Straight to Sissy Ch. 04

A Note From the Author: My sincere apologies about the length of time that has passed between publishings. This story is a continuing work in progress. It has been conceived and written over many years and I work on it as a hobby, often forced to take long breaks in between writing sessions to tend to other life responsibilities. But rest assured, I intend to continue to write and publish as I go. Hopefully you can bear with me and enjoy it as it comes.

Chapter 4 of the adventure. I find myself on the floor of my new Master's home, dazed after having just lost my anal virginity. Patiently, I wait for his next orders as he continues my introduction to sissification.

I could hear Master typing on the keyboard, the intermittent sounds sending me into a hypnotic state as the shock of what had just occurred washed over me. Time seemed to disappear as I got lost in my thoughts. Am I going to have to shave? Wear makeup? Is this man planning to pimp me out, have me gangbanged or worse? I didn't really know what to think at this point, but I knew I wanted another round of his cock and I thought maybe I really was becoming a slut.

My imagination had wandered to an image of me, dressed in a frilly pink camisole with a garter, sheer pink leggings and my hair long and dyed blonde, in two ponytails held up with big pink bows. I'm going around a large room filled with dozens of men seated in a circle, all of them naked with hard throbbing cocks as I worked my way around the room, using both my holes to milk their cum from their cocks until none were remaining and I was a sloppy cummy mess. Is that sissy heaven?

Master pulled me from the fantasy as I heard him ask, "Are you ready for another load sissy? Looking at all these great pictures we got of you is making me horny again."

I craned my head towards the screen, struggling to get a look from my vantage point. "What the fuck is he doing with my pictures!?" I thought, worriedly. I caught a glimpse of him scrolling through an album, my image popping up on the screen with each click. I let out a futile moan through my cock gag, tasting the remnants of his cum still in my mouth.

He got up from the computer and walked back over to the bed. My eyes gleamed when I saw his huge cock magically hard again and ready to plug me. He laid down behind me and held me, grinding himself in between my cheeks, slowly shoving the plug deeper into my sore ass.

"Don't worry bitch, I'll give that tight little pussy a break for the night and give you a full load for you to take home in your mouth." He retrieved a pair of scissors from the bedside stand and finally cut my bindings free. My joints ached as I stretched them out, and I leaned over eagerly looking at his stiff black cock.

"You want to suck it don't you bitch?" he asked. "Mmhmmh" I nodded and I leaned forward so he could remove the cock gag. As soon as it was out of my mouth, I quickly crawled down and shoved his meat into my mouth, like a hungry animal. I couldn't believe how I had been transformed like this in just one night.

He laughed and said, "Easy there tiger, start me off nice and slow."

I immediately slowed down and started to lick gently around his head, and then sliding my tongue up and down the length of his shaft. I took his head back into my mouth and sucked, savoring the taste of his precum as I swirled my tongue on the sensitive underside of his cockhead. Then I sensually sunk it deep in my throat, slowly picking up the pace, lost in concentration trying to get him off. I could tell he was enjoying my work as his cock would twitch occasionally, giving me another taste of precum. I sped up as much as I could, eager to milk another load out of him and prove that I'd learned a thing or two about cocksucking tonight. Soon, I felt him hold my head in place and he started to move his hips a bit facefucking me even faster. Then he tensed, pulled most of his dick out while leaving the head in as he jerked the shaft, depositing a huge, thick load right onto my tongue.

"There you go slut! I hope you enjoy that midnight snack of yours! Hold it in your mouth and open wide to show me." I did as he asked and tasted the creamy salty goodness swirling on my tongue. "Good sissy!" he proclaimed as I beamed. "Now remember, you must always keep your reward in your mouth until a man tells you to swallow. A good sissy loves holding cum in her mouth, it's like her own version of listerine. You can close up now and keep it swirling around in there until I tell you. And you can thank me later. Such a lucky slut getting sent home so full of cum! Keep that plug in and let's go, I'm done with you."

He put his clothes on quickly and he headed toward the door. I scrambled off the bed and crawled after him, the plug shifting in my ass as I moved and the smell and taste of cum invading my senses. I did feel like a good sissy. Here I was, crawling after a man who had just utterly used me, literally filled with his cum in both of my holes and still utterly craving his attention.

We made our way out to the car, I was crawling close behind, my knees aching after my night of service. "Hopefully, I'll get used to this," I thought.. He popped the trunk and told me to get in. I was a little surprised at this direction, and I looked up at him sadly. He laughed and said, "Maybe when you look like a proper slut I'll let you ride up front, for now you can ride in the trunk like any other property of mine.

I nodded and crawled in and he slammed it shut above me. I curled into the fetal position in the darkness, continuing to savor his cum in my mouth and feeling the plug in my ass. I heard the car start up and begin backing down the driveway. The power this man now had over me was overwhelming. I realized he completely owned me now, and I could only hope he'd actually deliver me home like I wanted. At this point, he could totally have just dumped me off at some gay video booths or truck stop and let me get used like a whore.

