Owned by the Landlady - part 5 (Patreon)

Owned by the Landlady - 5

Josh - making deals

I headed to bed after the day's events, just the sight of the tan lines on my body as I undressed caused me to blush and I wondered how long they would be visible for.

It was as I was twisting to see the outline of the word ‘sissy’ on my back that my bedroom door crept slowly open.

“Looking good, Josh.” Paige said quietly as she tip-toed into my room.

I quickly pulled my shorts up to hide as much of the tan lines as I could. “What are you doing here? You being here got me in enough trouble the last time.”

“Well you weren't complaining so much while cumming in your pants.” She replied, walking in and sitting down on my bed. “Maybe I'm here cause you owe me one.”

I sat down next to her and covered my crotch area with a corner of the blanket to stop her from noticing the chastity cage. “Owe you one?”

“Yeah, well I got you off last time, I think you should return the favor.” Paige said, smiling mischievously.

“No way. What happened last time got me in enough trouble with your aunt.”

“Oooh so is that why she put you in that maid outfit and sent me the picture? She asked, giggling.

I blushed. “Something like that.”

“Awww,” Paige cooed, sliding closer to me on the bed, “so no more secret time playing time?” She asked, her head moving close to mine, close enough to feel her breath, smell whatever body wash she had used in the shower.

My cock twitched inside its prison. “N-no. No more.”

“What if we just kept it PG? Just a little kiss goodnight.” I turned my head to see Paige's lips advancing towards mine. She kissed me, light at first, but when I didn't back away immediately she got a little more into it.

I should have stopped her then, but the way she looked in her small pajama top and shorts set, no bra underneath, plus how horny I was, it was impossible for me to resist kissing her back. I felt her hand moved up my thigh, sliding beneath the cover.

“Wait, Paige we can't…” I said, pulling back from the kiss.

“Shhh, it's okay, Josh, we're just two people having fun. I promise Diane will never find out.” Paige leaned in and kissed my neck as I tried to gather up the will to tell her to leave. I was too horny, too weak.

I had never hated the chastity cage more than I did at that moment. “It's not that it's….” I tried to explain that I couldn't have any ‘fun’ at all right now, but it was too late. I felt Paige’s hand move to my crotch and squeeze slightly, no doubt feeling the hard shell of the chastity cage.

“Wait…” She pulled her head away from mine, “Is that what I think it is?” Did she know what it was?

“Well….maybe. What do you think it is?” I asked.

“Are you wearing a chastity cage?”

Shit. She knew. “Yeah. I am.” I replied.

“Hahahah no way! Does Aunt Di know about this?” She asked.

“Well, yeah. It was her idea. And it’s all your fault!” I added.

“My fault?”

“Yeah, your fault. After what happened last time Diane doesn’t trust me with her precious niece, so she made me agree to wear this while you’re here.” I explained.

“Hahaha wow! She really outdid herself this time. I don’t know what she has on you that she was able to get you in a maids dress AND a chastity cage. You must really have it bad. Hahaha.” Paige laughed.

“What do you mean by that?”

“Oh, please. There’s only certain types of guys who would find themself in the position you’re in. And my aunt seems to have a way of attracting them. Man you must be getting pretty tight down there after that.”

“A little.” I admitted.

“Haha, awww, you poor trapped little guy. So you’re keeping the cage on while I’m staying here?”

“Yep, pretty much.”

“Maybe I should visit more often.” Paige said with a smirk.

“I’d rather you didn’t.” I replied, a little sarcastically. Paige’s presence was definitely a turn on for me.

“Aww don’t be like that, sissy.”

“I am NOT a sissy.”

“That’s not what your tan line says, hahaha.”

“Fuck you. This was your aunt’s stupid prank, that’s all.” I snapped.

“Wow. That’s not very nice of you. I’ll have to get you back for that, Josh.” Said Paige, a playful bit of annoyance in her voice.

“Wait….Don’t do anything, please, this is bad enough.” I said, pleading.

