Jack in the Box - Cover

Jack in the Box

Copyright© 2024 by DeepInside

Chapter 4: The Race

Erotica Sex Story: Chapter 4: The Race - "Jack," a well-endowed student has fucked his way through the willing young girls in his high school. On a bus headed to the regional track and field meet his well-endowed track coach hits on him. Jack quickly takes control and turns the tables on her and she becomes putty in his capable hands. Future chapters explore male domination and submission and self-discovery.

Caution: This Erotica Sex Story contains strong sexual content, including mt/ft   Ma/ft   mt/Fa   Fa/ft   Mult   Teenagers   Coercion   Consensual   Reluctant   Lesbian   BiSexual   Heterosexual   Fiction   School   BDSM   DomSub   MaleDom   Humiliation   Rough   Spanking   Torture   Group Sex   Orgy   Interracial   Anal Sex   Analingus   Cream Pie   Exhibitionism   First   Facial   Oral Sex   Pegging   Sex Toys   Tit-Fucking   Voyeurism   Big Breasts   Small Breasts   Teacher/Student  

Kit woke early. Jack was naked and sprawled out beside her on the hotel room bed. Their new teacher/student relationship was taboo and thrilling. Last night, they explored each other in ways that she had never imagined possible. As Kit watched him sleep, she felt a mixture of desire and peace wash over her. She reached out, trailing her fingertips down his chest, over his defined abs, and then lower, teasing his big balls at the base of his cock. As one of his track coaches, she had admired his form many times. But seeing him naked like this, feeling his muscles tense under her touch, was on an entirely different level.

His flaccid cock called out to her like a beacon in the dark. She reached over and gently stroked his young teen cock. He had the best kind of cock, extra thick and long, and full of tasty cum. Kit knelt between his legs and took his cock into her mouth, sucking and licking as she moved her head up and down. She could feel him growing harder in her obedient thirty-one-year-old mouth and her eyes searched for his permission to continue.

Coming awake Jack’s hands tangled in her long red hair, guiding her movements. He took control and forced his teacher to take him down her throat. Making her gag on him. The sounds she made as he fucked her face were almost more than he could take. She was so perfect, so obedient, so talented with her mouth. He had no idea she was so special, but now he was overwhelmed with desire for her.

He let her up for air and she smiled and said good morning. He didn’t return the greeting and pushed her back down again, harder this time. He could feel himself getting close, his hips bucking against her face as he tried to hold back, to make it last. But it was no use. He was lost in the pleasure of her mouth, in the feel of her mature body on top of him. With a loud groan, he erupted, spurting hot cum down her throat, and she obediently swallowed every drop.

Last night Kit begged him to make her his sex slave. To abuse her body any way he wanted, she craved rough sex and submission. He made her scream out his name, and then he’d fucked her even harder. He was free to unleash all his pent-up energy to see just how much she could take, and then he pushed her farther. And he found out she loved it. She loved the way he took control and obeyed him without fail. He knew they had to keep this a secret, but he wished he could just tell the world about their forbidden relationship.

Kit loved her new Master. It was a thrill to obey his every command. He was the perfect mix of strong and gentle, and she couldn’t bear the thought of losing him now that they had come together. Kit hoped that Jack felt the same way about her. She submitted completely, to his touch, his voice, and his cock. Every part of her ached from his aggressive lovemaking. And she never thought she would ever be truly this happy ever again, and she was determined to make the most of it.

A worried thought made Kit frown. Last night, Logan and Sylvia learned about her relationship with Jack. Now her future was in the hands of two more students. Jack made them all have sex together, and Logan fucked her ass. It was thrilling and scary at the same time. Kit didn’t know what they would do with this information. She hoped they wouldn’t tell anyone else and she looked forward to having sex with Sylvia again. The young girl was so obedient and eager to please. Kit couldn’t wait to have a threesome with Sylvia and Jack.

Kit revealed her history to Jack last night and he listened without judging. She disclosed her need for rough submissive sex. It wasn’t a pretty story, and she was lucky to have survived the ordeal that marked her psyche for life. Jack said he understood her desire for punishment and agreed to be her Dom, her Master, to ensure she got what she needed. Kit felt a rush of relief and gratitude wash over her and bowed at his feet in submission. The pain and pleasure he gave her after were still visible by the marks on her body. They served as a reminder of their special connection.

But Kit wasn’t the only one with secrets, last night Jack revealed his demons to her. His mom had been cheating on his dad for over a year. The bitterness in Jack’s soul left him with a twisted feeling toward girls. He subconsciously used rough sex as a means of punishment against his mom, but also as a way of finding solace.

Kit understood, and it made their connection even deeper. They lay together, entangled in each other’s arms, feeling safe and cherished. Kit welcomed Jack’s darkness, and he in turn accepted her need for punishment. They were a perfect match, made even more special by the forbidden nature of their teacher/student relationship.

The clock alarm going off meant it was six am and Jack needed to return to his room before Coach Bruce did his morning rounds. With a smile on her face, Kit licked his cock clean and gently sucked him with her very soft mouth. Her purring woke him up.

“Hmm, good morning, Kitten,” Jack yawned and smiled, “I could get used to this.”

Kit was elated that Jack was happy. “Me too; I love having you in my bed. Do you want to fuck me?”

Jack saw Kit was eager to please him. “Come kiss me good morning first.”

After what Jack disclosed last night, Kit knew asking for a kiss was a giant step. Jack never kissed any of the girls he fucked. She crawled up his body, kissing along the way until her lips hovered over his, letting him change his mind if he wanted to. Kit’s heart filled with optimism when Jack pulled her down; today was a new beginning for both of them.