Finally we came to a full stop. I heard a car door slam and bright lights suddenly blinded my vision. My eyes focused and I realized I was on the street in front of my condo. I crawled out of the trunk and remained kneeling in front of him. He pulled the waistband of his sweats down and told me to kiss his cock goodnight. I leaned forward and gave his head a peck, careful to keep his load in my mouth.

"Ok slut, crawl home," he ordered, throwing my shorts in front of me on the ground.

I realized I wasn't going to get the privilege of even walking back to my home. Used sissies crawl, especially when still in the presence of her Master.

I heard him shout behind me, "Don't swallow that cum sissy! I'll text you when I get home."

When I made it to my door he drove off and I was able to enter the safety of my house. I struggled to my feet and practically stumbled towards my bed. I was completely spent and couldn't believe what I had done tonight. Hopefully Master will text me soon so I can go to sleep, I thought.

I laid in bed recounting the events of the evening. I felt myself rubbing the tip of my dick thinking about it. I was still horny despite my tiredness and even though I knew it was forbidden, I figured my Master would have no way of knowing my infringement.

Finally, my phone buzzed. I glanced down at the screen as I kept rubbing, the pressure in my balls building again. I didn't dare cum without permission of course. I stared in shock at my phone as I looked down and saw the message. It read, "are you touching your little clit right now slut?" How could he possibly know!? I knew it would be best to be honest at this point.

I stopped and quickly typed out a reply. "Yes I'm sorry Sir, I'm so horny thinking about being a slut for you I couldn't help it. It won't happen again."

Nervously, I waited for a response. I couldn't believe I had fucked up already. He was right, I did have a lot of training to go.

The phone buzzed again, "You're right sissy, it won't happen again because we're going to be locking that clit up soon enough. And you will be punished for this infringement. For now, time for you to record a little video. When you're done, I'll send you the link so you can see your sissy profile. Start off opening wide, showing off that nice load in your mouth. Swallow and tell your fans how yummy it is. Then, turn around and slowly take out that plug. Look back at the camera as you clean it off and make sure you scoop up anything else trickling out to clean up. A good sissy savors every drop of cum and never wastes any! When you're done with your snack, pop the plug back in and tell your fans how much you loved being used tonight."

I shuddered as I read the instructions. What the fuck was he talking about?, I thought to myself, wondering what he meant by "sissy profile." I started to type out a response, before thinking better of it. I shouldn't ignore Master's instruction, I decided.

I dutifully sat down at my computer, pulled up the webcam and hit record. I opened my mouth wide, I showing off his load as instructed. I gave it a few swirls and then took a deep swallow, smiling and then opening back up again to show it was all gone. "Yummy!" I exclaimed, "I love swallowing a big load of cum!" I turned around and shook my ass towards the camera, showing off my plug. "I'm such a lucky sissy! I have another one waiting for me in my pussy!"

Reaching back, I slid the plug out of my hole. I felt a stream of cum coming out and I let it build up on the tip of the plug. I looked back again as I brought it to my mouth, licking the milky fluid seductively off until the plug was clean. I pushed it around the entrance to my hole again and squeezed my muscles to coax a little more out. Cleaning off the plug I smiled at the camera and popped it back in.

I turned around for my little monologue. "Well I got totally filled with cum tonight and I feel like the biggest slut in the world! My holes are sore and it's the best feeling and I can't wait to be trained to be an even bigger and better slut. My dreams will be filled with cock tonight and I hope I get fucked again soon! Thank you for treating me like such a sissy tonight Master!"

I sent the video out and crawled back in bed. Just as I was dozing off, I heard another buzz. It was a text from Master and all it contained was a link to a Twitter page named "Perfect sissy sextoy."

Clicking on it, I was sent to a page filled with about 2 dozen videos and images of me taking Masters cock tonight. It even included the videos of me begging to be turned into a sissy and the one I had just made. My profile picture was a closeup on my face, my eyes wide and my cheeks puffed as Master's huge cock filled me to the brim. My bio read "I have recently discovered my only purpose in this world is to serve cock and to be filled with cum. I'm lucky enough to have found a generous Master who will train me to be a perfect slutty sissy.. I don't have a name anymore, so you can just call me Sissy! I can't say no to cock so if you want to participate in my slutty coming out party, please email me for details. Any and all cock will be accepted in my holes! Be sure to follow to watch me turn into a girl!"

I wondered what this coming out party entailed but my fears of getting gangbanged seemed to be materializing. I laid in bed thinking of what was to come and weighing the meaning of the bio Master had written for me. I no longer had an identity. Soon I am just going to be a sissy desperate for cock. I rolled over, my head filled with the thoughts of being surrounded by cock and covered, dripping with cum. I honestly couldn't wait!