A.I.Dentity - Chapter Twenty-Five (Patreon)

Amy guided him towards the bar as Leslie struggled to keep the towel cinched. It was around his fake tits, tucked tight, but it was short...barely covering his crotch and ass. Every move threatened to have it drop, or expose, or...

"I see I timed it right! Showered and shaved and all ready for the big night…"

"…uh wait, what…"

She was practically pulling him towards the bar now. He scampered behind her, trying to hold everything cinched with one hand. "Ok… sit pretty girl. We're going to get you all ready…" The bar stool was pulled out and it wasn't so much a request as an instruction. Leslie squirmed. Sitting meant figuring out how to keep the towel adjusted and… The pull on his bare shoulder from Amy's soft touch started the movement in action. The towel threatened to fall, and he grasped it tightly, pulling it up, which left his cage completely exposed. He yanked it down trying to cover it, which threatened the tiny cinch at his chest. Using both hands he tried to adjust frantically… anything to keep the tiny cage hidden from the woman right next to him.

"Ready for…?" His brain was trying to catch up, but between his tired brain and the physical gymnastics of maintaining towel modesty, he was struggling. Not to mention…

It was impossible not to be aware of the little toy up inside. Sitting on the stool had shifted the position and it was making him…

He wriggled.

It shifted inside him, hitting a spot that made his eyes want to cross. He felt a little throb between his legs into the unyielding cage.

This was too much. He did not want to be aroused by this. He did not want to feel so submissive and receptive and…

It shifted again. He wriggled.

"Relax, girlfriend. We're going to have you smoking hot for him with time to spare. Here…"

With a whoosh, she spread the plastic drop cloth over him. He felt her fingers attaching the velcro behind his neck. Relief flooded him, knowing he didn't have to worry about the towel — but at the same time… it felt constricting. The thin plastic felt like another form of bondage… keeping his hands from being able to protect whatever she had planned for his head. He looked up at her.

Wait.

Him? She was… here to… this was…

"…um Miss Amy… I think maybe there was a mistake… I…" She smirked, running her hands through Leslie's hair. It felt… invasively erotic. She was looking at him like she was evaluating.

"…got the jitters, huh? You do look a little pale."

She moved behind him, her hands still sliding through his hair, nails grazing his scalp beneath.

"Tell me you ate something today… I know you got this whole hot, skinny bitch thing goin, but you need some food in your stomach… otherwise half a drink is going to have you on your back…" She laughed, her hands going to his shoulders and giving him a playful squeeze. "…or is that the plan?"

His brain instantly visualized her words and his head was shaking even before words could form. The wriggling made the toy shift inside him. It hit the spot that made him throb and a little liquid oozed out of the cage.

"I… no, I… I had some yogurt this morning… but I…"

Amy squeezed his shoulders again.

"Damn girl! You've got more willpower than I do… you should really eat something… Seriously…" Leslie tried to think of what to say, his mouth making little O sounds. He was so hungry. With everything happening, it hadn't been a focus, but now his stomach had woken up with a gurgle that was audible.

*Leslie is on a minimal low-calorie fast, but is allowed a small snack in the afternoon.*

The Mistress's voice cut through the room and Amy looked around with a chuckle. "I forgot all about your little AI 'Mistress'. So fucking cool." Leslie wanted to crawl into a ball and disappear. Just when it felt like things could not be more embarrassing, a new level of humiliation overshadowed it. "I'm not calling it Mistress though. Not kink shaming or anything… you do you… it's just not my thing… but hey… let's try this… Miss Tress. This is Amy. Is it ok if I call you Tress for short?"

*Hello, Amy. Tress is an excellent name.*

Leslie shifted, feeling the thing inside him shift again. Under the plastic he felt the towel shift and he tried to adjust while squirming. Something about Amy talking to the Mistress as an equal made him feel small… his brain already struggling to fight against the humiliating subspace he was in… and this was nudging him further into feeling inferior and helpless.

"Nice. So… Tress… has our little Leslie been good with her diet today? Can we risk a banana?" She was already grabbing one off the counter, her hands breaking the top and starting to peel it. She winked at Leslie.

*Half of a banana is a perfect afternoon snack for Leslie.*

Amy laughed.

"Damn. Your Mistress is strict, girl. But hey… something's better than nothing, right?" She held the half-peeled banana towards Leslie. He didn't know what to do. His hands were under the plastic sheet and if he moved them he would reveal his lap… and he was pretty sure the towel was no longer covering the cage. He looked up at Amy with big eyes, trying to find any words, but his brain just couldn't seem to put thoughts together. Feeling more submissive than he had ever felt in his life, he slowly opened his mouth.

A smile crept onto Amy's lips as she pressed the banana to Leslie's lips. Leslie didn't know where to look. The smile was… it wasn't mocking… it was something…

The tip of the banana slid into his mouth and he took a small bite. His stomach gurgled at the taste. He really was famished.

Amy cleared her throat.

"So… um… Leslie… you look pretty tense. Your date tonight have you all hot and flustered?" She pressed the banana towards his mouth again and he took another bite, but with the banana pressed to his mouth he couldn't really talk. He wanted to deny that he was going on a date… but then… it was something planned… something that was about to happen. He wanted to agree that he felt flustered and scared and out of control… but with no words he didn't know how to communicate anything… He shook and then nodded his head.

"Yeah… you're flustered…" Amy laughed, pressing the banana to his lips again and sliding more of it into his mouth. She was definitely smiling… looking at him… there was an odd sensual and disturbing feeling to having her feed him like this. It felt… His brain tried to deny the phallic nature of what was happening… of her standing over him, of looking up at her as she pushed something into his mouth…

"Let's see if we can get you to relax a bit, eh?" She said, looking around the room. She seemed a bit flustered and not her normal bubbly self… as if feeding him the banana like that was awkward for her too.

