Owned by the Landlady - chapter 1 (Patreon)

Owned by the Landlady

Josh was running out of options. He was twenty two years old and had just scored a great job. The only thing he needed was a place to stay nearby while he saved up enough money and found somewhere of his own.

He had seen the advert online for a woman who was looking for a lodger, so he had made himself look as presentable as possible and drove over to her house. The meeting went well, the house was perfect and Miss Ryan seemed easy enough to get along with. So arrangements were made and Josh was to move in a week later on his start date.

—

Josh - it started with dirty shoes

“I told you, call me Diane.” My new landlady said as she helped me carry in what little stuff I actually had. “Miss Ryan makes me sound way too upper class.” The few interactions I had had with her painted a rather pleasant picture. She was a few years older than me, maybe in her early thirties, but she was incredibly friendly, had a sense of humor and hadn’t balked at the idea of a young male renting her room.

“Thanks, Diane. But you didn’t have to help me, honestly I barely have anything to bring inside anyway.” I said.

“I know, I'm just trying to be a good hostess. It's been a while since I had any company, and it'll be nice having a strapping young man to help out a little.” Diane said, smiling pleasantly.

“Ha, I don't know how strapping I am. But I'll take the compliment.” I replied.

“So, Josh, can I expect any lady visitors?” She asked.

“Oh. I doubt that….at least not any time soon. I'll be focused on work more than anything. It's a pretty good job and I don't wanna mess it up.”

“Okay, well just give me a heads up if you end up getting lucky, I'll be sure to put some headphones on, haha.” I gave an embarrassed smile at her comment, I really wasn't expecting to be getting lucky at all.

“So, you build robots or something?” Diane asked.

“Not quite, I'm a software engineer. So I tell robots what to do, pretty boring but it pays well and I have an eye for math and coding……” Diane and I chatted for a while as I got moved in. I found myself pretty pleased with my arrangement and looking forward to my new life.

—

A couple of weeks later I was fully settled into my new routine and had even made a few friends among my new colleagues. I was getting dressed to hit a few bars with those colleagues when Diane caught me checking out my reflection in my bedroom mirror.

“Well hello handsome.” Her voice came from my open bedroom door. “Sorry, your door was open.”

“Oh, hey, it's fine. How do I look? Been a while since I went out anywhere.”

Diane walked up behind me so she could see my reflection. “Very nice, I would definitely let you into my panties.”

I almost choked on thin air at that comment. Diane had often been a little flirtatious, but nothing quite so brazen. I blushed a little before forming a response. “Haha, that's good to know.”

“Aww you're blushing, you're very cute, Josh. Go have fun. Text me if you score, I promise not to listen.” Diane said, heading out. I couldn't help but notice the sway in her shapely ass as she left.

I did not score that night. But I did wake up with a hangover on Saturday. Diane found me in the kitchen in the morning with a glass of water and a headache. “Morning, night owl. How was last night?” She asked.

“It was fun, actually, decidedly less fun this morning though.” I replied.

“Oh dear, so I trust there's no girl upstairs in your bed?”

“Nah, not that lucky.”

“Good, because I need to talk to you about the mess you left in the entrance way last night.” Diane didn't seem super annoyed, but I felt bad if I had left a mess all the same. I followed her out of the kitchen to the front door and saw what she was talking about. I had traipsed dirt into the house and kicked my shoes off messily, they were both strewn across the floor right next to the shoe rack. “Ah, shit. I'm sorry Diane, I didn't realise last night when I took them off.”

“Well it looks like you're being punished enough by that hangover already, so I'll let this one slide. But next time, you'll be going over my knee, mister.” Diane said, wagging her finger playfully.

“Haha, well that would be the most action I'm getting lately.” I replied.

“Well, lucky for you I have no problem giving a naughty boy a good spanking.” I couldn't help but feel a slight twitch between my legs as she planted that image in my mind. Was she serious? No, of course not, that mischievous look in her eyes was all in my head.

“Then I guess I'd better behave myself then.” I said, still wondering if she was serious….

A few days later as I was getting in from work, I remembered to kick the dirt of my shoes before entering and took them off, hanging them on the shoe rack near the front door.

“Good boy, no spanking for you today then.” Diane had walked by just as I was putting away my shoes, still on the same spanking joke….was she joking.

Diane had just gotten back from yoga by the looks of it and I couldn't help but notice her ass in the tight yoga pants as she walked away.

“Joshua! Were you just staring at your landlady's rear?” Diane had turned on her way into the kitchen and caught me. Her voice was still light and playful even as she admonished me.

“Whoops, guess you caught me. I'm a sucker for tight leggings.” What else could I say?

I had to give my head a little shake as I stared at my shoes in the rack, my mind wandering….

