Owned by the Landlady - 7 (Patreon)

Owned by the Landlady - 7

Josh - The wheel of Misfortune

Diane was standing near the slightly messy panty drawer, telling me about how I deserved a punishment for it, I myself couldn’t believe that I would be punished over something so trivial.

“Punished? For that? I can fix it in like two seconds.” I protested. “It’s just a few out of place panties.”

“If you can fix it in two seconds, then you should have done it earlier. Add this to failing to wear your full uniform and I have no choice but to punish you. Can’t have a maid being sloppy after all.” Diane had that same playful smile on her face, even as she admonished me.

“Okay, fine. Punished how?” I asked, half afraid, half curious to hear the answer.

“Well, I’m not entirely sure. I have a few ideas, but I’m not sure which idea would be best. It could be an extended chastity sentence, maybe a new alteration to your outfit, a good old fashioned spanking….I imagine you’ll be getting used to them before too long.” My cock twitched at her words, seemingly excited about the possibility of DIane punishing me. I told myself it was just because I was so bored with not much else to do.

Diane perked up before speaking again. “I have an idea! But that will have to wait until later, for now I have a date to get ready for.”

My heart dropped a little at the word ‘date’. I know it was ridiculous, it wasn’t like we were a couple or anything of the sort really, if anything I was more just a toy for her to use. “A date?” I asked, trying, and failing, to sound non-plussed.

“Yes, a date.” Diane had a wicked smile as she seemed to pick up on my disappointment. “Why? Does that bother you?” She asked.

“No!” I answered too quickly. “I mean, why would it? You’re a good looking girl-err-woman, you deserve to go out and….whatever.”

“Hahaha, well thanks, I guess that means you’re off the hook for now though. But I won’t forget about that punishment mister!” Diane skipped happily across the room, leaving me alone, dressed as a maid and trying to reconcile the disappointed feeling I had got when she said she had a date.

—

Later that afternoon, when I was back in my own clothes (besides the panties) Diane called me into her room. I paused the game I was playing and headed across the hall. “Hey you called-Woah!” Diane was standing in her living in nothing but a tiny black thong and matching bra that pushed her chest up to an inviting and eye-catching cleavage. I quickly turned my head away. “Sorry, you called me?” I said.

“Yes, and you can stop looking away, I need your opinion.”

“Right, okay.” I slowly turned my head back towards her, she looked amazing in just the small black underwear set and I could already feel my cock swelling in my shorts. Diane was holding up two dresses, similar in style but two different colours, one black and one a deep blue colour.

“Which do you think looks better, this one?” Diane brought the blue dress in and held it close to her body, covering her almost nudity from view. “Or this one?” The blue dress was held aside, giving me another seconds view of her underwear before the black one replaced it.

I knew absolutely nothing about women’s fashion or what would look nice on who, so I simply said, “I’ve always liked the look of a black dress.”

“Great, black it is.” Diane hung the black dress up over her wardrobe door and put the blue one back inside, leaving her standing there in just her underwear while I tried not to seem like I was ogling her. “Now, one more question, and be honest. Does my ass look good in this underwear?” Diane then turned away from me and stuck out her ass slightly, almost causing my mouth to drop open.

Her ass was, as I already assumed, amazing. She had caught me staring in her tight leggings more than once so I knew she knew what she was doing when she flashed me her behind in only the tiny black thong. Her hips were wide, carrying a little extra weight but her ass was extremely well proportioned, round and with a nice amount of jiggle that made it seem soft. Then she popped up onto her tiptoes and her ass muscles clenched, which only made it look more round, more supple.

“Josh!” Diane said, snapping me out of my daze.

“Right, sorry. It looks great.” I said, trying not to show how aroused I was by the sight of her, unfortunately, the tent in my shorts was doing that for me.

“Haha, well, I can see you’re not lying at least.” Diane said, giggling as she glanced down at my crotch.

“Shit, sorry, that’s not….” I had no excuse to bring to mind.

“Not what? Not your little dick getting hard at the sight of me in my underwear? Are you turned on by my ass or are you jealous of my panties? Maybe you’d like a pair of your own.”

“Shut up!” I said, turning to head back to my room before she could take any more shots at me.

Diane called me down to the living room a little later when she was ready to head out for her date. I entered to an absolutely stunning sight. Her face was made up with classy, elegant makeup and her hair was tied up in a fancy style with curls running down the sides. Now that the dress was on her, I could see the deep neckline exposing a generous amount of cleavage. Her legs were covered by sheer nylon hose that gave them a shiny, soft look before they disappeared into a pair of calf-length boots with a high heel. I knew she was attractive but this was something else.

“Wow…” The word left my mouth before I could stop it.

“I take it you approve?” She said, a cocky smirk on her face.

I couldn’t deny it. “Definitely, I’m a little jealous of whoever gets to take you out.”

