Jack In the Box

Colleen opened her eyes to see if Sylvia would do it. Jack just held them out; he wasn't forcing Sylvia, at least not physically.

Slowly Sylvia opened her mouth as tears welled up in her eyes.

"Wider!" Jack ordered. When her mouth was wide open, Jack put his dirty fingers in. "Now suck them clean!"

The sneer on Jack's face turned to a smile, "that's a good girl," he praised, "maybe later you can lick my ass too. Coach likes to do that."

Sylvia shot her coach a glance and saw her nod her head. All of a sudden she wished she didn't come up to Logan's room.

When Jack was satisfied, he pushed Sylvia back, and she landed on Logan. "Well that was fun, what should we do for an encore?" he laughed.

Colleen could barely maintain her balance and just before she was going to topple over Jack grabbed her.

"What do you think Logan, ass, cunt or mouth? You get to choose."

Logan had never tried anal sex before, and this was his big chance. "Ass!" he laughed.

"Okay girls, you heard the man! I want you both to bend over the bed with your asses facing me."

Colleen didn't hesitate and bent over the bed. Sylvia was crying hard now, and Colleen was feeling sorry for her. "Shh, sweetie, once you try it you are going to love it! Come lie beside me, and we can hold hands."

"We're going to need some lube," Jack said to Logan as Sylvia assumed a position beside her coach, "go see what's in the bathroom."

Logan came back with a couple of small containers. "So, we have shampoo, cream rinse, and body lotion."

"I'll take the cream rinse, and you use the body lotion. Push it into Sylvia's ass and squeeze it all in her."

Jack worked the container into this teacher's ass and squeezed until the whole container was empty. He watched Logan do the same thing and gave him a high five.

"If you girls don't want this to hurt too much I highly suggest you push out when we push in!" laughed Jack.

"What does Jack mean?" Sylvia asked her coach.

"Push like you want to poop, it will open your ass up," Colleen said as she squeezed Sylvia's hand. "Don't worry it only hurts at first; then it feels so good."

Jack moved behind Coach Coffin and spat on her ass, not for lubrication but because he wanted to. Logan followed Jack's lead and then waited to see what he did next.

"Are you ready Coach?" Jack asked as he slapped her hard on the ass. He didn't wait for her answer as he lined up his cock and pushed.

"Oh fuck you're big!" Colleen exclaimed as Jack's cock pierced her ass. "Please let me adjust!"

Logan's cock was ready, he slapped Sylvia's ass and pushed. "Fuck! It won't go in!"

Jack could see Sylvia was clenching her ass shut. "Let's switch Logan." He laughed when Logan's eyes lit up. Jack didn't wait for Coach Coffin's okay as he pulled out and Logan stood behind her. Jack could tell he was unsure if he really should do this to his teacher.

"Okay a quick slap, then push your cock in her ass," he said to Logan as Coach Coffin held his gaze.

"Oh FUCK!" Logan yelled, "it feels incredible!"

Jack smiled at his teacher and mouthed the words 'thank you' to her. He wasn't sure why he did, but he suddenly cared what she thought of him. He liked that she blew him a kiss.

Jack laid his body over Sylvia's tense one and massaged her shoulders as he let her get used to the feel of his cock between her ass cheeks. "Look at Logan; he's fucking Colleen's ass. If you had let me do that to you might be my girlfriend right now."

Colleen stared at Jack in shock; he had just used her first name when talking about her. "Jack's right Sylvia, guys like to fuck a girl in the ass. Right now Logan is doing it to me, look at him."

"Oh fuck Sylvia I can't believe how good this feels!" Logan enthused, "my cock is in Coach Coffin's ass!"

Sylvia looked at her teacher again, "I'm scared."

"You lost Jack, do you want to lose Logan too?" her teacher said, "If you don't do this he will find a girl who will."

"No, I like Logan," she said as she looked at him.

"I like you too," Logan replied, "but now that I know what this feels like Coach is right. I want to do this again and again."

Jack could feel Sylvia relaxing as his cock pushed between her legs rubbing on the outside of her cunt. "I've wanted to fuck your small ass for so long Sylvia, will you let me be the first one?"

"Do it, Sylvia, you owe this to Jack," Colleen urged, "he will be gentle I promise."

"Okay," Sylvia softly said as she looked into her teacher's eyes, "I'm glad Jack is the first one."

Colleen looked at Jack, and they exchanged smiles. "Come closer Sylvia, let me kiss you," Colleen said.

