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.