Life of a Sissy – Chapter 3

From the Author:
Hi Everyone! This is the next chapter of my ‘Life of a Sissy‘ series. If you haven’t, please read the first two chapters in this series.



I don’t know what to make of the last few weeks. When I think back, it feels like I’ve been living in a dream, or maybe a nightmare. I want it to end, but I want to stay like this forever. I couldn’t imagine a life without Davis.

It was another Sunday afternoon, and it’s been about three weeks since school started, so it’s been about three weeks since Davis had started using me like a sex slave. With him, nothing was off the table. He told me to start growing out the hair on my head, which I was happy to do. When he told me that I had to shave every hair under my eyebrows – not that I even had much in the first place – I did it without hesitation. I even gave him the keys to my house last week, so I can’t even enter my own home without Davis. And sometimes I would wake up with a sore ass or jaw. But on those days, I never woke up without a smile.

“Brian! We’re home!” called a voice from downstairs. I had been so caught up in my daydreaming that I didn’t notice that my parents had come back from another one of their month-long business trips.

“Oh hey mom! Hey dad!” I greeted them as I walked out of my room and down the stairs. I tried to push out any thoughts I had about Davis.

“You didn’t do anything crazy while we were gone, right?” my dad asked with a smile.

I nervously chuckled and struggled to feign a smile. “Nope, same as usual, nothing crazy happened here.”

“New hairstyle, Brian? Why are you growing your hair out like that?” my mom asked.

“Oh, it’s a new trend, everyone at school’s doing it.” I hoped they believed my impromptu lie. I didn’t even realize it grew out that fast. I guess it was just a big difference since they hadn’t seen me in a while.

“Well, it’s great to be home, Brian,” my mom walked up to me and gave me a hug.

This was typical. Whenever they came back from business trips, they seemed pretty happy. Probably because they got to be away from me for a few weeks. I’m pretty sure that they used to think I was some closeted gay. I never had a girlfriend and never seemed to show any interest. Hell, I barely even had any friends. And now… well, I have no damn clue what is going on with me. But I guess it can’t be helped, any parent would be disappointed in an anti-social kid.

Then my phone started ringing. Something my parents rarely witnessed. And of course, it was Davis. I excused myself and went back up the stairs to my room. I picked up the phone.

“Hey, Sasha,” Davis addressed me by my slave name, which seemed so familiar now. “I see your parents are home.”

That always startled me a little bit. I would never get used to the hidden cameras he had placed around my house. I still hadn’t figured out where they were, but then again, I never had much of a chance to, since I was always either being fucked by Davis or passed out – because of Davis. Besides, I wouldn’t want to risk getting him angry by looking for them.

“I guess I can’t come over to your place today then.”

Wait, what? Davis wouldn’t be coming tonight? Davis had come to my house pretty much every day, since we had first met. I should be relieved. I was glad Davis didn’t want to come over and show my parents what I had become. But subconsciously, I knew I couldn’t go without him. He just made me feel full – figuratively and literally.

“You there, bitch?” Uh-oh, David was getting impatient.

“Y-yes, Master, I’m still here. Sorry,” I apologized.

I heard Davis chuckle through the phone. “I’m just messing with you, I know a dumb bitch like you isn’t good for much of anything else besides being a cock sleeve.”

I don’t know why, but this insult made my little dick harden a little.

“Anyways, since we wouldn’t want your parents barging in on our fun, why don’t you come over to my place? I’ll be having a party,” I could hear the wickedness in his voice. But any logic was thrown out the window when Davis invited me over to his house.

“Um, sure thing Master, I’d love to go!” I probably said that too fast, but I couldn’t care less.

“Good, I’m already on your street. Come out in five minutes.” With that, Davis hung up.

Of course. He knew I couldn’t resist. I got up and quickly got dressed. I put on some regular clothes. Jeans and a t-shirt. Davis said it was a party, which meant there would be other people there. Despite what I had done for him, I probably couldn’t handle the humiliation of having anyone else know my secret.

I practically bounced down the stairs, unable to hold in my strange sense of excitement. I found my parents in the kitchen.

“Hey Brian, what’s up?” my mom asked.

“I’m gonna go out for a little bit, I got invited to a party,” I responded.

My parents looked surprised. “Oh, sure, that’s fine! Go ahead! Do you need a ride?” my dad said. He looked pretty excited. This seemed very different than in any movies I’ve seen. Usually, the kid had to beg their parents to let them leave the house, but my parents seemed pretty cool with it.

