[This is a shorter chapter and I'm looking for thoughts on where to go next. I can either continue the cheer party, have Danielle get involved positively or negatively, or move on soon. Looking for girls to role play and dirty talk with too. Thanks for reading!]
After my glorious weekend with Danielle and Hailey at the hotel, it was time to return to reality. The prospects of another week of school seemed overwhelming, especially since I had not even considered homework during the trip. I half assed most of the assignments on Sunday night and got as much sleep as I could.
I had to admit, I was even more preoccupied than usual. Hailey had done an incredible job managing to stay sexually engaged with me, constantly finding loopholes around her sister’s rules. I pretty much considered Danielle my girlfriend, but there was no doubting that this was a weird situation. It was an amazing one, but not without its awkwardness. I knew things couldn’t stay this perfect forever, so I made it a point to enjoy things as long as they lasted.
But there was a situation to deal with. Hailey had whispered something to me before I left to return home on Sunday night. It was something that I knew would come back around again, and something that was going to divide my internal thoughts to the most extreme level.
It was time for another cheerleader party. That coming weekend, Hailey confirmed that there would be another slumber party, although the location had not been decided yet. She had kind of hinted to me that it was up to me. Everyone had so much fun at the last one, that if I decided to make myself available, the girls had no problem with another night at Hailey’s house. If I wasn’t going to get involved, it would probably end up being another girl’s turn to host.
The original cheerleader slumber party was probably the greatest night of my existence. I lost count how many girls I filled up and the experience of feeling so many different tight, young girls on me was incredible. I couldn’t even hide my arousal at the thought of experiencing all of that again.
However, on the other hand, there was Danielle to consider. She had been an amazing sport when it came to sexual exploits with her sister, although she hadn’t exactly not enjoyed things. In fact, seeing her in the hotel room with her sister the other night had me briefly thinking of inviting her to the cheerleader party. But how in the world would I broach that subject?
“Hey Danielle,” I could picture myself starting. “As long as you’ve been so cool including your sister in our sexual games, how would you feel about adding another half dozen girls to the equation?”
No, I couldn’t do that. I had every intention of making my times with Danielle special, regardless of what my decision was. I lusted after Hailey and her cheerleader friends, but I really cared about Danielle on an emotional level. What we had was different.
Still, I couldn’t help but think back to that night. I pictured Alana and her incredible rack. I remembered how cute Melanie was, both times that I had fucked her. All of the girls were so gorgeous, and if I was to go wild and crazy one more time, it was hard to think this wasn’t the time.
“So what’s going on this weekend?” I asked Danielle on Thursday afternoon, still undecided on the weekend’s plan.
“I’m not sure,” she started, dressed in a blue t-shirt and jeans. “I’ve been kind of neglecting my girl friends lately.”
“You can see them,” I started. “Obviously I want to hang out with you every day, but you can’t lose your friends.”
She nodded. “You sure you don’t mind?”
“Of course not,” I smiled. I still wasn’t sure what my choice was, but this at least made things easier on me.
I went home on Thursday night and had the internal debate. Finally, I settled on texting Hailey. I knew she wasn’t the most impartial judge, but it couldn’t hurt.
“What do you think?” was all I wrote.
After a few minutes I got a response.
“Look, I know you are conflicted. I know you like my sister. I can’t tell you what to do. But you’re young and it’s not like you two have been very exclusive lately. Remember last weekend. ;)”
She was right. The threesomes with her sister didn’t scream exclusivity. Still, there’s no way she would be cool with these extra extra-curriculars. When it came right down to it, I was still young, still had a lot of time to settle down, but these opportunities weren’t going to last forever.
“Invite them” I sent back to her, and then went to sleep.
Danielle had made plans for a big girls night out, though I didn’t know whether it was going to be an all-night thing. Though I felt guilty, I was full of excitement as I made my way to Hailey’s house. I was dressed pretty simply, just wearing a t-shirt and shorts, and had a swim suit with me. I knocked on the door and Hailey opened it with a giant smile. She gave me a huge bear hug.
“This is going to be so much fun,” she said. “Everyone was so excited to hear you were coming.” Hailey was wearing tight, yoga shorts, which shaped her butt perfectly. She caught me staring and shook her ass at me with a wink.
“You can touch,” she laughed. “I won’t tell anything that happens tonight.”
I let my hands explore a little, but didn’t want to get too riled up already. And before long, the doorbell rang, signaling the arrival of the first guests.
Walking in was Ashley and Alana, the blonde and redhead busty captains of the cheer team.
