Jack in the Box - Cover

Jack in the Box

Copyright© 2024 by DeepInside

Chapter 5: Pool Party Celebration

Erotica Sex Story: Chapter 5: Pool Party Celebration - "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  

After the track meet ended all the out-of-town school athletes as well as a bunch of the locals returned to the hotel. Everyone gathered at the pool for a celebration.

The pool deck was just as crowded as last night and the mood was jubilant. Jack was the hero of the night, and more than one girl offered to have sex with him. Jack never said no, but he never said yes either.

Coach Bruce and Coach Kit sat at a table enjoying the success of the track meet and 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 onto the pool area wearing Kit’s white two-piece bikini. She looked stunning! Kit’s suit fit Sylvia perfectly, and her smallish tits seemed much more prominent. Sylvia had the transparent cover-up on, which only highlighted how little of her body the suit covered.

With a runway demeanor, Sylvia strutted over to Jack and took off the 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 was getting hard.

“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 in the room.”

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 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, a 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 later tonight and she couldn’t wait.

“Do you think Logan is jealous?” Sylvia asked.

Jack knew Logan was, but he 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 didn’t think I could ever wear a suit that tiny. 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 and claimed the suit belonged to her. “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 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, I couldn’t believe his cock got hard!”

Jack laughed. “Who knew! I guess I should have kept fucking his ass last night!”

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 love 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 for food; 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!” She stepped out of the pool giving Logan a dirty look.

“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 one touches her.”

So far, so good, Jack laughed as he adjusted his cock before getting out of the pool. Jack saw Kit and Bruce talking 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 did a double take when she noticed Jack’s cock sticking 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. He was about to say something, but Kit beat him to it.

“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 hand-job and lick his cum off her fingers?

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

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!”

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