Caught Sissified and Enslaved

It had been a surprisingly comfortable night all things considered. My bounds, while very restrictive, had allowed me drift off fairly quickly without too much fidgeting. The soft touch of my nightwear was also a constant reminder of my feminine journey that was to continue indefinitely.

I awoke to Mistress Ruby caressing my thigh. Her hand then found it's way to my cage.

"Good morning Sissy Evie. I hope you enjoyed your first night. You've got a busy day ahead of you, but if you perform well, you just might find yourself being released from chastity, albeit temporarily. Before your maid duties begin, we need to discuss your punishment don't we? I've been extremely kind to you up until this point but things are going to get harder for you Evie."

With that, Mistress Ruby removed the tape covering my mouth and replaced it with a ring gag, forcing my mouth open.

"Every sissy must learn to enjoy the taste of cum. Whether it be their own or of another man, sissies crave it. You will be no different. I hadn't intended on introducing this so early on but after your little outburst last night, this should help to remind you of what you are to me. You're mine Evie. You're my sissy maid slave and you will do exactly what I tell you to, in exactly the way that I want you to. Any disobedience or resistance will be punished. Take what's about to happen as a warning Evie."

Still emerging from the haze of sleep, I could barely process what Mistress Ruby was saying. She certainly meant business as her tone seemed far more firm.

"Of course, you'll be making me my breakfast this morning, but I thought I'd give you yours now before you start preparing for your first full day as my sissy maid."

With that, she removed my blindfold. Wearing a black lacey babydoll and matching black panties, Mistress Ruby looked absolutely stunning. However, as my eyes adjusted to the light, I soon realised what she was holding in her hand.

"This, Sissy Evie, is a condom, filled with a superior mans cum. After I put you to bed last night, a guy I've been seeing occasionally came over, and boy did we fuck. He must've cum at least three times before I kicked him out" she cackled.

"And now, you're going to drink his cum."

It was at this moment that panic really began to set in. This was about as far beyond my limits as could be, not that any had been discussed of course. Swallowing my own cum would've been bad enough, but cum from another man?

Despite my best efforts, I couldn't move an inch as Mistress Ruby climbed onto my chest, placing her thighs either side of my head.

"Remember Evie, you brought this on yourself."

With my head locked in place and my mouth forced open, I was forced to lay there, awaiting the inevitable.

"You will swallow every drop from this condom. You won't complain, and this won't be the last time you eat cum. Now, get ready Evie."

Accepting my fate, I could do nothing but stare up at Mistress Ruby as she slowly poured the creamy, salty load directly onto my tongue. To ensure there was nothing left, she ran the condom between her fingers, squeezing out the last few drops.

"Swallow it, NOW."

Doing my best not to gag, I managed to swallowed every drop, despite it taking a few gulps.

"There. That should teach you to speak out of turn Evie. I'm going to use the bathroom now. I'll come and release you when I'm done. You can stay here and enjoy the taste of his cum for a while."

This was truly the most humiliating experience of my life. Knowing that I'd just swallowed another man's cum really turned my stomach. Not to mention, the flavour now marinating in my mouth was horrendous. I thought to myself, how do women deal with this?

After what felt like hours, Mistress Ruby re-entered the room, removing my ring gag. She also began unbuckling my bounds, finally allowing me to move again.

"How's that cum tasting now Evie? And make sure you answer correctly slut. Tell me how much of a cum slut you are for me."

"It tastes amazing Mistress Ruby" I say as I fight the urge to voice my true feelings.

After all of my bounds had been removed, I was ordered to take a shower using the girly products left out for me. I was also reminded of my shaving duties which I was going to have to adjust to.

Just as I was finishing up in the bathroom, Mistress Ruby shouted my next set of instructions through from the living room.

"I've put your full outfit for today across your bed Evie. Tomorrow you'll be doing that yourself. Once you're dressed, put on your makeup like I showed you and come meet me in the living room."

"Yes Mistress Ruby."

My outfit for the day consisted of the same maids outfit as last night. Underneath, my lingerie was equally as feminine. A hot pink matching lace bra and panties set contrasted with a pair of soft white stockings and garter ensemble painted a slutty yet classy look in the mirror as I observed my own transformation.

