Owned by the Landlady - 9 (Patreon)

Owned by the Landlady - 9

Josh - Yes ma’am

Diane had left me at home locked into the maids outfit and the heels. Of course Paige chose that moment to turn up.

I froze in the doorway to the kitchen, watching Paige’s expression shift from shock and confusion to worrying smirk. “Well, look who's all prettied up. I did wonder what Aunt Diane meant by having you help out around here.”

“This is…..” Where exactly was I supposed to start explaining this one?

“Ya know, when I saw that pic of you in the maids outfit I assumed she had tricked you into it or forced you somehow, I had no idea this is how you like to spend your days.” Said Paige.

“This isn't exactly how I choose to spend my days.” I replied, lamely.

“And yet here you are, all dolled up. What, did aunt Di physically overpower you and force those clothes onto you?” Paige asked.

“Well, not exactly….” As I ran over the explanation for my appearance in my head, I realized how crazy it sounded. “We came to an agreement, and this, umm, outfit, was a part of it. I'm just helping out around the house while I'm not working and your aunt insisted on this outfit.”

“And you just agreed to it? Agreed to dressing up like a little femme maid all day?”

“It's not all day, and….” What could I say? ‘Your aunt buys me shiny things in return for humiliating myself which turns me on for some reason.’ “....She was persuasive.”

“Hahaha I'll bet she was. She always did have a way of getting what she wants.” Paige said as I stood there blushing. “But she's not even here right now so why don't you take the outfit off? Unless you secretly love being all girly.”

“I uhhh. I can't take it off….it's locked.” I sighed.

“Paaahahahahaa, she locks you into your outfit.” Paige burst out into another round of laughter as she glanced down at my feet and saw the locking heels. “Holy shit your heels are locked too!”

“Okay, okay. You've had your laugh. Is there a reason you’re here or did you just come to make my life miserable?” I said.

“I was coming to visit my dear aunt and her lodger, duh. And she always has good stuff in the fridge.” Paige finished grabbing whatever she was grabbing from the fridge when I interrupted her and closed the door. Then she froze for a second. “I have a tiny cock….” The page from my punishment was still stuck to the damn fridge door. “Oh my god did you write this? The whole page?”

I blushed redder than I think I ever had before in my life. “Yeah….your aunt’s way of messing with me I guess.”

“Hahaha she made you write lines, like a naughty school kid? Did you have to wear a schoolgirl outfit while you did that?”

“No I didn't!” I snapped.

“Oooh does that mean you have to put that little cage back on your ‘ tiny cock’ now that I'm here?”

I really didn't want to tell her that I was already wearing it as part of my outfit. Thankfully, I was saved that part of the conversation by the front door opening and Diane returning home.

“Paige, good to see you again.” Diane greeted her niece as she joined us in the kitchen. “I hope my maid has been making you feel welcome?” She added, grinning at me.

“Diane, do you have the keys so I can get changed?” I asked.

“Oh right, of course. I suppose your shift has ended” She produced the keys from her pocket and unlocked the dress and heels. I gave a quick ‘thanks’ and disappeared from the kitchen, Paige's laughter following me upstairs. Diane hadn't mentioned the keys to the chastity cage, but I figured she would hand those back when Paige had left.

—

I stayed in my room for a while after changing out of the maids outfit, not wanting to face Paige and Diane’s teasing right away. I heard Diane call me an hour or so later, telling me that she had dinner for the three of us.

I sat next to Paige at the small dinner table with Diane sitting opposite the two of us. We made idle chit chat for a while as we ate and everything seemed like a normal, sit down dinner. That normality was disrupted when I felt Paige’s hand slide across my thigh.

I shot her a sideways glance, eyes narrowed in warning but she just grinned evilly back at me. I glanced at Diane but she was engrossed in her meal and hadn't noticed the shared looks. My cock twitched in its cage as Paige's hand slid across the material of my pants, closer and closer to my crotch. I reached my own hand down beneath the table to impede Paige's progress.

