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Sorry for the delay, life things and all! I just wanted to say a quick thanks to everyone who read and commented on part 1! I was blown away by your kind words. Hope you enjoy!
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Chapter 2
That night I dreamt of being Paige. Not just dressed as her, but actually being her. I wore beautiful dresses and flew to far off places at the expense of my fans.
For a delicious moment I lay on a Sicilian beach, my sun-kissed skin clad in a bikini, dainty hands with manicured nails lifting a cocktail to my lips. I sighed deeply, admiring my surroundings, my eyes drifting to my right where… Jake?
He was there too, lying in the sand in nothing more than a swimming costume. His bare chest was absolutely jacked, as though carved from stone and rippled with body hair. In the dream, I felt my mouth water as I began to crawl towards him, a playful smile curling across my lips.
********
I woke up with a start, bolting upright and grasping at my chest. The dream was still fresh in my mind and for a handful of seconds I struggled to figure out where I was and why I was so flat chested. Taking in my surroundings, I began to leave the dream behind and settle into reality. The first thing I became aware of was the throbbing ache in my crotch, an exploratory hand discovering my poor dick was throbbing in the chastity cage it was trapped in. I groaned softly as the events of the night before came back to me.
I’d really done it. I’d dressed up as a woman and locked away my dick without even checking to make sure I had a way of getting it out again. The worst part was I hadn’t even needed to lock it away in the first place! Of the hundreds of pictures I took, none were revealing enough to show my panties, let alone my dick! I could have left it free and no one would have been any the wiser!
When I was finished cursing my own foolishness, I suddenly remembered the reason I had acted so stupidly in the first place. It was now Wednesday morning, only four days until I needed to pay Donny back my five grand gambling debt or god knows what he would do to me.
With a nervous desperation, I pulled myself into a sitting position and reached for my phone. My usual morning routine of scrolling through social media put to one side, I instead cautiously logged into the account I’d made the night before for Paige, my new feminine persona. I hadn’t gone too crazy, having only scheduled a dozen photos or so to upload as I slept. Once my page had loaded, my breath caught in my throat. It was one thing to take the pictures, but to see them in a public forum was another. But the thing that really sent my heart fluttering was the numbers beneath each post. They had thousands of likes and hundreds of comments!
I picked one at random, a series of pictures showing me in a long black dress that clung to my slim form, a long slit running up one side to reveal my bare leg almost up to the hip. A pair of strappy heels were wrapped around my feet, making my legs look like it went on for miles. I had switched to a darker makeup look too, heavy eye shadow framing my eyes, glancing downward demurely behind thick lashes. My lips too were a deep wine red, smooth and lustrous. I had flipped my hair over to one side, so that the deep red curls cascaded downwards, obscuring one eye, but revealing the long, smooth muscles of my neck. I had been impressed with the picture when I’d taken it, but in the cold light of day… I was IN LOVE. I looked like a dark academia version of Jessica Rabbit, oozing sex and sophistication.
With a mounting anxiety, I started reading through the comments. They were incredibly flattering, a couple from girls telling me how gorgeous I looked, gushing over my makeup and clothing, but it was the ones from the men that send my stomach into a spiral. Dozens of them, all filthy and telling me exactly what they wanted to do with me. One, from a burner account called BigDickDan, read ‘Lips like yours were just made to wrap around my cock, let me know if you are ever near London Sweetheart.’.
I had to look away, wave after wave of nerves and anxiety wracking my insides. I should have been disgusted… I was disgusted! But there was something else too. A burning, familiar feeling. The same feeling I had experienced the night before as Jake had laid his eyes on me, those hungry, hungry eyes…
I shook my head in an attempt to dismiss the thought, knowing I would undoubtedly come back to it later. Focusing on more important issues, I checked on my Patreon and my enthusiasm was immediately deflated. My social media account had managed to accrue almost 5000 followers while I’d slept, but hardly any of them had bothered to go through to my Patreon.
42 Patrons had signed up, netting me only £300.
Don’t get me wrong, the money was nice, but I had hoped for much more. What’s worse, I had failed to account for the fees that Patreon might charge, leaving me with even less than I’d expected.
A renewed dread found its way into my chest, growing with each breath. I wasn’t even 10% of the way to having the money I owed Donny and I had just wasted a full 24 hours I could have spent figuring out an actual solution to my problem. No… not wasted. I told myself, just maybe mismanaged.
