Jack In the Box

"Colleen and I have a surprise for Logan, do you want to be in on it?"

Sylvia had no idea where Logan was, and right now she was pissed that he abandoned her; she was supposed to be his girlfriend. "Does it entail humiliating him?"

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

The two of them talked about the plan, and Sylvia put her hand over her mouth in surprise.

"Oh my god! Do you think he will do it?" she asked.

"If you play your part, he will. He 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 could see Colleen and Bruce still sitting at the same table and walked over to them. He had adjusted his swimsuit, 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!" Colleen called out, "I saved you a slice, come and sit down beside me!"

Jack sat opposite Bruce and Colleen could see Jack's cock out the bottom of his shorts. "Oh my!" Colleen 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!" Colleen 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 Colleen'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!"

Colleen smiled at Bruce and drew her hand out. "Looks like I have a little sauce on them," she smiled at him 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 Colleen give Jack a hand-job and lick his cum off her fingers?

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

Bruce spit out the pop that was in his mouth as he stared from Jack to Colleen.

"Oh god, Bruce!" Colleen 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 finger?" Bruce knew the suit couldn't have been Colleen's it was much too small.

Jack's boisterous laughter attracted the attention of everyone, including Sylvia. "Logan go get me a cock, I mean coke. Oops, my bad!" Sylvia laughed at the kids gathered around her.

As soon as Logan had left several of the guys made a move on her, 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 new boyfriend.

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

Bruce looked from Colleen 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 eye level with her barely covered pussy. He could see the material bunched into her, outlining her female parts.

Sylvia could see her coach checking her out, "the back is just as good!" she said as she spun around to let him see her ass close up.

"Fuck!" Bruce whispered then regretted his words. Sylvia had the tightest little ass, and he couldn't help himself, from the back it looked like she was naked.

No one said anything as they watched Coach Buchanan stare at Sylvia's ass.

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

Sylvia turned and gave Coach Buchanan a big smile, "thanks for the compliment!" she said to him, "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 she wanted to be his girlfriend.

"I think it is 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, "when you, you know!"

Sylvia was right Logan thought as he looked at the erection in his coach's swimsuit.

Bruce looked around, and everyone was smiling at him, even some of the kids who had been listening in. He grabbed a towel to cover his crotch and almost ran to the hotel door. The sound of the laughter rang in his ears, but worse now everyone knew he wanted to fuck one of his students. As he ran his thoughts were this had turned into a very bizarre weekend.

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

"That was fun," Sylvia said.

Colleen 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, "hmm that feels nice," she said as she looked at Logan and squirmed on Jack's lap. "Well don't just sit there! Go get two more drinks!"

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

Lana, one of Coach Coffin's girls, came over, she looked at Colleen and smiled. "Um coach, would it be alright if some of us paired off and went back to our rooms?"

Colleen 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 with a big smile at Jack.

"Do you have condoms?" Colleen asked.

"Only a couple." she answered, "but I think there are enough to go around."

Colleen looked at Lana, "Jack says you like it up the ass. Is that true?"

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

"Good for you!" Colleen 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!"

They watched the news spread through the crowd of kids, and 'high-fives' were everywhere. It didn't take long before 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, "Colleen said they could."

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

Colleen fixed Logan with a 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 three times."

Sylvia laughed out loud, "the third time was because he liked having something in 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," Colleen whispered to him, "my tongue is going to make you very happy then!"

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

"Shall we go then?" Colleen 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 a good job cleaning herself out.

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

"Let's use mine," Colleen 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.

Colleen 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 head count tonight unless you want to see a lot of naked kids fucking!"

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

"I'm not going to say anything to the principal, this time!" Colleen said as she stormed 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 I later?" Jack said as he winked at his coach.

"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.

"Good night coach," Jack said as he looked at which kids were left on the pool deck, "if you change your mind Alice over there likes to be fucked in the doggy position. She yells a lot and comes like a real slut!"

Jack smiled as he nonchalantly walked to the door where his gang waited, this had turned out way better than he could have imagined.

Bruce watched in shock as Jack said a few words to them and they all looked at him and laughed.

"Good luck!" Colleen yelled before opening the door and heading in.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

After Pool Party

The four of them rode up the elevator, and Jack took turns kissing Colleen then Sylvia while Logan looked on a little crestfallen.

"Don't worry Logan you'll get your chance later," Colleen said to him.

