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Candi's Conversion Ch. 02

Story Info
The new sissy experiences a girl's night in.
3.9k words
4.46
58.2k
42

Part 2 of the 4 part series

Updated 06/09/2023
Created 09/03/2018
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Please read chapter 1 first.

-

We join Candi, dressed to the nines as a sissy princess, sucking on her lipgloss tube and dancing like a slut. Her wife and her friend have just walked in on her, rubbing herself to orgasm. She's in for it now...

-

"What the fuck is happening here?" My wife stammered in disbelief.

Her company, a friend named Lucy who I'd met once before fell about laughing, reached for her phone and began snapping pictures.

"I-I thought this was what you wanted!" I pleaded, "the shaving, and the tuck, and the cold, my clothes, then the playlists on the computer..."

As if that made any sense whatsoever.

"I wanted you cold, miserable, bored and humiliated, not whatever the fuck this is!" She shouted, "how did you possibly think this was what I was telling you to do?"

Now that she mentioned it, it was a pretty big stretch.

"Well it was cold and these were the only clothes I could find, and the only videos you let me watch were makeup tutorials and girly songs!" I mumbled defensively, "I thought that you were telling me you wanted me dressed up when you got home".

She stared at me.

"I thought that the cold and the fact that there was nothing you'd be interested in to watch would mean you went to bed, out of our way so we could have a girl's night."

She sighed heavily.

"I don't want to deal with this right now. Fetch us a bottle of wine, get out of that ridiculous outfit and fuck off to the spare room, I can't stand to look at you."

I lowered my head in shame and made for the door.

"Hold on," said Lucy suddenly, looking at me and grinning, "we could still have a girls night, the more the merrier!" she giggled, "besides, 'she' looks like she's already started the party without us. What's your name sweetheart?".

My wife was looking at me now with a mix of anger, disgust, amusement and sadism. "Well she was sucking that lipgloss like a lollipop. How about Lolli, or, I know Candi."

Lucy giggled looking at the small puddle between my legs "Candi Cumminz!" My wife joined her in peals of laughter at my expense, repeating the horrid bimbo name.

"Come here Candi, I want to show off my new girlfriend," said Lucy, readying her phone for a selfie.

I looked at my wife pleadingly but she sent me to comply with a sharp slap on the bum. Grudgingly, I joined Lucy who put an arm round me and a peace sign up.

"Pucker up Candi, let's show off those DSL's!" She instructed as she pouted for the camera and began snapping.

Grudgingly I make a kissing face for the camera and looked through my eyelashes like she did, hoping it would disguise me somewhat.

After what seemed like a thousand pictures she finally exclaimed "ok this one's cute, do you have an Insta? I want to tag you!"

My heart skipped a beat. Thankfully I didn't really go in for social media but she was going to post this on the internet?

"Don't worry," she said when I mumbled I didn't, "I'll set you one up".

She tapped away for a bit, her long acrylic nails clicking on the screen, before showing my wife the caption. "#GirlsNightIn with my #Bestie and our new #sissy #doll It's the first night of her new life, how should we play with her? Make sure you follow her for updates! #punishHer #suggestions #kinky".

"Perfect." said my wife, hitting post.

"While we wait, Candi, you have some clean up to do."

She motioned to the cum on the floor.

"Give me those knickers."

I complied, trying my best to cover my tucked penis with my petticoats.

"Candi," she growled ominously, "these aren't the panties I gave you to wear, let me check the mark I left on your tuck."

Oh shit! I'd completely forgotten that, I'd been rubbing between my legs, there was no way it'd still be intact!

"The marks gone Candi." she added quietly.

Slowly she began to mop up the cum ok the floor with the knickers I'd been wearing before running them up the trail of cum that ran down my thigh.

"Open up Candi." She instructed.

I complied with a moan as she pushed the cold, soaked panties deep into my mouth.

"You know I'm going to have to punish you don't you?" She asked almost gently, stroking my cheek. I nodded, tears in my eyes in anticipation.

"I almost feel bad," she mused, "almost."

Her knee slammed between my legs. Thankfully my dick was still taped back slightly protecting my balls but I still doubled over, my tears making distinct lines of mascara down my cheeks.

"Lucy, if you would..."

My eyes widened as a sharper pain hit me from behind. Lucy's knee had found my balls directly. I retched and fell to the floor, curling into a ball. My wife knelt down, her lips to my ear

"Don't worry darling, that's the last time you'll be punished like a man, you're my sissy slave now and will be treated as such. Now clean this mess up." She whispered, pushing my face into the remnants of the cum puddle I'd made so that I could lap it up with my tongue.

