Sharing the Sissy Style

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Chris discovers the allure of the sissy life.
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Joshana
Joshana
269 Followers

Looking out a window at the driving snow, I had no idea if walking across town back home was even going to be possible. A few hours ago the trip here had been freezing with a few flakes coming down but it had to be done for the weekly Magic night where I actually got to socialize some and show off my creativity withy janky decks. There was no card shop here in town and so this was the only chance to play and some snow and cold wasn't going to stop me.

This, however, was far more snow that I'd counted for, with the sidewalks already disappearing from my current vantage point on the second floor. Still, without a car and my usual acquaintance showing up today, it meant I had to ask for a ride from the people I'd spent the last two hours annoying and only kinda knew.

"Hey Chris, your seriously not thinking about walking home are ya?" Just then my phone lit up with a warning about a winter weather advisory, making my heart sink. I'd not checked the weather and just figured it was going to be cold and now instead there was a very good chance a blizzard was on the way. The guy who's apartment we met at had gotten stomped the whole session and disappeared after the last game, probably sulking and asking him if I could crash here didn't seem like a good idea.

Then again, talking to Izzy wasn't my idea of a great time and yet that's exactly what I was doing as the only others who showed up, a couple that always worked together and usually won, slipped out right then.

"I mean, yeah, what else can I do?" And that was the truth. Either I ask Ryan if I could crash here, assuming I could find him, or trudge 30 minutes in an honest to God blizzard.

"Come stay at my place! I live like two buildings over and you can have the couch cause I don't think it's going to get much better. Come on." Grabbing my coat, I made sure my cards were tucked away in my bag before heading outside, still not sure about this. Izzy was an oddity in that he was a pretty boy in a midwest American town that didn't seem to understand the concept. I understood it but found him mildly unnerving, in that sometimes he showed up wearing make up and looked just like a chick. And I was sure he usually wore girl's shirts and definitely jeans that showed off his legs and butt, things I didn't want to notice but always caught my eye. There was rumor of Izzy being gay but when asked he only fluttered his eyelashes and simply said wanted to know why, was the person asking interested?

And that was the person I was going to be spending time with but it beat getting lost in the snow and freezing to death. I followed his slight frame closely, the wind screaming and flinging snow that slapped and stung my face, making being outside for almost a minute a nightmare and glad for Izzy's offer as any more time outside might have been impossible.

"Holy shit!" He shouted after stepping inside his apartment on the ground floor, stomping the snow off his feet and walking into the living room. I closed and locked the door behind me, slipping my shoes off and shaking snow off my coat before hanging it up on a nearby rack. "Yeah, there's no way I'm letting you walk in that!" Shaking his head, sending jaw length dark red hair flying about, Izzy told me to make myself at home before disappearing into the bathroom, leaving me alone.

The living room smelled nice and muted light came from the open window, showing the frozen hellscape outside was becoming in short order and I stood before that, watching as car and asphalt alike were consumed by a blinding whiteness. On a little stand by the window was a small collection of potted plants but one caught my eye in particular. A vibrant red rose stood apart and I bent down, not paying the snow any mind. Inches away from it, I inhaled the slight scent and closed my eyes, wondering how it inspired feelings both aching and yet familiar, both bittersweet.

Opening my eyes, blinking to get use to the low light coming from the window, I reached out and touched the bloom, not knowing why but needing an answer for how my head was full of things I didn't want. At my touch a silky petal fell into my hand as if it wanted to be taken. Snow pelted the window as if it wanted to bury the speck of color, to hide away such beauty. The slip of the flower I held was silky, making me thing of women's things, of fancy underwear then shame but that last was fleeting as the smell seemed to invade my head, summoning up thoughts I'd hoped were long forgotten.

Without thinking about it, my head was too full of other, negative things, I brought the petal to my mouth and placed it on my tongue. I only became aware of it as the petal dissolved, something it shouldn't have done. A bitter taste invaded my mouth and then a burst of saliva, as if to purge the taste but instead I ended up swallowing it and instantly felt... Odd. Funny. Strange and weird and-

Suddenly tired I needed a place to lie down. Turning around took effort but I spotted the couch Izzy had promised me and I shuffled over, walking miles on my knees before pulling my bag off and laying it aside as I climbed atop the couch while falling within myself. The shame of being caught looking through my older sister's clothing when in middle school, of mistaking Izzy for a girl the first time I saw him and everyone from the Magic groups laughter as Izzy just blushed, dropping me a wink that no one else seemed to notice.

