Alright," and made his way to the other girls. Before he could walk too far, Megan called out, "Josh."

She waited till he looked at her before saying, "Just... hear them out, okay? Consider it before you say anything." With that, she entered his room and closed the door.

Wondering what that was about, Josh entered the main room, also the living room, and found the other three girls there. One was standing behind the couch and the other two were either sitting on the floor against it or on the couch.

Bridge, who was behind the couch, motioned for Josh to sit at the seat she was behind, saying, "Here, sit down."

Wondering what all was going on, Josh went ahead and did what he was told. To his right was Rain and on the floor to his left was Jazz. As he sat down, Bridge began to gently massage his neck and shoulders.

Before he could ask what was going on, Bridge started to explain, saying, "Look, we want you to know that you are an awesome guy, and we all love you for all that you do for us."

Jazz took over from there, saying, "And we know you haven't had a girlfriend for a while now, so..."

Rain took over from there, leaning on Josh a bit while making sure her face was closer to his, "So we want to show you how grateful we are. And the best way we know how is- No, wait!"

Rain put her hand on his chest to hold him back, like Bridge was now doing to his shoulders. Josh, while he didn't believe it at first, saw where this was going. He couldn't do that to these girls! He respected them too much. They were younger than him, still in high school, even! Sure, he'll admit to finding them cute in the adult sense and not the childhood sense, and he always did think that Jazz had a nice body hidden underneath her clothes, and that one day Bridge and Rain would have some great legs, Bridge already did have a beautiful pair of legs on her now, but still! It wouldn't be right!

Before he could say anything though, Rain continued, "Look, we want to do this, Josh. You're too great a guy for us not to want to!"

"Yeah," Jazz started, "Meg said she was cool with it." Josh made a mental note to have a conversation with Megan about some things after this. "And we talked about it some more while she went to get you. If we have to do this with someone, we'd all rather it be you than some old guy or someone we don't even like."

Shaking his head, Josh started, "Girls, look, I do like y'all, but we could all get in a lot of trouble here. And besides, I can't-"

"Please?"

That stopped him. He looked up to Bridge, who had said it. She looked down at him, hands still on his shoulders. There was this look in her eye that was making him weak. He knew this was wrong. The only way this should be happening was in his head when he was jacking off. But to actually do it? With all three?

Bridge leaned down, and lightly kissed him, then leaned down to his ear and said, "Please let us do it?"

At that point, Josh knew he had lost the battle. It was a guaranteed loss when Rain leaned in to the same ear as Bridge pulled back up and started to massage his shoulders again, which made Josh close his eyes, saying, "Will you let us fuck you?"

Josh opened his eyes and turned to Rain, looking at her for a second before he leaned in and started to kiss her. Soon it turned into a deep, passionate kiss, and with Bridge rubbing his shoulders sensually and Jazz now starting to run her hands along his legs, including more and more of the inner part of his legs, Josh soon got lost in the moment. He found his hands roaming the closest body to him, which was Rain. At first it was just her smaller stomach, not toned, but smooth nonetheless. Soon enough he was groping and feeling her breasts through her dress, dipping his hand into her dress as they continued to kiss with only a few breaks to breathe.

Josh barely noticed that Bridge stopped massaging his neck as she took off her shirt, which left her completely nude up top as she didn't have a bra. As her hands started to rub his neck and shoulders again, Josh broke his kiss with Rain and looked up in order to meet Bridge's lips once again, running one hand through her hair and using his other to still grope at Rain's breasts. He could feel Jazz still rubbing his legs, but he could feel something else. It was her kissing his legs with his pants in the way. By now she was solely focused around his crotch area, and Rain was now rubbing a hand over his hardening cock.

As they both felt his cock growing and his pants becoming tighter, Rain and Jazz began to undo his belt, button and zipper, pulling his pants down and freeing his cock. As he heard a gasp and a quiet, "Wow," Josh broke his kiss with Bridge and looked down as Rain reach down to feel his balls while Jazz reached and grabbed his still hardening cock, stroking it slowly.