It was all I could do not to throw up. The intense ache in my balls, the salty, bitter taste of cold sticky cum licked of the questionably clean floor and the incessant dinging of Lucy's phone as Instagram notifications started to appear.

I knew she had a lot of followers, my wife often spoke about her social media skills with envy and obviously her last post had garnered a fair amount of attention.

"Ooh, some good ones here!" Lucy exclaimed happily.

"'Mani-pedi', well duh!"

"'Dress up show' yes!"

"'Fix that busted hair and makeup, she looks like a cartoon whore'," she laughed, "they should see her now. Nothing like a face full of cum and tears to really finish that look off!"

"'Teach her to walk in heels', good idea!"

"Oh my god! Andre wants to know if she's had a taste of BBC yet! Shall I give him a call, see if he wants to come and play?"

My wife laughed

"Can you imagine? Have you seen the size of that thing? It would kill her!"

"Maybe you're right, another time?" Asked Lucy, pouting.

"Let's go easy on her for now," my wife said, stroking my hair with mock sympathy as I licked up the last drops of cum.

This was going easy on me? I was laying on the cold floor licking up cum, dressed as a sissy princess, my balls busted and pictures of my humiliation already on the internet. I hated to think what going hard would entail!

-

As soon as I'd finished up the puddle, my wife grabbed a handful of hair and dragged me to my knees. She placed a finger on my chin and moved my face from side to side, inspecting the mess.

"Alright, lets get you cleaned up."

I climbed painfully to my feet with a groan and she shoved me in the direction of the bathroom. Once there, her and Lucy set about teaching me how to take off my makeup of and clean my face.

"As a sissy you're going to spend all your waking time fully caked so we need to make sure you know how to look after your skin."

My wife told me, then giving me instructions on which wipes to use to remove my heavy makeup, how to tone and cleanse and which creams to use where and when.

"Now get showered and wash your hair. Remember your sparkly moisturiser."

She told me as she ripped the tape off my tortured genitals. Lucy laughed as I gasped in pain.

"It's even smaller in the flesh!"

And with that they left me to my cold shower.

-

Once finished I dutifully returned to the bedroom, one towel wrapped around my body and another round my hair.

"Come in Candi, we've got a special treat for you!" Lucy called, far too sweetly.

I entered to find them both in comfortable pyjamas, grinning at me ominously.

There was a chair in the middle of the room with my camera set up on a tripod in front of it. On the bed there was a pink ruffled babydoll nightgown laid out. A pair of ankle strap heels with a pink pom-pom on the toe sat on the floor in front of it. A plethora of makeup covered my wife's vanity and, to my horror, a collection of sex toys sat on the bedside table.

"Get dressed sweetie," Lucy instructed gently, gesturing to the outfit, "we're going to give you a good pampering you lucky girl!"

I slipped on the nightgown, hating admitting to myself how much I loved the feeling of the gossamer material against my smooth skin. Stepping into the shoes that were only slightly too small for my feet, I wobbled slightly on the 3 inch heels as Lucy bent down to do up the straps.

As she stood up slowly, she sensuously ran a hand up my inner thigh, eventually stroking my cock which ached painfully as it struggled to get hard after its punishment. Maybe this wouldn't be so bad after all!

Her hand moved to a partially melted tub of ice cream that sat on the side and she suddenly moved it between my legs, submerging my cock and balls in the freezing mush. I let out a high-pitched screech at the painfully cold surprise.

She held it there as my wife held out both hands, one containing a pink butt plug, the other a matching chastity device.

"I bought these for you a while back when I was planning on keeping you as a chaste cuckold."

She told me.

"They're a special new design, very hi-tech, very expensive!"

"This one's called 'Pleasure'," she held up the butt plug.

"This one's called 'Pain'," grinning sadistically she held up the chastity device.

"Are you ready for a life of 'Pleasure and Pain' Candi?" She asked.

"Please Mistress, no." I whispered, horrified at the thought of being locked away while my ass was violated.

"Well I'll give you one last chance to prove you're a man, if you can do this one thing, you can go off to bed now and wake up tomorrow and go back to being a useless piece of shit man. Or of course you could just leave."

She smiled wickedly, knowing that would never happen, I had nothing in my own name, not even any clothes any more, I'd be homeless. I knew she'd share these pictures with my family and friends who'd disown me.

"What do I have to do Mistress?" I asked nervously.

"That's easy, you just have to show me you can get hard like a man. I'll make it extra easy for you, Lucy's going to suck your cock to help you along!"

"mmm, easy right baby?" Lucy purred, "I've seen you checking out these big dick sucking lips!"

