Owned by the Landlady - part 6 (Patreon)

Owned by the Landlady - 6

Josh - Punished in plain sight

“Josh, why are you wearing my panties?” Diane asked again as I looked between her and Paige, trying to come up with an answer as I blushed.

Option one: Tell Diane that Paige tricked me into wearing her panties for some bet. Paige would deny it, Diane would believe her over me and I would be thought of as a liar and a weirdo.

Option two: Make up something else random and hope for the best.

“I uhhhh, I just….found them and got…curious.” I replied, knowing how dumb it sounded.

“You found them? They were in my underwear drawer, Josh! I know you didn’t just ‘find them’ lying around.” Diane had an angry look on her face and I had no idea what to do or what to say. “Plus. I already gave you some panties of your own to wear. Didn't I?” I was really hoping she didn't bring that up, not in front of Paige at least.

To my surprise, Paige stepped in to answer for me. “I think it’s obvious what’s happening here.” She said, turning to Diane.

We both looked at her for further explanation. “It is?” I asked.

“Yeah, clearly Josh has some kind of crush on you and couldn't resist wearing your underwear. I think it's probably just a fetish thing. I hear sissies like him get up to this sort of thing all the time.” That was not as helpful a statement as I wanted.

“Is that true, Josh?” Diane asked, turning to me. “Are you so much of a sissy that you had to steal a pair of my underwear to get your rocks off?”

What could I say at this point? There really was no good answer outside of the truth, which I knew wasn’t really an option. “I mean….I guess I just thought they were….comfortable.” I answered, blushing at the absurdity.

“Comfortable? You snuck into my room and stole my panties because they were ‘comfortable’. Is that what you’re telling me?” Diane asked.

“Yes.” I replied, fuck it, let’s see what happens.

“You know I'm going to have to punish you now, don't you?” Diane said, the stern edge still in her voice. 

“I guess so.” I replied, hoping she would at least wait until Paige was out of the way.

“Good! Then I may as well get it out of the way now.” Shit. “Put down those clothes.” Diane stepped into my room and sat down on the edge of my bed, her knees together, back straight, surely she wasn't going to…. “You know what to do, Josh. Not like this is your first spanking from me. Now get over my knee.” 

I glanced at Paige who was loving the whole situation, her joy obvious on her face. “Diane, can't we do this later?” I asked.

“No. You stole my underwear, you face the consequences.”

“Well, yeah I understand that but Paige is-”

“But nothing.” Diane interrupted, “If you didn't want Paige to see you getting spanked then you shouldn't have been stealing my underwear like some pervert. Now, get over my knee, or did you forget who currently has the key to that cage on your little dick?”

“Right…” I mumbled something as I walked slowly over to Diane, she had a good point about the chastity cage after all. I felt more humiliated than ever before as I laid myself over Diane's lap for a spanking while Paige was hovering in the doorway, watching the fruits of her devious ruse play out.

Diane pulled my shorts all the way down, leaving just her panties in place, I knew the thin material of the feminine underwear would do very little to protect me. ‘Slap!’ The first blow came down hard on one of my barely covered cheeks. This one didn't hurt that much, but I don't think hurting me was her plan, this punishment was pure humiliation.

‘Slap!’ ‘Slap!’ ‘Slap!’ ‘Slap!’ ‘Slap!’ ‘Slap!’

Diane carried on with the firm slaps to my ass, alternating cheeks in a constant rhythm as my face burned in embarrassment, knowing Paige had a front row seat to my humiliation. 

“Tsss, Ow! Ow!” As my ass warmed up from the constant slaps they began to hurt as my cheeks stung, the pain heightened with every ‘Slap!’ “Oww! Shit.”

“What's the matter, sissy?” ‘Slap!’ “Starting to hurt?” Said Diane.

“A little.” I yelped.

“Good.” ‘Slap!’ “Then maybe you'll learn your lesson. But before I let you up. Paige, would you like to spank the sissy?”

“Wait, what?” I said, shocked. 

