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Sunday
Shopping day today, Claire had set her alarm so she could go to all the stores before it got too busy. Getting ready for the day she had a long hot shower and put on her clothes. Shouting her sissy to get his ass up and get ready too. She gave him permission to take his plug out before his bathroom visit, and once he was out of the shower, she watched him put it back up again. He was allowed to have his boy clothes on, and to look at him now, you would never guess what he had on underneath.
“Come on babe let’s get you some new outfits, once we’re finished we can have lunch.”
“Shopping will be fun.”
Upon entering the underwear store they had the shop to themselves, Claire instructed him loudly so the store clerk could hear, “Find some sexy panties so we can have fun.” Hopefully the clerk would think they were looking for Claire. His favourite one’s were the pink pairs but he put a lot of different style’s and colors in his basket.
“Just these please.”
“You do know that you can’t return these, we don’t accept panties back for hygiene purposes.”
“That’s fine.”
“Are you sure because you’re spending over $200, she should try atleast one pair on just incase.”
Claire said, “That was a great idea.”, Took the smallest one out of the basket and handed it to James.
“I’ll wait out here James, make sure they fit ok.”
“Yes Claire.”
“Wait those are for your boyfriend?”
“Yes but he isn’t my boyfriend, just my friend.”
“You have him wrapped around your finger.”
“I know it’s the best feeling ever to have someone so devoted to you.”
James got out of the changing room, and handed them over to the girl, Claire paid for all the item’s and thanked her. Handing the bag over he carried his new gifts.
“Thank you for the help, me and my sissy are very pleased.”
“Come here anytime you need more, is he really in chastity?”
“Tell her sissy.”
“Yes, i am Claire’s full time sissy, I’m locked in chastity and i do everything she asks.”
“Well it was nice meeting the both of you”
How many people was she going to tell? he’d only been in the changing room a few minutes. Heading to their next shop she mocked him the entire way. The next store was just normal clothes so atleast the clerk wouldn’t ask if they needed to try them on because they’d just return any that didn’t fit.
She found out a few short skirts and blouses, it wasn’t quite a maids uniform but it looked suitable for when visitors came around, she picked up some stockings and tights to match the look. She also bought some hotpants too for when he’s just lounging around, and a few normal t-shirts that had pink logo’s on them.
“Hi i was wondering if you could help me?”
“Certainly, what is it you’re after?”
“Is it ok if my sissy here tries these on before i buy them?”
“I wasn’t expecting that, of course he can, it’s just around the corner.”
Handing him his new clothes James went to try on his new outfits. Red in the face he strolled to the changing room. The assistant must have been close to sixty, not unattractive but not his type, but still having this extra humiliation was unbearable, no doubt she’ll be telling her everything he’d been doing. Most of the clothes fit perfectly, one blouse would need to go up a size though.
“Here he is, well is there anything you would like to tell the clerk?”
“Yes, I am Claire’s full time sissy, I’m locked in chastity and I’ll do anything she asks.”
“I meant do they all fit you ok.”
“Sorry, no, one of the blouses was too small, can i have the next size up please?”
“I’ll get it while you stand here with that pathetic look on your face.”
The clerk rang up all the item’s, it came to over $200. Looks like somebody wasn’t getting any wages this week. She gave him the bags to hold while she paid. The clerk smiled as they walked out of the store.
“I can’t believe you said that, that was so funny.”
“Well i didn’t realise what you were talking about.”
“I only told her you were a sissy, i didn’t go into detail.”
“Well it’s done now, one more humiliation out of the way.”
“There’s just one more store for us to go to now, it’s an adult shop.”
The adult store was very private, just a few customers looking through the dvds and blurays, nobody batted an eyelid. Claire walked straight up to the counter and asked if they sold any strap-ons, because she wanted to treat her friend. The girl just went through all the options, different sized holders for different girth, she picked a few different one’s and hoped that she could fit the 18 inch dildo in that she bought last week.
“That will be $100, if you need any further help let me know.”
“Do you know much about chastity?”
“I know quite a bit, did you want to buy a starter one to break him in?”
“Actually I’ve got him wearing a flat one now but we’re both new to this, can i get much smaller?”
“You can definitely get smaller one’s, and we do inverted ones too which will make him smaller.”
“I’ll take one of those then.”
“Are you sure because they can cause him permanent damage in the future?”