"That's pretty big," he heard Bridge say above him. He only saw Rain nod out of the corner of his eye as Jazz looked at him and said, "Yeah, stud, you ready for all of us girls yet?"

Nodding, as though he was fully accepting everything, Josh said, "If you girls really want it, and promise not to let anyone know about this, I'm game. Now," Josh smirked, "show me how much you want it, Jazz."

Smirking herself, Jazz got up on her knees and brought her mouth to his cock. She gave it a long lick, trying to mimic some porn she had watched in the past, before starting to actually suck on his cock. And if either girl were to ask him, he would say she was doing a good job of it.

Jazz found that she was starting to struggle with it some as it grew in her mouth. When she finally decided to see how big it turned out to be, she pulled it out and found they were all looking at at least seven inches of thick cock. Bridge had stopped massaging altogether and was making her way around the couch as Rain decided she wanted to try sucking it. She kneeled next to Jazz and slowly started to suck on his cock, putting more and more into her mouth as she got used to it.

Now, Josh liked to think the best of people, and some of his family would say that he could be naive at times, but he was no fool. Surely by now most of the girls in his apartment have at least sucked a boy's dick before, maybe even fucked someone by now. So while he could tell they were still new to this, it wasn't exactly the first time for some of them.

Maybe it was because they shouldn't even be doing this much, maybe it was because they were all only 16 or 17, and maybe it was because of that sense of them still being new to this, but Josh couldn't help but enjoy the blowjob he was getting from these girls. Rain seemed like she had the most experience, as she had kept putting more and more of his cock into her mouth, and now she was holding it to where Bridge, who had squeezed in between her and Jazz, could lick and suck on the head.

Rain started giving quiet advice to Bridge, telling her to start taking more into her mouth. While watching, Jazz took off her shirt, showing her bra. Josh always did think she had nice tits under that shirt. Seeing her decently sized tits in just a bra was a big turn on for him. Hell, just watching these girls sucking on his cock was a turn on!

By now, all three girls were taking turns sucking on his cock. Rain was holding it for each girl each time they changed mouths. Josh would moan from time to time, leaning his head back and just enjoying the sensations of the different lips and tongues working his cock. It wasn't long before he could feel himself getting close. Somewhere in his mind that was still thinking, he wondered how the girls would want this blowjob to end.

"Girls, I'm... I'm about to cum."

Jazz took his cock out of her mouth and let Rain start to suck it. "Want to cum on us? Or do you want one of us to swallow it?"

Bridge looked at Rain sucking his cock and said, "I've never swallowed someone's cum before."

"Me neither," Jazz said, "but now is as good a time as any to try it." Rain merely 'mmhmm'ed around his cock, still sucking on it. Josh, needless to say, was a bit taken back, but was in such a state of growing lust that he went with it quickly, saying, "Let me stand up and you three get ready to catch it. Just hold your mouths open when I say."

As Josh stood up, Rain clamped down on his cock with her lips, not taking them off until he had stood up and then started to suck on it some more before handing it over to Bridge. Josh quickly took his shirt off while he continued to watch the girls suck on his cock. By the time Jazz had sucked on it some and Bridge had taken it back into her mouth, Josh new he was close.

"Oh, uh, girls, get close to each other and open your mouths, quick," Josh said, taking his now wet cock into his hands as Bridge leaned back slightly and the other two got around her. They all watched intently, keeping their mouths ready and Josh quickly started jacking off in front of them. With a grunt, Josh felt himself start to cum, quickly looking down at the sexy view of the girls holding their mouths open, waiting for his cum. His first burst hit Bridge's cheek, making her jump at first. He quickly readjusted and shot his next burst into her mouth, then moved to try and hit the other two as more and more came out. What didn't get into their mouths made it to their cheeks, one burst made it into Rain's hair, and the rest dripped onto their breasts.

Panting, Josh fell back against the couch when he was sure he was done. Opening his eyes and looking at the three in front of him, Josh watched as they all swallowed his cum. Bridge and Jazz both made faces at the taste, but Jazz seemed to like it enough to grab some of the cum that fell on her and put it into her mouth. Bridge, though, seemed like she wasn't as into the taste. Rain seemed more used to it than the others, doing like Jazz and putting the excess into her mouth by hand.

