Owned by the Landlady 4 (Patreon)

Owned by the Landlady - Part 4

Josh - Working on my tan

Paige was coming for the weekend, and she had seen that damn photo. The photo Diane had taken after she had iced my cock until it was as small and shrivelled as it could possibly be. I was dreading the thought of talking to Paige again after that, talk about someone seeing me at my worst. Oh, and to top it off, I had been tied to a chair and dressed in a maids outfit in the photo, explain that one!

Diane woke me up that Saturday morning, barging into my room. “Wake up, princess, and put that on.”

“Wha..?” I opened my eyes to see the chastity cage on the bed in front of me. “Huh….Diane…” I sat up straight and rubbed my eyes. “I'm not wearing that….it's the weekend. No work, no outfit, no cage.” I said.

“I know it's the weekend, but Paige is coming over and you've already made it clear that you can't be trusted around her, so put the cage back on.”

“Look, I know you think I can't be trusted, but I told you, Last week was all on Paige, this time it will be different. Besides, you sent her that damn photo of me, it’s not like she’s going to be jumping at the chance to get into bed with me after that.”

“Haha, probably not, now that you mention it. But I’m asking you to put on the cage. If you say no, I may have to find a way to punish you.” Her eyes narrowed and a smile appeared as she spoke the last sentence.

There was that damn suggestive tone again. I had flashbacks to the first time I had deliberately goaded her into punishing me with a spanking, and things had escalated from there. Diane seemed to know just how to play me, this was a trap and she was goading me to walk right into it. “Do your worst. I’m not locking up my cock.” The look in her eyes suggested that may have been a mistake.

“I was hoping you would say that. And I’m going to make sure you regret it.” Diane left my room without saying anything else, leaving me wondering if I had made the right choice or not. Ah well, I don’t have to make it easy for her to punish me.

—

I got dressed and headed downstairs an hour or so later, wondering just what exactly I was walking into. I saw Diane cleaning a jug and glasses. “What’s happening?” I asked, a little nervous.

“Paige will be here soon, and I figured since it’s going to be pretty hot this weekend, we could enjoy the pool and do a little sunbathing. You’re welcome to join us.” Diane said, a little too sweetly.

I gave her a sideways glance. “You’re up to something.”

“Who, me?” She said, clutching a hand to her chest. “I would never.”

“Yeah, right.”

“Oh would you relax, come hang out, we’ll have a girly day by the pool, I’m sure that will suit you just fine after the week you’ve had.”

“Ha-ha, you’re a real comedian. But fine, It’s not like I have anything else to do today.” I said.

“Great, I can lend you a bikini. You prefer a two-piece or an all in one costume?” Said Diane.

“I’ll stick to shorts, thanks.”

I spent the next hour or so helping Diane pull the cover off the pool and catching leaves in the net. The sun was starting to beat down a little and we were both working up a sweat as it got to midday. Paige turned up just as we were finishing and I made my exit, leaving Diane to greet her.

I spent the next half an hour in my room, wondering how I was supposed to face Paige after the photo she had seen. I changed into my swim shorts but found myself panicking about heading downstairs and joining the girls. I looked down at my cock as I pulled up my shorts and wondered if it was actually as small as Diane made out.

“No! She’s just fucking with you dude.” I told myself. “Don’t let her get to you.”

I decided to face the situation head on and head out to the pool. ‘Damn’ I thought to myself as I stepped out the back door to see Diane and Paige, both in small, two piece bathing suits. Paige with her lithe, younger and tighter body and Diane with her curvier, more mature one.

“Oh hey! Look who crawled out of his pit.” Said Diane, lowering her sunglasses a little to see me better.

“Hello again, Josh.” Paige said, grinning. “What, no maid dress today?”

I blushed red at her comment and was trying to think about something to say back when Diane interjected on my behalf. “Paige, don’t tease him like that. I told you that photo was me just playing around with AI image stuff.”

“I know, but it’s fun to see his reaction.” Paige giggled. I couldn’t believe Diane had let me off the hook like that, but would Paige actually buy that the pic was fake? Or maybe she was just going along with it to spare my feelings. Either way, if we didn’t need to talk about it, that was fine by me.

