The Landlady

Story Info
Sometimes the unconventional is just what you need.
8.2k words
4.61
29.5k
35

Part 1 of the 4 part series

Updated 06/11/2023
Created 01/28/2022
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

Chapter 1.

It was not only frustrating but a little humiliating in a way. Flat-sharing had worked well for me for years, but at 32 I was more then ready to be independent. I wanted the freedom to do what I wanted, when I wanted, walk around in my underwear or less if i wanted - basically become an independent guy. I'd been looking around for a place to buy for ages, but the market in the city was out of control. Prices had shot up even more in the last year or two, and after several experiences of finding a place I liked and being hopelessly outbid, I began to worry I'd missed my window permanently.

To make things worse, the house I'd been sharing with 2 friends from work was being sold.

It was owned by Dan's parents, and although technically we had rights as renters, I'd been paying friends rates since I moved in. It didn't feel right to make things complicated, so I'd agreed to move out in the Autumn. At the time that had seemed a long way off, but by the end of summer I was faced with the cold realisation I could end up homeless.

It was in that mindset I met with my friend Samantha for a spontaneous Friday drink. We'd hit it off at a party a few years earlier, but weren't especially close. She was a little older than me, only a little shorter than my 194 cms, glamorous and always immaculately dressed. Most of all, she had her life so under control and was so naturally confident, she always made me feel like the world was a saner and safer place than I usually felt it to be. The relationship had settled into a pattern of a flurry of drinks and the odd dinner at her place, and then nothing for months. I'd always assumed she or her family were pretty wealthy, because the huge apartment she lived in with her brother was in the most expensive area of the city.

After some catching up she asked about my flatmates. She'd never met them, but that was just the kind of person she was. Before I knew it, I'd laid out the whole sorry tale. Telling it must have made me show all the anxiety about it I'd been pushing away for months, because by the end of it, I was flustered and even a little teary. Sam came around the table and put her arm around me, which was as surprising as it was welcome. I couldn't remember us ever touching before except for the briefest of cheek kissing, and it struck me anew what an impressive woman she was. And true to character she wouldn't hear of me going home to eat alone in what I knew would be an empty flat. As she paid up, she told me to order an Uber to her place so she could cook and as she put it, "spoil my boy".

When we arrived, the first thing I noticed was the door to Tony's room wide open. It was shockingly empty, although as I recall there hadn't been that much in there to begin with.

I'd always found it a little strange that his door seemed to be permanently propped open, showing a room so tastefully but sparingly decorated it could have been in a seminary. And if I'm honest, I was always a little tittilated that he never had anything covering his windows either.

"Did Tony move out?" I asked, realising as I said it how stupid it was.

"That's a sad story," she said, with a wry smile.

"Why? What happened?"

"He met someone, and now he's living with her. I mean I'm happy for him, but..."

"You'll miss your brother being around?" She gave me an odd little look as I said it.

"Yes. Yes. To be honest I didn't think it would ever happen though."

That seemed an odd thing to day, because Tony was an extremely handsome guy. Anytime he'd been there on previous visits, I'd always have to be on my best behaviour to avoid staring at him too much. Something he didn't seem to be aware of, because he didn't make it easy for me. His usual house attire was gym gear. Thin running type shorts, deeply cut sleeveless T's that let his pecs and large brown nipples peek regularly into view.

And on one memorable occasion randomly stripping his shirt off while we were having drinks, torturing me with his perfect torso, trying to stop my eyes flicking down to his belly trail and the waistband of his underwear as he stood talking to me in the kitchen. Damn.

"Why ever not? He's a gorgeous guy, well spoken, good job, loaded. Fuck, I'd marry him to be able live here." It was only half a joke.

"What do you mean?" she asked, raising an eyebrow. I felt myself blushing. Maybe that had crossed a line since we probably didn't know each other well enough for me to be making these kinds of assumptions.

"Loaded? Whatever are you suggesting Andre?" she asked sternly, staring at me for a few moments.

"I... I always just thought, seeing where you live..."

She let me swim for a moment before laughing at how easily she'd embarrassed me.

