The Landlord

Being a sissy in private is one of life's greatest pleasures. Getting all dolled up night after night, my collection of impractical feminine clothing growing rapidly, taking pictures to share with strangers online. I loved everything about it! The teasing, the compliments, seeing other sissies and CD's like me, all made for an exciting, enticing, and wonderful experience.

That was, until my landlord Jeremy had the NERVE to find out.

A nice man, certainly friendly with all the tenants in the building, I knew him as well as you could expect to know your landlord. His place was on the same floor as mine, often passing him in the hall, offering a smile each time in my direction. On occasion I had left to go out for girls nights, and Jeremy would always make sure to whistle as I left, often resulting in a blush for the walk to the bar.

One day however, I was in a rush to get home, a new package in my arms. I always got so excited when I had a new toy to play with, or outfit to try on, and couldn't wait to dive into it! Jeremy and I chatted for a few minutes, but it was clear I was brimming with excitement to leave.

"Well, I won't hold you. Enjoy your night." Smiling, I waved and turned to go. Just as I took a step, he added, "Rory."

I froze in my tracks. Rory was my feminine name, a name my friends knew well. But more importantly, it was the name I used online, for all my sissy shenanigans. And Jeremy, while very nice, was not one of my friends.

I turned around slowly, eyeing him suspiciously. Did he overhear it one day? Did I let it slip in one of our convesations? But the smug bastard's grin on his face smacked me with the simple realisation...he knew.He knew!! Jeremy simply laughed, playfully winked at me, and walked inside his apartment.

My face burned with shame as I slammed my door.How did he know!? I scoured through all my photo's, trying to see if I had accidentally slipped and let one with my face through, but they were all cropped or blurred out. Then, staring at the similar background I used for most of my sexy time shots, it dawned on me. These apartments were all the same! Same layouts, walls, even the damn cabinets. Of course he'd recognise it!

I groaned, trying to ignore the excitement building in my clit. This was my second week caged, already overcome from the aching sensation between my legs. I couldn't ignore the package in my hands any longer, taking out my new dildo. Thick, with different layers as it went down, needing to stretch my ass to get through each one, I softly whimpered holding it in my hands. No amount of embarrassment was going to stop me from using it, the need churning through my body demanded I take care of it.

Two hours later, covered in lube and cum, I sighed happily, the interaction with Jeremy chased from my mind for the moment.Worth every penny, I thought, my legs quivering as I slid the new toy out of me. Too drained to move, I didn't even bother cleaning up, passing out in exhaustion, a big smile on my face.

The next day, coming home from work, I dreaded seeing him, secretly hoping I had been wrong and it was just a coincidence. But there he was by the mail, a knowing grin shot my way as I blushed deeply, checking if anything had come in.

"Good evening, Rory. Work not too...hard today?" I glared at him as he laughed, thoroughly pleased with himself. Jeremy lingered checking his own mail slot, eyes never leaving me. I had never felt so humiliated before! Finishing collecting my bills and circulars, I locked the tiny slow, practically running up the stairs. Safely behind my door, I let out a breath I had been holding in, my caged little clit enjoying his teasing FAR too much!

A few hours later, I had a knock at the door. Seeing Jeremy through the peephole I groaned, slightly afraid of what would happen. Would I have to move? Was he just teasing? How far was this going to go? I opened slowly, greeted by a friendly smile. As he didn't say anything at first, I sighed and let him in, thanking me as he walked by.

As I prepared to launch into 'the talk', Jeremy beat me to it. "So listen, I know I've been bugging you the last few days about 'Rory'", that smug smile returning once more. "But I just wanted to make sure you knew it was just that. I'd never take it further than friendly banter, promise." I sighed with relief, the tension in my shoulders dissipating instantly.

I made some coffee and we talked, trading stories back and forth. How I got into it, what I loved about it, and why it excited me so. Jeremy also talked of his past relationships, how certain kinks had made them difficult, and feeling like he had always wanted just a bit more. I smiled, knowing full well from my own experiences, exactly what he meant.

By the end of the night we were both laughing, visibly relaxed around one another. Although he certainly didn't let me off easy, asking all sorts of questions, my face a permanent blushing mess. As Jeremy got up to leave, I thanked him for being so cool about all this, and not making it a big deal. He smiled, giving out a friendly squeeze of my shoulder.

