Jack In the Box

The awkwardness of two naked and two clothed passed when Colleen tugged on Logan's cock. Not to be outdone Jack pushed his fingers up Sylvia's cunt.

"You know we're going to fucking both of you again don't you?" Colleen said as she looked from Logan to Sylvia. "Jack and I talked about it last night."

"We were hoping so!" Logan said, "we talked too and wanted to do it again."

Jack leaned into Sylvia and kissed her complete with tongue, and he felt her cunt get wet. The look of surprise at being kissed by Jack said it all. "Also, tonight you're going to have a cock in your cunt and one in your ass at the same time," Jack said to her as his fingers pushed deeper.

"Oh god! Yes! I want to do that!" Sylvia exclaimed as she squirmed on Jack's fingers.

Colleen knelt down and gave Logan's cock a quick suck. "Hmm, I taste Sylvia on you," she said. Colleen stood up and looked at Sylvia, "and tonight your mouth is going to suck my cunt until I come all over your face," she said as she forced a finger in her mouth. "This sweet little mouth is going to please me."

"Fuck!" Logan exclaimed, "that's so hot!"

Colleen and Jack fucked Sylvia as she stood there in shock. When Colleen finally pulled her finger out, she kissed Sylvia fully on the lips. The kiss was gentle and sexy. "Hmm, I might have to suck your cunt too. Would you like that?"

Sylvia was so turned on she would have fucked them all right now. "I can't wait!" she said.

Jack pulled his fingers out of Sylvia's cunt and rubbed her lips, "open up and taste yourself."

Colleen knew this was going to be an interesting arrangement. Jack and she were very alike, and they planned on taking advantage of the naivete of these two.

"We need to get going," Colleen said, "Jack and I will meet you downstairs for breakfast."

"Okay," Jack agreed, "Logan you are one lucky guy to have such a sexy girlfriend!"

"I know!" he responded.

Jack and Colleen left the room and walked to the stairwell, "that went well I think," Jack said. "Good move going first with Logan's cock. It made him feel like he was in control."

"Do you think they will do all the things we want them to?" Colleen asked.

"One hundred percent!" Jack enthused, "Logan and Sylvia are going to be our sex toys."

"Even Logan?"

"He was going to bend over for me last night," Jack laughed, "I know he will do what I say."

"My cunt is dripping just thinking about it!"

"You say the sweetest things to me!" Jack laughed.

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Race Day

The breakfast room was overflowing with teenagers and coaches. Colleen spotted Bruce and went over to him as Jack got in line for some carbs.

"Bruce I am so sorry!" Colleen said as she got right into his personal space, "I feel like a bitch for abandoning you!"

When Colleen touched his arm he forgot all about her breach, "It was a little hectic, but I managed."

"You've been working out!" Colleen gushed as she squeezed his muscle.

Jack laughed as Bruce pumped out his chest to something Colleen said to him.

"I rode down in the elevator with Jack; he said Logan is a little sore this morning and to ask you about it. Did something happen to Logan? I hope it won't affect his race."

Bruce turned a little white as he avoided Colleen's eyes. Unfortunately, he looked right at Jack who waved at him. "Um, no I don't know what Jack is talking about. I checked on them last night, and everything was normal."

"That's strange? Oh well, I hope the team does well today! See you on the bus."

Bruce watched Colleen walk away with a sexy wiggle and once more thought how good it would be to fuck her. Jack was no longer looking his way, and he considered himself lucky that Jack didn't reveal more to Colleen.

The noise in the room was over the top, but for Colleen, it seemed dead quite, her thoughts were on Jack. He had brought her so much pleasure it was unbelievable. Their new collaboration was exciting to think about, and like he said once they were tired of Logan and Sylvia, each year she would have access to new students, and he would have the same at college.

Once breakfast was over all the kids went out to their respective buses for the short drive to the stadium. Team colors blazoned across the chests of all the athletes and coaches. The sky was overcast, perfect for track events and the humidity was low.

Jack sat in the stands cheering his teammates on at each event; his race was the second last one of the day. Coach Buchanan had mentioned to him that two of the big colleges had scouts were in the stand, and he had passed on his praise of him to them. Jack thanked him, and Coach Buchanan awkwardly walked away after Jack hugged him.

Logan did well in the high jump, coming in the top five. He watched Sylvia in the relay and laughed as her form seemed a little off. He was sure her ass was killing her.

He was stretching when Colleen came over. "Keep an eye on the guy in blue; I heard he likes to elbow competitors to get by."

"I don't care about winning," Jack said, "I've decided I am going to accept the scholarship to the local college."

"Look, I am glad you are staying in town, but don't you ever fucking tell me you don't care if you win or not! I wouldn't be alive today if I gave up on myself!" Colleen burst out. "I believe in you and you better fucking well do the same!"

Jack was in shock as he watched Colleen storm away. He forgot this was her second passion, and she was very competitive, but it was the part about not being alive that got to him.

The race was underway and like always he hung back until around the middle. He liked to gauge his competitors, read their body language, look for any weaknesses in their stride. Colleen was right about the kid in blue; he liked to bully his way forward and try to intimidate his opponents.

