Caught Sissified And Enslaved

Hi everyone, first time writer here so any feedback is appreciated. Over 18s ONLY.

CHAPTER 1

My name is Evan. I'm 24, 5'6, slim, and quite shy. This is the story of how I was forcibly feminised and enslaved by Mistress Ruby.

It all started during my first year of college. One day, while emptying my laundry from one of the communal washers on our campus, a pair of pink cotton panties appeared amongst the rest of my clothes, having no doubt been left behind by the previous user. In a horny panic, I hurriedly stuffed them, along with the rest of my clothes, into my laundry bag and scurried back to my room.

Having packed my clothes away, I was now left with these soft pair of pink panties, laying on my bed. For some reason, I was suddenly overcome with the urge to try them on.

With a nervous anticipation building in the pit of my stomach, I slowly stepped into the panties and slid them up my legs. Stroking my genitals over the front of the panties, I started to envisage what it would be like to live life as a girl, even just for an hour.

Fantasies of having a pair of plump breasts and a round ass flooded my mind as I stroked myself to one of the biggest orgasms of my life.

Immediately, the shame and the regret took over as I quickly peeled off the panties and buried them in the bottom of my laundry bag.

Why didn't I just leave them where I'd found them?

Why did I fantasise about being a woman?

Why can't I shift the image of those panties sliding up my legs and around my waist?

Following this episode, I continued my life at college as normal, only occasionally revisiting this new avenue of my sexuality, dabbling in forced feminisation erotic fiction from time to time.

CHAPTER 2

Fast forward three years, and with college now behind me, I was about to begin the next chapter of my life.

Besotted with the life I'd built for myself here in the city, I was desperate to find myself a flat close to the restaurant where I now worked full-time. Unfortunately, with the cost of living these days, the majority of rental opportunities involved either house sharing with a family, or another guy.

Being extremely introverted and not at all masculine, neither option seemed at all like something I'd be willing to do.

With mere days before I had to vacate my college room, I was slowly resigning myself to the fact I'd soon be on a flight back to the bores of my home life.

Then, from nowhere, a brunette named Ruby who'd recently become a waitress at the restaurant where I worked, approached me during a shift, asking about my current predicament.

Ruby was stunning. Everything about her was complete perfection, and seeing her in pantyhose and a mini skirt often made it difficult to focus on my work. We'd spoken on a handful of occasions but truth be told, I was always overcome with nerves when faced with a girl like Ruby.

Standing at 5'11, she was comfortably taller than me. This wasn't helped by the fact that she'd sometimes wear a pair of 3 inch heels, accentuating the beauty of her long legs even further.

Catching myself in a daze as she explained her own dilemma, I soon gathered that she was looking for someone to move in with her as her previous roommate had recently moved away for work.

Not wanting to pass up what seemed like the opportunity of a lifetime, I quickly agreed. Ruby explained that the room wasn't the biggest, and was currently looking a bit feminine, but I didn't care.

We arranged to move my stuff over the next day as we both had the day off work.

CHAPTER 3

Setting the final box down in my new room, it became apparent that I really didn't have all that many belongings. After thanking Ruby for helping carry my stuff up to her flat, I set about unpacking as Ruby stood in the door.

"Sorry about the pink walls" she chuckled.

"Oh not to worry. I'm just happy to have found somewhere. Thankyou again by the way for offering me the room".

"No problem at all. Glad to finally have a man about the place. I'm going to put my feet up so once you've finished unpacking, come and join me in the living room".

"Will do, shouldn't take too long to sort all this out".

As she turned to walk down the hall, I couldn't help but catch a glimpse of her beautiful ass, hugged tightly by her gym leggings. It was clear that she kept in fantastic shape, with a mesmerising blend of muscle and curves that turned my knees weak.

After just a quarter of an hour, I had most of my things unpacked, so I nervously walked through to the living room to join Ruby.

"All done?"

"Yes all finished just about. Thankyou again by the way. It really means a lot you letting me stay here".

"Honestly don't even mention it. My previous roommate was kind of a bitch anyway so it'll be nice to have someone like you around".

Someone like me? I wasn't entirely sure what that meant, but I'd find out soon enough.

Ruby then placed her hand on my knee.

"Now, I'm really sorry but tonight I'm going out with a few girls from my gym group so you'll have the place to yourself this evening".

