Yes

As you exit the building, you see Callie sitting at the pool bar. She catches your eye as you walk over. You see that she has changed into a bikini.

"Hand me your cage and key, John," Callie says. "They aren't allowed in the pool." You do as she says, and she puts them in her bag. "Let's go," Callie leads the way down to the pool. There is only a few other men, so you get a lot of attention from the women. They stare at your freshly shaven cock, which is still only around 1.5 inches. You get in the pool with Callie, and she starts to splash you. You have a good time with her, and for a while, you forget about all of the embarrassment you've previously felt on this trip.

After a while, Callie is tired, so you get out of the pool and head to 2 open chairs. Women laugh as you emerge, as you have a bad case of "swim dick;" it is looking very tiny and shriveled from the cold water and chemicals in the pool. You lay on a lounge chair next to Callie, exposing all of your body to anyone who walks by.

"I'm ready to go back to my room, John," Callie says. "I can't put your cage back on because it's too big." You both stand up and head towards the exit. You get back onto the main path, and you see a man walking towards you.

"Hey, girl," he says to Callie, "You should drop this loser here and come with me."

"Maybe you're right," Callie says. You feel heartbroken as she sinks to her knees in front of the man, and unlocks his cage. "Stroke for me," Callie says, and he does.

"I'm going to cum soon, miss," the man moans.

"Stop stroking for a second," Callie says. "We're going to edge you, then you can blow a fat load on me." You wait for her to do something more, but after a while, his penis returns back to it's flaccid state. Seeing this, Callie puts his cage back on.

"Some blue balls ought to teach you some manners," Callie laughs. "Come on, John, let's go back to my room." The man whimpers in denial as you leave him standing there, having just missed out on an orgasm. As you get back to Callie's room, she goes into the bathroom to take a shower. You want to masturbate and finally have a real orgasm, but you can't risk being caught. Soon enough, Callie comes out of the bathroom. She is only wearing basketball shorts and a bra.

"We need to cage you back up, John," Callie whispers. You can hear that she is tired, it has been a long day for both of you. She rummages around in her bag, and finds an even smaller chastity cage than the one you had earlier.

You put it on, and it fits your current size perfectly.

"I like having your cock small in the cage, John," Callie tells you. "I love seeing it grow." She lays down in her bed, and motions for you to get in with her. "Don't try anything funny, or you'll be punished." You know better than to test her, and you both fall asleep.

The next morning, you wake up first. Callie has nestled herself on top of your caged cock. You wish you could fuck her right here, right now.