Jack spread Sylvia's legs apart as the two girls kissed, he could see Sylvia was sucking Colleen's tongue. He didn't slap her ass this time; he wanted her to be relaxed. "Push out Sylvia, let my cock in," Jack whispered into her ear.

Colleen felt Sylvia sucking harder on her tongue and knew Jack's cock had found a way in her ass.

"Good girl, now I will go slow," Jack said, "just relax and enjoy it."

Jack 'listened' to Sylvia's body; he didn't want to make her first time painful. He only had the head of his cock in her ass, but he knew that was still a lot to take.

The two girls broke apart. "You're doing it!" Colleen praised and squeezed her hand, "your first anal, I'm so proud of you!"

Jack pushed deeper enjoying her virgin ass; he was standing now hanging onto her slim hips watching his cock disappear and reappear. The hand cream was working but not as good as real lube would. He looked over and saw Logan was not holding back as he fucked Colleen's ass, and he was glad he switched places with him. Sylvia wasn't ready for a hard fuck yet.

"Oh fuck, oh fuck!" Logan screamed, "here it comes!"

The sight of Logan humped over his woman was almost comical. That thought made Jack stop and look at Colleen, and she smiled up at him. He knew right then he was falling in love with her and he smiled back.

"Are you okay Sylvia?" Jack asked.

"Oh Jack, Coach was right, it does feel good. Go faster and just a little deeper."

Sylvia didn't know it, but she was already taking most of Jack's cock. He had been working it deeper and deeper very slowly. When he had all of his cock in he stopped. "You did it, Sylvia, all of my cock is in your ass."

"I did it, Coach," Sylvia smiled, "now I'm a real woman like you!"

Colleen loved the innocence and excitement, "that's right, you're a woman now, and Logan is lucky to have you," she said, "hold my hand again, Jack's going to fuck you harder and come in your ass."

Jack felt Sylvia tense up slightly then quickly relax again. He wasn't really fucking her harder, but he knew in Sylvia's mind he was, the deep full strokes created that illusion. Logan had gone to the bathroom to clean off his cock and was standing beside him now watching his new girlfriend getting fucked in the ass.

Logan found the sight was making his cock stir. "Can I fuck your ass again Coach?"

Colleen looked at Jack and shook her head no, "only if Jack says it's okay."

Jack was close to coming, "no, you can fuck Sylvia's ass after I come."

As much as he tried Jack couldn't control himself, he was fucking her ass harder now, moving her body with force up the bed then pulling her back down by her hips. Sylvia was moaning out, and he didn't know if it was from pleasure or pain. Colleen was holding her hand and saying it wouldn't be long before Jack came in her.

"Fuck!" Jack exclaimed as his cock pulsed in Sylvia's ass. When his orgasm receded, he leaned down on top of Sylvia and kissed her on the lips.

The action took Sylvia by surprise, "you've never kissed me before."

"I know, you just earned it."

"Are you ready for Logan to fuck your ass?" he asked her.

"Yes," Sylvia said as she looked at Jack's smiling face and dimples, "thank you, Jack, for everything!"

Jack kissed her once more then stood up pulling his cock out. Sylvia's ass gaped open, winking a few times like it was also thanking him. He looked at Logan's hard cock, and slapped him on the shoulder, "not too hard Logan she is still in training."

"Okay, thanks Jack," Logan said. He moved between Sylvia's spread legs and in spite of Jack's advice he fully buried his cock in Sylvia's open ass. "Thank you, Sylvia, you're so beautiful!"

"Kiss me, Logan, kiss me while you fuck my ass!"

Colleen looked at Jack; she had waited on the bed in case he wanted to fuck her too. His coated cock was a combination of hand cream and Sylvia's ass, and she wondered if Jack was going to make her lick him clean.

"Damn you look tempting!" he said as he smiled at her, "but I think I need to clean my cock first. Do you want to help?"

Two things struck Colleen. First, he had asked and not ordered her and second she had a choice. She rose from the bouncing bed and knelt in front of him.

"Not this time Colleen, let's use a wet towel."

Jack held out his hand and helped her stand. Looking down into her eyes he saw her for the first time. "Do you know how incredible you are? I could look a lifetime for a woman like you and never find her."

Colleen didn't know what to say as she stood there in shock. She felt the same way about him. When Jack's lips found hers, it was the sweetest feeling in the world.

The loud knock on the door surprised them all.

"Jack! Logan! It's Coach Buchanan open up!"

Fuck was the unanimous word used by all of them.