Once I was dressed, I applied my makeup and brushed my hair into a ponytail. Finally, I slid my feet into my heels and locked the padlocks through the holes in the strap. Of course, the keys were nowhere to be seen.

Rising to my feet, I resigned myself to my new life. It hadn't even been 24 hours yet, and I'd already swallowed another man's cum. I simply couldn't afford to face another punishment like that, meaning I'd have to be extra careful on my first day as a sissy maid.

Making my way through to the living room, I could feel my cock swaying back and forth thanks to the weight of the chastity cage.

"One of the most important duties of a maid is to maintain cleanliness. Therefore, you'll be cleaning the entire apartment today Evie. I expect you to finish the kitchen and living room before lunchtime. Before you begin, we need to make some little additions to your outfit."

With that, Mistress Ruby produced a ball gag which she strapped in place. Next were three pairs of cuffs. The first secured both my elbows behind my back. The second attached my wrists in front of me, locking my arms in place but allowing my hands to remain somewhat usable. Finally, the last pair went just above my knees, limiting how fast I could walk. This would also force me to bend down with my knees together, which Mistress Ruby reminded me is how a sissy should.

"Oh, and one more thing. A good sissy is able to take a cock in her ass. A butt plug will help to stretch out your sissy hole before I deem you ready for a good pegging. We're going to start you off fairly small but you will be progressing quickly, mark my words."

Instructing me to bend over the arm of the sofa, Mistress Ruby lifted up my maid outfit and pulled my panties to one side. After applying some lube, she forcefully pushed the plug into my ass as I groaned into my gag.

"You'll learn to love that feeling Evie. Now, you'll start in here, dusting everything in sight before hoovering. I expect you to be done by the time I get back from the gym at 1. I've got a pretty intense workout planned, so be ready to serve me in a variety of ways when I return. Are we clear?"

I nodded, thanks to my ball gag preventing any kind of verbal communication.

I watched in awe as she turned and walked out the door, bending over as she left to pick up her bag. A feeling of weakness ebbed through me as I was once again reminded of exactly what I was. My new life. A sissy maid for the girl of my dreams.

Catching myself in a horny daze, I set about the job at hand. I had just over two hours to complete my first cleaning duties of the day. That didn't sound like a tall order, but my outfit was extremely restrictive. The heels alone were very challenging, let alone having my arms and wrists secured, leaving only my hands partially available while pinned to my sides.

It actually felt quite therapeutic, having a task to focus on. With my desire to please Mistress Ruby, distractions were not an option. I simply could not afford another punishment after what happened this morning, meaning I'd have to complete my task to a very high standard.

As I dusted, hoovered and tidied, I mulled over the position I found myself in. Mistress Ruby already had me desperate to please and comply with her every demand, and I'd been her property for less than a day. In this moment, I really did feel powerless. For the foreseeable future at least, all I could focus on was serving Mistress Ruby. What other choice did I have?

Bang on time, Mistress Ruby arrived back from the gym, still looking like an absolute goddess, albeit a very tired and sweaty one. Plonking her bag down next to the sofa, she collapsed into the sofa.

"Looks like you've been busy Evie. I'll do a proper inspection later. Now, come and kneel at my feet."

My heart was pounding as I made my way over to her. Slowly lowering myself to my knees, I was struck with the most intoxicating musky scent, emanating from Mistress Ruby.

"That was one hell of a workout, let me tell you. Me and Abby really went for it today. I'm sure you'll meet her at some point. She loves a good submissive" chucked Mistress Ruby.

"I think I'm going to put that mouth to use, so come here Evie. Let me remove your gag."

Leaning into Mistress Ruby, her scent flooded my nostrils, causing me to shudder as she fiddled with the buckle behind my head. In the same motion, she also clipped the lead onto my collar, allowing her to control my movements as I worshipped her.

"Let's start with my armpits Evie. I didn't use deoderant this morning, so you won't be ingesting any harmful chemicals. God, I'm nice aren't I?"

"Yes Mistress" I stammered as I prepared to clean her sweaty armpits with my tongue.

The taste was extremely bitter and salty, but I licked eagerly, desperate not to dissapoint. After a few minutes, she untied my elbows and cuffed my wrists together. I was then instructed to remove her shoes.

