[Thank you to everyone who commented ideas on my last chapter. You gave me motivation for a quick turnaround time and one of my favorite chapters yet. Thanks all for reading!]
The one thing that I had really commended Hailey for throughout the duration of this crazy relationship was her ability to constantly get around her sister’s desires to have me to herself. Whether it was getting her sister to leave the house, or sneaking a quick session underneath the water or behind a bed, Hailey was the master of not getting caught. I had told her that if she tried this hard at school she’d be a future Ivy League student, but I guess this was more important to her.
That’s why, as I finished cumming inside Maddie, my third girl of the night, my thoughts really weren’t on Danielle. I knew that she was doing something with her girl friends that night, and I imagined Hailey was taking care of any loose ends. I had six gorgeous and naked cheerleaders surrounding me, and that’s all I really was thinking about for the time being.
Feeling left out of the festivities so far, Alana and Ashley, the two captains of the cheer team, had formed a very arousing 69. Alana was on top, her red hair cascading onto Ashley’s thighs, while her large breasts pressed against Ashley’s body. Underneath, Ashley was largely out of sight, but her face remained buried between Alana’s legs, furiously working at her clit. Once again, the crisp night air was filled with moans as the two girls brought each other up and down the pleasure scale.
I watched from between Hailey and Melanie, my cum still dripping from both of their pussies. It was a much needed break from a crazy night that seemingly had just begun.
Suddenly I heard what sounded like the closing of a car door. I quickly looked at Hailey, my eyes somewhat wide, but she just smiled at me and looked back to the girls. My heart skipped a beat as I wondered if Danielle could possibly be home already. There was nothing I could do at this point anyway, so I just tried to calm down and prayed that it was a neighbor.
“What the fuck?!” I heard shrieked from a number of yards away. I didn’t even need to look up, knowing that the jig was up. I was in the middle of my second cheerleader slumber party, not to mention the multiple rendezvous with Hailey and Melanie.
I was waiting for Hailey to freak out, the thought of her own fun being put in jeopardy. But surprisingly she didn’t say anything in response.
“Really?” Danielle said again. I looked up and saw her in a small black dress. She looked gorgeous and I didn’t know what to say. I had such an incredible situation going on and I couldn’t wrap my head around Danielle being pissed at me.
The other girls were sitting there with awkward faces. Alana and Ashley had, begrudgingly curtailed their activities. Just as I was about to stand up and say something, I saw Hailey start to move.
“You couldn’t expect to keep this stud locked up forever sis,” Hailey started.
“Shut up Hailey,” Danielle said sternly. “I can expect a little more trust and loyalty than this.”
“It’s not all his fault,” Hailey started to plead my case for me. “I begged him to come to this because I’ve been so nervous of not fitting in with the team. You’ve shared him with me more than once. You can’t blame him for not knowing what the rules were.”
“Hailey,” I started. “Thank you but I should probably defend myself here. Danielle, you know I care about you so much. I knew this was wrong, but I’m young and stupid. I know you don’t want to hear about how impossible a situation like this is for a guy. We’ve already discussed that a mutual attraction exists between me and your sister.”
“Plus,” Hailey jumped in again. “Don’t pretend like you don’t like girls too. You probably haven’t even confessed how bi you are.”
“So I’ve hooked up with a few girls in the past,” Danielle retorted. “Not lately.”
Danielle and Hailey traded meaningful glances, knowing that technically they had recently hooked up, at least for the purposes of being with me. Danielle looked as though she wanted to say something, but couldn’t really figure out how to put it. Her mood had seemingly softened from the beginning of the encounter, and I could only hope that there was a way out of this.
“Well girls, I brought her here,” Hailey started. “Trust me, she wants it. The rest is up to you.”
I looked up at Danielle with a shocked look, and she returned the surprised look as if to say she had no idea what was going on. Just then, Alana and Ashley got up and came over to Danielle.
“What the fuck,” Danielle started, looking a little frightened. “Hailey you’ve got to be kidding me. I’ll get you in so much trouble.”
“Oh no you won’t,” Hailey said with a laugh. “This is going to be the greatest night of your life.”
Ashley grabbed Danielle’s arms and Alana took her legs, wrestling with her until they had a firm grip. Ashley gave Danielle’s arms to Hailey, who took over holding onto her. At that point, Ashley grabbed the bottom of Danielle’s dress and started to pull it upwards, slowly revealing her. Danielle was cursing, but not screaming to the point of trying to alert neighbors to trouble. She was struggling against Alana and her sister, but they had a tight grip.
