The Landlady

Story Info
Alex can't afford to pay rent, and the landlady has an idea.
9.9k words
4.7
127.2k
274
26
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

So I know I have not been posting much lately. It has been a very busy summer for me. I'm hoping to get back to being more constant with posting on here, now that things are settling down just a little. I wrote this one over a month ago but, it needed a lot of work done, and I just got back to finishing it up. I hope you enjoy. I did leave it open for more adventures...let me know if you want more.

*****

I met Melissa when we were still in high school, and we started dating in our senior year. By the time we both had graduated, we were madly in love. I knew very early on, that this was the girl I wanted to marry; well, I thought she was. Melissa and I would go on to date for the next five years.

After all that time together, we decided we wanted to take the next step and find an apartment together. We were both working good jobs, and figured we could afford the rent without much trouble.

That was made even more possible when a friend of my mother's offered us a place.

My mom and Susan had been friends for years, and growing up, Susan was always around in one way or another. She would often babysit me when my parents had to be somewhere and was sort of like a second mother to me. She owned a duplex and lived in the top floor but, was trying to rent out the bottom floor unit. When she found out that I and Melissa were looking for a place to live, she quickly sent me a message and made the offer.

Melissa and I went to check the place out, and we loved it. We accepted the offer, which was a pretty decent deal, and we were moving in just about a week later.

The first six months in our new apartment, things were absolutely perfect. Well; maybe not perfect but, they were great. Melissa and I were both loving our newfound sense of privacy and freedom, that we could not have when we both lived with our parents. An entire apartment to ourselves meant, that nobody could walk in on us having sex, and we didn't have to listen to people stomping around and yelling all the time. Sure, Susan lived right above us, so we could hear her walking from time to time. Susan's job kept her quite busy though, so she actually wasn't even home all that often.

Having our own place also meant, we could invite our friends over whenever we wanted. Although, my friends typically didn't like to come over, when they knew that Melissa was home.

As much as I loved Melissa, I had to admit...she was a bit clingy sometimes.

She had always been that way. And of course, with being clingy comes being controlling and possessive, too. There were times that I couldn't even talk to a female co-worker, if we ran into each other on the streets, without Melissa getting bitchy about it.

Needless to say, this kind of behavior had led the majority of my friends to want nothing to do with the girl. A few of them had even tried to encourage me to break up with her, before.

I had my own issues with Melissa, trust me.

For the past year and a half, things had gone pretty stale between the two of us, when it came to sex. She just didn't seem interested, anymore. We certainly weren't virgins but, sex had always been a very rare activity between us.

It had to be the right moment when she was in the right mood, and that just didn't happen often enough. If I tried to push it with her, it would often lead to an argument, and that was never worth it. Now that it had nearly stopped all together though, things were getting a lot more frustrating.

Still, I loved her...I wasn't about to end a five-year relationship, because my friends didn't like Melissa, or because we weren't having enough sex.

After that six month line, things started to fall apart, slowly but surely. It started when I lost my job because the company had gone bankrupt and shut down. The boss had known it was coming for a while but, he'd kept it from the employees, like an asshole. Now we were all unemployed, and I was struggling with the idea of finding another job.

That last job had been the only one that I had worked for the past five years. I had no resume to back me up, just five long years of working at a piece of shit company, that let all of its employees down in the end. The economy wasn't doing all that great, so I just worried that it might take a while to get back on my feet again...there were bills and rent to be paid, after all.

Luckily, Susan was pretty understanding.

Like I said, she was my mother's best friend and had known me since I was born. So when I told her that I was out of work, she reassured me that everything would be okay and that she believed I could pull myself together. She excused rent for that month, figuring that I would be back on my feet in no time. I was hopeful that she would turn out to be right.

After about a month though, things weren't looking too good.

I had been putting in application, after application, with only a few interviews and none of those had been successful. I was starting to get a little frustrated, and it was showing. Who could blame me though? Aside from the fact that we needed the money, I had also been working for the last five years...I wasn't use to just sitting around the house all day, with nothing to do.