“Josh! Watch where your hands are going.” Paige cried out, drawing Diane's attention just as my hands were under the table.

“What? Me? But you were-”

“Josh, try to keep your hands to yourself while we're eating dinner please.” Diane said, causing me to place my hands back on the table, noting Paige's devilish grin as I did.

I kept my hands on the table but of course Paige did not do the same. I felt her hand return to my thigh and creep slowly towards my crotch area. I decided to try and ignore her, not give her the satisfaction of a reaction as I finished my meal.

Closer and closer her hand crept until it was resting on the fabric of my shorts, right above my caged cock which was trying to wake up thanks to the contact. Paige’s hand didn’t do much, but it was there, a constant presence making sure to keep me aroused and distracted, despite how much I pretended not to be. I knew she could feel the solid surface of the small chastity cage, her fingers lightly tapped around its contours in a maddening fashion.

“So, I was thinking I might stay for the weekend.” Paige said, glancing sideways at me.

“Of course, sweetie, you know you’re welcome here any time, and I’m sure Josh doesn’t mind, do you?” Diane replied.

“Umm, no…no of course not.” I said, while in reality we all knew that that would mean I wouldn’t be allowed out of the chastity cage until Paige decided to leave, as per Diane’s earlier rule.

“Yay! The whole weekend. Won’t that be fun?” Paige said, giving my chastity cage an insistent squeeze as she spoke.

“Can’t wait.” I grumbled, through gritted teeth.

My cock was pressing incredibly tight against the cage by the time dinner was over and I wanted nothing more than to be able to take it off. It wasn’t even like I was desperate to jerk off, but not being able to get a full erection, or any sort of erection thanks to the cage was incredibly frustrating and I know Paige knew it.

I helped clear up after dinner, relieved to finally be able to leave the table and go take a cool shower to calm myself down. I decided to spend the rest of the Friday evening playing games in my room while Diane and Paige spent time together downstairs.

I heard them both coming upstairs to bed a little later on but apparently Paige couldn’t resist paying me a visit before she went to sleep. She quietly opened my door and crept inside. Hey, Josh, how’s your little cock doing in the cage?”

“Fine. No thanks to you.” I replied, not looking away from my game.

“Ohhh right, you mean the dinner thing. Sorry about that.” She said in a voice that suggested she was not sorry in the slightest. “Just had to make sure your little pecker was safely locked away while I’m here.”

“Are you seriously staying here the whole weekend?” I asked.

“Of course I am. Hope that won’t be too ‘hard’ for you, staying all locked up all weekend.”

“Ha-ha. I’m sure I’ll survive.” I replied, although inside I was desperate for some relief.

“I’m sure you will, so tell me, panty-boy, will you be getting all dolled up in your little maid outfit tomorrow? I’d love to see you at work.”

“No, actually I don’t ‘work’ on weekends. Part of the deal.” But I couldn’t help but wonder if Diane would really insist on me donning the maids outfit if Paige was still here on Monday.

“Awww. Oh well, looks like I’ll just have to wait til Monday to see you in action.” That comment got me to look away from my game.

“Are you seriously gonna stay all weekend just to torment me?”

“Ha, you pantied ass I am. See ya later baby dick.”

I sighed loudly. “Fuck.”

—

The weekend was a blur of frustration and humiliation. Diane was her usual teasing self for the most part but Paige was insatiable, jumping on any excuse to tease me about the cage, the panties, the maids outfit. It was clear she was Diane’s favorite person in the world because Paige was never reprimanded for her teasing, at least not in any meaningful way.

Night times were the worst. Sleeping in a chastity cage was a nightmare, especially one as small as the one I was wearing. I was constantly awoken by nocturnal erections and it didn’t help that I was constantly being kept horny by the two women in the house.

I did my best to stay out of the girls' way for the most part, choosing to hang out in my room and take advantage of Diane’s purchases. But I knew there was no way to avoid the upcoming Monday.

—

Monday morning and of course Paige was still here and showing no signs of leaving. I managed to catch Diane alone in the living room before I was due to start my shift as a maid. I already knew the answer but I had to ask. “Do you really expect me to work with Paige here?”

