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Jack In The Box Ch. 5

"Pool Party Celebration"

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After the track meet ended, all the school athletes returned to the hotel. Everyone gathered at the pool, except for the teens from the closer schools who had departed already.

The pool deck wasn't as crowded as last night, and the mood was jubilant. Jack was the hero of the night, and more than one girl came onto him, offering an opportunity to fuck them; Jack never said no, but he never said yes.

Coach Buchanan and Coach Moore sat at a table enjoying the success of the track meet and were relieved the season was over. Kit had her one-piece swimsuit on, and Jack noticed Bruce couldn't seem to keep his eyes off her deep cleavage and hard nipples.

Kit kept looking at her watch, and Jack wasn't sure why. When he heard more than one person say fuck, he looked to see what the commotion was.

Sylvia floated into the pool area wearing her coach's white two-piece bikini. She looked stunning! Kit's suit fit her perfectly, and her smallish tits seemed much more prominent. Sylvia had the transparent cover-up on, and it highlighted how little of her body the suit covered.

Sylvia strutted over to him with a runway demeanor and took off her cover, setting it on the back of his chair. When she turned, Jack saw she had the thong firmly seated between her ass cheeks. He knew every drooling guy had a hard cock.

"What do you think, Jack?" she teased, "Kit, let me borrow it."

There was so much Jack wanted to say, but with all his classmates surrounding him, he would have to mind his words. "I think you're the most beautiful woman here!"

Sylvia blushed deeply, and even though her new boyfriend, Logan, was right beside Jack, she never looked at Logan once.

"Should we go for a dip?" Sylvia asked Jack. "I don't think I can dive in, or I may come up naked!" she laughed.

Jack rose from his chair. There was no way he could hide his hard cock, so he didn't even bother to try. Several of the girls pointed and laughed, but he didn't care. Sylvia held his hand as they walked to the pool steps and descended into the warm water.

"Not too deep," Jack said, "I want to admire your tits."

Sylvia basked in Jack's attention; the moment was perfect, just like Coach Kit promised it would be. Sylvia hesitated when Kit suggested she wear the small suit, but the reaction she received from Jack had been worth exposing her body to all her friends.

The hair around her pussy needed attention, and Kit volunteered to shave her. The sensation of another girl, woman, touching her there had been so erotic. When it was all done, Kit kissed her bare pussy and licked her clit. There wasn't time to do much more, but Kit promised both she and Jack would be spending time between her legs.

"Do you think Logan is jealous?" Sylvia asked.

Jack knew Logan was, but he also didn't care. Sylvia was the prize. Still, he needed to keep up appearances. "Logan, get your ass in here!" Jack yelled, "your girlfriend needs you!"

Logan had been pouting on the chair, watching Sylvia and Jack flirt in the pool. With a smile on his face and a running leap, he jumped into the pool, splashing everyone within ten feet of his entrance. As soon as he reached Sylvia, he put his arm around her shoulder and kissed her forehead.

"I'm the luckiest guy here!" Logan bragged.

"You are!" Jack confirmed, "and we are all lucky Sylvia is brave enough to wear such a tiny suit!"

Coach Buchanan was confused, he thought Jack and Logan were lovers, but now it looked like Sylvia was Logan's girlfriend.

"She's stunning!" Kit said, "I don't think I could ever wear such a tiny suit. I mean, really, with tits like mine!"

Bruce couldn't believe his ears; Kit just commented on her breasts or tits as she called them. "You have a great figure!" Bruce stuttered, "a real woman's body!"

It was right at that moment that the pizzas arrived. Kit ordered a dozen to feed everyone, with a mixed variety of toppings.

The rush to eat spurred all the students; Logan hustled out of the pool, leaving Sylvia behind.

"Looks like food is more important to Logan than you," Jack said. "Did you and Logan clean your asses for tonight's big event?"

The memory made Sylvia smile, "Oh Jack, you should have seen him!" she exclaimed! "At first, he was like a baby, but then he was embarrassed that he liked it! It was so funny to see the change; even his cock got hard!"

Jack laughed, "who knew! I guess I should have kept fucking his ass!"

Sylvia looked at Jack with a smile in her eyes. "You still could," she laughed, "tonight when we get together. He has a big bromance on you! I think he would welcome it!"

"I love you more and more!" Jack laughed, "by the way, I can't get out of the pool. You have my cock so hard it's hurting!"

"Let's go over to the side," Sylvia smiled, "I'll give you a hand job."

"Kit said she shaved and played with your cunt. Did you like it?" he asked.

"It felt funny for another girl to touch me, but it turned me on!"

The two of them moved to the side of the pool out of the rest of the group's view.

"Kit and I have a surprise for Logan. Do you want to be in on it?" Jack asked.

Sylvia had no idea where Logan was. He abandoned her; she was supposed to be his girlfriend. "Does it entail humiliating him?"

"Well, now that you mention it," Jack smirked.

