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Candi's Conversion Ch. 03

Story Info
A sissy is taken shopping for the sissy essentials!
4.9k words
4.52
42.6k
27

Part 3 of the 4 part series

Updated 06/09/2023
Created 09/03/2018
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Please read Parts 1 & 2 first.

-

Candi has had a long night and tomorrow she begins her sissy life properly.

First thing? Shopping of course!

-

I hadn't slept well. I'd gone to bed horny and frustrated, and Lucy's screams of ecstasy in the other room weren't helping.

Just as I'd got to sleep, a few hours after I'd crawled into bed, a loud phone notification woke me up. Mistress had sent me her point-of-view picture of Lucy, spread eagled on her back, bound to each corner.

Her makeup and hair were absolutely destroyed with spit and tears. Humiliating words and phrases written in lipstick covered her body and face. Her exposed pussy was stretched out and dripping wet. The monster dildo Mistress still wielded in her strap-on belt was balls deep in Lucy's ass.

A look of mindless ecstasy was on Lucy's face, mouth opened wide and eyes rolled back in her head.

An ear-piercing scream erupted from their room as another message came in.

"Jealous?"

I rolled over, super horny again. How was I going to get to sleep again now?

Suddenly 'Pleasure' my butt plug began to vibrate frantically. This was too much, my cock began to harden rapidly.

"CLITTY EXCITEMENT PARAMETERS : UNACCEPTABLE

DANGER OF SQUIRTING : HIGH

PREVENTATIVE MEASURES REQUIRED?"

The phrase I was dreading erupted from the speaker built into the device.

I scrabbled for my phone.

"Please Mistress, yes I'm jealous. I wish it was me being fucked. Please don't shock me!" send.

I waited for a few seconds with baited breath.

"BZZZZT!"

A heavy shock hit my chastity device.

"SHOCK ADMINISTERED

LEVEL : GENTLE."

My dick quickly shrank once more as I let out a sob in pain.

"Next time I message you, you respond straight away."

"Set your alarm for 0530, we'll be getting up at 10. I expect you to have done your exercise, showered and shaved by the time we're up. I want you outside our door, dressed in the maid outfit I know you found on that costume rail, with a tray of breakfast ready for us. Do you understand?"

"Yes Mistress, sleep well Mistress." I sent back hurriedly before setting my alarm as instructed and tried to ignore my aching groin so I could get a few hours sleep.

-

It felt like I'd just closed my eyes when my alarm began to blare in my ear. I hit the snooze button groaning and was immediately hit with a shock through the chastity cage. It was synchronised to my phone too?

I tried to stifle my scream as I jumped out of bed and frantically tried to turn off the alarm. I guess that was the end of my lie-ins!

I decided to go for my exercise first as there wouldn't be too many people up to see me running in girls' clothes at 0530 in the morning. Today's session consisted of a 5k run, 30 minutes yoga and 30 minutes booty workout.

As I finished my last shaky hip thrust the butt plug chimed.

"EXERCISE COMPLETE.

GOOD GIRL CANDI.

CHECK PHONE FOR INSTRUCTIONS TO RECEIVE YOUR REWARD."

A notification appeared on my phone for an app called "The Sissy Suite".

"Congratulations on completing your workout for today. You must be hungry! Make yourself a breakfast of oats in water, put the bowl on the floor and kneel with it between your legs. Reward will be delivered when kneeling is detected."

Oats and water? Seriously? Well I was starving hungry after my meagre meal last night and the exercise so I dutifully complied.

As my knees hit the floor the butt plug chimed again.

"REWARD SEQUENCE - MILKING - INITIATED."

The butt plug, 'Pleasure' began to undulate in my ass. Swelling and shrinking in waves as it started to vibrate in a pulsating pattern.

My traitorous cock stiffened and I frantically tried to think of something to distract myself to avoid another shock.

"CLITTY EXCITEMENT PARAMETERS : ACCEPTABLE.

LIKELIHOOD OF SQUIRTING : HIGH.

ARE YOU READY TO SQUIRT LIKE THE ANAL WHORE YOU ARE CANDI?

RUB CLITTY TO VERIFY."

Overcome with lust and uncaring whether this was another trick I moaned as I rubbed at the cage which prevented me any kind of external sensation.

In response, the cage itself began to vibrate, just under the tip of my cock head.

"I'm cumming!" I squeaked, trying desperately to keep quiet.

Ropes of thick milky cum erupted from the open tip of the cage, squirting into my breakfast bowl.