“Of course I do. We made a deal, Josh. I've held up my end, spent my money on your stuff. Besides, it's only two hours and Paige has already seen you in your outfit….and worse.”

“Yeah, thanks to you.” I grumbled.

“No, thanks to you. You're the one who made me punish you. Now stop complaining, a maid serves the house, Paige is in the house, therefore you will show her the same respect that you show me when you're working. Now go get dressed and I'll be up to lock you in your outfit.”

“Fine.”

“Without the attitude.” Diane said as I slumped out of the room to get dressed.

Stockings, panties, the stupid locking dress and heels. Check, check, double check. Diane entered my room and smiled when she saw me. “There she is. Let's get you all locked up.” The back of the maid dress was locked, followed by the heels and I was ready to face what I knew would be a more embarrassing shift than usual.

“Okay, let's get this over with.” I said.

“That's the spirit, sissy. Don't worry, you'll be fine. And when it's over you can take the chastity cage off and go play with your little penis.” Said Diane. I wish I could have contradicted her statement.

Paige was waiting downstairs in the living room when I walked carefully down in the heels. Her reaction was as expected.

“Awwww look at the sissy maid all ready for work!” She said in a high pitched, condescending voice.

“Shut up!” I snapped.

“Ahem!” Diane didn't sound pleased. “What did I tell you about showing proper respect?”

“Right, sorry.” I muttered.

“That's one punishment earned already and you've barely started your shift.” Said Diane, much to Paige's delight.

“Ohhh, naughty maid.” Said Paige. “So, what does he, sorry, she usually do whilst ‘working’?”

“Whatever I need, really. Cleaning and tidying mostly, unless I have any other special requests. He's here to help.” Diane answered, turning to me to add, “isn't that right, maid.”

“Yes Miss Ryan.” I replied.

“Oooh I've never been in a house with an actual maid before. This could be fun.” Paige flopped dramatically back onto the sofa and kicked her bare feet up onto the armrest. “Okay, maid, bring me a nice cold glass of orange juice. Chop chop.” She was really making a meal of this, but I stopped myself from saying anything snarky, one punishment was enough.

“Why thank you, sissy.” Paige said as I set down the drink on the table near her. Diane had disappeared upstairs to get a little work done, leaving me to clean up downstairs and no doubt be tortured by her niece.

“You're welcome, ma'am.” I replied, putting as much sarcasm into my voice as I could.

“Haha this is great. Go ahead, maid, get back to work. Haha.”

I busied myself wiping down some surfaces in the kitchen, an excuse to stay out of Paige's territory while she lounged on the sofa. But I didn't get much of a reprieve as she called me back after a short while. “Oh maaaaiid I need you.”

I sighed and headed back into the living room, the heels clicking loudly across the kitchen and hallway floors. “Yes?”

“Think you could give my feet a little rub for me?” She asked, wiggling her toes on the sofa arm.

“Not a chance, rub your own dirty feet!” I replied before I had a chance to think about any potential consequences.

“Tut, bad girl.” Paige said, before calling out loudly. “HEY, AUNT DI!”

I heard Diane's footsteps heading towards the stairs. “Shit. Paige, don't!” I begged, hoping she wouldn't rat me out.

“What is it, dear?” Diane asked, stepping into the room.

“I just asked the maid nicely to give me a little footrub and she flat out refused….AND she insulted me in the process.” Paige said, laying on a very fake attitude.

“Is this true?” Diane asked me.

“Well….it's not totally untrue.” I replied.

“So that's two punishments you have waiting for you later. It's like you're trying to get punished.” Said Diane, taking a seat in the living room.

“I'm intrigued to know what kind of punishments.” Said Paige. “Is it another spanking because I enjoyed the last one?”

“It could be, we have to let the wheel decide.” Replied Diane.

“The wheel?”

“Just a fun little idea we came up with to help keep things fresh.” Replied Diane. “I'll explain while Josh here does what you asked.