The two of them talked about the plan as Sylvia stroked Jack's cock.

Sylvia put her hand over her mouth in surprise. "Oh my god! Do you think he will do it?"

"If you play your part, he will. Logan won't have a choice."

"Let's do it!" she said and kissed Jack on the lips in excitement.

"Hey! What was that for!" asked Logan as he returned to the pool, catching them kissing.

"I was just congratulating Jack on his impressive race today!" Sylvia said with a false smile. "You didn't bring me any pizza? Never mind, I will get my own!"

"I think I just fucked up," Logan said, "she seems mad."

Jack looked at Logan, "Well, if the hottest girl in school was my girlfriend and everyone knew it, I can't think of anything I wouldn't do to keep her." Jack hesitated. "I mean, look at all the guys surrounding her to get a look at her tits and ass! She is fucking hot!"

"I know! I'm the luckiest guy in school!" Logan said as he turned to leave, "I'm going to go make sure no touches her."

So far, so good, Jack laughed as he adjusted his cock before getting out of the pool.

Jack saw Kit and Bruce taking and walked over to them. He had adjusted his swimsuit up, so his cock was hanging out the bottom. Most of his fellow students were too busy to notice, but Coach Buchanan's eyes were bulging out.

"Jack!" Kit called out, "I saved you a slice. Come and sit down beside me!"

Jack sat opposite Bruce, and Kit could see Jack's cock out the bottom of his shorts. "Oh my!" Kit exclaimed as she looked down.

Bruce knew what had shocked her; it was Jack's cock.

"There's a bug on your pizza. Let me get it!" Kit said. She picked off the imaginary bug and pretended she held it in her fingers, unsure what she should do with it.

"Go ahead and wipe it on my suit," Jack said, "I don't mind."

Bruce watched Kit's hand go under the table and waited for her scream, but it never came. Instead, she moved her chair closer to Jack and kept talking like nothing was wrong. Her hand never came back out, but she kept moving her arm back and forth. He wasn't sure if she was getting rid of the bug or rubbing Jack's cock.

"Oh god!" Jack suddenly said with a shake of his body, "that was unexpected!"

Kit looked at Bruce and drew her hand out. "Looks like I have a little sauce on my fingers," she smiled at Bruce as she licked her fingers and then sucked them clean.

Bruce couldn't believe what just happened or didn't happen; he was losing his mind. Did Kit give Jack a handjob and lick his cum off her fingers?

Jack looked at Kit, "Sylvia looks amazing in your suit!" he said, "almost as good as you!"

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Bruce spit out the soda in his mouth as he stared from Jack to Kit.

"Oh god, Bruce!" Kit said, "you should see your face! Jack and I are playing a trick on you!"

"So, so, you didn't just jerk him off in front of me? And that wasn't his, you know, on your fingers?" Bruce knew the suit couldn't possibly be Kit's; it was much too small

Jack's boisterous laughter attracted the attention of everyone, including Sylvia.

Bruce watched the rest of the kids gather around Sylvia to look at the almost non-existent suit; the top didn't look any bigger than two band-aids to him. 

"Logan, go get me a cock, I mean coke. Oops, my bad!" Sylvia laughed at the kids gathered around her. "All you horny boys have me confused!"

As soon as Logan left, several of the guys moved on Sylvia, nothing physical, but she appreciated all their comments, even if they were rude. "Sorry, guys, I have a boyfriend," she said as she walked straight to Jack, her secret boyfriend.

"Hi Jack, hi Coach Buchanan," she said, "thanks for lending me your suit, Coach Moore. I love it!"

Bruce looked from Kit to Sylvia, "Ah, good one!" he said, "Sylvia is in on the joke!" He didn't want to look at Sylvia, but his eyes were level with her barely covered pussy. He could see the material bunched up, outlining her girly parts.

Sylvia saw her coach checking her out. "Want to see the back?" She spun around to let her coach see her ass close up.

"Fuck, you look incredible!" Bruce whispered, then regretted his words. Sylvia had the tightest well-formed ass. From the back, it looked like she was naked.

No one said anything as they watched Coach Buchanan ogle Sylvia's bare ass.

"Here you go!" Logan said as he burst into the moment, "one coke."

Sylvia turned towards Coach Buchanan again. "Thanks for the compliment!" she smiled seductively. "You don't think the suit is too small, do you?"

Logan watched his coach look at Sylvia's tits and travel down to her cunt. He knew he should be mad, but he was thankful Sylvia wanted to be his girlfriend.

"I think you are perfect," Bruce said with a very red face, "Um, I think I need to go use the bathroom."

"Will you think of me?" Sylvia teased as she pointed to his crotch. "When you, you know!" Sylvia made a motion for jacking off as she looked at the erection in his coach's swimsuit.

Bruce looked around, and all the kids were staring at him. He grabbed a towel to cover his crotch and almost ran to the hotel door. The sound of their laughter rang in his ears.