“Me?” I heard Paige say, equally surprised.

“Well yes, you were in the house when Josh stole my underwear and tried sneaking around in them, so you have just as much right to punish him. Though I'd go easy on him, he is starting to look a little sore.” 

I could hear the enthusiasm in Paige's voice as she answered. “Good point. I'd be happy to spank the little panty thief.” 

Could this be any more humiliating? I wondered as Paige approached my upturned ass from behind. “Wow, that ass is already pretty red.” Paige said as she prepared to deliver a little punishment of her own.

‘Slap!’ The humiliation was worse than the pain, and the pain was starting to get pretty bad. But now I was being spanked by Paige while laid over the knee of her aunt in nothing but a pair of panties. ‘Slap!’ ‘Slap!’

“Wow, this is fun, look at how he squirms.” Paige said, laughing as she delivered a couple more blows to my sore behind.

“It is quite fun, and I think Josh may be enjoying himself more than he likes to admit.” Answered Diane.

“Ow! What makes you think I'm enjoying this?” I asked, despite knowing that she was right.

Diane answered with a smug confidence, “Because I can feel how his little cock pulses against my thigh, even in the cage I can feel it twitching.” Diane was right, the whole experience, despite being incredibly humiliating, was a massive turn on for me. “I think that's enough for now, dear.” Diane said, stopping Paige from spanking me any more. 

“Awww, I was having fun.” Paige pouted.

“I know, dear, but we don't break the sissy.” Diane said, letting me stand up gingerly. “Besides, I'm sure Josh will give us more opportunities to punish him in the future. It seems to be his favorite pastime lately.” 

Diane stood up and brushed off her thighs before leaving, leaving me and Paige standing alone in the room.

“Happy now!” I said to Paige.

“Hahaha, ecstatic!” Paige laughed. “That couldn't have gone better.”

“Fuck off!” I said while rubbing my ass, before adding, “And you better be gone first thing tomorrow morning!”

“Oh I will, as promised. But I’m already planning my next visit. I can’t wait to see what panties you’ll be wearing when I get back. Hahaha.” Paige laughed her way out of the room as I threw a pair of Diane’s shorts at her from the laundry pile. “And I am definitely spanking you again at the next opportunity.”

—

I gave it a while before I approached Diane, giving her a chance to calm down, maybe come to her senses. I waited in my room before gathering up the courage to go downstairs, still caged, still in the panties, still desperate.

Diane was in the living room, watching something on TV when I entered. “Hey, Diane. Can we talk for a sec?” I asked.

“Of course, sweetie, what’s up?” She asked, as though she didn’t know what was on my mind.

“Well, it’s about the panties.”

“What about them?”

I bit back my annoyance at her non-chalant response. “Well, I was wondering how long I actually had to wear them?” I said.

“As long as you’re under my roof, like I said the other day.” She replied, looking at me intently. “I love knowing that you’re walking around embarrassed and turned on by my panties.” Diane said, confide

“But it’s not like that, really I just-”

“I don’t care, Josh. Like I said, I’m not interested in why. This is both a punishment for you and a treat for me. Now I have a cute boy in my house who is stuck wearing my underwear all the time. Every day.” My cock twitched at her words, she had called me cute and admitted that she liked the idea of me in her panties. I shouldn’t have been surprised really.

It was clear I wasn’t going to change her mind on this, so I moved onto something that should have been more important, my new phone.

“Oh, right, you need to order your new phone. Just find a model that you like and send me the link.” Diane said as though it was nothing.

“You don’t care what phone I order?”

“Nope, as long as you hold up your end of the deal. Your body hair for a new phone.” So that was that.

I deliberately selected the most expensive phone on the market, latest model, highest available memory. If I was going to give Diane another slice of my masculinity then it was going to be worth my while at least.