“Damn look at those legs,” Ashley teased as she continued to pull up her dress. She stopped at her panties and admired them. Then she continued to move forward, exposing Danielle’s tight body to everyone, and finally pulling her dress completely off, leaving her in just her underwear.
I didn’t know what to do, but I just knew I was turned on from the situation. I was rock solid as the girls held and stripped Danielle. Melanie noticed and came over to me, gently stroking my shaft as we watched together. She rubbed all over the sensitive underside of the head and kissed my neck and ear. It seemed she was daring me to fuck her again during all of this, but I was resisting.
“Let’s take care of this bra,” Ashley continued to tease and snapped off Danielle’s bra. Her perky breasts were now revealed to everyone.
“Look how hard her nipples are!” Alana joined in the teasing. Ashley laughed and gave Danielle’s nipples a quick kiss.
“Seriously guys, fucking stop,” Danielle said.
Instead, Ashley continued, finally pulling off Danielle’s panties, leaving her naked.
“I can see why you’re into this,” Ashley teased and looked at me. Her hands started to roam all over Danielle’s fit body, teasing her nipples as Alana and Hailey continued to hold her in place. Ashley’s hands came to her pussy, and a finger rubbed against her clit. Slowly, Ashley slipped a finger inside Danielle’s pussy and I watched it disappear.
Danielle continued to struggle but her nipples were as hard as ever, and Ashley’s finger had no trouble with her wet opening. “She’s so wet,” Ashley teased as she started to finger Danielle. I could hear the faintest of moans as everybody watched intently.
Melanie still had my cock in hand, rubbing in all the right places, increases the speed on the sensitive spots. It was getting harder to resist her, and she could sense the tide turning.
“I know you want to fuck me in front of her,” Melanie started with a breathy whisper and bit my ear lobe. “Let’s show her what a real fuck is like. Make her watch helplessly as you cum in my pussy over and over.”
As Melanie dirty talked me, Danielle’s moans were getting louder. Ashley was now face first between her legs, fingering her deeply and licking her clit.
“Good girl,” Ashley teased again as Danielle moaned and bucked against her. “Show your man how you can cum hard for the ladies.” Ashley started to suck on Danielle’s clit and Danielle thrashed against Hailey and Alana.
“She’s cumming!” Alana cheered as Danielle’s stomach rippled and her pussy muscles squeezed around Ashley’s fingers.
“What a dirty girl!” Maddie chimed in.
“Yeah she loves girls,” Ashley teased again. “Someone put a pussy in her face.”
Nicki, who hadn’t been very involved lately, came over, and the girls lowered Danielle so that Nicki could get her legs over her. She stretched across and buried her clit against Danielle’s face. Not faced with much choice, Danielle started to lick Nicki’s clit, and Nicki’s moans joined the night sky.
“Please fuck my tight pussy,” Melanie was still whispering to me. “I need to feel your cock filling me up completely.” She had her tongue sliding around my neck and ear, breathing heavily and rubbing the underside of my cock head more and more.
“I neeEE…” Melanie trailed off as I lost my composure and grabbed her tight body. With one quick maneuver, I grabbed her hips and slammed my cock deep inside her pussy. I pushed through her tight walls and felt them give to my girth.
“OH FUCK YEAH” Melanie screamed as I pounded her pussy hard and fast. Her screams and moans quickly escalated.
“What’s going on?” I heard Danielle ask with a muffled sound.
“Don’t worry,” Alana teased. “Melanie is just getting a good fucking.”
“What?!” Danielle struggled even more. From her compromised position, she could just adjust to see me fucking Melanie wildly. Danielle let out more muffled protests, but now Ashley was going crazy on her pussy. She had multiple fingers against Danielle’s g-spot and was sucking on her clit. Danielle couldn’t help but moan like crazy, even seeing Melanie and I go at it.
“Oh fuck it’s so good!” Melanie continued as I gave her the pounding she was begging for. I started to suck on her nipples and I felt her go off, her pussy squeezing me tightly as she came, even releasing some liquid onto my cock as she screamed again. I fucked her hard through her orgasm, drawing it out as best I could as goose bumps formed all over her skin.
“Oh shit,” Melanie shouted. “His cock is so thick. I feel all the veins pulsing against my walls. I…I think he’s going to cum inside me!”
I heard another muffled squeal and Danielle flailed like crazy against the girls. “Don’t cum!” I could pretty much make out.
“Oh he’s going to cum,” Alana said seductively. ”I can see it from here. His cock is so hard. He’s going to bust inside her any second. I can tell this is going to be a huge one.”