“Oh, you flatter me, sir. But it’s just an old friend and a few drinks, we’ll see what happens. I’ll let you know if I get lucky so you can put on your headphones. Ha.”

I felt another pang of jealousy at her words. “Ha, thanks for that. You scrub up well.”

Diane left shortly after, leaving me to wonder if she would in fact ‘get lucky’ or not.

—

It was sometime around eleven when I heard the front door open and close. I listened intently but there was no sound of anybody with her, and I found myself becoming a little relieved at that. I made a mental excuse of getting a drink to head downstairs before she disappeared into her room.

“Josh, is that you?” There was a slight slur to her words as her voice came from the living room.

“Hey, sorry, just getting a drink. How was your date?” I asked, stepping into the room to see her struggling to remove one of the boots.

“It was okay, at least it started okay. We drank, we ate, we made out and fooled around in his car. Felt like a teenager again, ha.” She said, giggling a little.

“Sounds…fun. So how come you’re home alone? Only a fool would turn you down looking like that.” I said, honestly.

“Well, I managed to cop a feel of what he was packing, if you know what I mean. But, well…it was wayyyy too big!”

“Woah, okay, gross. I don’t think I need to hear that.” I said. The last thing my confused and horny brain needed was to hear her describing how big another man's dick is.

“Why not? You asked, I told.” Diane made another failed attempt at removing her boot before she flopped back onto the couch cushions. “Joooosh, I need your help.” She said in a whiny voice, clearly a little drunk.

“Okay, fine, I’ll help.” I knelt down in front of her and grabbed her shoe and started pulling on the soft, tight leather. “Are these real leather?”

“Of course! Only the best. Still didn’t get anything though, all that effort wasted.”

“Well you had a good time at least. At least it certainly sounds like you did.” I replied, carefully working the shoe off her foot to expose her nylon clad feet with painted toenails beneath.

“Ahhhh, that’s better!” She said, sounding relieved as she flexed her toes in front of me. “Hope they don’t smell too bad, hahaha.”

I did catch a faint whiff of something when I pulled the shoe free, but it certainly wasn’t a bad smell, feminine, her. “Nah, you’re fine.” I said, grabbing the other boot and starting to work this one free.

Diane gave a loud, exaggerated sigh. “Why couldn’t I find a guy with a nice, cute little dick?.....Like yours!”

“Hey, I told you mine isn’t that small.” I replied, noting how her other, boot free foot, was sliding towards my crotch.

“Haha you said that small that time. So you admit it is at least a little small?” She said, her foot inching closer to my groin.

“What? No that’s….that’s not what I meant. It’s not small, at all.” I pulled the other shoe free and caught that same odor again.

“Ahhh, that’s better.” She said stretching her leg and giving me a view right up her tight skirt at the black thong she had modeled earlier. I found myself unable to look away, thankfully, DIane was too drunk to notice. “You shouldn’t be embarrassed by your little penis, Josh, some women like that. I loooove cute little cocks like yours. So much fun to tease…” As she said the word ‘tease’ her nylon covered foot brushed against my erection, sending a jolt of pleasure through me.

“Ahh.” I gasped in shock and pleasure at the sensation but she didn’t stop. Her foot kept moving up and down and around the area where my cock was tenting beneath my shorts.

“See, your little guy likes it when I tease him.” Diane pressed a little firmer on my erection and I knew if I stayed there, with her foot rubbing my cock and being able to see right up to her panty covered sex then I would eventually be cumming in my underwear.

“Diane….I think we need to get you to bed.” Part of me wanted to stay there, to have Diane rub my cock with her feet until orgasm. But she was drunk and it just didn’t feel right. “You’ve had a lot to drink.” I said, standing up and trying to tuck my erection into the panties waistband so it was less obvious.

“You’re right, Josh. I guess I’d better go to bed, looks like my vibrator will be getting a workout tonight, hahaha.” Diane laughed as she stood, unsteadily and stumbled towards the stairs. I followed her to make sure she didn’t fall on her way.

“Can you unzip this?” She said when she was standing near her bedroom door.

“Sure.” I grabbed the zipper at the back of her dress and pulled it down, only for Diane to shrug it off her shoulders and let it pool on the floor at her feet. I was treated to another view of her ass in the tiny thong as she stumbled towards her bed.

“Don’t worry about that,” Diane said, pointing to the dress she had left outside her bedroom, “the maid will get it in the morning, hahaha.” I closed the door, my heart pounding and my cock throbbing. I picked up the dress, it looked way too expensive to leave in a heap on the floor.

—

If Diane remembered anything about last night, she didn’t mention it right away so I decided to ask. “How are you feeling this morning?”

“Ugh, my head hurts. Did I talk to you last night?” Diane asked as she sipped on a glass of water.

