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Click hereHi all! Long time lurker first time writer. This story is a bit of a slow burn with plenty more to come.
I do want to shout out NikkiCrescent. Her Story "Slippery Slope" directly inspired this one (and was hot as fuck too!!!)
Enjoy
*********
Chapter I
I was so fucked.
I'm sure plenty of people had made worse mistakes, but at that moment, when I saw Charleston Thunder slip from first place, as horse after horse edged past him, it felt like a fuck up big enough to see from space.
The bar around me erupted in cheers and jeers as the horses blew past the finish line, every screen in the place showing slow motion replays of the champion sneaking a win at the last possible moment. I couldn't care less, my head sinking into my hands as my horse trotted across the line a full ten seconds later.
"How about that?" Jake laughed, clapping a massive hand down on my shoulder. "And you were so confident too!" He chuckled, his laugh tumbling out of him like rapids.
Jake was a big guy, a gym rat really, standing around 6 foot 3 and easily 90kg. He rocked a wild head of hair, a brilliant muddy blonde that, paired with his blessed genetics, had ladies all but frothing to speak with him. There was no denying how handsome he was, his jawline alone was aggravating.
"I thought he had it..." I said weakly, dragging my fingers down my face in agony. Being sat next to Jake, you couldn't have imagined a more different looking man than me. I've considered seeing a doctor, because it was almost as though puberty had started work on me then decided to bugger off half way through. I was short, only around 5 foot 4, skinny too, probably only around 55kg. What I lacked in mass, I made up for in beauty, or at least I told myself. I had a very boyish face, with flawless skin and brilliant green eyes. My hair was a dark brown, close to black, which I kept tidy with weekly visits to the barbers. I never had to worry about facial hair at least, let alone body hair, the only stuff that came through being of the thin wispy variety. I had my own occasional success with the ladies, but... inevitably left them disappointed when they got into my pants. It wasn't tiny... but it was small enough the shame kept me from ever getting out a ruler to check how shameful it was exactly.
"That makes it your round then right?" Jake teased, his tone telling me it was of the good-natured variety.
"Yeah yeah." I muttered, waving a hand dismissively before climbing to my feet and making my way over to the bar.
A lot of people wondered why we were friends, and, as crazy as it sounds, it just sort of happened. We were assigned to the same flat during our first year at uni and out of six other roommates we kind of just gravitated towards each other. Once we discovered our shard obsession with comics it was all over.
As I rocked up to the bar I reached for my wallet. The thing had a satisfying weight to it that became increasingly less impressive when it was opened to reveal a gallery of credit cards. I had never been financially responsible, and now that I was at uni there was no safety net. I'd managed to rack up a few thousand pounds of debt. Optimistically, I checked for cash, my search met with little more than old receipts and forgotten loyalty cards. With an internal groan, I pulled out the credit card with the lowest chance of being declined.
Tonight was supposed to be the start of a new era for me, and if that damned horse had run like it had last week I would have been debt free.
As I waited for the bartender to notice my slight frame, I felt my phone buzz in my pocket. Immediately my heart dropped, anxiety turning into full blown dread as I pulled it out and read the name of the contact. Knowing it would be worse if I didn't pick up, I swallowed hard, and answered.
"Donny! Hey, how are you doing?" I half-laughed, trying and failing to keep the fear from my voice.
"Better than you I bet." Donny said, the smirk audible in his voice. "You just lost a fair bit of money it would seem." He continued, cutting to the chase.
I tried to laugh it off, the sound catching in my throat. I swallowed again.
"Yeah, unlucky me huh." I said, pathetically.
"Unlucky?" Donny snorted. "You don't know the meaning of the word. But... If I don't have my money by the end of the week I'll be happy to show you just how 'unlucky' you can be."
My stomach dropped even further, seemingly straight through the floor.
"I... I... How much?" I whimpered.
"Five G's." Came the reply, each word a blow. I physically recoiled from my phone.
"I'm... Good for it." I lied.
"You'd better be. Anyway, I won't keep you. Enjoy your night, Tommy." His voice curling possessively around my name. Rightfully so it would seem, as without that five grand I was fucked. Little did I know, I was fucked with or without it.
