Owned by the Landlady - 8 (Patreon)

Owned by the Landlady - 8

Josh - forming a gambling habit

The next couple of days passed without any new incidents, I was reminded of my status in the house every morning when I saw the tan lines in the bathroom mirror, now that the rest of my skin color had settled they looked more prominent than ever. I figured I should try to even them out if I could while the weather was still nice, but that would mean sunbathing with the tan lines on display for anyone to see.

I reported for ‘work’ as usual, dressed in the humiliating outfit with Diane teasing me and giving me pointers on how to behave, all the while making sure that my cock stayed hard in the tiny chastity cage it was stuffed into. I managed to make it through a couple of days without any further punishments from Diane and her roulette style wheel.

On Thursday afternoon, at the end of my shift, Diane decided that my work was a little too sloppy and I needed to take more care. “Josh, I think you’ve been a little lazy with today’s work. You didn’t move any ornaments when you dusted them so there’s still dirt behind and around them, your panty was neat but not organised as well as it should be, there was a thong on top of your briefs and you haven’t even gotten around to the dishes in the sink yet.” I listened as Diane listed off my apparent failures.

Truth be told, after the last couple of incident free days, I was starting to feel a little bored with the whole arrangement. I couldn’t believe I was actually thinking that….I was bored while dressed as a maid and serving my hot landlady. But the fact is, aside from Diane’s teasing, the work itself was mundane and repetitive. 

“Is something wrong? Are you distracted? Did you not stroke your little cock last night or something?” Diane asked with a smirk.

I blushed a little but didn’t answer her question. Mostly because I had, in fact, stroked my little cock last night, as I always did after a day of teasing from her. “It’s not that. It’s just the work itself is a little…boring.”

“Boring?”

“Yeah, I mean aside from the humiliating outfit and the chastity cage, the work is boring. I’m just cleaning up and dusting shelves.”

Diane seemed to think for a moment. “I guess someone with your intelligence would find maid work a little mundane. But that doesn’t mean that you get out of our deal.”

“No, I know that. I’m not trying to get out of our deal. I’ll hold up my end, don’t worry.”

“Hmmm, okay, and seeing as I’m the best landlady ever, I’ll think of a way to make the day more interesting for you….More ‘stimulating’.” Diane put extra emphasis on the last word which had me a little worried.

“Thanks….I think.” I answered.

“No problem. But that doesn’t mean you get out of your punishment for today’s sloppy work.”

“Wait, seriously?” Was she really still going to punish me?

“Yes, seriously. Come on, we may as well get it over with. Hopefully you don’t find your punishment too boring.” I followed Diane up to her room where the spinning wheel of punishments was waiting for us. “I think we can get rid of this one for now….” Diane wiped away the ‘Writing Lines’ segment and grabbed the drywipe marker pen. “Don’t wanna repeat the same punishment twice in a row. But what to replace it with?” She tapped the pen on her chin for a second. The spanking and dress code change options were still there, and so was my free day off work ‘winning’ section and the extended chastity.

“How about, Diane cooks me a nice dinner and doesn’t tease me about my dick?” I said, lightheartedly.

“Ha, you wish, short stuff.” Diane laughed, “Besides, you love it.” 

“I do not love you telling me I have a small cock.” 

“Pfft, whatever you say, tiny. Now let me think….How about…No, no…that’s too inappropriate. I don’t think you could handle it.” Diane said, pretty much talking to herself.

I was curious about just what Diane would think was too inappropriate, given everything she had done to me so far. “What’s too inappropriate?” I asked.

“Don’t worry about it, just wishful, dirty thoughts from a horny old woman. Your innocent mind might find it too….intimate.” Diane replied, coyly.

“Seriously? I’m standing here in a maids outfit and panties and you’re worried about being too inappropriate?” I didn't know if her coy attitude was deliberate, but I had a feeling she was leading me somewhere.

“Well, I was going to write something along the lines of ‘Josh has to give Diane oral’ but like I said, it’s kind of an overstep, haha.” Diane waved her hand as though laughing off the notion.

I couldn’t help but wonder if she was serious…Would she actually let me do that? “Haha, yeah that’s….something.”