With his mind not clouded by lust anymore, Josh starting thinking of how this could all come back to bite him in the ass one day. These girls were still in high school. If ANYONE found out, he would be in some serious trouble. He had to make sure that these girls remembered that, and that they knew this had to be a one time thing.

"Look, girls, we can't tell anyone about this. This has to stay between us, okay?"

Giggling, Jazz said, "Yeah, we kinda already knew that, stud. Oh, Bridge, you missed some... here."

As Jazz reached up and wiped some cum off Bridge's cheek and stuck it in her mouth, Rain said, "Don't worry, Josh, we won't tell anyone whats happening tonight. We all know how bad that could be for you, and we don't want that."

Sighing in relief that they realized that, Josh said, "Good, 'cause I- wait, 'whats happening'? You mean 'what happened', right?"

The three of them looked at each other before giggling, Rain saying, "No, I meant happening. Don't you remember what I said before?"

Jazz got up and onto the couch, sitting on his left leg and leaning against him, and got real close to Josh's face and said, "We really do want to fuck you, stud. All of us." With that, she leaned in and kissed Josh on the lips, and Josh, being shocked that they really did want to continue and go further than just a blowjob, started to kiss back in response before getting lost in the moment and starting to really make out with her. Josh let his hands start to feel and grope the girl's body on pure lust and instinct, once again his mind starting to cloud over. After all, if they really wanted to, and they wouldn't tell anyone else, why should he say no?

That was probably his last thought before just accepting everything and really getting into the events that were to take place that night.

As Josh felt all over Jazz's body, her breasts through and under her bra, her nice round ass and the wet spot at her panties where her pussy was hidden, he felt someone stroking his cock as it started to harden again, every now and then he would feel a tongue or two licking at it.

It didn't take long for his cock to get rock hard again. Breaking his make-out session with Jazz, he got up from the couch again. Before he could pull down his pants the rest of the way, Bridge was already grabbing at them. As his pants neared the floor, Josh noticed that Jazz was taking off the rest of her clothes and that Bridge was already nude. He looked over and saw Rain still had her dress on, but her tits were showing over the top part and her lower part was pulled up as she was leaning against the couch and rubbing at her pussy, her panties no where to be found at this point.

Looking between the three of them, Josh said, "Alright, how do we do this? Who's going to be first?"

None of the girls spoke up at first, merely looking at each other and realizing they didn't plan that far ahead. When no one said anything for a bit, Rain spoke up while moving to get seated on the couch, "I'll go first. Just let me get comfortable." That being said, she took off her dress and threw it off to the side before sitting with her back at the armrest of the couch, lifting her left leg over the back of the couch and spreading the other.

As he watched her slowly play and spread her pussy, Josh felt his cock really stiffen and twitch. It was a sexy sight, seeing this 16 year old play with her pussy and asking him to fuck her. Stepping out of the pants at his feet, Josh made his way to Rain's part of the couch. He stopped and leaned down to her pussy, inhaling her scent before taking a few licks at her spread pussy and tasting her juices. Feeling more and more turned on, and being able to tell that she was, too, Josh took a few more licks, slow and long, teasing Rain into moaning and whimpering.

"Oh, oh-OH! So good... Mmm... Oh, please... Just put it in... Put it in, please!"

Hearing that was enough to push him on, so Josh got up and put his cock at her pussy, holding her legs to steady himself. He looked into Rain's eyes and said, "Are you sure, Rain?"

She nodded quickly, saying, "Yes, please, do it. I really, really want it."

Smirking, Josh said, "Tell me what you want me to do, Rain, or I won't."

Biting her lip, Rain finally said, "Please, shove your cock into my pussy. I want you to fuck me, Josh!"

With that, Josh pushed his cock into her little pussy, getting all the way in and staying there. Rain gasped and cried out a bit, letting herself get used to the sudden intrusion. After a good 20-30 seconds, right as she was going to ask him to move, Josh started to slowly pull out and then push back into her pussy. Rain moaned as Josh moved into her, loving how it felt to have a real cock in her, and how gentle Josh was trying to be.