Diane had set up a third sun lounger for me by her pool, right in between the two girls. “Help yourself to some ice water, keep you cool.” She as I lay down and enjoyed the early afternoon sun.

“Hey, Josh,” Diane said, “do me a favor and rub some sun screen on my back will you?”

“Sure, I guess.” I replied, grabbing a bottle of lotion that had been left out. I let out a faint gasp as Diane rolled over onto her front. It turns out the bikini bottoms she was wearing were thong-backed. Diane's whole ass was on display and I found myself staring at it for a long moment.

“Come on, Josh, I don't wanna get burned out here.” Said Diane, shaking her hips a little and causing her wide ass to jiggle temptingly in front of me.

“I think he's just distracted by your ass, Aunt Dee.” Paige added, unhelpfully.

“Ohhhh right, I forgot how much he likes to stare at my behind. You should see him practically drooling whenever I wear my yoga pants.” Said Diane.

“I do not drool.” I said as I uncapped the lotion and squirted a large amount onto Diane’s back. I started rubbing it in, a little aggressively at first in hopes of getting it over with quickly before the stirring I could feel in my cock got worse.

“You can straddle me if it helps get it rubbed in easier.” Diane said as I willed myself not to stare at her ass.

“I'm good, I can reach just fine.”

“Well don't forget to do my butt, I'm sure you'd love that, haha.”

“Seriously? You want me to rub cream into your ass?” I asked.

“Of course, I don't want my cheeks to get burned.” She wiggled her hips a little again, shaking her ass at me.

I dripped a little sunscreen onto each ass cheeks and rubbed it in carefully, trying my best not to let it turn into a full on grope but I was hypnotized by the way the flesh felt under my fingers as I applied the lotion. It was the sound of Paige's giggling that snapped me back to reality.

I looked down to see a prominent tent in my shorts. “Fuck, finish the rest yourself.” I said, quickly lying back down on my lounger, face down this time.

“Josh,” said Diane with a smile, “what's wrong?”

“Hahaha, I think your lodger may have gotten a little excited, that's all.” Paige said, laughing at my reddening face.

“Ohhh, I see. Maybe he should've taken my offer earlier.” Said Diane.

“What offer?”

“Nothing!” I answered quickly before Diane could. “Your Aunt’s just being a pain in the ass.”

“Sounds to me like you have ass on the brain, Josh.” Diane added with a giggle. I couldn't help but think she might have had a point though, the chastity cage would have at least prevented that embarrassing incident.

A short while later, Paige got a phone call from a friend and disappeared into the house for a while. When she returned, she was dressed a little more appropriately, with some shorts over her bikini bottoms and a loose t-shirt.

“Kim just called and we haven't caught up in months.” Said Paige, “I'm heading out to meet her for a drink but I was thinking of inviting her back here for a drink later if that's okay?”

“Fine by me.” Diane replied.

So I was alone with Diane by the pool after Paige left and thought I might be in for a pretty chilled Saturday….Diane had other plans.

As I relaxed on my sun lounger, laid on my stomach with my arms by my sides, I heard Diane crack open a bottle of lotion. “Stay there,” she said from somewhere nearby, “let me rub some of this onto you before you burn.”

“Oh, right…..thanks.” I said, “I usually don't bother with sun cream.”

“Typical man, imagine thinking you're tougher than the actual sun.” Then I felt Diane straddle the backs of my thighs, practically mounting me as I lay on the plastic lounger. I felt a cold drizzle of slippery lotion land on my back as Diane's hands began massaging it in. “There we go, you just relax and let Aunty Diane take care of you.”

I could feel her soft, warm thighs either side of my own as she massaged my back and I was once again thankful that I was laid on my stomach. “May as well get your arms while I'm here.” She said as both her hands ran down my arms which were currently relaxed by my sides as I relaxed into the impromptu massage.

“Hey, what the-” I heard a sudden click at either side of me and tried to jerk up to see what had happened, only to find my arms had been cuffed to the plastic lats on the sun-lounger, trapped by my sides.

“Ha. Gotcha!” Diane said, triumphantly. She spun around so that she was sitting facing my feet, her body weight pinning my legs down.