My eyes closed and I fell further, deeper but thankfully remembered little of that journey.

"Hey..." I heard an unfamiliar voice and mumbled something before opening my eyes, not seeing much of anything and then wondering where I was. Not in my own bed and there was someone else here, a light shining in the darkness that nearly blinded me. "Sorry!"

"Izzy?" I said, remembering snow and cold then playing cards and walking across town and my Dad asking if I was gay and me having no answer, that memory not belonging with the rest but there it was for some reason. I groaned, sitting up and finding I was sore as if during the short walk over here I'd slipped and fallen hard. "Wha-"

"Power went out. Guess they weren't kidding about it being bad out there." Holding his phone that was doing a good job at being a flashlight, Izzy looked at me then sat back on his haunches as if to gather his thoughts. "You saw the rose didn't you?"

"By the window? Yeah and..." I'd taken a petal and put it in my mouth. Why? Why had I done that? Izzy had offered me a place to stay and I'd returned the favor by eating one of his flowers? That wasn't even a dick move, it defied all reason. That was the action of someone on a bad batch of drugs.

But then another question occurred, one that was quieter but just as demanding: Why had it dissolved?

"How are ya feeling?" He asked and I shrugged, not wanting to admit I was tired, sore and hungry due to me being a guest who had eaten part of his fucking decor! And I was having some trouble waking up, on top of not being a morning person at all. "Look Chris, be honest with me and I'll do the same. How do you feel?" His voice, usually light, now had some force behind it and I knew it was time to come clean.

"Weird. Sore and hungry. I don't know why." Izzy nodded, his face seeming to float in the utter darkness of the apartment.

"Well, with no power I've got cereal. Either that or cold soup." I said nothing as he got up and walked away, my head still turning to watch him go into the kitchen even though I couldn't see his butt. Ken, the guy who had introduced me to this group of people had said they were sure Izzy wore fake boobs and Izzy wasn't shy about showing his chest but I just played the game whenever I noticed, not wanting to think about any of that.

"Here. Milk's still cold." Izzy sat two bowls, each with a spoon, on the table before me, then a galleon of milk followed by a box of Cocoa Pebbles. "Hope that's fine, it's all I got." He looked at me, the phone having been put down on the table and was now acting like a lamp.

"What did I do?" I asked and Izzy flinched back, as if I'd struck him instead of asking a question in a quiet voice.

"You... Basically took medicine not prescribed to you." Izzy nodded, as if happy with that explanation. "Eat first, I'll talk more after, kay?" Slowly, as if my arms were lagging, I put together the simple breakfast and ate just as robotically, with Izzy joining me in munching on the cereal with Fred and Barney on the packaging. Once I finished off the milk I didn't want to talk, only sleep and I leaned back, eyes not able to stay open as sleep stole me awake before Izzy could even try to explain what it was that I'd done.

Waking up the second time was easier as I blinked and looked around, recalling I was on Izzy's couch and something was up. Not wrong, maybe even weird but something had changed. It was like if I went back to my place and someone had rearranged my bookshelf. It was no big deal but once I'd noticed, it would bug me. Yet right now I hadn't noticed but knew something was up.

"Oh hey, your up. Powers still out." Izzy nearly scared me to death, carrying a scented candle and sitting beside me on the couch and putting the meager, flickering light on the table. "Sorry, it's all I got right now and I want to save my phone battery just in case."

"What happened?" I remembered the flower and snow, the cold and shame but then after that was a whole bunch of nothing. Except chocolate, that I knew.

"Well, like I said before, you took something you weren't prepared for." Izzy lounged in the corner, examining me and I felt naked, like I was back in the high school locker rooms after gym class and trying to shower as quick as possible, not wanting to be around these dumb and crude naked guys. "The thing is, I was told it'd only work on those with the desire to make it work."