I fell to the floor, completely breathless. I'd just cum without touching my cock at all, was that even possible? It was a strange feeling, somehow it had reduced the discomfort in my balls without diminishing my feeling of horniness at all. There was none of the vaguely disgusted feeling I got when I jerked off normally.

"GOOD GIRL CANDI. EAT UP!"

I looked down at the curdled mess in my bowl and began choking the disgusting sloppy mess down.

When I was done I returned to the spare room and my phone buzzed again.

"I hope you enjoyed breakfast Candi. Now it's time for your shower. The 'Pleasure and Pain'™ system requires a recharge. Once you begin your cleaning cycle, you will wash 'Pleasure' and return it to its charger. You have 30 minutes to use the bathroom, shower, give yourself a thorough enema and shave. If the plug is not returned to your ass within this time, 'Pain' will alert you each minute until it is. Are you ready to begin your cleaning cycle?"

So that was the pink dock beside my bed, the charger. Ok fine. I clicked the popup "Ready".

The plug hissed as it deflated, sliding easily out of my stretched ass. It felt strangely empty down there.

"30 MINUTE TIMER STARTED. HURRY CANDI!"

As quick as I could I complied with the instructions. The enema took the longest but I got everything done in what felt like good time. I was towelling off when suddenly,

"BZZZT!"

The familiar shock went through my groin. Shit! that was 30 minutes already? I dashed, dripping back to the bedroom. I grabbed the plug from the cradle and searched for some lube.

"10, 9, 8 ..." the countdown began.

No time, I sucked the plug urgently, grimacing as I tasted my ass on it, I'd have to wash it better tomorrow.

"4,3,2 ..."

I shoved the plug back in and it immediately inflated to just about as much as I could take so it was held in place. I was instructed to plug a micro-USB wire between 'Pleasure' and 'Pain' so that the cage would get a charge as well.

I finished my routine, cleaning my face, shaving and applying moisturiser and returned to find another message instructing me on how to style my French maid look. I was to wear the dress with the long white stockings and pink heels from the day before (they were the only ones we had that would fit). My hair would be up in high pigtails and adorned with a little lacy maid headpiece. The makeup was described in the attached tutorial as "Every day, smart, smoky look" but it looked heavier than you'd normally see anyone wear in public.

The girl in the tutorial had a classic Instagram baddie look and I tried my best to copy the flawless skin, heavy contour and highlight before going in with the large black-to-maroon smoky eyes, heavily lined and lashed, and matte, deep red lips.

It took almost an hour and a half to complete so I didn't have much time to clean and prepare breakfast.

I pulled the house together as best I could in my heels and readied 2 plates of fruit salad and yogurt and a cafetière of fresh coffee.

0955, I'd done it! I waited patiently outside their door for their summons.

-

"Come in Candi." Came the sleepy instruction form the bedroom.

"Good morning mistresses, I hope you both slept well?" I asked nervously, setting the tray down and curtsying.

They ignored me and kissed each other tenderly.

"You were amazing last night babe," said Lucy dreamily, "Can you imagine this bitch being able to satisfy a woman like that?" She indicated towards me.

"Morning slut!" she called to me patronisingly, "Have you posted your look to Instagram yet? We're trying to get you a decent following!"

Cringing at the thought of being exposed as a subservient maid I picked up my phone and started posing as she'd instructed me yesterday.

She watched me struggling to emulate some sort of sexy pose for a few minutes before fiddling with my wife's phone.

A pressure began to build in my groin as she played with the cage controls, causing it to constrict and hum with a light shock.

My knees began to buckle in towards each other, thrusting my torso outwards towards the bed. My eyes were watering and I looked through my long lashes pleadingly at Lucy. My lips pursed in a sulky pout as I moaned softly.

She snapped one picture and looked at it.

"There," she showed me, "do I have to hold your hand every fucking time?"

A sharp shock floored me and I lay there until she tossed me the phone to show me her post.

"#Maid to #serve! TeeHee! #Mistess is taking me out #shopping today what should we buy? #Cute and #sexy #outfits, #makeup, and #sextoys come on, give us ideas!"

"Shopping Mistress? I can't go out like this in public!" I squeaked.

Mistress scowled at Lucy.

"Way to ruin the surprise you dumb bimbo!" she growled, "Maybe I should take two humiliated slaves out with me!"

Lucy grinned.

"Sorry babe but I've got my good-girl reputation to maintain!" she teased.

Mistress frowned at her and pinched her nipple hard.

"Disobedient bitch." She snarled playfully as Lucy yelped, "Candi, bring that food over here and lick my pussy while I eat."

