Clay met her in a bar. She was very well dressed, with a tight minidress that only left a little to the imagination and a pair of sharp heels, kept on her foot by a web of black string. Her name was Andi.

As soon as Clay started talking to her, it was clear that she had a night of passion in mind. Clay did too, and he deliberately came to the bar near his apartment to satisfy his goal. After a few drinks and chat, Clay and Andi walked back to his place together, her cute handbag swinging and occasionally bumping into her beautiful legs.

Clay gave Andi a seltzer and they sat down on the couch together. Clay flicked the TV on, no intentions of watching it.

“Andi, I really like you. I really, really do. You have enchanted me,” Clay said, “How about I show you the bedroom?”

“I’m glad you said that,” said Andi, taking her purse with her back to the bed. The two locked lips and fell over each other onto the comforter. Clay’s hands made their way to Andi’s great tits, his erection jabbing Andi’s thigh through his jeans.

“Wait!” Andi said, as if the moment could wait, “I don’t want this to be just us having sex. I want this to be something more.”

“You don’t want sex?” Clay asked conscientiously.

“I want to make sure that we have this again.”

“What do you mean?”

Andi pulled a small metal contraption out of her purse. Clay didn’t recognize it.

“This is a chastity cage. It goes on your dick and prevents you from having sex with anyone else. Can I put it on you?” Andi asked, popping Clay’s rock hard penis through his fly.

“No, I want to have sex!”

“If you say no, then we will fuck once, but never again. You won’t even see me again. But if you let me do this, we will fuck so many times in the future. Plus, the cage is fun, both for me and you.” To sell her argument, Andi pulled her dress down to reveal her boobs.

Clay, as much as it pained his horniness, said, “Yes.”

Andi put the cage on the top of his dick and clicked a metal ring around his dick and balls. To lock him in, she needed the two to meet. So, she started squashing his dick into the small cage. At first Clay felt pleasure, and leaked precum through the slit at the top of the cage. Then, he felt his dick cramp up hard. Andi wasn’t taking her time. Finally, she slid a little lock into place and let go. Clay’s cock was now just one inch, squeezed in by metal and a lock that was now longer than his penis. Andi put the key around her neck.

“Ow! It’s so tight!” Clay complained. Andi giggled and licked Clay’s dick, as if she was giving him a blowjob. Clay ached with tightness and pleasure.

“Okay, your turn! Make me come!” Andi said, standing up and dropping her panties to the floor. She lifted her dress and Clay started giving her head, despite the pain it caused his penis.

Eventually Andi got bored and fell asleep in one of his T-shirts, her bare ass exposed as she slept. Clay was too horny to sleep, powerless as he stared at the key necklace he couldn’t use.

Clay finally did drink himself to sleep, and woke up to Andi on her way out the door. She was dressed very formally: in fact, wearing his suit.

“Are you leaving and taking my suit?” Clay asked, walking over from the bedroom in his pajamas and bare feet. He heard the rhythmic clacking of the lock on the cage with each step, a humiliating noise.

“Yes, Clay. I’m a flight attendant, and I have a very busy few weeks ahead of me.”

“Wait, few weeks? How long are you going to leave me like this?”

Andi started laughing, cruelly enjoying his pain. “I’m a flight attendant. It’s my lifestyle. This makes my love life very complicated. How am I supposed to dedicate myself to a partner when I’m in a different big city every weekend? So, instead, I made my own way. In each dedicated city, I have a partner who’s dedicated to me, and only me. Plus, that little cage prevents you from being disloyal and getting STIs while I’m gone.”

Clay was eyeing the key not-so-subtly.

“Tsk tsk!” Andi said, dropping the key into her bra and opening his apartment door, “You don’t want to go grabbing there when the public can see you, now do you?”

“You can’t hold my dick hostage! I’ll break out of this thing! Then I won’t need your key!”

“Let me save you a lot of trouble, Clay. It’s inescapable. The frame is made of titanium, and so is the lock. The lock is unpickable. If you ever made it through the metal, you will have seriously injured yourself to the point that the last thing you’d be thinking of is sex.”

Clay impotently grabbed his cage and tried to pull it off. His overfilled balls prevented that–he’d have to rip them off to free his cock.

“Haha! Now you’re playing my game. You listen to me, and do everything I say, then I will come back here. You fail, and I’ll never come back to your city again. That means no more orgasms for you. I have your phone number. I will send instructions. You will reply with photographic proof that you have complied. Oh, and from now on, you call me Mistress.”

Andi left in Clay’s suit, leaving him to futilely try every tool in his home on the cage. Andi was right about the injuring himself thing. But he was still so horny, and needed to cum. He jerking off through the cage. It didn’t work at all. He pressed a vibrating egg beater against the cage. All it did was frustrate him. That only left anal, which Jeff had never done before and was disgusted by. All the while, he walked around his apartment clacking, leaking, and barefoot.

The clacking and leaking had to stop. It took a few pieces of tape, but he successfully contracted the lock to the cage. More tape kept a few cotton balls on the top of his cock. It felt like a diaper, which really humiliated him. Then, the first text from Andi came in.

Jeff would not see Andi again for three months.