“Hahaha, well I’ll have to see what mood I’m in tomorrow. But seeing as I won’t get to play with your little dick today, I may as well go to bed. Night, chastity boy, haha.” Paige left, leaving me alone and twitching in the cage, wishing I could relieve the pressure before bed.

—

Sunday morning, the morning after a restless night due to Paige’s visit, I was downstairs eating a little breakfast after spending the first hour after waking up enjoying my new games console. Paige joined me at the breakfast bar in Diane’s kitchen, pouring herself a drink and sitting down opposite me.

“How’s the cage feeling this morning?” She asked, staring at me over her coffee cup.

“Fine.” I answered, not wanting to get sucked into her teasing but just the mention of my caged cock had caused a stir.

“Mhmm, sure it is. So what's the deal, as soon as I leave aunt D gives you back the key and you run straight to your room to jerk your little dick, is that it?” She asked.

“Something like that.” I replied, trying not to rise to her bait.

“I'm curious,” She said, watching me intently, “will you be thinking of me when you do it?”

“Not a chance.” I said.

“Pfft, yeah, right. I'll bet you're still dreaming about the time I touched your little cock.” Paige started mimicking an exaggerated ‘sex voice’ “Oooh, Paige! Paige, please stroke my little cock for me. Please make me jizz all over my pants like a horny teenager.”

“I didn't act anything like that and you know it.”

“Maybe not on the outside. But it was pretty easy to tell how much you loved it.”

“Isn't it time for you to go home?” I asked.

“Wow, that's not very nice. But I guess you would be waiting for me to leave, wouldn't you. You want me to leave my bikini here so you can top up that tan? Hahaha.”

“Fuck you.” I hit back, annoyed but still feeling the arousal at her teasing.

“Wow, again with the insults, you're really not helping yourself you know. If I didn't know any better I'd say you wanted me to make things worse for you.”

I wanted to object to her statement, but Diane chose that moment to interrupt us.

“Good morning. What are you two talking about?” She said, breezing into the kitchen.

Paige answered first. “Oooh, nothing much, I was just telling Josh that I might stay here another night.” Paige was looking right at me with an evil grin as she spoke.

“Stay as long as you like, dear. You know you're always welcome.” Diane replied.

I stared at Paige, knowing exactly what she was doing. One more day here meant longer in the chastity cage for me and more time for her to torment me about it.

“Thanks Aunt D,” Paige shot me a glance that Diane hadn't noticed. “I was actually thinking of maybe staying for the whole week, but I wouldn't want to impose.”

The whole week! Surely Paige had better things to do.

“You're welcome here any time for as long as you want. No imposition at all.” Said Diane. “Besides, I'm sure Josh appreciates having some company his own age. Right, Josh?”

“Uhhh….yeah. I guess.” I replied, noticing the look of pure glee on Paige’s face.

“Well, I'll have to see if I can clear my schedule for a week.” Paige replied. I hoped she couldn't!

—

Later that day, I was in my room, typing out an email to work, informing that I was temporarily unreachable by phone, when Paige decided to interrupt me.

“Watcha doin, Sissy?” She said, bouncing into my room and sitting on my bed.

“Emailing work about my broken phone…and don't call me sissy!” I added.

“Well it's hard not to when it's literally burned into your back.”

“Whatever, did you need something or did you realize it's been a whole half an hour since you tortured me in some way?” I asked, sarcastically.

“Well I actually came here to see if you were looking forward to the whole week of me staying here.” She said in an overly innocent tone.

“You're not serious about that, are you?” I asked.

“Of course, why wouldn't I want to spend a whole week in a house with a pool and a rich aunt who would do anything for me?”

“Come on, Paige, don't you have a job to go to?”

“Meh, they can manage without me.” She replied with a shrug. “Just think, a whole week locked in your little cage with no release and me here to keep you company. Won't that be tons of fun?”

“For you maybe.” I mumbled.

“Orrrr, we could play a little game.”

“What kind of game?” I asked, hesitant to know what she had in mind.

