Working the Holidays

I negotiated my way through the packed crowd of shoppers and wheeled the trolley towards the stockroom doors.

"It's mental out here."

Kareem glanced over and raised his eyebrows in greeting.

"Christmas rush - you know how it is."

Kareem was the security guard in the store, and had been for 25 years. He was about 6' 2 and had the physique of a rugby player gone to seed. A big belly and shoulders filled his shirts to bursting, and a thick moustache highlighted a square jaw. He was an imposing sight - certainly enough to put off any would-be shoplifters.

The store itself was massive, a stand alone department store in an exclusive part of London, the kind that turned over millions a week and employed dozens of staff in each department.

The stockroom, which is where I now headed, seemed equally vast. I was glad to be spending the rest of the day checking and updating prices and sales tags in the quiet. Currently, I was working my way through Row G8 - women's evening-wear. A whole load of dresses waiting to be tagged with their prices before they were displayed in front of house to customers.

I had been working this job during the holidays for years. It wasn't the best, but it was consistent and I could pick it up soon as I finished for the semester at university. It was money that kept me afloat in term time, and I couldn't afford to lose it. Besides, I had some good friends in the store and it was enjoyable to see the same faces every couple of months and fall back into a routine. Even Kareem and I got on, despite being almost polar opposites physically. He knew a good worker when he saw one, and we both had a dry sense of humour.

My name is Eric. I'm about 5'9 and slender, with narrow wrists and long legs that I kept toned with cycling. My long hair I kept in a bun to try to be edgy, or under a hat. I'm 20, but people frequently mistook me for being under 18. Sometimes it felt like puberty had yet to hit, but I got good compliments on my boyish features, and overall I was happy with my slight frame.

By the time the last item was priced up on Row 8, it was nearing the end of my shift. I'd been on my feet for 8 hours. I'd woken up at the crack of dawn to prep for an early opening, and whilst I wasn't tired, my mind was beginning to wander. The rush of holiday shoppers seemed far away this deep in the stockroom, and I had only been disturbed a handful of times by colleagues moving goods within the store.

I began to tidy up the area I had been working in. Shifting a box, I spotted a company Fall/Winter catalogue peeking out under the base of a clothing rack. It was open to the Christmas themed lingerie page, and a stunning, limber blonde was looking back out of the page at me. She was wearing a red lace bra and panties, a garter belt holding up long red and white striped Christmas stockings, and a cheeky smirk. She stood hands on hips in green heels, golden curls falling around her head. The image caught me off guard, and my mouth fell open. I sat on the box I'd just moved, and pulled the catalogue towards me. I flicked through the womenswear section of the catalogue like a naughty school boy, and could feel myself getting hard.

I looked around. There was no chance of being spotted this far back in the stockroom.

I moved to the end of the row and glanced towards the store doors. I would hear anyone coming in a long time before they'd be able to see me. Grabbing a pair of lace panties from a shelf I made my way back to catalogue. I took out my cock, rock hard from the excitement of doing this in a public place and wrapped the panties around the head. I sat there on the box, trousers round my ankles stroking for a few minutes. I bent back down over the catalogue and let my mind fill with the images of the playful underwear models. I kept returning to the picture of that flirtatious blonde in the catalogue, imagining the scent of her tousled hair and the thought of sliding my hands up those stockinged legs. I picked up the pace and within 30 seconds was cumming hard in the panties. The climax was intense! Fuck, must have been more worked up than I thoug...

Movement from across the room caught my eye, and in an instant my reverie was shattered. Kareem stood there at the end of the aisle, camera phone pointed straight at me!

"Shit, fuck! Kareem... What are you..." I scrambled to pull up my trousers, cum leaking down the front of them.

"I always wondered what you kids must get up to back here. Guess now I know."

"Kareem I'm sorry... This is the first time I swear. I thought I was alone. I was just..."

"Aye, you certainly thought you were. Jacking off on company time eh? What are we going to do about that?"

He stood there in silence, a dark look about him. He placed the phone back in his pocket.

"Kareem, please I'm sorry. Don't show that to head office. Don't fire me." I begged.

"I'll have to see what I can do boy, but I consider it my duty here to deal with such issues. Slacking off and such. Weed out the wheat from the chaff."

"Please!"