“YES cum inside me,” Melanie squeaked, her small, tight body contracting in constant orgasm. “I need to feel your hot cum so deep against my cervix.”
I grabbed her hips harder and slammed back and forth until I was at the edge, and then buried my full length inside of Melanie’s tight pussy. A second later, my cock was unloaded rope after rope of hot, sticky cum deep inside Melanie.
“OH FUCK YEAH” she screamed. “He’s cumming in me! He’s cumming so much! My insides are so warm!”
I grabbed onto Melanie’s breasts and squeezed them in time with my spurts of cum. Danielle was still saying something, but no one could hear as Nicki grinded her pussy more onto her face.
“Someone get me the strap-on,” Ashley grinned with an evil smile, as more muffled protests came from Danielle. Melanie volunteered to grab it, and quickly returned to her captain. Ashley quickly put it on, and then instructed Melanie to take one of Danielle’s legs from Alana to spread her out. Danielle kicked but was quickly spread and Ashley stood between her, ready to start things.
“So here’s the deal,” Ashley started. “You’re going to make Nicki cum. If you don’t in the next two minutes, this is going in that beautiful ass, instead.”
Danielle’s eyes widened before she quickly went to work again on Nicki’s pussy, now letting her tongue dart in and out, before sucking on her clit. Of course all the girls were counting as Danielle did her best and Nicki’s moans got louder.
“Fifteen! Fourteen!” the girls cheered. Just at that point, Nicki screamed and shook as she came on Danielle’s face.
“Aw!!” Alana teased and laughed. Before Danielle could celebrate avoiding the anal punishment, Ashley plowed the strap-on into her tight pussy. Danielle shrieked, less muffled than before as Nicki slowly moved. Maddie started to suck on Danielle’s nipples as Ashley fucked her with the strap-on.
“Fucking. Help. Me” Danielle cried out to me between moans as the girls continued their attack.
“You know you love this sis,” Hailey teased.
“You know what, why don’t you help her?” Ashley said. “If you fuck me nice and hard while I’m fucking her, it’ll make me go harder and deeper. She’ll love that!” As she finished her sentence, Maddie immediately came over to me and bent over, taking my cock in her mouth. She quickly flicked her tongue all around and worked hard until I started to respond.
“Good work!” Ashley cheered as she briefly pulled out of Danielle, pulled the strap-on up higher on her stomach to make the positions work, and then resumed fucking her. She went deeper now and started to rub Danielle’s clit, doing her best to distract her away from complaining. Hailey bent over and started to kiss her sister and Maddie resumed pleasuring Danielle’s nipples. Ashley turned around and gave me a wink, slowing down a bit to give me a target to hit. I went up right behind Ashley, pressing my body against her body and guiding my cock passed her ass and to her pussy lips. One quick thrust, and I was deep inside Ashley’s pussy. She screamed with delight and pushed back hard into my cock. Each time she pushed back and then pushed forward harder into Danielle’s pussy. I reached around for Ashley’s breasts and played with them as my cock easily hit her g-spot.
Both Danielle and Ashley actually reached their climaxes together, as Danielle gripped tighter around the strap-on and Ashley’s pussy quivered and spasmed around my cock, slowing us down until I started thrusting harder and faster.
“Oh fuck, no wonder everyone wants this cock,” she moaned as she continued to fuck Danielle. “He’s hitting my g-spot over and over. I c-cant stop cumming,” she did her best to continue to aim the strap-on while waves of pleasure overtook her. She reached back to massage my balls and rub a finger across my shaft every time I pulled out. Nicki came over and started to rub her soft hands all around my body, adding to the numerous sensations.
“Cum in my captain,” Nicki giggled as she helped Ashley rub my balls. “I think he’s getting there,” she giggled again as she felt the building orgasm. Danielle started to protest again, but that just brought on a higher assault from the girls, fucking and licking her more. This allowed me all of the time I needed to fill Ashley, and I felt the cum build and travel to my tip. With one more thrust I erupted, filling Ashley’s tight pussy with a geyser of cum. She squealed and the girls cheered as I let wave after wave spill into her, grunting with each pleasure-filled spasm.
I thought this might have been the point that the girls stopped with Danielle, but they weren’t finished. Ashley took off her strap-on and gave it to Alana, as Ashley took over leg holding duties. Alana put it on and plunged back inside Danielle to a new set of screams. Alana just smiled and grabbed Danielle’s bouncing breasts as the scene continued. Ashley looked down to the cum starting to spill from her pussy and gave me a satisfied wink.
