Landlady from Hell

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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ValerianXIII
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Landlady from Hell

Post by ValerianXIII »

This is my one and only ENM story for now. Trying to get back into writing and have decided to post some of my unfinished stories to see if there is any interest...




Part 1

It all started a year after high school. A few of my buddies and I had a big plan to move into an apartment together and split up the rent. The apartment we found ended up up being in a few states over and we managed to get are money together and get moved in rather quickly.

Looking back it seems like a dumb idea but at the time it didn't seem that way. We all were going to get jobs split all the bills, party do whatever we wanted. The first week or so everything was great. We managed to land some minimum wage jobs and finally had true freedom for the first time in are lives.


But as the month went by problems arose. One friend lost his job and had to move back home while another was so irresponsible with his money that he couldn't afford to pay anything. By the time the first month ended it was just me stuck with the rent and all the bills on my minimum wage pay.

There was know way I could do it and everything with the apartment fell apart just as quickly as it began. While my friends had somewhere to go back to I didn't have anything. My parents had left the country and at this point I was stuck in a strange town with almost no money left. I looked up other places for rent and discovered everything was way out of my league.

It wasn't until I came across a lady that rented a room at a price I could afford. It was cheap, real cheap actually she just insisted on clean living and chores. But I didn't care at this point I was desperate. I called the lady up and she sounded like a sweet old lady over the phone. She made me to agree to a few things that I hadn't really paid attention to and before I knew it I was in a cab with my few belongings in a backpack.

The home was old fashioned in a slightly wooded suburb with a fenced in yard. The woman introduced herself as Miss Rose and she was in her late sixties. Miss Rose was a heavy set woman and a bit taller than me as as well. She was big all around really. Big chest, big butt, thick leg and thick arms. I couldn't help but notice as she gave me a guided tour of her rather large old fashioned home.

She was a no nonsense woman with a rather serious disposition. Anytime I tried to speak I was quickly interrupted as she just carried on. The old wooden house had some rather spacious rooms all the way until we ended up at mine. It was barely twice the size of a walk in closet with just a twin bed and a small dresser. I was pretty disappointed and a bit surprised after seeing the rest of the house at this point. It didn't even have window with only one light coming from the ceiling. I sighed at this but thought at least it was something.

Miss Rose had me pay my initial rent which at that point was everything I had left. We discussed my work schedule and it was revealed that I would be off tomorrow. She seemed to be happy about that for some reason although it was hard to tell through her blank expression. Without a penny to my name and just a handful of clothes I tried to get comfortable in the small stuffy room. Right away I discovered the door had no lock and would barely stay closed. I didn't bother with the dresser leaving my bag of clothes on the floor before laying on the bed and drifting to sleep...
Last edited by ValerianXIII on Thu Jul 06, 2023 1:30 am, edited 1 time in total.
TeenFan
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Re: How my Landlady kept me in line

Post by TeenFan »

Big old house with a big lady. Could be big problems.
Not much to go on yet, for what type of story this will turn out to be, but I doubt it's a comedy.
Perfect type of room to have a two way mirror over the dresser for the big lady to spy on him.
I suspect the lady might have some interesting toys and outfits in a room that is LOCKED.

This old lady wasn't tall, but I can imagine this to be like one of the many movies that Bette Davis did in the 1960's where she did her
creepy older lady character. "The Nanny" is a classic to look up. The nutty woman keeps wanting to give the 11 year old boy his bath.
The boy knows she really wants to drown him.
ValerianXIII
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Re: Landlady from Hell

Post by ValerianXIII »

Part 2


The next morning I awoke suddenly with my bedroom door bursting open. Miss Rose came in and I was still dressed in my clothes from last night besides my shoes as she began to dictate what was what. It must of been around 5 am and she already had a whole list of chores for me to do. I was so confused and drowsy at that point I didn't know what to say.

Before I could come to terms with what what was going on I found myself outside pruning the bushes under her watch. She had me go around the house manicuring her hedges until they were perfectly even using only the outdoor lights. I just couldn't believe how picky this woman was as she over saw my work making sure it was perfect.