Jack easily moved up through the group until he was beside him. "Hey! Nice day for a stroll!" Jack said as he looked over. "How about you and me make a race of this?"

"Fuck off!"

"No really! Catch me if you can!"

Jack knew it was too early to go for a finishing kick but the guy was so arrogant it would be worth it to see him collapse. Plus, he knew this guy's ego wouldn't let him get too far ahead. Jack took the first position and kept an eye out for the blue guy. When he got, close Jack would increase his lead. He could hear his competitor's breathing; it was forced and labored. Every time the guy got close. Jack would kick it up a notch and stay ahead of him.

Jack looked back, "is that all you got!" he yelled.

Jack's strategy worked, the insult threw his competitor off balance and had him questioning his abilities. Jack's lungs were bursting as he barely stayed ahead. The last turn was coming, and this would decide the whole race. He thought of how pissed off Colleen was with him, and that thought was all he needed. This race was for her. He didn't know where the extra energy came from but his lungs stopped hurting, and his legs felt lighter than they ever had. Jack won the race, and the guy in blue came in a distant second. All his teammates surrounded him, yelling and cheering, helping him to stay vertical. They told him he had set a new state record.

Coach Buchanan was bursting at the seams with pride as he kept clapping him on the back, but it was Colleen he wanted to impress. He saw the huge smile on her face, and the tears falling down her cheeks and knew it had all been worth it.

He watched Colleen come over to him, "you need to keep moving," she said, "to get rid of the lactic acid."

Jack had his arm over her shoulder as she forced him to walk beside her, she handed him an energy drink, and he drank most of it with the rest drooling down the front of his shirt.

"They're still cheering for you," Colleen said with a big smile, "I have never seen anything so amazing!"

They turned around, and he let her guide him, Jack could see the guy in blue limping his way. When they got close, Colleen stopped them.

The guy was holding out his hand to Jack. "I don't know how you did, but that was the best race of my life! I set a new personal best time!"

He shook Jack's hand and walked away with a very pronounced limp.

"He didn't say congratulations," Jack said, "what an asshole!"

"I agree," Colleen said, "now keep walking I need to go talk to Bruce."

Logan and Sylvia were by his side now, and his breathing was returning to normal. He could feel his heart rate receding as they walked side by side. He could see also see they were both just as proud of him as Colleen.

Sylvia looked to see if anyone was within listening distance. "My ass is yours tonight Jack, that's your reward for doing so well," she said with a big smile on her face.

Jack noticed she didn't look for Logan's approval and Logan didn't seem to mind her offer to him. "In that case, you better clean it good because you're going to be sucking it clean after."

"I will Jack, I promise!"

"You too Logan," Jack said as he looked at his friend.

Logan was at a loss for words and just stared open-mouthed at Jack.

"Colleen wants to lick your ass tonight," Jack concluded.

"Fuck!" Logan said as he relaxed, "Thanks Jack I will!"

"Logan go see the trainer, tell him you have a bowel problem, and he will give you an enema kit. I want you to clean each other at least twice," Jack said, "and if you enjoy it you can do it as many times as you want," he laughed. "Oh, tell him you need a tube of lube too."

Jack could see Logan was hesitating, "this is our last night in the hotel, I want to make it special for everyone." Jack thought for a minute, "and if you want to have some fun tell the trainer Coach, Buchanan suggested you needed the enema."

They all laughed at the recollection of last nights episode with the coach.

"Okay take off Logan I need to talk to Sylvia."

"Congrats again bro!" Logan said as he clapped his friend on the back, "you were fucking amazing out there."

Sylvia and Jack watched Logan as he headed to the trainer's area. Jack noticed she didn't give him as much attention as he thought she should.

"I'm sorry Jack," Sylvia started, "I should have let you fucked my ass a long time ago. Maybe we would be together now."

"Maybe," Jack said, "but at least we have this time together."

"After that race, you're going to be getting scholarships from all the big colleges."

"Maybe, but I might just stay local."

"You like her don't you? Coach Coffin."

"Yes, but that's not what I want to talk to you about."

Jack guided Sylvia over to the sidelines, and they sat in a secluded area. He examined her face and posture for clues to her emotions.

"You're a beautiful woman, everything about you is perfect, both Colleen and I think that." Jack let Sylvia bask in his praise for a minute. "I can't let you go! We can't let you go!"

"I don't understand?" she said.

"After this weekend is over I want to keep fucking your beautiful body. I want to make love to you, kiss you, make you come a thousand times." Jack could see the hope and excitement build in her eyes. "And I want to include Colleen with us."

Jack knew this could go two ways; an acceptance of his proposal or she would bring up Logan, her new boyfriend.

"You both want me?"

It was going the way he hoped it would. "You have no idea how sexy you are, do you?" The compliment was showing in Sylvia's reddening face. "Your tight body and willingness to try new things; even offering me your ass after the race. You're becoming a real woman now. I'm so proud of you!"

Jack could see his words were settling in and he waited for her answer.

"I, I like Coach Coffin, Colleen, and you know I love you, right?