“Easy,” Paige reached a hand into her pocket and pulled out a small bundle of yellow fabric, “all you have to do is wear these.” She tossed the fabric into my lap.

“This is…”

“A pair of my underwear.” She said, simply.

“Why the hell would I wear your underwear?” I asked, beginning to wonder if all the women in this family were crazy kinky.

“Because I said so, or because you really don't want me to stay the whole week. It's simple really, the aim of the game is to wear my panties without aunt Di noticing. I'm sure if she caught you she would have something to say about it.”

“Okay, but if she catches me?”

“Then I'll deny all knowledge of this conversation ever happening. And let's face it, she's going to believe her beloved niece over her perverted lodger any day.” There was that innocent voice again. “Just don't let her catch you with my panties on and you win. Or don't play and I'll stay here the whoooole week. What's it gonna be?”

I had a feeling Diane wouldn't let me off the hook with my maid duties for a whole week just because Paige was here, and I knew damn well I didn't want Paige around to see me working in my outfit. Plus I really wanted out of the chastity as soon as possible, so I decided to say, “Okay, but you have to leave first thing tomorrow morning. No dawdling around to torment me more before you go.”

“Okay, deal. Now put on your panties.” Paige said, shaking my hand in agreement.

“Can I get a little privacy?” I asked.

“Nah, I'm not going anywhere till I know you're wearing my underwear. Besides, I know there's not much to see down there anyway.” Paige replied, before adding. “But if it makes you feel better I won't peek while you put on your panties.”

“Fine, whatever.” I replied, deciding just to get it over with. I turned my back to Paige and swapped out my underwear for the small, yellow panties she had given me with a distinctive butterfly pattern stitched into the seat, feeling how a large portion of the rear was designed to sit between my cheeks. I pulled my shorts back up, with my back to Paige, and told her I was done.

“Great job, great ass too by the way.” Paige said, smirking. “Now remember, if Diane catches you in those I'll deny all knowledge and make it much worse for you, your job is to make sure she doesn't see them. Oh, and that means you can't hide in your room all day either. And regardless of whether you win or lose the game, I'll be gone first thing in the morning so you can finally free that little baby dick of yours.”

“Hey!” I snapped, blushing.

“Hahahaha, see ya downstairs.” Paige skipped out of the room with a laugh, leaving me to adjust to the feeling of the panties cupping my caged package.

Paige said I couldn't hide in my room all day, but I chose to stay there for as long as I could get away with it. Before I headed downstairs, I checked myself over in the mirror to make sure the underwear couldn't be seen. “Can't believe I'm standing here checking myself for damn pantylines.” I muttered as I headed out of my room.

—

Something else

“Are you sure you're okay, Josh?” Diane asked me as we sat in the back yard, having a drink in the afternoon sun. Paige was inside, talking on the phone to a friend. “You seem a little….fidgety.”

“No, I'm fine. Really.” I replied, making a mental note to do a better job of ignoring the panties.

“Okay, great.” Diane said, turning around on her chair to face me. “So, been meaning to ask you all day, do you know what you're gonna do about your phone situation?”

I thought back to the reply to the email from earlier. ‘Please let us know when you are contactable again by phone.’ I was essentially on call while I was here, and being unreachable at a moment's notice could be disastrous. I would hate to lose the job to someone because I missed an email. “Well I know I need a new phone, but with what little money I have I'm kind of limited….kind of very limited.”

“That's what I thought, so, how about another ‘contract negotiation’?” Diane asked with that smile that suggested she was up to something.

I sighed, knowing something like this would be coming. “Okay, let's hear it. What ridiculous and humiliating thing do you want from me this time?”

“Haha, you know me so well. But fine, straight to the point….I want your hair. Specifically everything from the neck down. Your work outfit would look so much better without all that manly hair ruining the look.”

“You really want me to shave my hair? But what if someone asks about it?” I said.

“Tell em whatever you like,” Diane shrugged, “I have a pool, tell them you're working on your swimming.”

I thought about it for a sec and figured that excuse might work. Swimmers shaved their bodies all the time….and I really needed that phone.