For the next two days I hung my shoes up when I got in with an odd sense of foreboding, what would happen if I left them out? Would she actually spank me? And did I want her to?

On the third day I decided to try my luck. I looked down at the faint traces of dried dirt on the bottom of my shoes from my walk home and decided not to wipe my feet on the mat or kick the dirt loose outside the door instead I simply kicked them off my feet and left them there, on the floor. Diane wasn't in the house when I got home, so I had to wait to find out what would happen….

“Josh.” Her voice called from the front door a short while later. “Could you come here, please.” I took a deep breath and headed down to the front door.

Diane was waiting next to my shoes with a stern expression. “Oh shit, my shoes!” I said, acting as though I hadn't done this on purpose. “Sorry, I'll tidy this up.”

“Josh, what did I say would happen if this happened again? Do you remember?”

“Umm, yeah, I think you said you'd put me over your knee.” I answered.

“So you do remember, and yet you still did it again. So you know what happens now, don't you?”

“Umm, I wasn't sure if you were serious.” I said, a little sheepishly. It sounded like she was serious about the spanking after all….and I had just provoked it….deliberately.

“Oh I was very serious. Follow me.” It was clear she was trying to hide her smile as I followed her into the living room. She took a seat on the edge of the sofa, her legs bent at a ninety degree angle with her feet flat on the floor. “Okay, Josh,” Diane patted her thighs, “over my knee.”

I was stunned, if this was a joke she was taking it further than I thought. “Really?”

“Yes, really.” Her reply was simple.

I did as she said, partly because I wanted to hide the fact that my cock was starting to get hard. I laid down across her lap with my crotch pressing against her thighs.

“Well, these will need to move.” Diane grabbed the waistband of my pants and pulled them down to my knees, my boxers followed, but thankfully she only pulled those down far enough to expose my ass, so at least my cock was still covered. “There, much better.”

‘Slap!’ The first blow rang out loudly in the quiet room. It stung, but nothing I couldn’t handle. ‘Slap!’ The opposite cheek was struck next and Diane started up an alternating pattern, reddening both cheeks evenly.

After a short while, the pain began to build a little more and I found myself squirming around on her lap.

“Hold still!” I felt one of her legs wrap around both of mine and her non-spanking hand gripped my waist tightly.

‘Slap!’ “This will teach you, ‘Slap!’ “not” ‘Slap!’ “to leave a mess” ‘Slap!’ “on my floors!” ‘Slap!’

The spanks became harder and I was squirming around like crazy, my ass stinging more and more with each blow…yet somehow, despite the pain, or maybe because of the pain, I was rock hard! So hard that I knew she had to have felt it pressing against her leg.

‘Slap!’ ‘Slap!’ “Owww, shit! Shit.” ‘Slap!’ “Ow! I’m sorry, Diane!” ‘Slap!’

“I should think so!” ‘Slap!’ Finally, she was done. Diane released me and allowed me to get off her lap, but she wasn’t quite finished yet. “Ah-ah!” She stopped me from pulling up my pants, which I was desperate to do as I was still trying to hide my erection from her. “Leave those where they are and go stand in the corner.”

“What? Really? Diane my-”

“Yes, really. You can stand there and think about your punishment and I want to be able to see those red cheeks of yours while you do, so the pants can stay where they are. Now, corner!” Diane pointed to the corner and I actually followed her order.

I stood, nose in the corner of the living room with my pants around my ankles and my boxers pulled down to expose my ass cheeks. I heard Diane leave the room and yet I still couldn’t bring myself to move from the corner. She had thoroughly spanked my ass, I could still feel the tingling sensation, and I didn’t dare disobey her.

“I do love the sight of a well-spanked behind.” I could hear the amusement in her voice as she stepped back into the room. “And don’t think I didn’t feel your little cock pressing into my leg.” I didn’t know if she was expecting a response, so I stayed quiet. “So, tell me, Josh, did you leave that mess on purpose because you wanted a spanking?”

There was no point in lying to her now. “Yeah, I did.”

“Have you ever been spanked before?”

“No, never.” I replied honestly.

“And, did you like it as much as you thought you would?”

I hesitated for a second before admitting that I did.

“I could tell. But just so you know, there are a lot of other punishments besides spankings in my repertoire. So I suggest you behave yourself….” I felt Diane step in close behind me and rub one hand over my ass. “...But I hope you don’t.” ‘Slap!’ I jerked at the sudden slap to my already stinging ass. “You may leave the corner.”

I waited for a second for Diane to leave the room before I pulled up my pants and ran to my room. It was less than five minutes later when I found myself jerking off in my bathroom (Thankfully I had my own en-suite.), thoughts of Diane spanking me running through my mind as I came.

—

“Good morning, sunshine.” Diane greeted me brightly as I entered the room the following morning.