As we both ate they discussed their plans. Turns out that the following day they were off to Glastonbury festival for the rest of the week. Today was going to be a shopping trip to get me kitted out for my new life as a sissy slave as I'd just been using Mistress' ill-fitting cast offs up until this point.

They'd agreed on a shopping budget of £5000 which Mistress expected me to pay back throughout the week they were away, working as a sissy cam girl.

I begged and pleaded, I'd service them at home but please don't make me expose myself in public and as a sex object on the internet. Of course, my pleas were scornfully ignored.

Finally, they had me change out of my maid outfit and into a pair of black, 'Pink' branded leggings and a crop top as it would be easier for me to try things on. It didn't matter to them that it didn't match my shoes or makeup and that I looked ridiculous.

Filled with dread and apprehension we finally got into the car and headed out shopping.

-

We dropped Lucy at home to pack for the festival and carried on to our first destination. I sat in silence while Mistress explained in more detail what would be expected of me.

We'd be shopping to satisfy a variety of fantasies so I could perform for a variety of scenarios, many of which had been suggested by my perverted Instagram followers.

Our first stop was a bit more specialised than what the mall could provide. It was a fetish wear shop that specialised in feminisation. At least I wouldn't look too out of place there!

"Now Candi, Goddess Furia who runs this place is very traditional, not lenient like me! You must treat her with the upmost respect or you'll be severely punished or, worse, she might not sell to us!

This means obeying any command she or I give you immediately and absolutely no eye contact! Do you understand Candi?"

"Yes Mistress," A agreed apprehensively.

We pulled up and I got out of the car first, opening the door for mistress and offering her my hand as she got out. She ignored me as she headed towards a large warehouse door where we were greeted by a harsh looking older lady dressed in a leather pencil skirt, white shirt, sheer tights and spiked black stilettos. Her bright red hair was tied back in a harsh bun and matched her immaculate lipstick.

"Mistress Luna," Goddess Furia smiled, my Mistress had taken a dominant name without telling me? "So lovely to meet you finally. And this must be Candi."

She looked me up and down in disgust.

"Oh, you allow her to stand when greeting her betters?" Goddess Furia asked?

"I'm terribly sorry Furia darling, I'm still new to sissy training," she apologised through a smile shown through gritted teeth, her eyes shooting me daggers.

I fell to my knees quickly.

"I'm sorry Goddess Furia, It's my fault." I stammered trying to protect my mistress' reputation.

"And speaks without permission too..." she mused, holding her shoe in front of my face, "does she at least know how to greet a dominant correctly?"

I tentatively kissed her toe. She hissed sharply and a full armed slap knocked me to the floor where I had a good view of the big red lipstick print I'd left on her shoe.

"Dumb slut! These shoes are worth more than your ass could pay for in two months! Sissy's lick so they don't make a mess with their lipstick!"

She planted the foot heavily on my chest, the heel digging painfully into my nipple.

"Crystal, come and sort this mess out!" she barked.

From the warehouse emerged what could only be described as a rubber sex doll come to life. It was dressed in an enormous pink ruffled maid dress with matching pink and white Oxford platform heels. An enormous blonde bouffant was festooned with pink frilly bows and framed the most heavily made up face I'd ever seen. The skin was so flawless it looked like porcelain. High arched eyebrows and heavily rouged cheeks worked with eyes that had been redrawn to look almost anime like, to create the impression of a startled mannequin and massively overdrawn pink glossy lips completed the sex object impression.

She managed the most girlish run I'd ever seen in her ludicrous heels and dropped to her knees at her Goddess' feet, pulling out a frilly handkerchief and rubbing at the lipstick mark.

"I'm so sorry Goddess Furia, allow me to punish her!" Mistress Luna said, whipping out her phone to administer an intense and lasting shock which lasted until Crystal had finished removing the mark.

""SHOCK ADMINISTERED.

LEVEL : MODERATE.

MISDEMENOUR LOGGED : INAPPROPRIATE GREETING."

"Ooh, is that the new 'Pleasure and Pain' system?" Goddess Furia asked, waving aside the apology, "I hear it's very good. I'm especially interested in the pleasure control system."

Mistress smiled, glad that my misdemeanour was forgotten.

"Oh yes it's fantastic," she gushed, "I love how terrified of pleasure it has made her in just one day! Would you like a demonstration?"

She readied her phone and hauled me to my feet by my hair.

"Oh, that control won't be necessary, Crystal, give her an erection." she clicked her fingers.

