Owned by the Landlady - Part 3 (Patreon)

Owned by the Landlady - 3

Josh - I will NOT put on that outfit

Two days I had spent in the chastity cage, my punishment for what happened between me and Diane’s niece, Paige. I was currently stood with my hands in the sink, washing the dishes at Diane’s ‘request’, while she watched from the kitchen table.

“You do make a good maid, Josh. Sure I can’t tempt you to put on that outfit?” Diane asked from behind me.

“No thanks.” I replied, quickly.

“What if I told you I’d take off your cage if you put it on?” 

“You already promised to take it off after I finished all the chores for today.” I reminded her of the deal she had made after I nagged her about the cage this morning.

“Oh right, guess I should have held out a little longer, cashed in my bargaining chip too early, ha.”

“Guess you did. Anyway, that’s everything done for the day. I held up my end, now you hold up yours.” I said, turning to face Diane.

She sighed before answering. “Fine, a deal’s a deal. Here’s your key. Try to stay out of trouble this time.” She said, handing me the small key that would free my cock. A key I couldn’t wait to use.

“And what about…the underwear?” I asked.

“The panties you mean? They’re staying. I told you, you lost male underwear privileges. Now go, free that little dicky of yours from its prison, haha.” 

“Shut up!” I snapped, objecting to her insults to my size while ignoring the reaction her words got from my cock itself. Diane just walked away, giggling to herself.

I was more than ready to give myself a little relief after the last two days. I don’t know if it was because I was extra horny being stuck in panties and a chastity cage but I could have sworn Diane had started to dress a little sexier. The yoga pants/tight leggings she had caught me staring at before were now a constant fixture in her daily outfits,  usually paired with low cut tops or loose shirts with no bra underneath. Not to mention the ‘panty checks’ Diane had taken to performing from time to time. 

I quickly retired to my room for the night and felt my cock become instantly hard inside the yellow panties I was wearing. I tried to tell myself that the underwear had nothing to do with it, that it was all because I had been locked up for a few days why I was so quick to become erect….

—

The next couple of days passed without incident, even though Diane never really let up with her teasing, I managed to stay on her good/not kinky side. I caught her struggling to move some small shelves while she cleaned her living room one afternoon. I was incredibly bored without work to keep me occupied and had exhausted most of my streaming options.

“Need some help?” I asked, after taking a second to stare at her ass, the black leggings were stretched tight across her cheeks as she bent over to run a small vacuum under the shelves. 

“Yes! Please, it’s impossible to move these things on the carpet, can’t slide em. Would you mind?”

“No problem.” I grabbed the shelving unit she was working on and carefully shuffle-walked it a few inches back so Diane could reach underneath it. “Need anything else?”

“Yeah, would you mind grabbing that duster and running it over the top of the shelves and the TV?” Diane said, pointing to a small, feather duster she had.

“Do these things actually work?” I said, waving the duster around.

“Course they do, they’re designed to trap dust and cobwebs and stuff.” Diane replied.

“Hmm, fair enough.” I ran the duster over her fireplace and the photoframes she had on there, noticing how the feather duster did, in fact, work.

I heard Diane make a sort of contemplative noise behind me and I knew what she was thinking. “Don’t say it.” I said.

“Why not? You’re already doing the maids work, may as well wear the outfit.”

“I am not wearing that outfit.” I replied, still running the duster across the top of shelves and tables.

“What if I make you a deal?” Said Diane.

“A deal?” This was a new approach.

“Sure, you’ve been wanting a new TV for your room, right? I’ll pay for it in exchange for you wearing the maid outfit.”

I should have immediately said no, but I answered without thinking. “For how long?”

“An hour a day.” She replied.

I stopped dusting and turned to face her. She was watching me intently and I think she had sensed a small weakness in my armor. “Every day?”

“Five days a week, weekends off, of course.”

“You’re serious? You really want me to wear that thing so bad?”

“I do, I think it would be far more entertaining than anything else that happens around here.” Diane replied.

“Forget it. I told you, I’m not wearing it.” I said, trying to sound final.

“But you were interested for a second there. So what’s it gonna take? Go on, name your price.” Said Diane.

I thought for a second, the last week or so had been incredibly boring. I only had a few odds and ends to deal with for work, working remotely from my bedroom whenever I got an email or phone call, the rest of my free time was spent obsessing over Diane’s kinky side and wondering what might happen next. Maybe I could use this to my advantage. “A TV, and a new games console.”

