Fiona stepped forward, leaning in close so I could smell her sweet perfume. Her large breasts pressed against my chest, making my lingerie rub softly across my skin. My penis grew harder and my body trembled against hers.

“Do you want to please me?” She said, in a serious tone.

“Yes, Miss Fiona, all I want to do is please you!” I replied eagerly.

“Good because I’m going to make you do whatever I want from now on. Let me be clear about this. From this moment forward you are not a man. You’re my submissive maid, my toy made to serve me.”

She stared into my eyes, awakening a deep-rooted sexual desire that lay dormant inside me until now.

“Do you understand?”

I nodded quickly, “yes, Miss Fiona, I understand.”

Her smile widened, “then we shall begin!” She roared, tugging at my leash and pulling me towards the bed. I was still getting used to the heels as I teetered behind her, trying desperately to maintain balance.

Fiona pointed down at the ground by her feet and without a word, I sunk to my knees in front of her.

“Good girl, Brianna,” she said with encouragement, unzipping her pencil skirt and letting it drop to the floor around her feet.

My pupils dilated and my tiny penis grew painfully hard, throbbing underneath my maid’s uniform. Slowly, my eyes panned up, from her gorgeous shiny black stiletto heels to her sheer stockings that perfectly wrapped around her slender legs; and her delicate garter belt and sexy silk pink panties.

She was the epitome of femininity, a stunningly powerful and sexy woman who commanded respect.

“I’m going to allow you a treat, Brianna,” she said, sitting down on the bed, her crotch just inches from my face.

“First, you are going to perform a task for me. I suspect that you’ve gone down on a girl before haven’t you?”

I nodded quietly.

“That’s good, because that is exactly what you are going to do. I am going to make you an expert at eating pussy and if you perform well, afterward, I may allow you a little treat. Does that like fun to you?”

I nodded again.

Fiona laughed, “good because I wasn’t really asking you, I was telling you!”

I watched in awe as she unclipped her garter straps, releasing them from her stockings, then slowly removed her silk panties. They slid easily down her legs, stopping at her feet and dangling from her heels.

She thrust her foot into my face, making me smell the musky scent of her pussy on the panties. “Lick them!” She ordered.

I opened my mouth, feeling the sensation of the silky material rubbing against my tongue, closing my eyes, and enjoying the taste of her pussy odor, letting it overwhelm my senses.

“You like that, don’t you?” Fiona proclaimed, pulling at my collar and knocking me off balance.

I stumbled towards the bed, landing face-first between her legs. The scent from her pussy now filling my nostrils, making my cock twitch with excitement.

“Stick out your tongue,” she barked, tugging at the leash and forcing my mouth towards her pussy lips. “Now, slowly, lick my pussy lips.”

I began running my tongue over her labia, licking desperately at her clitoris, eagerly trying to please her. As I bent over, I could feel the maid’s uniform stretching around my ass, pulling tightly on the base of the plug and pushing it firmly further into my tight hole.

“That’s right,” she moaned, “flick your tongue against my clit.”

My cock was twitching and I couldn’t help but reach down to touch myself.

“Hands where I can see them!” Fiona vociferated loudly, grabbing my arms and placing them on her thighs.

The feeling of her sheer stockings reminded me of what I was wearing, reviving my arousal and sexual cravings as I began sucking vigorously on her clit. My mouth engulfing her labia as I lapped at her pussy, flicking my tongue against her clit quickly.

Fiona’s moans increased in volume, “Yes, baby! Suck on that clit, use your mouth to suck while you flick your tongue!”

For several minutes I clung to her stocking-clad legs, lashing against her clit, moistening it with saliva, and flicking my tongue faster. Her moans filled the room, making me think back to all the late nights I spent listening to sex noises through the motel walls.

This was so much kinkier, it made my cock rage between my legs, just begging to be touched. My balls were ready to burst and I could barely restrain myself, clinging on to Fiona’s legs as I plunged my tongue deeper inside her, salivating all over her pussy.

The plug inside my ass felt amazing, as I rocked and gyrated my bum against the floor, enjoying the sensation and continuing to please Fiona’s pussy with my tongue.

I carried on like this for another twenty minutes or so, until my jaw ached, listening intently to Fiona’s moans as she grew closer and closer to an orgasm.