Turning in the doorway, his evil grin returned to his face. "You know, my apartment is often a mess on weekends, I'm all thumbs when it comes to cleaning. Would you happen to know of a maid I could talk to...?" I slammed the door on him, glaring through the walls as I heard his laughter slowly fade into the distance.

Over the next few weeks Jeremy and I became closer, talking over coffee and our mutual love of hockey. I still hadn't unlocked my clit since my last escapade with my new dildo, and the feeling of being so open around him made it all the more difficult to focus. Kind, friendly, and never pressing me for details, my trust in Jeremy just grew to a point where I couldn't help myself slipping into my more feminine persona.

The next time he joked about me cleaning his apartment, I said yes.

Stepping out of his bathroom, my classic maids uniform donned and ready, I felt my face burning as he cooed and whistled. Luckily a thrown pillow stopped his embarrassing praise of my outfit, and I set to work to keep my mind off his lingering eyes.

This. Was. Not. Easy!

Every chance he could, Jeremy made sure he was in the way, glaring as I had to ask him to move over and over. Then it was requesting curtsies, as it was 'part of being a maid, after all', to which I unfortunately caved to. Hands daintily to the side, holding out the hem of my dress, I relented to each of his requests. Even all the times he 'accidentally' dropped something for me to pick up, knowing in my heels that it exposed my panties.

Despite the dangerous levels of sass I felt for him at that moment, and the permanent blush on my face, I did have to admit this was fun. As fun as it was to share with strangers online, having someone I trusted see Rory being the fun, playful sissy she loved to be was...nice.

Finishing my duties as his maid, I internally beamed at the spotless apartment he now had. Well, it was cleaner than when I arrived anyway, being a maid wasn't my day job after all. As I curtsied a final time, expecting some snide remark, suddenly I felt Jeremy close to me. His firm hand rested on my hip, a tiny little moan escaping my lips before I could stop it. So close I could feel his breath, those beautiful eyes of his were locked on me, so captivating and intense.

"Rory, thank you." His lips were centimeters from mine, feeling his breath on my face. "I, uh, was wondering if you'd be okay if-"

Jeremy didn't even make it through that sentence before I kissed him. Taken aback at first, he recovered from shock, taking me in his arms and returning the kiss. Unable to help myself, I openly moaned, lost in the sensations of being kissed by this gorgeous man. I didn't care what this meant, or how it complicated things, I just knew I needed to kiss him.

After several minutes, we were both hot, intensely staring into one another's eyes. He brushed strands of my wig away from my face, smiling down at me, somehow still taller than me in heels! His hand reached up to cup my chin, whimpering from his gentle touch.

"You know, for someone who is supposed to be a submissive sissy maid, you are very forward." I giggled, blushing as I looked away, trapped in his controlling embrace. "We will have to work on that, Rory." I whispered that I was sorry, not meaning it in the slightest.

My maid uniform back in its protective carrier, I walked back to my apartment on shaky legs, thoroughly enjoying the whole experience. Jeremy did too it seemed, because cleaning his place each Saturday had now become a 'requirement', as he put it. A requirement I was happy to oblige.

A month of our weekly sissy maid sessions, as well as continued hockey nights, and suddenly Jeremy and I were very close. Neither of us really were interested in a relationship, but the prospect of being his submissive was obviously something we both were thinking about. After finishing one day, waiting dutifully while he did an 'inspection', which was him simply walking around going, "Hmmmmmm" and "tsk tsk", I meekly interrupted him before he turned my mind to mush with his kisses.

"Jeremy, I-uh. Well...I was thinking. I mean, I've been thinking about it for a while. Not a long while! Just a while, you know? And, uh." He smiled as I stumbled through what I wanted to say, getting so close to me with his beautiful face, his strong hands holding me tightly to his body.

"Go on, you were saying." That smug, knowing smile on his face, I hated it! Pouting, stomping my heels in his general direction for making me say it, Jeremy was not making this easier!

Finally I sighed, glaring at him while I spat it out. "Okay fine! I want you to be my keyholder!" My face a blushing mess, I stared at my feet, unable to look him in the eye. Jeremy's hand tilted my chin up, forcing me to pay attention. I whined, so embarrassed as he held me there, my poor clit screaming at me under my uniform.

"Rory, I would be delighted to be your keyholder." I giggled with relief, overcome with joy that he agreed!