“He’s here!” Alana grinned wildly and ran over to me with a big embrace. Her breasts pushed against me through her tank top as she held me for a while. Ashley followed up with a big hug of her own, also dressed in the familiar tank top and cheer shorts combo that had become a staple of these events.
“Same group as last time?” I asked the girls.
“Actually no,” Ashley started. “I’m sure you can guess there are more than a handful of girls on the team. After word got around of the last party, every girl wanted in. It wasn’t an easy selection process, and the only girls who were guaranteed were the captains, and of course Hailey for bringing you to us. We had different types of competitions throughout the week to determine who would be able to come. Andrea cried when she didn’t make it. Actually, nobody made it from last time.”
“Except Melanie,” Alana pointed out. “It was strange. She’s never really all that into anything. But this week, she was an animal. I guess we know what motivation she needs.”
We all laughed as I remembered back to the first time I fucked Melanie, along with the second time, when Hailey distracted Danielle with video games. She seemed so shy, except when it came to this. I was excited to hear she was coming.
“So tonight you’ll meet Nicki and Maddie,” Ashley said suggestively.
No sooner had she said this than another ring of the doorbell went off. Hailey excitedly galloped to the door and opened it, letting the two girls inside. The girls all exchanged hugs before the two new girls slowly made their way over towards me.
Nicki was a beautiful girl, who appeared to be from an Asian descent. She had tanned skin, some freckles, and very nice and perky breasts. Maddie was a cute blonde, with curly hair and a fit body. She must have been the gym rat of the group and you could see her trim arms and legs.
“Don’t act so shy girls,” Ashley laughed. “It’s certainly not going to last.”
“Let’s just start in the pool,” Alana said. “That will help everyone get their shyness out of the way.”
I went off to go change into my black swim trunks and the girls all threw their clothing off, revealing bikinis of different sizes and colors. Everyone ran out into the backyard and I started to admire all of the girls’ bodies. Nicki’s breasts were really nice, poking out noticeably over her bikini top, and Maddie’s body was incredible. Maddie and Alana were the only two with abs.
“Like what you see?” Alana giggled as she noticed me checking out the two new girls. “Wait until you see his cock, girls. You’ll never want to leave.”
The girls all giggled, and Nicki and Maddie blushed a little.
“I can’t fucking stand the shyness!” Ashley yelled and grabbed Nicki’s bikini top, ripping it off. I couldn’t help but stare at her incredible breasts. Alana was quick to follow with Maddie, exposing her smaller but still perky breasts. “There, now we all know what they look like!” Alana, Ashley, and Hailey followed up by tossing off their tops and it wasn’t long before everyone was topless.
“Well, that didn’t take long,” Alana teased me as she noticed my erection poking painfully against my swim trunks.
“Don’t you dare start without me!” a voice came yelling from around the side of the house. Melanie was running towards us, already stripping down to her bikini. She embraced me in a big hug, and playfully grinded her leg against my cock.
“Oh look who’s here,” Ashley teased. “She didn’t want her little boyfriend to get shown a good time.”
“Shut up!” Melanie blushed and pouted. I could only think to myself that a third girl was all I needed in this crazy equation.
“She talks about you all the time,” Alana laughed. “You should have seen her in practice all week. Yet she won’t even show you her tits, when we’re all topless.”
“Of course I will,” Melanie said and quickly untied and threw her top off. She shoved her perky breasts into my face and I smiled and started to suck on her nipples. She moaned loudly and put her hands on my head.
“Easy there,” Ashley said and pulled Melanie away. “We just got here. You don’t have exclusive rights to him.”
“Yeah,” Alana started. “And you know what, I just realized something. Last time we were here, he didn’t even get to fuck Hailey. If it wasn’t for her, we wouldn’t even know him. It’s only fair she gets the first one tonight.”
Hailey cheered with glee. She had fucked me a ton already, but that didn’t mean she didn’t want it just as bad as they did. Without hesitation, she untied her bikini bottoms and showed off her tight, shaved pussy to the group.
“I want to do this in a crazy position,” Hailey said excitedly. She put her hands on the ground and lifted a leg into the air. “Grab my legs and hold me them up in the air.” The two captains were happy to grab her legs and raise them up, spreading them wide in front of me. Even in this position, her pussy looked plenty tight and inviting.
“Please fuck me,” she tried to look at me from her compromised position. I smiled at her and dropped my swim trunks, showing the group my cock. Nicki and Maddie gasped as I moved behind Hailey. I pushed my cock against her clit and rubbed.