Next I came inside where I thought I might get a break but was only met with more chores. I found my self vacuuming each carpeted area until it was spotless with Miss Rose right behind me the whole time. Then she had me dust. I had never dusted in my life and found something about it to be quite embarrassing. Little did I realize that was just the beginning to that feeling.

Afterwards I was given a quick breakfast of rather bland sugar free oatmeal before being put back to work. The rest of the day was much of the same. Slaving away cleaning every inch of that old house up to Miss Rose's impossibly high standards.

Around lunchtime is when things started to take a strange turn. I was told before I could eat I would have to take a shower and get changed. Although my stomach was growling I was quite sweaty and filthy and hadn't showered since I had arrived. Miss Rose lead me to the end of the hall just passed her bedroom where a small bathroom awaited. I noticed immediately the wooden door wouldn't lock and would barely stay closed. I made due assuming that's the way these old houses were and hopped into the shower leaving my clothes and backpack on the floor.

The water was rather pleasant and I enjoyed the little break. A few minutes in though I could swear I heard the old bathroom door creak open. Once I felt finished I stepped out of the shower and was shocked to see my things were gone. Instead of my back pack there was a set of clothes with a shirt shorts and what I would call tighty whitey underwear along with a small barely adequate towel. I used it to dry off eyeing the rather childish outfit presented before me.

Why would she take my clothes? I wondered some annoyance. I considered for a moment just wrapping the towel around my waist and searching for my clothes but I found the towel to be to small and flimsy barely able to stay in place. So I swallowed my pride donning tighty whities for the first time in almost a decade. There were really snug containing my my crotch and riding up my butt uncomfortably. The baby blue shorts were similar in a way. Ending four or five inches above my knees without any pockets at all.

The shirt was short as well barely reaching my waistline. It was only temporary I thought at the time. I told myself I would wear them just long enough to find my real clothes. I checked my room and there was no sign of my bag or anything so I made my way to the living room to confront Miss Rose.

It was hard to be defiant or demanding in those clothes, I realized almost immediately. Miss Rose sat comfortably praising my outfit before I could utter a word. Her eyes were fixed on my blue shorts eyeing them like a crocodile eyes meat when I finally asked. "Miss Rose where are my things...where are my clothes?"

Miss Rose seemed rather dismissive of the question. "Oh those things were so ratty and disgusting! I threw them in the.. wash." She answered although it seemed like a lie even then. "Really you look so much better now with clean clothes that fit properly. Now go have seat at the table I have some lunch waiting."

I did so reluctantly with my stomach growling from the small breakfast. I ate another small lunch and it just didn't seem like enough after the hard morning. This time Miss Rose had me wash not only my dishes but all the dishes that were dirty at the time. She took a seat behind me as I washed and I couldn't help but feel her staring at the back of my shorts the whole time while she slowly sipped coffee.

I was feeling quite ridiculous in my current outfit but any question s about my clothes were quickly shushed as I was put back to work. I was handed a mop, bucket, floor cleaner and a scrub brush. I held the mop in one hand while the full bucket in the the other. I was told to follow Miss Rose and I did so with a sigh.

We entered her bedroom which was quite large and luxurious. I had little time to study it though as I was shown to her personal bathroom were I was instructed to clean every inch. I looked at Miss Rose with my mouth wide open in disbelief but she could care less leaving me to work for the moment. She returned moments later literally standing over me as I cleaned the the space between each tile. As if she was going to ride me like a horse with each foot on each side of me.

When it came to scrubbing the toilet I felt as if she was going to shove my head in and give me a swirlie by the way she hovered close above me. By the time I was through it was dinner time and I was surprised to see it was already getting dark. After a quick dinner I was ordered to bed although I wanted to argue I found myself just too tired to resist.

I returned to my small room still wondering about all my things when Miss Rose burst through my door suddenly holding an empty laundry basket. She informed me that it was for my current clothes even my underwear. She told me my work uniform would be ready in the morning. She tossed a fresh pair of tighty whities on the bed.