“I’ll even sweeten the deal a little more,” Diane added, clearly knowing that she had me on the hook, “you can pick whatever phone you like. Latest model, whichever brand, however much memory. The one that broke in the pool was pretty old by the looks of it, it’s about time for an upgrade, don’t ya think?”

She had a point. “Fine. Deal.” I said, shaking Diane’s hand and making the second deal of the day with a woman from this family.

“Great! Tomorrow before your shift starts, I’ll help you get rid of all that hair.” And so that was that, the deal was done and once again Diane was going to get her weird, kinky way. But what choice did I have? I needed the phone.

—

“Hey there, sissy. How’s my panties treating you?” Paige asked, cornering me in the kitchen when Diane was out of ear shot.

“They’re fine, thanks for asking.” I replied, trying not to rise to her teasing, despite the tightness from the chastity cage.

“Uh-huh, sure they are. Let me see.” Paige said, standing back and staring at my crotch.

“What?”

“I need to make sure you’re still holding up your end. Quick, before aunt Di comes back in. Unless you want her to see you in your pretty panties.” Paige replied, giggling a little

“Fine, here.” I pulled the front of my shorts down a little, showing Paige the lacy front of the yellow underwear.

“Cute. I like how they show the imprint of your little cage so clearly. Bet you're desperate in there by now, huh?” Said Paige.

“Shut up.” I pulled my shorts back into place just as Diane entered the kitchen.

“Hey, can one of you pour me a drink? Worked up a sweat cleaning up the living room, I could really do with hiring myself a maid.” Diane said, shooting me a teasing look.

Paige made her aunt a drink, but as she passed me near the counter, she brushed up against my lower back, right at the waistband of the shorts. “Whoops, sorry Josh.”

I squirmed a little as I felt Paige's hand lower my waistband slightly. I looked towards Diane, hoping she hadn’t seen anything.

“Josh? Everything okay?” Diane asked, clearly noticing my sudden discomfort.

“Fine.” I replied quickly as I heard Paige giggle behind me.

—

I was doing so well keeping the panties hidden from Diane all day. She had noticed that something was wrong with me but as far as I could tell, I was winning Paige’s annoying little game. Paige insisted on checking on my panties throughout the day whenever she could get me alone, making sure to make it as awkward as possible for me.

Diane had just asked for our help in carrying a load of laundry upstairs and Paige replied quickly. “Me and Josh will get that.”

We headed into the kitchen and Paige began emptying the dryer into my arms. “I thought you said we would help, how come I’m doing all the carrying?” I asked.

“Because I said so.” She replied, cheerfully as she loaded my outstretched arms up with the clothes. With my arms loaded up with the larger items, Paige began pulling the smaller stuff out of the dryer and piling them on top. “Now come on, pantywaist, let’s go.” I followed Paige out of the kitchen, only for her to stop us for a second and call Diane.

“Hey, aunt Di, where do you want us to put all these clothes?” Paige called into the living room.

Diane appeared in the doorway before answering. “Just take them upstairs and drop them on my bed, I’ll deal with them later.” She replied.

“Sure thing, you heard her, Josh, get moving.” Paige slapped me on my butt as I headed towards the stairs, and that’s when I felt the slight tugging at the back of my shorts. “It wasn’t just a slap, she had deliberately tugged down the back of my pants and exposed my ass to Diane.

With my arms loaded up with the clothes, I couldn’t react quickly enough to hide my pantied ass from view. I froze for a second, feeling the blood rush to my face before I quickly spun around so that my back was to the wall and I was facing Diane and Paige. I knew as soon as I saw their faces that they could see the panties. Paige had a look of pure glee and Diane had a shocked expression on her face.

I stared for a long moment before Paige broke the silence. “Holy shit is Josh wearing panties?!” She said, playing up the false surprise.

But it was Diane’s reaction that shocked me the most, I knew as soon as she spoke that Paige had played me good.

“Josh….why the fuck are you wearing MY underwear?!”

Fuck!

End part 5.