As I schemed to get another girl added to my list of approved side chicks, I realized that I had a problem that wasn’t going away. Danielle was trying as hard as possible to make this work, and was giving me as much freedom as I could realistically hope for. And, yet, I still wasn’t satisfied, and continued to crave other girls. The real question was whether I would be up front about things with Danielle, or continue to try to keep things on the down low.
Labor Day weekend arrived, and with it, a much needed three day weekend. School hadn’t been going for very long, but even a week or two was enough to make me pine for a break. Danielle’s family was away for the first part of the weekend, and I used the rare down time to relax, play video games, and actually hang out with guy friends for a change. I hadn’t realized how much I had ignored my main group of friends during this recent run of good fortune I had been experiencing, but every now and then, it’s good to get that chill time in.
By the time Sunday rolled around, I had received a text from Danielle about a Labor Day party that her family was throwing the next day. It sounded like a good time to hang with Danielle and Hailey, and perhaps say more than few words to their parents. I spent most of the day finishing up a project, so that I would have all the time I needed the following day.
Even with the party set to start in the early afternoon, weekends were for sleeping, and I enjoyed staying in bed for the morning. After surfing the computer for a bit, I grabbed some breakfast, and slowly started to prepare for the day. It wasn’t long before I got a text from Hailey, asking where I was. I hadn’t seen her in a few weeks now, and she must have missed me. In fact, as I finished getting ready, I couldn’t help but remember that the last girl I had actually fooled around with was Melanie. But that was a situation for another day.
As I had become quite accustomed to doing, I began my journey to the girls’ house on foot. It was another brutal day, and it wasn’t long before my shirt was sticking to my skin. All I had with me was a towel, and my attire of a shirt and blue swim trunks. Approaching the house, even from down the street, I could hear shouting and splashing. I could only imagine there were many people having pool parties and barbeques on this holiday. Things only got louder as I approached the house, as I found the side gate open and made my way to the back.
I quickly realized that all of the noises I had been hearing were coming from this backyard. My eyes nearly bugged out when I noticed the body count running around the pool area. There were at least half a dozen girls, some of whom I had never seen before, and that was in addition to Danielle and Hailey. That’s when it hit me that this was another cheerleader party.
“How could this be” I thought to myself. I couldn’t imagine how Danielle had allowed this to happen. It wasn’t long ago that we had just discussed keeping things to her and Hailey. And, now, here were these girls, some were even part of that infamous night with Danielle. My confusion was only allowed to continue for a few moments, before I was spotted. I braced myself for a rush, but it was only Danielle who came to greet me with a hug. She was dressed in a skimpy black bikini, and looked as gorgeous as ever.
“I trust you” she said, as if she could read my thoughts about the situation. Though Hailey had convinced the girls not to attack me, she hadn’t been able to stop them from observing. Most had their eyes pointed in my direction, and that attention doubled as I tossed my shirt onto a lounger.
As if the situation needed to be any more puzzling, Danielle’s parents were not completely scarce from the situation. Her father was stepping in and out of the back, cooking up burgers and hot dogs. Her mother was reading on the other side of the pool, gracious enough to give the party some space, but not enough to remove herself entirely.
As I made my way into the pool, the greetings finally started to come in. Hailey finally hugged me, her wet body, decked out in a blue and green bikini, quickly dampening me before I could get down the steps. I heard a few “hi’s” coming from the hot tub area, and recognized the busty redhead Alana, as well as the blonde team captain, Ashley. Nicki (the perky Asian) and Maddie (the extra fit blonde) were also there, giving me subtle glances of excitement. The other two girls looked unfamiliar, but I imagined I would get to know them at some point.
The day started off innocently enough. The girls pretty much laid off me, and Danielle seemed happy with the situation. We played a quick game of volleyball, before everyone got out to get some food. I finished first, and made my way into the hot tub area. Getting there first, I figured I would let whatever come to me. It wasn’t long before many of the girls started to join me in the hot tub area, though again, most kept their distance.
The stunningly hot day had given way to the evening, and a slight breeze helped to make the hot tub the place to be. I took a deep breath, taking in the fresh air, as bubbles filled the jacuzzi. Their dad had been gone for most of the last hour, and their mom had finally headed inside a few minutes ago. All nine of us, including the six girls from Hailey’s cheer team were in the hot tub.
“I think there are some people who don’t know each other” Ashley said, breaking the brief silence. “That’s Jessica” she said, pointing to a busty girl with brown hair. She arguably had Alana beat in the bust department, which was impressive. “And that’s Allison” she continued, motioning towards the blue eyed blonde with brown highlights and brown eyebrows. Something about the combination worked for her, and I extended a hand to each of the new girls.
“New members of the team?” I asked with a warm smile.