When it came time to pay October's rent, we didn't have the money. Even with Melissa working, she didn't make enough to pay the full $800 a month; not by herself. So, I was forced to talk to Susan again, and just hope that she would be as understanding as she had been the first time.

Susan didn't look quite as optimistic this time but, she agreed to let another month of rent slide by. I could tell that she was annoyed with me but, she was trying not to say anything. I promised that we would have the money in November, and she accepted.

When November came around though...we didn't have the money.

"What the hell are we going to do!?" Melissa yelled angrily.

We had just come home one night from seeing one of her friends, to find an eviction notice on our apartment door. I have to admit, considering our history, I was a little surprised to see Susan handling this like she would with any other tenant. I figured if it came down to be kicked out, that would be discussed face to face.

"I'm going to talk to her," I said, trying to calm my girlfriend down from her freak out.

"I'll see if we can come up with something to fix this."

"You had better," Melissa said, pointing her finger at me.

"Alex, I don't want to go back to my parents' house...you know what living with them is like, and it is NOT going to happen!"

I did know what her parents were like, and I couldn't blame her for feeling that way. It's not that they were bad people but, they were a strict Catholic family, and growing up had been difficult for Melissa. Her parents were constantly breathing down the back of her neck, even after she had turned eighteen and was legally considered an adult.

They were always forcing her to go to church and didn't even like the idea of her being in a relationship. They allowed her to date me because I was a "nice boy" in their words...if they only knew the kind of sex we had.

No, I understood perfectly, why Melissa did not want to go back there. I wasn't exactly thrilled by the idea of going back to my parents, either.

I had to work this out, somehow.

Up the stairs I went, knocking on Susan's apartment door and waiting anxiously for her to answer. Susan greeted me, wearing a white tank top and a mini skirt. I could see her cleavage and it was a beautiful sight, for my eyes. Susan had always been a very sexy woman, and yes, I had always had a crush on her growing up. Even now, in her late thirties, Susan was fucking gorgeous.

Her breasts were an impressive 34DD. She had long, curly red hair and one hell of a body, with a nice heart shaped ass.

"Hey Alex," Susan said, with a serious expression.

"I take it you're here to discuss the eviction notice?"

"If you're willing to talk, then yes. Susan, please...there's got to be some way that we can work this out."

"Come on inside."

Susan stepped aside, motioning me into the apartment. I brushed past her and into the living room, sitting down on the couch. She sat on the recliner, directly across from me and lit up a cigarette. Taking a long drag, she exhaled and blew the smoke into the air.

"Alex, you have to understand that it hurts me that I even have to do this," she began.

"I've known you since you were a little boy. Your mother has always been my best friend, practically my only friend. But, when I moved you and Melissa into that apartment, I did it because I thought it would teach you both responsibility. You're young adults, with your whole lives ahead of you..."

"It has taught us responsibility," I said quickly.

"Susan, I worked for five whole years of my life. It's not like I was just sitting around, doing nothing. When we moved in down there, I had no idea that this was going to happen."

"I understand," Susan nodded. "Everyone falls on hard times, it's perfectly normal. You still have to get by though, you still have to deal with everyday life."

I sighed, becoming frustrated now. The way she was talking, I was starting to feel there was no way around this; still, I persisted. "Susan, please...can we come up with some kind of a payment plan or something?"

Susan leaned back in the recliner, her cigarette dangling between her lips, as she seemed to be contemplating my suggestion. I was hopeful that she would agree to this, and that we could come up with something, that was affordable. Taking the cigarette from between her lips, Susan smiled suddenly. It was a different smile then I was used to seeing with her...there was something behind it. She was looking at me, like a piece of meat.

"Maybe we could work something out," she said finally.

"But, you would have to have an open mind, for it to work."

An open mind?

"Okay, ...what are you thinking?"

Susan put her cigarette out in the ashtray, leaning forward again and smiling.

"Did your mother ever tell you about my little secret?"

"Uh, no, I don't think so."

"I thought not," Susan nodded. "She's a good friend."

"I don't mean to be rude but, what does that have to do with-"

"I'm getting to it."