I blushed a little at the memory of the previous night when I saw her. “Morning.”

“How’s your ass today?” She asked with a playful smile.

“It’s….fine. It was pretty sore for a while last night though.” I said.

“Haha, well just be thankful I didn’t use my paddle.” Diane replied with a wink.

“Wait…you have a paddle?” I couldn’t help but ask.

“Of course I do. I have lots of fun toys.”

“Guess I shouldn’t be surprised. There’s no secret BDSM dungeon in the basement, is there?” I asked, trying to act as though I was as unfazed about the whole situation as she was.

“Unfortunately not, no. Just a black suitcase hidden under my bed. But if I were you I’d stay out of there, unless you want to find out what some of the items in there are used for.” Diane excused herself after that comment and I couldn’t help but wonder if that was another challenge. Did she want me to go looking in the suitcase? Was that her way of getting me to admit that I wanted to find out exactly what was in there?

Later that same evening I found myself alone in the house while Diane went out for a few drinks with her friends. Naturally, all I could think about were the contents of the suitcase she had hidden under her bed and what she said…’Just a black suitcase hidden under my bed. But if I were you I’d stay out of there, unless you want to find out what some of the items in there are used for.’

Screw it! I don't know what kind of weird, kinky turn my relationship with my landlady had taken, but I was way too intrigued by what she had said to let the opportunity pass me by. I walked into her bedroom, and saw the large, king-sized bed that dominated most of the floor space and saw that there was indeed a bunch of stuff underneath. Sure enough, among the boxes and bags there was a large, black suitcase.

I pulled it out and dropped it onto her bed, hearing metallic clinks and dull thuds as the items inside shifted around. I noticed the zipper had a built-in combination lock but it was left open and I wondered if Diane had opened it on purpose before she left.

The sound of the zip was loud in the otherwise silent bedroom and I flipped open the lid to see what was inside. “Fuck!” I said out loud as I took in the contents. There were a couple of dildoes and what had to be a strap-on harness, some butt plugs ranging in size and color, various straps, chains and buckles as well as some sexy looking clothes, including a black and white maids outfit with a short, petticoated skirt, a few pairs of ultra feminine and ruffled panties plus some bras. I picked up the paddle she had mentioned, it was thick and made of stiff, black leather but had the word ‘SLUT’ cut out, designed to leave an imprint on the victims behind. There was a small, black drawstring bag half buried among the other items but I left that as it was, too taken aback by everything else I had seen.

I returned the suitcase to what I thought was exactly where I found it and wondered if Diane would know I had been snooping.

Diane returned a while later while I was watching a movie on my laptop in my bedroom. I heard her moving about outside my room but she didn’t enter to speak to me. She had a pretty good respect for boundaries for her lodgers so if my door was closed she would leave me alone.

‘Knock knock knock’ “Josh? Are you awake? Can I come in?” Her voice came through the door.

“Yeah, it’s fine.”

The door opened and Diane was there, smiling that layered smile that said she knew something I didn’t. “Has someone been a naughty boy again?”

For some reason, hearing those words caused my cock to stiffen slightly, thankfully it was hidden beneath my bedsheets. “Who, me? I don’t know what you’re talking about. “

“Oh really? So you weren’t snooping around in my room. Under my bed?” She asked, her arms crossed.

“I wouldn’t dream of it.” I replied, trying to look offended.

“Then would you please explain to me why the contents of my suitcase were all over the place when I checked on it just now? I should have known a bad boy like you wouldn’t have been able to keep away.”

“You got me.” I said. “I’m sorry. I just couldn’t help myself. When you told me about the suitcase I just had to know what was inside it.” That part was the truth.

Diane let out a sigh and then left, leaving my door open and without a word. I wondered if that was it and felt a little disappointed. There was a part of me that was hoping for another spanking or something along those lines. For a moment I thought maybe I had misread the situation and offended her in a real way, so I got out of bed and headed to her room to apologize, but I didn’t get far.

“Where do you think you’re going?” Diane asked, reappearing in my doorway.

“Umm, I was coming to apologize for-for snooping.” I said, noticing the bundle of cuffs and straps she had in her hand.

“Oh it’s too late for apologies, Mister. Get back on the bed, now.” She pointed over my shoulder to the bed and I did as she said without offering any resistance.

Diane made sure I was lying on top of the sheets which meant I wouldn’t be able to hide my growing erection, but I’m pretty sure she was counting on that fact. Cuffs were fastened to both my wrists and attached to opposite sides of my headboard, attaching me firmly to the bed. “Now you’re stuck and at my mercy.” Diane said with a devilish look in her eye. “Time for your punishment.”

I panicked a little as Diane pulled down my pyjama bottoms, exposing my cock to her for the first time. “Someone seems excited to be punished.” She said, before adding something that made me blush deeper than ever before. “Does it get much bigger than that?”

