Sharing the Sissy Style

"Ah, finally getting it huh? And that's why Bad Teddy's here but I'm going to be a selfish bitch and go first. But your going to need this." Reaching in the pack, Izzy pulled out a smaller dildo, maybe four inches and handed it over. The lube joined it in my hands and he tossed the condom in the nearby trash before pulling out another bottle of lube and working on himself.

"Here, I'll get it in and you can work it while I get my fuck on." Laying me back down, he reslicked between my cheeks and held up three fingers, then two and finally one as something massive and cold pushed against my butt. I wanted to call it off and as I sucked in air to do so my ass took in the fake phallus. I exhaled in a grunt as the cold, unfeeling thing rushed in but the discomfort was overruled by being filled. It was a lot, too much but as Izzy took one of my hands and put it between my legs to hold the thing now in me, I finally took another breath, then another. The shock faded but the dildo stayed in place, doing what it was made for very, very well.

"Got it?" I nodded and Izzy shuffled back towards Bad Teddy, laying it on it's back and lubing them both up. "Once your good, go fuck yourself, kay?" Grinning at his joke, Izzy swung a leg over Bad Teddy and faced me, reaching down to the black dick I could only see in the darkness due to it being slick and reflecting the light from my phone. By touch alone he situated Bad Teddy to where he wanted it to be, dripping freely onto the bed and bear alike. I had to contend with the overriding sensation of my own ass being filled while watching Izzy lower himself onto the biggest dick in the room. And that shiny blackness started to disappear between his legs.

I was entranced and managed to find a new plane of turned on as Izzy slid down the penis, his sissy clit hanging there forgotten as his head rolled back and he paused, hands on thighs as he moaned. Taking hold of the base, I began to work the dildo into me, a shockingly loud moan coming from my lips but I didn't stop. Running his hands up those smooth and alluring thighs, Izzy did the same for his hips and then up his front, to breasts he lifted, trying to smile but his face was too taken with passion to play coy.

Then, eyes closing and back arching, making his breasts appear larger in his hands, Izzy sat completely on Bad Teddy and the slick darkness was full gone. I gave another moan, picking up the pace with my dildo, convinced I was watching the greatest show on Earth and enjoying it all the more in this new way. Rolling his hips, Izzy gave a deep, satisfied moan, his clit letting loose with pleasure and my own followed suit as he started fucking Bad Teddy. His legs pumped him up and down like a pro, as if Izzy had done this as much as I'd jacked it and that might have been the case.

Some part of my brain that wasn't content with watching got me to rise, with a hand still holding the dildo in place, and slowly closed the tiny distance between Izzy and I, who paused in his vigorous fucking to kiss me. There was no hint of the smug Izzy seen previously but rather one in the throes of lust and close to release.

Sitting in Bad Teddy's lap, he pulled me into his chest with one hand and started working my nearly endlessly leaking clit with the other. And thinking of me as having a sissy clit was still painful but the good sort of pain, the kind like the dildo going in for the first time that became pleasure. Just of a sort so bright I coldn't take very much of it. I kissed and sucked at Izzy's bust as he swayed, still not stopping in his motions even as I made him feel good up top.

Still using one hand to keep the cock in me and to push it up every so often, I peeled off of Izzy and pushed him back every so carefully as I lowered to his still in motion hips. Izzy's clit was soaked and still dripping when I licked it, getting a taste before taking all of him in my mouth. He shrieked and I had to move along with him as he started frantically riding Bad Teddy as I worked in the dildo in my ass faster as a burst of semen fired in my mouth. I tried to split my attention between him and me but finally Izzy stopped moving and his hands tapped me on the back of the head, bidding I rise.

"No one's ever done that for me before." He said in a quaking voice as I sat back on my haunches, not needing to wipe my mouth as so little had been produced. "Thank you thank you thank you-" I stopped his stream of consciousness by kissing him and then was amazed as he started riding the dildo again. Twice more Izzy got off, each time I was there to encourage him and then swallow the results. There was no massive load, nothing I could open wide and show a camera if it happened to be there.

