Owned by the Landlady - Chapter 2 (Patreon)

Owned by the Landlady - 2

Josh - It wasn’t for her to wear

I did not sleep well that night in the chastity cage. I kept getting woken up by my cock trying to get hard in my sleep. The next morning I was tormented by my morning wood pressing against the cage, which caused me to think about how Diane had taken away my own access to my cock, which turned me on more, which caused me more discomfort and round and round it went.

I was grateful for work as it meant that my mind was occupied by lines of code for most of the day, but that changed as soon as I got home and saw Diane sitting in the living room watching something on TV. 

She looked over when she heard me enter. “Oh, hey there, roomie. How was work?” She asked, smiling as though she hadn’t locked my cock away.

“Work was…work. It was fine, I guess. How was your day?” I asked, taking a seat in a chair opposite her.

“Ah, pretty boring, really. A day of video dial-in meetings and not much else.” Diane was some kind of HR rep for a big company that had a bunch of locations, so most of her days were spent working remotely from an office she had set up in a spare room downstairs.

I tried to keep up the facade of normal conversation but eventually I couldn’t keep from asking. “Okay, I have to ask about…you know.”

“About what, dear?” She was playing coy, clearly.

I sighed. “About the chastity cage you locked me in last night, obviously.”

“Ooohhh, right, the cage. Well I did warn you to stay out of that case.” She replied.

“I know, I know. But I've learned my lesson. How long do I have to wear it for?” 

“I haven’t decided yet. But you’ve barely been in that thing one day, you can last a little longer, be a good boy today and I’ll think about letting you out.” Said Diane. 

“Okay, fine. In that case, is there anything I can help you with?” I asked.

“Sure, you can start by rubbing my feet for a while.” Diane lifted up her leg and flexed her toes which were covered by sheer hose.

“Fine.”

“Without the attitude.” She added, smiling, clearly she was enjoying tormenting me.

I rolled my eyes but added, “It would be my pleasure, Ma’am.” I said, moving to sit down next to her, but she stopped me.

“No, no. You can kneel down in front of me.” She pointed to the floor right in front of the couch.

“Are you serious?”

“Yep. Unless you want to stay in the cage for longer? Personally I don’t think it matters, a cock as small as yours is probably better being locked away anyways, hahaha.”

“Stop.” I protested her taunts about my size but I felt my cage tighten at her comments as I kneeled down in front of her and picked up her foot.

I massaged her hose covered feet for a while while she finished watching whatever she was watching and allowed me to stand and move freely again. Of course after being made to kneel at her feet the only thing I really wanted to do was go and jerk off, but that was out of the question.

Diane didn’t ask much more of me after that and I found myself a little disappointed, there was some part of me that had enjoyed her ordering me to do something. It was a little later in the evening and I had decided to join her in the living room for a while.

It seemed like she wasn’t going to mention the cage again and I was looking for an opportunity to bring it up but never got one. It felt weird for me to just outright ask for it, essentially I would be asking for my landlady to let me jerk off.

Thankfully, it was Diane that brought it up, a little out of the blue. “So, how’s your little pecker doing, Josh?”

My cock twitched before I answered. “A little constricted.” I answered.

“Haha, I bet. Still feel like it was worth it to go snooping around in my room?”

“I’m starting to think it was a bad idea.”

“Well you've only seen a small portion of what that case has to offer. Don't try and tell me you're not curious about what else is in there.” Diane said with a confident smile.

“I wouldn't be too sure about that.” I replied, trying to sound like she wasn't absolutely right. “Although I guess I wouldn't mind seeing you in that maid outfit I saw.” 

“Hahahahaha, ohhh, Josh, you poor naive boy,” I wondered briefly what she found so funny, then she stepped in close and leaned her head close to my ear before adding in a low voice. “That dress isn't for me to wear.”

My eyes must have widened in shock because she laughed a little more as she stepped back, leaving my cock twitching in the cage. Surely she couldn't expect me to wear something so feminine….could she? More importantly, would I let her? And would I enjoy it as much as the other stuff?

“Wait, wait….you make guys wear that stuff?” I asked.