“Yeah, I had to help take off your shoes…..and your dress. I hung it in the bathroom, by the way. Didn’t want it to get ruined on the floor where you left it.”

“Aww, I knew you’d make a good maid.” She said, smiling. “I hope I didn’t do anything too embarrassing, I tend to get super horny when I’m drunk. Coming home alone can’t have helped.”

I thought about telling her what she had said, but decided to spare her the embarrassment. “Nah, you were fine. Drunk, but fine.”

“Oh good, you didn’t try to take advantage of your drunk landlady did you?” She said in a playful voice.

“Hmm, I thought about it but I figured I’d be the gentleman this time.”

“Well that’s good to know, cause I can be insatiable when I’m drunk sometimes.”

“Ha, note to self: Buy Diane some whisky.” I joked.

“If you want to get into my panties….in the figurative sense that is, ha, then gin is the way to go.” Diane laughed at her joke about getting ‘into her panties’.

—

Later that day was more of what had somehow become typical for me. I got dressed in the maid uniform at eleven am and Diane followed me around, giving me ‘helpful advice’ now that she had sobered up a little.

“Remember to bend at the waist.”

“Keep those legs straight, sissy.”

“Don’t forget to curtsey.”

“You’re supposed to call me ma’am when you’re on shift.”

This went on until the end of my maid shift when I was looking forward to getting out of the chastity cage, but Diane spoiled that plan.

“Josh, could you leave the cage on? We need to discuss your punishment from yesterday.” Dammit, I had forgotten about the mention of an extended chastity sentence being a possibility. Everything Diane did seemed to turn me on somehow.

I removed my work outfit but left the cage on, wondering how long she might sentence me to as I headed to meet her in her bedroom. Much to my disappointment, she was fully dressed this time when I entered.

“So, what’s the verdict?” I asked as casually as I could.

“Well I had so many fun ideas in mind that I just couldn’t decide….that’s why I bought this!” Diane stepped aside and gestured to a plate-sized spinning wheel, separated into five small, different colored segments, like a pie-chart. It was held upright on a stand and designed to spin, with a small black arrow acting as a stopper at the top; it was a chance wheel, like you see on a gameshow but there were no prizes, or anything inside the five segments.

“Umm, are we playing a game?” I asked, looking at the wheel.

“Something like that. I figured that instead of deciding myself how to punish you, I’d just let the wheel decide for me.” Diane popped the cap off a dry-wipe marker pen and began to write in the first segment of the wheel. “The first one is easy.” She said as she wrote the words ‘Chastity for forty eight hours’. “And so is the second one.” Diane wrote one word: ‘Spanking’.

“But the last couple are where I’m struggling. I guess I could go with….” Diane wrote the words ‘Change of dress code’ in the third section, followed by ‘Writing Lines’ in the fourth. “There, now that’s looking good to me, but there’s one more section left. If you agree to go along with my game, then I'll leave this one as a freebie, whaddya say?” Diane asked.

I could tell she really wanted me to play along with this game, so I decided to try my luck. “Hang on, how about this…” I stepped forward and plucked the pen from her grasp and wrote the words ‘Day off work’ in the blank section. “There. I’ll play along, but this way I get the chance for a reward.”

“Deal!” Diane offered me her hand as I once again made an insane deal with my Landlady. “Okay, Josh. Go ahead, let’s let fate decide your, ummm, fate”

“Let’s do it.” I braced myself and gave the wheel a strong spin, watching as the colors swirled and blurred together to the tune of a rapid ‘click, click, click, click’ as each section passed the winning arrow.

Diane and I both watched intently as the clicks slowed down.

‘Click….click……….click……………click’

“We have a winner!” Diane said gleefully as I read the outcome. ‘Writing lines’.

“Writing lines…..doesn't sound so bad” I said, thinking that it could have been much worse.

“Well I'm glad you think so. I'll go get things ready downstairs.” Diane waltzed happily out of the room to prepare for my punishment.

While inconvenient and annoying for sure, writing lines didn't seem like the worst punishment in the world….

—

I met Diane downstairs, seeing that she had set up a small desk and chair facing the wall of the living room, on which sat a notepad and a pen. I tried not to laugh at the ridiculous nature of this punishment. Truth be told, I was hoping for something a little….naughtier?

“Okay, time to get started with your punishment, mister. Take a seat.” Diane was sitting on the sofa, so my back was to her when I sat down.

“So should I call you Miss Ryan while I’m doing this?” I said.

“Whatever floats your boat. Call me whatever you like, just make sure you complete your punishment” Diane replied. “I want you to write ‘I have a tiny cock’ one hundred times.” I could hear the grin in her voice from behind me.

“Seriously with that, again?!”

“Yes, this is your punishment. I’ll be checking your work after, any mistakes and you redo the whole page.” Said Diane.

