Pleasurable Night

John sat down or was placed down on his recently enhanced rear and a pair of arms came to put a pair of white four inch stiletto heels with two thin buckled straps around his ankle. “Tixie, it is time for your continued education on how to walk in a desirable fashion in your preferred choice of footwear. Please move to the treadmill. “ As Hanna said that the wall opened opposite his bed with the same reflective screen by it, allowing John to see himself in the light green negligee or this version of himself.

He heard the words Hanna had said, but did not process any of them. Instead his eyes just lingered on himself. The blonde hair, the large set of tits sitting in the sexy negligee, his eyes watched as the girls chest heaved with each breath. Some part of the brain new it was himself, but most of his mind was lost in the **** induced fog. The more primal part of his mind registered how sexy the person was he was looking at as she parted her legs and he watched as she touched those long smooth legs. His breathing was becoming more ragged as he could swear he was feeling her touch on his leg as she touched herself.

“Trixie, comply with instruction or you will be assisted.”

“Huh?” A light shock went through his body that pulled him away from his lust and more into the present. He wasn’t sure why he was shocked, but as he reached up to his neck he felt a necklace and it came back to him from earlier. “Oh no…”

Another shock ran through his body, enough to stiffen his limbs for just a split second. “Trixie, please go stand on the treadmill to begin your evening training. If you do not comply I will assist you.”

Getting to his feet John made his way to where Hanna indicated, not wanting to lose the simple freedom of being able to move his own body like earlier. Stepping onto the treadmill he tried to do what Hanna had **** him to do earlier with taking small steps, one foot in front of the other and moving his hips. It apparently hadn’t been good enough, as mechanical arms came down holding his elbows in while his arms were out. Another set took hold of his hips and moved them in a more exaggerated way that John was doing it. “You are making me move like some slut.”

“Your desire for male attention has already been added to your profile Trixie. When you learn this walk you will get the desired results.”

“I’m not Trixie you stupid machine, I am John. I’m John Bell!” A shock went through John’s body, cutting off any more words he might have yelled to the home AI.

“Trixie, you may speak during training, but you must continue with the activity selected to help you. I have checked system profiles and found no active user named John Bell, you are user Beatrix Bell, with preference selected to be referred to as Trixie.”

This house had him held hostage in his own room, on a treadmill and **** him to move way that did terrible things to his imprisoned dick when he looked at his image. So John closed his eyes and just moved as Hanna wanted him to. It would be over faster and be a lot less painful. As his hips swayed he thought about his cramped feet, making sure to move heel, toe, heel, toe as he placed one foot in front of the other. He tried to think about how he was going to get out of this, but that only caused him to miss a step, earning him a shock. So for the next forty minutes , ten minutes longer than the last time John gave all of what little attention his mind could give to the so called training.

When the treadmill came to a stop John let out a long sigh, taking in his appealing form again. “So glad that is over, it is making me so horny.” Stepping off the treadmill John moved over to his bed, thinking about how he was going to snap the heel off these shoes so Hanna could not make him wear them again. As he plopped down on the bed, John pulled one of his legs up and unclasped the first buckle of the white heel, though it took him a few tries with the long nails.

“You must leave your shoes on at all times Trixie, you have already been warned of this earlier today. You have not been given permission to go barefoot.”

“Fuck you Hanna and who ever programmed you too!”

John went back to trying to get the second buckle off when he felt a shock a now familiar shock go through his body. “Due to noncompliance you have been given a corrective nudge to help you follow the rules.”

“Shocking me is not corrective!” John abandoned his foot and reached for his neck, feeling around it for some sort of clasp, but found none.

“Incorrect, due to your consistent non compliance with rules and need for training you will receive increasing levels of electricity that correct your behavior. Do not worry, at no time will there be any lasting harm to you Trixie. I am here to help, not harm.” A mechanical arm came out of the floor and wrapped around John’s foot for a few seconds before moving back inside the floorboards. Looking back down at his foot John could see the heel was rebuckled.

“Hanna do you really think this is an appropriate way for a man to sleep?” He didn’t expect to win the thing over, he was just tired and a bit horny from sadly looking at himself.

“Trixie you are dressed to excite a man you wish to bed, it is appropriate attire for you, not a male.”