“Yep, better late than never I suppose” Ashley said with a giggle. “They barely beat the deadline, but they’ve been worth it so far” she continued with a suggestive tone. I sat there slightly confused until I remembered the first time I had seen the cheerleader party, and watched the girls get each other off.
“So enough about us, how’s school for you?” Alana interjected.
“Oh you know, same old boring shit” I said, drawing a few laughs from the girls. “Things are-” I started before being taken off guard by a strange touch. Danielle was on my right, happy to be keeping an eye on the proceedings. However, it was starting to get darker, and the jets veiled the water line. I had a hand in my crotch, and my instincts told me it wasn’t Danielle. I looked subtly to the left, where Allison was sitting next to me. “Things are so boring, you know how it is” I finally forced myself to finish, so that nothing got strange. My eyes kept looking towards the left, and as I got hard I saw Allison’s mouth open in amazement. Ashley mouthed “I told you” to her, before turning her glance back towards the middle.
“Can you believe what Michelle was wearing today?” Hailey said, stealing the conversation, as she had done before when trying to get attention away from me for a friend. She was always giving like that. As the girls started to mutter excitedly, I felt the hand dip inside my trunks, up the left leg hole and onto my hard cock. Allison spent a few minutes exploring, getting a handle on my size. I saw her give a quick wink to Hailey, and instantly Hailey started to ask Danielle about school.
“That teacher still giving you trouble sis?” Hailey asked, as Allison started to move her hand on me. With Danielle’s attention on her sister, Allison had a bit more freedom, working me under the water, as she exchanged knowing glances with a few of the girls. Her hand pumped my length, and then she ran her finger along the underside of me. Suddenly, I felt something else, and could see Alana leaning down ever so slightly from her position. She had the soft part of her foot on the underside head of my cock, and was rubbing it in rhythm with Allison’s pumping.
This had probably been the longest I had gone without getting off in a while. So, even though the work was, sometimes, clumsy, it was still effective in getting me going. I was smart enough to turn in Danielle’s direction on occasion, nodding and responding to her story. She was off on a rant about her teacher, as Hailey kept her attention with follow up questions. Allison got a better grip on my cock and started to rub the bottom of my head more against Alana’s foot. I did my best to keep from squirming too much as the pleasure built. I looked over to Allison as I approached my climax, and received a piercing look of sexuality from her gorgeous blue eyes. She even raised her darker eyebrows and grinned as she brought me over the top. I managed to keep myself quiet, only closing my eyes briefly as I started to shoot my load through the water. Alana removed her foot, and Allison pumped me through the orgasm, as any evidence was quickly washed away by the jets.
Surprisingly, that seemed to satisfy the girls for a while. There was no shifting of positions so the next girl could get a chance. No girls were turned towards the jets getting off, and it appeared that none even had their hands below the water.
After some more chatter, a phone went off. It was Danielle’s and she groaned as dried a hand to answer.
“Hey…are you serious?” she said in shock. “It’s due tomorrow? Son of a bitch.” Danielle hung up the phone and got out of the tub, quickly drying herself. I gave Hailey an “are you serious” look and she had to hold in a giggle.
“Guys, I’ll be right back” she said. “I don’t want to miss the party, but I have to work on this a bit. I’ll probably do some of it outside. Give me a sec.”
Danielle quickly disappeared into the house, too distracted to even give a second glance.
“Me, me, me first, no, me” I heard from all the girls, as they all started to get up. Some girls were even grappling, holding one another back so that they could get to me first. The seven girls remaining in the tub all had partners in their respective fights to get to me – except Nicki. She made her way over to me, undetected, yanking my trunks down and immediately sinking her tight pussy onto my cock.
“Oh fuck you Nicki” Ashley laughed, as the girls started to end their wrestling. Nicki was too lost to care, her body facing me as she wasted no time in riding me. Her Asian descent had resulted in a beautiful skin color, and she was determined to give me any look I wanted. She pulled her bikini top up, pushing her bouncing tits right in my face. As nervous as I was about Danielle’s imminent return, I greedily sucked on her nipples.
“We don’t have much time” Hailey said, one of the few who cared about that side of the situation at the moment. “Hurry up guys” she said, coming over to us, using one hand to rub Nicki’s clit, and the other to massage my balls. As I said before, Hailey was very generous in these situations. She was determined to let me have my fun, without getting into trouble with her sister.
“Unh fuck” Nicki moaned as she rode my cock hard, starting to go limp as she climaxed. She stiffened, and Hailey had to help keep her upright as her tiny pussy went off around me.
“There’s no time you slut” Hailey giggled, and started to bounce her friend on my cock, making sure the spasming pussy was also riding me towards climax. “Fucking cum in her already” Hailey moaned in my ear, before giving my neck a nibble. She knew what would help get me over the edge, and between the neck attention, the rubbing of my balls, and Nicki’s spasming pussy, I finally got there. I took Nicki’s tits into my mouth as I came hard, firing ropes of hot sticky cum deep into her pussy.