“Done!” Diane answered way too quickly, she didn’t ask how much or which console I wanted, she just agreed right away.

“Wait, seriously?”

“Sure, send me a link to what you want and I’ll get them delivered….for two hours a day.”

“You said one before!” I whined.

“That was before you added the computer thing. Maid work, full uniform, two hours a day. Do we have a deal?” Diane held out her hand to seal the deal.

I thought about it for a long while. A new games console, whichever one I wanted and a TV to play it on….with very little money of my own this was my best shot at getting something of my own. “Okay, deal.” I shook her hand.

Diane didn’t release her grip, instead she grabbed my hand tighter and pulled us both close together. I met her gaze as she spoke in a low voice. “I knew you wouldn’t be able to resist.”

“I’m just doing it for the TV.” I replied, but I could tell she didn’t believe me.

“You keep telling yourself that, sissy.” Diane reached down to make her point by snapping the waistband of the panties that had ridden up above my pants. 

Shit. What had I done? 

—

“Okay, Josh. I’ve decided that you can work as my maid from eleven til one, that okay with you?” Diane asked the next day.

“Fine, I guess.” I replied. I had just finished setting up my new gaming station. UHD 4k TV and I had added an extended 1TB of storage to my new games console, Diane hadn’t commented at all on how I had just spent over a thousand dollars of her money. I guess she really wanted to get me into that outfit.

“Then come along, maid. I’ll help you get dressed this first time.” I followed Diane up to her bedroom where I saw the outfit waiting for me, laid out neatly on the bed, taunting me. “Strip.”

I thought about objecting but it would be pointless, she had already seen my cock more than once, I was just worried about what humiliating comments she would make this time. Naturally, she didn’t disappoint.

“Aww, there’s the little guy.” She said in a cutesy voice as she eyed my cock in the panties.

“Shut it!” Came my predetermined response to such comments.

“No. Arms up.” Diane dropped the dress down over my head, black fabric with stitched on white apron, it came all the way up to my neck and a collar fastened around the back. I noticed the collar was made of a stiffer material than the rest of the outfit. The skirt was much shorter than I would have liked with built-in petticoats that kept it sticking out a little, exposing more of my thighs. I hated the fact that I was so turned on by this moment, I told myself the erection was due to Diane’s proximity and the hungry look in her eye. “Sit on the bed, I’ll help you with these.”

‘These’ turned out to be a pair of white stockings which she rolled up into tight circles before rolling them up my legs one at a time. The stockings hid most of my leg hair from view but a few strays poked through the thin material. 

“You really need to shave your legs for the look to work.” She mused.

“That wasn’t part of the deal.” I said, swallowing a lump in my throat at the tension in the air, the feeling of Diane’s hands rubbing my stockinged legs wasn’t helping with the erection.

“No, I guess not. But your very little friend seems to like the idea.” 

“Fuck off.” I replied.

“Hahaha, such language is so unbecoming of such a pretty girl.” 

“I am not a girl.”

“With a cute little clit like that, could’ve fooled me.” She retorted quickly.

“Would you please stop that?!” 

“I will if you stop getting hard when I do it, short-stuff.”

“Fuck you.”

“Tut, tut. Bad girl.” Dammit, another twitch from my cock. “Now, here, turn around.”

I turned and Felt Diane doing something with the collar at the back of my neck as it tightened lightly. Followed by a quiet ‘click’.

“Hey, what the-” My hand shot behind my neck and I felt a small padlock that had been snapped shut, the hasp ran through the hole in the zipper and a stiff ring of leather attached to the collar. I was locked in the dress!

“Don’t panic, I’ll unlock the dress at the end of your shift, you’re getting off lightly with two hours. Now put on the shoes.” The shoes were black, shiny enamel flats with a buckle at the side. 

“You could have warned me at least.” I said as I fastened the shoes.

“And miss your little hissy fit?” Diane chuckled. “Now, you’re late for your shift, but I’ll let it slide as it’s your first day.” Diane slapped me on my partially exposed ass. “Now get to work, sissy.”

“Don’t call me that.” I said, noticing the irony of objecting while dressed as I was.

“Haha, what else would I call a boy who gets turned on by women's clothes?”