—

True to her word, Paige was gone by the time I got out of bed the next day. Even better, my new cell phone was delivered early in the morning thanks to Diane paying for overnight priority delivery. I spent a little time setting up the phone and contacting work to let them know I was fully contactable again, as per the terms of my retainer. The only issue I had that morning was selecting which panties to wear from the drawer Diane had filled. I chose what looked like the least feminine, some light pink, cotton briefs. They had a small bit of lace around the waistband with a faint floral pattern, but at least they weren’t satin or silk, or a thong.

More importantly though, was the chastity cage I was still wearing. “Uhh, Diane,” I said as I helped clear up from breakfast, “Paige is gone.”

“She is. Well noticed. Don’t tell me you miss her already?” She said, smiling.

“No, not that. I was actually thinking more about the chastity cage I’m still wearing.” I said.

“Ohhh right, of course. You must be desperate for a little ‘alone time’ by now huh?” Diane said, grinning wickedly.

“Well I was thinking more about how uncomfortable it is.” I lied.

“Ha. Yeah, right. Well I did agree to unlock you when she left so I suppose you can have the key. Besides, we’ll need the cage out of the way later to get rid of all that hair.” Diane pulled the key out from her pocket, as though she knew I would be asking for it. “Here you go.”

I took the key, thanking her quietly before I stood to leave, eager to free myself. 

“Have fun jerking off.” Diane giggled as I left the room.

As soon as I got the cage off, my cock quickly got hard and I was eager to get myself off after the weekend I’d had. The only problem was Diane’s comment. As soon as I went downstairs she would know what I had done, she would have something to say. So I resisted the urge….for now. I was mostly just glad to be free of the cage and actually able to get hard again.

Thankfully, I had my new phone to distract me from my own horniness. As I was checking out the features of my new gadget, Diane knocked on my door. “Josh, almost time for your shift to start.”

“Almost time? I have like forty minutes.” I whined, a little petulantly. I was having fun exploring my new phone.

“Yes, but we have some extra prep work to do before today, so get undressed and meet me in the bathroom.” 

I took off my shirt and socks and headed into the bathroom, still in my panties and shorts. I felt weird just stripping naked and walking into the bathroom, despite what Diane had already seen of me.

“I thought I said get undressed?” She snapped, a little annoyed when I entered.

“Well, yeah, but I-”

“Oh for god’s sake. Like I haven’t seen you’re little dick before. Come on, clothes off, now.” Diane watched as I reluctantly undressed completely. “Nice to see you wearing your panties like a good boy.”

I hated how much my cock twitched at her comments and started to regret not jerking off earlier. My growing erection did not go unnoticed by Diane. “Wow, look how the little guy responds to me. Don’t tell me you’re having impure thoughts about your landlady again.”

“No I…I’m just horny from the weekend being trapped in the cage, that’s all.”

“You mean to tell me you didn’t go straight to rubbing your little pecker when I gave you the key?” She asked, her eyes lighting up with possibility. 

“No, actually I didn’t.” I said, feeling like I won some sort of small battle.

“Hahaha, aww and look at you now, hard and desperate. Is that because I made fun of your small dicky?”

“What?! No, of course not!” I replied, despite feeling like that is exactly what was happening.

“Of course you’re not. Anyway, jump in the shower, little fella. You’re gonna look so much better without all that hair.”

Diane followed me into the shower, fully clothed as there was no water running and carrying a few bottles of what I had to assume was hair removal cream. She started lathering my body up with the strong smelling cream, starting at my neck and working down across my whole upper body. I stood there, hard as rock the whole time as Diane’s hands essentially massaged every part of me.

“Ah. Hey, careful back there!” I said as Diane applied the cream to my ass. She had let one of her fingers brush right up against my ass hole as she rubbed in the depilatory.

“Sorry, Josh, I didn’t know you had such a sensitive ass.” Diane replied, letting another finger rub against my hole.

“Sssstop. I do not have a sensitive ass.” I said as I jumped forward a little, away from her finger.

“Could have fooled me. You ever stuck anything back here?”

“What?! Are you kidding? No, of course I haven’t.” I replied, shocked at her insinuation.

