ROOM 104

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A trans sissy encounters a bully.
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CarrieQ
CarrieQ
159 Followers

It was on a whim that I agreed to meet John in his hotel room. He was a pal of Gary's, a guy twice my age with whom I'd been known to spend the evening every now and again.

The newly built hotel had a posh name and pretensions of grandeur that were woefully out of place south of the Thames. In consequence, it soon went bust. Nowadays, the whole area is being redeveloped. I only mention this because it might help some of you to figure out where it is.

Anyway, back to John..

We'd never met until I entered his hotel room, but I saw Gary most days, and that's how the meeting was set up. Gary owned a small building firm, and whenever he got paid he'd pretend he was a millionaire, which was hilariously embarrassing. Still, I wasn't the only one happy to help him live the dream while the cash was flowing.

One quiet, weekday evening, I was sat on a barstool in a particular little pub that had a discreetly eclectic clientele, nursing a small glass of wine in hopeful expectation that some nice guy might come along and offer me something bigger to swig. But the place was dead, so I was just about to drink up and go home when Gary strolled in..

He wore quite a natty suit, which he'd spoilt with a flowery black shirt and gold tie. He made a beeline for me, grinning so widely his fillings twinkled under the strip-lights like stars in a tiny, mad, crappy universe. His two-tone winkle-pickers, mismatched with bright white socks, only added to the spiv chic.

True to form, before saying a word he made a great show of dropping his money clip ostentatiously onto the counter. I said nothing, but could tell at a glance it was padded out with low denomination notes. The barman rolled his eyes, yet still looked pleased. He knew one of Gary's cash-blowing binges was about to kick off and that he'd soon be quids in. So he took his order with scrupulous politeness and wasn't disappointed. Gary bought the house a round, gave the barman a few notes and told him to keep the change. Needless to say, he was thanked profusely, but I don't think he even noticed. He had other fish to fry.

And I was the prize bream..

"I'm glad I've bumped into you," he told me, "Cos I've got a little job for you."

"Oh yeah," I replied, eyeing the money clip, "What's that, then?"

"An old mate of mine's over the road in that new hotel," he explained, "And he needs someone to go over and cheer him up. Only he's very particular -- it's gotta be someone like you."

He patted my nylon-clad thigh knowingly then, peeling three £20 notes from his clip, placed them into my lap.

"That's just an advance," he explained, "There'll be plenty more. John's a real generous guy!"

I slipped the notes hastily into my handbag. I was always short, so could do with the help. And Gary could be funny. At some point, his cash-blowing benders always ended in remorse, when he suddenly remembered he wasn't actually rich and needed the money for mundane stuff like food and his mortgage. Then he could be a right pain in the arse, so I figured it would be best if I was gone beforehand.

"Thanks," I said, "Whereabouts do I find this John?"

"He's in room 104," said Gary, already looking a little edgy. "You don't have to shoot off right away, Caz!"

"There's no time like the present," I said, and skedaddled.

A labyrinthine subway took me under a busy junction and into a little park, where stood the hotel. Strolling through the lobby in my short leopard print minidress, hearts patterned black hold-ups and animal print stiletto mules, I trembled to think what was going through the minds of the underemployed staff loitering around the reception desk.

I knew they were eyeballing me, but luckily my shoulder length platinum blonde hair hid my blushes, and though the jangle from my dangly, gold-plated earrings seemed to echo worse than the click of my stilettos, no one asked what I was up to.

Outside the door to room 104, my nerves got to me and it crossed my mind to turn around and go home. But then I remembered Gary. Once the money clip ran out, he'd want his £60 back and it would be best for me if I could prove I'd earned it. So despite an ominous foreboding, I knocked timidly on the door.

It was opened promptly by a tall, dark, stocky man wearing an ill-fitting white T-shirt and designer jeans. His muscular, hirsute arms glistened with sweat whilst a residual stubble cast a long shadow across his concave cheeks.

"Hi, I'm Carrie..." I began.