“Too far, right?” Said Diane.

“Well I wouldn’t say that.”  I replied.

“Wait, are you saying you would want to do that?”

“Well….I guess I wouldn’t object to it.” The truth was my cock was pressing hard against the chastity cage I was still wearing.

“Haha, oh my god, so you do want to. How long have you been harboring these naughty thoughts, Josh?” Diane said, her teasing tone returning.

“Okay, okay. I’m not harboring any naughty thoughts.” I answered, “I’m just saying I wouldn’t mind….that.”

“That?” Diane replied, cocking her eyebrow. “You mean licking my pussy? Eating me out? Going down on me? Is that what that means?”

“Yes, obviously.”

“I can add it to the wheel if you want?” 

“Okay, go ahead.” I said, my heart racing at the thought of that happening.

“Fine.” Diane turned back to the wheel, blocking it from my view for a second. When she turned back towards me I saw that the wheel did indeed say ‘Josh licks Diane’s pussy’ but she didn’t write it in the empty space, she had wiped away my ‘free day off work’ section and replaced that instead.

“Hey! You took away my prize.” I said.

“Well yeah, seeing as you made it so obvious that you wanted to lick me, then it wouldn’t be much of a punishment, would it?” Diane said, still holding the pen and still with one blank space.

“That was a cheap trick!” I crossed my arms, attempting to sound like I was annoyed, but it was hard to do that, still being dressed as I was.

“I know, aren’t I so bad? Now, what to add in this last spot…..I know!” Diane scribbled the words ‘Josh gets his nails done’. 

I stopped myself from whining, knowing that it wouldn’t get me anywhere. Instead, I just sighed and said, “Okay, fine. Let’s get this over with.” I knew which option I was hoping for. A day out of the maid’s outfit and without Diane’s teasing in the chastity cage would have been nice, but so would the opportunity to go down on her. I had never minded licking pussy before in the past, and my attraction to Diane had only grown stronger over the last couple of weeks. 

“With pleasure!” Diane said enthusiastically, giving the plate-sized wheel a spin. The rapid fire ‘click, click, click’ of the spinning prize wheel echoed throughout the bedroom as I awaited my fate.

“Ohhh bad luck, Josh. No prize for you.” Diane said as the wheel stopped on the ‘Dress code change’ option.

“Dammit.” I muttered.

“Aww, don’t be sad. I’m almost as disappointed as you are.” Diane said, sticking out her lower lip.

“Yeah, right. Every option on the board is a winner for you.”

“I know. My house, my game, my rules. Which means I can offer you another spin if I want. What do you think, sissy, feeling brave?” 

“What do you mean?” I asked.

“Simple, we spin again. Give you another chance to get your prize.” Diane rubbed one finger slowly along the seam of her leggings right next to her crotch. “Buuuut, if you land on another punishment, you have to take both.”

I weighed up my options, trying to run through the math in my head. Twenty percent chance of winning, one out of five. But the odds are reset every spin….like tossing a coin, the outcome was random and true randomness can’t be predicted, unlike the RNG systems that digital outlets use. If the wheel was completely random then I could easily spin five times and still lose, but what if….”Fuck it. Spin again!” I heard myself say the words while I was still trying to run the numbers in my head.

“You got it!” Diane spun the wheel before I could change my mind and I watched the wheel spin and spin, gradually slowing down. I watched the punishments click by until….

“Yes!” I cried out in triumph as the wheel landed on the option I had been hoping for: ‘Josh licks Diane’s pussy’, I realized right away that I had just celebrated being allowed to go down on her as though it was some sort of prize despite being promised no pleasure of my own, but I tried not to dwell on that thought too much.

“Well, congratulations, sissy-boy, looks like you’re a winner.” 

“Stop with the sissy stuff would you?” I said.

“Hard not to when you look like that. Anyways, your shift already ended for the day so I can’t enact your punishment, but you sure as hell can claim your prize.” Diane’s voice lowered to a sultry register at the end of that sentence and my cock twitched inside the small cage.

I was suddenly nervous that this was actually happening. 