*************
Wisely, I spent the rest of the night (and the rest of an overdraft) getting as drunk as humanly possible, drowning out the terror with Jake's help. It wasn't until the morning after that it clawed its way back into my brain, making itself comfy alongside the growing dread. How the fuck was I going to find five grand by the end of the week. It was already Tuesday, almost midday at that, and I hardly had two pennies to scrape together.
The behaviour ingrained by habit alone, I rolled over to my phone and started scrolling through social media. It was the same usual mess of weird politics and animal videos, punctuated occasionally by pictures of utterly gorgeous women. One in particular caught my eye, arousing my interest among other things.
She was breathtaking! Jewel, a leggy blonde in an almost translucent sundress so short you could just see the tops of her stockings below the hem. On her feet were a pair of strappy pumps, heels easily five inches high. She was prancing through a park, not a care in the world.
I clicked on her profile, unable to help myself, and discovered dozens of pictures of her travelling the world, each with her clad in revealing outfits that set my mind racing. Her face was beautiful, the perfect heart shape with a button nose and... I'm going to say it, blowjob lips. They were so full, painted pink and smouldering red. Her eyes were gorgeous too, a deep chocolate that drew me in.
I swiped through her pictures in a daze, my mind racing with all the things I would do to her. As I did, my attention snagged on one of the captions.
'Thanks to Dave, for flying me out here for some fun in the sun. I love my big spenders'
It read, the photo itself showing her perfectly manicured nails delicately curled around a glass of wine as she looked over a Sicilian sunset.
Dave? Had this bloke paid for her to come see him?
I scrolled back up to her bio and sure enough, there were two links at the top. One for her Patreon, the other for her Onlyfans.
At this point, I was no longer thinking with my head, and after rinsing through a few cards I had purchased subscriptions to both. I dove straight into her Onlyfans, unable to help myself. The first video had her kneeling, clad in emerald green lingerie, lacy stuff that struggled to keep her gorgeous breasts contained. The cameraman moved closer to her, panning down to show the lucky guy's dick. It was huge, easily eight inches. I was immediately flooded with envy. Jewel wasted no time, immediately taking it in her mouth, those gorgeous lips working up and down his shaft. From the sounds the cameraman made, he was in heaven.
My own cock was rock hard and I quickly fished it out and stroked it softly. It felt tiny in my hand, only really requiring two fingers and a thumb to really stimulate. The video continued, with the man taking hold of Jewel's head and driving his dick down her throat. She gagged slightly, but her moans were of pure ecstasy as his huge cock disappeared entirely between those stunning lips. I was sharing in their pleasure, breathing deeply as waves of it moved through me.
She continued sucking his dick for a few minutes before he reached down and grabbed a fistful of her hair, dragging her to her feet, her heels clicking on the hardwood floor. The action looked rough, but a devilish smile on her face told me that she was loving every second of it. She giggled, somehow innocently, as the camera focused on the floor, the sound of passionate kissing throbbing through my phone's speakers.
Then, abruptly, the camera spun around and Jewel was thrown down onto a bed. She laughed again as the camera appraoched, her voice angelic. It must have been a go pro or something because suddenly two hands were reaching forward to tear the underwear from her crotch. The scene was too hot, I could hardly control myself. I wanted to hold on, but my orgasm was rushing towards me. I fought it back, just long enough for the cameraman to tear her underwear away and reveal her perfect pink... Chastity cage?
It didn't matter what it was, my orgasm swept over me, more powerful than any I'd had in months. My eyes were transfixed on her cock, trapped in pink plastic and leaking fluid as the camera man began to line his own dick against her - his - tight asshole. I actually moaned, the pleasure so great that it took me several seconds to remember to breathe again. When I did, and the lightness in my head faded, it was immediately replaced with the deepest shame.
I threw my phone down in disgust. She was a guy? How did I not notice? I immediately leapt to my feet and grabbed some tissues from a nearby box and began cleaning up the jizz that now covered my abdomen. The lack of body hair made it easy to clean up, its smooth, slightly toned surface now slick.
How could she be a guy? She was so gorgeous! It didn't make any sense. My mind simply refused to comprehend what I had just watched. It couldn't. Perhaps subconsciously, I had moved away from the bed, distancing myself from the video that was still playing quietly on my phone. Had I imagined it?