When Jack nodded his head, Sylvia continued.

"You both know so much about sex, will you teach me?"

"Yes! Yes!" Jack shouted as Sylvia tried to shush him, looking around totally embarrassed by him.

Jack pulled Sylvia to her feet and lifted her up swinging her around in a circle as she laughed at his antics. As soon as her feet hit the ground, he saw Coach Buchanan and two older guys coming their way.

"Oh, oh here comes the warden," Jack said as used his chin to point at the approaching group. "I'll see you later okay?" Jack said with a big smile, "and thank you for saying yes; I will keep you satisfied, I promise!" he laughed.

Jack watched the swagger in her walk as she waved at Coach Buchanan when they passed each other. Colleen had been right, Sylvia was more interested in him than Logan.

"Jack!" Coach Buchanan called out, "these gentlemen want to talk to you about your amazing race!"

For the next half hour, Jack listened to both men talk about recruiting him to their college. One was the head of the sports division, and the other was the coach. It was interesting to see them use the same tactics he had just used on Sylvia. The difference was he knew what they were trying to do. At the end of it all, they shook hands, and Jack promised he would get back to them next week.

After the scouts left Jack turned to his coach. "What do you think?" Jack asked.

Coach Buchanan knew Jack was special, he had always known that, but for some reason, he could never get Jack to the next level. That's why he brought in Coach Coffin. It looks like he made the right decision.

"A full ride is hard to turn down," he said, "I know it's not the college you were hoping for, but they do have a great sports program.

"Yeah, but they're known for basketball and football," Jack countered. "I wonder if I hadn't set a state record whether they would have been as interested in me?"

"Hard to tell son," he said, "but at least you have two choices now."

"Yeah thanks, coach, "Jack said. As soon as his coach stood up, Jack laid the other news on him. "I hope you don't mind, but I sent Logan to the trainers to get an enema kit, it was a little messy last night. I told Logan to say you approved it."

Bruce stood there with his mouth open; Jack had implicated him in a homosexual act.

"Don't worry; I told Logan to say it was for an upset bowel," Jack said as he winked at his coach. "Anyway, I need to go find Coach Coffin and thank her for the pep talk she gave me before the race. It was her words that gave me the last kick in the race."

Jack left his coach behind to contemplate how he was going to spin this if word got out he condoned his male athletes could have sex together.

Jack never did find Colleen until they boarded the bus so he couldn't share the good news with her. He winked as he passed her going up the aisle. All the kids shouted out his name and clapped as he walked to the back of the bus. It felt good to be him at this moment.

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

Pool Party

Tonight was the last night at the hotel, and everyone had gathered at the pool. Some of the kids from the closer schools had departed already, so the pool deck wasn't as crowded as last night. The mood was jubilant, and Jack was the hero of the night. More than one girl came onto him hoping to get him to fuck them tonight; he never said no, but he never said yes.

Coach Buchanan and Coach Coffin sat at a table enjoying the celebration and good mood. Colleen had her one-piece swimsuit on, and Jack noticed Bruce couldn't seem to keep his eyes off her deep cleavage. Colleen 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 came into the pool area wearing Colleen's white two-piece bikini. She was stunning! The suit fit her perfectly, and her smallish tits seemed much bigger. She had the transparent cover-up on, and it highlighted how little of her body the suit covered. Sylvia came right over to him and took off her cover setting it on the back of his chair. When she turned Jack saw she had the material bunched into her ass like a thong. He knew every guy her was getting hard because he was.

"What do you think Jack?" she teased, "Colleen 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 in the room."

Sylvia blushed deeply, and he noticed even though Logan was right beside him she never looked at him once.

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

Jack rose from his chair, and 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 looked at Jack; the moment was perfect just like Colleen promised it would be. She had hesitated when Colleen suggested wearing such a 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 to shaving and Colleen volunteered to remove it. The sensation of another girl, woman, touching her there had been so erotic. When it was all done, Colleen had kissed her right on her pussy and licked her clit. There wasn't time to do much more, but she promised both her and Jack would be spending time between her legs.

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

Jack knew he was, but he also didn't care. Sylvia was the prize not him. 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, Sylvia was his girlfriend, and now thanks to Jack everyone knew it. 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 has the guts to wear such a tiny suit!"

Coach Buchanan was confused, he thought Jack and Logan were having sex, but now it looked like Sylvia was Logan's girlfriend. He watched the rest of the kids gather round Sylvia to get a look at how small her suit was; the top didn't look any bigger than two band-aids to him.

"She's stunning!" Colleen 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; Colleen just commented on her breasts or tits as she called them. "You have a great figure!" Bruce said, "a real woman's body!"

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

The rush to eat grabbed all the students, even 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?"

The memory made Sylvia smile, "Oh Jack you should have seen him!" she exclaimed, "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 fucked his ass!"

Sylvia looked at Jack with a smile in her eyes, "you still could," she laughed, "tonight when we get together. I would love to see how he likes 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."

"Colleen said she shaved and kissed your cunt. Did you like it?" he asked.

"It felt funny for another girl to touch me, but I loved it!"

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