I moved towards him, looking to leave the aisle, but he stayed put, blocking my exit. If anything, he moved closer to me, his bulk towering above me. He looked over his belly at me, and raised my chin with his thick fingers to look me in the eye.

"Complete your shift tomorrow and then see me in my office after." He slowly turned and left.

I breathed a sigh of relief. But I had fucked up. I felt the cum soaked panties in my hand and was flooded with shame.

I stuck them in my pocket and made my way towards the exit, heading first to my locker in the staff room.

Kensie saw me enter the staff room. She must have been leaving too, a bag slung over her shoulder.

"On your way out?" She asked "What's up by the way? You're blushing more than usual."

"Ahh.. nothing. Just grabbing my stuff."

"I'll wait for you" she replied, and pulled out her phone whilst I made my way to the locker.

Changed into my regular clothes I felt better, and talking to Kensie back in the real world outside the shop made it feel like a bad dream that I had just woken up from. She was my height and a year older, and had been working at the same store since before I started. Kensie was on her way to the gym; a place she spent a lot of time. And you could tell it. She was athletic and toned, her medium length black hair often pulled up into a high bun. Her ass and legs looked incredible in the tight black jeans she always wore along with a hoody and sports jacket. I had only an inkling of her taste in men, but I had a feeling it wasn't me. According to her, guys under the age of thirty were "way too needy".

We parted ways in the car park, and I headed home for the evening. I was back with my folks for the holidays, and entered my parents house to the smell of home cooking and TV chatter from the living room. I quickly zoomed up the stairs and dumped my bag on my bed, stashing the dirty panties until I could later dispose of them.

- - -

The next shift passed slowly, as if I was in a daze. The reality of my situation hit me in mid-afternoon, and I was dreading seeing Kareem. I managed to avoid him until the store closed and the main lights were switched off. Dragging my feet I made my way up to his office, and was red from embarrassment before I'd even knocked on his door.

"Come in"

I entered and closed the door behind me.

"Thought you might not turn up boy" Kareem growled.

"Sorry I'm late Kareem"

He was sitting behind his large desk in his impossibly clean office. A parcel was sat on the table in front of him. I thought it best to remain silent.

"You should be able to keep your job" Started Kareem

"Thank you, I..."

"We'll deal with your punishment off the books" He continued. "Occasionally something like this happens. And In my experience it is best if things are just kept between the two of us." Kareem climbed to his feet and stepped around to my side of the desk.

"Youngsters like yourselves require a bit of guidance, and I'm here to give you that" said Kareem. "Open the package"

A small brown paper wrapped parcel was on the table in front of me. I tore at the edges and a matching red lace bra and panty set fell into my lap, along with some long striped over the knee socks.

"Put them on" ordered Kareem.

"Kareem, I'm not..."

"Call me Sir" Kareem said firmly.

This conversation was not happening as I had expected. I backed away, and Kareem smiled an unsettling grin.

"T- this job isn't worth that much to me Sir.... I mean Kareem. I'm not going to dress up for you just to keep it"

Kareem leaned over the desk and twisted the monitor to face me. "You've got more to loose than just a job son." Playing in high-definition was the video of he must have recorded yesterday. I was sat on cardboard box lost in pleasure. My eyes were shut but it was obviously me. You could see the exact moment I began to orgasm, my toes curling with delight, and the exact moment that feeling turned to panic and as I spotted Kareem recording me.

"How'd you like your friends and parents to see this eh lad? Now I'm going to repeat myself: Take off your clothes, fold them neatly and put on the panties. If you don't this here video is going to end up in your parents inbox and plastered over your friends social media."

I hesitated, and realised he had won.

"Fuck you"

Moving with speed that surprised me for a man of his age, Kareem moved across the room. His weight pinned me to the wall. He kept me in place with one hand, whilst the other hand tugged down my trousers until they were bunched around my ankles.

"Bad girls get punished" he said calmly. Not even out of breath. I struggled but might have well as been trying to move a mountain.

Hauling me over to the chair he sat down and pulled me across his lap, my bare ass pointing at the ceiling. I was wriggling and complaining, trying to get free, but he silenced me with a hard spank. I was stunned.

The next smack was harder and I let out a squeak. By the fifth I was crying out.

Kareem let out a belly laugh. "Go ahead, squeal all you want."