"I don't need to know your name, just get inside!" he snapped. It wasn't much of an invitation, but I stepped tentatively into the room and he immediately hung a Do Not Disturb sign on the doorknob, locked the door and hooked up the chain.

The room was typical of many a mediocre hotel. It had two single beds, a TV screwed to a work surface alongside a kettle and some crockery, a fridge, a couple of dining chairs, a small sofa and an en suite bathroom.

I followed John into the middle of the room and hung around lamely as he paced up and down. There was something vicious about him which was making me more than a little nervous, but I was trying hard not to show it.

Perhaps too hard..

John stopped in his tracks and smiled grimly. He had an unappealing glint in his eyes, like the bullies at school used to have when they'd just dreamt up some new, nasty trick to play on me. I could tell he knew I was scared of him and that my fear was acting as his aphrodisiac. I glanced fleetingly at the door, but knew it was no good. Fast as I could run, I'd never make it.

"Did Gary give you anything?" he asked.

"Yes," I said.

"How much?" he demanded.

"Sixty quid."

"He's a fucking idiot!" he cursed, "Well, all I can say is you're going to earn it, and you can start by lifting that skirt up so I can see what it is that Gary thinks it's okay to splash quite so much of MY money on!"

I began to tremble and regret not trying to run off. But there was now no chance, so I just smiled feebly and, with trembling fingers, raised the hem of my dress to reveal my stocking tops and lacy black, low-cut panties.

Smiling grimly, John placed a coarse hand on my crotch and felt the contents of my panties. He cupped my tiny cock together with my balls and squeezed the whole package so hard I screamed, spasmed and collapsed onto the carpet.

"Stupid bitch!" he snarled. "Still, as you're down there, you might as well make yourself useful!"

Saying which he dropped his jeans and boxers, revealing eight inches of thick, throbbing, uncut meat. His cherry gleamed with a fresh dollop of pre-cum, which began dripping onto the carpet like a lively stalactite.

Aligning my lips with his groin, I was struck by his simian pungency. Despite a lingering trace of cologne, I was reminded of a zoo! Still, with trembling fingers I took hold of his stiff, pulsating manhood and eased the oily tip between my lips. I blew gently, sending a warm zephyr down the pole, then began to alternately blow and suck whilst gradually inching more and more throbbing meat down my throat.

John said nothing, but his grunts told of suppressed pleasure. Placing a hand on both my shoulders, he took a firm hold of my hair and began to guide me like a marionette, leading my lips up and down the length of his quivering meat whilst at the zenith of each manly thrust, his moist, pulsating cherry tickled the back of my throat.

Struggling to breathe, I gargled loudly on his salty pre-cum until, none too soon, the trickle turned into a sporadic deluge. Tightening his grip on my hair, John tore mercilessly at the roots as he forced his throbbing ramrod down the back of my throat whilst pumping his copious load right inside me.

Having emptied every last drop from his softening barrel, John withdrew his manhood from my mouth and let loose my hair. Of course I was exhausted and fell to the floor like a rag doll, with cum dribbling from my aching lips.

"I ain't gonna pay you to laze about," he growled, "So shift your fucking arse and make me some coffee!" With which he gave me an unpleasant prod before, to my great relief, disappearing into the bathroom. I was mightily glad to see the back of him, but worried that my blowjob hadn't done much to improve his temper.

Once again, it crossed my mind to leg it. But the bathroom was next to the door, which was locked and bolted. Besides which, my legs ached so much I wasn't sure I could walk far, let alone run! So I gave up on the idea, filled the kettle and made us both a coffee.

John was only gone a few minutes, and returned with a bath towel tied carelessly around his waist.

"I said to make ME a coffee," he snarled, "I didn't say nothing about you!"

"I'm s-sorry!" I stammered.

He took his cup and sat menacingly on the edge of one of the beds.

"You're not here for afternoon fucking tea," he barked, "You're being very well paid to do what I want. Now take that dress off."

He sounded like he could very easily turn really nasty, so I hurriedly slipped out of my dress and stood before him in just my bra, panties and hold-up stockings, trembling in my pretty stiletto mules.

