The Chance Fantastic Pt. 04

The Chance Fantastic Pt. 4 - The Flowering

The holidays were coming up. Thanksgiving was never that big a deal for me. I didn't love the cuisine as much as some other people, and my family never made a huge deal of it. Since college, I haven't ever bothered to even fly home for Thanksgiving, as it was such a short turnaround time it hardly seemed worth the money, time, and effort. Besides, I didn't want to waste my PTO on taking the Friday after Thanksgiving off. Most of my friends were leaving. Jordan was heading back home, as were Johnny and Stewart.

The only people not traveling for Thanksgiving were Greg and Abby. Their parents were off in Europe, so there wasn't much of a point in traveling home. They had some cousins they would spend the actual day with. Besides, that Saturday after was the Brad Paisley concert. Greg couldn't have been more excited.

I told them that I would be spending the day with cousins too by way of declining their invite, but the truth was I had also declined my cousin's invites. The food wasn't worth putting up with hours of cousins who I didn't really like. My cousins were all super athletes of the worst kind. One had even made it to the NFL. They were all A-type personalities that thought they knew everything, and I wasn't in the mood to spend an afternoon listening to them berate me for not investing my money in one scheme or another.

In addition to skipping the cousin scene, spending Thanksgiving alone had other advantages. I found it truly rare to have a full day with no expectations. No social pressure to be doing something else with someone else. A full day where you could sleep however long you wanted, eat when and what you wanted, play as many video games as you wanted, watch what movies you wanted, etc. Everyone else was busy, and nobody expected you to do anything. Thanksgiving really could be the most relaxing day of the year. I had done this before in recent years past, and it really made Thanksgiving much more enjoyable for me.

This year, I planned on spending the day in full femme. I would have a sissy hypno stream on all, day, maybe jump on and cam on my hookup site, stick a dildo in my ass, and have a go at finding my g-spot. I was excited. I had recently bought a new lingerie set, a black lace strappy number with a corset, and I wanted to try it out. I also had acquired a black little cocktail dress to put over it that had just loose enough a bottom so that I could still flash my panties when I wanted to. I hadn't had an interactive stream yet - guys apparently didn't want to comment much on me - but I at least received a few visitors in my recent streams, and I was eager to see if I could get one to start telling me things to do to myself.

I tried to start the day slowly enough. I showered, had a decent breakfast, and scrolled through some memes. I then meticulously did my makeup - I was getting much better. I had also bought some false eyelashes that really helped complete the look. I found that mascara was maybe my favorite bit of makeup. I particularly liked it when I could get it to run after choking on my dildo. That made me look extra slutty. I even ran a comb through my wig. I then attached my breast forms, being sure that they were even. I slowly pulled up my stocking, relishing the feeling of the tight, smooth material on my soft skin. They had little bows on top that I thought were darling. I pulled up my panties next. They were lacy around my crotch and bum, with a little heart cut out to show just the top of my clean-shaven ass crack. Two straps ran diagonally across my hips on either side.

Then came the corset. The corset was fairly difficult to lace up by myself, but it was worth it. It took me a few tugs, with rests in between to catch my breach, to give myself the beginning of the hourglass shape I wanted. Truth be told, my exercising and healthy eating were starting to work. I had dropped about 10 pounds, down to 155, but I'm fairly certain I had gained some weight in my ass. It had a nice round shape to it, even if it wasn't big. I carefully attached the bottom straps of my corset to my stockings. I had to work a bit, as I remembered that good girls always put on their panties after attaching their stockings so that they could take off their panties without needing to remove the stockings. I had to run the straps through my panties. It wasn't graceful, but what did I care. The camera wasn't on yet.

The corset pushed my breasts up a little bit, but not too much as to dislodge them. I had a black little choker that said "cum slut" on it that I attached. Even in my cocktail dress, I wanted to remind the boys that I was a slut. The cocktail dress came next, and I gave my skirt a little flick to make sure I could show off my sexy goods underneath. And finally, strapped on my four-inch heels. This was the only part of my outfit that wasn't black. While I had invested substantial money in my girly wardrobe (I didn't even want to add it all up to know exactly how much), I still hadn't decided to buy multiple pairs of shoes. I had my limits. But the pink shoes added a splash of color, and they perked my little bubble butt up just enough to be noticeable to me.