I knew what was coming even before I felt the ratcheting sounds of the cuffs around my ankles, further trapping me in position on the lounger. “Diane! What are you doing?”

“Punishing you, as promised. You knew this was coming. Be right back.” I was only able to watch her ass bounce out of view as she ran back to the house. It was then that I saw the linen bag she had carried out with her that was obviously concealing the cuffs she had used to fasten me in place.

Diane returned shortly after with a small two-piece bikini that would match her own. “If you're gonna work on your tan, you really need to make sure you pick the right bathing suit.”

“Don't you dare!” I said, wriggling on the bed, but with my arms trapped by my sides and my feet attached to the very bottom of the plastic lounger I was unable to do anything but wriggle side to side.

I felt my shorts get pulled roughly down my legs, all the way to my feet. She couldn't pull them all the way off thanks to the cuffs but that didn't matter, they were stuck bundled up by my feet and offering my ass no protection at all. The bikini bottoms were a tie-at-the-sides style, which made it easier for her to pull them into place underneath me, ‘accidentally’ brushing against my cock as she did. “Whoops, sorry, little guy, hahaha.”

I felt the thong-back of the bottoms get pulled harshly between my ass cheeks before Diane tied them off at the sides. “Beautiful!” She said, punctuating it with a slap to my now exposed cheek. “Just need to top up the carrot oil.”

Wait…..did she say, “Carrot oil?!”

“Why yes, it will really help speed up the tanning process.” I felt more of the slippery substance land on my ass and Diane massaged it in, practically groping and squeezing my ass as she did.

It became clear then what her punishment was, the sun, the bikini, the tanning oil. I was going to have some pretty embarrassing tan lines if I was stuck here for too long. Diane shoved the top of the bikini underneath my chest, manipulating the cups into position before tying it around my back and the back of my neck, completing the look. “Diane, come on, this is too far.” I complained.

“Then you should have done what I said and just put the cage back on your little dick. What was it you said to me? ‘Do your worst’. Well, now you’re getting what you wanted.” Diane said as she finished covering my ass and the backs of my legs in the tanning oil. I could already feel the sun on my back. It was now pretty much mid-day and the sun was almost at its highest.

“There, that should ensure a nice, even tan on your back. Whoops! Missed a spot.” I felt a dollop of cream land on the small of my back, this one feeling thicker than the oil she had already used. She seemed to use one finger to spread the lotion on my back before she stepped away. “Perfect, now we’re just two girls working on our tans.” I turned my head to see her laying back on her own lounger.

“How long am I supposed to stay here exactly?” I asked, testing the cuffs with a little wriggle.

“As long as it takes to make sure you have a nice tan….And more importantly, some nice tan lines.”

“Fuck. You’re the worst landlady ever, you know that?”

“Hahaha, and yet here you are, with me instead of back home with your family. What does that say about you?” She asked with a cocky smile.

“That I’m an idiot.”

“Ha, probably. Or that you love it. Let me know if you get thirsty…” Diane laid back and pulled her shades back into place, settling in to enjoy some sunshine.

After maybe a half an hour, I could feel the heat all over my skin and the sweat running down my sides onto the towel I was lying on. Diane made sure I stayed hydrated by sticking a straw into my mouth whenever she took her own drink. “Mmm, that’s it, suck it, baby.” She said as I swallowed a mouthful of water.

“Fuck off.” I grumbled, grateful for the drink, even though it did come with more of her teasing.

A while later, Diane stood up and checked me over, seeming happy with the results. “You know, I think your back is just about done. Better turn you over.” She said.

She carefully removed the cuffs one at a time and despite my struggles, she was able to get me flipped over onto my back without me escaping by awkwardly twisting my arms with all her bodyweight until I had no choice but to let my body follow. When I was secured on my back, now with the shorts removed completely from my feet in the process, she opened the bottle of tanning oil and started coating my front in it.

“Oh look who popped up to say hello.” She said, noticing my cock starting to grow again.

“This is just because you’re wearing that and rubbing me all over. Nothing else.” I said, which was mostly true. I had a great view of her tits seemingly trying their best to escape the bikini top. The view was improved by the fact that she herself was glistening with the tanning oil.

“Well I’m flattered you find me so sexy.” She said, giving her boobs a little shake.