With slow, fearful steps I made my way back to the bed, picking up my phone with heavy hands. It had fallen face down, and as I slowly brought it around I was once again struck by her sheer beauty and sexuality. The cameraman was lying down now, with the goddess of a woman - man! - straddling him. She bounced up and down on his cock with a practised grace that immediately turned me on again. Her heaving breasts bounced with an intoxicating rhythm and, inevitably I noticed as my eyes drifted downwards, so did her cock, locked tightly away in its cage.
I knew what chastity cages were of course. During our first year Jake and I had tried to join the Rugby team (well I tried, they had begged Jake to join), and one of the forfeits for one of the drinking games was to wear a chastity cage for a week. I had managed to avoid that nasty punishment, but Will, one of our flatmates, hadn't been so lucky. We all laughed like hyenas at the sound she made squeezing his cock into the thing.
I closed the video, shaking my head to try and dismiss the image from my mind. But it was an impossible task. I focused on getting on with the day, grabbing breakfast and a quick (cold) shower. In no time I was dressed and sat back down in my room... With nothing to distract me. I was a literature student, way behind on my assigned reading so in a fit of desperation I dug a book from my backpack and flicked to the first page.
It was futile.
By the third sentence my mind raced with visions of Jewel bouncing happily on that guy's cock. Or her lips wrapping around it, glistening as it slid in and out. With a frustrated growl I threw down the book and reached for my phone again.
*********
It was evening before I had finally exhausted myself, my bed and floor covered in used tissues. I lay a sweating mess, my mind awash with seductive visions of Jewel. I'd made my way through her entire Onlyfans catalogue, a veritable cornucopia of debauchery! She seemed to enjoy wearing lingerie, stockings and heels of all colours, and while these made up the majority of vids, they weren't the only delicacy on offer. She had plenty of content of her clad in various sexy outfits, cosplays, and even a few where she was fully dressed, sneaking in a quickie in public. It was frankly intoxicating, and it was sheer exhaustion that led me to a stopping rather than willpower.
Drained, I decided to review my second impulse purchase of the day and trawl through her Patreon. It wasn't as wantonly filthy as the Onlyfans, instead exhibiting a vast array of risque, but classy photos. In each and every one she looked like a model, each flaunting her beauty and perhaps a glimpse of her lacy underwear poking out.
I was scrolling back up to the beginning when my eyes locked on the number of patrons.
17,000!!
That was an insane amount! I flicked over to her only fans to see the number there was even higher, sitting at 19,000 subscribers. I quickly recalled the £10 I'd paid for each earlier and the numbers came together in my head. She was making £36,000 a month. Fuck... If I was making half that money I would be debt free in a week!
I would be debt free in a week.
The thought haunted me. Wriggling its way into my mind like a seed. As it burrowed deeper, it met with the sheer terror that had made its home there earlier, the two ideas mingling and coming together into a nauseating plan.
There was an abrupt thump on my door.
"Tom? Are you coming out tonight?" Jake's voice rumbled through the door.
My voice caught in my throat. Having done nothing but moan all day, words felt foreign in my mouth.
"No... I'm feeling a bit worse for wear." I called back, my mind racing.
"Oh? Want me to get you anything? Pretty sure the whole flat is heading out so you'll be here alone." He said, his voice heavy with concern.
I felt a warm surge in my chest. Jake was a good friend, if he knew how deep a hole I was in he might even offer to dig me out. But I couldn't put that on him, not when the beginnings of a plan were coming together in my mind.
"I'm good thanks dude, go have a good time." I called out.
"Okay mate, I'll try and bring a girl back for you!" He joked, his heavy footsteps receding down the hallway. I laughed falteringly at his quip, my mind busy.
******
It took me two hours to get ready. I started by taking a long shower, using my razor to clear off even the faintest trace of hair below my eyebrows. I even used Amy's body lotion. Amy was another of my flatmates, an okay looking girl that made up for it with her enthusiasm and... promiscuity. By the time I stepped out, wrapping a large towel around myself, I smelt delightful.
Next I raided Amy's room. I was only a little bit taller than her so figured her clothes might be the best fit. I was blown away when I opened her wardrobe, the thing crammed with more clothes than I could imagine. So many in fact that I was confident she wouldn't miss a few items. It took me three trips to make it back to my room, each time my arms full of clothes, costumes and shoes.
