"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.
"Where is the present that you bought for Olivia?"
"On my nightstand. It's in the pink and green bag. I bought her a necklace."
"You always do," she mused as she walked to the night stand and pushed the tissue paper aside to see what kind of necklace he'd chosen. He usually had good taste in jewelry, assuring that he matched styles to individuals and never going for anything too mainstream. "This ought to do," she said quietly as she picked the bag up. "Oh, would you look at that? Five til."
Making her way over to him, she patted him on the head and grinned. "I'll be back in a little while. You stay put."
He wasn't sure what to make of what she'd said or the fact that he was still restrained to a chair without any clothes on when his date was supposed to be there in five minutes. Surely she would release him, let him get dressed. He was certain she was just going to embarrass him a little, make him a little late, wait to see what he came up with to tell Olivia. But when he heard her leave his room, go down the stairs, he started to worry. When the doorbell rang and he heard her open that door and two voices carried through the empty halls, he started to get nervous. The only sound that could be worse than that would be two sets of footsteps coming up the stairs. Barring that, the sound of the door closing and not hearing anything. It was the latter that he received. His stomach dropped. The waiting game. This was not a new game for him.
In the still and dark of the bedroom, there was little else for him to do but worry and sleep. He did his fair share of both. Finally, he heard the door. As soon as it opened, he perked up. When it closed and there were no voices, he began to worry. The sound of footsteps hurrying up the stairs reassured him for a moment but he wondered what if it were someone other than Daddy. What would they think? What if it was Olivia? Would she laugh at him? Would he like it if she laughed at him? His cock twitched in the chastity device. Maybe. Maybe just a little bit.
Before he could lose himself in a world of fantasy, the hood was yanked off of his head and he blinked a few times, unused to any kind of light. His Daddy stood before him, looking quite pleased with herself.
"I had a great date, thank you. She really liked the present that I got her, but I don't think it was pretty enough for her." Without another word, she went to his closet and dragged out the kennel that they had used from time to time. Then, she reached into her jacket pocket and withdrew a folded piece of paper. From his desk she got tape, and she taped a picture of Olivia at the very end of the kennel, the part that was facing the bed. Going to his chair, she unlocked his arms and made sure he moved them slowly. A long drawn out sigh of relief came from him when the pressure was relieved from his shoulders. Next came his ankles, and he took the liberty of flexing his feet and pressing them against the floor. Before he could get too comfortable though, she escorted him to the kennel and put him inside. A small box containing her leftovers was shoved inside and then she closed the door and locked it. A bottle was hooked to the outside of the cage, the nozzle shoved between the bars so that he could drink at his leisure.
"Daddy, what if I have to pee?" he asked quietly. Sometimes she was sweet and would walk him out so he could. Sometimes though, sometimes she was just mean. The grin on her face gave him the answer he needed and he opened the box of leftovers and buried his face inside. He was starving.