Josh was savoring every moment he could. Rain was tight, really tight, but he hardly felt any resistance when he first pushed in. If he had to guess, she either had a quick first time sex that didn't get too deep, or she broke her hymen on her own somehow. But he didn't care at that moment, because right now this little 16-year-old pussy was his, at least for this moment. And as that thought hit him, Josh began to speed up his thrusts.

Rain could tell he was starting to push faster, and harder. By now her moaning was getting louder, too. She could feel herself start to build up to an orgasm and told Josh to go harder, faster, which ever word came to mind as she got lost in the feeling of Josh doing exactly what she asked for. His hands had moved from her legs to holding her waist, trying to push in as hard and deep as he could.

Finally, Rain came, squeezing her pussy around his hard and moving cock. As she came, Josh felt her get really tight, tighter than before, and struggled to hold the feeling of his own climax. As Rain started to loosen up slightly, he started moving again at a steady pace, but Josh knew that he wouldn't last long.

Rain saw on his face that he was close, so she said, "Don't, oh, uh, don't cum inside. Cum on top of me. Cover me with it."

Grunting in response, Josh rammed into her a few more times before moaning and grunting again, pulling out of her and cumming all over her stomach, breasts and even hitting her chin one time. Both of them panting from the deed, Josh got up from the couch as he watched Rain rub his cum over her body, taking some of it and putting into her mouth like she did before.

Turning around, Josh found Bridge leaning back against the wall and Jazz in a comfy chair, both of them rubbing at their pussies while looking at him. Josh didn't even ask this time, he walked over to Bridge and pointed his still hard cock at her, motioning to it so she would get the idea. Bridge quickly got onto her knees and started sucking on his cum covered cock. She was too turned on to care that it had pussy juices on it.

When he was sure his cock was back to full readiness, Josh reached down and grabbed her by the shoulders to pull her onto her feet. He lead her to a nearby tall chair he had and had her sit in it with her legs spread wide. He looked her in the eye as he started to play with her pussy and rub at her clit, then leaned in and kissed her. He kissed down her neck then to her small but still sexy tits, kissing and sucking on both of them before he came back up and kissed her one more time on the lips.

Aligning his cock with her pussy, Josh slowly pushed in. Somehow he just knew that she would be tighter, and possibly even a complete virgin, so he continued to slowly push in, stopping at times when Bridge's moans and whimpers sounded to be more of pain than pleasure. When he did find resistance, he looked her in the eye to make sure she was ready. Bridge looked up at him and nodded, bracing herself as best she could.

Josh didn't waste time and pushed the rest of the way in and settled there, waiting for Bridge to catch her breath now that the main part of the pain was over. She was wincing, but as she took in more air, the pain seemed to fade away. Finally, she said, "Go ahead," and Josh started to move, very slowly at first, letting her get used to the feeling and any lingering pain to fade away.

Soon she began to moan and move along with him, feeling nothing but pleasure from his cock deep in her pussy. Josh picked up the pace a bit, but that didn't satisfy him nor Bridge for long.

Bridge started to beg for more as time went on, saying, "Oh, please, please more. Fuck me more. Deeper, get deeper in."

Her words and urgent tone lit a fire within him as Josh tried to push in faster but wasn't getting as fast nor as deep as either of them wanted. Finally, he just grabbed her ass from under her legs and picked Bridge up from the chair and started to bounce her up and down on his cock, making her go deeper each time. Bridge put her hands on his shoulders and moaned loud with each bounce onto his cock. Her eyes stayed closed at this point, and she was going on nothing but what her body wanted. Her mind was clouded with nothing but lust and desire for more of this cock-pumping action.

She had already come once by now, and was starting to feel another. Josh, while loving the feeling of this once virgin teen pussy still bouncing on his cock, could also feel his third climax of the evening coming. He was sweating pretty heavily now, but he could still feel a fire burning, making him want to keep fucking this girl who seemed to really want his cock.