Diane simply dropped her pants and underwear in a swift motion, clearly not worried about me seeing her naked. I guessed that was a good thing, seeing as I was about to become intimately familiar with that particular part of her. She sat down on the edge of her bed and motioned me forward. “Come on, sissy. You know your place.” She said, pointing to the spot on the floor between her legs.

I was too stunned at the sudden turn of events to protest her choice of words as I stepped forward and knelt between her legs. The chastity cage was feeling tighter by the second. “Don’t be shy now, you wanted this. Even spun the wheel a second time to get it. So….claim your prize. Lick me!” It sounded more like an order that time with a hint of desperation in her voice. Diane wanted this, that much was clear, the only question was which one of us wanted it more?

I leaned forward, tentatively at first but eager to taste her, to please her. And please her I did.

I had gone down on girls once or twice before in my limited sexual experience, but mostly I just fumbled around with my tongue and hoped I did a good enough job. There was none of that with Diane, she knew what she wanted and made sure she got it. She adjusted her own position with subtle shifts of her hips and used her hands to guide my head, her fingers gripping my hair possessively.

“Higher, harder…that's it, there. Faster. Faster…..fucking lick me, sissy, please your Mistresssss-fuck!” Diane grabbed my head with both hands and pressed me firmer into her sex as she came on my eager tongue. By the time I had licked her through her orgasm my cock was screaming for some attention of its own.

When she had finished bathing in the afterglow of her orgasm, Diane looked down at me, my face still glistening with her. “I'll bet you're pretty desperate to get your hands on these right now, aren't you?” She was jingling the keys to my chastity cage.

“Yes please!” The cage was almost painful by this point. 

“Hmm, maybe I don't want to give them to you.” She said in her usual tormenting way.

“What? You can't just keep them. You made the rules, my shift is over, and chastity wasn't part of my punishment.”

“Fine, fine. A deal's a deal. But first let's get you out of that dress and into the shower, we should clean you off first.” Diane said with a wicked glint in her eye.

“What do you mean, we?”

“Come on, sissy. We can use my shower.” Diane stood and led me into her en suite bathroom. She helped me out of the maids dress (not like I could remove it without her) and led me into the shower. I watched in shock as she removed her top and her bra, her large tits falling free with a little natural sag that gave them an extra ‘bouncy’ quality (for lack of a better term). “Pick your jaw up, Josh, they're just boobs.” Diane giggled as she stepped into the shower with me, the key to my cage in her hand. 

“Sorry, but, well, they're very nice boobs.” I had hoped that sounded charming and flirtatious, but with how horny I was it probably just sounded desperate.

“Haha, well aren't you sweet. Come on, let me help you.”

I stood under the water as Diane scrubbed me slowly, sensuously. “The tan lines are looking good.” She said, tracing the lines of the bikini top with her finger. “May need to top them up later.”

“Not if I can help it.” 

“Haha, we'll see. Now turn around.” I took one last look at her naked body, dripping with water and soap as I turned my back to her, facing the wall of the shower. “Put your hands on the wall.” She guided both my hands up to about head height and had me place my palms flat against the shower wall. “Keep them there.” She whispered in my ear.

Much to my relief, one of Diane's hands crept around to my front and inserted the key into the cage. My small cock immediately sprung to a full erection. “There's my favorite little cock.” I blushed but didn't argue as her hand had started stroking up and down my shaft, using soap as lube. “Don't take those hands off the wall, if you do, this stops, got it?”

“Yeah…got it….please. Keep going.” The feel of her naked body pressing into me from behind along with her hand on my cock had me eager to keep this going. That was when I felt her other hand creep down between my still smooth and soaped up ass cheeks. “Diane….”

“Shhhh, relax, Josh. Let me make you feel good. You're going to love this, I promise.” Diane spoke softly into my ear as one of her fingers rubbed against the outside of my asshole. “Thaaat's it, feel me.” The hand on my cock kept up a slow pace, deliberately not pushing me over the edge and keeping me as horny as possible as the finger at my rear increased its pressure.

“Haaaaahh.” I gasped as Diane's finger entered my ass, breaking past the ring and sinking into me.