Susan stood from her seat and walked out to the kitchen, returning a few moments later, with two bottles of beer. She handed one to me, having already removed the cap and then took a swig of her own. "Alex, there are things about me that you do not know. Things that a lot of people don't know, with your mother being one of the only exceptions to that."

"Okay, things like what?"

I still didn't get what this had to do with anything.

"Like the fact that I was born a boy."

I blinked, unsure if I had heard her correctly. Susan looked dead serious though, and I knew what she had just said. "What?"

"That's right," she nodded. "I am a transsexual."

"You're joking, right?"

That serious expression on her face, remained strong, as she shook her head. How was this possible? I never would have guessed that Susan was anything other than a woman. The closer I looked at her now though, the more it started to make a little sense. Susan had always been a little more built than most women.

The muscular arms, the well-toned legs that made her look like a female wrestler. She was always a bit more masculine than most women, and I never paid it much attention.

Even her voice, which had always been a bit deeper than most...why had I never noticed, any of these signs?

"Why didn't my mother tell me this?"

"She was probably trying to be respectful to me...like I said, not many people know about this, and she's always been the type to watch after me. Women like myself go through a lot of trouble in this world, Alex...that's why I'm a very private person."

"I still don't get it," I said, after a brief pause.

"Why are you telling me this? What does it have to do with rent?"

"Right, to the point...I'm going to make a proposition here but, as I said before, you'll need an open mind for it to work."

"I'm listening..."

"I want you to suck my cock."

Once again, I found myself questioning whether or not I had heard her correctly.

"If you do that for me, then I'll excuse this months rent again."

"Susan, I'm not gay."

"There's nothing gay about it," she laughed, standing up.

"It would be gay if I were a man! Look at this ass, have you ever seen a man with an ass like this? Or these tits!"

She grabbed her breasts, giving them a shake for me and I couldn't help but laugh. Still, I just didn't think that this was the right kind of offer for me...I couldn't suck anyone's dick. It was morally wrong for me, plus, I didn't even know HOW to suck dick. Susan could tell that I was still very reluctant. Maybe she had been hopeful, that the beer she gave me would help calm my nerves and make me more willing to comply; liquid courage wasn't really my thing, though.

"How about this," Susan started again.

"Take the night to think about it. Come to see me in the morning, when you've made your choice. But, keep in mind that if you decide NOT to go through with it, then the eviction still stands...you and Melissa will have ten days to find a new apartment."

She had just laid down the law.

I went back down to my apartment, flopping down on the couch and letting out a heavy sigh. What was I going to do? Melissa was at work by now, so I would have to wait until she got home, to tell her about this ridiculous idea of Susan's. I knew that Melissa would not agree, rightfully so, and Obviously, I had no intentions of doing it anyway. The question then, was what else could be done to change this situation; nothing, that I knew of.

When Melissa got home from work that night, I followed her out into the kitchen, as she grabbed a bottle of water from the fridge.

"How did it go with Susan?"

Here we go.

"It went...weird," I said, being honest.

"Weird? What does that mean?"

I sighed, trying to figure out how to even begin to tell her about the conversation we'd had. "Susan wants us out of here in ten days...the eviction notice stands."

I couldn't tell her the whole deal. I just couldn't find the right way to explain it, because it sounded so crazy even to me. Letting her think that Susan was completely unwilling to work with us though, seemed to be the wrong thing to do. I should have fully expected Melissa to flip shit, now.

"She seriously won't work with us on this? God, I always told you she was a fucking bitch! I don't know why your mother considers her such a great friend, that's a load of shit!"

"Relax," I said, trying to calm her down.

"No, I can't relax! We're going to lose this apartment!"

"There's more," I said, deciding that I had to go into details.

"I found out some shit about Susan today, that I never knew..."

Melissa sighed, leaning against the counter and waiting for me to continue explaining. I proceeded to tell her everything that Susan had told me, about her being born a boy, living life as a transsexual woman, how my mother was one of the only people that knew about it. Melissa looked just as stunned as I had been when I first found out about it.

"And you're sure, she's not just fucking with you?"

"I don't see the point in that," I shrugged. "I mean, why would she make something like that up?"