“Hey!” I said, equal parts offended and embarrassed.

“Hahahaha, it looks like a cock, but smaller.”

“Diane!” I whined and tried to twist my hips away to hide from her insults, but if anything they only made my cock harder. A fact that Diane seemed to notice.

“Aww, does someone like having their little cock made fun of?”

“No!” I said, feeling like that was supposed to be the answer I should give, but the truth was there was something thrilling about it.

“Liar! I can see your little guy twitching. Is this why you never bring any girls home? Are you scared they’ll see your tiny little cock and leave.”

I scrunched my eyes closed in humiliation at her words but my traitorous cock wouldn’t go down in the slightest. Then I felt her take hold of my cock and my eyes widened.

“Aww, it’s okay, little guy. Let Mommy Diane take care of you.” She started stroking up and down in a slow rhythm. “It’s good that it’s so small. Means I only have to use one hand to do this.” I squirmed on the bed as Diane kept stroking and teasing me.

“Mmm…Diane, please.”

“Oh don’t act like you’re not loving it. I should have known as soon as I felt your little stiffy when I spanked you that you were a little subby boy who gets off on being humiliated.” She kept stroking at a slow, teasing pace. “Tell me, Josh, how many times have you jerked off since you moved in here?”

“What…I…I don’t…” Could I really have denied it? Would she believe me if I did?

“Oh please. You haven’t been on any dates or brought any girls home and you’re how old? Twenty two was it? So…How many times?”

“I don’t know…a few, I guess.”

“A few, huh, thought so. I’ll bet you’d like me to finish jerking you off, wouldn’t you?” Her hand sped up on my cock.

“Yes.” I gasped as she brought me closer to orgasm.

“But that wouldn’t be much of a punishment, would it?” She asked, still pumping my cock. “Me making this little dick cum wouldn’t teach you a lesson, would it?”

“Nnn-no…I guess not.” My body tensed as I felt the orgasm approach and then…nothing.

Diane removed her hand and all sensation stopped, just as I was about to go over the edge. I pulled at the straps holding my wrists to the bed, if my hands were free I would have been finishing myself off. “Fuck!”

“Hahaha, sorry, Josh.” Diane said in a tone that suggested she was not sorry at all. “Don’t go anywhere.” She disappeared and left me strapped to the bed, rock hard and desperate for touch. I was a little surprised to see her return with a cloth that was dripping with water….was I about to get a bed bath of some sort?

“Ahhhhgg! Shit. C-c-cold, cold cold!” The cloth was freezing cold and Diane had just dumped it right on my crotch. She used her hands to hold my hips to the bed so I couldn’t shake the cold cloth off of my junk and a few minutes later it did its job. My erection was gone, shrivelled to nothing by the freezing cloth.

Diane lifted up something I hadn’t seen before, the black bag from her case. She emptied the contents onto the bed beside me. I saw rings of different sizes and three small, vaguely cock shaped cages in three different sizes.

It took me a second to realize what they were, but when I did I panicked and pulled on the restraints. “Oh fuck.”

“Ah so you know what these are? Good, that will save me an explanation. I doubt we’ll be needing these two…” Diane picked up the largest and the second largest cage and placed them back in the bag, leaving her with just the smallest of the set.

“Diane…please! Can’t you just spank me again?” I asked as she picked up the different sized rings.

“Oh I think not. I told you that if you went snooping through that case then you would find out what was inside, and you still went and did it. Now hold still.” Diane peeled back the cold cloth and laughed again. “Hahahaha oh dear. And I thought it was small before, hahahaha.”

With a little squeezing and pulling on her part, she got the silver base ring behind my package and began carefully sliding my cock into the cage portion. The barrel was attached to the key and Diane slid it inside slowly, teasingly. ‘Click’

She had a cheshire cat grin as she turned the key and locked my cock away. “No jerking that small cock with this, is there? Hahaha.” Diane packed away the rest of the chastity cage parts and began undoing the straps at my wrists. “Well, it’s getting late and I need my beauty sleep. Goodnight, Josh.”

“Wait, you…you’re just gonna leave this here?” I asked, looking down at my caged cock which was already trying to get hard again.

“Of course I am. You’re being punished, remember?”

“How long for?” I asked.

“As long as I decide. Obviously.” Diane made it sound so simple, as though she hadn’t just locked my cock away from me.

“But…I have work tomorrow.” I said.

“Oh, right…Then I suggest you don’t show anyone your cock while you’re there. Not that there’s much to see, hehe. Night.”

Well, I have certainly done it now. I had poked the bear, so to speak. I had wanted this, wanted to find out what was in that bag, wanted her to punish me on both occasions, what is it they say? Be careful what you wish for….

End part 1.