By the time he rose off of Bad Teddy's lap, I was more than ready to take my turn. Pulling what I'd been using out felt beyond strange but Izzy got me lubed up, telling me to take it slow as I straddled Bad Teddy, legs shaking and I found myself both ready and astonished at how much I wanted this. I knew this dildo was bigger than the last but when I lowered myself to it, that ended up not mattering at all. Izzy's eyes went wide but I barely noticed, being taken by that temporary mindless wonder of a long and hard dick entering me. When I sat on the bear wearing a strap on harness I came instantly, my legs not quite feeling the fur as Izzy returned the favor, his tongue teasing out the shattering orgasm that didn't have a resulting amount of cum.

But that wasn't enough. My ride on Bad Teddy was slower, with Izzy encouraging me all the while. He stroked my hair, offering advice on getting the right angles and told me I was riding this cock like a natural. I moaned at hearing that and it only encouraged him, playing with my tits as he spoke of the rose not being wrong, I was an excellent sissy. I was well warmed up to Bad Teddy's package by then and that powerful electrical surge finally overflowed, crackling as it fired all over my body and Izzy was there to catch the spill.

Finally my legs gave out and I fell forward, no longer worried about being empty or full but rather of being awake or asleep. The night had been long and I needed to recover from both the physical and mental. Izzy climbed off the bed and headed out of the room before returning with a damp and cold washcloth be used to clean me up, then himself.

"Welp, bed's soaked in sex. Gonna have to sleep on the couch." I nodded then accepted the clean pair of panties he gave me, changing without thinking. Then I carried the balnkets and a pillow into the living room, the candle still lit and providing enough light for us to get situated as I drifted off quickly, not hearing what Izzy was saying.

Light actually woke me, looking around confused and finding it wasn't the candle or a phone but rather the room's main light was on. I lay there, confused until, with some clanking, the heater kicked on.

"Oh hey, power's back on." Izzy said, his voice fogged by sleep and that was all said about the matter as I passed back out. Later I was woken by Izzy, who shook me until I rose to find a plate with a waffle covered in syrup, instantly waking up my stomach as my brain floundered in confusion.

"It ain't breakfast in bed but ya know, sheets need washed." In a Tshirt that only seemed to show off he wasn't wearing a bra and make his legs look longer, Izzy sat beside me with a waffle of his own and flicked the TV on. He found a music channel and we listened to the soundtrack to some video game I'd never heard of while eating, my body demanding food before anything else. Once the waffle was gone, I hit up the bathroom and was faced with the changes I'd inflicted on myself.

With the power back, I was able to see my reflection in the bathroom mirror and found I wasn't too surprised but couldn't look away. Instead of the sleepy resting expression I usually had it was more of a sultry smolder, with my eyes half lidded and not quite threatening but none too inviting. So that hadn't changed. But boobs were new, hanging there on my chest and checking myself out made the nipples stand tall a midst the larger spots of color. And I had a figure, one that invited me to touch it and so I did, hands touching the waist of the light blue panties that looked like it held nothing out of the ordinary.

Unable to help it, I pulled them down and shivered at seeing what lay under there in plain light for the first time. I hadn't known a penis could even look like this before Izzy showed me and here I was with one of my own. With a funny fluttering of heat in my stomach, I sat on the toilet and did my business, aware of more soreness around back and found no shame in replaying last night's memories. 'I'd fucked a teddy bear' wasn't a line I was going to lead with during the next conversation at work but it had been a damn good ride.

Once done there I rejoined Izzy in the living room, snuggling up to him under the covers as he chocked his phone and powered it down.

"Town's under like six inches of snow and a while bunch of ice. Hope you didn't have plans." I shook my head, mentally noting I had to call into work tomorrow as trying to walk anywhere probably was a bad idea. "How are you feeling?"

"Better. Had breakfast and the heaters on." My answer wasn't what Izzy wanted and he poked me in the side, getting a jump for his efforts.

"No! About that night! About us and you and all that!" The music was soothing and I closed my eyes, reaching out to rest my hand on one of Izzy's boobs as I gathered my thoughts.

"I feel good about it all. " Anything more I would have said was cut off, Izzy's voice taking on a sly tone as he spoke.

"Even with your sissy clitty?" I grunted at hearing that and he giggled, hugging me close. "I only bring it up cause it bothers you and I want to know why?" In the darkness behind my eyes I went looking for the answer, trying to put primal emotions I wasn't quite sure of into words.

"It sounds perverse." At that, Izzy laughed and I opened my eyes, not offended but lining up what came next.