Carrying Bridge over to a wall, Josh leaned her back onto the wall as his cock never left her pussy. He felt her legs readjust and wrap around his waist as he adjusted his own hands to hold onto her waist. When he was situated, and Bridge had one arm on his shoulder and the other against the wall, Josh started to ram into her pussy for all it was worth. Bridge gasped, moaned and cried out louder than she had all night at the sudden change in pace. She was muttering curses and cries of pleasure at random, barely able to keep her breath while Josh continuously fucked her pussy deep, hard and fast.

They both felt their climax's fast approaching with this new position, and Josh quickly muttered, "Where.... where do you... want it... Bridge..?"

She started to clamp her legs around his waist hard, barely managing to say, "In... in... inside... cum inside.. me... Oh, please... please cum inside me... AAH!"

Bridge cried out as Josh rammed his cock into her pussy one last time before he started to pump his cum into her little pussy. After two bursts of cum shot out, Bridge came, tightening and milking all of the cum that her pussy could get out of his cock.

They stayed like that for a few minutes, pressed up against the wall and breathing heavily. Josh slowly started to let Bridge down to her feet, but as she struggled to stand, he helped her slide down the wall to lean against it and sit there.

Josh looked behind him, still breathing heavy, and found that Jazz had gotten the inflatable mattress into the room and set up with a sheet and a few pillows and she was currently laying on it, either rubbing her pussy or rubbing her breasts. She motioned for him to lay down next to her and Josh readily agreed. He was tired. He had never had a night like this before. Usually, he and any girl he had been with in the past only had him cum twice at a time. He had gone longer each time but never a full three climax's. He wasn't sure how much energy he had left.

At that point, while lying on his back with his eyes closed, having nearly caught his breath, he felt the sensation of a now familiar mouth on his semi-hard cock. Opening his eyes and leaning up, he found Jazz bent over his cock, licking and sucking all of the juices off of it, making it obvious that was her goal.

Raising up to look at him, she said, "Oh yeah, you taste really good right now, stud."

As she went back to sucking, Josh said, "Uh, thanks, Jazz, but I'm going to need a few before I'm ready to go again..."

She sucked on him a few more times before she said, "Take your time, I don't mind just sucking on this cock some more."

He watched her suck on him some more before he felt a bit guilty that he was letting her do all the work while he rested. He looked over and saw Rain laying on the couch, facing them and playing with her pussy, and he saw Bridge was still by the wall resting and rubbing at her own pussy. Seeing them playing with their pussies gave him an idea.

"Jazz, bring your pussy over here. Let me see it."

She looked up with his cock in her mouth, damn that was hot, and raised up to ask, "You mean, like, 69?"

Nodding, Josh said, "Yeah, this way you're getting something, too."

Jazz got onto her hands and knees and moved to straddle Josh's face. She looked back as he ran his hands along her legs and ass, being slow in his movements to make it as sensual as possible. He lifted up and smelled her scent, finding it stronger than Rain's scent, though it could just be because it looked like Jazz had come a time or two from how wet she was. He blew on her wet pussy, making Jazz gasp out from the sudden feeling before she decided to go back down and suck on his cock some more.

Feeling her mouth on his cock again, Josh leaned up and took a long, slow lick along her pussy lips, reveling in the taste. If he had to choose, Josh would say he liked the taste of her pussy over Rain's. He gave her pussy a few more slow licks before he spread her lips apart and started to lick a little bit deeper into her pussy. He could hear, and feel, Jazz moaning as he got her pussy even more wet than before.

They continued like that for a while, and Josh could feel his cock hardening again. He knew by now that he had to fuck at least one more girl before he would say he was done, but he was running very low on energy. For now, he kept licking and lightly fingering Jazz's pussy while he lay back and rested, gathering his strength.

It was about that time he heard Jazz start moaning more often than she had been, and he noticed that she was moving her pussy against his tongue, trying to grind against him. Finally, she got up and onto her feet and turned to face him.

"I can't take it anymore, I need you to fuck me now!" she said eagerly.

Sighing, Josh said, "Alright, I just need to-"

"No, you don't move,"Jazz said suddenly. She moved to stand over him and started to lower herself towards him, making sure his still hardening cock was lining up with her pussy.