I begrudgingly stepped to the foot of the couch, next to Paige's feet and reached out with both hands to begin massaging one of her feet. “I think it would be better if you did that on your knees, give you a better view.”

“Of course, ma'am.” I replied, dropping down to my knees so that I was now eye-level with her bare soles.

I gently massaged Paige's feet while Diane filled her in on the concept of the punishment wheel. The two girls chatted as though I wasn't even there for a while. The whole time I knelt at Paige's feet and gently massaged them while my trapped cock betrayed me and kept trying to get hard in the small cage.

When they were finished Paige looked over at me, still kneeling. “That was great, maid. Good job. Buuuut you did insult my feet earlier, so I think you should give them a little kiss to apologize, don't you?”

I almost refused, but the look Diane was giving me told me it would be unwise to do so. “Of course.” I said, leaning in and planting a quick kiss on each of her bare soles.

“Good girl.” Paige said, sending an annoying thrill through me. Something about the praise and the humiliating use of the feminine pronoun seemed to spark something in me.

An hour later and it was finally coming up to the end of my shift, with Diane back in the vicinity Paige seemed to lay off a little. Although she did seem to take pride in pointing out my panties whenever I bent over.

“Okay, it's one o'clock, I'm done for the day.” I said.

“Awww, already?” Said Paige.

“Unfortunately, he's right two hours a day is all I get….for now.” Replied Diane. “But before I let you out of your uniform, we need to sort out what punishments you're going to get.

The three of us headed upstairs to where the wheel of punishments was, still on display in Diane's room. Paige took great delight in reading out the potential punishments I could earn before saying. “Woah! ‘Josh licks Diane's pussy’. Ew, seriously Aunt Di?” Paige said, laughing.

“Hahaha yes, he was quite eager to land on that one last time. Even spun the wheel and extra time to get it. Speaking of which, would you like to put anything else in your ‘prize spot’?” Asked Diane.

“Umm, yeah, actually I think I want something else.” I replied, though I was struggling to think of what. But after the weekend of torment, I had a pretty good idea and was feeling pretty bold. “How about, Diane goes down on Josh.” I said.

“Oooh look who's feeling daring.” Replied Diane.

“Ha, you're not actually gonna put that on there are you?” Asked Paige.

“Why not? He did it for me. Besides, with that little penis it's not like I'm going to choke or anything, haha.” Both the girls broke out in laughter at that comment while I was left embarrassed and horny. “Here, I’ll add it to the wheel.” Diane took the marker and replaced the pussy licking option with, ‘Diane sucks Josh’s tiny dick’. “There, best of luck, sissy.” Of course she would word it like that. “Paige, would you like to do the honors?”

“Hell yeah I would!” Paige stepped up to the wheel and gave it a harsh spin and I watched the options become a blur.

Time moved slowly as each of the options spun around the wheel. The extra forty eight hours in chastity was still there, so was the spanking and the ‘getting my nails done’, the prize section and of course the option that would let Diane add to my uniform.

The click, click, click of the wheel slowed to a stop and my heart sank. ‘Forty eight hours in chastity.’ “No!” I cried in despair. I had already been in the cage since Friday morning thanks to Paige turning up, now I would be stuck in the cage until Wednesday afternoon. “Come on, Diane, please. Can I get a do over or something?” I begged.

“Sorry, sissy. Rules are rules. I wouldn’t be asking for a do over if it had landed on your prize spot. Now you still have one more punishment. Paige?”

“Coming right up!” Paige spun the wheel again as I watched on in despair, my cock seemed to see the result of the first spin and try its best to break out of the cage by itself.

I watched as the wheel slowed to a stop once again, this time landing on the space marked ‘Josh gets his nails done’. “Great.”

“Oohh I can’t wait to see you with your nails all prettied up next time I come over.” Said Paige.

“Looks like I’m booking you an appointment at the salon for tomorrow.” Diane added.

“What? A salon? You expect me to go to a salon!” I said.

“Well, yeah, how else would you get your nails done?” Replied Diane.

