Working the Holidays Pt. 02

My alarm woke me at 7am with an urgent beeping.

Bleary eyed, I sat up in bed and swiped my phone screen to silence it. I clicked through the notifications, and within seconds was wide awake. A message from Kareem:

"Don't let me down today babygirl. If you don't show up today I'll have no choice but to punish you."

Disgusted, I threw the phone down on the covers. It could have been an illusion, but I swear I still had the bitter aftertaste of his hot semen in my mouth, and my jaw was aching from the oral pounding I had taken back on the shop floor. I shook my head in an attempt to clear the memories.

Kareem was playing Father Christmas in the department store. After dressing me last night as a little nympho elf, he was now forcing me to play his sexy Santa's helper. I wasn't even supposed to working today!

The phone buzzed again, and the screen lit up with a fresh message:

"And if I see my little princess wearing a single item of boys clothing the punishment will be severe."

Q

I sunk back down under the covers; I recalled his merciless spanking. How did I let myself end up in that position? Regardless of the consequences, I should never have degraded myself to that level and allowed him to blackmail me into dressing up for him. I had a choice, didn't I? Why didn't I fight back properly, or protest louder?

"Because your throat was full of cock." I murmured to myself.

Now he had so much material with which to ruin my life.

I buried my face in the pillow before quickly realising the make-up that Kareem had applied to my lips and eyes the previous evening was still on my face, and was now smeared over my bed sheets. What's more, whilst I had managed to change into a t-shirt before succumbing to sleep, I was still wearing the red lace panties and garter belt.

Hurriedly I removed them, and groped around for some pyjamas. I caught the sight of my naked ass and long slim legs in the mirror as I bent down at the waist. Kareem was right about one thing - I had such a girly ass. And my long blonde hair wasn't helping matters. I scowled, brushed it out of my eyes, and vowed to cut it.

Once dressed, I made the bed and opened my bedroom door a crack, listening for footsteps. Silence. My parents must have left for work.

First, I crept into my sisters bedroom. She had not yet returned for Christmas, and her room was empty. Ransacking her dressing table, I dug out some make-up wipes, and headed into the bathroom to wash my face. 30 seconds later I was free of mascara.

On the return to my own bedroom, I picked up the duffel bag that Kareem had given me, and emptied its contents out onto the bed. He had given me five or six fresh pairs of panties in varying styles as well as socks, hairbands, jewellery, and a big make-up bag and boxes of toiletries.

Also included was a bottle of lube, and the big black dildo. I dug it out from the pile on the bed and inspected it closely. It was firm and heavy, but soft to the touch, with detailed veining. What did he expect me to do with this? It would barely fit in my mouth, let alone anywhere else. I flung it to the floor, and the suction cup base kept it glued to the spot where it landed in the centre of my room.

I closed my eyes and clenched my fists in frustration. Kareem was expecting me to return to the store in my slutty elf outfit... I couldn't possibly do that. Not in public. The thought terrified me. But if I didn't show up he'd ruin me by posting his gallery of compromising photographs online.

"Fuck", I whispered myself. I had no choice. But I couldn't possibly wear that tiny mini-dress and those fuck-me heels in broad daylight.

Gradually, an idea began to form in my mind. What if I wore my sister's clothes? At least to get to the store, and then find a less R rated elf costume to wear, or maybe even try and buy my way out of this: offer Kareem my savings to forget this whole thing.

I found a new level of steely resolve within myself, and made up my mind to put the plan into motion. The first step was to remove the traces of my masculinity. I needed to look like a girl on the surface. I gathered the necessary equipment from the pile of beauty products in front of me, and headed back to the bathroom. I used hair removal cream over my limbs and body, removing in the hot shower the peachy fuzz that passed for my body hair. In more... private... areas, I waxed. Which was painful and awkward, but rewarding, and came without the risk of chemical irritation. I was impressed with my own handiwork.

Kareem had included hair dye in the set, and after some thought I decided to use it. The picture on the outside of the box showed a woman with a hair colour similar to my own, only a slightly lighter blonde, with a few highlights. Seeing as I was planning on cutting my hair after this, there could be no harm in using it.

Whilst the hair dye was doing it's job, I sat myself on the edge of the bathtub, and carefully painted my nails a dark red. This was much more difficult than I expected, and took me ages. Whilst I waited for the final nails to dry, I picked out a couple of pretty necklaces; a thin cute gold and beaded choker, and a bar on a chain. Very hipster chic. They highlighted my fine collar bones.