"On two conditions." WHAT!? My eyes widened in fear, already so excited to have a keyholder. I wish he'd stop grinning at me, that all knowing look in his eyes! Jeremy just laughed at the emotions on my face, continuing.

Ensuring I was paying attention, he dramatically raised a finger in the air. "One. I shall require a blowjob every day."

"EVERY DAY!?" I blurted out, shocked completely. Jeremy nodded, trying very hard not to smile, keeping up with his stern act.

"Every day, Rory. The time of which is entirely up to you."

"Oh wow, you are so generous..." He smiled through my sass, ignoring the eye roll I sent his way.

"Two!" A dramatic two fingers in the air, he was having FAR too much fun with this! "It has been clearly obvious how eager you have been to be fucked. After all, I've read all your stories. So I feel there should be a cost for such a service. A trade, if you will."

I couldn't even answer, blushing in Jeremy's hand, knowing he was indeed right. It had been a constant thought every Saturday, sneaking glances at the bulge in his pants. Apparently he had noticed, dammit.

Jeremy kept me focused, continuing with his demands. "Every time you beg for me to fuck you, it will cost you two more weeks in your cage." I whined, protesting that two weeks was far too much time, but he simply shushed my little outbursts. "Two weeks, sissy girl. That is more than fair I feel." I pouted. So if I ever wanted to be let out, I couldn't ask to be fucked for two weeks!? Being around him all submissive and feminine, with the knowledge that bouncing up and down on his cock was an option, I knew that would not be happening.

"One week?"

"No."

"What if I had to clean after each time!?"

"Oh, you'll be doing that anyway." Grrrr!

"But...please!" I pouted at him, even trying to bat my lashes all seductively. But Jeremy playfully poked my nose, the blush returned to my cheeks.

"Those are my conditions for being your keyholder, Rory." He smirked, "for now." I whined, unable to go anywhere in his grip of me, running out of willpower not to agree. This had been something I'd wanted since the first time I showed him Rory in all her glory, my pretty maid dress making me feel so cute and submissive. But those were ridiculous demands!

Yet those eyes softened my resolve, stealing any inkling of resistance I had. I ignored the pulsing protests between my legs, knowing my poor clit would not be happy, and nodded.

"There's my good girl," Jeremy smiled, kissing me deeply as I moaned, sinking into his arms. I knew future Rory would hate me, but as I fell under his control so easily, agreeing was definitely the right choice. Making it 'official', I took my keys out of a little pocket in my dress, keys that I had been secretly bringing for weeks now, handing them over with a slight tremor.

I watched them disappear into his pocket with a smile, my heart beating in my chest. I had a keyholder! A real keyholder. He pulled me close once more and I moaned, still not used to how strong he could be, firmly held in place while we kissed. When we both came up for air, I was a wide-eyed mess, ready for anything my new owner commanded.

Jeremy grinned at the state he had me in. "Now then, let's call this day one, shall we? Day one of fourteen." I whimpered, hearing that officially made my clit instantly ache. Taking me by the hand, he led me to the bedroom, laying down as he positioned on my chest. Arms pinned to my sides beneath his legs, I watched with excitement as he brought out his cock for the first time, resting it on my face.

Big, thick, and more beautiful than I could have imagined, I moaned happily as I immediately ran my tongue along it. Already hard from all the excitement of the day, Jeremy let me take control, staring down at the sissy he now had control over. I licked every part of his cock I could, lost in my new daily duty. I couldn't believe I got to do this every day from now on!

Taking him inside my mouth, I smiled from his own groan, feeling his hips begin to move back and forth, fucking my face into the mattress. I let out my own girlish moan, staying still and open while my keyholder held my face on either side, slowly moving his cock in and out of my eager little mouth. My eyes were glued to him, so happy to have someone to serve, someone to please. I was now his good girl, and I took that very seriously.

Staring down at me, my uniform, and the kinky exciting afternoon we'd had were too much for him. Cock pulsing, I moaned as the first burst of his orgasm hit the back of my throat. His grip tightened, groaning loudly as my mouth was coated completely with his cum, lips locked around his cock. Sighing with relief, Jeremy relaxed his grip on my head, shivering as his sensitive head slipped away from my lips.