Logan hoped she meant with the girls, but the look in her eyes made him uncertain. Jack was a good looking guy, but he had never thought about him that way.

As soon as the elevator stopped Jack put his arm around his teacher and walked her down the hallway towards her room. Lana was coming out of one room, and Jack could tell by her hair and half-exposed tit in her swimsuit that she had just been fucked.

"Finished with Greg already?" Jack asked. "Let me fix your top," he said as his fingers reached out and fully exposed both of her tits before pinching her nipples.

Lana's head quickly swiveled to her coach in panic.

"It's okay Lana," Colleen said, "did Greg fuck your ass?"

Lana stood in front of her teacher with her tits exposed and Jack pinching her nipples. "Um, yes he did." she answered all flustered, "but he came too quickly, and said he was too tired to do it again so I was going to see if I could find another guy."

Jack leaned down and sucked on her nipple. Lana was in shock her teacher would condone this.

"I tell you what, how about if we lend you, Logan?" Colleen said, "you can take him back to your room and make him do anything you want. And I do mean anything!" she laughed. "Do you have any toys?"

"Um, I did bring a couple, yes," Lana said hesitantly.

"Great! Logan like things in his ass too!" Colleen said.

"Really! This could be lots of fun!" Lana enthused, "thank you so much!"

Jack gave her nipple one last suck and held Lana's chin with his fingers, "I owe you this," he said as he kissed her passionately, slipping his tongue in her mouth, letting her suck on it.

Lana was in shock; Jack never kissed any of his 'girls.' "Wow!" she said, "I like the new Jack!"

"If Logan gives you any trouble, we will be in Coach Coffin's room, just give me a call," Jack said as he gave her one more quick kiss.

Jack never even looked at Logan as he put one arm around each girl and headed to Colleen's room, they could hear the conversation echo down the hallway.

"So, you like things in your ass! That makes two of us!" Lana laughed, "we are going to have so much fun boy-toy! Have you ever had your tongue in a girl's ass?"

Sylvia chuckled at that, Lana was going to teach Logan all kinds of new things tonight. Plus, she knew Colleen and Jack were going to be teaching her.

Colleen opened her door, and Jack scooped Sylvia up in his arms and carried her over the threshold. "Tonight you are going to be our bride," Jack said, "our blushing bride who gives her body to us."

Sylvia rested her head on Jack's shoulder as he carried her into the room. She felt like a bride, and the butterflies in her stomach were flying high. She heard the sound of the door closing and knew her training started right now.

"Anything Jack," Sylvia said as she kissed his neck, "I will do whatever you and Colleen want me to."

Colleen pushed aside the swimsuit, and her finger found a wet and willing cunt. "Hmm, I can't wait to suck your cunt," she said as her fingers went deeper, "your tight young cunt!"

Jack and Sylvia were in a deep kiss when he felt Colleen lower his swimsuit and her hand found his hard cock. Her lips were soft as they touched him, licking first, then sucking him whole.

"Hmm, I love your big cock," Colleen murmured, "let's get on the bed."

Jack lowered Sylvia, then held her shoulders and looked into her eyes, "we are going to teach you so much! How to please a man, how to please a woman, how to enjoy pain."

Sylvia's eyes lit up at that comment; she wasn't expecting pain.

"Don't worry Colleen will show you, she loves to be spanked and used hard," Jack said softly, "now let's get you naked."

Jack walked over to close the drapes and looking down he saw Alice and Coach Buchanan talking. They were both laughing at something and coach had his hand on her back, just above her young ass. Jack smiled and wished him good luck in fucking her.

Turning Jack saw both of his girls were naked and waiting for him. "How do you want us?" Colleen asked.

"On your knees."

Sylvia watched his cock approach and knew what he wanted. She opened her mouth wide hoping she would be first, but he chose Colleen. She watched his long cock go deeper and deeper each time Colleen moaned. Then it was her turn. Jack didn't force himself he just pushed, and she let him go as deep as he wanted.

"Good girl," Colleen said, "open your throat up and let Jack in."

Colleen looked up at Jack, her handsome Jack, "I love you, Jack!" Colleen said with a heart full of emotion.

"I love you too," he smiled, "move behind Sylvia, play with her tits."

Sylvia felt Colleen's large breast touch her back; she lifted her arms and Colleen's circled her body finding her tits. Sandwiched between them, her hands found Jack's legs and pulled him towards her trying to get his cock deeper into her throat.