I opened Youtube on my phone, and familiarised myself with the brushes and blushes, eye shadows, pens and pencils and all the other products in front of me before opening a tutorial for a "natural" makeup look. Whatever that was. I just knew my inexperience would show through if I tried to over do it. I moved over to the bathroom mirror, and did a double take.

My hair was pink.

"Oh shit oh shit oh shit."

I washed my hair and dried it, destroying a towel in the process. My hair remained a pastel-bubblegum ultra-girly pink. I looked back at the dye packet instructions, and on the box. I had followed instructions to the letter... How had this happened?

It dawned on me. Kareem had tricked me. Again.

I stared open mouthed at my pink hair. I was clearly going to have to buy some more hair dye to turn myself back into a boy.

I refocused, and started again with the make-up. An attractive Californian Instagram model talked me through the process of moisturising, applying concealer, a light foundation and a peach blush, before I went bolder and opted for a slightly smokey eye. I contoured my nose to get the best out of it's pixie shape. It was fun, and the control I was able to exert over my appearance was at odds with the chaos my life had quickly become. Even better, I was beginning to look hot! My cheekbones stood out and my plump lips formed a sexy pout. I'm not gonna lie, it felt surprisingly great.

The next stop was my sister's room. After some consideration, I picked out some black woollen tights, a Burberry beige tartan skirt that finished above the knee, and a super-soft dark cashmere jumper that felt amazing. I also found a pair of her old Doc Martens in a drawer, and a big scarf and tight leather bike jacket. I felt these items would give me a preppy but no-nonsense look for ensuring Kareem took me seriously. I carried them into my room and laid them out on the bed.

From my supply, I chose a matching Calvin Klein soft cotton bra and panty set. The light-pink thong panties cupped my smooth cock securely, giving me a little bulge, and the high waist design accentuated my thigh-gap. But, I rationalised with myself, they're pretty similar to briefs. I stepped in front of the mirror and gave myself the once over. I pulled my hair up into a messy bun and tried a few model poses. My ass looked amazing in the thong! So pert and grope-able. The bra was sporty, and it still looked feminine even if I didn't have any tits. I stood on tip toes and slapped my ass, and pretended to moan in pleasure, giggling. All this pink was making me feel super girly. I could be such a Thot if I wanted.

"Time to get moving" I told myself, and shook my head.

I was picking up the next part of my outfit when I noticed a familiar dark shape beside me, and my focus shifted to the dildo still stuck to the floorboards. It stood firm and erect, curving slightly. The tip was bulbous, and the ridge of the head prominent. I bit my lip. My mouth seemed to be watering. Swallowing, I unstuck the cock from the floor and sat on the bed. How could something like this ever fit in someone?

I could still see myself in the mirror, a hot, willowy, pink-haired bimbo holding a thick black rod. I measured it against myself, and it reached from my crotch to my belly button. I had seen plenty of anal sex in porn online, and those girls seem to enjoy it, or at least enjoy being dominated. I couldn't help feeling curious. It would be funny to try, and besides, I had gone past the point of experimentation. I was also feeling confident with this new side to myself. I was going to get my power back from Kareem and this would be over soon.

I climbed into the centre of the bed, and squirted some lube into my fingers and on the head of the dildo. Kneeling, I rubbed the lube into the shaft, jacking it off gently as if it were a lover. I slipped off the thong and slid a couple of my slippery fingers into my ass.

One hand a continued rubbing the dildo, and with the other I slowly fingered myself, slipping in a third finger when I felt myself loosening. Feeling more relaxed, I arranged myself above the huge plastic cock and slowly pressed it against my anus. I gasped and suppressed a moan. It wasn't even in and it felt good! I lowered myself slightly, and met resistance as my hole began to stretch to accommodate the toy. This was going to be a slow process.

My own cock was standing rigid to attention inside the panties, but I resisted the urge to touch it, focusing only on the pressure on my ass. Over a period of about 15 minutes, I worked the fat dildo into me, bouncing gently and re-lubing frequently.