“You’re missing out, from what I hear it can be quite pleasurable for guys.” Diane was working down my legs now, starting at the back and working around to the front and back up until the only part of me that wasn’t covered in strong smelling cream was my crotch. My erection was still bobbing in the air, sticking straight out in front of me.

“Okay,” Diane poured a fresh amount of cream into her hands, “Time for my favorite part. Let’s see what the little guy looks like without hair.” 

“I can do that part myself.” I said.

“No point now, I've already covered everywhere else, may as well do this. Besides, there's not much of it to do.” Diane added a little giggle at her own comment. I stood perfectly still as her hands approached my erect cock. I found my hips jerking involuntarily as soon as she touched me.

“Oohh, someone’s sensitive. Don’t tell me you’re a quick cummer too.”

“Nnng, no!” Diane’s hands were slowly rubbing up and down my cock and all around my balls, smearing the cream all over but I sensed she was deliberately doing way more than necessary.

“Well that’s good to hear, because having a tiny little cock like this one as well as being a little premie would be sooo embarrassing, wouldn’t it.”

“I am not a -ohhh- a premie.” I said, failing to suppress my own moans of pleasure.

“No? That’s good, then you won’t mind me taking my time down here, will you?” Her hand increased speed slightly, her grip a little firmer and I desperately hoped she would stop soon or I’d just end up blowing my load and giving her more ammo to tease me with.

“Diane…I think you got it all.” I said.

“I know, but I need to be thorough. Don’t want to leave any hairs down here. But you seem worried. You’re not gonna lose it are you?” One hand had completely given up any pretense of covering me with the cream and was now rhythmically pumping up and down my shaft, bringing me closer to what I knew would be an embarrassing orgasm.

“No I…I just think you should…fuck!” I gasped.

“Oh-oh, I think someone’s gonna blow soon. Small cock, quick cummer, soon to be a hairless sissy in his cute maids outfit and panties. Mincing around, serving me, curtsying.”

“Haaaa, fuck!” I felt the orgasm hit despite how hard I was concentrating on holding it back. My seed spilled out as Diane kept herself out of the firing line, watching with an amused expression as I jizzed on her shower tiles. “Shit!”

“Hahaha, well, just as I thought, that didn’t take all that long at all.”

“I was just pent up from the cage all weekend!” I said as Diane stepped out of the shower, leaving me standing there with a wilting cock and covered in hair remover, feeling ridiculous.

“Suuure that’s what it was. You’ll last longer next time. Right?”

“There won’t be a next time.” I said, despite having enjoyed her touch a great deal.

“Hahaha, I’m only teasing. Don’t get so worked up. Anyway, it’s time you washed off the cream, let me get the water for you.” Diane reached into the shower and twisted a nozzle, causing cold water to spray all over me.

“Fuck that’s cold.” I said, cringing away from the spray but I was unable to avoid the water completely.

“Is it? Must have forgot to set the temp. Oh look, it’s even smaller now. Hahaha.”

“Shut up!” I snapped, turning away from Diane so she couldn’t see my small cock under the spray. Did I just think of my own cock as small?

—

Everything felt different without my hair, most notably the stockings. My legs were always unmistakably a man's legs, but now, with all my hair down the drain, wrapped in white stockings and my hips hidden beneath the maid dress, it was impossible to tell.

“You look better already.” Diane said, examining me in my work outfit. “Just one more thing to add.”

I sighed. “Right, the cage.” 

“Yes, but not your usual. It's time for a slight upgrade. Something a little more fitting.”

“What do you mean?” I asked.

“Well, the cage you've been using is a little too big for your little guy.” Diane said, opening up a small box.

“What? It's not too big at all.” I protested.

“There's room for your cock to grow, that means it's too big, now stop complaining, it's only for a couple of hours.” Diane held up the new cage, it must have been half as big as the previous one, made of a tough looking pink plastic. I knew there would be no room to grow at all and decided that I would not want to be spending too long in this new cage. I bit my tongue as Diane fitted the new cage onto me, resenting the fact that my cock actually started to grow again, despite Diane making me cum in the shower not long ago.