"Just let me start this off, stud. You enjoy the ride," she said as she grabbed his cock and pointed its head at her pussy. She rubbed it against her for a few seconds before starting to push it into her really wet pussy. It slipped in easily up until it met a slight resistance. Josh noticed that it wasn't as bad as with Bridge, but it was still there. Bringing his hands along her legs to her waist, he looked at her and made sure she was looking at him. They nodded to each other and he helped her slam down onto his cock all the way, pushing pass her hymen.

Jazz called out slightly at the sudden flare of pain, but bit down on her lip to keep from letting it seem like too much for her. After only a minute, she started to sway side to side, grinding against Josh to get used to the feeling.

As she swayed, Josh felt his cock growing back to full mast. Jazz could feel it too because she let out a breath of air at the feeling and moved even more to get it as hard as she could. When she was sure it was fully hard inside her, Jazz started to slide up and down on his cock. Josh rolled his head back and moaned at the feeling, his hands still on her hips.

As Jazz started to go faster on his cock, Josh used his hands to help her move and go down harder. If Jazz didn't have her hands on his chest to hold her up, her hands were grabbing and squeezing her breasts, pinching at her tits to make her pleasure levels go up.

Josh, finding his second, no fourth, wind, started to thrust upwards towards Jazz's pussy, making her bounce higher and come down harder and deeper onto his cock. As each thrust got harder, Jazz would call out louder and louder. Her back was now arched and her hands were on either the mattress or Josh's legs trying to hold her up enough to keep riding him.

And finally, Josh felt her start to tighten up on him, with his own and final climax building up with it. "Jazz, I... I think I'm... I'm about to... to cum... Where-"

"In me. Cum inside me, stud. Oh, please, pump your hot cum deep inside me!" she screeched, cumming at the last word. Her pussy was so tight against his used cock that Josh exploded his fourth load of the night deep into her pussy, his last thrust now holding her arched body up off the mattress a few inches as he filled her up.

Josh fell back against the mattress, feeling a mix of juices on his balls and on the mattress. Jazz lingered up for a bit before she slowly started to fall forward, catching herself with her arms on his chest and sinking down the rest of the way to lay on top of him.

Panting, again, Josh said, "No... no more, girls... I... I don't have anything left..."

Giggling tiredly from over at the couch, Rain said, "That's fine. I'm done for the night anyway." She yawned at the end, proving her point.

"I don't think I can take another orgasm," Jazz muttered from on top of him.

"Y-yeah," Bridge said, sounding closer than Josh remembered from where he left her at the wall. He turned his head as he felt her climb onto the mattress and lay down next to him weakly. "I'm still good from my turn before. Can't take any more..."

Josh couldn't help but smile a bit as he put out his arm and welcomed Bridge into a slight hug, which she accepted and cuddled close to him, laying on his arm. With Jazz still on top of him, Josh looked over to Rain at the couch and asked, "Want to come lay down with us?"

Rain just shook her head as she grabbed at the nearest blanket that was scattered about in the room from when Jazz had set up the inflatable mattress on the floor, saying, "No thanks, I'm pretty comfortable up here."

Nodding, Josh got a little more comfortable on his back, getting used to the weight on him. As he did so, he felt Jazz ease herself off of his softening cock and set herself a little more to the opposite side from Bridge, though she was still mostly on top of him. Looking between the three girls, no, young women, Josh couldn't help but remember that despite the very adult fucking they all just went through, they were still younger than him, and while he still wasn't sure how this whole thing had been brought on, it couldn't continue past tonight.

"Now, y'all do know that this was just tonight, right? There's no way we can all keep doing this, if that's what y'all were thinking."

"Come on, stud, can't we work something out?" Jazz spoke up from next to him.

Josh looked down at her, then looked over to the other two, and asked, "Y'all really want to do this again? Why?"

Rain shrugged from her spot on the couch and said, "It was fun. And felt so good."

"Yeah," Jazz agreed.

Shaking his head in disbelief, Josh asked, "Just what got into you girls to make you want to do all this in the first place?"

"Well," Bridge started, "We were talking with Meg about how you haven't had a decent girlfriend in a while, and she pointed out how well we get along, and well, we figured there could be something we could do to say thanks for everything..."