I really felt strange shyly stripping down and getting into my new tighty whiteys with the possibility of Miss Rose bursting in at any minute. I wanted to object but I was just so tired at the time. I complied with her demand getting under the covers before she abruptly entered snatching away my clothes leaving me with only a pair of briefs to my name. She clicked off the light and I realized just how vulnerable I was as I drifted of to sleep in the pitch black room....
ValerianXIII
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Re: Landlady from Hell

Post by ValerianXIII »

Part 3



The next Morning I was woken up with Miss Rose suddenly bursting through my door and the bright light in my eyes. "Get up! Get up! Get up!" The heavy set woman chanted while clapping her meaty palms together. I was so confused and still tired i had know idea what was going on or what time it was.

I started to pull back the sheets and blanket only to remember I was still only dressed in my rather tight white undies and nothing else. I suddenly became modest diving back under the security of the thick blanket.

"Hurry up now! Get up!" She barked rushing me out of bed.

"But..but Miss Rose I'm ...in my my my .."

That was where she cut me off before I could finish. "Your undies. Yes I know and frankly I could care less. I have seen plenty of boys just like you in there little undies and even less. Believe it or not I have never been impressed by any any of it." With that said Miss Rose took hold of the blanket and sheets ripping them off the bed and my body bringing a cold chill across my underwear clad form.

" Just as I thought nothing to hide and certainly nothing to proud of." She said cruelly eyeing my body up and down as i lay there in surprise. "Come on sleepy head out of bed and into the kitchen before your breakfast gets cold." I couldn't believe she expected me to walk around like this and I asked right away.

"Do you have anything for me to wear. I can't just.." She cut me right off though "Oh pish posh your work clothes will be done soon enough and you certainly can eat breakfast dressed just as you are." Even though she was so dismissive about everything her eyes were scanning me all over as I meekly climbed out of bed in nothing but my tighty whitey's.

The house seemed colder than usual and I could feel my testicles and penis shrinking and shriveling as I walked towards the kitchen with Miss Rose seemingly breathing down my back. I was met with a bowl of warm oats and the wooden chair felt like it was made of ice as I sat down on it. I scarfed down the bland bowl and then washed my dishes in the sink as I could feel Miss Rose staring at me the whole time once again.

I was starting to shiver a bit and I once again requested some clothes but was quickly denied and told that my clothing would be coming out of the dryer soon. I could see the hint of a smile across her face the moment she denied me my clothes as if she enjoyed it somehow.

Instead of clothing I was given a vacuum and made to use it on her living room rug while she sat directed and watched from her chair.

I really wanted to protest. I wanted to demand my clothes before I did anything but it was hard to be defiant dressed in only tight fitting undies and I was so exhausted from the previous day.

Finally she told me my clothes would be ready as soon as I got out of the shower. It felt like I was being told to shower and that sort of bothered me but I needed to take one anyway. I could swear the water wasn't quite as hot as the day before almost lukewarm even when I turned it all the way up.

Miss Rose didn't hesitate to enter while I was in there once again dropping off my folded clothes and a fresh towel. It was a strange feeling being completely naked with only a plastic shower curtain separating me from this strange woman.

I had never felt so happy to be in that awful fast food uniform and to be honest it had never been this clean. My work day went along pretty uneventfully although I was tired and dragging along most of the day. I was happy to be dressed and out of that house for a while and wondered at times what I had gotten myself into.

For now though it was still the for the best but I really needed to put my foot down. The city bus dropped me off and I walked the cool and breezy mile to Miss Roses home. My clothes reeked of fast food I realized as I made my way up the rickety front porch. I didn't have a key or anything and was forced to knock.

I waited on the cold porch for a long time and I couldn't help but notice the laundry basket from yesterday was sitting empty by the door. Finally Miss Rose came to the door but instead of opening it she peered through a metal slot.

"You smell absolutely filthy you are not coming in here with those greasy clothes on! Put them in the basket first!"

I couldn't believe it. It was freezing out here and she wanted me to undress! What if someone drove by?! "But Miss Rose can't I at least come inside first?" after a minute of silence she responded.

"Absolutely not! Put those disgusting clothes in the basket or sleep on the front porch for all I care!" I really didn't want to do it but it was late and I was so tired.

The street was pitch black and I could hear an owl hooting nearby. I gritted my teeth and once again did as I was told stripping down to my underwear tossing my work clothes in the basket setting my shoes beside it.

Now I was cold, shivering in only my tighty whiteys as I knocked again. For the next few minutes I only got silence as I hugged my self trying to keep warm.