My attempt at an erection was thwarted by Diane forcefully stuffing the cage section onto my shaved cock and locking it closed quickly. “Awww! Look how cute it looks now.” She squealed in a condescending tone.

“Do you have to do that!” I complained.

“Oh stop complaining. I love guys with small dicks like yours. They’re so much more fun.” Was that actually true? Did she really like my small cock or was this just another way for her to mess with my head? “It may be a little TMI, but I think it’s quite a turn on.”

“Stop it. I know what you’re doing.” I said, despite my increased heart rate at the thought that my cock turned her on in any way.

“Oh stop being so pouty, you have work to do, your shift has already started.”

“Fine,  what do you want me to do?” I said.

“For starters, it’s ‘yes ma’am’ until your shift ends. And you can start by dropping the attitude. Now be a good boy and show me your curtsy.”

“Yes, ma’am.” I grumbled, giving a half hearted curtsy.

Diane led me to my own bedroom to start my ‘shift’. She opened the ‘panty drawer’ she had filled the previous day. “Okay, sissy, your first job of the day is to organise this mess.” She said, lifting a handful of feminine fabric and dropping them to show how disorganised the drawer was. “I want you to arrange them by style, thongs with thongs, briefs with briefs, there’s even a couple of nice, sexy G-strings in here too. I’ll wait here while you finish.” Diane perched on my bed and waited for me to get started. I stepped up to the drawer and reached down, but Diane interrupted me. “Ahem, aren’t you forgetting something? I gave you an order, you should acknowledge it correctly, and don’t forget to curtsy.”

My lips pursed tightly together as I resisted the urge to say something snarky. “Yes, ma’am.” I said, dipping into another curtsy.

“Good girl.” She said, using the feminine pronoun this time.

“I’m not a girl!” I said, turning back to the drawer.

“No, but you’re well on your way. Now get to work.”

“Yes, ma’am….” I spent the next few minutes organising my panty drawer. I hated that it was actually my panty drawer thanks to her and her niece, but I didn’t complain, after all, my room was currently populated by over $2000 worth of Diane’s money.

I decided on a ‘small to big’ structure for the drawer, starting with G-strings on the leftmost side, I couldn’t imagine myself ever willingly choosing to wear one of those. The thongs were just to the right of the G-strings, followed by the ‘cheekies’ and the hipster briefs and finally the full cut panties. “Okay, I think I’m done.” 

Diane stepped up close to me and looked over my shoulder at the drawer. “Good job, sissy.”

“Thanks, and stop calling me sissy.” 

“Well what else can I call a young man in a maid’s outfit?” She said, smirking. “Ya know, seeing as we’re in here you might as well give your own room a tidy up. Go grab the vacuum cleaner and some surface wipes….”

Diane had me cleaning my own room for the next half an hour or so, watching me from my computer chair, which was actually just an old, office style chair that was here when I moved in. “You really should replace this chair, you know?” Diane said as I wiped down my desk.

“Yeah, with what money?” I replied, a little harshly. “You do know I’m not earning anything right now?” I added with a little huff.

“Oh right. Sorry, forgot about that. But it’s not forever, keep your chin up.” 

We stayed in my room as Diane ordered me to make my bed, move my dirty clothes, vacuum my carpet. Every instruction she gave me was expected to be met with a ‘yes, ma’am’ and a curtsy. 

“You look so much sexier without all that hair. You have a great ass.” Diane said as I was cleaning beneath my desk.

I reached behind and felt that the hem of the dress was completely exposing my panty covered ass and felt the blood rush to my face. “Stop it”

“Stop what? Complimenting you? You really do have a nice ass, and it’s so much better without all that hair. I can’t wait for my next excuse to give you a spanking and redden those cheeks a little.”