"What does that mean? And it was just a flower!" I said, more to myself than him. Unless I was mistaken it was a rose and those weren't poisonous or venomous, whichever.

"A special flower meant to do one thing and it does it well." Izzy fell quiet before leaning forward. "You seeing anyone?"

"No?" I said, not following what that had to do with anything and he nodded, as if confirming something only for himself. "Why?"

"Cause then you don't have to explain things to someone else and that makes it easier. Not that this is going to be easy but let's get it over with." I wasn't quite terrified by the gibberish he was spouting off but even still I scooted away from Izzy, getting a resigned look as the candle cast flickering light in a small, uneven circle.

"It's still warm so you're safe to strip." I laughed out loud at that, more out of nervousness than his statement being funny or absurd. "Hm? No, I'm being serious, strip."

"No! Look, thanks for letting me stay here but no!" Izzy's flat expression told me I was missing something and was being stupid, it was an expression I was used to at work.

"Okay, sorry, I'm not trying to be pushy but... How about this: You take your shirt off and I'll do the same. I've seen you looking..." Izzy's face lost it's commanding edge and instead aimed a smile at me that made my heart pick up the pace. I was now shockingly, appallingly horny but something was... Off. Not wrong but there was a difference that might be cause to worry.

Without saying anything more, Izzy pulled off his hoodie and was wearing a nearly sheer shirt underneath where something was definitely happening. There was no bra on to explain away the not flat chest and I saw his nipples poking through without any effort and I swallowed hard, not able to ignore my own rising certainly that something was off with me. That shirt too was removed and Izzy hadn't been wearing fake boobs but instead was growing his own, on the border between small and just right with plenty of perk to them. My breathing was hard as Izzy gestured to me and I swallowed, glancing down as I realized there was no usual tightening of my pants, no needing to hide away a boner.

"Something different down there?" Izzy asked and I said nothing, horny but lacking the usual way of showing it. "Go ahead, check." I looked up at him, first at his smug face then down to his chest and back up.

"Chris, dude, I'm doing this for you. The sooner we figure out what happened, the sooner you'll uh, know." I felt a sudden burst of terror at that vagueness and Izzy rolled his eyes, waiting for me to do something, anything but I couldn't move. Sighing, Izzy got to his feet and looked down at me with what might have been pity but a smile quickly replaced it. "Okay, new tactic! Enjoy the show."

Raising his arms, he smiled down at me before slowly turning around, hips that flared from his slender frame swaying in a way I'd never seen before as his butt was now facing me. It was a bubble butt of the sort I only saw on women before and within arms reach. Before I knew it, the jeans were being shoved down, revealing a pair of dark blue panties that only enhanced the view, leaving me even more turned on but with a now screaming certainty about something being seriously off.

Before I could say or do anything, Izzy looked over his shoulder at me then turned around. Unable to help myself I looked at the front of his panties and didn't see what I thought I would. There was a tiny bulge and for a moment I thought that Izzy was actually a girl pretending to be a guy until the underwear was pushed down.

I saw that yes, Izzy was by definition a guy but only the dictionary would classify him as one. That little blip in his panties had been a dick but it was the smallest I'd ever seen and wasn't standing upright. No, it reminded me of a cashew, curved and small, similar in size to the actual nut.

"That's what it does." I was rendered mute, unable to make a sound if my life depended on it. "I got an offer for that flower and it makes me look like this. But I was told it only worked cause I wanted it to. That to everyone else, it was just a rose. So, did you want this?" My eyes opened wider at his words, remembering dressing up in a borrowed pair of panties and short shorts, annoyed at the bulge I couldn't quite make go away. I'd seen enough pictures of actual women and of the drawn sort to admire all they were, with that smooth glide down from the navel to an opening I'd not gotten close to being of special attention to me.

With an utter lack of social graces, I undid my jeans and shoved a hand down my pants. Instead of finding the usual eager erection, I found barely anything at all. Raising my butt of my cushions, I shoved my jeans and underwear to my knees and looked in silence at what now lay between my legs.

While it wasn't quite as small as what Izzy had, it definitely wasn't big, maybe an inch and a half and barely hard. My balls seemed to have pulled in on themselves and were mostly gone, with the hair about that area having pulled a vanishing act.