"Sorry! That's just weird to me!" He sounded genuine and I believed him but wanted to say it, make it more real.

"It's not just that. Hearing it is off putting at first but it makes me feel like nothing else I've experienced before. I still can't believe I've got it, to be honest. I..." I thought back to that chilly bedroom and seeing Izzy's junk so close to my face and seeing it as an open invitation rather than a moment of crisis. Of seeing what had to be an average sized condom and realizing it was of no use to me and how no one could reasonably expect me to be a man with so little manliness to show.

"It's a rejection of what I was suppose to be. Never had a girlfriend, wasn't sure how to talk to a girl even. Didn't like guys, they were all into things I didn't care about and didn't find any of them attractive. Was pretty sure I wasn't gay but... Am I? Are you?" I was staring up at the ceiling, talking from the heart and waiting for Izzy to answer, to see how he was treating this.

"Not sure, honestly. I thought of it like sissies are ex-guys. Like someone who's retired from the Marines is an ex Marine, ya know?" I nodded, sort of following the logic. It was more being defined by what came before rather than what was now but the term sissy seemed to have so much baggage maybe it could sum up all those thoughts. "Funny thing is sissies usually find a guy or a woman who's good with a strap on and stick with them. I honestly can't recall reading about two sissies getting it on but I liked it." His hand crept into my crotch and began rubbing, not quite reaching what he was probably after but the action was getting me into the mood.

"I did too." I said, feeling Izzy's boob and that not yet familiar rush of heat to my lower half but there was no resulting stretching and standing. No, there was awareness and a slight bit of wetness but that just seemed to be the way of things here and now.

"So I got one more good thing to show off but before that I want to ask you a favor." Izzy faced me, his hand venturing about until it found a damp spot in the panties and my nub behind it. "I want to hear you say it and I'll reward you."

"Say what?" My question got a grin in response and I sighed, knowing what he wanted but still not sure why.

"It's not that big of a deal, you said so yourself! And it turns me on. I've sucked dick before and eaten pussy but being told to do those things is exciting! Like, you need it so bad you have to tell me! So come on, try it out?" It was then I was reminded I only sort of knew Izzy, mostly through a weekly card game and his sexual habits were mentioned but he never divulged any information. Still, he had done so much for me, and to me, that I owed him this.

"Izzy?" I said and there was no air of command to it, making him raise an eyebrow. "Would you suck ma-my sissy clit? Pl-please?" My stomach clenched hard at saying it and I shuddered, adding yet more to the wet spot in the panties I was wearing.

"Well, I can tell ya need it but more in a pathetic way, ya know?" He said it with a grin, the blanket falling to the floor as he pulled the shirt off, revealing his chest and red panties that failed toe betray his true nature. "And I'm not going to lie, that's still pretty hot." And he lowered me to the cushions of the couch, smiling when I spread my legs. He pulled the underwear off and I was already breathing hard when the warm air touched what still wasn't standing upright.

Plush lips parting, Izzy locked eyes with me as he went down, his tongue snaking out to touch what I'd asked him to suck. I wasn't sure if I had some weird impotency fetish bit I was still amazed by no matter how much I got turned on, the thing that was supposed to show it refused to. I gasped as those lips kissed my smooth skin, my dick not being deep throated, as that was impossible now, but Izzy's talented tongue playing with it instead.

Before too long I took hold of the couch's back as the rising tide of pleasure pulled me under, the shudder that went up my back not nearly as powerful as the one's Bad Teddy had given me previously. Swallowing, Izzy looked at me with thoughtful eyes before standing and peeling off his panties. Still floating on a wave of good vibes I wasn't bothered by what I was seeing and instead welcomed it when Izzy put a knee by my head and was once more over me.

This time I had to rise to meet Izzy's dangling offering, my hands going to his hips and as I returned the pleasure he'd given me. A moan then another feeble dribbling from Izzy rang out and he crawled from over me, instead laying with his head propped up by the armrest and his legs spread, an invitation I took.

"That's right Chris, from one sissy to another, blow me." He was breathing hard and I wasn't sure what was going on with him but I did as he asked, his legs tensing as I began. "Oh God yes, yes..." I ran my tongue on the underside of him as he kept moaning, some words mixed in there and I was dripping on the couch but that wasn't important now. No, what had to happen was the emptiness Izzy's showed me I carried needed filling soon. Without thinking, I reached back and, using what was now the standard two finger tug, began taking care of myself.