"And you thought of fucking around with me?"

He felt Jazz shake from laughing a bit before she said, "Are you complaining about that, stud?"

Sighing, Josh said, "No, at this point, I'm really not. That was incredible. But..."

"You know, if it helps," Rain said, starting to sound pretty tired, "We started this knowing not to expect anything beyond tonight. One of Megan's rules before she left."

Just how involved in this was his sister...

"But, I wouldn't mind doing that again sometime. Like you said, that was incredible," Rain continued.

As Josh heard Jazz and Bridge agree with Rain, he thought about what his sister said before shutting his door to his room and sending him to these young women. Consider it before you say anything. After having just fucked these women, he couldn't help but consider the possibilities of doing it again. But he knew that they didn't need to focus their love and sex lives solely on him. On the other hand, so long as they kept their word and didn't tell anyone, and things didn't suddenly become too weird and obvious that something had happened tonight...

"Alright, girls, here's the deal," Josh started, getting their attention. "So long as y'all can promise that no one says a word to anyone outside of this apartment about this, and you don't make things obviously different or awkward around others, then maybe we can do something like this again." Before he could say anymore, Josh felt two sets of lips on both of his cheeks. He looked and saw a blush on Bridge's cheeks and a smile on Jazz's face, as well as hear a happy giggle from the couch. He couldn't help but smile some himself, but he pushed on to finish his thought.

"But, there are some conditions. First off, you girls will not get pregnant. I know we went straight into things and got a little wild tonight, but from now on we take more precautions, and until then, we use condoms. I don't want us taking chances with your schooling and lives in general." He got agreements from the three girls before moving on to the next thing. "Next, if any of you find a boyfriend, or get asked out, or anything of that nature, we stop. I want you to be loyal to whoever you start to see, especially if that person can become your husband one day. I won't let you cheat on anyone with me. Got it?" Once again, everyone agreed.

"Last thing," Josh said, sounding a bit more serious than he did for the other two, "Don't get attached to me." He could feel the stare of all three young women on him at that point. "Just because we might fuck around doesn't mean we're going to be something serious. At the very least that can't happen now. You're too young for that and I'm too old for that. I'm not going to say it can't happen one day, but not any time soon." Josh stopped and made eye contact with each woman before saying, "I want you to try and find someone your own age, or at least closer to your own age. Don't ignore them or keep your distance from them because of me. I want you all to find someone one day. So don't let me be some kind of crutch or anchor that holds you back. Okay?" The girls took a full minute before they all replied with yes.

After that, they settled into a fairly nice quiet, with the majority of them tired and ready for some sleep. Josh knew that he wouldn't be getting up from his position, even when he felt one of the two ladies around him get up and set a cover over them, went and took a shower, then came back and got onto the mattress with them again. He heard the shower two more times that night before finally falling asleep himself.

The next morning, alarms started to go off and everyone began to stir. When Josh was finally able to move about, he got up and went straight to the shower, like he told the girls at the dinner table the night before. He finished and walked out in nothing but a towel and let someone else go in and take their shower while he made his way to his room to change. As he got there, he found his sister taking all of his bed sheets and covers, rolled into a big ball, out of his room. Looking in and finding that it was, in fact, missing from his bed, Josh said, "Megan, why are you changing my sheets?"

Megan had a very red blush on her face as she said, "Well, seeing as how everything was, uh, pretty loud last night, I kinda, well, I uh... made a mess."

The day went by as planned. They all got ready, grabbed anything they might have needed and went to the concert. They stood in line for a while, eventually went into the concert, had fun, left the concert, grabbed some food and made their way back to Josh's apartment to rest and straighten it up before the ladies were all taken back home. They talked a lot through that time. It was warm, friendly conversations that only once or twice made it around to what happened the night before. The girls agreed that they would like to do something like that again, either one on one with Josh or even as a group once more. Megan, being Josh's dear sister that she was, gave blessing to the idea so long as they stuck to the rules she laid down and the ones Josh laid down. And as it would turn out, they would certainly be following those rules for many times to come.
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