I giggled up at him, showing off what a good girl I had been. Concern spread over his face initially, "are you okay with...". I nodded, swallowing every bit of cum that had been gifted to me. Jeremy smiled, bending down to kiss me, before giving me his cock once more to clean. I was his maid, after all. He sighed, head tilted back as I gently caressed his softening cock with my mouth.

"Everyday, huh?" I giggled, seeing the smile spread across his face, noticing the enjoyment he got out of me being a sassy brat.

"Everyday, baby girl. Don't forget it. Or maybe I leave your keys in the main lobby..."

I gasped, eyes widening in fear. "You wouldn't!"

Jeremy grinned. "Only one way not to find out, Rory. You just worry about being a good girl for me from now on." I glared up at my keyholder, that smug look returned to his face. He pulled me up to sit in his lap, melting once more as we kissed. As I left his apartment later that night, I couldn't help the giant smile spread across my face, only slightly terrified of spending the first night without my own keys.

True to his word, each day I found Jeremy's cock in my mouth. On my knees, pinned down, face fucked, tied up, I even woke him up one day, climbing under the covers. Every. Single. Day. He even had a collar for me made, bright pink leather with an appropriate tag,Sissy Cocksucker. I hated how much I loved wearing it.

Each time I took his cock in my mouth. Each time he rubbed his cum over my lips. Each time I happily swallowed, showing him I'd been a good girl. Each time, my urge to beg for his cock inside of me grew. A lot. At first I decided out of spite I'd not ask in the first two weeks, showing him EXACTLY what I thought of his smug, little rule.

I lasted nine days.

Monday night, as he held my wig, pumping his cock down my throat, I caved. I begged for him to fuck me, to use my slutty little sissy ass as hard as he could, and make me cum. Each night I tossed and turned, caged without control, the desperate need surging inside of me. I blushed through the knowing look Jeremy shot my way, promising to take care of his good girl.

The next night he surprised me with a gift, a vintage black lingerie set. With a whimper, I stripped for him, watching as he slid beige nylons up my legs, my twitching clit giving away my excitement. He wrapped the outfit around me, taking his time as he tightened it slowly, seeing his sissy fall further into herself. The black nylon and lace hugging my body, built-in garters connecting to my stockings. It was easily the most turned on I had ever been.

Bending me over, he stretched my eager hole with a plug, letting me get used to its size as I serviced his cock. As I got him close, however, he pulled me away. "Not tonight, baby girl. I'm going to fill that beautiful ass of yours, instead." If I had been allowed to wear panties, they'd be soaked.

Moaning, practically shaking with excitement, I arched my back on my bed, feeling him slide the plug out of my greedy little hole. I was ready, more ready than anything to be fucked for the first time. A real cock, not the multitude of dildo's I owned, but his. My keyholders. Jeremy's hands betrayed his own eagerness, landing playful slaps on my ass as he rubbed his cock up and down my cheeks. My mind was on fire.

He wasted no time, pushing his cock deep inside of me, my ass swallowing his entire legnth. I nearly screamed, not even lasting until his third thrust, cumming hard all over my sheets. Jeremy smirked, calling me a desperate sissy indeed. Whimpering, still shaking from my orgasm, I couldn't even speak as he pressed on, thrusting in and out of me. Thankfully, his rule didn't specify how many orgasms I was allowed.

By the time I heard him groan, pushing deep inside of me as he came, filling my ass with cum, that number was five. As Jeremy pulled out of me, I whined, needing the break but also sad I couldn't feel his cock anymore. He gently kissed up my back, gripping my ass in his hands, listening to me moan and squirm.

"There you go, baby girl. All nice and cummed out." I whimpered as he ran a finger over my clit, a complete mess of cum still leaking from me. "And it only cost you two more weeks in this pretty cage for me." As I layed there, a smile on my face, thoroughly enjoying his hands on my body, I knew it was completely worth it.

However, in those three weeks, I broke down and begged him to fuck me three more times.

Jeremy was cheating! Always feeling me up, running those wonderfully strong hands all over me, squeezing my ass in his palm. I left his apartment every Saturday with a complete mess in my panties, leaking uncontrollably! His cock was just too good at making me cum, more so than my own toys. I was addicted.

Six months later, staring down at my poor caged clit, I knew I was completely fucked. Jeremy had me wrapped around his finger entirely, obsessed with how good he made me feel. He took great pride in reminding me of my 'debt', as he called it, now up to a year of chastity. A year! I couldn't go a year without him fucking me! Not a chance now.