"Trust me, Tony isn't loaded, financially or any other way. This is my place, not his. As you can see," she said, nodding to the empty room. She sighed.

"Come with me to the kitchen, I suppose I can spill now he's gone."

She soon set me to work, chopping vegetables and pouring us drinks. Once the food was in the oven, she took some snacks and we settled into the huge sofa in the equally huge living room.

"Tony isn't my brother," she said flatly. I didn't quite know how to process that.

"Oh, sorry...I, er." Hadn't she told me he was the first time I met him?

"I used to call him my little brother. But it wasn't literal, at least not in the way you thought it was. We had... an arrangement."

She could see the questions written on my face I suppose, because for the first time she began to tell me her background. She was an only child, and older than I thought - nearer 50 than my own age. Her parents had both died when she was in her twenties - tragic but leaving her independently wealthy. She'd had many who pursued her, but had always mistrusted their motives. Given her looks and wealth I could understand why that might be. And then she asked me something unexpected.

"Do you know what solosexual means?"

"Someone who enjoys self play more than sex with others."

She looked as surprised by my immediate answer as I had been by the question.

"How on earth do you know that?"

I felt myself blushing again.

"I've dated some really great guys, but somehow when it comes to the sex part, it gets awkward and.."

"And?" There was the eyebrow again.

"..and I realised I don't really need physical contact that way when I can do it better myself." I finished, lamely. She sat there for a moment, her eyes oddly intense on mine.

"Maybe that's why I've always enjoyed your company Andre. Not just because I know you're not interested in me as a woman but as a person. Maybe I sensed we have something else in common too. I enjoy men's company, and I sure enjoy being around the ones who are nice to look at too. But I don't need all the psychodrama and the little games that go on when it's starting to become more than that. I'm used to my independence, and most men don't seem to know how to handle being with someone who has more money than they do and is used to calling the shots."

Sam had always been someone who did that. Her general demeanour was always one of a person used to telling others what she wanted and how she wanted it. I guess I was the kind of guy who was happy to let her decide where we'd have drinks, or be summoned to her place at the last minute.

She was sitting nursing her drink, still giving me that look. It made me oddly uncomfortable so I seized on the subject I hoped would break the silence.

"So what did you mean about Tony?" She stared at me blankly.

"You said he wasn't literally your little brother. Is there another way?"

She gave a short sharp laugh, snorting very un-Sam-like into her drink.

"Oh Andre." The small faded from her lips and she began to tell me how they'd met

3 years earlier in some kind of online chat group she was in. They'd started private messaging outside the group. Finally, they'd met up. She realised she'd enjoy someone around the apartment and he needed somewhere temporary to stay.

"It was fun for a while. Easy, the way things should be between friends, right? But then things shifted. I think it was his attitude I noticed first. He'd was challenging me about the way I do things around the house. When I'd have friends over. And I noticed he was spending an odd amount of time walking around in a towel. That room's bathroom is right across the hall, yet he couldn't seem to avoid coming to talk to me like that, or getting himself a beer before or after his many showers. That progressed to him parading around in his underwear half the time."

"Not when I was here dammit!" I burst out.

"Well you actually got closer than you think there Andre." She laughed again, more quietly this time. Unwilling to interrupt her, I let that rather strange remark go.

"It was obviously deliberate. And I suppose not surprising considering how I met him. With his lizard brain he thought he could get me interested in him with his buff body. Which was impressive I know.

"Sorry - how you met him?"

"OK Andre, if I tell you this it's in absolute confidence," she said. the stern look apparently real this time. Of course I swore to keep her secret.

"Pretty much by accident I found this small chat group. A lot of them are pretty random but this one seemed to have some actual real people in it. I got more and more interested and I stayed. It was a BDSM group, specifically for submissive men. I was one of the very few women.

I'd never interacted directly with Tony but I'd seen some of what he posted so I knew pretty much what he was into. So it wasn't entirely a surprise when one night he came waltzing out in his little briefs with what was obviously an erection in them, standing right in front of me as I sat right here. That was a line he shouldn't have crossed, so he didn't get the reaction he was hoping for.