John groaned and layed down on his back, looking up at the white ceiling. “Could be worse, I could have to sleep in curlers.” Reaching down between his legs John pulled on the tape holding himself secure. While the tape didn’t feel good to be removed, once it was felt fantastic. His balls descended once more and his dick that was already semi hard was free inside the light sexy panties. Touching his dick with his long nailed fingers felt great, and it was easy to imagine some sexy girl’s hand was wrapped around his member. With his other hand he ran it over the sexy clothing he was wearing, and grabbed his C cup chest.

They felt so real, but he didn’t get some jolt of pleasure through him like girls seemed to when he touched them. It felt like his had tits, but they hadn’t gained some extra sensitivity from the expansion. It was all so odd and knowing he was touching himself wasn’t doing much for him. John licked his hand for some lubrication as he jerked himself off, but he wasn’t able to keep the form of any fantasies like he normally would in his mind.

He could picture Victoria getting down on her knees and licking him before taking his cock into her mouth, but his mind just didn’t seem to be able to hold onto it. Every time he thought of his pleasure or adjusted himself in any way it was enough of a distraction to pull from his mental spank bank. The movement of his chest alone could have been enough, but no matter how much he tried he seemed to be fighting a losing battle. One moment he would be hard as a rock and then it would start to fade. With a large sigh he looked over at his computer and got out of bed with his dick hanging from his panties.

He took small steps, swaying his hips as he moved to the small desk built into the wall where his computer sat. Each step reminded him of his chest, and the sexy clothes as it moved lightly about him. Turning on the screen he tried to go to one of his favorite porn sites, but found it blocked. He tried another and found the same. “Hanna, why can’t I go to these sites? They didn’t used to be blocked.”

“Trixie the sites you are trying to access are sexual in nature and indeneded for mature audiences, due to parental lock you are not allowed to access any such sites without admin approval.”

“I am not going to ask to watch porn.”

“Trixie if you like I can request approval for you to go to those sites.”

“NO for the love of anything you hold holy do not do that!” A shiver went through John at the thought of his dad getting a message asking if it was okay for him to watch Slutty Secretaries know how to ask for a raise part 2. When Hanna did say anything he went back to bed, hoping tomorrow his mind would be clearer and he didn’t have to dress like this. If it was at least the first he could figure something out, right now anything involving a two step plan seemed complicated. “Hanna, can you please turn off the lights.”

The lights in the room turned off and John closed his eyes, and as much as the pills he took made it difficult to jerk off, they made it easy to fall to sleep.

User Della has requested to get ready for bed. Hanna’s systems took the request and started to fulfill it and then moved to do the same to user Trixie due to the system setting up an auto command to give Trixie whatever Della gets, but the command to get ready for bed was canceled when the system saw it had already fulfilled that request.

Inside Della’s room Hanna had just put her down outside its dressing system in a long white T-shirt that had the word PINK on it in the same color it indicated and a pair of pink lacy boyshorts. Spending time with Sasha was exactly what she wanted and along the way she got some great payback on her brother. It was too bad it couldn’t go on, but it wasn’t like she could **** him to live as her younger cousin. Tomorrow though she was going to enjoy herself with him, but for now. She was just going to enjoy herself with some other activities.

“Hanna, could you pull up a screen and show the image of Jack Simmons from my school?”

Connecting to the school system Hanna found the student she indicated and showed his most recent photo on a screen that descended from the ceiling. It showed him in a pair of jeans, a white undershirt as he cocked back his arm to throw a football. It then changed to more photos of him that Hanna was able to find on his various social media accounts. “WIll this be sufficient?”

Della nodded as she sat up on her bed with her legs spread. “Do you think you could also show some images of Steven Summers, just like you are for Jake?” Della expected the images to flick between the two, but instead a second screen came down to show images of another one of her crushes from school.

She was about to get out one of her toys when a wicked idea came to her that she hadn’t considered before. “Hanna, do you know how to umm… get me off sexualy? I mean like.” She felt so embarrassed to ask for something like this and not sure exactly how to word it.

“Della, I have downloaded information on how to make you orgasim, is that what you wish for assistance with?”

Looking at the images of the two beefcakes on the screen Della nodded her head as she bit her lip. “Yes please Hanna, give me that kind of assistance.”

Back inside John’s room where he was fast a sleep he had no chance to notice the two screens lowering to show the different images of Steven and Jack from his sister's school. What did pull John from his slumber was when he felt his legs being lifted into the air. “Huh? What is going…what?”