“Whatever.” I said, before letting out a moan of surprised pleasure as her hand squeezed my cock through the bikini fabric.

“Whoops, sorry, slipped.” She said, clearly lying.

“Yeah, right.”

“I did, I swear I barely saw it.” She laughed as I blushed at yet another dig at my size. Was I really that small?

I must have been laid on my front for almost an hour, baking in the afternoon sun. Diane would keep feeding the straw into my mouth and making the odd teasing comment, but for the most part she just laid there taking in some sun of her own.

“You’re gonna look great in your little outfit on Monday with a nice tan on those legs, although I do wish you would let me get rid of all that hair.”

“Not gonna happen!” I said, rattling the cuffs a little but all I could really do was roll half to one side of me before being forced to flop back onto my back. No way to avoid the beating sun or the tan that would surely follow. At least Diane placed my shades back on my face.

“Okay. Guess I’d better let you up now, don’t want you to get too burned.”

“You’re so thoughtful.” I said, sarcastically.

“Aren’t I just.” Diane removed the cuffs and I was finally free to get up off the bench and escape the sun for a while. “I suggest a quick shower to wash the oil off yourself before you do anything else, I don’t want you greasing up my furniture.”

I mumbled a response and headed into the house to do just that. A cold shower would make me feel a lot better. I discarded the bikini in the bathroom and washed the oil and lotion off of me before heading back into my room to assess the damage.

“Ah, shit.” Standing in front of the mirror, I could clearly see that my skin was currently red and a little burned, but I knew it would even out into a noticeable tan by the end of the day. What was worse, was that Diane’s plan had worked and the skin where the bikini had been was unscathed. There were two clear triangles of white, unburned skin where the top had been and the thong bottoms were also outlined high up on my waist with two thin strings running up and over my hips.

I dreaded to think what it would like in the back, but I twisted my body around to see anyway….”What the FUCK!” Diane had got me good…. “No fucking way…DIANE!” Right above the clear outline of the thong-backed bikini, burned into my skin were five letters: SISSY

I realized that what she had been doing with the spot at my lower back was adding a stronger spf lotion, that’s why she was using one finger to touch it up, she was writing on my back in high factor lotion. Now, thanks to her, not only did I have the outline of a woman's bikini burned into me, but I was also branded as a sissy.

I could hear Diane laughing outside my room, clearly she had heard me yelling to her. “Hahaha, everything okay in there?”

“You fucking wrote on me!” I yelled back, pulling on my shorts and yanking the door open to see her victorious smile.

“Did I? Where?” She asked, acting confused.

“You know where! Look at this.” I turned and pointed to my lower back and heard her burst out in laughter.

“Hahahaha that came out better than I hoped! Guess you should have been a good boy and done what you were told, huh. Consider us even….sissy.”

“Fuck.” I slammed the door in a huff, blushing at the humiliating brand I now wore. I could fix this, I would just have to go outside and eve out the tan. Sure it would mean more time in the sun, but it had to be better than the tan lines.

Before I could consider my plan, however, I heard Paige and her friend return. I looked out of my bedroom window and into the back yard at the pool. Sure enough, the three girls occupied the three sun-loungers. Diane, Paige and I assumed Kim, Paige’s friend. Guess my tanning would have to wait.

After hiding in my room for a while, Paige came and knocked on my door. “Hey, Josh,” She opened the door without waiting for an invitation. “We’re gonna have some beers by the pool, you coming to join us?”

Thankfully I was covered in my shorts and a t-shirt so the tan lines weren’t visible. “Hey, I could have been naked in here.” I said.

“Ha, nothing I haven’t seen before anyways.” She said, grinning.

“Hey, your aunt told you, that picture was-”

“AI? Yeah, right. I know that picture was real. You think I don’t know the crazy stuff my aunt likes to do to guys?” I blushed as I realized that Paige had indeed seen the photo of my frozen and shrivelled cock. “Just come out to the pool, hang out with us. Have a drink. You can’t just hide in your room all night.”

“Fine, I’ll be down in a sec.” I said.

“Great! See you down there, squirt.”

“Hey!”