“Thanks dad, but I have a ride. I’ll try not to be back too late!” I said as I started to leave.

“Don’t worry about it, have fun! Just don’t do anything we wouldn’t want you to do!” my mom called out after me.

Well, that was strange. I thought there would be a lot more opposition from them. However, I have no idea how I’m going to be able to follow my mom’s last command. I’d assume being fucked by Davis was something that they wouldn’t be too fond with.

As I walked out of my house, I saw a van with tinted windows parked on the other side of the street. Because I live in the middle of nowhere, there’s never any cars parked around here except for my family’s. I walked across across the street to the van. In the back of my mind, I knew I was going too far with this. I didn’t even know if this was Davis’ van, but my adrenaline was rushing, and I was so excited that I couldn’t stop myself.

As I walked next to the van, the sliding side door opened, and a person wearing a mask grabbed me. My first instinct was to squirm and run away, but whoever it was that was holding onto me had a tight grip. I felt a cloth covering my mouth and nose. I knew what this was. I had to get out of this. I tried to hold my breath for as long as I could, but I was losing oxygen quickly from struggling to get out of this person’s grip. I gave in and had to take a breath. I struggled for a bit more, then felt the energy leaving my muscles. I quickly collapsed into the hands of my captor. For some sick reason, I was hoping this was Davis. The last thing I remember before falling asleep was my little cock getting rock hard.


“I’m just glad he’s finally out of the house with other people.”

“I know, I was starting to get worried that he wouldn’t ever get any friends.”

“It took this long just to make some friends, I just hope he can keep them.”


“Uh… huh?” I opened my eyes and groggily moaned. Where was I? I tried to look around, but it felt like my head weighed a thousand pounds. Then I realized I couldn’t see anything. Well, I could see, but I was blindfolded. And I couldn’t really feel anything below my neck, I was just numb. Then I remembered what happened. For some reason I wasn’t afraid, I just knew this was all Davis’ doing.

“So, you’re awake, Sasha.” Yep, it was Davis.

“Huh? Wha…?” I tried to speak, but I couldn’t really move my mouth. After spending several seconds trying to talk, I discovered that I had a gag holding my mouth open. It felt like one of the ball gags that I’d seen on porn before. My spit was already starting to dribble down my chin.

“You must be really confused right now. Well, after everything, I think you deserve at least an explanation of what’s happening,” Davis said. I couldn’t really tell where his voice was coming from, it seemed like all the sound I could hear was echoing around. We were definitely in a large room.

I tried to talk to Davis once again, but it just came out as more unintelligible moans, which he ignored.

“That video that you just heard is footage of your parents speaking. Looks like they’re glad you made some friends,” Davis’ remark had an evil tone. “So I guess your parents wouldn’t mind if we hung out for a while.”

So that’s what that was. I found it a bit sad that I was able to recognize Davis’ voice quicker than my own parents’, but they were never home anyways. Davis was really the only person I’d spent any time with in the past month. Even if it was just to be his bitch, I was starting to learn to enjoy the time we spent together.

Wait, was I? What the hell am I thinking? I obviously don’t want to be doing this. I’m only being blackmailed, and there’s nothing I can do about it.

“You’re in my home right now, Sasha. And for security purposes, I won’t be able to take that blindfold off your face. But, that may be a good thing, since I don’t think you would like your identity revealed anyways.”

“Wait what? Is Davis going to get other people to fuck me?” I thought about it for a few moments, and I started to get worried. Then, I relaxed. “No, I should be fine, Davis still cares about me. As long as I’m still with him, I’m fine.”

I wondered why I was so relaxed and open to what was happening.

“Sasha, to make things a bit easier on you and me, I gave you a little drug that just makes you slightly more open to suggestion. But it should wear off soon. If you don’t give me any trouble tonight, I’ll leave you be, but if you decide to get a bit rowdy or rebellious, I won’t hesitate to hit you with it again, alright?”

I just nodded. Of course I did. It wasn’t like I could say no to what he was saying, it was literally impossible. That would explain why I was thinking so strangely. I just have to get through the night without acting out, and I’ll be fine.

“Now that we have the rules laid out, Sasha, I’d like to get started. First we gotta get rid of those ugly clothes,” I felt Davis’ hands on me, lifting me up. I was a bit wobbly, but I was able to stand up. At least I had some feeling returning to my body.