“I dunno, I guess I thought it meant that you would just paint them yourself here.” I replied.

“Oh no. I could never do a good enough job. You’ll get the professional treatment, no expense spared.” I should have known….

—

The appointment was made for early on Tuesday morning. Diane told me this was a kindness as she didn’t expect the salon to be busy at that time. I was dressed in some jeans and a t-shirt as Diane and I headed to the salon, a pair of blue panties with laced edges underneath and I hoped no one at the salon would see them. It was bad enough I would be letting them paint my damn nails.

“Cheer up, Josh, the girls here are very professional, they’ll take good care of you.” Diane said as she drove us both to the salon.

“Yeah, I’m sure they will.” I replied, glumly.

“Aww is someone a little frustrated because they haven’t been able to pay with their little babydick for a while?” Diane said, giggling. I hated that the mere mention of my cock caused it to twitch in the cage now. Even more so thanks to Diane’s constant teasing about my size.

As Diane expected, the salon had no other customers when we entered and the girl who greeted us didn’t question a guy coming in to get his nails done. They all greeted Diane like an old friend and chatted happily while I stood there wishing I was invisible.

One of the salon girls eventually led me over to a table and sat me down opposite her. Diane stood behind me and watched over my shoulder as the work started on my nails. They were filed down and smoothed out to start with which I guess I expected. What I didn’t expect was the pink acrylics that were laid out next to my hands. “Diane, aren’t those a little much?” I said.

“Relax, Josh, you’re gonna look great.” Diane said, one hand rubbing my shoulder affectionately.

“First time getting your nails done, sweetie?” The salon girl asked.

“Yeah. And hopefully the last.” I replied.

“Oh we’ll see. You’re gonna love these when we’re through.”

‘We’ll see about that.’ I thought to myself.

“Oh! Careful, Josh, your panties are showing.” Diane said, pulling my shirt down at the back.

I instantly blushed a deep red color, stunned that Diane would humiliate me in public like that. I could have sworn I saw the corners of the salon girl's mouth twitch. “Don’t worry, Josh, we get all sorts of people here. You’re fine.” I said nothing.

The pink acrylic nails were affixed to my fingers and my hands were placed under a glowing thing that was supposed to seal them. When that was finished I was left with a full set of hot pink nails that extended past the tips of my fingers. “Okay, now we just need to fix up your toes and you’ll be good to go.”

“My toes?”

It was Diane who answered. “Of course, Josh. You need pretty toes to match your fingers. Besides, they’ll look great under stockings later.” I was wishing the floor would open up and swallow me at that point. Unfortunately, the floor remained intact and I was not spared the embarrassment of having my toes filed, clipped and painted by the salon girls.

Diane was standing at the other side of the store, talking to one of the other workers as the girl finished working on my toes. She looked up at me and spoke in a quiet voice. “So, how long have you known Diane?”

“Oh erm, a couple of weeks. I took a job nearby and she had the best deal on a houseshare.” I replied.

“Haha, I’ll bet she did.” That sounded a little conspiratorial.

“What does that mean?”

“Oh nothing, nothing. I’m sure you’re going to have lots of fun staying with Diane….” Then she gave a small wink up at me. “...Sissy.” My eyes widened, she knew. She knew what Diane was doing to me, had she done this before? Did Diane just take guys and turn them into sissy servants for her amusement? Would that make me want to run if it were true? “All done.”

I looked down to see the pink toes that now matched my fingernails and the only thing I could think to say was “....Thanks.”

“No problem. Just have Diane bring you back down if you need an infill or anything else.” She replied.

“I’ll be sure to do that.” Diane replied, appearing back behind me. “Thanks, Georgia, they look great. Ready to go, Josh?”

“Yeah.” I put on my shoes and socks, hiding the pink toes from view and followed Diane out of the store.

“Hmm, looks like you’re gonna be a little late for the start of today’s shift.” Diane said as we approached her house. “But I think we can let you off with the missing time for today.”

“Gee, thanks.” I replied.

