[TG] I Lost a Bet to a Guy in a Chiffon Skirt (But I make these high heels work) (Patreon)

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A drinking games takes a sexy turn when a magic bra gets thrown into the mix.

~

It was all Ralph’s fault really; mixing a shitty attitude, alcohol and the occult was bound to result in utter chaos. Then again, I’d known the guy ever since our freshman year of high school over a decade ago, I should have known I’d get caught up in his shitstorm one day. Granted, I don’t think anybody, no matter how forward thinking, could have foreseen how things actually went down. 

~

“I have an idea, let’s play truth or dare!”

I raised an eyebrow at Ralph, sitting next to me on the couch with an unopened beer in his hand.

“Aren't we a little old for those sorts of games?” I said tiredly. “Pretty sure the tried and true method for getting over your ex is whining and getting drunk.”

“We did that the last four times,” He argued, “it's getting boring.”

“Maybe you should stop getting dumped then.”

“Hey, it’s them, not me.”

“Debatable.”

Ralph smacked me on the arm and I winced; he could be such an ass sometimes. 

“Ow! Just tell me what happened this time.”

“I got her a gift as a surprise, she found out about it and dumped me.” Ralph said indignantly, “See, I did a nice thing and that ungrateful woman just threw it back in my face.”

“What was the gift?”

“A bra.” He said, looking oddly suspicious.

“Well, you’ve never had any issues actually pulling chicks, you can just give it to the next one.” I suggested.

“Isn't that considered a bit of an asshole move? Giving one girl a gift you bought for another?”

“I mean, what else are you going to do with a bra?” I shrugged, I didn't see the big deal personally, what his new chick didn't know wouldn’t hurt her. 

“Well, speaking of what to do with women’s clothes, truth of dare.” 

“You know we’re only going to pick a dare anyway.”

“Fine, dare then. I dare you to wear my ex’s high heels.”

“Whaaaaaaat?”

“Come on, not man enough?”

“To wear high heels? Fucking hell, alright.”

I skulled the rest of my drink while Ralph went and collected a bundle of clothes, a pair of red high heels sitting on top. 

“She left all of these.” He explained, “Let’s play a little game, we each get a drink, and race to finish it first, whoever loses has to put on one of the pieces of clothing until they are all gone.”

I snorted, that sounded like the sort of shit we would have done in college not as adults. What the hell, I was a good drinker and the chance to see Ralph in that skimpy outfit was too good to pass up; I’d have blackmail material for life! 

“Alright,” I cracked open another beer, “You’re on.”

We started sculling and I slammed down my beer in triumph only to see Ralph wearing a shit eating grin, empty can already crushed in his fist. 

“No fucking way.”

“Go on, heels on!”

I groaned, doing my best not to blush and I squeezed my feet into the tiny pair of strappy heels. They were at least one size too small for me and the little straps cut into my feet, but I managed. I grinned at myself and struck a pose, a little proud that I managed to do it without wobbling that much or rolling an ankle. 

“Alright, I choose the next one uh…the tube top!”

We continued to drink, taking turns sculling and squeezing ourselves into Ralph's ex’s clothes. I managed to get him into the tube top and chiffon skirt but he beat me out when it came to the panties and fishnets. I felt a little ridiculous standing there in heels, fishnets and a pair of women’s panties with nothing else on, but  Ralph didn’t look any better. We were both thoroughly sloshed by the time we got to the last item, a lacy, red bra. I did my best, but then I caught a glance at Ralph from the corner of my eye. He was sitting there, in his skirt trying to drink and the sight just made me burst into giggles. Beer stung my nose and I spluttered and Ralph slammed down his can in triumph. 

“I win!”

“Fuuuuuuck me!”

“Looking like that I just might.” He winked and I kicked him with one of my new heels. 

“Come on then, hand it over.”

Ralph threw me the bra and I awkwardly tried to put it on, how did women handle this every day? Those hooks seemed needlessly tiny and hard to hook up. But eventually I did it and one again struck a pose, causing Ralph to almost fall over in a fit of laughter. 

“Oh my God you look so weird.”

“I think I look very trendy!” I joked, “I feel…oh I…I uh…”

I blinked in surprise as a strange buzzing sensation started to spread over my whole body. All at once I was suddenly sober as it got stronger and stronger while Ralph’s brow furrowed.

“You alright, mate?”

“Yeah I just oh! M-my chest I oh fuck I can feel something growing!”

I looked down and sure enough, the empty cups of the bra were starting to fill. My chest rising up to fill them with a pair of round, bouncy breasts. This wasn't some weird hallucination either, I could feel them; their soft supple skin and sensitive nipples as they grew big enough to press against the fabric of the cups. 

“Oh no…” Ralph whispered with a knowing look. “I think I grabbed the wrong bra.”

“What do you mean?: I screeched, and I do mean screeched. My voice was high and panicked. Almost like a woman from a horror film.

My hands shot straight to my throat and found only a simple curve, no distinctive Adam’s apple bulge to be found. I felt my centre of gravity shifting as the breasts got bigger and bigger, I could feel the nipples squashing against the satin inlay of the bra and I couldn’t help but gasp a little. I’d never given a second thought to my nipples before but now it was hard not to think about them! How could two tiny nubs be so damn sensitive? 