I felt Davis cut my clothes off with a knife and subsequently heard my shredded garments fall to the ground. I followed along and quickly pulled off my shoes and socks. I placed my feet back on the cold, hard ground. Within these first few seconds of being in physical contact with Davis, my little penis already starts to get hard.

“Now I know you’ve been pretty good so far, but I don’t want you to make a mess with my guests tonight.”

“Uh?” I moaned.

I didn’t get a response. Davis just grabbed my arm and pulled me along. I shuffled along after him. I heard Davis open a sliding door and he pushed me outside. I could immediately feel the wind on my naked skin. I shivered because of the cold air. I could tell I was on a patio, due to the painful rocks jutting into my feet. I grimaced with each step as Davis kept pulling me along. I finally stepped onto some grass, and Davis stopped me.

Davis pushed me onto my knees and bent me over. The side of my face was planted on the grass. I felt cold, but I didn’t dare object to what Davis was doing to me.

“Don’t move, Sasha. I’m going to clean you out.”

I didn’t even have time think about what he said before I felt a cold piece of metal roughly inserted into my asshole. I winced and realized what he was doing.

Cold water quickly filled me up. I felt my stomach quickly expand to the large amount of water flowing into me.

“Ahhh…” I moaned in pain, but the sensation of being filled like this was making my little cock throb. Fuck, this was new. The water was so cold and I felt bloated. I started to move my hands back jack myself off, but Davis stopped me.

“Sasha, a good girl only gets to play with her clitty if she is given permission, and I don’t recall allowing you to play with yourself,” David scolded.

I immediately put my hands back down on the grass. Davis pulled the hose out of me and quickly pushed a big buttplug into me. I felt a little uncomfortable, but the buttplug definitely helped me hold the water in. After a few minutes, Davis kicked my legs apart and pulled the buttplug out.

“Push that water out, bitch.”

I immediately did what I was told. It felt strange, having so much water come out of me, but I felt a lot emptier after I did that.

“Let’s just do that one more time. As I said, I don’t want you to make a mess.”

Davis repeated the process once again. The entire time, my little cock was throbbing, but I stayed completely still. When Davis finally pulled the buttplug out of me the second time, I pushed the water out again.

“That looks good enough. Let’s get back inside.”


After Davis had prepared me for the night, he sprayed me down with the hose and brought me inside. The blindfold never came off. He just told me to stay where I was and wait for him to tell me what to do. Then I heard him walk away. I just stayed standing where I was, soaking wet. My arms and legs weren’t bound, and I think the effects of whatever drugs Davis had put on me were wearing off, but I didn’t even try to warm myself up. If Davis didn’t want me to move, then I wouldn’t move.

Suddenly, a hand grabbed my arm. It started pulling me backwards, so I turned around and started walking in the direction I was being pulled. Was this Davis? Maybe this was the first person to fuck me? My softened clitty started to harden once again. This was it. I don’t know if I was excited or scared, but I wasn’t ready.

“Alright, Sasha, stay right here.” It was Davis. He let go of my arm and spun me around a few times. He then put his hand on my chest and pushed me backwards.

My back hit a wall. I fidgeted around for a little bit and realized that I was in a corner.

“Get on your knees,” Davis commanded. I immediately got on my knees. I shivered when I touched the cold ground, but I was glad that I was able to get off my feet.

“Hold your hands behind your back,” came another strict command, to which I immediately followed as well. “You’re going to remain in this position all night unless someone decides to fuck you. Once they’re done, you get right back into the same position where they left you. No cleaning up, no down time. You have to be ready at all times.”

I quickly nodded. I don’t know why I was so eager, but for some reason I just felt like I had to please Davis. Well, I’d been pleasing him for the past month for no reason, so I guess this wasn’t too much different. Davis removed the ball gag from my mouth. I opened and closed my mouth a few times to stretch my sore jaw.

“Well, you look excited. Why don’t I get you warmed up?”

I heard a zipper unzip. Finally. My heart raced. This was the first time today that I would be able to please a cock, and it was Davis’. I eagerly inched closer to Davis and instinctively reached out with my hands to grab his cock. As I reached forward, Davis slapped my hands.

“Keep your hands behind your back unless you’re told, bitch.”

I tried to apologize, but my timid voice cracked since I hadn’t spoken for however many hours it had been.

Then Davis shoved his cock into my mouth. Immediately, I felt full. I could feel Davis’ big, veiny cock pushing against the back of my throat. Saliva dribbled out of the sides of my mouth. I started licking the bottom of his shaft, flicking my tongue side to side, hoping to please him after my previous mistake.