“Course I do. There's nothing more fun for me than taking a guy and turning him into my personal sissy servant. Maybe that's what I'll do to you, I haven't decided yet. I'll have to see how you look in panties first.” Diane said it as though I didn’t get a choice in the matter. 

I could only chuckle nervously. “Ha, okay, you're messing with me…..right?”

“What do you think?” Diane answered with a smile as she left the room, leaving me wondering. 

—

The following day Diane decided I had finally earned the right to be free from her cage's torment, right before she headed out for the evening with her friends. “Okay, Josh, I'm heading out for a while. Here, you want this?” I was watching TV in the living room when she called out from the hallway. I stepped into the doorway to see her.

“Want what?” Diane was dressed for an evening of cocktails and was wearing the dress to prove it. A deep neckline that pushed her generous chest up and together. 

She reached into said cleavage and pulled out a small, silver key. “This.” She dangled it teasingly from her finger. 

“Yeah, obviously." I replied, eagerly.

“Ask me nicely and I might not take it out with me.” 

“Okay, can I please have the key?” I said, holding out my hand, only for Diane to yank it back out of my reach. The heels she was wearing made her seem much taller than me.

“What key is it you want?” Said Diane.

“The key to the chastity cage I'm wearing, obviously.” 

“Ohhhh, that key. Sure, here you go.” She dropped the keys into my waiting palm. “Well I'm off, I'm sure I know what you're going to be doing tonight.” She added, making a lewd, jerking motion with her hand as she left the house.

My cock was half hard just from that interaction with her, so it didn't take me long to free myself and find the relief I had been waiting for for the last couple of days. I dropped the cage in the sink and cleaned it off when I was done, wondering what to do with it. I left it on my bedside table until Diane got back and asked for it.

—

I was more focused at work the next day, not that it would have made a difference. I was dealt some pretty devastating news and headed home with a glum expression.

“Oh my, who pissed on your cereal?” Diane asked later that afternoon, no doubt sensing the mood on my face.

I sighed as I broke the news to her. “Work…..I uhh, think I might have to move out.” I said, noticing how Diane’s face seemed to look a little disappointed.

“Move out, so soon? What happened?” She asked, sitting next to me on the sofa and rubbing my back affectionately.

“There was a huge problem with some of the conveyor systems installed at the factory, they’re not compatible with the robotics and automation that I’ve been working on for the last couple of weeks. A setback like this is going to take weeks, months even to rectify. It’ll be a top to bottom change to the way the whole floor is set up. So effectively I’m not needed.”

“Oh dear, so what does that mean for you? They’ll need you eventually, right? Don’t you have a contract with them?”

“Yeah but there’s a furlough clause in there and because I’m so young, basically fresh out of college, I didn’t really have an opportunity to negotiate it out. So I won’t have any money to sustain myself for the next couple of months or so. So I can’t pay the rent here, or anything else for that matter.” I slumped over as I considered my options. I would have to move back to my parents, but then I wouldn’t be ready to restart my work when the factory was ready, I could miss the restart date and they would get someone else and I would be back to square one.

“Do you actually want to go home?” Diane asked.

“No, of course not. I like staying here with you and this job was going to be huge for me. Having this on my resume would do wonders for my career, without it I’m just another college kid with no real world experience.”

“So stay here.” Diane said, “I’ll waive your rent for a couple of months.”

“What? No, Diane, you can’t do that.”

“Sure I can, you’re a good tenant, I don’t want to risk sifting through more weirdos who might turn up.”

“You’re just being kind, I don’t wanna be the guy who mooches off his landlady.”

“Then don’t be, I’m sure I can think of ways to keep you busy. You can work off your rent.”

“Work it off how?” I asked.

Diane shrugged a little. “Just a few chores around the house, maybe in the garden. You can earn your keep that way. That’ll be perfect actually, I’ll have a little more free time if the house is taken care of, and you won’t have to feel like a charity case. And when your factory gets back on track then normal service will resume. Sound good?”

It sounded too good to be true. “Diane…you’re a life saver!” I turned and gave her a hug as thank you and it occurred to me that I had never actually hugged her before. This was a woman who had spanked me over her knee and handled my cock into a cage but I hadn’t actually hugged her before. “Sorry…” I said, breaking the hug. “I’m very grateful, thank you.”