“Hahahaha…” Paige left the room giggling to herself as I hoped this wouldn’t lead to two women knowing about my small cock.

“It’s not that small!” I told myself, snapping myself away from that train of thought. I had never really considered myself small, average, if anything, but all the teasing since moving in here was giving me some kind of complex.

—

I joined the girls and had a few cocktails by the pool with them. The sun was still warm but it was now late afternoon so it wasn’t quite as direct. Which was good because I didn’t want to take off my shirt or shorts.

“So, what did you two get up to while I was out?” Paige asked, clearly aiming the question at me and Diane.

“Oh nothing, we just laid out here and worked on our tan.” Diane replied. “Can’t you tell? Look at this….” Diane pulled the string of her bikini top to the sides, “...I even have tan lines.”

“Oooh, nice.” Paige said, admiring her aunt's tanning job.

“What about you, Josh? Did you end up with any tan lines of your own?” Diane asked me, grinning evilly.

I tried to stop myself from blushing as I answered. “Maybe, didn’t really check.” I shot Diane a glare but she only smirked quietly to herself.

I hung out with the girls for a while, Kim was friendly enough. She had a similar physique to Paige, similar age, same tight, toned body. “So you like, don’t have a job right now?” Kim asked me as we talked by the pool.

“Well, yes and no. I’m supposed to be doing some work on some new robot installation at the new factory out on Bridgers, but there were some delays so I don’t have a lot to do right now. But it makes more sense to stay here, where I’m closer to the factory for when work can resume.” I explained my situation to Kim.

“Ooooh, so you’re, like, a super computer guy?”

“Ha, yeah something like that. An unpaid super computer guy right now though.” I said.

“Cool, So is Diane letting you stay here for free until you go back to work?” Kim asked.

Diane answered before I had to. “Not totally free. Josh has been making himself useful around the house through the week.” She said as I prayed she wouldn’t add anything more.

“Well at least he’s being useful.” Paige added. “Speaking of useful, someone needs to refill the jug, we’re almost out.”

“I’ll take care of it.” I said, grabbing the pitcher and standing up, wanting to be out of the way before Diane said anything else about the ‘help’ I had been providing.

Just as I stepped past the line of loungers, Diane quickly jumped to her feet. “I’ll come help you-whoops!”

It happened too quickly, DIane jumped up from her sun lounger right in front of me and we collided. I was off balance, mid step and trying to squeeze in between the line of white plastic. I stumbled a little, the arm that wasn’t holding the pitcher flailed uselessly for a second before… ‘SPLASH!’

I crashed into the pool. “Oh my god, Josh I’m so sorry!” I heard Diane say as I spluttered back to the surface of the cold pool.

“It’s fine.” I said, swimming back to the side and using my arms to hoist myself up out of the pool. The disaster struck for a second time. As I pushed my body out of the water with my arms, I felt my shorts get pulled half way down my thighs by the water, exposing my cock to the three girls who were of course watching me intently. I had just fallen in the pool after all. “Fuck” I dropped back into the pool quickly to hide myself from view. But I could see by their faces that they had seen enough. The cold water of the pool was doing me no favors ‘down there’.

I saw Kim blushing on my behalf, hiding her face behind one of her hands while Paige giggled next to her. “Whoops, might wanna tie those shorts tighter, bug guy.” Diane said, clearly ecstatic with this outcome.

“S-sorry…” I apologized for accidentally exposing myself as I climbed out of the pool, much more carefully this time.

“Wow, drinks and a show. We should do this more often.” Said Paige. “Sorry, Kim, Half an hour after meeting Josh and he’s already flashing you his little pecker.”

“It was an accident.” I said, blushing.

“It’s fine,” Kim said. “Shit happens, but I’m guessing it’s pretty cold in that pool?” Paige laughed loudly at her comment while Diane grinned in satisfaction. “Sorry, Josh. I’m kidding. You’re fine, really.” But the damage was done to my ego already.

“I’m just gonna get changed and dried off.” I said, but Diane stopped me from heading into the house.

“You’re not walking through my house dripping all over. Take off those clothes and use this towel to cover your little friend.” Diane said, grabbing a towel from the sun lounger.

“I don’t wanna get changed out here.” I whined.