She pouted her nude coloured, glossy lips and I groaned, my cock still in frozen agony.

"I know I have," my wife said sensuously, running a hand up Lucy's pyjama top to fondle her boobs.

I was stunned as she lent in, kissing Lucy passionately. I had no idea she was fooling around with girls too!

"You're so bad babe!" Lucy chided playfully, fixing her smudged lipstick with her free hand, "I almost dropped the ice cream!"

"But I can't even feel down there!" I squeaked.

They looked at me like I was a moron.

"That wouldn't stop a real man now would it?" My wife teased.

"By the way, you only have 20 seconds. If you can't do it, we'll turn you into our little sissy slave for life!"

"Are you ready Candi?" Asked Lucy.

I nodded nervously, what choice did I have?

Lucy wound her hips sexily as she slowly dropped to the floor. She took the ice cream away and quickly licked a drip off the tip. I couldn't believe how much smaller my frozen cock and balls had got, they were barely there at all.

"mmm, cookies and cream, my favourite!" she said before taking the entirety of my genitalia in her warm mouth.

My wife held up her phone with a countdown

20

19

18

As sensation began to return to my numb cock I let out a little moan.

17

16

15

Wait, the sensation of warmth was still growing, her mouth felt so hot!

14

13

12

I was panting now, the nerves in my cock screaming, it was burning!

11

10

9

"Better hurry up Candi!" my wife warned as Lucy continued to slurp on my tiny cock.

8

7

6

I tried to concentrate but it was too painfully intense.

4

3

2

"Please stop!" I wailed, "I can't"

1

My wife hit the button, "00:01" still on the screen.

Lucy pulled back, wiping a smudge of ice cream from the corner of her mouth.

"Wow, she couldn't even take a 20 second blowjob!" she laughed.

"I guess that answers the question 'does she still have a shred of masculinity left?'"

My wife picked up the chastity cage.

"Well, you failed Candi, are you ready for 'Pain'?"

I slumped, defeated

"Yes mistress, lock me away," I whispered in a tiny voice.

"It's for the best Candi." She said, sliding a metallic cock ring over by dick and balls, followed by a metal cage that easily fitted over my shrivelled dicklet. Finally a thicker plastic pink sleeve that looked like it contained some electronics slid over the cage and firmly clicked, locking everything into place.

"You were obviously never meant to be a man".

Lucy dunked the butt plug into the ice cream.

"Here hun, you want a taste?" she asked before shoving the plug into my mouth. I sucked it obediently.

She pulled it out suddenly with a wet, sucking pop.

"So eager!" she laughed.

"Bend over, I think you've earned a little 'Pleasure'".

I complied reluctantly, at least the plug wasn't very big!

I felt the warm, wet tip at the entrance to my virgin ass. Lucy slowly slid it into place. I winced as it got to the biggest section but it soon slipped into place eagerly.

"SYSTEM ENGAGED."

I jumped, that voice had come from the butt plug.

"SUBJECT: CANDI CUMMINZ:

LEVEL : SISSY IN TRAINING:

CALIBRATING SIZE..."

Suddenly the interior of the cage contracted, fitting snuggly over my cock. At the same time the butt plug began to inflate, stretching my ass until just before the point of pain, its size now ensuring to couldn't slip out.

"COCK SIZE : EXTRA SMALL,

SUGGESTED NOMENCLATURE : CLITTY."

The girls laughed.

"ANAL STRETCH (BEGINNER) : LARGE,

SLUT POTENTIAL : HIGH."

"Oooh she's born to be a whore!" Lucy laughed, "What else does it do apart from insult her?"

My wife tapped at her phone screen. "Lets see."

"CALIBRATING PLEASURE LEVELS..."

The butt plug began to vibrate and pulsate, slowly and gently at first but gradually increasing in intensity. A moan escaped my lips and I started to gyrate my hips involuntarily.

"PLEASURE LEVEL 1 : SET."

It increased and I began to move more along with it.

"PLEASURE LEVEL 2 : SET."

I could feel my cock trying to get hard, now it wanted to behave!

"PLEASURE LEVEL 3 : SET."

I moaned louder, squeezing my eyes shut. I could feel my constrained cock quiver, I felt like I was about to cum!

"CLITTY EXCITEMENT PARAMETERS : UNACCEPTABLE

DANGER OF SQUIRTING : HIGH

PREVENTATIVE MEASURES REQUIRED?"

Wait what?

My wife tapped her phone.

"BZZZZT!" An intense pain hit me between the legs and continued until my cock shrunk again.

"SHOCK ADMINISTERED

LEVEL : GENTLE."