Each time I gasped for air, she tugged at my leash, pulling me back down between her legs. Then without warning, she wrapped her hands around my head, forcing her pussy into my face. Her whole body convulsed and shook as she ground herself against my face.
“Yes!” She screamed, “suck my pussy, you nasty little slut!”

I could barely breathe. My mouth pressed hard against her mound, suffocating as she trembled and held on to me tightly, grinding her pussy harder against my face.

She let out a long and loud moan that reverberated around the room. Finally, she let go, allowing me to take a vital breath of air as she collapsed backward onto the mattress, panting heavily.
For a few minutes, she lay still while we both caught our breath. then signed with satisfaction.

“Well, that was nice,” she proclaimed, sitting back up and lifting herself off the bed.

I leaned back onto my legs, still kneeling down, the plug resting nicely against my prostate. My cock poked out under the dress, visibly oozing in pre-come.

“I suppose you are just bursting to come now aren’t you?” She said, looking down at me sympathetically. “Well, I guess I should keep to my word. Come on then, Brianna. You’ve been a good girl. I’m going to allow you a little treat now.”

She peered down at me, bending over slightly so I could get an eyeful of her magnificent cleavage. Then, in a stern and sullen voice, she whispered in my ear.

“I will let you touch yourself just this once, this is your reward for being such a good little girl. I’m going to count down from ten and then you will come for me. Understood?”

I nodded my head quickly, my eyes fixated on her breasts. “Yes Miss Fiona, I understand, thank you.”

“Ok, then, you may start.” 

My hand shot between my legs, reaching down for my throbbing penis, already dripping wet with pre-come and frenzied with lust.

“Ten,” Fiona began counting. Standing over me while I frantically stroked my aching cock, my eyes wild with lust.

“Nine,” she continued, watching me moan and bounce, writhing on the floor as the plug pressed harder against my g-spot.

“Eight.” I could feel my balls tense. The familiar rush of blood pumping its way around my body as the euphoria took over.

“Seven, come on Brianna, jerk that little clitty for me,” Fiona whispered in her sexy husky tone, sending shivers through me.

“Six,” I could feel the come about to blow. Savoring every detail as I stared up at her, admiring her gorgeous curves and her effeminate beauty.

“Five,” she looked down at me, brushing her Stiletto’s gently underneath my balls while I jerked myself faster.

“Four,” my cock had never been harder, my body was quivering from her touch.

“Three, do you want to come on my heels slut?”

Her question pushed me over the edge, completely losing control as I began shooting thick creamy streams of come all over the toe of her heels.

“Oh my god!” I moaned, “I’m coming!” My anus tensed around the silicone plug as more and more streams continued to explode out of my cock, completely covering her shiny black Stilettos.

“Yes Brianna, let it all out,” Fiona whispered, “empty those balls for me, I want to see every last drop!”

More come continued to ooze out of my cock, my whole body tingling and shaking uncontrollably. I’d never produced so much come before and I couldn’t believe how good it felt.

“Good girl,” Fiona said, smiling at me. “And I didn’t even finish counting! You nasty little bitch!”

There were still a few drops trickling out the tip when I finally let go of my cock, looking up at her with a stupid grin on my face and panting heavily.

Fiona looked down at her foot. “Well, well, didn’t you make a mess,” she exclaimed. “I think you better clean that up then hadn’t you. Come on, lick my heels clean.”

I bent down reluctantly. I’d never actually eaten my own come before and I wasn’t sure about it. The plug in my ass was beginning to feel strange and now that I had orgasmed, I felt embarrassed about being degraded like this.

“Come on Brianna, lick them clean!” Fiona commanded, pushing my head down to her feet and spanking my ass lightly.

The first drop of fresh come touched my tongue, making me wince as I ran my mouth up the side of her heel. I felt so depraved, so shameful. What would any of my friends or family think if they could see me now? I thought, sucking the warm come off her shoe and holding it in my mouth.

It tasted so bitter, and salty as it swished around on my tongue. I was frightened to swallow any of it and just continued to gather the remaining loads; using my tongue to scoop it up into my mouth.

When I was sure the stiletto was clean, I looked up at her, holding the massive load of come in my mouth, with my lips closed tight.

Fiona bent forward, reaching for my jaw, and lifted my head up with her hand as she leaned in, staring deep into my eyes. “Good girl’s swallow baby. You want to be a good girl for Miss Fiona don’t you, Brianna?”