“Hahaha, such a fussy, sissy today. Don’t worry, I just have a few simple training things to run through with you today…”

Diane didn't elaborate further until we got home and I was sent to get dressed. I noted how the pink toenails shone through the sheer stockings as I pulled them onto my feet and the new nails somehow made my hands and forearms look more feminine than they did before. When I was dressed and ready, I met Diane in her bedroom.

“Okay, sissy. I noticed yesterday that you were pretty lax on your curtsying whenever you were given an order. You're lucky I didn't add another punishment on but I figured two was enough. But today, I'm going to start drilling it into you to make sure you remember to curtsy when you're supposed to. Understood?”

“Yes ma'am…” I replied, a little uncertainly.

“Good, I'm going to ask you some questions now and all you have to do is answer ‘yes ma'am’ or ‘yes miss Ryan’ and curtsy right after. Got it?”

“Yes ma'am.” I replied. Diane shot me a stern look and I realized what she wanted. “Shit, sorry. Yes ma'am.” I said again, this time curtsying.

“Better. Now, are you going to remember to be a good sissy maid from now on?” She asked.

I ignored the embarrassment I felt at answering and replied. “Yes ma'am.” Dipping into a curtsy.

“Okay, good. Are you happy with our arrangement so far?”

I wasn’t sure if she was actually giving me a chance to say no, but despite everything that had happened so far, I was mostly happy with everything that had happened. “Yes, ma’am.” I said, curtsying again.

“Do you like being my maid?”

“Yes, ma’am.” I curtsied again, sensing what the pattern of these questions and this exercise would be.

“Do you love being a sissy maid?” She had a wide smile on her face when she asked that one.

I paused for a half a beat, but carried on following her instructions. “Yes, ma’am.”

The next question caught me off guard a little. “Do you have a tiny penis?”

“Yes, ma’am.” I curtsied, blushing a little.

“Haha, I knew it. Do you like having your little cock locked away in a tiny little chastity cage?”

“Yes, ma’am.” I answered, more begrudgingly this time, but still curtsying.

On and on the questions came, getting faster and faster until my responses became automatic. “Yes, ma’am.” Followed by a dainty curtsy. It was clear what her plan was, engrain the response and the curtsy into me so deeply that it became an almost automatic response.

“Do you like wearing panties all the time?”

“Yes, ma’am.”

“Do you love it when I play with your sissy ass?”

“Yes, ma’am.”

“Do you love being teased about your little sissy girl-cock?”

“Yes, ma’am.” My responses may have been automatic, but I was still embarrassed to be agreeing to everything she said and it was clear that Diane was enjoying my discomfort immensely.

Her smile kept getting wider. “Would you like to eat my pussy again?”

“Yes, ma’am.” I was more enthusiastic with that answer.

“I’ll bet you would. Would you like me to fuck your sissy butt again?”

“Yes, ma’am.”

“Hahaha, I thought so. Do you love it when I embarrass you?”

“Yes, ma’am.”

“Are you a sissy slut for me?”

“Yes, ma’am.”

Diane kept firing the questions at me and I kept answering and curtsying until she ran out of embarrassing questions to ask me. I spent the rest of that maid shift walking around in the heels with Diane directing me on how to place my feet and how to bend at the waist etc. At one o'clock my training was deemed to be complete and I was allowed to get changed, but still with twenty four hours left on my chastity sentence.

“I’ll bet you're desperate to get out of that cage by now, huh, sissy.” Diane said as she unlocked my outfit.

“Yup. Just twenty four more hours.” I answered.

“One more day to go….That is if you don’t get any more punishments during tomorrow’s shift.” Replied Diane.

“Shit, I didn’t think about that.” I said, “I guess I’ll have to be on my best behaviour then.”

“Haha, I guess so. It would be just terrible if you rolled another chastity sentence tomorrow. I guess you’d better not disappoint meeee.” Diane ended with a sing-song voice as she left me to get dressed.

I had a feeling tomorrow was going to be a difficult shift.

End.