Then, with an almost audible pop, the head pushed past my sphincter. I gasped. Already I was so full and the pressure on my prostate was causing me to leak precum from my cli... from my dick. The next few inches slowly eased in before the dildo increased in girth. Soon I was panting and red faced as I struggled to fit any more of the dildo inside myself. It was about halfway in. Instead, I changed tack, and bounced slowly on my knees, taking as much of the length as I could. Each thrust pushed against my prostate, and within a few minutes I found myself riding it hard and moaning in a state of bliss.

I watched my reflection in the mirror in wonder; a smooth, skinny slut railing herself with a fat black dildo. Precum was leaking over my sheets. I grasped my cock and jacked off to my own image. Almost as soon as I touched myself, I was floored by my orgasm, pumping cum into my hand and crying out as the dildo rammed home.

I collapsed sideways onto the bed and the dildo flopped out of my ass. When I was finally in a condition to stand my legs were shaky and unstable.

"Fuck, the rumours are true. I guess guys do have a g-spot." I smiled to myself. "I think I'll be keeping this."

I cleaned up after myself, and hid the dildo in my wardrobe. I moved to the edge of the bed pulled the thong back up to cover my hole, which was still clenching in orgasm. I felt empty.

Got to concentrate! In a slightly dream-like state, I got dressed. I pulled on the tights and the skirt, and tucked the cashmere jumper into it. I laced up the boots, and put on the jacket, using the big scarf to disguise my flat chest.

I studied my reflection. Nailed it. I looked like I meant business; street smart but also high-maintenance. The kind of girl who is used to ordering men around. I practised speaking in a girl's voice, and after a while managed to perfect a warm, husky tone. It wasn't easy, and I had to concentrate hard, but I was fairly certain I was unrecognisable. I didn't want to take any chances. I packed a few essentials into a small shoulder bag and left the house before I could chicken out.

***

Despite the traffic, I was able to park in the usual place. It was still morning - only 11am - but the sky was dark and a cold wind was whipping leaves around. I checked my makeup in the mirror, and gave myself a little pep talk. I was to go in, queue up as a customer to see Santa. When inside the grotto I would say my piece and make my offer without the risk of any repercussions. He wouldn't be able to do anything to me in such close proximity to the public.

The department store was heaving with customers making late gift purchases. It was wonderfully decorated, with trees that glittered gold and warm with lights and baubles, and elaborate displays festooned with red and green. I headed up to the third floor, where Santa was to be found, ensuring I took small feminine steps in my doc martens. On the way I passed the place I had been trussed up and taken advantage of the previous night. Despite myself, I felt a tingling in my crotch, and found myself struggling not to tent my skirt. I turned the corner, and Santa's grotto was in front of me, with a queue that snaked for about 15metres, made up of mostly parents and children. I joined the back of it. The mothers glanced over, as if wondering why I was there. The fathers stared in lust, and I felt their eyes moved up my slim legs and over my petite young figure.

Gradually the queue moved forward, with families being allowed in one at a time for a minute with Father Christmas.

As I reached the front of the queue, I saw it was Kensie who was acting as doorman, letting visitors pass the velvet rope. I almost panicked and fled. I couldn't let her see me like this! My heart was beating loudly in my ears. I was about to leave the queue and form another plan when she looked up at me. Her gaze settled on me, but didn't light up in recognition or confusion. Hesitantly, I stepped forwards. She... She didn't recognize me! I exhaled in relief and my heart rate slowed. It also boosted my confidence to know I could deceive a friend.

"Is it just yourself here to see Santa?" She beamed at me.

"Erm.. yes please" my voice was almost a whisper.

"Great! It's nice to see you've still got the Christmas spirit. And you're just in time."

Kensie shepherded me into the entrance of the grotto before turning to the people standing beside me:

"I'm very sorry, but Father Christmas only has time for one last visitor before lunch! Please take a number and we'll see you again in 20 minutes!"

Her voice faded as a I walked into the atmospheric snow cave. The families behind me were indignant and making their displeasure known.

I nervously turned the corner and entered a dark chamber stocked high with presents and decorations. The grotto was lit with candles and Santa sat at one end.

"HO, HO, HO" rang out loudly as I drew closer. "Don't be shy now, step forward."

I steadied myself as a prepared to act tough in front of the man who had abused and blackmailed me. With clenched fists I strode forwards into the gloom.

Kareem was seated in a large green and gold throne, flanked by pine trees. A large, overflowing sack of gifts was to his left. He leaned forwards as I entered.