My head was spinning at this. Sam into BDSM? Tony running around in his undies with a hard on, right here was I was sitting? I had to ask.

"So what did you say to him?"

"I took my time looking him up and down. Let my eyes settle on his little undies, then looked him in the eye and said,

" 'Thanks for reminding me to take the shrimp out of the freezer.' And instead of being cocky as he'd been recently, he sort of shrunk before my eyes. Yes, also literally."

"It was something my online persona might have said. I felt a little guilty about doing it face to face though, but I can't help deflating male egos when they're misdirected at me. It reminded me he was only a boy of 25, trying to find his way in life and not really knowing how to interact with women. But I made myself stay stern, because I knew if I didn't break whatever was driving this behaviour, I'd have to ask him to leave. I didn't want that either. I made him stay standing there until he explained himself. It turned out to be just as naive and obvious as I thought. It turned him on to be as he put it 'almost naked' around me and he'd hoped it would mean we could.. you know. Well obviously I soon put that little dream to bed for him. But as I watched him sag even more, I have to admit I was enjoying his discomfort. Online it had been mostly text, so I was fascinated to see the effects of my words playing across his face in real time. If I'm honest it was even turning me on. More than a little."

She paused for a moment to crack an ice cube between her teeth as she finished her drink.

"I asked him 'why just almost naked? Don't you mean you really wanted to be naked-naked?' The poor boy could barely speak but I made him repeat himself until it was clearly audible. Of course that's what he'd really hoped, because I'd be so impressed by his buff body I'd want to have sex with him too. I had him stand up straight, asked him to do a few poses for me showing off his muscles, which admittedly he did work hard for. I saw cocky Tony coming back. and sure enough when he turned back to face me, the bulge in his briefs was back too.

"I let him stand there for a moment, then looked him in the eye and said,

'So get naked Tony.' He gawped at me, a mix of confusion and excitement in his eyes.

'Get naked Tony. Take them off' This time he didn't hesitate and like a good boy shucked his briefs off and stood up triumphantly. To be fair, his hard on was about as hard as it's possible for a dick to be. Unfortunately.."

She put down her glass and picked up one of the discarded cocktail sticks lying on the table in front of us.

"You wanted to know why I called him little brother? Cocktail stick was one of the nicknames I used when he needed a reminder of his obligations."

So hot Tony had a cocktail stick? I have to admit I was a little disappointed my wank fantasies about him had just gotten blown up. But at the same time, hearing how Sam had so easily taken control of him was strangely arousing and just made me admire her more.

"So what happened?"

"Not much. I let him pose for me for a bit and then told him I was going to bed. Another disappointment for him I'm sure."

" But you let him live here all that time afterwards, so you must have had a reason I guess."

"There's always a reason Andre," she said, wistfully playing with the cocktail stick still in her hands.

"I let him stew for a few days, and by the weekend I'd decided what I wanted. He came home from work in the afternoon and I sat him down here so I could lay it out for him. Seeing him in his work clothes only made me think I was making the right call. He looked more like a model than a building contractor. I may not need men for sex, but I'm not made of stone. And Tony was a greek statue.

"I told him he could stay as long as he needed, rent free, because the rent had never been the point. I'd even let him be naked around the apartment, but on my rules and my terms.

He looked pretty thrilled, but I probably took advantage of him by making him agree before I told him what they were. Not that he had much negotiating power anyway."

This was a side of Sam I never knew existed and I guess I was sitting on the edge of my seat, because she smirked at me and asked me if I wanted to know what the rules were.

"Yes please" I nodded.

"Fairly straightforward. I told him he was pretty but I was never going to have sex with him. He'd be getting naked often. Not when he wanted to, but when I told him to. He was forbidden to come in my room, ever. He could expect little privacy of his own because it was my place and I go where I like. And generally he'd be expected to do what I told him to."

"And he just said yes to all of that?"

"Pretty much. Since our talk earlier in the week, he'd done his towel walk a few times. And remember, Tony was basically a submissive. I think he figured he'd take what he could get."

I could hardly believe what I was hearing and it was making me increasingly worked up, even if I couldn't quite work out why. Sam smirked at me again.