Maddie stopped working Danielle’s nipples and moved Hailey away from her sister’s mouth, spreading across it. She placed her clit right against Danielle’s tongue, and Danielle started to flick across it. I didn’t know whether Danielle had given up resisting or if she was really enjoying things at this point. Still, the whole scene was very arousing.
“We’re going to need to get you up at least one more time,” Ashley said. At that, Hailey handed off her sister’s hands to Nicki and came over to me. She knelt down in front of me and stared up at me with her gorgeous blue eyes. If I hadn’t cum so much already, it would have made cum on the spot, or at least made me instantly hard. Instead, she just winked at me and let her tongue swirl around my cock. She rubbed her hands up and down my thighs and wherever else she could manage to reach. Every so often she would look up at me with those eyes and flick her tongue across another sensitive spot. After enough work, she finally got me up, and presented me to her captain.
“I feel kind of bad,” Ashley said, though she laughed. “We’ve been very mean to Danielle tonight. We should at least let her enjoy her man.”
I wondered how this would go. At this point, I didn’t know whether Danielle hated me, was going to get over things, or was too horny to care. Still, it took me off guard when Ashley whispered to me that I should fuck Danielle’s ass. I had done it once before, and it was incredible. Danielle still had the most amazing ass I had ever seen.
I was guided down below Danielle to the point where I probably could have her ride me. However, Hailey went and grabbed the lube to set me up for something Danielle didn’t even know was coming. They lowered Danielle enough to reach my cock, and at first I teased her against her clit. I got a small indication that maybe things would be okay, as Danielle bucked against my cock, seemingly trying to take me inside. Hailey eagerly grabbed my cock and covered me in the lube before releasing me. I slowly slipped down Danielle to her ass and pressed against her. She screamed out against Maddie’s pussy, only causing her to moan from the vibrations. Before Danielle could protest much more, I had managed to slide halfway into her tight ass.
“Wow look at that,” Alana said, seemingly in awe.
“That ass is pretty perfect,” Nicki chimed in.
“He’s going to break her, AH” Maddie laughed and then cried out, perhaps from Danielle sucking harder on her clit from the comment.
I got as much as I could inside Danielle’s ass and then started to thrust in and out. Alana had the strap-on filling her pussy, and Danielle was soon being double penetrated by me and the faux cock.
“Oh shit she’s cumming already!” Alana cheered out as Danielle squeezed both the dildo and my cock as her holes puckered.
“How does it feel?” Ashley asked me with a grin.
“I love her ass” was all I could say with a smile as I continued to thrust in and out of her tight opening. I looked up and took in the sight of her gorgeous ass. I had a fleeting moment of sadness and regret at what I had done, and really hoped that my semi-relationship with Danielle could manage to continue. That train of thought was quickly broken by the pleasure I was feeling surrounding by Danielle’s ass. I watched as some of my cock disappeared with each thrust and the sight turned me on.
“I don’t think she’s going anywhere at this point,” Ashley said, and finally released Danielle’s leg. She wouldn’t have much room to work with two people firmly steadied between her legs, and Danielle let it fall to the floor. Ashley came over to me and kissed my neck and up and down my body. Then she presented her chest for me and I sucked on her nipples as cock continued to disappear in rhythm into Danielle’s gorgeous ass.
“I’d love to see you cum inside that ass,” Ashley cooed as she rubbed her chest against my mouth. She put a hand on my balls again and did her best to arouse me more. All of my previous orgasms ensured that I could last longer than usual in the situation. I could only guess I would have cum pretty quickly had this been the first of the night. I eagerly sucked on Ashley’s breasts as I made sure to keep one eye on Danielle’s ass. Danielle was cumming pretty frequently now, with both of her holes filled to the breaking point. She was screaming but it muffled into Maddie’s pussy, causing Maddie to orgasm from time to time. These had to be the type of scenes heaven produced.
“Oooh, there you go,” Ashley purred into my ear as she felt my cock starting to get harder. “Let’s see what it’s like when a beautiful cock fills up a gorgeous ass.” She continued to rub me, making sure that this particular orgasm was going to be a huge one. I held back for as long as I could, also ensuring a large and forceful orgasm, until I finally couldn’t stop it, and I blasted quick and powerful jets of cum deep into Danielle’s ass. I heard muffled screams, but there was no denying they were of pleasure, coming from Danielle as her ass clenched around me, milking my cock for all it had. All I could think to do was to run my hands up and down Danielle’s body sensually as I filled up her ass for just the second time ever. I still wanted her and I wanted to give her a hint of that, even in this clusterfuck of sexual insanity.