That was gentle? It was worse than being kicked?

"Should we calibrate the pain levels do you think?" My wife mused to Lucy.

"No, please Mistress!" I thought frantically, "Why don't you let me serve you instead? Would you like some wine?"

"She learns fast!" she laughed, "Run along then Candi, fetch us a bottle of rosé and 2 glasses. Oh and don't forget to curtsy like a good girl!"

I did so, unsteadily and wobbled my way downstairs. Walking in these heels was made more difficult as my ass began to vibrate as they played with their new toy, demonstrating that they could control me from afar.

As I made my way back upstairs, the vibration levels began to fluctuate and I nearly fell a few times.

Back in the room, I set down the wine and curtsied again.

"BZZZT!" It felt like I'd been kicked in the groin by a horse. I collapsed, gasping wordlessly.

"SHOCK ADMINISTERED

LEVEL : MODERATE

LOG MISDEMEANOUR?"

"Oh god, I'm sorry babe! I meant to reward you!" cried Lucy, her hand over her mouth, "Here, we're going to make it up to you now."

She helped me up and into the chair as my wife laughed.

"You're such a ditzy bimbo Luce!"

Lucy stuck out her tongue.

"We've decided to give you a treat to celebrate the start of your new life. We're going to give you a face mask and give you a mani-pedi!" She told me excitedly.

I blinked, that was a treat?

"Um, thanks Mistress," I said sheepishly.

"You don't sound very grateful Candi," My wife warned, "Maybe you'd like some pain training instead?"

"No Mistress please!" I stammered, "I'm so grateful, I'm such a lucky girl to have such kind mistresses!"

Lucy grinned as she began to spread the cold green goo neatly over my face, leaving the eyes and lips free.

Once done, they both went to work on my hands and feet, one on each side. They began with filing down any hard spots on the skin and massaging cream into it. Then they filed the nails on my feet into a neater shape before painting them with a base coat. As they went to work on my hands, they explained what they were doing each step of the way so I could do it in future. They pushed back my cuticles and filed the nails before gluing on long pointed acrylic nails ready to paint, explaining to me they expected me to grow my natural nails to look like these.

Next they gave me a choice of bright colours and I selected a glittery pink to match my outfit. Lucy squealed with delight, clapping her hands and gushing about how cute and fuckable I'd look.

They painted 2 coats of the colour on then applied a top coat.

As we waited for them to dry, Lucy stated setting me up an Instagram account, explaining to me how I needed to post every day, how to pose for a selfie, what to do to get more followers etc etc.

As she did, my wife began painting the exposed areas of my face, giving me a dramatic, glittery, deep blue eye look with 2 sets of long false lashes per side and big, glossy, overdrawn pink lips.

Lucy hopped up and began adjusting the camera as my wife had me stand while she clipped the chastity device to the butt plug, pulling everything back between my legs.

They had me put my shoes back on and rewrapped the towel around my head as Lucy began to tell me how to pose.

It took hours. We must have taken 100's of photos until Lucy was satisfied. She uploaded it to my phone, quickly tapped a caption, posted it and showed me.

There I sat, in a babydoll nighty and heels, leaning forward slightly sitting with my legs together at the top but splayed from the knees dwon, hiding any evidence of a cock completely. My long, pink nails were held up to my painted lips which were open in mock surprise, as if I was trying to cover my mouth in surprise. My exaggerated eyes were open wide and stood out against the mud pack that covered the rest of my face.

The expression reminded me of nothing more than the look of fake surprise a pornstar gives in reaction to an uncovering an unreasonably large cock.

"My first night as a #sissy #slut! Thanks to my wonderful mistresses for making it so special. This is my #firstpost but I can't wait to make more every day to show off my #sexy new #looks. I'd love to hear what you all think! #Dm's and comments welcome, the more #naughty the better!"

Well, I guess that's that then. I'm officially a sissy and flaunting it to the world.

"Ahem!"

The door clicked and we both turned around. Our mouths fell open in unison. There stood Mistress in 6" black platform heels, a latex basque with suspenders holding up her black fishnet stockings. Her hair was tied up in a tight ponytail on top of her head and her makeup was harsh and dark. In her hand she held a riding crop and around her waist was the largest strapon I'd ever seen! It was black to match her outfit and must have been at least 14" long and 3" in diameter.

Lucy broke the stunned silence with a shriek of joy. I groaned, filled with dread.

"Please Mistress, I can't take that, not tonight!" I pleaded.

They looked at me, surprised.

"This isn't for you, you dumb slut!" Mistress laughed, "You think you're my only sub? This is a treat for Lucy!"

12


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