Davis grabbed the back of my head and started pushing his cock further into my throat. My throat opened up more each time his cock thrust into me. Eventually, I was gagging on his cock, which was buried all the way in my throat. Though Davis fucked me like this everyday, I could never get used to how his thick cock filled my throat. I could feel my face turning red as I began to run out of breath.

Davis hadn’t fucked me in a while, so I wanted to savor this moment.

Wait, that must be the drugs affecting me. I don’t want to enjoy this! I want to get out of this!

“You’re gonna have to be able to hold your breath longer than that if you want to get through tonight, Sasha,” Davis scolded.

For some reason, Davis’ command made me focus and try harder to please him. I was able to hold off for what seemed like another minute before Davis pulled his cock out of my throat. Then I felt several long strands of Davis’ warm cum shoot onto my face. As always, I swallowed any of it that landed in my mouth.

Davis wiped his cock on my cheek, then zipped his pants back up. After being exposed to the cold for so long, feeling Davis’ thick, warm cock on my face made me shiver.

“You won’t have to worry about being cold, Sasha, you’re going to be very warm soon enough.”

A few seconds later, I heard the sound of people talking. These must be Davis’ guests. I straightened up and tried to look good for Davis.

“Hey everyone!” Davis welcomed his guests. “Help yourselves to whatever you like!”

“Yo, Dave, who the hell is that?” I heard someone ask.

“This is my special treat to you all.” Davis put his hand on my shoulder. “This is Sasha. Feel free to do whatever the hell you want to her. Just try to avoid any permanent damage.” Davis laughed and walked off.

Just then, music started playing and the party started. Over the probably hundreds of people talking, as well as the music, I didn’t hear someone walk up to me and pull me up to my feet.

“Sasha, huh? Dave got himself a pretty good-looking sissy this time.”

“‘This time’? What was this guy talking about?”

I didn’t really have time to think about what he just said, because I was picked up and spun around, then pushed into the wall. I kept my hands behind my back, as Davis told me, and resisted the urge to get away from whoever this person was.

I felt a finger on my asshole, and I shivered a little bit.

“This is it, I’m gonna get fucked now.”

My little clitty was as hard as it could be. I’d been in anticipation all night, waiting for this moment. I had only done this for Davis before, so having a stranger touch me was a new experience.

“But let’s see if you can perform as well as the others.”

“‘The others’? Am I not Davis’ only sissy?” After thinking about this, I realized I was crazy. Of course I couldn’t be the only one. A guy like Davis could probably fuck whoever he wanted. For some reason, I felt a bit of jealousy.

Whoever was behind started to finger fuck my asshole. It wasn’t long before he got impatient, though. I heard him spit on his cock, then felt him spit on my asshole and rub it around.

He placed his cock on my asshole, then unceremoniously rammed it into me.

“Ugghh!” I moaned. “Fuck!” this guy’s cock wasn’t as long as Davis’, but it was thicker. I wasn’t used to my asshole being stretched like this.

“Oh, you’re pretty fucking tight, Sasha,” the guy whispered in my ear. He grabbed my waist and started slamming into my asshole.

I could feel his thick cock every time he bottomed out and slapped his thighs against my ass cheeks. He gripped my ass hard and continued to plow into my asshole. Then he moved his hands around my stomach and grabbed me. He picked me up and started bouncing me on his cock – this guy was tall. As I bounced on his large cock, I could feel my little clitty flapping up and down.

“Fuck, this guy is good,” I thought. My moaning encouraged the man fucking me and caused him to start fucking me faster.

“Take a look at this bitch!” The guy that was fucking me was showing me off. It seemed that there were people eagerly waiting. I heard remarks from people very close by, then I felt hands reach out to grab and grope me.

I could barely pay attention to what was happening around me, though. I was just focused on the cock that was ramming into my asshole. I was going crazy, I had to cum, and even without any simulation, my little clitty was rock hard. It didn’t seem like anyone was going to help me out, though.

The cock that was in my ass started fucking me harder than it already was, and every time I landed on it, the guy fucking me slapped my ass. Finally, he held me down on his cock and squirted his load inside me.

“Ugh… fuck…” I moaned. I felt so hot and turned on, but I couldn’t cum without using my hands. My little clitty was twitching and my asshole kept clenching around the cock that currently inside me.