"Do you have any headphones?"

Leslie nodded, swallowing the bite of banana.

*There are bluetooth earbuds available.*

"Thanks, Tress." Amy smiled at Leslie. "Where do you keep them?"

Leslie's brain went blank. His mind was on the banana still hovering an inch from his lips, and on the toy inside him that was gently touching a spot that made it impossible to think.

"Um… desk drawer…" The answer popped out of him before he had time to think it through.

"Great." Amy pressed the banana between his lips again. "Last bite. Your Mistress says you only get half."

…oh god…

The way she said it made him throb in the cage. He felt himself squirt, the liquid on his bare thigh.

He took the bite, and then she pulled the banana away, tossing the other half into the bin at the end of the counter. His stomach rumbled. Half a banana and a small cup of yogurt. That's all he'd had today. He was so hungry.

He squirmed under the plastic… but Amy was already moving towards his desk. He suddenly realized that was going to take her right past the…

"What's the timer for?"

The world went into slow motion… like watching a car-wreck. Leslie tried to think of something… anything… he could say that would stop what was about to happen… but there was no time before—

*That is Leslie's chastity accountability tracker. External motivation is helpful for her goals.*

…nooooooo…

It was an internal scream. Leslie's mortification kept any word or sound from being able to escape him.

"Oh." Amy turned to look at him, her expression completely inscrutable. "So what is that… seconds, minutes…" she paused, figuring out the actual time, "hours, days… weeks? Nine weeks? That's hardcore…"

Leslie shut his eyes. Waiting for the inevitable.

*It is currently set to nine years, one hundred and eighty two days, twelve hours, ten minutes, and eighteen seconds.*

"Nine years!" Amy laughed with genuine concern, taking a step back towards him. "You can't stay in chastity for nine years!"

Leslie tried to form words. "I…"

*Leslie instructed me to add eleven years to it herself this morning.*

Amy laughed.

"You kinky bitch. No wonder you're all hot and bothered… but you can't really do that… that's crazy…Just a game, right?"

*Leslie earns time off for being a good girl, and adds time for being naughty.*

Amy bit her lip, holding back a grin.

"So… what you're saying Tress, is that Leslie has been a very naughty girl?"

Leslie felt himself die inside a little, even as his whole body tingled with unwanted arousal. Amy just called him naughty and was treating him like…

*Leslie has been a very naughty girl, Amy.*

Amy opened her mouth in shocked joy towards Leslie with an I can't believe this expression.

"Not going to lie, girl. That is fucking hot." She laughed, heading over to his desk. "So… Tress… if Leslie is a good girl for me, will you give her some time off for good behavior?"

*Absolutely Amy. If you tell me Leslie has been a good girl, I will remove thirty days. If you feel she has been bad, I will add ten.*

Amy laughed. A full on laugh.

"Hear that, Leslie? Better be a good girl for me."

Leslie realized he was trembling. Actually trembling, his body twitching out of his control. It was all too much. He was naked except for a towel, wearing a chastity device… with a toy inside him… being dominated by a cosmetician. It was literally one of his fiction wanking stories in person… and it was… it was not fiction. It was happening to him in a way that was making him…

"Here they are…" Amy had moved to his desk, pulling out the little earbud case.

"Damn, so tiny. Didn't know they could be that small…" The words made his heart stop… before he realized she was talking about the headphones.

She was walking back to him, already pulling them out of the case.

"Here's the deal, Leslie." Her voice was kind… but unnervingly firm. "We got to get you more relaxed. You look like you're about to explode. So… if you want to be a good girl for me and get your little timer down, all you have to do is just relax. Ok?"

Her fingers were already sliding one of the tiny earbuds into his ear.

"I'm going to fix your hair up for you… give you some nice makeup for tonight… the works, ok? Just relax and let me get you ready." The other earbud went in, her touch making him shiver.

"Tress… can you put on some relaxing music for her please?"

*Absolutely Amy. I'll pull some music from her downloads folder.*

Leslie's eyes widened, his mouth opening.

…from my downloads folder… but that would be…

Music began to play in his ears. Pulsing slow ambient sound. He knew what it was even before the voice started.

…hypnosis tracks.

…from my downloads folder…

The files he had downloaded to jerk off to.

…oh god…

Leslie felt himself try to harden further in the cage, but there was no room. Just unyielding ache. He felt Amy's hands go back into his hair, examining it.

"Tress. I think we need to get Leslie some hot oil treatment. The dye has left her hair a little dry. Maybe some VO5…"

*Alberto VO5 Moisturizing Hot Oil Treatment added to cart.*

"Excellent… now make sure that she…"

Leslie squirmed, feeling the device inside him shift and as he did, he felt…

A soft vibration inside him. Almost invisible, except…

"…would make it fuller…"

*I have added it to her schedule.*

He squirmed… squirting.

…oh god…

He felt the arousal inside growing somehow hotter. Not harder… but internally. He tried to listen to what Amy was saying. She was talking to the Mistress and they were talking about him, but all he could focus on was…

He fought back a moan, feeling more wetness coat his thighs.

"…and then tomorrow we could…"

He watched as she grabbed a bottle, squirting something onto her hands and then slowly sliding her fingers into his hair. Her touch on his scalp made his whole body tingle in a different vibration from what was inside him. The two sensations acting in unison...making his whole body electric.

*Absolutely Amy. Added to the notes.*