"No, honey," Colleen said as she pinched down on Sylvia's nipples, "Jack is in control, let him use your mouth. Your body is his now, just like mine is. We are here to please him."

Colleen's body anchored Sylvia's, and with each push of his cock, Sylvia had nowhere to retreat. He was close now; he could feel his cock almost entering her throat but not quite.

"This is it, Sylvia, now is the time to prove you meant every word you said, that I could do anything to you," Jack said, "the next time I push it will be deeper, and into your throat."

When Jack pushed, he could feel the difference. "Good girl," Jack praised, "I'm going to do it again."

Sylvia was proud of herself; Colleen was pinching her nipples harder each time Jack went deeper. Each push now was into her throat.

"Put your hands over mine," Colleen whispered, "feel the pain, feel it go all the way to your cunt."

She did feel the pain and realized it felt good. Each time Colleen squeezed her nipples she would squeeze right along with her.

"Yes," Colleen whispered, "now I want you to pinch your nipples, and I will hold your hands."

"Look at me Sylvia," Jack said, "look at me as you hurt your tits."

Jack watched Sylvia as he pushed a little deeper, her fingers were pinching, and tears were forming in her eyes. "Harder, sweetheart, pinch harder!" he said.

Sylvia didn't want to disappoint Jack, and she twisted and pulled her nipples as hard as she could. She felt Colleen reach between her legs and pinch her clit at the same time. She loved the smile on Jack's face, and with her head tilted up he was finally able to get all his cock in. Her nose was pressed against his body as he held his cock in her throat. Watching her with those sexy brown eyes of his, testing her.

"Just a little longer," Colleen whispered in her ear, "now hurt your tits again!"

The pain was incredible, but she wouldn't quit, not with Jack and Colleen watching. Just when she thought she would pass out, Jack pulled out and dropped to his knees, looking into her eyes as she gathered her breath. She was still pulling and pinching on her nipples, and Jack placed his hands over hers to stop her. Jack kissed her tenderly, and Colleen was kissing her neck.

"You were incredible!" Jack said, "don't you think Colleen?"

"Yes," Colleen enthused, "I think she was fantastic!"

Sylvia basked in their praise, yearned for it, she didn't want to disappoint either of them.

"Okay no more pain for now," Jack said before he gave Sylvia a quick kiss. "Let's go on the bed; I think Colleen is dying to taste your freshly shaved cunt."

"And you can taste mine at the same time," Colleen said into Sylvia's ear.

The bed gave a slight creak as they got on, the girls waited for Jack.

Jack sat on the edge of the bed, Colleen had her arm around Sylvia's shoulders, and he loved the excited smile on both of their faces. "I want you to spend some time getting to know each other, what you both like and what turns you on." Jack couldn't believe he was about to turn down sex with them. "I will be back in a while, but before I go, I want to watch you. Colleen you get on the bottom and Sylvia on top, I want you to please each other with your mouths," Jack said.

The girls did as he asked and Colleen couldn't wait as mouth attacked Sylvia's pussy. Jack waited until Sylvia did the same. There was no hesitation in either girl, and that pleased him. With one last look back neither girl heard him leave the room, they concentrated on pleasing each other.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Shonda

Jack wandered out to the pool deck, all the lights were off, and the pool officially closed for the night. The deck lounge chairs looked inviting, and he headed that way.

"Hey!" said a voice in the dark, just before he sat down on someone.

"Fuck!" You scared me. Is that you Shonda?"

"Yes. Is that you Jaquime?" she laughed, "It's kind of hard to see us in the dark, "

"Wow, I haven't been called that since elementary school," Jack said. He remembered back to when his mom had changed it to Jack; she said it was more American and less Dominican."

Jack sat in the chair beside Shonda, and she was right, with their mutual dark skin it was hard to see them in the dark, especially with the overcast clouds and no moonlight it made them virtually invisible.

"You did good today Jaquime; your dad will be proud of you; even your mom."

"They're getting divorced," he said.

"I know, your mom is just waiting until you finish school."

"You talk to my mom a lot, don't you?"

"Yes," she said, "is that why you avoid me?"

"Maybe." Jack knew Shonda worked part-time with his mom at the travel agency. Her mom had secured her the job.

The silence between them grew, and Jack found it interesting that it wasn't uncomfortable. He had known Shonda for a long time. At one point their families used to be close. Before his mom started fucking around on his dad.