“You’re welcome. Now turn that frown upside down, Mister, my niece is coming over for the night.”

“Paige, right?” I asked. I had been told that she might be here from time to time but I hadn’t actually met her yet.

“Yes, she'll be staying the night so I want you to be on your best behaviour.”

“Right. You got it, boss!” I said, cheering up at her generosity.

Paige turned out to be around my age, twenty two, twenty three maybe, and had no problem showing off her well toned body. She wore denim shorts and a top that exposed her midriff for most of the day. She was friendly and easy enough to get along with as we all had dinner together. She told me she was happy to sleep on the couch seeing as I had ‘stolen her room’ as she put it, so late evening we bid each other goodnight and Diane and I headed upstairs.

“Night, Diane.” I said as I pushed open my bedroom door.

“Josh, hang on a sec.” Diane stepped in close enough for me to smell her perfume as she leaned on my doorframe. “I want you to keep that little cock of yours to yourself tonight, you hear me?”

“What? What do you mean?” I said, a little taken aback.

“I mean Paige is right downstairs, your age, a very pretty girl and you're both under the same room, and I know exactly how eager that little thing between your legs is to get you into trouble. Now tell me you'll keep it on your pants while Paige is here or….” Diane looked at me in the eyes, her tone laced with suggestion, “...or I can always put it back in the cage.”

“Okay, okay, I'll keep it in my pants, scout's honor!” I added some kind of scout salute and Diane smiled. 

“Great. Goodnight.” 

I couldn't blame her for wanting to protect her niece, but I was hardly the ‘sneak out of my room to seduce a girl I had only just met’ type. More the ‘befriend someone for years until I get up the courage to make a move and hope she likes me back’ type.

I was watching a series on my laptop, lying in bed a little later that night when I heard a soft knock on my door. I didn't want to yell out an answer so late so I walked over and opened the door to see Paige standing there with a small bottle of vodka and two glasses. “Hey, can't sleep, want some company?”

Now, given the warning I had just received, my answer should have been ‘no’ but I was just too dense to see the danger, nor was I confident enough to believe that Paige would be interested in anything to do with me. “Sure, come on in. Welcome to, uhh, your room, I guess.”

“Ha, yeah, love what you've done with the place, though I would have at least put a TV on the wall.” Pauge said, walking in and sitting on my bed.

“Yeah I was saving up for one but that might have to wait a while….” Paige and I drank a few shots of vodka while I filled her in on my situation.

“So, get Aunt Diane to buy you a TV, she's looooaded.” Paige said, loudly.

“Shhh! And what do you mean, loaded?” I asked.

“Yeah, Diane Ryan is like, rich as fuck. She was on a team that rewrote a bunch of HR policies for the company she works at, I forget their name, but the big guys gave the whole team a huuuuge payout. She only works to keep from getting bored.” Paige poured two more vodka shots, “I'm guessing that's why you're here, she doesn't need the rent money, so she must just like the company.” 

“Huh, I didn't know that.” I said, though I guess she wouldn't have a reason to tell me.

“Duh, how do you think she paid for that pool and decking outside?” Paige added, right as her demeanor changed…“So, Josh, couldn't help but notice you checking me out earlier….like what you see?”

“Oh shit, sorry, I thought I was being subtle.” I replied, taken by the sudden shift in tone. When did she get so close to me?

Paige's hand crept up my bare thigh, only my shorts as protection and I knew they would do nothing to hide my growing erection. “Paige, you probably shouldn't…”

“Why not? You're here all alone, unless you're secretly sleeping with my Aunt Diane?” 

“Ha!” I blushed and stammered out a response. “Nope, nothing like that. But she did give me the warning before bed.”

“Oooh, so she told you not to go near her ‘sweet innocent niece’ is that it?” Paige asked, her hand still creeping up my thigh towards my shorts.

“Yep, pretty much. And she’s already doing me a favor by letting me stay here so I really don’t-ahh.” Her hand had found my crotch and it was very obvious where my cock was situated, given that I was now fully erect. “Paige….”

“Shhh, relax, Josh. We’re just having a little fun.” Paige gripped my cock through my shorts and massaged it a little as her other hand pushed me backwards so I was lying with my back flat on the bed and my feet on the floor. I showed no resistance as her hand moved down the front of my shorts to grip my cock.