Jack pulled Sylvia over, and she sat across his knees with her cunt pointed to Kit. Logan took his coach's chair.

"That was fun," Sylvia laughed.

Kit looked over at Logan. "Sweetie, would you mind getting me a drink? Jack, would you like one too?"

Logan watched Jack with his arm around Sylvia rubbing her back; then he watched him drop his arm down to her ass. When Sylvia jumped, he knew Jack had just touched her ass or cunt.

Sylvia took a sip of her coke and let out a big sigh. "Hmm, that feels nice," she said as she looked at Logan and squirmed on Jack's lap. "Well, don't just sit there, Logan! Go get two more drinks!" she snapped.

Logan jumped and almost ran for the drinks; he didn't want Sylvia to be mad at him.

Lana, one of the students in their school, came over to the table. She nervously looked at Kit and smiled.

"Um, Coach, would it be alright if some of us paired off and went back to our rooms?"

Kit knew what Lana meant, but she wanted her student to confirm it. "Who are you going to fuck?"

"I was hoping Jack, but I can see Sylvia has him, so it will probably be Greg," Lana said, jealous of the attention Sylvia was receiving in the tiny bikini.

"Do you have condoms?" Kit asked.

"Yeah." she answered, "everyone does."

Kit looked at Lana, "Jack says you like to fuck guys up the ass with a strap-on dildo. Is that true?"

"Um, yes," Lana said in total embarrassment.

"Good for you! Sometimes a woman needs to take control," Kit smiled. "Okay, tell the kids they can pair off if they want, but no sex without a condom. Got it!"

"Fuck, you're the best!" Lana gushed. "Thanks, Coach!"

Jack watched the news spread through the crowd of kids, and 'high-fives' were everywhere. It didn't take long before there were only a few kids were left milling around.

"Where's everyone going?" Logan asked as he sat back down with two more drinks.

"To fuck!" laughed Sylvia, "Kit said they could."

"Speaking of fucking, maybe we should head inside too," Kit said. "Staring at Sylvia's cunt is making me hungry!"

Kit fixed Logan with a hard stare, "Did you clean your ass, Logan?"

Logan looked around, all embarrassed, making sure no one could hear them. "Yes, Sylvia did it to me."

Sylvia laughed out loud, "the third time was because he liked me playing with his ass! His cock was hard as a rock!"

"Well, well," said Jack with a straight face, "that's interesting news."

"It's okay, Logan," Kit whispered to him, "maybe Jack can fuck you for real this time!"

Logan's face was a mix of emotions as he looked across the table. He wanted to be part of this group, but somehow, he felt he wasn't.

"Shall we go then?" Kit said.

"Only after Jack takes his finger out of my ass!" laughed Sylvia.

Jack pulled his finger out and looked at it. There was nothing on it; she had done an excellent job cleaning herself out.

"Okay, which room do we use?" Jack asked.

"Let's use mine," Kit said. "I have two queen beds. Plus, all my toys are there!"

As they walked to the door, Bruce came back out. "Where did everyone go?" he asked.

Kit gave Bruce a nasty stare. "Because you couldn't control your cock all the kids thought they had your approval to fuck each other! I wouldn't do a headcount tonight unless you want to see a lot of naked kids fucking!"

"But I never said that!" he blurted out, "it was an accident."

"Don't worry; I won't say anything to the principal," Kit said as she accidentally rubbed her breast against his arm, going by him.

Logan and Sylvia followed, and Jack stood there. "Sorry, Coach, I told her that's not what you meant. Do you want to join Logan and me later?" Jack said as he winked at his coach. "We have lots of lube."

"What? Fuck no! Get out of my sight, and I don't want to see you until we get on the bus in the morning!" Bruce said, all flustered.

"Your loss," Jack said. In a moment of appreciation, he looked around to see which kids were left on the pool deck, "Alice over there likes to be fucked in the doggy position if you get horny again. She yells a lot, but nothing is off-limits! Alice, come here!" Jack yelled.

Bruce shrank as Alice quickly came running, making her giant tits bounce up and down. "Hi, Jack!"

"Are you hooking up with anyone?"

"Um, not yet. Why?"

"I think you and Coach Bruce would be a good match."

"Really?" Alice gave her coach a little giggle looking down at his crotch. "I saw how big you are! Let's go in the pool so I can check you out!"

Jack smiled as he casually walked to the door where his gang waited. Today had turned out way better than he could have imagined. Alice quickly dragged Coach Bruce to the pool hand in hand, talking non-stop along the way.

Bruce was embarrassed as Alice thrust her hand in his trunks before they got to the pool.

"Yahoo!" Alice shouted. "He does have a big one!"

"Bruce, I hope you can keep up with Alice!" Kit shouted in laughter.

Logan opened the hotel door then trailed behind, wishing he could be as confident as Jack.

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Thank you for taking the time to read my story; if it tickled your fancy, I appreciate your vote and comments.

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