The sun was coming down over the horizon creating an orange glow through the curtains that made her skin look stunning in the light. The outline of her body was beautifully silhouetted, accentuating her curves, making her appear luminous and goddess-like.

As I admired her contours, entranced by her beauty, I nodded, swallowing my thick warm come for her, wincing at the taste as it slid down my throat. 

“Good girl, Brianna!” She said, her voice cracking with amusement. “Time for the next stage in your training.”

The taste of come made my throat feel dry and parched as I watched her wiggle across the room and pick up the cock cage, then hurry back over excitedly.

“Stand for me and lift up your dress,” she insisted, grabbing the leash and pulling me back to my feet.

I was feeling dizzy from the orgasm which had made me all wobbly and lightheaded, stumbling slightly as I tried to stand in my heels. Fiona approached me slowly, lowering her voice and speaking in a stern demeanor as I pulled up the hem of my dress exposing my tiny limp penis.

“Listen to me, Brianna. I’m going to tell you something important about yourself, something you need to know.”

I listened intently.

“Your brain is wired for sex and your body is a slut. You have an addiction and I have the cure. Your body needs to be taught to be soft, to be feminine, and to realize that it isn’t going to be having any sex from now on. This requires a bit of work and discipline from you and I am going to train you properly.

From now on, you will wear a plug at all times apart from potty time, and when you do need to go, you will do so sat down, just like a girl. And IF I allow you to masturbate, you will do so either while playing with your sissy pussy, or with something inside your sissy pussy.”

Fiona continued to talk, securing the cage around my soft penis, as she picked up the tiny brass padlock.

“You are now my property. My little sissy. And being a sissy is about being a submissive.”

I could hear the cage being locked around my flaccid penis. The sound of clicking as it closed, then watching as she held up the only key in front of me.

“This is going to be so much fun for me and eventually, so rewarding for you. Is that understood?” She asked expectantly.

“Yes,” I replied.

“Yes, what?” She snapped.

“Yes, Miss Fiona.”

“Good sissy. Now run along, I want to be alone for a while,” she said, picking her skirt off the floor and sliding it back on over her legs.

I stood stunned, still holding my maid’s dress up, my tiny caged clitty dangling exposed between my legs. “Umm, Miss Fiona, please may I get changed first?”

Fiona tutted, making it clear she wasn’t impressed. Then without a word, walked over and hiked my dress up over my head, removing the maid’s uniform. I stood confused, naked except for the Basque and stockings, watching as she stuffed the dress into one of the shopping bags along with the bottle of lube.

“You may cover up now, but keep the lingerie on underneath your clothes at all times,” She said, snatching the heels off my feet and shoving me into the bathroom.

I threw my clothes on quickly and headed back into the room. Fiona waited impatiently by the door holding a large shopping bag, summoning for me to hurry up.

“Here,” she said, thrusting the bag into my hands. “There are some things in there you’ll need. Don’t worry, you’ll figure out what they are for later! Oh, and I have an assignment for you too.”

She looked me square in the eyes, reaching down to grab my crotch and rattling the cage as she spoke.

“At some point, you’ll get the urge to watch porn, and when you do, you must only watch close-ups of girls sucking cock. You may NOT watch anything else. I want you on a strict diet of cocksucking only!”

She paused for effect.

“Is that clear?” Squeezing my balls gently, causing a tiny pain that made me flinch.

“Yes, Miss Fiona, I promise,” I replied timidly.

“Remember, blow jobs only! Now off you go. Come and pay me a visit around noon tomorrow for your next assignment. Bye for now, sweetie.”

She slapped me on the ass and shoved me out of the room, slamming the door behind me. It was dark now and the cold air made me shiver. I clutched the bag tightly and began walking briskly back to my room.

I felt so scared in the darkness, hurrying along the corridors, praying that no-one would see me. When I finally stepped inside my room and the door clicked shut behind me, I sighed a breath of relief and leaned back against the doorframe.

What was that? I thought, feeling a strange sensation in my ass and suddenly remembering that I was still wearing the plug. It barely even registered anymore but it was definitely there, and it felt comforting somehow.

Then another thought flickered quickly inside my head, filling me with joy and excitement.

I wonder what else was in the bag?

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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