I gasped at the skin on skin contact and there was a part of me that panicked as I wondered what Paige would think of my size now that she had felt it. Diane’s comments about how small it was had left me a little paranoid, despite having no complaints before. Paige, thankfully, didn’t comment on my size. 

“That’s it, Josh, let me work this big cock of yours.” Paige said in a voice that seemed to be creeping louder. “

“Shhh, oh fuck, Paige….Keep it down…your aunt.” Although I was relieved to hear her call my cock big, Diane had given me a complex!

“Don’t think about her right now, baby. Just focus on me and what I’m doing to this cock of yours.” Her voice was definitely louder. “Does it feel good? My hand working your cock. Are you going to cum for me, Josh…ARE YOU?”

“Sssssshhhhhhit! Paige.” I was lost in pleasure now as her hand rapidly worked my shaft inside my shorts.

“Cum for me, Josh, I want you to cum for me. Come on, baby…..come on….” Her hand was moving faster and faster now and she was making no effort to be quiet. I slapped my hand over my mouth to stifle my moans as I exploded inside my shorts. Paige gave a loud, overly dramatic moan of her own as I coated her hand and my shorts in my cum. “Ohhh, that’s it, Josh. Cum for me…YES!”

Paige removed her hand from my shorts a few moments later and wiped it off on my sheets. “That was fun, and I can tell you enjoyed yourself. Now I have to be up and out early tomorrow so I’ll leave you to it. Niiiggght.” And she was gone, leaving me panting and soaked in my own ejaculate. 

—

The following morning felt a little off, I would usually be going into work but that wasn’t necessary right now, so I wondered what it was I should be doing as the memories of last night came flooding back. Did Diane know what had happened with me and Paige? 

I got my answer to that question pretty early on when my bedroom door burst open and Diane stood on the other side with a face like the cat that ate the canary. “Good morning, Josh.” She said in a tone laced with something devious and plotting. “Did you have fun last night?”

“Good morning…Umm, yeah it was…fine.” I replied, playing dumb.

“Josh, I’m going to give you one chance to come clean to me, do not lie to me. Paige was in your room last night?”

“Yes…I’m sorry, Diane, really she came in and we had a few drinks and well….something happened. But we didn’t sleep together and to be honest, most of it was on Paige..”

“Oh really! Most of it was on her, and I’m assuming you spent the whole time trying to fight her off. Valiantly refusing her advances and asking her to leave?” Diane had marched into my room as I stayed hidden beneath the sheets.

Now that she mentioned it, I didn’t exactly push back on Paige’s advances all that much. “You’re right…I should have asked her to leave. I’m sorry.” I said, meaning it.

“Not yet you’re not.” Diane marched over to my drawers and pulled open the top one, the one filled with my underwear. “That chastity cage, you’re going to go and put it back on and give me the keys.” Diane said as a statement, not a question or even an order, just stated something that she was sure was going to happen. 

“Tha chastity cage? Come on Diane, please…isn’t there something else you can do to punish me for this one?” I asked, wanting to avoid the cage again, even though my cock had started to get hard at the suggestion. 

Diane spun around to face me. “Go and put the chastity cage on, now.”

“Yes, ma’am.” I said, shuffling off to my bathroom. After a few minutes of fumbling around and with the help of some cold water, my cock was once again caged and I headed back out to my bedroom in just my boxers.

“Take those off.” Diane said, pointing to my underwear. I noticed a small, plastic bag on the floor next to her and my underwear drawer had been emptied.

“What are you doing with my underwear?” I asked.

“I’m revoking your male underwear privileges as part of your punishment. Give me those.” She held out her hand and I did as she said. I watched as my last pair of boxers was stuffed into the bag and she tied it off at the handles as I stood there with my hands covering my caged crotch. “I’ll be right back.”

Diane left for a few minutes and returned with a handful of panties in different colours and styles. She tossed a pink, frilly pair to me. “Put those on.”

I caught the panties and looked at them before asking. “Seriously? These won’t even fit me.”

“They’ll be tight, but they’ll do until I can get you some of your own. Put them on.” 