Jack looked around the room formulating a plan, "ladies, please pick up your clothes and go in the bathroom." He said calmly, "Logan go lie on the other bed and pretend your jacking off.

Everyone thought Jack had lost his mind, but they obeyed him. Jack had his hand on the doorknob as he waited for the girls to close the bathroom door. He noticed Colleen didn't close it completely, and he could see her spying on what was going to happen.

Jack opened the door as Coach Buchanan was knocking for the second time. The look on his Coach's face was priceless. He could see Logan in the background moaning and jacking off, and Jack stood naked in front of him with his cock covered in a suspicious brown film.

"What the fuck!" he exclaimed.

"Hi Coach, Logan and I are just preparing for tomorrow's race." Jack said with a straight face, "we need to get rid of all our pent-up energy so we can focus."

Bruce didn't know what to do. His first thoughts were the boys were fucking each other.

"Do you want to come in and watch?" Jack asked with a straight face as Logan moaned out again.

"What? Fuck no!" he stammered.

"How can I help you then?" Jack asked with a big smile.

Bruce was having a hard time getting his thoughts together. Jack's large cock was imposing, and he couldn't stop glancing at it. "I, I'm just doing a head count," he finally said then wished he had used a different word, "you haven't seen Coach Coffin or Sylvia have you? They seem to be missing."

Jack rubbed his balls as he seemed to be deep in thought and he could see it was making his coach very nervous. "I did see them earlier; they were talking about going for a long walk. I think Sylvia is nervous about tomorrows event."

"Damn, that's twice now Coach Coffin has abandoned me. What a bitch!" As soon as the words left his mouth, Bruce regretted it. "Sorry, you won't mention I said that about her will you?"

Jack was stroking his cock now as he stood naked in front of his coach and ignored his question, "you sure you don't want to come in and watch?"

Bruce wasn't sure if he should say something more, "No! No, you boys get some sleep," he stammered, "see you in the morning."

Jack closed the door on his coach's face. "Okay Logan, we're alone again!" he said in a very loud voice knowing his coach could hear him.

Jack held his finger up to his lips to make sure no one started laughing. He peered through the peek hole and saw his coach shake his head then walk away.

"Oh my god!" Colleen exclaimed when she came out of the bathroom, "you were brilliant!"

Their laughter filled the room, and everyone agreed with Colleen's assessment of Jack. Logan's laughter was the loudest.

"We have a problem though," Jack said as he looked at his three accomplices, "we need to make it real, in case Coach Buchanan asks Logan what it feels like to get his ass fucked. I'm sorry Logan, but I need you to bend over the bed."

The laughter stopped, as they looked at Jack's serious expression. Jack looked at their stunned faces and burst out laughing. "You guys are as gullible as Coach Buchanan!"

This time Logan's laugh wasn't quite as loud, he didn't want to get his ass fucked by Jack, and thankfully no knew he had almost bent over.

Colleen hugged Jack not caring that his dirty cock was rubbing all over her body. "You're incredible! Fucking incredible!"

Jack easily picked her up, and she wrapped her legs around him. "No, you are!" he said as he kissed her passionately.

Sylvia took Logan by the hand and looked at him with soft eyes. "So boyfriend, do you want my ass, cunt or mouth?" Sylvia laughed.

Logan gave her a quick kiss, and then a big smile lit up his, "Hmm girlfriend, I never got to finish fucking your ass."

"Ass it is!" Sylvia laughed as she pulled him to the bed.

The two teenage lovers never noticed Jack carrying Coach Coffin to the bathroom or heard the sound of the shower. It wasn't until long after Logan came in Sylvia's ass and he needed to clean up that he looked for Jack. He was surprised the bathroom was empty, but he knew where his friend was. He would thank Jack again tomorrow and also Coach Coffin. Logan had a feeling they would all be spending more time together.

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A New Beginning

Colleen woke early and looked at Jack soundly asleep beside her in her bed. While Logan and Sylvia were having anal sex last night, they quietly retreated off to her room to have their own privacy.

She and Jack talked late into the night, and she disclosed how she came to like rough sex. It wasn't a pretty story, and she was lucky to have survived the ordeal that marked her psyche for life. Jack also shared his personal turmoil, and the two of them hugged and kissed after their revelations. The night ended with them having mutual oral sex, and Jack insisted that she be on top so she could control the depth of his massive cock. Colleen realized giving up control was a big step for Jack. She also knew that last night might have been a one-off, but she was hopeful that Jack meant what he said about wanting to continue seeing her.