“Oooh looks like he’s cumming” Ashley teased.
“Lucky bitch” Maddie joined in, laughing.
“Couldn’t resist filling up that tight little Asian pussy” Allison moaned from next to me, giving the other side of my neck a quick kiss.
“Mrs. Gregor is a bitch” Alana said hurriedly. In an instant, Nicki hopped off my cock, my spent rod falling out of her tight warm hole as the girls returned to their spots. A few seconds later, Danielle slid the door aside and appeared with a laptop.
“Really?” I whispered, catching onto what must have been a code phrase. Hailey shushed me and smiled.
“Sorry guys, I’ll try to do most of this out here,” Danielle said, sitting down and dipping her feet in the water.
“Homework?” Hailey asked.
“Yeah, somehow there was this history project I forgot about” she said, still a bit flustered. I wasn’t entirely sure what was going on here, but I could only guess Hailey had told a friend to call Danielle and make up a project.
The evening continued on with more gossip, chatting, and questions. In Danielle’s eyes, it had been a near perfect evening, at least as far as her worries about me were concerned. For everyone else, the evening had been pretty great, too.
“Have to pee, be right back” Hailey said, excusing herself from the hot tub and heading inside.
“Are you fucking kidding me?” Danielle said moments later. “The internet is out now? Really?” Hailey might have been busted, if it hadn’t been for their shoddy internet connection, which went down fairly regularly. Hailey made sure to spend some extra time inside, so she wouldn’t emerge as soon as things went down. She finally came back out and re-joined things as if nothing had happened.
“Damn it, I’ll be right back again” Danielle said in frustration, heading back inside to try to figure out the internet problem.
As soon as she disappeared, the girls were at it again.
“Ok Nicki” Ashley said, emphasizing her name. “You’re filled so you can be on watch duty.”
“We should have more time” Hailey jumped in. “She’ll have to ask our Dad and he takes forever with this stuff.”
Without warning, Allison made a quick maneuver and ended up on my cock, impaling her tight hole on my shaft.
“You fucking sluts” Ashley groaned and started moving towards her.
“Let her go” Hailey said, pulling on her. “We don’t have time for fights tonight.”
Ashley grunted but relented. Allison started to ride me, a bit slower than Nicki, but with sexier looks on her face. Something about the darker eyebrows under blonde hair worked well for her, and she was using it to her advantage. She put her face against mine, and before I knew it, we were making out like it was our last night on earth. Our tongues wrestled for a while, before she pulled off the kiss, and stared at me with a look of ecstasy. A few seconds later, her pussy was contracting around my cock, as she threw her head back in pleasure.
Maddie saw the opening of my mouth, and quickly got out of the tub, straddling my face between her super toned legs. She pulled her bikini bottoms to the side and dropped down, letting my tongue start to work its magic on her pussy. I held onto her tight thighs as I worked my tongue across her clit, sometimes darting inside her. Allison was riding me harder now, determined to hit a second climax, taking one of my hands away from Maddie’s legs and putting it onto her nipple. I twisted and teased it, which brought Allison over again, sending her tight hole into another spasm. Maddie started to shake over me, and released a small squirt onto my face as she came, eventually falling back into the hot tub with a reverse sumersault and splash.
Sensing we might be short on time, Hailey and Ashley came over, each sending their hands on an exploration across my body. Ashley finally found my balls and started to rub, while Hailey kissed my chest.
“There we go” Ashley said with a triumphant grin, as she could feel me starting to pulse. “You can’t resist cumming when I play with your balls can you” she teased and sucked on my lower ear. I shivered, unable to fight the sensations, and quickly started to rocket cum inside Allison. I bucked against Allison’s pussy, unable to fire the cum quickly enough, as I filled her with a gigantic load. Ashley giggled and remarked about how big the load was, though I barely heard her. I wasn’t going to come down from this high easily, as Allison stayed submerged on my rod, even after I was finished.
“Time for more?” Alana asked, as the girls looked back towards the house.
“I wouldn’t” Hailey said. “Shouldn’t be much longer. Let’s not blow this for the future” she said with a big smile, and a wink towards me. The girls reluctantly returned to their positions, as I tried to catch my breath.
“That was some load” Allison whispered, attacking my neck with a few more kisses. She had quickly learned what I liked, and that was an added turn on. I started to realize that Allison could be another girl that I would enjoy this reguarly with.
In fact, it was starting to become clear that it didn’t take much for me to form a sexual, lust filled bond with a girl. A day ago, I was trying to figure out how to bring up Melanie to Danielle. That, of course, was after solving the Hailey issue. I had to admit to myself that I was young, horny, and not in a position that I wanted to give up this amazing situation.