“Shhhh, that's it, Josh. Feel me filling you.” Diane brought her soap-slicked finger back a little before pushing it all the way back into me. As she penetrated my ass I felt a pulse from deep inside me that seemed to ricochet around my crotch area. 

I almost moved my hands, but I kept them there, on the wall with my ass sticking out slightly and being filled by Diane's finger. She moved both her hands faster now and at some point my hips had started to move in time with her hands. I didn't know if I was thrusting forward to meet the hand on my cock or thrusting back to meet the finger in my ass, either way, it was obvious I was into whatever was happening. “Fffuck.”

“Mmmm, you like this. Does it feel good? You like having your ass fingered?”

“Y-yesss.” I gasped in the positive, lost in the new sensations as I approached climax.

“I knew it! Get ready, Josh, you're gonna remember this one for a long time.” Diane added a second finger and pushed hard, a short burst of pain was followed by a full feeling that heightened the sensation. I was moaning now as my orgasm approached and Diane knew what was about to happen. She leaned in close to my ear and hissed a word that pushed me over the edge. “Ssssslut!”

“Oooooh fuck yess!” I cried as I exploded in an orgasm more powerful that I could remember ever having had before, and it had happened with my landlady fingers in my ass. 

I remained in place, gasping as the hot water washed away the evidence of what had just happened, but Diane was right, I wouldn't forget this one. 

“I'll let you finish off in here.” Diane gave my ass a slap after removing her fingers and stepped out of the shower, leaving me in blissful shock as the stretched, empty feeling settled in my ass. “Oh, and Josh…” Diane said before leaving, “you can take your hands off the wall now.” 

“Right.” I quickly straightened up, not realizing I was still in the submissive position, my head spinning….

—

I woke up the next morning feeling somewhat conflicted, on one hand I had immensely enjoyed what happened in the shower last night, on the other hand, as a guy I was pre-programmed to think a certain kind of way about anything entering my ass. I decided not to dwell on those feelings too much as I got up and checked my emails….nothing from work, still nothing to do. Nothing except dress up as a maid and serve Diane. That thought earned a twitch from down below which I chose to ignore.

I told myself there was no way I was enjoying this dynamic. I was just doing it because she bought me things. I headed downstairs to grab some breakfast, the first thing I saw was the page from my last punishment, the words ‘I have a tiny cock’ written over and over again in my handwriting.

“Morning butt-slut.” Diane had appeared behind me and slapped my ass, her humiliating nickname reminding me of last night.

“Stop that!” I said, hoping this new nickname wouldn't stick.

“Why? You clearly loved it.” She replied.

“I wouldn't say I loved it. It was something new, that’s all.” I replied, willing my cock not to respond to her. “A one time deal!” I added, firmly.

“Awww, but I had so much fun. Maybe I'll just have to add that to the wheel.” Would she really? “Something like ‘Diane gets to finger Josh like a horny college girl’.” She added, laughing.

“Don't you dare!” I said, wondering if she was serious.

“Oh I could, but the only question is….would it be a punishment, or a reward. I mean you clearly enjoyed yourself. Which would you prefer, pleasuring me with your tongue or having my finger in your ass? Which would you enjoy more?” 

“Knock it off.” 

“Okay, if you say so….Slut.” Something about the way she said the word ‘slut’ triggered something in me, a flashback to me exploding in the shower last night, moaning with her fingers deep inside….

“Shut up!” I shook the thoughts away as I felt my cock stiffening.

“Anyway, don't be late for your shift today, I get to add something new to your outfit, remember.”

“Yeah, yeah. Can't wait.” I replied, dryly.

I didn't have to wonder long what the new addition to my outfit would be, I heard a knock at the door and Diane rushed to answer it. She was smiling as she carried a medium sized box back through the house. “Can't wait to see how these look on you.” She said in a giddy voice. 

I was assuming the box contained footwear of some sort and I wasn't wrong. As I stood in the maid outfit once again, Diane opened up the box to show me a pair of black, shiny shoes with a high, thin heel. “Heels?!”