Resigned to his upcoming fate he just stood there waiting for this all to be over, permanent damage sounded horrible, and painful. The store clerk wanted to double check it was what he wanted.
“So are you sure you want your girlfriend to put you into one of these?, Like i said it could damage you permanently?”
“If Claire needs for me to have it then I’m prepared to permanently damage myself for her.”
“You didn’t even hesitate, your obviously infatuated by your keeper.”
“I love her.”
Claire paid for the new cage too, so far today they’d spent close to $700 but that was it for today. Pleased that he was so willing to buy his new cage she gave James a full on kiss when they left the shop, it’s amazing that all of this has happened and she hasn’t even had to give him any pussy yet.
“Where did you want to go for food, we could just grab a McDonald’s?”
“That sound’s good, I’m so happy with you today.”
“Why do you say that?”
“Because you trust me with your fate.”
“You are my fate now.”
“When we get home tonight I’m going to treat you to your cum filled pussy, I’m going to use up all the glazing, I’m so happy.”
Once they got home she gave him all his clothes to put away, she took the strap-on and cage and put it in his sissy drawer. Texting his cousin back she told her she’d managed to get an inverted one. Claire decided to let James read her texts to his cousin, it was his cousin’s idea to make him wear a smaller one, he couldn’t believe it, he’d soon potentially damage his cock so his cousin could get off on it. How did she even know an inverted one existed?
“It’s nearly time for your cum filled treat.”
“I’m looking forward to it, it tastes so good and i picture I’m pleasing you.”
“Well you definitely deserve it today, would you thank your cousin for me first though because without her we wouldn’t have had such a nice day.”
“Of course i will.”
Passing him the phone over he realised she’d dialed her number, he was going to be speaking to her personally.
“Wait you want me to talk to her?”
“Yes sissy, now thank her for your gift.”
She picked up after just a few ring’s, disguising his voice he spoke to his cousin.
“Thank you so much for allowing me to please my owner, she will be treating me after.”
“It’s fine, I’m glad to help, it’s been fun following your post’s, i look forward to any further post’s.”
“How come you like it so much?”
“Because most guys deserve the punishment, if i ever got the chance I’d do it too.”
“Wow ok, well I’ve gotta go now.”
“Bye bye.”
James accidentally lost his disguised accent on his last sentence, he was convinced she recognised his voice.
“Good boy, time for your treat, you can watch me make it today.”
“Thanks Claire.”
She took out the container of condoms and placed them by the pussy, his face dropped. She placed the pussy between her leg’s and started to empty the first condom onto it.
“What’s that?”
“It’s your cummy treat.”
“But that’s real cum though.”
“You’ve been eating it everyday, but no glaze mixed in today, are we going to have a problem?”
“No Claire.”
“Start to eat the pussy out as i drip the rest of these onto it, your first real cum clean up without any sugar in it.”
He did as told, it didn’t taste nice at all, the last few times were ok but this was just bad, Claire recorded as much of it as she could.
“Hi Stephanie I’m calling to let you know that my sissy ate all that cum, James thank Stephanie for letting you eat her boyfriend’s cum.”
He had to thank a girl he’d only met once for eating all her boyfriend’s cum, how was he going to look her in the eyes when he saw her again? Claire had told him that once a week he’d have to pick up more condoms from her.
Everyday he didn’t think things could be worse but she kept pulling things out of her hat, not only did this hot goth know he’d done this but also his cousin most likely now knows he’s a sissy too.
Claire uploaded the cum treat video but made sure it was edited first to hide themselves, then she detailed in full how she’d fooled her sissy with glaze. It was an instant hit, and before bedtime it was seen by many, with over 20k views.
“My mother will be here soon, so i want you to make yourself scarce, you can stay in your room with a hypno video, while i catch up with her.”
“Yes Claire.”
“Put some earphones on though because i dont want my mother to hear anything.”
Hours had gone by and it was time for her mother to go, she’d told her bits about what she had been doing, but not everything, on her way out Claire told her to pop her head in to see what he was upto. All she saw were lots of big cocks on the screen with sissy captions, all flashing up in bright letter’s, she looked at the bed to see him sitting up with his headphones on, and in his hands were a dildo and vibrator, beating himself to a steady rhythm he didn’t even notice her being there.
Closing the door behind her she just looked at her daughter and shook her head.
“Does he even have a bulge?”