Without hesitation, Crystal got to her feet sensuously and began to grind and gyrate against my body, her hand on my ass. She was breathing heavily, her mouth only centimetres away from mine, her breath smelled faintly of cinnamon and cum. She was a little shorter than me and her vacant eyes looked directly up into mine through her huge fake lashes.

She softly told me all of the filthy things she wanted to do to me or that we could do together. Her voice was breathy but completely high pitched and girly. In fact, the only clue that she wasn't a biological woman was her tiny caged cock that was dribbling an inordinate of precum down my leggings.

I responded, hypnotised by this incredible fuck doll, holding her ass and grinding against her, my other hand cupping her cheek and pulling her closer.

A voice screamed in my head.

"This isn't a girl! You're not gay!"

But I was too far gone in my horniness. Our lips met and we kissed deeply and passionately like our lives depended on it, uncaring of the havoc it wreaked on our lipstick.

"CLITTY EXCITEMENT PARAMETERS : UNACCEPTABLE

DANGER OF SQUIRTING : HIGH

PREVENTATIVE MEASURES REQUIRED?"

The dreaded alert sounded.

"Crystal, hold your clits together, let go and it'll be 6 hours in the chamber!"

"Clink!"

Crystal squeezed our metal cages together just as the shock hit.

I knew what to expect and groaned in pain but crystal was caught by surprised and screamed, tears streaming down her face, ruining what makeup was left unaffected by our kiss.

"Remarkable," Goddess Furia smiled, "I'll look into getting one for Crystal!"

Inspecting the poor sissy, Furia gave her a sharp slap.

"You've embarrassed me bitch," she growled, "Even this new slut has taken her pain better than you. You obviously require more training! Go and make yourself presentable, you have 10 minutes. I want you in extra tight nipple clamps, extra small clit cage, extra large butt plug, the spiky black one. GO!"

-

While Crystal was away I was stripped naked and forced to stand while the two dominant women walked around me, inspecting me like a race horse.

"You've really let her get fat darling!" Goddess Furia chided gently.

"Well I've only taken proper ownership of her recently!" Mistress Luna explained, "I have her on a strict diet and exercise regimen, it's all automated by the 'Sissy Suite' software."

"Fascinating," Goddess Furia said, looking at the phone, "I have some pieces that will integrate with this nicely!"

She clicked her fingers and a man appeared, completely naked apart from a leather dog mask which covered his whole head and a spiked collar.

"Spike, be a good puppy and bring these items to the test chamber." She instructed, showing him a list.

Obediently, spike bounded off and I was led inside to a plush room which contained a number of comfortable seats set around a rotating platform.

I was instructed to fetch the dominants champagne, strip naked then stand on the platform.

Eventually, Crystal returned looking immaculate once more and spike arrived shortly after with several bulging bags, the contents of which he laid out neatly on the expensive looking mahogany tables which ran around the edge of the room.

"Firstly, a sissy must always be in heels, along with stockings of course!" Furia instructed, indicating a pair of pastel pink ankle strap wedge heels.

I was instructed to roll on a pair of white stockings which were made from a tight fishnet material. Crystal held my hand as I stepped unsteadily into the shoes, then bent down to clip on a small padlock to secure them in place.

"Now you're not going to get anything pretty to fit over that gut, Crystal, the corset!"

Next, I was fitted with a white under bust bodice which was laced with pink ribbons. Crystal cinched me so tightly that I though I was going to pass out then clipped my stockings into the attached suspenders.

"See how that shows off her nice fat ass. Now we're going to create that hourglass figure."

Crystal fetched a set of large artificial breasts. The top was hidden by a wide choker with the word "SLUT" picked out in rhinestones. A pink bondage shelf bra lifted them up prominently and hid the edges seamlessly. Although the nipples were hidden, the top of each areola peeked conspicuously out.

"Knickers go on top of suspenders for easy access. She should be able to step in and out of them in her heels like it's second nature." She threw a pink lacy thong to the floor at my feet.

Crystal clipped my cage back to my plug, effectively giving me a tuck and I unsteadily stepped into the thong and pulled it up over the suspenders.

"Now I know she has long hair but remember, a sissy is a doll. She needs to be in an extravagant wig anytime she's to be presented. For this, shorter hair will be better but she can't be allowed to look like a man so I always recommend something short and girly like a pixie cut."

At her gesture, Crystal showed me how to net my hair and put on a huge, blonde wavy lace front wig.

They watched me as the platform rotated a few times while Goddess Furia made recommendations for other appropriate accessories we could get and a few of the different looks I could be dressed in.

"Let's talk about gags," she said finally, "I've just got something new in that will work with the 'Sissy Suite'. Crystal put this on."

12


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