Life of a Sissy – Chapter 2

From The Author:
This is a continuation of my ‘Life of a Sissy‘ series.
If you haven’t, please read the first chapter which is called ‘Life of a Sissy‘.

I hope you enjoy!


I woke up to my phone ringing.


I rushed to check it. Of course. Davis. And two missed calls from him as well.

“H-hello… Master?” I answered quietly.

“Well, hello there, sleepyhead.” Luckily, Davis didn’t sound angry, but I didn’t know him well enough to tell.

“I’m s-sorry I didn’t answer your calls before, Master. I’m a really heavy sleeper…” I trailed off, not knowing what else to say.

“I know, I could see that you were actually asleep. It’s alright today, since it’s only the first time, but I’m going to fix that soon enough. See you in a little bit.”

“O-ok Master,” I responded. Davis hung up. I sighed. I was terrified. What was Davis going to do to me?

I realized that my cock was hard once again. Even just hearing his voice made me so turned on. I’m not gay, but I just couldn’t stop thinking about what Davis did to me yesterday.

I shook those thoughts out of my head and got ready for school.


I walked into my first class of the day, math. Davis was there, watching me with a smile. Like yesterday, I sat down right next to him. He didn’t say or do anything to me, but I was pretty nervous the whole class.

Davis noticed me shaking in my chair. I was unable to look at him.

“You ok?” Davis asked this completely normally. He put his hand on my thigh once again. “Calm down,” he said soothingly.

I nodded and was able to stop shaking, and with his hand on my thigh, I somehow felt more relaxed. The class went by like yesterday. There wasn’t really much work, since it was only the second day of school.

Towards the end of the class, Davis got up to sharpen his pencil. He spent a few seconds at the electric sharpener, then walked back. When he sat down, he was grinning evilly.

“What did he do?” I wondered.

Just a couple seconds before the bell rang, the pencil sharpener that Davis used made a buzzing noise, then sparked and burned out. The container holding the pencil shavings then popped out and fell to the floor, getting pencil shavings everywhere. Then the bell rang.

Several people who were already leaving the classroom looked over at the sharpener, then turned back around to leave the room.

“Woah, that’s weird,” Davis remarked completely innocently. By now, everyone had left the classroom except Davis and me.

When I tried to stand up, Davis grabbed my hand and pulled me back down.

Davis walked up to our teacher’s desk. “Hey, Mr. Henderson, maybe Brian and I could help you clean up that mess over there?” He gestured over at the broken pencil sharpener.

“Sure, that would be great, thanks!” Mr. Henderson replied. Then he return to looking at his laptop.

Davis walked back over to me and pulled me up. He walked over to the closet and got out a broom. He handed it to me and told me to clean up the shavings on the floor. I immediately obeyed and started sweeping. Davis picked up the pencil sharpener and pulled something out of it, then put it in his bag. He examined the sharpener for a little bit, then put it down.

“Mr. H, the sharpener is broken, it’ll have to be replaced,” Davis told our teacher.

I had finished sweeping up the mess. What was Davis trying to do?

“Sure thing, Davis, thanks for helping clean up,” Mr. Henderson replied, without looking up from his laptop screen.

“Could we get late passes to our next class, Mr. H?” Davis asked.

Our teacher just nodded his head. We took two passes then left the classroom. I started heading to my next class, but Davis pulled me in the opposite direction. I knew better than to question him, so I just stayed quiet and followed him.

Davis walked up to a janitor’s closet, then looked around. When he confirmed that no one was around, he opened the door and gestured for me to come in. I hesitantly stepped into the room.

“Well, we have passes, so we can spare some time before going to our next class,” Davis said.

I gulped.

“Now get over here and strip, bitch!” Davis commanded.

“Y-yes master…” I replied. I walked in front of him and took my clothes off quickly.

Davis grabbed me and turned me around, so my back was right up against his big body. I got a good look at the room we were in. It was pretty dark, only lit up by a light hanging from the ceiling. There were all sorts of cleaning supplies in the room. Everything was really dusty, which was strange and a bit ironic. It seemed like this room hadn’t been used in a long time.

“Let’s have some fun, Sasha,” Davis emphasized my slave name, reminding me who I was.

I stood still as he unzipped his pants and dropped them. My back was still facing him, so I couldn’t see, but I knew what was coming. Then I felt the tip of Davis’ big cock pressing right in between my ass cheeks. Davis chuckled a little. I didn’t want this to happen, but I couldn’t forget the last time he fucked me. It felt so good, and I wanted him to do it again. My little cock was getting hard.

I heard Davis spit on his hand, then him rubbing his cock, using his spit as lube.