"I like what you've done with your hair" he said.

This threw me off.

"T-t-thanks" I stuttered. "But that's not really what I wanted to talk about"

"And your make-up is great" he continued. "Those clothes really suit you. Not what I asked for, but it's clear you're really cutting loose your slutty side in your new role. I like it a lot."

I looked down at myself. Now that he mentioned it, this skirt was very short. I bit my lip and tried to tug it down.

"Turn around" Kareem ordered. I gave him a twirl, before remembering myself.

"Kareem I can't do this anymore. I want out."

"Get down on your hands and knees girl, and show me that ass. Shake it for me."

I hesitated, and he raised his eyebrows. Quickly I complied, and feeling foolish, wiggled my butt at him.

"Lift up that skirt for me baby, and spank your ass. Say "I love you daddy, I'll do anything for you.""

"Kareem..."

"Do it"

Lacking in enthusiasm, I spanked myself. "I love you daddy, I'll do anything for you."

"Again"

"Love you daddy, I'll do anything for you."

"Like you mean it girl. I want you to say it 10 times, and slap your ass after every time you say it, and make me believe it."

Again I complied, this time with feeling. "I love you daddy, I'd do anyyyyything for you" I said, drawing out the words. I looked back over my shoulder at him and bit my finger, giving him a sultry look

"Rip those tights. I want to see that ass whilst you do it"

I did, displaying my pale white cheeks separated by the pink of my CK thong.

After 10 repeats, Kareem motioned for me to stand, and held out his hand. I took it and he pulled me into his lap. His hands were huge and firmly gripped my waist, pulling me against his fat belly. I could see smell his cologne.

"And what's your name?" Santa asked.

I remained silent.

"A pretty little thing like you must have a name. What should I call you?"

"Erica"

"Erica. That's a beautiful name. For a beautiful girl."

He patted my knee, and let his hand rest on my stockinged thigh.

"So Erica, have you been nice this year, or have you been... Naughty?"

"I've been good."

"Well well well. Let's see if that's true."

Santa reached down and picked up a large, leather bound book. He opened it on his other knee, and began flicking though the pages.

"E. E for Erica. Ahh here we are."

He turned a page, and revealed a full page photo of me bent over Kareem's desk in red lingerie, giving the camera a wicked grin.

"Why is Father Christmas so jolly?" Kareem quipped. "Because he knows where all the naughty girls live."

"Please" I begged. "I have money I can pay you. Please just delete the photos."

"Erica, I can't do that. Look at you. You need this."

I looked down at the picture in the book. God, I did look amazing. My back was arched, highlighting a narrow waist and full hips and ass. My long legs looked incredible in those heels.

"Please..." I said again, wavering.

His hand slid up my stockinged leg and beneath my skirt. He tore from edges of my ripped tights until they were just scraps around my ankles. He loosened the laces on my boots and they slipped from my feet to the floor. Now I was barefoot I could feel the fur trim on his red and white costume on my smooth legs. My feet dangled helplessly as he held me in his lap.

His hands were back, caressing me, sliding underneath the hem of my plaid skirt, rubbing at my tucked little cock and puckered pink hole with his chubby digits. I resisted the moan that was trying to escape my lips. My eyes widened when I felt his his big dick stir and harden beneath me. My heart was pounding in my chest. This was getting dangerous.

I begged weakly again, protesting and trying to push him away, but his bear-like arm pulled me close. His other hand firmly hiked up my skirt and, pushing the material of the thong aside, he slipped a finger into my ass. I gasped and squirmed.

"You're already wet for me" he chuckled. "Have you been doing some practising?"

The lube from earlier was still in my ass, giving me away! He slipped in another digit and stretched me out. I was moaning now, as his fingers assaulted my prostate.

"No! I don't want this!" I squealed.

"Quiet now" he growled, "or your friend outside might come to investigate."

I bit my lip to silence myself. I didn't want Kensie to hear. Kareem grunted, unzipped, and freed his cock from his red and white trousers, positioning me directly above it.

I panicked. This was next level, and I wasn't ready. It was all happening so fast! Kareem silenced me by invading my mouth with his tongue, his moustache bristling against my lips. He held me tight and his cock-head rested against my rosebud. Slowly, I was lowered down onto it. My hole stretched to accommodate the wide purple head of his cock, and I quietly cried out.