“I’m not turned on by women’s clothes.”

“Oh, so why are you still rock hard in your little panties? Is it me? You’re not having impure thoughts about your landlady, are you?”

I blushed as I realized that any answer I gave would only have made things worse for me. “Let's just get this over with.” I said. 

Diane led me downstairs and told me that I would be cleaning the kitchen today. “Just work on the tiles and countertops today. They haven't had a good scrub down in a while. I'll get started on your training properly tomorrow.”

“Training?” 

“Of course. I need my maid to behave accordingly.” She smiled.

“You're really going to milk this, aren't you?” I said as I started wiping down the kitchen.

“Of course I am. And do you know why?” She asked.

“Yeah, cause you get some sort of weird thrill at seeing me humiliated.” I grumbled.

“I do, actually. I just get soooo hot seeing a guy humiliated by me, for me, because of me. It turns me on, so what does that make you?” She asked, following closely behind me as I did a very distracted job of cleaning down the counter tops.

“What do you mean?”

“Well, you said you would never wear that dress, but all it took was a few shiny things and here you are, locked into the dress. Your dignity had a price, so what does that make you? Are you my sugar baby?”

“N-no.” I replied, but by all definitions, that’s pretty much exactly what I was. I gave it up for a couple of gifts…but hey, I had over a thousand dollars worth of new stuff in my room.

“Hahaha, sure you are. So keep working my little sugar baby. Don’t forget to do the cupboards under the sink.”

“Ugh, fine.” I tried to ignore her and opened up the lower cupboards. I felt movement behind me before being met with a stinging slap to my ass. “Ow! Shit, Diane.” I turned to see her standing there holding up a spatula which she had just used to spank me.

“First of all, while you’re dressed like this, it’s ‘Miss Ryan’.” She said, brandishing the weaponized spatula. “Secondly, you need to bend at the waist. It’s more professional.”

“Professional? You mean it will show half my ass and embarrass me more?” I replied, rubbing the spot where the spatula had hit me.

“That too. Keep going.” I shot her an annoyed look and turned back to wipe down the shelves inside the cupboards, remembering to bend at the waist and feeling Diane’s eyes on my ass. “Much better, now everyone can see your pretty panties when you bend over.”

I blushed deeply as my cock throbbed inside the lace panties. As I straightened up and turned around I saw Diane eyeing my crotch. “Ugh, we need to get rid of that little thing while you work, it’s a little distracting. I think I’ll add the chastity cage to your outfit during your working hours.

“What? Why?”

“Because I don’t want my maid to have an erection. Even if it isn’t much of one.”

“Would you stop with that?!” Diane answered by swinging the spatula at my exposed upper thigh.

“That’s ‘would you stop that, Miss Ryan’.” She said, smirking. “Put the cage on before the start of your shift tomorrow. Or I can add something much more fun to your uniform.”

What else could I say except “Yes Miss Ryan.”

Diane followed me around for the rest of my ‘shift’ making sure I bent at the waist whenever I needed to reach down for something. It was clear that today wasn’t about me doing any actual cleaning, but an excuse for Diane to correct me with her spatula whenever she had the opportunity. I swear my cock never actually lost its erection the whole time.

“Okay, it’s one o’clock, I’m done.” I said, straightening up.

“Wow, one already. Time really does fly when you’re having fun. Okay, I guess you’re done for the day. But don’t forget to lock up that babydick before eleven tomorrow.” Diane couldn’t resist one last dig at my size and I lamented once more about how it actually turned me on.

—

The following day, right before my shift was due to start found me locking the chastity cage in place, reminding myself that it was only for two hours. Diane had left the outfit and stockings in my room for me so I could get dressed myself. It hung on the back of my door, taunting me as soon as I woke up.

I pulled on the dress and fastened the stiff collar behind my neck before heading out into the hallway. Unsurprisingly, Diane was standing outside my room, waiting for me, making a show of checking her watch.

“Right on time, good girl.” 

“Shut up.”

“Ah-ah, is that any way to address your boss for the next two hours?” She said, grinning.

“Ugh, fine. Sorry ‘Miss Ryan’.” I tried to sound as sarcastic as possible.

“That’s better.” Diane held up the small padlock that would trap me in the dress for the next two hours. “Turn around.” Diane quickly locked the dress in place and asked me for the keys to my chastity cage.