"He was looking way too comfortable sitting right where you are now, and I wasn't sure he really understood I meant business. So I told him to stand up in front of me.

'Get naked Tony'.

He started doing his half assed version of a stripper, but stopped when he saw me laughing.

'Am I not doing it right?' he asked, sounding like a little boy.

'When I tell you to get naked, just get to it. If I want a show, I'll tell you. Just take your clothes off.'

Like a good boy he pulled his work gear off quickly and stood up naked in front of me.

Time for the first lesson.

'I'm not your mommy. Pick up your dirty work clothes and put them in the closet in the hall.

Those stinky undies too. I've put a basket in there for you.'

'He did as he was told, and the fact his little penis was standing stiff across his belly when he walked back told me I'd hit on just the right approach. Maybe this would really work out for both of us after all." I took a moment to picture Tony, completely naked and with his small but rock hard dick pointing skywards. Damn.

"Wow Sam. I never had any idea, not for a second. I always thought he just looked up to his big sister. He was pretty much in awe of you. But this... is pretty unexpected. I get what Tony got from this, but what about you?"

She looked at me for a moment.

"You seem to be enjoying hearing about it, so why don't you tell me? What did he get from it?"

"Well, I guess he was basically one of those guys who know they look good and love showing it off to get a reaction."

"He was an exhibitionist yeah, at least for women," she said flatly.

"And even if he didn't get you, he got that and free rent too. And a beautiful women to tell him what to do. "

She crushed another ice cube in her mouth. "I had an idea you'd get him, but what about me?"

"Hmm well...I'm assuming you liked having a toy to play with. And who wouldn't, even if he was a..."

"Cocktail stick," she said, standing up. "On your feet Andre." She lead me by the hand to the kitchen and told me where to find plates and cutlery as she busied herself with the food.

We chatted about other trivia as we ate, but I was burning to know more about what had happened to Tony. As I helped her clear, I knocked over yet another small container with little wooden sticks. Sam gave me the eyebrow.

"Clumsy boy. I suppose I can get rid of those now. It's not like they have much purpose anymore."

"Because you only used them to tease him?" I asked. She rolled her eyes.

"OK, you really want to hear the whole damn story don't you? Fine. Just don't blame me if I shock you."

Chapter 2.

Sam poured us more wine and dragged me back to the sofa. But instead of letting me sit beside her, she directed me to an equally enormous hocker opposite her seat.

"I want to keep an eye on you while I'm telling you this." She sat back, took a sip of her wine and let out a deep breath.

"So where did we get up to?"

"Get naked Tony," I said, feeling how strangely erotic those words felt in my mouth, and seeing that image of him again in my head.

"That's right. And he didn't have to be told twice. Not that time anyway. I kept him that way the rest of the night. Nothing much happened, but I have to admit I was enjoying seeing him walking around bare assed more than I expected. He may not have been a big boy up front, but the rest of him was pretty outstanding. And when I went to bed I gave the old Rabbit a work out I can tell you." She looked at me but before she could ask, I kept my voice as even as I could to tell her I knew what that was.

"When he came home from work the following day, I was waiting at the door. I wanted to see if he'd gotten how this was going to work. 'Take your clothes off Tony'. He started to complain about the day he'd had and how much he needed to shower, taking a step toward his room. I realised he needed to have it spelled out to him how this was really going to work.

I grabbed his wrist and dragged him to where you're sitting now. But when he went to sit down, I stopped him. Having him stand there in front of me like a naughty child seemed exactly what was required.

'What did we talk about last night?'

'You told me I could live here for free, and I can be naked more often at home, right? I loved hanging out with you by the way.' He actually had a grin on his face.

'You've got it exactly backwards,' I told him. 'What I said was you'll be taking your clothes off when I tell you to. And giving up your privacy. And doing what you're told. That's why I will let you live here rent free.'

'But why,' he asked, "when you don't want me to to pleasure you in other ways? He was genuinely struggling to make the distinction.

'Because you need discipline. Because this is my place and my rules. Because I like having you here, but without any misunderstandings about what this is and is not. And because I think we can both get something from it. You just said you enjoyed being naked with me, yes?'