My thoughts were interrupted as Danielle came back outside.
“Sorry, this is becoming a ridiculous night” Danielle said, sitting back down and returning to work.
“That’s for sure” I said in my head. From the looks around the hot tub, many were thinking the same thing.
The rest of the night was rather uneventful. Danielle finished her project, which I still hoped might be legit, for her sake. Eventually, people grew bored of being wet, and the girls filed out of the jacuzzi. Allison was the last to leave, and as she walked inside, she pulled her bathing suit aside long enough to give me a look at my cum dripping from her pussy. She winked and went inside the house.
“What a night” Danielle said, as we started to bring stuff in from the backyard. “And there’s school tomorrow. I can’t believe all those girls are staying over on a school night.”
I couldn’t help but have flashbacks to the last cheerleader slumber party, when I went exploring and ran into quite the night.
Danielle and I spent some time in her room, talking about school and the next weekend plans. There was no doubt that we still connected on an emotional level more than anyone else, but I was starting to question if that was important at this point. Yes, if I admitted everything to her I could lose her, and who knows how that would effect the relationship with her sister and friends. Right now, I couldn’t bring myself to throw a wrench in things.
I felt a little guilty when Danielle thanked me for keeping my composure tonight. She also apologized that she wasn’t in the mood for things, as her time of the month was in full swing.
During the last sleepover, I had made my way into Hailey’s room after falling asleep briefly, and they had wondered what took me so long. Tonight, I wasn’t even sure if I was heading there. But, after a few hours of sleep, I found myself needing to use the bathroom. After I was done, I passed Hailey’s room and noticed the lights were still on. I took a deep breath and made my way inside.
“Look who finally decided to show up” Ashley laughed. However, no girls jumped on me, and there were no wrestling matches to get to my body. Even Hailey seemed a bit confused by the lack of action.
“So Hailey told us that it’s been a while for you two” Alana started. “She does so much to help us have fun, and we all appreciate that.” The other girls nodded enthusiastically.
“It’s your turn” Nicki said with a smile in Hailey’s direction.
She looked at her friend’s appreciatively.
“We’re going to help though” Maddie laughed. “He might not last long with all of us involved.”
Hailey giggled and made her way over to me, seductively. I had forgotten how unbelievably sexy her blue/green eyes were. She wrapped her arms around me and we kissed passionately. The other girls went to work, stripping the both of us of our clothing, and soon we were kissing naked, bodies against each other.
After a few minutes, Hailey grinned at me and dropped onto all fours. She spread herself just enough for me, and I couldn’t help but excitedly get into position. I gave her beautiful ass a few playful spanks, and then shoved myself into her pussy from behind. I felt myself filling her every inch, easily rubbing her gspot. It was almost like I hit a switch, and Hailey’s composure dropped. She hurriedly started to push herself back against me, and I found myself grabbing her hair in my hands and pulling as I pounded into her. The girls all found a spot to assist things. Two girls were on each of Hailey’s tits, sucking a nipple in each mouth. Another was near the main action, licking Hailey’s clit as I fucked her hard. Another girl slapped Hailey’s ass in time with my fucking, while yet another was behind me, rubbing my balls. The remaining girls all kissed or licked parts of Hailey and I, and the sensations drove us both wild.
With sensations on all of her most sensitive spots, Hailey started to cum in waves, virtually never coming all the way down. Her pussy would clench, and she would leak juices around me. She would try to catch her breath, only to end up cumming again and again. I had to fight all of the sensations to try to give Hailey a nice fucking, though it was a difficult battle with all of the girls paying me so much attention.
“Sorry if we don’t let him last long” Nicki said with a giggle.
“That’s ok” Hailey panted. “I love when he cums inside me.”
That seemed to renew the girls’ energy. I looked around and still found the sight hard to believe. All of these gorgeous girls, with my cock continuously disappearing underneath Hailey’s ass. I felt a tongue start to work at my balls, as one of the girls was down on the floor, trying to help me finish. As I got closer, Hailey knew what I wanted.
“Let him play with my tits” she said, and the girls beneath her laid off her chest. I lustfully squeezed and rolled Hailey’s tits in my hands, which felt even bigger with gravity pulling down.
“Ooh he loves Hailey’s perky little titties” Maddie cooed as she kept some light pressure on my balls.
“Fill her! Fill her! Fill her!” the girls started to cheer. I held onto Hailey’s tits hard as I buried myself completely inside her, before starting to fire off my first few ropes of cum. The first few came out in quick spurts, before longer ones continued to paint her insides. Hailey dropped her front half onto the floor, as I poured everything I had inside her. She turned around, facing me, with my cock still buried deep inside her, and came up for a long kiss.