She loved his naked body and smiled as she looked at his gorgeous cock. Even though Jack was only eighteen, he had the deftness of a seasoned lover. His intuition belied his age, and he instinctively knew how to satisfy her somewhat unique sexual needs.

The clock indicated it was almost six am and she knew Jack needed to return to his room before Coach Bruce did his rounds. With a smile on her face, she hoped waking him up with his cock in her mouth would make him happy.

Jack's dream seemed so real; his cock was being sucked very gently, by a very soft mouth. His moans are what woke him up. He couldn't see the face attached to the woman sucking his cock, but he knew it was Colleen.

"Hmm, good morning lover," Jack moaned, "I could get used to this."

Colleen came up for air and smiled at Jack. "Me too, I love having you in my bed. Do you want to come in my mouth?"

Jack could see Colleen was anxious to please him, "come kiss me good morning first."

After what Jack had disclosed to Colleen last night just asking for her to kiss him was a giant step. Jack hardly ever kissed any of the girls he fucked. She crawled up his body kissing him all the way up until her lips hovered over his, letting him change his mind if he wanted to. When he pulled her down she was optimistic today was a new beginning for him.

The kiss lasted for only a few moments, but it was a start. "You need to get back to your room before Bruce comes looking for you," Colleen said as she crawled back down his body, "and I need my morning protein!" she laughed as her mouth circled his cock again.

Jack enjoyed her mouth and the attention she was giving his cock. He never expected Colleen to be so complicated and so original. The revelations she shared with him last night still amazed him, and it made his home troubles seem so insignificant in comparison. He relaxed with his hand gently stroking her hair, there was no rush to come, and he was thrown off guard when his cock suddenly erupted in her mouth. Maybe it was her softness or gentleness that made him come so quickly, whatever it was he was pleased that she swallowed his cum.

Colleen was startled when Jack's cum shot out of his cock but silently pleased. His stamina was incredible, and she was proud of herself for his quick ejaculation.

"Hmm, thank you! Did I tell you I love the taste of your cum?"

"Just every time," laughed Jack, "do you want to go downstairs and get some breakfast to go with your protein shake?"

"I would love to!" Colleen said, "I think we should check in on Logan and Sylvia too."

"Good idea, I hope Sylvia's ass isn't too sore this morning." Jack laughed, "by the way how is yours?"

"Always available for you!" Colleen laughed as she gave his cock one last lick before jumping up and heading for the bathroom.

Jack looked around for his underwear before remembering he didn't bring any and headed to the bathroom.

"Here's your toothbrush," Colleen said as she enjoyed his stunned look.

"You had a toothbrush ready for me?"

"I bought it yesterday in the lobby store. I was hoping you would wake up in my bed!"

"Oh my god! My teacher seduced me!" Jack called out in mock dismay with both hands holding his cheeks.

"Does that make me bad?" Colleen laughed.

Jack loved this moment, "Colleen, you are so bad that even I am frightened by you!

"Good!" she laughed, "because I expect you to return the favor tonight!

They finished the morning ritual of brushing teeth, and emptying bladders then dressed. Before they left Colleen's room, Jack stopped her at the door.

"Before we go back into the ordinary world I want you to know I'm falling in love with you," Jack announced.

Colleen couldn't have been more shocked. She wanted to say 'I'm too old for you' or 'I'm your teacher' but she didn't.

"I feel the same way," Colleen said as her eyes teared up.

With one last kiss, Jack gave a big sigh and opened the door.

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One Step At a Time

Colleen and Jack found Logan and Sylvia asleep in each other's arms. They looked so peaceful that Jack didn't want to disturb them, but he knew it was the prudent thing to do.

"Good morning lovebirds!" Jack said as he shook Logan.

Sylvia was the first to open her eyes and panicked when she sat up and saw it was morning. "Fuck did we sleep in?"

"Not quite," Colleen said, "but you need to go to your room."

Sylvia yawned as she searched the floor looking for her clothes. "I don't see my panties," she said in dismay.

"Um, I may have borrowed them last night," Colleen admitted, "Jack chased me down the hallway topless!"

"Really?" Logan said as he joined in. He looked at how comfortable Jack was with his arm over Coach Coffin. "Are you two a couple now?"

Colleen looked at Jack and waited for him to answer.

"Yes," Jack said, "but don't tell anyone, I don't want Colleen to get in trouble with the school." Jack gave both Logan and Sylvia one of his patented stares. "And of course no one will ever know what went on here last night. Right?"

Logan and Sylvia shook their heads in agreement, and even Colleen nodded. "Good now group hug!"