The high heels I was wearing seemed to be getting bigger, no, my feet were getting smaller. They shrank and changed size until the heels were a perfect fit and I felt more tingling spreading all over my body.

“What’s happening? Ralph what did you do!?” I cried as hair began to spring forth from my head. 

Long and wavy with a honey blonde colour that was certainly not my usual brown. I tried to keep it out of my face but it was hard when there was just so much of it! 

“Um, that bra present had some…special things added by a witch I found online.” Ralph admitted, looking at me with wide eyes. 

“A witch? Are you fucking serious? Since when do witches even exist!?” 

I was stumbling now, it was hard enough to balance in heels normally but with my body constantly shifting it was basically impossible. I was wobbling like a newborn deer, forced to bend over as my ass started to swell and I groaned.

“Fuck this feels so weird…”

“...good?”

“A little.”

My face was turning bright red admitting it but it was hard to lie when my brain was so overwhelmed with sensation.  Ralph's eyes were shining with a mixture of shock and…was that arousal? I watched as his vision darted down slightly and I realised, to my horror, that bending over like I meant that he had a perfect view of my growing cleavage. 

“You perv!” I cried, only turning more pink with embarrassment, I sounded like a scandalised college girl!

I tried to stand up straight, but that only knocked me off balance, my arms flailed as I started to tip backwards and Ralph jumped to his feet and grabbed my hand, trying to help me but it was too late. I tipped backwards, pulling him with me and we ended up sprawled on the ground, his hands either side of my head and our hips pressed together. 

“Oh my God….I can feel your dick disappearing.”

So could I, we were both frozen in shock. I could feel the panties I was wearing growing tighter at the back as my ass continued to swell, pushing my hips up to crush against Ralph as my cock slowly melted away. In its place I felt something warm, wet and oh so sensitive. It was an indescribable feeling, to have a hole form inside me; it made me feel empty, like I wasn’t complete.

“Wow, your face…” Ralph muttered, “that thing really did make you my dream girl?”

His dream girl? What sort of weird ass stuff did Ralph get that witch to do? Who would want to be Ralph’s dream girl, with his hot body and pretty eyes and…nice cock that was currently growing hard trapped between us. I felt juices start to drip from my new pussy in anticipation, soaking through the panties as my legs finally took on a womanly shape to fill my fishnets. 

“R-Ralph…you should probably get off me.”

The words came from my mouth but even as I said them, they didn't feel like mine. I didn't want Ralph to go, I was enjoying the feeling of his warm body crushing against mine. A feeling that only intensified as he scrambled to get up and ended up accidentally putting his palm right on my breast. The sound that escaped me, it was somewhere between a gasp and a moan, but the ecstasy in it was obvious. 

“Oh fuck.” he whimpered, “That was so hot.”

He was rock hard against me in an instant and I didn’t care anymore; I reached up and slammed my lips against his. He groaned and I swallowed the noise up, something about the change had made me so horny I didn't even care if I was about to fuck my best friend. The fact that he found me so attractive was actually a massive turn on. 

Just like that, all hesitance was gone from us both. Ralph started to tear off the tube top and skirt with hands trembling with excitement. The panties were so soaked they were easy to pull aside, I didn't want to take the fishnets off, I loved how my new long legs looked in them. In fact, I held one up straight in the air while Ralph was stripping off and admired them. The little black stitches seemed to accentuate the natural curve of my legs and led the eye down between them where the money was. I couldn’t understand why women would want to wear anything else!

A hand wound its way around my ankle as Ralph fell to his knees beside me, he kissed my leg, then again and again slowly working his way down until he was so close to my pussy I could feel his hot breath moving over my folds. I let out a desperate whine.

“This teasing is too much, I can’t take it just fuck me already!”

Ralph didn't say anything, I think he was past the point of foreplay. He climbed up my body as I pulled the panties aside and slipped inside me in one smooth thirst. 

“Ohhhh!”

“Fuck, you’re perfect, like you were made for me.”

Ralph didn't hold back, this was no gentle lovemaking session; this was raw, animalistic fucking. And I loved it! Feeling him thrust inside me and stretching out my walls gave me a pleasure I couldn’t ever fully describe. It was primal and I clung to Ralph desperate for more. I wrapped those long legs around his waist and pulled him into me harder with each thrust, feeling him press against something deep inside my pussy that made me see stars. 

My vagina was burning with need, each thrust felt better than the last but still wasn’t enough. I arched my back as the ecstasy grew until finally, my whole body went rigid and pure pleasure filled my every pore. With a groan I came, hard, and felt myself squeezing around Ralph’s cock.

“Fuck oh fuck oh fuuuuuuuuck.”

He pulled out just in time to cum all over my leg, I felt the hot seed spilling across my skin and it sent a shiver up my spine. Ralphs collapsed against me, slipping a hand into my bra to play with my nipples and chuckling when I wriggled from the over stimulation. 

“Best drinking game ever…” He mumbled against my skin. 

I tried to be mad, but honestly, I was just biding my time till I could get him hard and do that again. 

~

I couldn't resist the Panic at the Disco reference, it just suited the idea too well.