After a while I started to wonder if maybe she meant for me to take EVERYTHING off somehow. She hadn't really specified and for some reason she wasn't answering. There was no way I was doing THAT I thought to myself.

I considered for a moment putting my clothes back on and going somewhere... But there was no where to go. I was out in the middle of nowhere without any way or anyone to call or find my way out of here. The cold was really getting to me and the silence treatment was giving me my answer I thought.

I paced back and forth trying to work up the nerve while at the same time trying to stay warm. I kept hooking my thumbs into my briefs before chickening out and knocking again. "No she couldn't possibly expect me to..She must be a pervert or something." I thought to myself. My resolve was really starting to falter whenever i thought about my other options not to mention the cold. Fine I thought finally giving up about to break mentally.

I hooked my thumbs inside my waistband once again and a split second before I was going to pull them down the door popped open and she told me to hurry up and get inside. I couldn't believe what I almost did was all I could think as I rushed inside in only my underwear leaving my work clothes outside.

Her eyes seemed to look me up and down her expression was quite stern as she pointed towards the bathroom not saying a word. I didn't feel like I was in any position to argue and I was a bit irritated it was best for me to go along for now I thought. The shower was quite the relief although I could tell it wasn't as warm even as it was that morning. Of course Miss Rose dropped off only a towel and a pair of fresh underwear leaving me with nothing else......
ValerianXIII
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Re: Landlady from Hell

Post by ValerianXIII »

Over the next week I slowly began to get used to the same treatment. The moment I entered her house I always had to strip down to my underwear first. I tried several times to ask about my clothes or things but the subject was always changed or I was shushed up right away without an answer. When I wasn't at worked I spent my off time cleaning and doing various chores around Miss Roses house. The exhaustion was starting to catch up with me and my work really suffered.

Going into the second week I fell asleep for a moment on accident and my boss caught me on camera. I was devastated when my boss fired me at the end of my shift. I really didn't know what I was going to do as I got off that bus and walked to Miss Roses front door. Now I had no job no car and soon no place to live. After I ceremoniously stripped down to my briefs and Miss Rose let me inside. I couldn't help but look at the floor not knowing how I would explain what happened to Miss Rose. Even after all I went through I still felt guilty as I tried to get the words out. My rent was paid up for the month and I had another small check on the way even with all that Miss Rose seemed more than pissed when I finally worked up the nerve to drop the bad news.

"Unbelievable" Was all she said to me and pointed towards the bathroom like usual. I made my way to shower this time holding my head down. The hot water was completely gone and I suffered through the icy cold shower the best I could. My balls and penis were shriveled up to almost nothing at this point as I endured the icy chill. Instead of a fresh pair of underwear I was only given a small towel to dry myself off and then I struggled to wear around my waist as I met miss Rose once again in the living room. While she was seated i tried my best to keep the small towel around me as she laid out the new rules.

I really thought I was going to get kicked out at that point and in a way was quite relieved. Instead of finding a new job like I thought she might suggest she told me I would be working more around the house. I was a bit surprised by that wondering if she really needed my money at all and what more I could possibly do around the house. Well she had a ton of more things for me and all kinds of new rules. it was impossible for me to follow as she went on and on reading about my new status and my loss of whatever privilege's I supposedly had. The whole time I struggled to hold the small towel around my waist wondering when I would get something to wear.

Finally the woman tossed me what I thought were clothes at first. I nearly lost my small towel trying to catch them. I was disappointed to find out it wasn't two items but one. A plain white t-shirt was all she was giving me and my mouth was open in disbelief as I realized she had forgotten underwear.

"My..my underwear. I need some underwear." I said in a whiny voice that was unintentional. "Oh hush! Your little undies are in the wash. That t-shirt will cover you plenty. Now hurry up and put it on before I have you working in your birthday suit!"
Qwerto1232
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Re: Landlady from Hell

Post by Qwerto1232 »

Great story, i just created accaunt here so i can coment on this. love it, especiali when he ende just in tshirt. For long time i was waiting for story with this element. younger man wearing just the t-shirt without acces to another clothes perfect. that feeling of dread and vulnerableity. I need more story with this element so many possibilities. Hope he will wear just that shirt or nothing. Can't wait for next chapter.
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