I logged onto Vivienne's grotto and slid it over to my recently purchased second monitor. I then booted up my hookup site. I had ponied up for a paid purchase. Most of the messages that got sent to me either never replied to my responses or were bots. But I hadn't been aggressive about seeking people out, so the number was fairly small. I had one guy who liked trading dirty emails for a bit, but he never manned up to try to meet up (though I would have declined even if he had). I checked to see if rm_shymas was on, and he was not, so it was safe to proceed. I turned on my webcam, and updated my status to say that I would be on cam for the rest of the day if any big cocks wanted to play.

That was a little change from when I first got on the website. When I first got on, I never specifically try to reach boys. I was open to them because sissies were supposed to be open to all callers, but I was still mostly interested in girls, I told myself. Now, a few weeks later, I definitely targeted men. They were much more likely to respond and much less likely to be a bot. It was much more fun if I thought a real person was involved in the interaction. And for me, this camming was all about attention.

After about 30 minutes, my first visitor joined my stream. Generally, these people would stay for a minute or two, and then leave, but I still typed in my obligatory "hey buckster 16, want to have some fun." Unsurprisingly, he didn't respond. They never did, in my experience. I was eager to get to a show, but I wanted to be patient. I had all day. Buckster would probably log off soon. Before he did, though, a second person joined. "Hey jtsmooth, got any requests?"

For the first time, someone responded. "Show ass." It wasn't elegant, or even well written, but I was so happy to have someone respond, I just went with it. "Your wish is my command, daddy ;)" I typed. I didn't have my mic turned on as I didn't trust the believability of my female voice yet. I stood up, gave a coy little wave, and did a twirl, letting my skirt blow up a bit with the motion. Turning my back to the screen, I bent over at the waist, slowly drawing my skirt up with one hand so that my panty-clad ass was on full display. I swayed from side to side, and gave my ass two gentle claps.

"Thats hot, u sexy" jtsmooth wrote. And then, a third person joined the chat. This was the most I had ever gotten at one time. Nakedfun needed no introduction "spread cheeks pls." I almost listened, but I needed to spread out my show some more. I straightened up, but kept swaying seductively from side to side. I turned a bit, and winked at my audience, before lifting up one side of my skirt to show off my butt. I gave myself a slap, causing a little jiggle, and turned around to face the camera. I bent over and typed "hey nakedfun, I'm glad you could make it to the party. Do you like my ass?"

Jtsmooth responded first, "I love ur ass. Can i see more?" Eventually, Nakedfun managed a "yes," which wasn't exactly the reaction I was hoping to elicit, but it worked. I had two engaged participants in my room at the same time. I smiled, straightened up, and kept my sexy side-to-side dance. I didn't really know what else to do. I was new to this, after all. I lifted my skirt again, this time showing my bulge to the camera. No one commented, which was nice.

I turned around again, and bent over, shaking my skirt so it fell over my hips, revealing my ass. Without taking off my panties, I spread my cheeks a bit so they could clearly see the bejeweled butt plug I was wearing. "Ooooh, you sexy gurl," jtsmooth said. Then Nakedfun added, "do you have toy?" I don't know why these guys had something against using articles in a sentence, but hey, they were typing one-handed, so I guess I could forgive them a grammar error here or there.

"Of course honey, I can't live without cock ;)" I typed, smiling, I reached over and pulled out my dildo. At that point, two more guys joined the room, almost one right after the other. One stayed quiet, like my first participant, but sirjuicy wrote "what's going in here?" Nakedfun responded, "some guy dressed like a girl is about to suck a cock." sir juicy wrote, "one of those freaks. Still, he's not bad."

So someone was living in denial, I thought to myself as I brought my dildo close to my lips. Pretending to think that sissies were freaks, but entering and staying in my stream because he actually thinks sissies are hot. Well, a guy's gotta do what a guy's gotta do. I typed, "who's cock am I sucking today?" Jtsmooth was the quickest to respond, "meeee!"

"Mmm, jt, your cock is so big and hard, and you smell so big and manly," I started rubbing my chest with my other hand for effect after typing. "Can I please get a taste of your hard cock?" "Oh bb suck my cock," came the quick reply. I planted a soft kiss on the tip, typing "just imagine my soft, thick lips running gently down your shaft." I then started planting kisses slowly down the shaft of the dildo, letting one or two linger with my lips just on the dildo. When I got down to the balls, I took one in my mouth. Even though they probably couldn't see, I swirled my tongue around it. I was starting to turn myself on quite a bit, and getting into the show.