There was no point in arguing, so I simply said, “Yes, Miss Ryan.” In my best imitation of a school boy.

I grabbed the pen and wrote the first humiliating line.

‘I have a tiny cock’ I paused after the first line, the mathematician in me coming to the surface. If one line takes approximately seven seconds, then a hundred lines takes 700 seconds. Divide seven hundred by sixty and I could be finished in a little less than twelve minutes….

‘I have a tiny cock’

‘I have a tiny cock’

I kept writing, twelve minutes was nothing really.

‘I have a tiny cock’

‘I have a tiny cock’

‘I have a tiny cock’

Was my cock really that small? My mind started to wander as I wrote the same four words over and over. No, she’s just messing with me, trying to twist my thoughts so that I agree with her own humiliating assessments.

‘I have a tiny cock’

‘I have tiny cock’

It wasn’t that small. That’s what I had said last night….could that really mean that I was starting to agree with her? I quickly got through the lines before the humiliating words could burn themselves into my mind, which I guessed was her plan for this task.

‘I have a tiny cock’

‘I have a tiny cock’

“I think I’m done.” I said, turning to see Diane idly flipping through a book behind me.

“Great, let me see….” She stood behind me and peered over my shoulder, her breasts brushing against the side of my head, teasingly. I made no move to correct this as my penis stirred in my shorts.

“Josh, what were you supposed to be writing?”

“Umm, I have a tiny cock.” I answered.

“Exactly, but on this line here, you missed the ‘a’. Start over.” She flipped the page of the notebook to a fresh one and dropped back on the table in front of me.

“Start over? For one letter?”

“Yes. You knew the rules. Be a good boy and finish your punishment properly.”

I bit back my protest and started again.

‘I have a tiny cock’

‘I have a tiny cock’

‘I have a tiny cock’

I took a little longer on each line, making sure not to make any mistakes. I was so focused on spelling the words correctly that I found myself subconsciously mouthing the words in barely audible whisper. “I have a tiny cock.” I mentally berated myself for saying it out loud, all the while my tiny cock was getting harder in the panties.

‘I have a tiny cock’

‘I have a tiny cock’

“I have a tiny cock.” Sitting on a chair, facing the wall, wearing panties and writing one hundred times that I have a tiny cock. How did I let this get so far? How much longer before Diane completely eroded my masculinity? Why was I making it so easy for her?

‘I have a tiny cock’

‘I have a tiny cock’

It was easy because she was my lifeline right now. She had money, a place to stay that meant I could stay on staff when work resumed. I was just doing this stuff to keep her sweet, that was all. Nothing more to it than that…..Just harmless fun.

“Aaaaand, I…have…a…..tiny….cock. Done!” I said, reading the last line out loud as I slammed the pan down on the table and rotated my wrist around. Diane appeared behind me again, poring over my writing and again her breast rubbed against the side of my head.

“Hmm, well the handwriting is a little sloppy in some places….but no mistakes this time. I’ll give this one a B minus. B for babydick, hahahaha.” Diane chuckled at her own joke.

“Does that mean I’m finished? My wrist is hurting.” I said.

“Well that depends, what did you learn?” She asked.

“Umm, not to mess up my panty drawer.”

“And?”

“That I should always wear my full uniform when I’m working, including the chastity cage.”

“Aaaand?” She was grinning down at me, holding the page filled with my lines in front of my face.

I knew what she wanted, and I wanted out of this chair, I had a cock that needed attention. “That I have a tiny cock.” I said, defeated.

“Hahaha, Well done, Josh. It’s about time you admitted it. You’re free to go.” Diane wandered out of the living, notebook in hand.

I was glad to be out of the chair and prepared to head upstairs, but not before grabbing a drink from the fridge. That was where I saw Diane, using a magnet to stick my page of lines to the fridge door. “You’re not seriously leaving that up there, are you?” I said.

“Of course I am. This is my fridge, I can put what I want on the door, and if you remove it without my permission then there’s another punishment in it for you.” Diane walked past me and slapped my ass on the way by, chuckling to herself. I grabbed my drink and headed up to my room.

It wasn’t long before my hand found its way into my panties and started stroking my cock. The humiliating words kept popping into my mind as I touched myself. ‘I have a tiny cock’

The more I tried to shake them away, the more prominently they appeared. Here I am, a guy in panties stroking his tiny cock. ‘I have a tiny cock’ ‘I have a tiny cock’

“Fuck!” I gasped out loud as I came, the words almost leaving my lips as I filled my panties. Did Diane really like tiny cocks or was this just a way for her to mess with me? If I thought she liked tiny dicked guys then I would be more open to filling that role for her. But did she want me to fill that role? Maybe she just enjoyed messing with guys, teasing them.

‘I have a tiny cock’

End part 7