"Give those shoes a sniff slut. Deeply inhale that scent. The smell of hardwork."

I was lost in the scent of her feet, truly. My love of feet was rapidly growing as I inhaled deeply, savouring each breath.

"Isn't it just amazing Evie. Tell me how much you love it."

"I love it Mistress Ruby. I love smelling your shoes."

"Good girl. Why don't you start massaging my feet for me. I'll tell you when to take my socks off."

I dutifully massaged her feet, following guidance from Mistress Ruby. Her socks were more than damp in places, which did fill me with dread slightly, knowing I'd soon be tasting her toe jam.

"I love a foot massage, so you'll become a pro in no time. Now, take my socks off and start worshipping my feet. I expect them to be completely clean when you're done."

Salty, cheesy, and hot. I must admit, the gym really had done a number on her feet. I resisted the urge to gag as I darted my tongue between her toes, collecting all the debris and bitter toe jam as I went. After what felt like a lifetime, Mistress Ruby released her grip on my lead, allowing me to move my head away from her feet.

"From what I can see, the kitchen and living room look adequately clean. You did well Evie. Now, come here and let me unclip that leash."

"That gym session has left me starving. Go prepare me some food slave. Just make whatever it says on the meal plan on the fridge. When you're done, bring it over to me. Also, bring over a banana and a bowl. We can't have Sissy Evie going hungry now can we? And don't forget to wash your hands. I don't want any foot sweat in my meal."

I unsteadily rose to my feet, the taste of her's still marinating in my mouth. While I loved worshipping a girl as hot as Mistress Ruby, I couldn't help but feel a sense of disgust at what I had just been forced to do. The reality of the situation I found myself in was beginning to set in.

I prepared Mistress Ruby's lunch as quickly as I could, desperate to get something for myself as I was yet to eat anything at all... other than another man's cum of course.

Bringing the plate, as well as the banana and bowl over to Mistress Ruby, she was impressed with my efforts.

"This looks delicious I must say. You're a natural maid Evie! While I eat, peel this banana and put it in the bowl. A sissy needs maintain the correct diet. After all, your body is going to become completely feminine as time goes on."

With the banana now in the bowl, I eagerly awaited permission to eat. However, to my disgust, Mistress Ruby instead decided to begin squishing it between her toes. Was this some sort of sick joke?

"Go on Evie, tuck in."

Reluctantly, I lowered my head, not wanting to disobey my Mistress. The taste was one thing. The feeling of licking mushy bananas out from between her toes was something else.

After somehow finishing my lunch, it was now time to continue my maid duties.

"I'm going to take a shower so why don't you do the washing up. Once you're finished, come and kneel outside the bathroom and wait for me to come out."

"Yes Mistress Ruby."

I teetered off back to the kitchen to tidy up, washing the dishes and binning any rubbish. Every click of my heels on the hard floor reminded me just how painful these shoes were.

Once finished, I made my way to the bathroom and knelt down as instructed.

After a few minutes, Mistress Ruby emerged, wrapped in a fluffy pink towel.

"Nothing beats a shower after a hard gym session. Get in there and tidy up. Gather up my sweaty gym stuff and put it with the rest of my dirty laundry. Your next task is to put a wash on and then handwash all my delicates and socks using the woolite I've left out for you. As a reward for being a good sissy so far today, you'll sniff each pair of panties and every sock before washing them."

My whole body shuddered at the prospect of this task. As hopeless as my situation was, I couldn't deny that there was at least a part of me that was loving this. However, being just my first day, I knew it would only get tougher as my sissification progressed.

Sniffing Mistress Ruby's underwear and socks really had my cage at maximum capacity. Each sock, each gusset, and each day carried with it a slightly different scent, further adding to the torment my balls were currently experiencing.

Mistress Ruby appeared round the corner just as I was delicately scrubbing the final pair of panties.

She inspected my work, and to my relief, deemed it adequate for my first time.

"Now Evie, you've still got a lot of work to do this afternoon, but just to let you know, I've got someone coming over tonight. They can't wait to get some use out of you, so you'll be on best behaviour for me."

"Yes mistress" I said with falsified positivity.