I quickly went back to my social media page and searched for Jewel, the crossdressing model that had inspired me in the first place. I found her quickly, once again swept away by her feminine beauty. She was gorgeous in a way that before last night I thought utterly unattainable. But I could do it. I poured over her profile, looking for any areas in which I could improve. The day before, when I had blown through her pictures I’d neglected to read many of the comments. Now, I was amazed to see that a large number of them were from other aspiring crossdressers, asking a wide variety of questions. Jewel actually answered too! Offering advice over and over. In a separate tab, I began to make a list.
False nails, False breasts, wig glue, perfume… All things I hadn’t even considered in my first go at becoming Paige! I quickly placed an order for what I was missing, managing to score same day delivery.
Her comments were chock full of more general business advice too, ideas of how to market yourself as a brand. One thing that really stuck out to me was the idea of a ‘taster’. The basic premise was to offer a taster on your free profile, but then something people can really sink their teeth into on your premium services. It made sense, and I cursed myself for not thinking of it myself. There wasn’t much to separate the pictures on my Patreon from the ones I posted publicly. I would need to find a way to spice them up a bit, then offer a ‘taste’ to the public.
As I was putting my plan together, my phone buzzed with a private message. I had received hundreds of them on my social page overnight, but this one was from a ‘top fan’ on my Patreon. I felt a flutter run through me when a familiar username popped up at the top of the screen.
BigDickDan: Good morning beautiful, any chance you do requests? £££
I froze for a moment, as though I’d been caught out. I had to remind myself that Dan had no idea who I was. My brow furrowed as I thought of the best way to respond.
Your_Love_Paige: Maybe… It depends on the request xx
I sent back, almost throwing down my phone as if the mere act of sending the message had scalded me. I was immediately flooded with a mixture of guilt, fear, and the now recognisable smouldering in my crotch as my trapped dick tried to get hard.
BigDickDan: I would love to see under those clothes. I’ll send you £100 to see you in your underwear.
His reply came back near instantly, sending even more confusing feelings rushing through my body.
£100 wasn’t going to save me completely, but – I reasoned with myself – it certainly didn’t hurt, and if Dan was willing to pay for them, I might be able to resell them to others too. Now I just had to figure out if I was comfortable sending him pictures in just my lingerie. Posting the pics of me fully clothed had been a big step. I pushed the thought aside for now, bookmarking it under ‘ideas I’m not quite desperate enough to commit to yet’.
Instead I set about getting ready for the day. Stepping into the bathroom I went to pull my dick out to take a piss when I abruptly remembered the chastity cage. I stared at it dumbly for a few seconds before realising I was going to have to sit down to pee. I almost laughed at the absurdity of it, but my bladder was really pressing the issue, letting me know that my amusement would have to wait. I sat down, feeling a wave of feminine energy as I emptied my bladder, sans the usual thunderous sound I was used to. When I was done I even had to wipe the damn thing.
I showered after that which was its own kind of torture. Most of the time, I would knock one out in my morning shower, but with my dick locked away all I could do was stand there, tortured by the usual racy thoughts that arose. It would seem that over the course of many years, I had managed to pavlov myself into getting incredibly horny in the shower. Great.
Stepping out, I quickly got dressed and made my way to the kitchen. It was empty and I took the opportunity to ‘borrow’ a bowl of cereal from one of my house mates. I was halfway through when Jake wandered in, nearly causing me to choke on the dry grains.
“There he is! Feeling better I take it?” He said, a shit-eating grin plastered across his face.
I had no idea what to say. He had looked right at me the night before, like REALLY looked at me.
“Uh… Yeah.” I said dumbly.
“I’d say, I guess you were out for the count but I saw the gorgeous piece of ass you had in your room last night!” He smirked, closing the distance and punching me playfully on the shoulder.
I couldn’t believe it. Not only had he not recognised me, he thought I had pulled!
“Oh her?” I said slowly, scrambling for more words to flesh out the lie forming in my head, “I met her on Bumble, she came over for a bit.” I continued, trying to avoid his eyes.
“Christ my dude, you need to show me your profile at some point, you must be catfishing!” He laughed, moving over to the counter to put the kettle on.
“What do you mean by that?” I said curtly, unsure whether or not I should be offended.