“Sssshit.” I tried to suppress my frustrated gasp, Diane’s comments were causing my cock to try and grow inside the new, smaller, tighter cage, the results were incredibly frustrating. There was no room at all for my cock to grow so the cage just pulled tight against my balls and all the sexual energy had nowhere to go.

“What was that?”

“N-nothing.” I said, “Just the stupid new cage you put me in.”

“Oooh I see, getting a little tight down there huh? Does that mean the little guy is starting to wake up?” Diane said, the amusement clear in her voice. “Is it the spanking talk? Or the compliments?” 

“Neither.” I replied quickly, but it was clear she wasn’t going to believe me. Hell, I didn’t believe me.

“Okay, sissy, whatever you say.”

The rest of that shift was tortuous, Diane had smelled blood, so to speak, and spent the remaining hour teasing me mercilessly about how pretty I looked, my cock size, anything that she knew would cause me to blush. Needless to say I was grateful for the end of that particular ‘shift’ so that I could get rid of the new cage and the outfit. The damn tan lines were still there though when I got undressed, reminding me of my perceived status in the house.

The following morning I woke up with my typical morning wood, the feeling of my bedsheets on my newly smooth skin was a sensation I wasn't used to. I didn’t leave my room right away, instead I logged on to my laptop to check for any emails from work, good thing I did too as apparently there was a meeting that had been scheduled for that morning.

I quickly got dressed and headed to find Diane, my well organised panty drawer a reminder of yesterday. “Morning, Josh.” Diane greeted me when I headed downstairs. 

“Morning, listen, I need some of my male underwear back today.” I said, noting the slight frown that appeared on Diane’s face.

“Oh really? And why is that?” She asked.

“I have a meeting I need to attend at work, apparently everyone from the project has been called in for a progress report and I can’t exactly go there wearing panties now can I?”

Surprisingly, Diane answered with a simple, “Why not?”

“Because I can't! What if someone sees them?” I said.

“Why would you be showing people your underwear in a work meeting?”

“Well I wouldn’t, not on purpose but they might-”

“I suggest you keep your panties hidden during your meeting and everything will be fine. I’m not going to rescind your punishment the second it becomes a slight inconvenience for you, it wouldn’t be a punishment then, would it?” 

“Well, no, but-”

“No buts,” Diane interrupted me again, “Anyway, even if you weren’t wearing panties you’d have your tan lines to worry about, they would be just as visible in the same place. So you’ll just have to deal with it.”

I didn’t have much of an argument against that point, she was right, the tan lines would be there no matter what so if my shirt rode up or my pants slipped down, either my panties would be visible or the tan lines would be. I was going to have to be extra careful in that meeting.

I rifled through my drawer and selected a pair of powder blue briefs that rode deeply into my ass as I walked, splitting my cheeks uncomfortably and rubbing against my smooth crotch in an annoying way that made it tough to ignore what I was wearing. I would have gone with a more comfortable pair, but the waistband of these was the most nondescript I could find in the whole drawer.

I was distracted by the underwear the entire meeting. Every time I moved, I was reminded that they were there, reminded of Diane’s increasing control over me. Annoyingly, I was constantly trying to hide an erection as the material of the underwear rubbed against my cock whenever I shifted in my sheet. Thankfully, I wasn’t expected to contribute to the meeting at all as it was just the director and project lead letting us know the revised roadmap for the work. The bad news, I wasn’t going to be needed for a month, maybe two!

“Um, Mr Peterson,” I half raised my hand to ask a question.

“Josh, go ahead.”

“Thanks, does this mean there won’t be anything at all for me to do until the conveyor system replacement is complete?”

“Yes, unfortunately that’s right. I know, it’s a shitty situation to put you in, pardon my language, but there just isn’t any point in starting to write any script for the robot until we have the timings of the conveyor system nailed down. So we do need to install the conveyors, then commission them to get the timings right before we commission the robot arms.” Peterson was the project manager and the person that had hired me for the job, a fact that I was very grateful for.

He must have seen the disappointment on my face, because he added, “I know, it sucks, and I completely understand if you decide to leave the project to pursue other opportunities. But I’d hate to lose you.”