Finally, Davis put his hands under my armpits and picked me up. He brought me closer to him so that my back was touching his chest. The tip of Davis’ big cock was now right under my little asshole.

“Do you want me to put my big cock in your little asshole, Sasha?” Davis whispered in my ear.

I bit my lip. I didn’t want to do this. I knew it was wrong, but I couldn’t say no.

“Well, Sasha, it doesn’t matter what you want. You belong to me now.”

With that, Davis dropped me right onto his big cock.

I half moaned, half screamed. His big cock was filling me once again. His cock felt so deep. It hurt me, but the pain was quickly covered up as Davis wasted no time in wrapping his big arms around my stomach and bouncing me up and down on his cock. Every time he lifted me up so only the tip of his cock was inside me, then dropped me back down. My pleasure was increasing. In doing this, he was ramming my prostate every time he slammed into me. After just a few thrusts, I came.

Davis grabbed my sensitive tip, causing me to moan. “Is this little slut enjoying herself?”

“Ohh… fuck fuck fuck” I moaned. I couldn’t bring myself to say real words. Davis was still fucking me hard. My asshole was contracting around his cock, pleasuring him more and making him fuck me faster.

“Who do you belong to, bitch?” Davis whispered in my ear.

“Y-you Master, I belong to you Master!” I screamed. I didn’t even know what I was saying. Master just asked me a question, and I answered. That was what a good slave was supposed to do.

I continued to bounce on Master’s cock, and without realizing it, I came again. Once again, my asshole contracted around Master’s cock. This time, I made him cum, too.

“Oh, fuck yeah.” Master dropped me on his big cock and held me there. He shot his load deep into my asshole.

“Th-thank you, Master,” I whispered, “I hope I did a good job.”

“Yeah, you were a good little slave, Sasha,” Master told me. Then he lifted me off his cock and put me on the floor.

I curled into a ball. I felt so happy that I was able to please Master. I felt so good. I was drifting off to sleep when I felt a slap on my face.

“Get up, bitch, your job isn’t done yet.”

I got up on my knees. I was a bit wobbly, since I was starting to feel a little pain in my stretched asshole, but I was still feeling so good that it didn’t matter.

Master pointed his cock at me. “You gotta clean me up. We still have to go to class after this.”

I knew what he meant. “B-but Master, I’ve never sucked a-a…” I trailed off, because he was glaring at me.

“Well you better learn how. If you don’t… I’ll never fuck you again.”

I looked at him, shocked. For a moment, I woke up from my trance. What the hell was I doing? Everything that just happened in the past couple of minutes felt really hazy, and it felt like I wasn’t in control of myself. Obviously I didn’t want Davis to fuck me again, that was a really weird threat for him to make.

I didn’t know what took over me, but I grabbed his cock and put it as deep into my mouth as it could go.

“What the hell is wrong with me?” I thought. But I didn’t stop.

I had watched porn before, so I remembered what the girls would do and I tried to copy what they did. I looked up at Davis and saw that he was smiling. I guess I was doing a good job. I wrapped my lips around my teeth and kept my mouth wide open so I wouldn’t bite him. I just kept moving my mouth up and down on his cock. I could taste his cum mixed with my ass juices, which was a pretty salty, but a little sweet.

I bobbed my head back and forth until the tip of Davis’ cock hit my throat. I couldn’t push it any further, or my gag reflex would kick in.

Suddenly, Davis grabbed the back of my head and slammed his cock all the way into my throat.

I choked and my face turned red. I couldn’t breathe, but I was really good at holding my breath, so that didn’t matter. I was just really surprised. I kept choking on Davis’ cock while his hands held onto my head. Spit was coming out the sides of my mouth. I put my hands on Davis’ thighs, trying to push myself away, but Davis held onto me strong.

I looked up at him, pleading with my eyes, but he was just smiling down at me. My jaw was starting to hurt, and my eyes were watering. I tried to tell him to let me go, but anything I said was muffled by Davis’ big cock.

After what seemed like forever, Davis let go of my head. I pulled back, gagging and coughing.

“A bitch like you should be able to take it in the throat easily,” Davis scolded.

“Y-yes… Master,” I said in between coughs.

“Well, whenever I call you, you better answer right away, or I’ll do that to you again. Oh, and by the way, this janitor’s closet isn’t being used anymore, so expect we’ll be spending a lot of… quality time together in here.” Davis smirked and put his clothes back on, then left the room.

I looked at my phone and saw that it was already 15 minutes into the next class. Even with a pass, teachers didn’t like it if I was too late. I quickly cleaned up and put my clothes on then left the janitor’s closet. I ran into a bathroom to quickly wash my face, then headed to my class.

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