The kiss lasted for only a few seconds, but it was a start. “You need to get back to your room before Bruce comes looking for you,” she said as she crawled back down his body. “But first, I need your cock one more time!”

Jack enjoyed Kit’s mouth and the attention she gave his cock. He never expected her to be so complicated or so original. The revelations she shared with him last night amazed him, and it made his home troubles seem insignificant in comparison. He relaxed with his hand, gently stroking her hair; there was no rush to come.

“Fuck!” He was thrown off guard when his cock suddenly erupted for the second time in her mouth. Maybe it was her softness or gentleness that made him come so quickly; whatever it was, she greedily swallowed all his cum.

Kit was startled when Jack’s cum shot out but silently pleased. His stamina was incredible, and she was proud of herself for stimulating a second ejaculation.

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

“Every time,” laughed Jack. “Do you want to go downstairs and get some breakfast to go with your protein shake?”

“I would love to!” Kit 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 snickered. “By the way, how is yours?”

“Always available for you!” Kit challenged 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 to join Kit.

“Here’s your toothbrush,” Kit said enjoying the stunned look on his face.

“You had a toothbrush ready for me?”

“I bought it yesterday in the lobby store. I was hoping you would wake up in my hotel 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?” Kit laughed.

Jack loved this intimate moment, “Kit, you are so bad it puts you on a different level!

“Good!” she laughed, “because I expect you to take care of my bad side again tonight!

They finished the morning ritual of brushing their teeth and emptying bladders. After dressing, Jack stopped her at the door.

“Before we go back into the ordinary world, I want you to know I can’t imagine not being with you,” Jack announced. “I don’t know anything about being a Master, but we can go down this path together.”

Kit 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,” Kit said as her eyes teared up. “Thank you, Master.”

With one last kiss, they headed for the hall door.


Kit and Jack found Logan and Sylvia asleep in each other’s arms. They looked so peaceful, Jack didn’t want to disturb them.

“Good morning, lovebirds!” Jack said as he shook Logan. “Time to get up; we have a track meet to go to!”

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,” Kit answered, “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 sleepily.

“Um, I may have borrowed them last night,” Kit admitted, “Jack chased me down the hallway topless!”

“Really?” Logan quizzed as he woke up. Jack casually had his arm over Kit. “Are you two a couple now?” Logan asked.

Kit looked up at Jack and waited for him to answer.

“Yes,” Jack said, “but don’t tell anyone; I don’t want Kit 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 Kit nodded. “Good, now group hug!”

The awkwardness passed when Kit tugged on Logan’s cock. Not to be outdone, Jack pushed his fingers up Sylvia’s cunt.

“You know we’re going to fuck both of you again, don’t you?” Kit said as she looked from Logan to Sylvia. “Jack and I talked about this last night.”

“We were hoping so!” Logan said, “We talked too and want to do it again.” Logan blushed at the thought of Jack’s cock in his ass again.

Jack leaned into Sylvia and kissed her; he felt her cunt get wet. The look of surprise at being kissed by him said it all. “Tonight, you’re going to have a cock in your cunt and one in your ass at the same time.” What he didn’t say is Kit would be using one of her dildos on Sylvia.

“Oh god! Yes! I want to do that!” Sylvia exclaimed as she squirmed on Jack’s fingers.

Kit knelt and gave Logan’s cock a quick suck. “Hmm, I taste Sylvia on you,” she said. “I like it.”

Kit stood and looked at Sylvia. “Tonight, your mouth is going to suck my cunt until I come all over your face.” She forced a finger into Sylvia’s mouth. “This sweet little mouth is going to please me in so many ways!”

“Fuck!” Logan exclaimed, “That’s so hot!”

Kit kissed Sylvia 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 at that moment. “I can’t wait!” she exclaimed.

Jack pulled his fingers out of Sylvia’s cunt and rubbed her lips, “open up and taste yourself.”

Kit knew this was going to be an exciting arrangement. The plan was for her and Jack to take advantage of Sylvia and Logan’s naivete.

“We need to get going,” Kit said, “Jack and I will meet you downstairs for breakfast.”

Jack nodded in agreement. “Logan, you are one lucky guy to have such a sexy girlfriend!”

“I know!” he responded. But Sylvia didn’t share his excitement.

Jack and Kit left the room and walked to the stairwell. “That went well, I think,” Jack mused. “Good move going first with Logan’s cock. It made him feel like he was still part of the group.”

“Do you think Sylvia will do all the things we want her to?” Kit asked.

“One hundred percent!” Jack enthused, “Sylvia is going to be our live sex toy.”

“Even Logan?”

“I had my cock in his ass 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.


The breakfast room overflowed with teenagers and coaches from competing schools. Kit spotted Bruce and went over to him as Jack got in line for some carbs.

“Bruce, I am so sorry!” Kit said as she cuddled up to him in his personal space, “I feel like a bitch for abandoning you last night!”

When Kit’s breast touched his arm, Bruce forgot all about her breach, “It was a little hectic, but I managed.”

“You’ve been working out!” Kit gushed as she squeezed his muscles.

Jack laughed as Coach Buchanan pumped out his chest to something Kit said to him.

“I rode down in the elevator with Jack,” Kit said, trying hard to keep a straight face. “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 performance today.”

Bruce turned white, avoiding Kit’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 fine.”

“That’s strange?” she said, glancing back at Jack. “I mean, if anything is going on, I’m sure Jack will tell me, but I’ll keep an eye on Logan just in case.” She placed a hand on Bruce’s shoulder, giving it a reassuring squeeze. “Oh, well, I hope everyone does well today! See you on the bus ride to the stadium. I hope our kids do well today!”

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