I decided to just get this over with and do as she said. She was understandably angry with me so the least I could do was take my punishment like a man…a man in panties, apparently. I put the panties on, feeling how the soft material hugged my ass and cradled my caged package. It was not unpleasant.

Diane smiled as she eyed me up and down in the panties while I blushed furiously at her examination. I was incredibly nervous as I remembered her words from before, ‘I'd have to see how you look in panties first’.

“Hmmm,” Diane studied me for a long moment, making me feel very exposed, “not bad, a little too much hair but that can be fixed, nice enough legs…” She was pretty much just talking to herself at this point. “Need to firm up your rear a little but it has potential. Now. Where is the key to your cage?” 

“Bathroom.” I answered, shaking.

“Fetch it for me.”

I retrieved the key on unsteady legs while my cock pulsed in the heated situation. “Here you go.” I offered her the key without thinking.

“Thank you, dear.” Diane leaned in close and added, “I want you to remember how you locked yourself away and gave me the key so willingly while you think about what that says about you.” Diane walked to the door, “Grab that, and follow me.” She pointed to the bag containing my underwear.

She walked out of the room and I followed, bag of boxers in hand. I followed her downstairs and towards the back door of the house. Diane opened the door and I cowered away, the outside world feeling like a giant eye staring at me in the panties. “Take that bag, and toss it in the trash.”

“Like this!” 

“Yes, like that.” 

“Diane…Come on, I can’t go out there like this.” I pleaded.

“Why not? There’s no one in my backyard and the rubbish is away from the street….mostly. But let me put it this way, you can take out the bag, like that, or I can take it out for you, but if I do, I’ll be adding the chastity key to the bag before throwing it out.”

There wasn’t much argument to be made to that, so with a beating heart and shaky legs, I rushed out the back door, ran along the wall to the side of the house where the bins were, thankful of the high fences in the back yard. 

I crouch-ran back through the back door as quickly as the awkward position would allow, Diane was laughing as I re-entered. “Hahaha, you look hilarious like that, like a scared kitten in pretty panties.”

“I’m so glad you’re amused.” I retorted.

“Oh I am. Now I think we can consider you suitably punished, but just so you know, you are to be wearing panties at all times while living under my roof. I will be checking to make sure you’re following this rule and if I find out you’re not wearing your sexy new undies, you will be punished. Got it?”

“Yes, ma’am.” I replied, desperate to run and get dressed.

“And stop calling me Ma’am, it makes me sound so old. Now go, have fun, watch a movie or whatever it is you usually do in your room….Although I’m guessing one of your favorite pastimes has been ruled out, hahaha.” Diane patted the cage through the panties as she walked away, laughing at her own joke.

I headed upstairs to get dressed, hiding the tight panties from view to make myself feel a little more manly. The problem was, without work to do all I really had was movie streaming on my laptop to pass the time. I was planning on buying a TV and a games console at some point, but that would have to wait…

—

I was in the kitchen helping Diane prepare dinner, borne out of boredom more than a need to be helpful. I had my hands in the sink, cleaning off some cutting boards when Diane came up behind me and stuck her hand in the back of my pants. “Hey!” I yelped as she pulled up on the pink fabric of the panties, giving me a slight wedgie.

“Just making sure they’re still there, sweetie.” She gave my ass a friendly swat as she released the fabric. “Maybe I should get you an apron or something to wear while you help out like this. Or I could always grab that maid outfit you were so interested in?” 

“Not a chance!” I replied, ignoring the twitch from down below. “I will never wear that dress.”

“Haha, sure, Josh, you keep telling yourself that.” 

“I will!” 

“Riiight. Because wearing a maid outfit would be sooo embarrassing. Says the guy in the kitchen wearing pink panties.”

“Shut up.” I replied, Diane stuck out her tongue in a juvenile manner before turning back towards the stove. Her playful demeanor seemed to have returned now that my punishment was out of the way.

I had only been in the cage for a few hours now and already I was wondering what I would have to do to get it off. I was outwardly hoping that it wouldn’t involve the maid outfit….but a small, traitorous voice deep inside seemed to have the opposite idea….I chose to ignore that voice, despite being turned on at Diane’s control, dressing as a maid would be a step too far. Right?

End part 2