Casually sipping his coffee, he ogled me carelessly and appeared to have calmed down a little until, of a sudden, a spark seemed to light up his eyes and he pointed towards a dining chair.

"Bend over that," he told me.

It was a firm, upright chair with a coarse wicker seat. Tentatively, I bent over the top rail and gripped firmly onto both the aprons. My hair draped onto the seat, and I had a clear view of John closely through the weave of the wicker mesh back, even if he was upside-down.

"Get your knickers off," he ordered.

Awkwardly using just one hand, I pulled my panties down onto my thighs.

"Now spread your legs apart," he barked.

I spread my feet as wide as I could, which caused me to totter precariously on the chair. My heels were in the air with my peep-toes just about scraping the carpet. The problem was my boy-bits. They were squashed inside the top rail, with all my weight on the outside, so every movement was stretching them quite brutally.

Anxiously, I watched John as he let the towel fall casually from his waist, then rifled through the basket of complimentary condiments till he found some portions of butter. He unwrapped one and smeared it all over his manhood, which was fully recovered from its earlier exertions and was pointing eagerly at the sky.

He next approached me and rubbed another portion between my quivering butt-cheeks and around my tender rim before pushing a greasy finger up my bumhole.

Another finger followed, then a third, and I began to fear a fisting. The thought made me tremble, which caused the chair to rock precariously. John just sniggered.

"Take it easy," he said, then slid his thick, ramrod stiff cock up my bum. It hardly helped me to take it easy! He immediately began pounding away mercilessly, taking rapid thrusts that delved as far into me as could be gone.

His hips hammering constantly against my butt-cheeks was a bit too much for the chair, which wobbled so wildly that I expected us to crash in a heap on the ground. But in the meantime, the pressure was all on my boy-bits, which were being yanked and squashed with ever increasing ferocity as John's piston-like thrusts gained steadily in momentum.

But despite the remorseless ferocity of his pounding cock, he began at last to purr with something a little akin to pleasure. He suddenly let out a yell, grasped the back of my hair, then lifted me off the chair.

For an instant I was held aloft by nothing other than John's steely cock as warm cream was pumped furiously into my tender ass. We crashed back to earth and the pounding continued as he rode me hard and fast, like a wild stallion.

Not only did his thick, rock hard meat probe deep within me, it tore at my poor, aching rim till the room smelled of warm butter. And all the while, each remorseless stroke acted like a medieval rack upon my poor, battered boy-bits, sending sharp spasms through my flailing legs.

John had a copious load to discharge, but at length he fired the last of it into my slobbering bumhole, then pulled out his softening pipe, whereupon I crashed to my knees, sobbing from exhaustion. A numb tingling was all I could feel from the waist down and I wasn't sure whether I'd be able to walk anywhere anytime soon.

Not that John could have cared less..

"No slacking!" he barked, "You ain't quite finished yet."

Tearfully, I looked up to find his half flaccid manhood dangling before my eyes. I knew what was expected, so sat up and, taking it in my mouth, slowly sucked our commingled juices from it.

"That's better," he said, "Now get dressed and fuck off!"

Tearfully, I struggled to my feet, pulled up my panties and put on my dress. He remained laconic, though on the way out he grunted a few times, then handed me £40. I thought it a poor bargain, but wasn't crazy enough to argue with him.

I was in such a mad rush to get out of his room, it wasn't till I was some way down the corridor that I noticed how unsteady I was on my feet. I could only manage to stagger a few yards, then had to lean against a wall for a bit.

Stumbling through the foyer on my way out of the hotel, I once again found myself the centre of attention for those idle reception staff. This time they were quite blatantly chuckling at me and I turned crimson, guessing they must have thought I was drunk.

It wasn't till I was outside in the subway that I realized what they'd actually been laughing at. In my haste to get away from John, I'd tucked my dress into my cum-sodden panties! It was the final insult on a day of thorough humiliation, and the last time I ever did anything for Gary!

CarrieQ
CarrieQ
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