"Well, I don't understand what it has to do with the rent!"

Alright, here we go, I thought.

"Susan did make me one offer...I'm going to turn it down."

"Why the hell would you turn it down!?"

She would understand perfectly, once I had finished explaining the details. "Susan wants me to suck her dick."

This was serious but, the look on Melissa's face was priceless and I had to resist the urge to laugh. She just stood there for a few moments, staring straight at me, completely shocked. I had no idea what was going on inside her head; was she repulsed? Would she flip out, storm upstairs and start an argument with Susan?

Finally, she turned away from me, leaning against the kitchen counter with her back face me.

"That's why I'm turning it down," I started again.

"I mean, I figured you would have a problem with it too, for obvious reasons. I'm not sucking anyone's dick, for any fucking reason."

"Yes, you are."

"W-What?"

Melissa straightened her back, turning back to face me again, with a big lopsided grin on her face. "I said...yes...you are."

She actually WANTED me to suck Susan's dick?

"You're joking, right?"

"I'm serious, Alex. What other choice do we have? I don't have enough money to pay her, you know that. If you don't do this, then we will definitely be going back to where we started."

"Melissa, I'm not gay!"

"Don't look at it like that!"

Ugh, she really was serious about this shit.

"It's only gay if you like it. You're not going in there to suck a dick, for your own pleasure; you're doing it to make her feel good. It's like a job, that nobody likes to work but, it's still got to be done."

"You've got a strange way of looking at this."

"Alex, if you don't do it, and we lose this apartment...I'm going to break up with you."

My heart sunk. I could deal with going back to my parents' place if we lost this apartment. Hell, I could even deal with being on the streets for a little while, if my folks wouldn't take me back. The thought of losing Melissa, though; that I couldn't handle. I couldn't believe that I was about to say it but, I had no other choice. "Fine," I said in a low voice.

"I'll do it."

Melissa breathed a sigh of relief, sitting down at the kitchen table and relaxing a little now. She got what she wanted...I was going to go suck Susan's dick, and we would get to keep the apartment. At least for another month. Hopefully, I would be working again by December, or we would just end up being evicted at a later point.

"I don't even know how to suck cock," I said, worried that I might not do a good enough job.

"It's easy," Melissa perked up.

"Just relax your throat, watch the teeth, and use lots of tongues."

I scoffed, shaking my head. I was getting blowjob advice, from my girlfriend; this was fucking crazy. Might as well get it over with, I thought. I looked up at the clock; it was just past midnight. Susan had a tendency of staying up really late though, so I figured she might not be in bed just yet. I stood from my chair and started towards the door, prepared to do the deed.

"Alex."

I stopped just short of the door, looking back over my shoulder at my girlfriend. Had she changed her mind?

Nope...

"Don't forget to swallow," she said, with a grin.

I knocked at Susan's door, stepping back and waiting for an answer. As I stood there waiting, my mind was starting to race with thoughts of what I was about to do. Sucking dick? I never imagined myself doing that, before. I had never had a single gay thought, in my entire life. I reminded myself what Melissa had said; "it's only gay if you like it."

Then again, would it make it less pleasurable for Susan, if she could tell that I wasn't enjoying myself?

The lock clicked, and the door swung open, to reveal Susan wearing nothing more than a tank top and a pair of panties. She looked a bit surprised to see me.

"Alex...what a surprise...come on in."

Once inside her apartment, I sat on the couch, right where I had been earlier. Susan stood in the middle of the living room, still wearing that big grin; she knew what this was about.

"Have you made your choice already?"

"Yeah," I nodded.

"And?"

I took a deep breath, held it in for a moment and then looked up at her. "I'll do it."

"You're sure you can handle cheating on Melissa?"

"She knows about this...she wants me to do it."

"Really?"

Susan was surprised, which made sense...I was just as surprised. It's not every day, your girlfriend tells you to go suck dick so you can keep a roof over your head. The look of surprise faded quickly though, and Susan smiled again. She stepped towards me, and I stayed seated on the couch. She stopped right in front of me and reached out with one hand, gently stroking my cheek and then running her hand through my hair.