Next stop was Rachel's room. She was a drama student and, as I had hoped, her room was packed with makeup. Not really knowing what I was grabbing, I did my best to collect one of each product, bundling it into a bag. Her wardrobe provided a nice surprise too, while her clothing was much more conservative than Amy's, towards the back I found a stunning long red wig of soft curls. It joined my other treasures in my room.
Will's room was my last stop, and where I spent the longest. One thing that had stuck out to me about Jewel's videos, one thing that I couldn't shake from my mind was that damn chastity cage. It took me forty minutes of searching, and I was about to give up, when I pulled open a drawer to find the thing tucked into the bottom. It was small, smaller even than the one Jewel had, but was the same soft pink as hers. I took a second to marvel at how Will ever fit his cock in there. Maybe I wasn't the only one with... well you know.
Scurrying back to my room with my loot, I lay it all out over my bed. It was quite the haul and my stomach twisted and turned with the plans that ran through my head.
I was in no rush to copy Jewel's Onlyfans content, the mere idea of doing so made me flinch. But, if I could make a Patreon, and post similar pictures to her... I would be rich in no time! Finally, my slim build and delicate features would work in my favour.
I started by stripping naked, my now hairless body shivering in anticipation. Then I picked up the chastity cage and, after some fiddling, managed to squeeze my limp dick into the thing. It looped around my balls, the final piece snapping into place with a soft click. I looked down at the thing in awe, marvelling at how it immediately made my pelvis look more feminine. I pulled on it softly, feeling discomfort as it tugged at my genitals, that thing was locked on there tight.
Next, I lifted up a pair of lace panties I had pilfered from Amy's room. They were black, lacy, and sexy as all hell. Slowly, with quivering legs, I stepped into them. A rush ran up my smooth legs as they brushed up against them, like a buzzing current dancing upwards as I brought the underwear up and over my freshly-locked dick. The lacy fabric nestled into my ass as I positioned the waistband over my hips, causing me to gasp softly. They fit perfectly, the lace embracing what little curves I had.
Next came the bra which proved to be a tougher opponent. It matched the panties, sheer lace framing each cup. While I had taken plenty of (okay some) bras off women before, putting one on proved to be a different beast entirely. Struggling to reach the clasps behind my back, I ultimately settled on clipping it around the front and twisting it around my chest. I slipped each arm into the straps and adjusted them so that they pulled together as much of my chest as possible. Amy was pretty flat, another reason I had chosen her wardrobe to raid, and between the bra's style and padding the faintest hint of cleavage emerged. I immediately felt another rush and had to force myself to put it aside.
Next, I sat to don the dark black stockings, trimmed with floral lace patterns. If the panties had been like a static charge, these felt like an electric chair! The satin moved like fire up my legs, causing them to tingle all over. When they came to rest on my mid thigh I could feel strange stirrings in my crotch, a wild feeling of excitement held at bay by the chastity cage. After tackling the bra, the matching garter belt proved little difficulty, only taking a few minutes to fit and adjust, the silken straps a stark contrast to the pale skin of my legs.
With the underwear on, I glanced towards the full length mirror in the corner of my room. I couldn't see my reflection from where I sat and, in a snap decision, decided I wanted to be fully ready before doing so. The thought was accompanied by a fluttering of butterflies that almost made me giggle. How girly, I teased myself.
Next came Amy's top, a deep green garment of knitted fabric. I pulled it over my head, surprised at how tightly it clung to me. It wasn't until I was smoothing the hem around my waist that I noticed how low cut it was. A swooping neckline amplified the little cleavage I had, the curve of bra giving me the distinct impression of having small, but perky breasts. I gawped down at them, and they gawped back, framed by just the hint of lace from the bra beneath. The back of the top was equally low cut, a chill moving down my spine from its exposure.
Tearing my gaze away I searched for the skirt I'd picked out to match the top. It was a grey pleated thing, short enough to show my stocking tops. I stepped into it, shivering in delight and pulled it up to my waist, tucking the green top inside. The waistband was several inches thick, sitting above my hips and cinching in my waist. It was tricky to do up the zip but with a bit of effort, I managed to squeeze in.