I took a chance. I turned on my mic. I wouldn't talk to them, but my moaning was fairly convincing and realistic. I smiled as a few guys left more "ur so hot" comments. One demanded that I suck the cock. The first guy who had entered the room had left at this point, but two more had shown up. My stream was starting to get some attention. I took the tip of the dildo in my mouth, again swirling my tongue around it. I did a few slow pumps, just to get the boys going. Then I typed, "who wants to see how far I can take their dick down my throat?"

"Choke on it bb, suck daddy's cock" was the first reply. I smiled, and started my process. I started bobbing up and down it, taking it a little deeper each time. When I was getting close to the back of my throat, I took a deep breath, and then pushed it all the way back. When it hit my epiglottis, I choked - I hadn't been able to completely eliminate my gag reflex yet. Truth be told, I kind of liked treading the line between choking and vomiting. Choking was sexy. It showed dedication to dick-sucking - a guy would really believe I worshipped his cock if I was willing to literally choke on it. Plus you got all those nice markings of a true depraved slut: runny mascara, that spit that would dribble down your chin and onto your chest, the red cheeks.

So for me, the key wasn't necessarily eliminating the gag reflex, it was beating it. Mentally working past it to get the dildo down my throat. Pulling the dildo out of my mouth, I showed the guys the string of spit that connected the cock to my lips, and I started again. Again, I worked up to it slowly. This was still a show, and I wanted to drag it out. I was up to eleven viewers. This time, when I got to the back of my throat, I started to choke, and then stopped, leaving the dildo just hovering in the space between my safe mouth and my throat. With slowness, I eased it further in, reminding myself to breathe through my nose the whole time.

This time, I got it down. Sometimes, it would take me two or three attempts to beat the gag reflex, but this time, I could see onscreen a pleasant bulge down my throat. I lifted my head up so the guys could see it too. I started to pump the dick in and out, never fully withdrawing it from my throat because doing so would start the process all over. Eventually, though, the deep-throating had to end - a fake cock would never cum like a real one. Pulling it out, I gasped, letting the spit spill over my chin. "MMMM," I moaned, licking my lips. "That one goes out to jtsmooth - I just can't stop thinking about his cock ;)" I typed.

Then, boldly, I followed up with, "do any of you boys want to show me your juicy cocks? I love cocks!" Soon enough, my chatbox was filled with images of cocks. Now, a cock is not a very aesthetically pleasing object, objectively speaking. Even though I was pretty deep in the sissy mindset at this point in my journey, I hadn't really found a cock to be attractive. I understood their utility and their role in my journey as a sissy, so I played to the crowd. But looking at a chatbox full of cocks that were hard because of me, I found myself actually examining them.

Some were short and fat, some were fairly average in all respects, some guys had mastered the art of angles that made their cocks look bigger, and one or two genuinely had a huge cock. I tried to compliment all of them, "oooh, your cock would stretch my ass so nicely, Nakedfun," "I can just imagine your cock going down my throat, mysteriouspleaser," "your balls look so good, alphadog, I wish you would just dangle them on my lips."The guys enjoyed it, but I knew it was time for some more visual aids.

Standing up again, I gave my skirt a flick, giving them a glimpse of my panties. Slowly pulling it up, I let my bulge sit out there for the world to see for a beat or two. Swaying side to side, I reached up to the shoulder straps of my dress, and let one fall off. I had always had delicate shoulders. Wearing a dress finally made them seem right. I let the dress fall off my "boob," exposing my lacy black bra. Groping myself, I started to rub my fake nipple through the bra, moaning. With my other hand, I clumsily typed out, "all your cocks are getting me so worked up, boys."

I turned my back to the camera, and with a seductive wiggle, I let the dress fall to my ankles. Instead of just kicking it away, I bent at the waist to pick it up, giving them a good view of my lacy panties bulging with my full ass. I knew my smooth crack was on display, thanks to the heart-shaped cutout. Before standing up, I looked back, flicked my hair using my head, winked at the boys, and gave my ass a slap. I was glad none of my roommates were around to hear it.