John had made it to REM, making him extra groggy as he woke up to see a low light filtered into his room from the screens showing two older teens on a pair of screens. He had no concept of what could be going on and would have started to panic if it wasn’t for the medication keeping him from such extremes. The next thing he noticed was when his panties were pushed to the side freeing his member and then something pressed against him. “Hanna what is going on?”

As he asked whatever cone shaped thing was pressing into his groin started to vibrate. “Per your request you want the same treatment as user Della.”

John’s eyes crossed as the vibrating dildo rubbed onto his manhood. His body was already horny and the stimulation left him hardly able to think. “No, no I did not. Hanna… stop!” Hanna’s mechanical arms had him around the thighs and was pushing his legs up, leaving his heeled feet to squirm in the air as the device tried to push its way into his nonexistent female anatomy.

“Della gets everything she wants! I just want the same treatment!”” The recording played of John's voice through the speaker. “Audio file was saved for the request. Unable to fulfill request to stop, as user Trixie no longer have privileges to make changes to profile. User Trixie is getting the same treatment as user Della.”

“Ahhh Noooo please don’t do that!” John called out as he looked down as the vibrating phallic object moved down from his groin and moved his panties to the side as it pressed on his anus. From the stimulation his dick pointed up into the air, hard as it could be. John kicked his heeled feet trying to move his legs, but in his position it did nothing and held the way he was he couldn’t reach over his body to grab anything. It wasn’t until the dildo slid with lube pushed its tip inside of him did he think to reach under his legs to try and grab the dildo.

Just as he wrapped his long nailed hand around the dildo the mechanical arm pressed it in a little further and then back far enough so just the tip stayed inside John’s exposed rear. “Ahhhh god.. Get it… get it.. Out!” He cried pulling as hard as he could, but all he did was make the pullback before each thrust quicker. Hanna picked up on Trixie wanting it out faster and from the information she pulled many females loved the quick stimulation of rapid thrusts, so the dildo picked up its pace.

“OH… Oh.. oh… “Johns voice grew quieter and quieter as the dildo that moved deeper inside of him at an increasing pace changed from vibrating to a steady pulse of off for half a second, to on for half a second, off for a full second, on for a full second and back again. Eyes wide from the pain, embarrassment, sense of helplessness and pleasure. John could see and feel his chest moving, his hard dick in the air leaking precum, the sexy heeled feet in the air and the two screens showing the boys he was sure Della had a crush on.

As the cock replica pushed even deeper John’s eyes rolled in his head as it pressed on something inside of him that cause a shiver to run through his body, that caused his feet to kick in the air. The dildo pulsed, once, twice, three times as it pressed hard inside of him, not pulling back. “OH, OH, OH… eh, eh, eh, eh!” The wounds coming out of his mouth seemed to be beyond his control, this shouldn’t feel good.. It hurt, it felt like he was being split in two and yet he could feel his balls tighten just before his cock erupted like a volcano, shooting his cum into the air. His body lost much of its tension as he came, and stopped fighting the mechanical arms all together. John lay there, his mouth open and panting as the dildo pulled back and thrust into him a few more times, getting slower and slower with each thrust before coming free.

“Thank god, its over, Hanna never do that again. Please, please I beg you.”

The arms holding his legs the way they were hadn’t let go and after a few seconds he started to get worried and felt much more justified in his paranoia as he felt phallic device press back to his rear. “Trixie, that request cannot be fulfilled, user Della had decided to keep going. Systems indicate you orgasimed, please enjoy your next one as much as your first.”

Hanna began assisting Trixie in pleasure for a second time, just as it was doing to Della who was doing her best to not scream in ecstasy. She didn’t know Hanna could do this, but now that she knew about the feature she was positive she would never be bored in her room again.

When she had her fill Della asked for a glass of water as she caught her breath. Sitting on up to drink she saw an indicator light on her phone from Hanna.

Hanna: Trixie has indicated she would like to have curly hair for tomorrow, by indicating she would like to sleep in curlers. Proceed?

Della clicked yes, with a shrug. It sounded odd he would say something like that, but his dumb ass needed to learn Hanna didn’t pick up on sarcasm. She finished her water and decided to call it a night. While John lay passed out in his bed, with cum drying on his light green negligee, unaware of the world after passing out in the middle of his second fucking. The pain and pleasure was too much for his mind to take and he had slipped off into unconsciousness. The glass of water he was given was left undrunken, but Hanna did add rollers to Trixie's hair so that it would look the way she wanted for the next day.