“Don’t even start teasing,” she moaned as my head rubbed back and forth. Finally, I moved to her entrance, centering myself and pressing forward, returning my cock to a familiar spot deep inside Hailey’s pussy. She screamed out as I quickly went to work thrusting in and out of her. She was so tight, but between the position and her self lubrication, I had no problem pounding her fast, hard, and deep.
“Fuck I love this cock so much,” Hailey shouted as some blood rushed to her head. I playfully spanked her firm ass, and she shrieked with delight each time my hand came down. I let my hands run up and down the smooth skin of her body, which made her continuously shiver from the extra sensations. I reached around and started to rub her clit, sending her into an orgasmic spasm. Her tight pussy gripped my cock and massaged it as she squirted liquid onto my head.
The girls all started to cheer.
“Look at her cum hard!” Ashley smiled.
“She squirted on his cock!” Alana said.
“Bet he cums soon,” Maddie joined in. I smiled at her as she started to warm up to the night.
“Well, it is his first one,” Alana said. “It should be quick. We know how much he loves Hailey’s little pussy.”
“He’s getting thicker!” Hailey screamed between gasps, laughing from the continuous blood rushing to her head. “Please cum inside my pussy! I need it!”
Alana and Ashley rubbed my chest and body as my orgasm built. With a grunt, I buried myself deep inside Hailey and let loose, shooting rope after rope of cum.
“Fuck! Fuck! Fuck!” she screamed and giggled with each rope that coated her inner walls. I could feel the big vein in my cock contract with each pleasure-filled spasm, and I let myself empty inside of Hailey.
They finally put her down and she smiled wickedly as my cum dripped from her pussy. She grabbed a hold of me to keep her upright and kissed my lips hard.
“Let’s see the rest of the new girls,” Alana said and quickly pulled off the bikini bottoms of Nicki and Maddie. They were both shaven and looked amazing. I still couldn’t believe the situation I was in, but I was determined not to question it.
“I think Melanie is going to cry if she doesn’t get his cock soon,” Alana giggled. Melanie pouted again and Ashley came over to whisper something in Alana’s ear.
“Ok,” Alana grinned wildly. “You can have his cock right now. Under one condition.”
Melanie looked at them worriedly.
“You have to get anally fucked by Ashley with a strap-on at the same time,” Alana revealed the wicked plan.
Melanie turned a little white. For as slutty as she had seemed for my cock, she was still a relatively inexperienced and shy girl, who certainly had never felt anything in her ass before.
“Scared?” Ashley winked, going over to her bag and pulling out the strap-on. She sucked the tip into her mouth and tied it around her.
“Fine, do it!” Melanie dared. “As long as I have his cock inside me, I don’t care.”
The girls all smiled and instructed me to lie down. Maddie and Nicki were put in charge of getting me hard again while Alana and Ashley put Melanie into position. She was going to ride me, while getting pounded from behind by Ashley. The two new girls were a little shy at first, but feeling their hot little tongues on my cock quickly had me up again. They gave each other a high five and ran off to the sidelines. Alana grabbed my cock and pumped it a few times.
“It’s all ready for you,” she teased Melanie. Melanie was quick to spread her legs across me and sink down onto my cock. Her eyes rolled back and her whole body shuddered as my cock slowly disappeared inside of her pussy. She seemed to be in a state of ecstasy whenever she had my cock and she began to ride me up and down. After letting herself enjoy things for a little bit, Ashley came up from behind her and put her hands on Melanie’s shoulders. Though she continued to ride me, I could see her expression change to a more nervous approach. She felt the strap-on press dangerously against her ass and she slowed down more. Ashley took the opportunity to start to force the strap-on into Melanie’s tight ass.
‘AHHHHHH,’ Melanie screamed. “It’s too much!”
“Ok then,” Ashley said. “Guess you have to stop fucking your man.”
“Ugh, fine,” Melanie said, shutting her eyes as Ashley inserted more of the dildo cock into her ass.
“Just fuck me,” I smiled, wanting to make Melanie feel better. That made her smile and she started to ride me again. While she did this, Ashley was able to get more of the strap-on into her ass and started to time her thrusts with Melanie’s squats. Soon, Melanie was being double penetrated by my cock and the dildo, as her whole body shivered.
“Oh. My. Fucking. Shit” Melanie panted and shouted as pleasure mixed with pain. She almost instantly came, her pussy and ass spasming around the cocks. She fought through it and continued to take the fucking.
“Yeah, take it bitch,” Ashley said, spanking Melanie’s ass. “You like having two cocks filling you up, don’t you?”