I was lifted up off the guy’s cock, then roughly dropped on the floor. I tried to resume my position as soon as possible, on my knees with my hands still behind my back. I didn’t want to disobey Davis, but it was getting hard to resist pleasuring myself with my hands.

The person who had just fucked me said, “Here you go Frank, she’s all yours.”

“Hell yeah, man,” this came from someone else, supposedly Frank, who was already behind me.

Frank picked me up and carried me to a couch, where he dropped me. Frank made me kneel on the couch so that my upper body was leaning over the back of the couch. Frank kicked my legs apart, and it seemed like my asshole was at the height of Frank’s cock. I felt the head of his cock placed at my somewhat stretched hole.

With no hesitation, Frank reamed his cock into my asshole. His cock wasn’t as big as the guy before him, but he was much rougher. In my horny state, I fucked him as well, pushing back against him as hard as I could. I managed to get into a position that perfectly allowed Frank’s cock to hit my prostate every time he bottomed out on me.

While this was happening, someone put their cock into my mouth. I was so focused on trying to get myself off that I barely noticed it. I almost bit down, but I knew I couldn’t displease Davis’ guests.

Frank was bringing to the edge. I felt so close to cumming.

Suddenly, Frank pulled his cock out of my poor asshole. I felt my hole gaping and contracting as my little clitty twitched.

“No! I need more! I’m so fucking close!” I was about to move my hands down from my back to get myself off, but Frank grabbed both of my wrists with one hand.

“Don’t move, bitch!” Frank held me in place.

I tried to fight him, but he was too strong. I felt several thick blasts of cum land on my ass cheeks. Some of it dripped into my asshole and down my twitching clitty. He groaned in pleasure as he held me there for what seemed like forever, but he eventually let go, and I was calmed down.

I was actually glad that Frank held me back from getting myself off, since I probably would’ve been punished if I touched myself.

Fortunately, somebody else quickly took Frank’s place. My asshole was filled again with another cock. Once again, I immediately started fucking them as hard as I could. The person that had his cock in my mouth apparently wasn’t happy with my rapid movements, and they slapped me on the face.

“What’s the rush, bitch? We got all night.”

I slowed down a bit. Luckily, the person that was fucking my ass started to pick up the pace. Once again, my prostate was being stimulated to the point where I was on the edge of cumming.

To my surprise, when the person fucking my ass was about to cum, he grabbed my little clitty. He just squeezed it, but that was enough to make me shoot.

“Mmmph…” I moaned around the thick cock in my mouth. My asshole contracted tightly around the cock in my ass.

I don’t know how much I came, but it felt like that was the most I’d ever cum. I guess the guy fucking my ass was satisfied, too, as I felt him thrust deep into me and cum inside of me. My not-so-tight hole was contracting around his thick cock. At the same time, the person in my mouth seemed to be enjoying my moans, which were vibrating his cock. He grabbed the back of my head and slammed his cock deep into my throat. His thick member was almost too much for me to handle, and tears were starting to form in my blindfolded eyes.

The two people that were spitroasting me pulled away, leaving me bent over on the couch, coming down from the high of orgasm.

I realized how tired I was after I came, and I couldn’t keep my posture. I collapsed on the couch. Usually, Davis only fucked me once or twice in a row, but this was new. This was the longest time I’d been fucked, and I could barely feel my muscles.

“Get up slave,” a voice commanded.

I tried to stand up, by I was too tired. He pulled me to my feet, and before I knew it, I passed out in his arms.


When I came to, I was no longer blindfolded. I was sitting in a metal chair, with my arms tied behind my back. I was still naked, also.

Davis was standing in front of me. My eyes adjusted to the light, but I couldn’t see much anyways, since the room was really dark.

“I’m a bit disappointed, Sasha,” Davis started.

Fuck, I’m screwed.

“I-I’m really s-sorry, Master. I didn’t mean to pass out like that…”

Davis ignored me and continued speaking, “Well, at least the guys still got to use you when you were unconscious. But it did get a little annoying at times.”

“I-I promise it won’t happen a-again…” I whispered, looking at him with pleading eyes.

“Oh I know it won’t. I got something for you so that it doesn’t happen ever again.”

I stared at him, confused and scared. I really didn’t want to pass out like that. I tried my best, but it wasn’t enough.

Davis pulled a cardboard box out of his pocket.

“This right here will make sure of it.”


From the Author:

If you would like to contact me, you can email me at:
james.lot[email protected]