“Not much of one, but apparently I’ll be able to make him smaller.”
“Well don’t make him too small because he’ll need something to play with.”
“He won’t have the chance to play with it.”
“Well just be careful.”
“I will mum.”
She left James to it, no point disturbing him now, tomorrow she was back to work so she went straight to bed. James had lost all sense of time, he’d cum more than once, and was hitting his balls until the early hours of the morning.
Monday
When James woke up the following morning his groin was aching, the sensation in his nub of a penis was a dull ache, atleast the flat cage wasn’t inverted yet. Did he really want to be even less of a man than he already was. Peeling of his sticky panties, they’d nearly glued themselves to his cage. Just how much did he cum last night? He didn’t even hear Claire’s mum leave the house. She didn’t even say goodnight.
Claire on the other hand woke up feeling like she could rule the world. She went to the bathroom taking a glass with her, she filled it to the brim, that’s his morning juice. She showered herself and changed into some comfortable clothes. Work had to be done unfortunately but she had time to log into X to check any new comment’s and to see how much her property had been viewed.
“Morning James, back to maid duty I’m afraid, you’ll be showered and ready to go in 30 minutes.”
“Yes Claire, may i remove my plug?”
“You may, but once you’re all cleaned up it goes straight back in.”
“Thank you.”
“I’ve left your morning juice in there too, it’s a bit stronger today, i must be dehydrated.”
“Ok.”
“Aren’t you going to thank me for your juice?”
“Sorry, thank you so much.”
“Ok, just a small punishment for that.”
Getting on with her work she sent off emails and made many calls, the workload had gotten worse but it would only take her an hour longer than usual. She made some enquiries on home cctv and surprisingly can get an engineer out tomorrow for a quote.
James was missing his plug, he was already used to the full feeling and when it wasn’t there it just didn’t feel right. He drank Claire’s juice, no idea why as she wouldn’t know either way, but he thought that as his owner, he should respect all her wishes. He’d never get used to his maid outfit, it was just so bulky but he liked having the frilly underwear on that he’d picked out, with the slightly baggy panties on you couldn’t tell if he was a boy or girl.
She left him to his duties as she carried on with work, he’d spent an hour in the middle of the garden. He’d cleaned the house, and had cleaned all their clothes. He really was efficient at this, who’d have thought he’d find his calling in life as a maid. She told him to get ready for plapping and hypno porn, he didn’t take long to be tied and ready to go, they’d become efficient in more ways than one.
“I’ll leave you to it, make sure you enjoy it because tomorrow an engineer will be here so you might not have time.”
“Thank you for letting me know, i always enjoy my sessions.”
“Good boy, remember 2 hours of hypno, then 1 hour of your own choice.”
Once he’s finished doing that it will be time for their evening meal, she wasn’t sure yet how to punish him, it’s a pity they had ran out of cum already. Nevermind she’d be able to get more in a few day’s. She decided to set up a p.o box that way they could get some item’s more discreetly, no names needed now to send items to them, she’d just have to pick up any parcels there now.
James finished his hypno video and moved on to his normal porn now, he found out some of Riley Reid video’s, watching her embarrassing cucks was a sight to see. The joy in her face as she gets her cuck to do as she asks. He came twice before the hour was up.
“I’ve been really busy today James but i thought I’d make us food, just a chicken salad but we have fudge cake for dessert.”
” Sounds good.”
After their food had settled it was time to give him a little punishment. She told him to get undressed and find a pretty pair of panties. With him standing their ready she called her mother on facetime.
“Hi mum, just a quick call, i know you asked last night if he even had a bulge so I’ll let him show you now.”
“You’re so naughty, put him on.”
Before passing him the phone she told him that her mum knew everything now and had seen him plapping last night. Red as a tomato he took her call, showing her everything and humiliating himself further he passed the phone back to Claire.
“See mum he loves being my little sissy.”
“After seeing him today and what he has between his legs i don’t think it would actually be too bad if you did permanently damage it, it isn’t much use anyway.”
“I know mum, it’s so exciting not knowing how far i want to go, love you mum speak soon.”
Telling him to put on his new hot pants and a t-shirt they cuddled on the couch. The punishment hadn’t been too bad, thing’s could be a whole lot worse, although he didn’t like how nonchalantly that they said permanently damaging was ok. Claire began texting his cousin to put a plan in motion. Once that was all sorted she phoned Stephanie.
