The pool

"Let's check out the pool," Callie says. You follow her to the end of the beach and back to the path that leads to the various points of interest on the island. A sign points you in the direction of the pool.

"I'm sorry miss, but all men must be prepared before they enter the pool. Wouldn't want anything to contaminate the water." An employee stops you as you get close to where the pools are.

"Of course, I understand. I'll unlock him for you," Callie says. She unlocks you and hands the cage and key to the employee.

"Than you so much!" the employee says. "Come with me." The employee leads you into a building with various stalls and stations. Callie stays behind and heads to the bar to order a drink.

"Have one ready for you, Sara," the employee says. A woman steps into view. You recognize her! The other employee hands Sara your cage and key. You went to high school with her; never really talked, but she definitely knew who you were. You had a bit of a crush on her, but it never amounted to anything. She is a tall brunette with nice perky tits, but her uniform conceals them fairly well.

"John!? Is that you?" Sara asks.

"Yeah, it's me," you answer with a nervous smile. "Good to see you, Sara."

"I never thought you would come to a place like this," Sara says, staring down at your cock. "Well, sit down, we have some work to do. This will be fun." You sit in the strange chair, and Sarah clamps your hands and feet to it, completely restraining you. Your legs are spread wide apart. She pulls on 2 gloves.

"First, we need to shave you; make sure you're completely clean down there," Sara informs you. "It's best to do this when erect," she says. "Could you do that for me or do you need help?" You want to get hard, but your cock is already exhausted from fighting the cage all day. Without getting an answer, Sara takes a gloved hand and fondles your balls for a few seconds. Just like that, you have a nice boner sticking straight up.

"Pretty fast reaction there," Sara smirks. "You grow a little bit too. I was worried when I saw that tiny cage," Sara laughs. She starts to remove all of the hair that was starting to grow back. When she is done, she cleans you off with a washcloth. You blush during the entire experience, embarrassed that she is cleaning you like a child. It doesn't help that she is fully clothed and you don't even have your cage to cover you.

When Sara is done, she pulls out her phone and snaps a quick photo of you in the chair.

"What was that for?" you ask her. "Please delete that. Don't show anyone, I thought you weren't allowed to take pictures," you beg.

"GUESTS aren't allowed to take photos. Now, are we going to have a problem?" Sara asks with a sly look on her face.

"No," you whisper.

"Don't worry, I won't show anyone," Sarah says. "I could get in huge trouble, I'll just save this one for my personal collection. I'll go ahead and take care of this too," Sarah says, wiping Brad's cum off of your chest. You blush furiously, mortified that your high school crush saw you with another man's seed on your chest. When Sara is done, she pulls a machine right in front of where you are sitting in the chair.

"We don't want to risk any ejaculation in the pool," Sarah tells you. "This will help make sure you don't get too excited in the pool. It's good that you're already excited, that makes this a lot easier," Sara says, giving your boner tug with her gloved hand. Sara puts the machine right between your legs, and you can see an opening where your cock will eventually go.

"How long is that dick of yours?" Sarah asks.

"6 inches, hard," you reply. Sara scoffs.

"Let's measure it, just to be sure," Sara says, grabbing a ruler off a nearby table. She holds it next to your penis, but leaves a little room between the base.

"5 inches," Sara announces proudly. "Below average, but not too bad." You are angry at her for mocking your size, especially after she didn't even measure properly. Sara grabs a corresponding tube and puts it on over your cock. It fits snugly, and you wonder to yourself if you really are only 5 inches. Sara hooks up the tube to the machine. You can't exactly see what it is going to do, as it covers your pubic area once in position.

"I'm going to begin the process," Sara says. She presses a button on the machine, and you instantly feel a sensation not unlike what having sex feels like. Something is also massaging your balls, and you feel that you are going to cum soon. Once you release a load, the machine stops; ruining your orgasm. You moan with frustration, and Sara holds back laughter. This process repeats itself 2 more times, until you feel that your balls are absolutely drained. Your erection goes away, and Sara disconnects the machine.

"You didn't last very long," Sara teases. "Makes my job easier though, so I'm not complaining. I'm sure you get enough hassle from girls already." Sara moves the machine away, and begins to unlock your limbs from the chair. Your cock is looking a little smaller than usual. You are sexually exhausted after all of the ruined orgasms and denied arousal.

"Stand over there," Sara says, pointing to a spot with a drain on the floor. You see 2 chains hanging down from the ceiling and foot clamps on the ground. Sara follows you and restrains you again. Your arms are raised in the air, leaving you completely exposed. Sara tickles you for a second, and you squirm, but the restraints hold.

"Just making sure you're secure," Sara says with a wink. She turns a knob on the wall, and a shower turns on above you. The water is cold, and you shiver. After Sara determines that you are clean enough, she turns the water off. The sexual overuse, combined with the cold, has made your cock only about 1.5 inches, the smallest you have ever seen it.

"Looking a little smaller there," Sara says, taking notice. She grabs your balls, and your cock springs back to life. "I thought we took care of this!" Sara says, annoyed. She starts to furiously masturbate you, her gloves still on. It hurts, but the pleasure makes it worth it. After about 30 seconds, you see precum appear at the tip of your dick. Sara gives you a few more strokes, and then stops.

"This is my favorite trick," Sara says, smiling. "Watch." Sara waits a few seconds, and then taps the tip of your penis. As soon as she does, you dribble the last of your cum out and onto the floor. Sara wipes your cock with a towel, and it goes flaccid again. Sara takes off the chains and clamps, and says that you are ready to go.

"It was nice seeing you again, John," Sarah says, handing you back your chastity cage and key.

"Good to see you too, Sara," you reply. You hope you never see her again; this experience was extremely humiliating.