“Thank you. You’ll get these keys back at the end of your shift.” Diane gave me an exaggerated evil grin before adding, “If you behave…..”

‘Slap’ “Oww, shit.” I yelped as Diane’s paddle came down on my ass.

“Bend at the waist. Keep your back straight.” Diane had me move ornaments and books around in her living room, again I wasn’t doing much tidying or cleaning, she was merely using a small paddle to swat me whenever I did anything wrong. 

As I neared the end of today’s two hours, Diane had one more bit of ‘training’ for me. “Not bad today, sissy. I think you’re ready to learn how to curtsy.”

“What? You mean that girly, swishy bow that women did in the fifties or something?” I said, shocked.

“Exactly that. It’s a staple of a good maid. It shows difference and respect for the master of the house. In this case, me.”

“Come on, Di-err, Miss Ryan. Have you not had enough fun tormenting me already?”

“Nowhere near. When you agreed to being my maid, you agreed to actually acting the part. Not just swishing around in the dress you love so much.” Diane admonished my objection. “So have your little hissy fit later. It’s easy to do, look. One foot behind the other, bend the knees slightly and bow your head while lifting the hem of your skirt.” Diane gave a quick demonstration, mimicking the skirt lift as she was currently wearing the tight leggings that always caught my eye.

I sighed and copied her movements, feeling ridiculous as I did.

‘Slap!’ “Thumb and forefinger for the skirt. And don’t rush it so much.” I tried a few more curtsies under Diane’s watchful eye until I saw her wall clock hit one PM.

“That’s it. Quittin time.” I said happily.

“Okay, okay. But I want you to try and get the curtsy right, practice a little tonight. I want my maid to be perfect. I can’t be expected to babysit you every shift.”

“Got it. Can I have those keys back now?” I held out my hand for the keys that would free me from the outfit and the cage. Diane didn’t object as she handed them over.

—

The next shift was more of the same, more curtsying, bending at the waist, standing with my back perfectly straight, hands clasped together in front of me and a way too happy Diane waving her leather paddle at me.

That evening, I decided to join Diane for dinner, I didn’t always as her schedule was sporadic at the best of times and I ate quick, easy meals. I offered to help clean up after we had eaten.

“Just can’t resist the maid's work, can you?” Diane teased from behind me. “I don’t mind waiting if you wanna go throw on your outfit.

“I’m good.” I said, dryly.

“Aww, spoilsport.” 

“Two hours a day, that’s all you get.”

“We can always negotiate your hours.” Diane replied.

“Ha, no thanks. I already feel like I should have pushed for more in this deal.” I replied as I dried my hands.

“Don’t act like you don’t love it too. That little cock of yours was hard the whole time on your first day. At least, I think it was hard, it was big enough that it almost looked like an actual cock.”

I hit back with my own retort without thinking. “It was big enough for your niece.”

I may have fucked up. I saw Diane’s usually playful and mischievous demeanor slip for a second before she masked it with a smile that didn’t quite reach her eyes. “Oh, Josh. You’re going to regret that.” I swallowed audibly.

“For someone who spends all day torturing me you sure are sensitive when someone bites back.” I replied before quickly taking my leave. 

—

I felt a little bad about my comeback with Diane, but a part of me was happy I had managed to get to her a little. She didn’t immediately come for her revenge though, which should have made me worried. As it happened though, I didn’t see her payback coming…

My last shift for the week was just about to wrap up, I had been watching the clock for the last ten minutes as I made a show of picking up a bunch of random stuff off the floor, stuff that Diane had placed there deliberately to teach me about bending at the waist.

“Okay, maid. You're not doing too bad, have a seat.” Diane placed a wooden, high backed chair in the middle of the room. I was grateful for the rest, all the bending at the waist was straining my back a little. “Give me your hands…” She guided my arms behind me and before I could realize that this wasn't another training exercise, they were handcuffed to the chair, fixing me in place.

“Hey, what gives?”

“Relax, give me a minute.” Diane grabbed a rope that she had hidden somewhere in preparation. She wrapped one end of the rope around my thigh before running it down beneath the chair, looping it around the chair legs, then tying the other end to my other thigh, just above the white stockings. The effect of the ropes meant that I couldn't close my legs as the rope was taught beneath the chair.