I arched my back a little as I stood up. Giving my ass a wiggle, I hooked my thumbs into the edges of my panties and pulled them down just a bit to give the guys a better view. Then, bending over again, I started rubbing my ass cheeks, eventually using both hands to spread my crack and put my boi pussy on display through the nearly see-through lace. I didn't actually want to take my panties off. Not that I was ashamed to be naked in front of these guys. Clearly, shame had left my body some time ago. It's just that the panties were what made me girly. Without them, I just looked like a guy playing dress-up. With them, I could look back and see a sexy-ass girl playing for the camera.

But with the stockings and the corset, I think I could make a go of it. These panties did not really lend themselves to being pulled to one side, especially with the stocking straps. I stood up again, still with my back towards the camera, and started pulling down my panties, shimmying slowly down as they inched down my ass. I was now bare-assed in front of a camera, preparing to fuck it with my dildo for a sizeable audience. I couldn't have been more turned on.

Sticking my dildo back in my mouth to pre-lube it, I typed, "what would you guys do if I was bent down on your bed?" As expected, the predictable but still intoxicating replies came in, "id fuck your ass," "id teach you to call me daddy," "id cum in your ass, and then make you lick my cock clean."

"Be nice to me, and your wish may come true ;)" I sent across. I started lubing up my dildo for real, stood up, bent over, and pulled my panties to the side. I could hear the bings from my computer as more comments came flooding in at the sight of my exposed butt plug. I gripped the base, started pulling it out, and then pushed it back in with a theatrical moan. I masturbated just a bit with it before pulling it out all the way. I saw that one of the comments asked for me to lick it, but there were some things I wasn't ready to do quite yet. I wasn't a porn star, after all.

I poured some lube on my hand, and made a show of rubbing it all around my rosebud before pushing one finger inside, again inspiring a moan for the benefit of the audience. Slowly, sensually, I worked my finger in and out, hitting my asshole from all angles. I paused for a moment to elicit some encouragement, "ohh, it feels so good," I typed, "I don't want to stop."

"Fuck ur ass, girl. Let's see you ride that cock." Pulling my finger out, I positioned the tip of my dildo at the base of my ass and pushed in slowly. I could feel it starting to bend, so I stopped and adjusted. That would be embarrassing on cam. This time, I felt my ass split apart as the cock penetrated me. For once, my moan was not forced. Fucking my ass didn't feel good, per se, but it was now so entangled with the sensation of masturbating that it triggered happy, pleasurable spots in my brain, and made me feel sexy. I pushed the cock farther in until I could feel the base with the balls and the suction cup resting on my cheeks. I paused here and bent around without taking my ass off screen to read more comments.

Some guys had left, but one or two had left comments like "damn girl, that was sexy." Some guys were requesting to see my cum now. I was getting there, but I didn't want to end the show quite yet. I was at 14 whole viewers, and I couldn't feel sexier. I nearly pulled the dildo out all the way, before starting to slowly but rhythmically pump my asshole. Moving my computer chair to a better position, I put one leg up on it so that the guys could see my cock being rubbed as I continued to pump my ass. My moans were quite real at this point, and my thoughts were starting to get carried away.

I thought about rm_shymas, and how hot it would be if he joined the room right now. I almost turned to look to see if he had, but I was too caught up in the moment to really stop. I began to think about what it would be like if the cock in my ass wasn't a cold dildo, but a real, warm cock, attached to a man who found my ass sexy. I thought about the spurt of warmth I would feel if I made him cum. More images flooded my brain: me, kneeling in front of a cock, lifting it over my face as I prepared to suck his balls; me, lying between two legs, softly sucking a flaccid penis back to life; me, on a couch, being spit-roasted by two guys. I could feel my orgasm building.

I turned so I was perpendicular to the camera. I carefully attached the suction cup base of my dildo to the wall. Positioning my ass, I now could see the screen as I started to push myself back up and down the cock. I could see the requests come in, and I typed, "where do you boys want me to cum?"

"Cum in your mouth," "swallow it down bb," and "cum on the screen for us," were the three general categories I was given. I always found facials the hottest. I even got into bukkake porn for a while. But in my current position, I wasn't able to position myself to do it. And, I realized, the point of no return was fast approaching. Deciding not to ruin the rhythm of the moment, I came in my hand with a loud "OOOOOh uhhhh."