“Hi Stephanie i know it’s short notice but is there any chance i can get more cum for tomorrow?”
“My boyfriend is here right now, we’ve already filled a few.”
“Any chance you can fill a few more, i really need to treat my sissy?”
“I think he could go again in an hour, his ears have perked up so i think that’s a yes.”
“Thank you Stephanie.”
“I’ll bring them to work, you can collect them tomorrow, or send the sissy.”
“Great.”
“Did you like what you heard sissy, you cant wait to get more of Stephanie’s boyfriend’s cum.”
“I’ll do anything you ask.”
“Good boy, I want you to get an early night, you have errands again tomorrow.”
“Good night Claire thank you.”
She went onto X and reposted a few of the old posts, how on earth did they already have so many views. His cousin texted her, to let her know she’d done as asked, Claire couldn’t wait to see his shock.
Tuesday
Doing all the chores first thing so he’d have time for errands later, he was glad he’d be able to get out of the house for a bit, he’d get to see Stephanie again which was a bonus but picking up the condoms wasn’t too thrilling. Then claire wanted him to pick up something from a P.O box.
Waiting for the engineer to arrive Claire told James he could leave when he got here, she would show him around and tell him what she wanted.
“Ding ding ding.”
“James go get the door.”
“Hi, I’m hear to quote for home cctv.”
“Come in I’ll go get Claire.”
Claire greeted the engineer and told James to not be to long doing his errands. The engineer was in shock at how this guy had bagged a chick as good looking. She showed him around and told him she wanted a camera in every room, even the bathroom, she took him into James’s room and told him she wanted numerous camera’s in there.
“How many would you like?”
“I want atleast one in each corner because it’s where the magic happens if you know what i mean?”
“That will be no problem at all, i can fit them on Friday if you like?”
“How much does it cost first?”
“It will be between 2 to 3 thousand, I’ll price it up and email the quote for you”
“That sound’s ok.”
Seeing Stephanie again was great, he was sure she’d dressed up a bit compared to last time. She took him out back and handed him the full condoms. She held on to the last one though, with a coy look in her eye then she said.
“I’ve been enjoying all this, my boyfriend has been fucking me hard, and all i can think of his how funny it is that you’re eating it all.”
“I’m glad you’re enjoying it too.”
“I told Claire I’d got 4 full one’s for her which you’re holding, but this one i want you to eat here, just for me.”
“I’m not sure Claire would want me to.”
“Well I won’t tell, it will be just our little secret.”
“If you promise, i will.”
“I Promise.”
She placed the condom into his mouth and told him to suck the remnants of her pussy off it, he couldn’t really taste her but it was nice to know that maybe she’d want more fun. She told him to stick his tongue out and tilt his head, she poured it all onto his tongue and watched it slowly dribble down his throat.
“Good boy, you should keep the rest of those warm, pull your panties out and place them in there.”
“Ok.”
“How does sissy like his dick being so close to where my pussy has been?”
“Sissy likes it alot.”
“Good boy, I’ll see you soon hopefully.”
Leaving the shop his groin was aching, he walked carefully, afraid to pop his new gifts, they would make quite the mess. He went to get the mail from the P.O box, all he had to do was type a code into a keypad and it popped open, it was only a small package and pretty light.
They had their evening meal, watched a film together and relaxed. James wanted to know what he’d picked up from the P.O box, she wouldn’t tell him yet, just kept saying, “After.” finally after had soon become now.
“Do you want your treat in here or in the bedroom? It’s up to you.”
“I’ll have it in the bedroom.”
“You wait here while i prepare your cummy treat.”
He couldn’t wait to lick that imitation pussy again, he’d picture Stephanie though today while he ate it all. Claire opened the package and took the soiled panties out, his cousin had sent 2 pairs. She spread all 4 condoms worth of cum all over the thongs, making sure to coat the ass part too.
“Come in sissy, here’s your treat, no pussy today though just some new panties i got online.”
“Aww i was hoping I’d get the pussy but thank you so much Claire.”
She was going to enjoy this more than anything they’d done so far, it’s so taboo. She watched as his tongue licked the thong straps making sure he cleaned everything, she made him clean them over once more. She opened his mouth and placed them in there, seeing her smile made this all so worthwhile, he adored her. Taking the panties out after ten minutes it was time to chat.
ero