Jake snorted.
“Dude… No offence… But she was so far out of your league it borders on comical.” He chuckled.
The words hit me like a bucket of water. I was immediately conflicted. On one hand, it was insulting, but on the other, he thought that dressed up I was THAT good looking.
“Just promise me you’ll let her know I’m about if she ever gets bored of you. I would love a go with her.” Jake continued, busying himself making a cup of tea as the kettle boiled.
At that moment, I thanked god that he had his back to me because I felt my cheeks go bright red. He wanted a ‘go with’ me?! I was flooded with a swirling mass of emotions. Flattered, disgusted, amused… intrigued? Unbidden, the thought of Jake ‘having a go’ with Paige waltzed into my head. They were kissing, moaning softly, and slowly undressing each other – We were slowly undressing each other. There was a familiar burning pain in my crotch as my caged dick raged against its bonds.
“I uh… Got to go.” I blurted out, climbing to my feet and rushing out the room before Jake could see how flustered I was.
“Oh? Still feeling funny?” He shouted after me.
“Something like that!” I called back, hurrying to my room.
Once inside, I slammed the door closed and leant against it, sliding down it slowly until I was sat on the floor. What was happening? Why was I having these thoughts? I wasn’t gay! I’d never even looked twice at a guy, let alone my best friend! Of course, being a young person in the modern era I’d seen my fair share of dicks on the internet, but I had always been more interested in what they were going into! Not the dicks themselves!
I’m not into men! A voice called out in my head.
But was Paige? A second, more feminine voice answered. A voice that stopped my thoughts in their tracks.
When I had dressed up as Paige the night before, I had felt like an entirely different person, so was it entirely out of the question that she might be…
No. I pushed the thought aside, locking it away in a corner of my mind alongside a growing number of other intrusive thoughts. Besides, I didn’t have the time. I had to get to work.
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I spent the rest of the day perfecting my makeup skills, voice, and mannerisms. One thing that Jewel’s profile had that mine still lacked was video. Not that I was going to post the same explicit videos as her, but I hoped maybe I could dance or something, lure in some more paying customers.
I had to interrupt my practice at one point, rushing to the door to accept my package. It flew open to reveal the delivery driver, glancing down at his clipboard.
“Delivery for- Oh sorry miss, is there a Tom Enfield here?” He said, his eyebrows shooting up when he noticed me.
“I…” I started, suddenly remembering I had a full face of makeup on. It was a soft look, with big eyelashes and heavy blush, very e-girl. “I’ll make sure he gets it.” I continued, softening my voice. With my near buzzcut I must have made a confusing figure, but the fact he had called me miss sent a fresh wave of butterflies through my stomach. I took my package quickly and darted back to my room before anyone else could see me.
Confident in my privacy, I tore into the box, pulling free my purchases: False nails, wig glue, perfume, clip-on earrings, a few choice makeup products, and a breastplate. I stared at the thing for a few moments, two giant breasts staring back at me. I hadn’t been sure quite what size to go for, picking more with my gut then my head. The end result was a pale breastplate that matched my skin tone perfectly, with two 34DD breasts bulging out of it. Slowly, as if moving through water, I reached out and touched one. They felt amazing, heavy and the exact feel of real flesh. I felt a shiver run down my spine along with a dozen other feelings and urges I did my best not to identify.
I decided then and there that I couldn’t wait until that evening. Thankfully, most of my housemates were out, probably at the very same classes I was skipping.
I showered quickly, running a razor over myself again. It was a token gesture as not even the barest hint of stubble had begun to show but it was becoming a ritual for me, the first glimpses of Paige emerging. I used Amy’s body wash again, the rush of floral scents making me light-headed. I did my best to make sure my poor dick was clean. It strained inside the cage, having been locked away for almost a whole day now. Climbing out of the shower, I didn’t even notice myself wrapping a towel around my chest rather than my waist.
Back in my room, I dropped the towel and set about my transformation. Squeezing into the chestplate was harder than I thought. The silicon was tight, so much so that for one heart-stopping moment I thought I might be stuck, but with one final effort, it settled into place, clinging to me like a second skin. I immediately moved over to the mirror and my mouth fell open. I had tits. Big ones too. I swayed slowly, marvelling at how they moved and bounced. It was remarkable how well the seams blended with my body, the tight silicon indistinguishable from my own smooth skin. Only the closest inspection revealed the seam, and I was convinced I could cover that with makeup. I was in awe at how much it changed my figure too, even with just the breastplate and chastity cage, I looked incredibly feminine.