I felt incredibly exposed, cuffed to the chair with my thighs held open and my panties on display. “Is this training? Cause it's almost one o'clock.”

“Hahahaha, training, no this is something else.” Diane said, smiling down at me. 

“Okay…so what is it?” I asked, nervous.

Her reply had me even more worried. “Revenge.”

“Revenge…You mean for that thing last night?” I asked, knowing the answer.

“Obviously.” Diane surprised me by lowering my panties and unlocking the chastity cage. She pulled the pieces from my cock and allowed it to quickly become hard. “There it is. There’s the cock that you said my niece loved so much.” There was a sinister edge to her voice.

“That wasn’t exactly what I said, it was just a stupid joke, meant to annoy you.”

“Well, mission accomplished. I’ll be back, don’t go anywhere, hahaha.”

I waited for a minute for Diane to return and immediately noticed the two ice packs she had, one in each hand. “Let’s see how impressive it is after this.”

“Shit. No, wait-Ahhhh fuck…that’s fucking cold!!” I protested and squirmed on the chair, jerking my body as far side to side as I could to avoid the freezing sensation. Diane had sandwiched my package between the two freezing cold ice packs, taking my breath away and killing off my erection quickly. “Fuuuck, fuck, fuck.”

Diane did not remove the ice packs, her hands following my cock, keeping up her freezing assault until I felt my package become numb. “When she was finished, she straightened back up with a satisfied smirk. A smirk which quickly turned into a loud laugh. “Pahahahaaaa. Wow. Not very impressive now, is it?” 

I couldn’t bear to look down and see the results of her work, knowing exactly how small shrivelled I would be thanks to her ice packs. “Hahahaha, I just have to get a picture of this.” Diane took out her phone and pointed the camera towards me.

“Diane, don’t. Come on, please.” I tried to squeeze my legs closer together to hide my poor, frozen cock from view, but the ropes held firm.

“Ah-ah, you’re still dressed up, it’s Miss Ryan now.” 

I could have argued that it was now after one o’clock, but it was not the time. “Right, sorry, please, Miss Ryan. I’m sorry about what I said.”

“Yeah, now you are. But I want to know what Paige thinks of your little babydick now.” 

“What do you mean? You can’t show her that!” I said in shock.

“Fine,” she pointed her phone at me and I heard the telltale ‘ping’ that told me she was recording a video, “just say ‘I’m a little sissy with a little sissy cock’ and I’ll think about not sending a photo to Paige.”

“Fuck you!” 

“Fine, then I'll send her a photo. Let Paige see the real you, I wonder if she’ll laugh the next time she sees you.”

“Stop it.” My cock, my traitorous fucking cock twitched at the thought of Paige humiliating and teasing me as Diane had been doing.

“Are you actually trying to get hard? Even while you’re all frozen and shrimpy.” 

“No!” I said, avoiding her gaze.

“Yes you are. You want me to send this to Paige.” She said, her eyes brightening.

“No! I don’t.” 

“Then prove it, say what I told you to say. Say it for the camera. Admit that you’re a sissy with a little sissy cock.”

“Grrr. Never!” I rattled my cuffs and pulled on the ropes, but I didn’t budge.

“Fine, have it your way. Aaaaand,” Diane turned the phone to face me, a conversation with Paige was open and a photo of me was attached, french maids outfit, legs spread, panties pulled down and tiny, shrunken cock. “Aaaand, send.” I watched in horror as she hit send.

“Nooooo!” What had I done? I refused to say the stupid, humiliating phrase that could have saved me and now Paige was going to see that photo, and what would she say? HOw would she react? Why did I let this happen….and why was I still trying to get hard?

“Hahahaha. I hope she sees this soon, I’m just dying to hear what she has to say. Should I ask her to come over again this weekend? What do you think she’ll say if she does? Do you think she’ll sneak into your room again?” Diane mused out loud, watching my cock for its reaction…and react it did.

The chilling effect was wearing off and I was starting to become erect again. I think it was almost time to admit to myself that I had a fetish for humiliation.

“Oh! She’s typing a reply.” Diane said, watching her phone intently…. “Oh, hahahahha.”

“What? What did she say?” I asked, heart pounding at what might come. 

“Ohhhh nothing you need to worry about. You can ask her yourself tomorrow. She’s going to stay over again.” 

Okay, I may have bitten off more than I could chew this time….

End Chapter 3.