"Oh not to worry, I'm shattered anyway so I'll probably just watch some YouTube then have an early night".

"Okay great. I'm going to jump in the shower but help yourself to whatever from the kitchen".

CHAPTER 4

After throwing together some dinner, I retreated to my new room and settled on my bed to watch some videos.

After an hour or so, Ruby knocked on my door to tell me she was off.

"Hey, I'm not sure when I'll be back but enjoy your evening. I've left a towel out in the bathroom in case you want a shower after all the hard work today".

"Okay thankyou. Have a good night Ruby".

And with that, the sound of the door closing meant I was now alone, or so I thought.

Upon finishing my video, I wandered through to the bathroom and sure enough, sat next to the sink was a fluffy pink towel.

After undressing and tossing my clothes aside, I noticed something pink and lacey poking out of the laundry basket. Curiosty got the better of me as I slowly walked towards the basket and lifted the lid.

Draped delicately over the rim were the most beautiful pair of lace trim pink panties I'd ever seen.

Having not masturbated for at least three days due to long shifts and the stress of arranging the move into Ruby's apartment, I was now feeling the effects of my abstinence.

Before I had a chance to stop myself, I grabbed the panties and brought them to my face. Having been to the gym earlier in the day, Ruby had left an especially delicious scent on her underwear.

Within mere seconds I was already close to cumming. The thought of Ruby wearing these panties all day was sending me into a complete trance.

Lost in the throes of my own pleasure, I failed to notice the bathroom door gradually creep open.

Fighting to prolong my impending orgasm, I could hold no longer. My eyes closed, and my head craned back as I prepared to explode.

"EVAN!?"

I froze.

There stood Ruby, phone in her hand, pointed directly at me.

"You little slut. I knew you were a creep, but I didn't think it'd be this easy to coax it out of you."

"I... I... I'm so sorry Ruby. I..."

"Oh save it Evan, please. You've really fucked yourself you know that right?" Ruby chuckled.

"Truth is Evan, I didn't ask you to move in with me because I wanted a roommate. I asked you to move in with me, because I require a sissy maid. When I heard that you were desperate for a place to stay, I just knew that I had to have you."

With every word, the colour drained from my face.

"And just so you're aware, this entire apartment is rigged with cameras. The footage of you invading my laundry basket, stealing my panties, and inhaling my delicious aroma is mine. Of course, it's all saved across multiple locations so don't even think for a second that you can erase that footage. Let's also not forget the video I have on my phone. The close-up of you pressing the back of my panties across your nostrils really is a killer."

Within mere seconds, my entire life had come crashing down. I was now at the complete mercy of Ruby, with absolutely no possible way of escape. Not only did she possess some extremely incriminating blackmail materal, she also had a significant physical advantage over me.

"So... Evan. Here's what's gonna happen. You will become my full time sissy maid and general slave. You will devote you're entire existence to me. You'll quit your job at the restaurant immediately, and sign over everything you own, to me. It's either that or I go to the police with this footage. And don't think it won't end up online as well. Are we clear?"

"Y... yes" I stammered, still coming to terms with what I've just gotten myself into.

"Yes what?" Ruby snapped.

"Y... yes Mistress."

"Good sissy. You're learning fast. From now on, you will refer to me only as Mistress Ruby. On top of that, you will only speak when given permission. If you're not answering a question or complying with a demand, I don't want to hear a peep from you. Do you understand?"

"Yes Mistress Ruby".

"Good. So, lets begin your training. First things first, you're sissy name shall be Evie. This will help to remind you of your new life as my sissy slave."

Next, in order to be a true sissy, you need to maintain a completely feminine appearance. Everything from your skincare to your clothing to your mannerisms will become entirely feminine. With that in mind, step into the shower."

Ruby then handed me a bottle of hair removal cream and instructed me to lather up my entire body, leaving only my eyebrows and shoulder length hair. Soon, a tingling sensation spread across my skin. Ruby ordered me to rinse off, leaving behind a smooth, hairless body.

"That's much better. Sissies must be silky smooth. From this day forward, you'll ensure you remain hairless in all the right places. I'll supply you with your first girly razor, which you'll use to keep all that unwanted hair at bay."

Next, Ruby moved closer to me, producing a pink leather collar. She proceeded to wrap it around my neck and secure it with a padlock. Clipping a leash onto the collar, I was now feeling extremely helpless.