He dealt me five more firm spanks, until I had tears in my eyes. FInally, his hand rested on my pink ass cheek, and cupped it, his pudgy brown fingers dangerously close to my puckered pink hole. My eyes grew wide. "So you gonna give me any more lip, or have you had enough?"

"I'm sorry Sir, please let me go."

Kareem released me and I clutched at my belt and pants. Then he pointed to the women's clothes on the floor, and I reluctantly stepped out of my trousers, and removed my shirt. Kareem swept the hat from my head and released my longish blonde hair. I was naked before him, and felt very vulnerable.

I picked up the lace panties.

"Garter belt first" ordered Kareem. I put it on before sliding the long red and white striped socks up my legs and clipped them to the belt. They had small bows and a little bell on the back of each thigh. On went the panties and bra, which must have been an A cup.

I turned to face Kareem. He was smirking, and I could see the outline of a big cock pressing against his black jeans. He was getting off on this.

"And the little cherry on top if this perfect slut sundae:" he held out a pair of green stilettos, velvet green gloves with white fur trim, and a little elf Christmas hat. The hat was held on with clips in my shoulder length hair. The shoes had a 5 inch heel and I tottered about just putting them on. Kareem strode over and I skittered backwards, collapsing into a chair. He reached into his pocket and pulled out too small padlocks, which locked the straps of the stilettos around my ankles.

"Just so ya don't get any ideas about running away now."

He straightened up and looked lecherously at me.

"You make a much better girl than you ever did a boy. Want to see?"

He offered his hand to help me stand. I hesitated, and then took it. He threw open the office door and half carried me through it.

"Wait! I can't go out like this!" I protested.

"Don't worry, the store has been empty for hours." He said.

He stopped at the first full length mirror we came to, and gently pushed me in front of it. I had been expecting to a man crudely dressed in drag; a gawky man in women's underwear.

Instead I was confronted by long limbed girl dressed seductively in striped thigh socks and expensive lingerie. My hair was messy and ruffled and framed an androgynous face, with plump lips and a slight turned up pixie nose; features I had never noticed before. I straightened up, feeling pleasantly surprised. Turning, I checked out my ass. A red thong separated my my pert, full ass cheeks. Damn I looked good! All that cycling must have shaped my hips and legs. I looked like... Fuck!? It dawned on me. Kareem had dressed me to look like the girl in the catalogue. I ran my hands over my body, and could feel myself getting turned on. The slight bulge in the front of my panties started to grow...

I was distracted by a flash, as Kareem began taking photos of me.

"More leverage if I need it" he grunted. "So. You like the look of yourself huh?"

I frowned with concern, but turned back to the mirror, and nodded. I was lost for words. Walking over to the shelves, Kareem picked out a lipstick and mascara and moved me closer to the mirror. With surprising dexterity and skill he applied the makeup to my face. I watched myself transition from androgenous to christmas bimbo. Moving behind me he tied my hair into pigtails, like a schoolgirl might wear, and tied little red ribbons into the ends.

"Lots of guys come in here with their girlfriends and wives." Kareem said. "Picking out clothes for them to wear, things they think look sexy on their girl. Some of them are like you. Some of them would rather be shopping for themselves. They want to be the girl, you understand."

"That's not me... Sir. That's not me. I'm swear I'm not gay."

"Gay or straight has nought to do with it. Look at you. You were made to wear those clothes. That's why you were rubbing your tiny clit to the picture of the girl. You wanted to be her. You want guys to want to fuck you."

"...my clit?.."

I watched him approach me from behind. I was nearly naked, a peachy teenage girl in front of this lecherous older arab man. A slutty girl who has got herself in trouble... I thought. He ran a hand up my back and stroked my hair over my ear. I shivered. With the other he reached around and took my cock and balls in the palm of his hand. I jumped at his firm touch.

"No real man has a little clit like this."

"Hey!?!?" I struggled to move away, but he held me tight, occasionally tweaking my nipple to make me squeal as he worked my cock (or as he called it - my clit) through the panties. The mirror showed a smoking hot girl dressed in a sexy elf outfit being pleasured by much older man. I was so confused. Turned on at the sight of myself, but alarmed by the bigger alpha male using my body. Kareem was right, my tiny cock wouldn't be able to satisfy a girl.

He ran his hands up my ass and caressed my smooth stomach, before quickly pulling down my panties, roughly cupping my balls. Shocked by the touch, I pushed back and staggered, tripped by the panties round my ankles.