I hurried to put on the rest of my chosen outfit, slipping into a pair of lacy white panties and sighing gently as they settled between my ass cheeks. I was excited now, raring to go, but I came across a rather obvious roadblock I really should have seen coming. All of the lingerie I had been using so far was Amy’s, and while we were a similar height, we now had vastly different chest sizes. A quick check of her bra showed she was a 32B meaning my new boobs would never fit. I swore to myself quietly, racking my brain for options.
“Rachel!” I said in an exuberant half-whisper. She was much bigger chested than Amy and while she didn’t dress anywhere near as promiscuously she might have something I could use.
Dreading the idea of having to squeeze myself back into the breastplate, I settled for simply covering myself up with an oversized t-shirt as I made my way out of the room. I was 90% sure my housemates were all out, but I still made sure to move as quickly and quietly through the house as possible. A task made all the more difficult by my new breasts. They flailed wildly as I ran from corner to corner, trying my best to avoid the windows. I found myself naturally compensated for their weight, arching my back and swinging my hips more as I hurried along.
Rachel’s door was mercifully open, signalling that she was indeed out. I slipped inside and moved quickly over to her underwear drawer. What I found shocked me. It would seem that while Rachel dressed more modestly in general, her underwear wouldn’t be out of place in the raciest porno. Silk, lace, and straps filled the drawer with astounding variety. I dug through them, being careful not to mess up the drawer anymore than I had to.
My questing fingers moved through the fabrics, until eventually my right hand came across something smooth and fleshy. Pulling it free, I came face to face with a huge dildo. Easily eight inches long, the rubber cock absolutely dwarfed my own. I swallowed hard as I looked at that thing, strangely entranced. It was incredibly realistic, with detailed veins, a hefty ballsack, and a suction cup on the base. It even smelled masculine, of salt and sweat. Without really thinking, I tucked it under one arm and continued my search. It would seem I had come across a collection of Rachel’s toys, with several more dildos, gags and buttplugs hidden beneath the layers of lace. With the same dreamlike impulse as with the dildo, I scooped up a selection and dropped them all into a purse also in the drawer.
What was I doing? I couldn’t quite say, it just felt right. It felt like what Paige would do.
After looking a little further I came across a lacy white bra. It looked about the right size so taking off the t-shirt I wrangled it on. It was balcony style and had the effect of pushing my already substantial chest together and upwards, giving me more cleavage than I bet most guys would know what to do with. Satisfied, I plucked a few more options from the draw, added them to the bag containing my new toys, and sauntered back to my room.
***********
Two hours later, I was completely transformed. I stood in front of the mirror, captivated by my own reflection.
On my feet, I wore a pair of gorgeous black leather pumps, polished to a shine with a four inch stiletto heel. They were designer, with red soles that flashed whenever I kicked up my heels. Clinging to my legs, was a pair of long thigh high socks, pure white with dark red bands around mid thigh. My skirt was even tinier than the one I wore the night before, only just about reaching my mid-thigh and exposing the smooth flesh of my thighs. When I turned around, it barely covered my ass. If I lifted my arms at all it would ride up and show a glimpse of my pert butt wrapped in lacy white panties. The skirt itself was plaid, a crosshatch pattern of black and wine red. Flared, it accentuated my waist making it look almost impossibly thin. On top, I wore a white chiffon shirt, tucked into the skirt and buttoned most of the way up. The tight fabric clung to my upper half, the buttons straining under the pressure of my heaving breasts. The bra was doing its job, and with the top three buttons undone my cleavage was captivating. I had gone for a more intense makeup look, with winged eyeliner and dark eyeshadow. My cheeks were a rosy pink, speckled with fake freckles. And my lips… my lips were a deep wine red to match my skirt and coated in a waterproof lip gloss that gave them a brilliant shine. I had even glued my wig on tight, the voluminous red curls flowing down my shoulders. On my hands, I’d also glued on a set of false nails, half an inch in length and the same deep red as my lips. Bringing the whole thing together was a pair of silver clip-on earrings and a delicate silver necklace.
ero
