Content Warning: Drugs, Hypnosis, Non-Consent, coercion, drugging, sissy
***
David was applying the final touches to his lipstick when she arrived.
They met online. Candi had messaged him first. He had been using the name Sarah for a while online. Candi told him that she was a sissy slut and that she loved playing with other sissies. She had told him that she loved breaking her own mind and breaking other sissies in.
David loved every second. He loved the fantasy of it, he loved to play the part. The two of them messaged each other for weeks, creating elaborate roleplay fantasies. She was relentless, she constantly sent him pictures of herself dressed up in lingere fucking her holes. David had only sent a few back in return. It was the first time he had ever sexted anyone. Living with your parents didn't give you many opportunities for posing in front of a mirror in heels and a chastity cage. They had been his first purchases after leaving home. After a while they talked on mic for the first time, he could hear her moaning. It was only then that David realised they were living in the same city.
David couldn't believe it. She said they should 'hang out' the moment she realised. David kept coming up with excuses, reasons to run away from it. She wore him down though. David relented one night when they were masturbating together, watching the same hypnosis video. He knew he didn't do anything and that they looked kind of dumb. There was something about them. He just loved the fantasy if being controlled, of having his freedom taken away from him. They did this pretty regularly now. They told each other that they were in chastity and they used vibrators on the cages and fucked themselves silly with dildoes. David did do it, sometimes. Right as he was pulling himself off, right as he was about to come, he told her his address and told her to come on Friday, so they could have the weekend.
David had regretted it at first, but the more Candi talked to him about it, the more excited he got. She sounded great, it would be hot to live the fantasy for a weekend. He could tell her that he had classes on Monday morning so she would have to be gone by then. She had convinced him, it would be good to live it for once, not just dream about it. She had also convinced him to stay locked up in his cage for a whole week. That had helped too.
David's lip liner kept his lips in pristine shape as he applied the last few dabs. Looking back in the mirror he was very happy with what he saw. The lipstick was perfect. He had even plucked his eyebrows. Not enough that anyone would notice, but it gave his face a certain feminine element. His outfit was cute. He was wearing an oversized grey jumper, which fell over one shoulder, revealing his favourite bra. It was a pink balconette, embroidered with small flowers. It was the only thing he had ever bought in real life. He had been so nervous and so excited, and no one had even batted an eyelid. Also under the jumper were his favourite panties, white cotton, which brushed softly against his cock, throbbing in its cage.
Unsteady on his heels, David made his way tentatively to the front door, making sure the curtains were entirely closed. He cracked the door open, nervous to be exposed in his current outfit.
The door flew back on its hinges the second it was unlocked. Candi looked the exact same as she did on her profile, maybe even better. She strode in on ridiculous looking heels that were at least four inches high. She was wearing a small plaid skirt that could have been mistaken for an oversized belt. It only just covered her panties which in turn only just covered her. Above that she was wearing a crop top that had brat written across it in what looked like a scrawled sharpie. Underneath that, David could see her tits, her real tits. They looked incredible. Her blonde hair was done up in space buns and she looked him up and down in black sunglasses with little hearts on them. David could see that she had two lip piercings just about holding on to lips that were bigger than he had ever thought possible.
She crashed past him, leaving the door wide open. She was trailing a pink suitcase behind her. David rushed to close the door behind her, Thankfully the only person out there was the woman behind the wheel of the fancy car that had driven Cindi here. David shut the door as fast as he could, hiding the world from him. He turned and stared in open mouthed admiration at Candi. He started to feel a little underdressed.
"Oh my god! you must be Sarah!" She ran over to hug him, pressing herself into him. He could feel her tits, they felt amazing. "You look soo cute!" she told him in her squeaky voice.
"Thanks" was the best that David could manage in response. Although he did his best to say it in a girly voice. He loved playing the part.
"I can't believe you forgot I was coming! You silly thing! We have to get you dressed! Come on!"
He tried to protest. She grabbed him by the hand and started to march through the house looking for the bedroom. She had her suitcase in one hand and him in the other. He was only just keeping up with her, even though his heels were so much smaller. He was a little out of breath by the time she found his room.
He stood and watched as her tiny frame somehow threw the enormous suitcase onto the bed. She opened it and inside was the most amazing collection he had ever seen. It was a wrything mess of latex and PVC, he could see whips and chains wrapped around corsetry.
"I have the perfect thing for you, I just know it!" She told him and started to tear into the case sending lube and buttplugs across his floor.
He came and started to sort through the case, rubbing his hands across the fabrics, feeling the stretch on the latex, imagining how tight it would feel. His cock started throbbing in its cage.
"Here you go!" Candi shouted pushing a small stain thong at him.
She was already tearing at his clothes, throwing aside his jumper to reveal his bra and panties. David beamed. This was it, this was everything he had hoped for. A chance to act like Sally, to play her and not have to be embarrassed. He didn't even know Candi's real name. He realised she didn't know his either. He could be anyone he wanted to be.