"Turn around and face the wall sissy. And put your arms behind your back."

Two leather cuffs were then placed on my wrists and locked together with a short chain.

"Follow me".

A sharp tug on my collar pulled me swiftly behind Ruby.

I followed her into the living room where she instructed me to lay face down on the carpet.

"I've got some preparations to attend to, so you'll stay here until I'm done."

With that, she produced a second pair cuffs, attaching one to each of my ankles, again securing them with a chain. She then brought my wrists and ankles together linking both sets of cuffs with a short chain, effectively hogtieing me.

Lastly, Ruby told me to open my mouth, stuffing those same pink panties I had been sniffing passionately just 20 minutes prior into my gaping mouth. A pair of pantyhose was then wrapped tightly around my head, securing the panties in my mouth for as long as Ruby desired.

"Not a single sound from you Evie. Just remember, you did this to yourself. A typical creep" she tutted.

"I'm going to have so much fun with you. Don't go anywhere" cackled Ruby as she left me, hogtied and gagged with her sweaty panties in my mouth.

I'm not entirely sure how long I spent in that position, but by the time Ruby returned, my arms were burning with fatigue after spending so long pulled back in that hogtie pose.

Unlocking the chain linking my arms and legs, Ruby effortlessly lifted me up to my feet.

"Come with me Evie, your sissy journey is about to begin."

Walking into my room, I was greeted with a vast spread of feminine attire laying across my bed.

"This is going to be your uniform sissy Evie. Seeing as you're going to be my maid, it's only right that you spend every waking hour dressed as such. Let's get started."

Ruby then produced what looked like a small plastic penis.

"This is a chastity cage. You'll be in chastity at all times unless I decide otherwise. This will help to remind you that even when I'm not here, I control you. And as your frustration builds from not being able to masturbate, you'll grow even more submissive and desperate to please me. If you're a really good boy, maybe I'll even let you cum from time to time."

And with that, Ruby slid the plastic cage over my penis, linked it to a ring she placed behind my balls, and locked it all into place with a padlock.

Now for my uniform.

To begin, Ruby removed both sets of cuffs and then handed me a crotchless lacey red thong.

"It goes without saying really, but you'll wear panties all day, everyday from now on. Put them on, now."

The feeling of the panties sliding up my smooth, hairless legs was truly electrifying.

Next came a pair of silicone breasts.

"Men really have no idea how painful it can be to have a pair of breasts this size. You'll learn to appreciate the struggles that women deal with on a daily basis."

Ruby covered my chest as well as the back of the silicone breasts with an extra durable body adhesive and firmly pressed them into position. They really did have some weight to them.

To keep them in place, Ruby then picked up

a red bra, no doubt to match my panties. Ruby ordered me to put my arms through the straps before securing the clasp behind my back.

"Oh wow, you're shaping up nicely. I can't wait to watch this back one day", reminding me that every second of this was being recorded.

Next came a pair of white stockings and a matching lacey white garter belt.

"Roll the stockings up your legs slowly, and those seams had better be straight."

Ruby then showed me how to clip the suspenders onto the stockings.

"Excellent, you're starting to look like a true sissy already."

Ruby was clearly loving this. I have to admit that being forced to dress in lingerie by the girl of my dreams wasn't all that bad either, despite the predicament I found myself in.

Next, she handed me my maids outfit.

"I've got five of these, so you'll be wearing a clean one each day. Of course, one of your responsibilities will be all the laundry, so you'll be washing all of your sissy attire as needed."

I hate to admit it, but the maid outfit was nothing short of stunning. The silky material, complete with lace trim teased my smooth skin as Ruby pulled it down over my shoulders.

Hugging my 'breasts' perfectly, it showed a generous amount of cleavage, and ended just below my chastity cage with a white, frilly base.

"You look like such a slut Evie, my god! Any time you bend over, you'll be flashing your panties. What a naughty sissy you are."

Ruby then handed me a pair of three inch black heels, complete with ankle straps.

"Women have suffered in heels for generations. You will now learn to appreciate this. Go on. Put on your heels, and secure the straps in place."

Once my heels were strapped onto my ankles, Ruby produced two padlocks and clicked them into place.