"That's right, play with your little clitty." Izzy said, voice lacking venom but his words still caught me off guard. "I know what you want and you'll get it soon enough." Unable to continue, I rose from Izzy's crotch and, wanting that fuck he was promising right now, I straddled him and sat down where my head had just been.

Just like he had done last night, I began grinding on him but got nowhere, Izzy being too small and floppy to get me anywhere except slightly went.

"Sorry, this sissy's got a clit instead of that dick you want." His grin was uneven and my unspoken question made him sigh. "Look, I suck at dirty talk, alright? I wanted to try it out cause some sissies like that sort of thing but..." He shrugged and shook my head, unable to hide the smile at how bad he'd bungled it.

"Hey, I wasn't kidding about knowing whatcha want." I rose off of him and Izzy bounced up, gesturing towards his bedroom and I followed him, admiring the view now that he wasn't wearing anything. Since joining the group for weekly Magic, I'd felt ashamed of checking out another guy's ass but now? It was damn fine and having felt it knew it had enough give and filled my hands, which wasn't saying much considering them seem to have shrank some along with the rest of it.

"Like whatcha see?" I jerked out of my head, seeing Izzy peering over his shoulder at me. "Go ahead." Now in his bedroom, the sheets having been stripped off the bed, Izzy crawled on the bare mattress with his ass exposed to me. Unable to stop myself I joined him, hands running over the bubble butt that had fucked Bad Teddy before bringing my own hips to his ass.

Izzy's butt was one I'd loved to have fucked but even this view, this chance, wasn't enough to get me hard or even any bigger. So instead I settled for dry humping him, my nearly useless dick flopping about until I started grinding on one of his cheeks before giving up.

"I'd seen ya looking and figure you'd wanted to do that for a while." Rolling off the bed and onto his feet, Izzy patted me on the cheek, giving me a kind and slightly sympathetic look. "Sorry it wasn't as good as you wanted."

"I mean, I did want to do that and thanks but I'm still happy with what I got." Heat flooded my cheeks as an idea occurred and I grabbed hold of it before it could escape. "Do it to me." Without saying anything more, I took the same position on hands and knees. I felt him climb onto the mattress behind me, his hands warm as they touched my ass and then moved to my hips.

"Your ass is amazing Chris. Too bad you shacked up with a sissy who can't fuck it like you deserve." Even still he thrust against me, not too hard but enough I cried out, finding having him behind me unexpectedly alluring. Another thrust and he reached around, two fingers once again about my clit and he only pumped when his hips met mine. My boobs moved along with the impact and I cried out each time, not sure how else to deal with this. Izzy behind me, even without any penetration, was enough for my brain, for me. I was being fucked doggy style and my sissy clit was getting attention and I let loose, each shudder that flowed through me being met counted with a moan. I'd been fucked and it felt good, right even.

I fell over on my side and lay there for some time before raising my head and looking around, finding Izzy had left the room. I rose, went to the bathroom and found the washcloth and cleaned the wet spot I'd made on the mattress, trying to be a good guest. As if us fucking what felt like an entire night didn't qualify me as guest of the decade.

That done I went to his underwear drawer and idly looked thought too many panties before finding a pink pair with a high waist and with a ribbon winding up the back as if it was a corset and tugging on that would tighten it. They were fancy and looked expensive but I had to know. Slipping them on, I closed my eyes and took my time pulling them up, the thrill I first felt when a teenager returning now, except now I had no rock hard erection to ruin the look. I felt the fabric slide up my prick but stopped there, heart going a mile a minute as I sucked down air.

I was freshly humped, sucked a sissy's dick then sat on it, as if it might suddenly spring to life and be able to provide what I craved. All of that and it wasn't even noon yet, I'd checked while eating. I'd attempted to hump Izzy in a typically male manner and failed, of course I had, acting on a instinct born back when I had a dick. That thing that sealed the deal was the condom, a standard of normalcy I could no longer fit nor was it's function even useful anymore. My sperm count had to be somewhere around seven, given my balls were small enough to disappeared up into my body. And now I was raiding Izzy's panty stash like I was in a 80's raunchy comedy taking place in a college.