As Ashley teased her, I reached up and played with Melanie’s breasts, pinching her nipples and squeezing their fullness. She couldn’t open her eyes and her skin was covered in goose bumps. Just when it looked like she couldn’t take it anymore, Melanie bent down and started to kiss me. She forced her tongue into my mouth and I let it wrestle with mine. Every half a second I could feel her breath heavily and moan into the kiss. When she started to feel my cock growing inside of her, she managed to open her eyes and shot me one of the most seductive looks I had ever seen. It actually made me shiver and I came before I thought I would, grabbing onto her breasts for stability as my cock shot extremely quick and thick ropes of cum into Melanie’s tiny pussy. She kissed me heavily, nearly hyperventilating as she watched me cum inside of her. Mercifully, Ashley stopped and pulled out, letting Melanie fully enjoy my seed. Finally, she collapsed on top of me, my cock still buried completely inside of her as our bodies embraced.
“Wow, looks like you’ve got some competition Hailey,” Alana laughed. “That girl fucking loves that cock.”
Hailey could only laugh and grin, knowing how many times she had fucked me. Outside of her sister, she was the only one who had regular access to me. That was good enough for her and she was happy to share me with her friends. I had to admit, there was an extra attraction that I was developing for both Hailey and Melanie, but that was probably due to sexual encounters we had experienced.
“Hey guys,” Ashley started and turned towards me. “You haven’t stopped staring at Nicki’s tits all night. I doubt she would mind a nice titty fuck with a nice cock like yours.”
Nicki blushed but nodded. Her look seemed to indicate she may have never tried one before, but in the company of her cheer squad, she wasn’t going to disappoint. This time, it was Alana who went to work getting me hard again, looking me straight in the eyes as she rubbed my shaft all over. She offered up her chest to help, and I sucked on her large, perky breasts, paying extra attention to her nipples. Alana rubbed down to my balls and ran her finger up my growing shaft as it reached its full peak again.
The other girls helped to lay Nicki down in front of me. Nicki gave me a seductive look and pushed her breasts together. I eagerly climbed on top of her and felt her soft hands guide my cock between her breasts. Both her and Alana had very impressive racks for their ages, and I was happy to reap the benefits. She closed her breasts around my cock and I started to thrust back and forth, using the ground as leverage. As I did this, Maddie climbed between Nicki’s legs and shoved her tongue into Nick’s pussy, lapping at her clit before thrusting it inside. Nicki started to moan loudly and used her tongue to flick the tip of my cock.
“Now that is a love triangle,” Alana laughed. “Fuck Twilight.”
Hailey came over and started to feel my muscles, kissing and nibbling on my ear. I felt Hailey’s tongue lapping at my ear, making me shiver as I continued my assault on Nicki’s breasts.
All of a sudden, Maddie stopped licking Nicki’s clit and appeared in front of me. Her ripped, toned body was just a few inches from me and she dropped her pussy onto my face. I did my best to pay special attention to her clit, while still being able to thrust through Nicki’s breasts.
“I can’t stand it anymore, just fuck me!” surprisingly, it was Maddie who said this, not Nicki. “Pick me up and have your way with me!”
As much fun as I was having with Nicki, it wasn’t in me to disappoint a girl in need. I quickly regained my feet and easily picked up Maddie off the ground. I wrapped my arms around her tight body and soon dropped her tight pussy onto my cock. She let out a scream as I impaled her over and over, watching her abs contract in a quick orgasm. There was something about tossing a little cheerleader around that had me extra excited and I went in to kiss Maddie’s neck, which was already thrown back in ecstasy.
“Fuck this cock is the best,” Maddie said.
“We told you,” Ashley laughed.
Hailey pulled Maddie’s face back to her and started to make out with her teammate.
“I want to feel you moan into my mouth from the pleasure that cock is giving you,” Hailey said between kisses. She grabbed Maddie’s smaller but perky breasts and rolled her nipples as I continued to fuck her hard in the air.
“Look at him getting bigger!” Nicki cheered. “That vein is throbbing!”
“Looks like you’re about to get filled up little Maddie,” Alana teased as Hailey kissed her extra hard.
“Make sure to fill that pussy up!” Ashley said. “Don’t let a single drop miss.”
“Fill her! Fill her! Fill her!” all the girls cheered as Maddie writhed in my arms in pleasure.
I held back a few extra seconds to let my cock get rock hard and build up cum. Finally, I let loose with a grunt and felt my cock spill hot rope after hot rope of cum deep into Maddie’s tight pussy. She muffled a scream into Hailey’s mouth, who was rubbing her own clit. I dropped her pussy as deep onto my rod as possible, letting her take all of my cum against her cervix.