“No, no. I won’t be leaving the project. I can hang for a while longer.” I replied.

The truth was, I was unproven in the field, any ‘other opportunities’ would be impossible to find with no experience on my resume, this job was my way to get my foot in the door. I was suddenly even more grateful to Diane for allowing me to stay on without paying her anything. Hell, in that moment, I could almost forgive the teasing.

When I got home, it was shortly before I was supposed to start my maid shift, but Diane’s car wasn’t in the drive. Sure enough, the house was empty when I walked in. What was I supposed to do?

Should I get dressed and start work? Would Diane expect me to be dressed when she got back? What would she do if I wasn’t in uniform? “Screw it.” I said to myself, I had just been thinking about how I was grateful for her letting me stay at her place, so why not behave as such?

I got dressed in the humiliating outfit, this time without Diane there to supervise me. I held the small, pink chastity cage in my hand, studying it for a second. The thought of me alone in the house, dressing myself up as a maid, had started to wake up my cock for some reason. I figured seeing as Diane wasn’t here, I could get away without the cage for the day. If she came home I would just slip away and put it on.

I worked for a while, unsure exactly where I should be focusing without Diane there to guide me, so I just moved around the house, straightening out anything that looked out of place. Whenever I caught sight of myself in a reflection I would blush and be reminded of what I was doing. But it was just because I needed a place to stay, and she bought me things.

“Josh, are you here?” Diane returned while I was cleaning down the counter tops in the kitchen. “There you are! And you got started without me, such a good boy.”

I blushed a little at her words, but managed to reply, “Hey, a deal's a deal.”

“And I’m glad to see you holding up your end. It always gets me hot to see a young man feminized and humiliated for me. Did you manage to get your little cock locked away in its new cage?”

Shit! I was planning to run off to the bathroom to put it on, what could I do? I couldn’t lie to her, what if she checked, that would only make things worse. Damn it! “Umm, actually no, I was having a little trouble with that so I’m not wearing it right now, sorry.”

Diane gave a disappointed shake of her head. “Josh, you know that cage is part of your work uniform, we had a deal, you said so yourself.”

“I know, I know, I’m sorry, really. But I was having trouble getting it on.” I said, which was mostly true, my cock trying to get hard had made it impossible to fit inside the too small chastity cage.

“And why is that?” Diane asked, “It fit perfectly fine on your little dicklet yesterday.”

Dammit, why was it so easy for her to push my buttons? “Well, yeah I know but-”

“Is it because your little friend was getting excited?”

“Yeah, well I wasn’t umm, fully, you know…but it wouldn’t go on.” Diane was staring at the crotch of my dress intently.

“I see, so where’s your cage?”

“In my room….” Diane insisted that I take her to my room to get the cage on, so I led her upstairs, my skirts swishing and tickling the backs of my thighs as I ascended the steps with Diane right behind me, no doubt getting a view of my panties.

The cage was left on top of the panty drawer, open and waiting. Diane walked over and picked up the cage, examining the two sections. “I’m impressed that you remembered to get yourself dressed and start work, even though I wasn’t here, so maybe I can let this little infraction slide without any punishment this time.”

“Thank you,” I said, before remembering to add, “...Ma’am.”

Diane gave a half smile, “Good boy. Plays, you did such a good job on your panty drawer yesterday that…” As Diane talked, she had idly slid open my panty drawer as though to emphasize her point. The problem was that I had messed the drawer up this morning while searching for a pair of underwear to wear to work. “Tut, tut, Josh. What is this?” 

“Oh….I uhhh, I was searching for something to wear to work this morning, don’t worry, I can straighten it out no problem.”

“Josh, I was prepared to forgive you for not putting on your uniform as expected, but now I see this mess, after all the effort we put into it yesterday.” Diane advanced on me, slowly, until she was standing right in front of me, close enough that I could smell her perfume. “I guess I’ll have to give you that punishment after all.”

End part 6.