“Yes, heels. It's about time you got used to walking in them, they'll really make your legs pop in those stockings. I special ordered these last night, spent a lot of money for the extra addition too.”

The extra addition turned out to be an added strap that ran around the ankle and had a loop where a small padlock could be fastened through. I should have seen that coming, really. “Of course they lock.” I sighed.

“I know, couldn't resist. But they'll be perfect for a sissy like you.” Said Diane.

“I’m not a sissy!”

“For the next couple of hours you are. Now come on, into the shoes.” I sat down as Diane slipped my feet into the heels. Two quiet clicks later and I was locked into the heels. “Okay, now take it steady, let me help you up.” I stood up gingerly as Diane held my hands. I was forced onto my tiptoes by the shoes which caused my calf muscles and my ass to clench a little as I tried to balance myself.

“Aren’t these too high? How am I supposed to work in these?” I said.

“Women work in heels all the time, Josh. And they do it for a lot longer than a couple of hours a day so I’m sure you’ll survive. Don’t worry, we’ll take it slow today to help you get used to the heels.” Diane took one of my hands in hers and stood alongside me. “Come on, sissy. I’ll walk with you.” 

I walked slowly around the house, hand in hand with Diane, feeling embarrassed as I realized I looked like a toddler wobbling around, holding Diane’s hand so I didn’t fall down. We spent some time walking around like this with Diane giving me pointers on how to position my feet as I took a step, eventually she let go of my hand and let me walk around the living room unassisted for a while.

“That’s it, Josh. You’re looking better already. Now let me see your curtsy.” 

I grumbled a little but tried the curtsy as I had done in the past, and almost fell over sideways. “Hahaha, cute. But try again, come on.” Diane made me repeat the curtsy a few more times until she was satisfied with my performance. 

“Okay, walk around the sofa, come back in front of me and curtsy.” 

“Fine…”

“It’s ‘Yes Miss Ryan’.” She said, sternly.

“Right, fine…Miss Ryan.” I took off on my slow, unsteady walk around the living room until I got back in front of Diane and performed the curtsy.

Diane gave a happy clap of her hands when I had finished. “Well done, Josh. You’re a fast learner. Let’s go again….” I was made to repeat the exercise a few more times over the next hour with Diane watching. I was gradually beginning to feel a little steadier on the heels as I neared the end of my shift.

As Diane had me practicing how to bend over safely in heels, her phone started ringing and she answered quickly. “Diane Ryan…….What? Again…….how many times have I told you not to let him…….Okay, okay. Fine. I’ll be right there.” Diane shut off the phone call and abruptly stomped towards the front door.

“Everything okay?” I asked as I followed her incredibly slowly to the front door. By the time I got there, she had her shoes on and was clearly about to leave.

“Sorry, Josh. Gonna have to run to the office for a while, don’t worry. I won’t be long.” And she was gone before I could even say goodbye. 

It was as I stared at the front door that I looked down at myself and realized that I was locked into pretty much everything that I was wearing and I was pretty sure Diane had the keys. “Fuck.”

I stumbled around the house, looking for the keys but I knew I wouldn’t find them, even if they were here. Diane had never left the keys unattended while I worked so I doubted they would be here now. I sighed, defeated as I figured I was stuck in the outfit, heels and the chastity cage until Diane got back.

I decided to try and relax a little while Diane was out, but everything I did while wearing this outfit made me feel more girly and submissive. Even going for a pee meant bunching up my skirts and having to sit down due to the chastity cage. This followed by me bending over to pull up my panties and straighten out the outfit. I sat and played some games for a while in my room, wondering when Diane was coming back to release me from the outfit. I had to wonder if she had left me locked into the outfit on purpose, but surely not, she was just in a rush and forgot. Although the more I thought about it, the more I figured that I wouldn’t put it past her.

Finally, I heard the door open and close. “It’s about time!” I muttered to myself, shutting down my game and heading downstairs to meet her. “Finally!” I said as I followed the sound of Diane into the kitchen where I heard her opening the fridge. “My feet are really starting to hurt in these damn-” I froze on the spot as I entered the kitchen, Diane wasn’t home. Paige was.

End part 8.