“Josh, you basically just flashed everyone here, so there’s no point being shy now. Just take off your shirt and wrap the towel around your legs and you’ll be fine.” Said Diane, holding out the towel.

I took the towel and wrapped it around my waist securely before kicking my shorts down my leg. The shorts hit the tiled pool area with a wet ‘slap’ and a dull thud. “Oh fuck!” I said, bending down to grab my shorts after hearing the thud.

“What’s wrong?” Asked Diane.

“My phone was in my shorts pocket.” I said, pulling out the phone to see the screen was just completely black and unresponsive.

“Is it not waterproof?” Asked Paige.

“Not this model, no.” I said, glumly.

“We’ll worry about your phone later, just take off that wet shirt and go get yourself changed.” Diane grabbed the hem of my shirt before I could protest and helped pull the soaked fabric off my body. I kept my back to the girls, hoping the tan lines weren’t noticeable in the low light.

No such luck, apparently. “Josh, why do you have bikini tan lines?” Paige asked. Fuck.

“Uhhhh…” How the hell could I explain this without giving too much away with regards to the weird dynamic between Diane and I?

“Hahaha, that’s just a fun little prank on my part.” Diane said, explaining it for me. “You should see this.” Before I could say anything else, Diane grabbed the towel and pulled the back of it down enough to expose all of my lower back.

“Hey!” I jerked away from Diane, causing the towel to slip more. I managed to keep from completely dropping it but I could tell from the girls' laughter that they had seen more than enough.

“Hahaha, does that say sissy?”

“Were you sunbathing in a thong?”

“How long were you wearing it to get a tan like that?”

“Hahahaha that is amazing.”

“And you have the top to match too!”

I blushed deeply as I clutched the towel around myself, scrambling to think of something to say.

“How did you manage to do that?” I heard Kim ask Diane.

“Oh I have my ways.” Diane said, conspiratorially. “Let’s just say Josh knows not to mess with me now, right Josh?”

“Right.” I said, glaring at Diane. I needed to get away from the situation, partially because of the embarrassment, but mostly because I was starting to get hard again. A combination of the teasing and humiliation was having an effect on me and I didn't want the girls to see it. I headed into the house, clutching the towel tightly around my waist as I shuffled quickly away.

“Hahaha, see you later, sissy.”

“Love the tan lines, very sexy.”

—

Kim had gone home by the time I headed back downstairs. Paige was staying the night so I knew there would be no way to avoid her indefinitely. Thankfully Diane was alone in the living room when I went back down while Paige got herself ready for bed.

“There he is. It’s been a fun day for you, hasn’t it, my little lodger?”

“You could say that. But I think you clearly had more fun than me.” I said.

“Haha yeah I guess it was pretty fun. But hey, you brought it on yourself….mostly. So, going to behave yourself now?” She asked.

“Behave how?”

Diane lifted her hand to show that she was holding the damn chastity cage. “Paige is still here, and I know how much she likes to have her fun, especially when there are boys around. So put on the cage, like a good boy.” Diane said, “Or don’t, I’ll just have to come up with more ways to punish you whenever Paige comes over. Either way is fine with me.”

As much as my cock and I liked the idea of Diane punishing me in her own special way, today had been humiliating and I really didn’t want another repeat. So I gave in and agreed to wear the cage, just for the night while Paige was here.

“There, it’s on.” I said, handing the keys back to Diane as I exited the downstairs bathroom after locking the chastity cage back on. “But only while Paige is here.” I added.

“Of course.” Diane said, pocketing the keys. “Oh, by the way, I tried to dry out your phone while you were upstairs but I think it’s completely dead. Sorry about that.” She said, sounding sincere.

“Ah shit. I really need my phone in case I’m needed at work.” I said. “And I can’t afford to replace that, smart phones these days are like a thousand bucks for a decent model.

I saw Diane’s light up at my comment. “I know, I’m sorry, but hey, don’t worry, I’m sure we can work something out.”

“What do you mean?” I asked, a little worried about her response.

I saw that devilish grin as she replied. “Oh I don’t know, but I think a small adjustment to our working arrangement could be made in return for me buying you a new phone. But we can talk more about that later. Goodnight for now…sissy.”

End part 4