"Do you remember Olivia from the socials?" he asked as he knelt in front of her. "The one with the long black hair." Julia wasn't so good about remembering actual names of people. Instead, she remembered them by kink, by fetish, by scenes. She remembered the sounds they made when they were getting hurt or by the costumes that they wore. Every now and again, if one was especially attractive, she would remember what they looked like by description. Sergie waited for her respond but when she didn't, he let out a soft sigh and glanced up at her. "You said she was so cute you wanted to keep her in a cage under your bed."
Julia immediately perked up. "Oh, yes. I remember her. What about her?"
"Well, we've been talking a bit and we're both kind of shy and quiet and we both have a lot of the same interests and I was wondering if it would be okay if I asked her out on a date," he stammered.
She tilted her head to examine the boy that she had at her feet. He was thin and wiry, not unattractive but definitely of a certain "type". That wasn't what made her squint at him like he may have lost his mind though; below the waist, around his cock, he wore a solid steel chastity device. The device was locked and there was only one key in the world that would unlock it -- the one around her neck. For most, dating was about taking someone out, showing them a good time, and hoping they could get them in bed after. Since that wasn't going to happen here, she wasn't entirely certain his angle.
"I know it sounds silly Daddy, but I've never really dated before and it's not that I want to, you know, sleep with her," he said sheepishly as he looked up at her, cheeks starting to flush. "I just want to ask her out, get dinner, and say we went on a date. You know?"
Julia looked back down at her magazine in her lap, considering his request. "Alright. But you have to buy her some kind of pretty jewelry to give her on your first date."
"Really?" he sounded surprised. "Okay. Thank you, Daddy!" he said before leaning down to kiss the tops of her feet, one by one.
"Time for bed," she said as she stood up, beckoning him to follow behind her. Once they were in his room, she tucked him into bed and kissed him on the forehead. "When will you be going on this date?"
"Saturday. I was thinking six o'clock."
"Sweet dreams, Sergie," she said as she let herself out of his room and his house.
When Saturday rolled around, Sergie spent the afternoon cleaning up his house. He made sure everything was neat and tidy the way that Julia preferred it. There were certain rules that he had to adhere to and he knew that she would be around the next day to ensure that he had followed all of her instructions. When the doorbell rang an hour early, he was surprised. As he opened the door, he started apologizing for not being ready on account of thinking their date was at six o'clock but was promptly silenced by a more familiar voice.
"Oh, Daddy!" But his excitement died down into fretting. "I didn't know you wanted to see me today. Do you want me to call Olivia and cancel my date with her?"
"No," Julia said as she pushed past him into the house. "I just thought that since you were going out, we ought to clean your chastity device."
"Oh, okay," he answered, closing the door behind her.
She led him up the stairs to his bedroom and pulled out the chair that they used for when they did this particular ritual. "Strip," she instructed and he carefully removed all of the nice clothing he'd chosen for his date and laid it out neatly on the bed where it wouldn't wrinkle. Then, he moved over to sit down in the chair as he knew he was supposed to do. From there, he felt her wrap the leather restraints around his wrists and ankles and felt pressure on his joints as she pulled his arms together to lock them behind his back and ankles to the legs of the chair. Next came the hood. This one was made of just thin spandex -- enough that he couldn't really see much out of it but not thick enough to impair speech or his hearing. Finally, she removed her necklace and unlocked the chastity device from around his cock, being very gentle about opening the cage and sliding the ring from his body. He gave an audible sigh of relief when he felt his body free of the contraption, but the breath was soon caught in his throat when he also felt her hand running along the length of his cock, warming him up, encouraging his erection.
Before he could enjoy it too much, she was gone. Behind him was the bathroom where she washed out the device thoroughly. She returned with a wash cloth and towel. She draped the cloth across the palm of her hand and stroked the length of his cock, cupped his balls in her hand, scrubbed behind them, and tried to get her fingers all the way to his ass, just to watch him squirm. After so many days in chastity, it was easy to understand why such little stimulation caused him to leak at the very tip of his cock, which elicited such a giggle from her that he couldn't help but smile beneath his spandex hood. Toweling him off came quicker and was not quite as gentle. Then it was the waiting game. They'd spent many afternoons stuck at this phase, waiting for him to stop being excited about having her right in front of him, feeling her hands on his cock. They'd tried many different methods of dealing with it, from having to unlock him to have him do it to spanking his cock whenever it started to show signs of an erection. Today she was just going to let him fight it mentally. After all, she would have a great time explaining to his date that he wasn't ready because she couldn't get his cock back in the chastity device.
Eventually he was able to get himself under control and the very second that he did, he felt the steel slide up around his cock again. He felt the cage lock around it. He felt her leaning in to make sure everything was looking the way it should, that the device was securely locked, and that nothing was pinching. Pressing her hands into his thighs, she pushed herself up from her crouched position and began to look around the room.