"Wha?" My hips looked wider as well, more akin to Izzy's figure and I looked up at him, finding he was smiling and smug but there was an admiration there was well. He liked what he was seeing which was only fair, seeing how he'd stripped for me.

"Huh. Either I was lied to or you wanted something like this. And I've had other people over and none of them noticed the rose." Sitting down right next to me, Izzy reached down and took my dick between two fingers, all it took now, and gave a few strokes, making me moan at the soft touch. "Cause see Chris, this is what I want to look like. Sure I could get rid of this," He touched the front of his panties while still stroking me, that feeling not quite what it used to be but still nice. "But I like the reminder being there. It's an extra special 'fuck you' to all the times I was told to 'man up' or 'be a man' about things!" Izzy practically spat the last sentence out, stopping his stroking but his pretty face took on a kinder cast, smiling at me once more.

"And now I'm wondering if you feel the same way." My heart was racing so fast there was a good chance it'd simply give out and Izzy would be left with a body on the couch instead of me. Rather than that happening I kept living, now being made to contend with things I'd rather not. There was a light fluttering in my stomach, a stutter to my thoughts that told me this was turning me on like few things did and yet, without my usual six inches, I wasn't sure how to express it.

"Oh, I think that's a yes." I moaned, not able to cover my mouth as Izzy gave another stroke and something dripped free of my diminished manhood. Then I got to watch, dumbfounded, as Izzy wiped the slight spill off my thigh and licked it from his dainty finger. "I've never got to mess around with another sissy before, have you?" I shook my head before sitting upright, that word kicking my brain into gear. After attempting to throw around a football with my Dad he'd given up after only a few minutes, tucking the ball under his arm and walking away, muttering about me being on 'some serious sissy shit.' Not even a year later he'd ask me if I was gay, then why I'd never had a girlfriend before and not buying I was seriously not good with people as an answer.

"Who said I was a sissy?!" Izzy snorted, running his hand over the minute length of my cock, making his point without speaking.

"It's not an insult Chris. It's a term for guys who've elevated cross dressing into a lifestyle and don't bother using their dinkle dongs anymore. And as you can see, mine ain't good for much of anything." I said nothing as I had nothing to say, unable to look away from the semi hard nub I now had. "Granted, there is more to it than that but I don't think it matters too much right now. I think the real question is if you want to have some fun."

There was no denying Izzy was hot, nearly naked and was similarly had trouble keeping his eyes off me. I had no real answers but was stupidly horny and my usual means to deal with it might not work and so I nodded, lost but not willing to let this chance pass me by.

Together we got my shirt off and I hissed as it was pulled off, finding my chest was puffy and sore, the beginnings of what were most certainly breasts happening. I thought back to trying on a bra and being disappointed there was nothing to fill the cups but liking it anyway. His touch, light and warm, made me gasp as he laid his hand upon my chest like he was feeling up a boob. Izzy drew close, his warmth all the more enticing in the coolness of the darkened room.

His lips found mine, soft and tasting of cherry as he gave a gentle squeeze to my tender chest. My gasp made him smile, pecking once more at my parted lips before his tongue flicked my top lip. I'd never been so turned on before but a glance down confirmed what I was feeling: What remained between my legs still wasn't in the mood to stretch out to full length.

"Takes some getting use to." Izzy whispered before kissing me once, twice more before starting to rub down there again. "Be honest and you'll get a reward: Do you like it?" His voice was sweet and I nodded, unable to lie. It was a shock but was creating this messed up circular feedback situation I wasn't sure how to remedy: My new tiny dick was making me horny but touching it wasn't getting the usual results meaning I kept looking at it trying to figure out how to get off which only made me more horny.

"There ya go, honestly is the best policy." That said, Izzy trailed his hands down my tender chest as he slipped off the couch onto his knees on the floor. My breath caught, dangerous with how little air was getting to my brain, as Izzy was in a position I'd hoped a woman would be in for the past few years. But instead of having something impressive to make her swoon and be excited for, I had something so small I'd never seen its like in any porn video I'd watched. And Izzy was close to being a chick but still had some remainder of being a guy. But that only turned me on all the more.

Joshana
Joshana
269 Followers