"Unless I say otherwise, you'll be wearing heels. We'll incorporate rigourous training into your duties until you can walk elegantly. Of course, I'll increase the height of your heels as I see fit."

Now that my outfit was seemingly complete, Ruby placed me back into my cuffs and yanked me over to the vanity.

A vast array of makeup and beauty products lay before me as I resign myself to what is about to come.

"A sissy maid will also learn of the hardships that makeup inflict upon women. Without it, many women would simply by ignored by men who desire whatever dolled up bimbo type of girl they see in porn. Not to mention the cost and time it requires. Therefore, you will become an expert at applying your own makeup. You'll wear it everyday, without fail. Are we clear Sissy Evie?"

"Yes Mistress Ruby."

With that, Mistress Ruby sat me down and locked me into position at the vanity.

"I'll be applying your makeup to begin with, but I expect you to be doing it yourself pretty soon."

Mistres Ruby began with a foundation, evening out my skin tone. She then proceeded with some blusher to give my cheeks a feminine complexion. With that finished, she then applied some subtle eye shadow as well as mascara. My eyebrows were also penciled in to give them a feminine shape. Finally, Mistress Ruby applied some bright red lipstick.

"There! What a beautiful sissy you are Evie."

Mistress Ruby then sprayed some Ariana Grande perfume on my neck and down my cleavage.

"A nice girly scent for Sissy Evie."

To complete my transformation, Mistress Ruby ran a comb through my already very feminine hair before pulling it into a tight ponytail. She also painted my nails a bright red to match my lipstick.

She then unlocked my binds from the chair, and told me to stand in front of the mirror next to the wardrobe.

What stood before me was unrecognisable. I was truly a sissified, slutty looking maid, complete with very real-looking breasts and a face that could very easily pass as a woman.

"What do you think Sissy Evie?"

"I don't know what to say Mistress Ruby. I look so girly."

"That's the whole point stupid. And anyway, you think you look girly now? This is only the beginning. I mean, for starters, a true sissy strives to satisfy the male gaze. So, in between your maid duties, I'll have you on a rigourous workout schedule to really fill you out in the right areas. Not to mention how toned your legs will become, spending so much time slaving away in heels."

Speaking of heels, now came my first training session. Mistress Ruby first attached an eight inch chain to my cuffs and secured them in front of me, thus allowing me to use my arms while also offering a constant reminder that she owned me. She then attached a slightly longer chain to me ankles, ensuring that I'm only able to take short steps.

"So, Sissy Evie. You'll begin by walking down the hall and back to me."

Despite a shaky start, I just about made it to and from the bottom of the hallway. Already I could feel the burn in my legs.

"Again Sissy Evie, but this time, walk heel to toe. And make sure to stand up straight."

This certainly made it easier as I began to pick up more of a rhythm.

I repeated this for maybe ten minutes, punctuated only by Mistress Ruby's guidance.

"Right Sissy, now you've got the basic technique, I want you to continue walking up and down the hall while I get ready for bed. Remember, stand up straight, shoulders back, hips swaying, one foot in front of the other."

"Yes Mistress Ruby"

I hate to admit it, but my cock was absolutely bulging inside my cage. Something about being forced to walk in heels by a woman as powerful and beautiful as Mistress Ruby was causing me to question whether I was, as she believes, a natural sissy.

That being said, the pain in my feet and legs was becoming unbearable. The idea of being in heels almost all day everyday seemed impossible to me, but I guess I didn't realy have a choice.

Mistress Ruby returned after a short while.

"That's passable Evie. You've still got a lot to learn, but that'll do for your first bit of training. Now, follow me."

With my heels clicking on the wooden floor, I followed Mistress Ruby through to the bathroom.

"Seeing as it's getting late, I'll just have you sort the dirty laundry out before you get ready for your first night as a sissy. I want you to bring the hamper through to the kitchen and sort through everything, ready to be washed tomorrow. You'll be hand washing all my delicates tomorrow, so leave them in a separate pile. When you're done, come see me in my room."

As I carefully sorted through all of Mistress Ruby's laundry, I started to become completely entranced by the musty scent emanating from her various items. The combination of panties, socks and workout gear was absolutely electrifying, and sent shivers down my spine. It was at this moment that I really started to notice the pinch of the chastity cage as my cock pulsed inside. However, if I wanted any form of release, Mistress Ruby was going to make me earn it.