Kareem looked down, and chuckled "Don't worry babygirl, there's plenty of other ways to give pleasure." I tried to crawl away as he approached me from behind. He grabbed me by the waist and lifted me up. After a brief struggle he gathered both of my wrist in one hand and bound them in front of me with tinsel.

"Hmm. Festive."

He hauled me back in front of the mirror and pulled down a cable and hook from the ceiling. He pushed a button on the drop down and my arms were winched above my head, leaving me balanced on the heels.

"Had these installed to help us put up signs." Kareem pointed to the electric winch on the ceiling. "But this is a better display than I could ever have imagined."

He pulled away and I was left standing alone in front of the mirror. I was taken aback by his absence, frantically looking about the store to make sure I couldn't be seen. I began to get my bearings. Christ, I'm in trouble. My legs rubbed together as I tried to balance. The stockings felt amazing. The bells on the socks jingled slightly when I moved, and my attention was drawn back to the mirror. I marvelled at my beautiful dark green heels. I felt my nipples get hard and gently rub against the bra. Slowly, I teetered round to examine my ass. My legs were so long and slim in these socks! Damn I looked too hot. This was dangerous! I was so aroused by my reflection. As a guy, I always struggled to look attractive. Dressed as a girl I was a 10. I pouted at the mirror, trying out a sultry look. If it wasn't for my erect little dick poking up from between my legs, nobody would have guessed I was a guy!

I heard heavy footsteps, and Kareem returned holding a bottle of lube. His shirt was open now, revealing a hairy broad chest and a big belly under a white vest. He was no longer wearing pants, displaying thick thighs. The bulge in his briefs was frighteningly large. My eyes widened and I tried to back away, unsteady on the heels. Kareem laughed and took more pictures, before grasping my stiff little cock in his left hand. I felt his right slide down my back and and a thick finger probe my ass. I gasped and my sphincter tightened in response. Kareem grunted appreciatively.

"Kareem, please Sir no."

"Isn't this what you wanted?" He asked rhetorically "To see that hot girl in the catalogue lost in pleasure?"

I tugged at my bonds above me but they didn't give an inch. He began his two pronged assault: Slipping a large digit in my ass and slowly finger-fucking me, he gently jerked me using just his finger tips. Within minutes I was panting and my face flushed - the girl in the mirror biting her lip as she was fingered. I continued to fight and twist, but weakly, my resistance draining from my body. I moaned has he slipped in another finger and squealed as he curled them in my ass. My heels clattered feebly against the shopfloor as my knees gave from the pleasure. He quickened the pace.

"Kareem, please... I'm going to cum." I whispered.

"That's it baby, cum for Daddy"

"...Daddy?... fuck... fuck. I'm cumming!"

He curled his fingers in my ass and I shot my load into his hand. He milked my prostate with his fingers and I experienced the most intense orgasm of my life. I saw stars as my cum spurted into his fist in 5 or 6 bursts.

He raised the cum filled hand to my face.

"Good girls swallow." He ordered. Still in the haze of my orgasm I opened wide and he fed me my own sweet semen. I swallowed, opening my mouth to show him I had drunk the entire load, just like the obedient pornstars I had seen in videos.

"Thank you Sir." I said. He liked that, and gently spanked me. Mental clarity began to return to me, and I was flooded with shame. I decided to play his game to get out of there quickly.

He cut me loose and I collapsed. Cum was still dribbling from my clitty, and he handed me my panties back. I put them on, my rapidly shrinking package fitting snugly inside them. Thinking the ordeal was over, I began to get to my feet, and was surprised when he pushed me back down onto my ass. He loomed tall above me and released his large cock, which sprang out half erect, and getting larger every second! Not waiting for his cock to get fully hard, he pushed the growing head against my half-open red lips.

"Time to repay the favour, sweetcheeks" He grunted.

I opened my mouth to protest and he shoved his big brown cock inside, pushing to the back of my throat. I coughed and moaned but he thrusted again, and again. My back was now against a wall and my legs folded beneath me as he thrust into my mouth, filling my nose with his scent and testing my gag reflex. He used my ponytails like the reins on a horse, controlling me and pressing mercilessly into my increasingly sloppy mouth, abusing my hole and bringin tears to my eyes.