Life of a Sissy

My name is Brian. 16 years ago, I was born a male. Now I am 5’3″, skinny, and wish I was a girl. I’m not transgender, but I wish I was. I have a small penis and a high voice. At school, people have often mistaken me for a girl, then give me weird looks when I tell them my true gender. Usually they would think I was a girl trying to be a boy, but really, it was the other way around. I would do anything to be a girl.

I woke up to my radio alarm blaring at me. I looked over at the clock to see ‘7:31 AM’ written in a bright red font. I set the alarm for 7:00, but I’m a really heavy sleeper, so this happens a lot.

“Crap, I’m gonna be late on the first day of school,” I muttered to myself. School starts at 8:00, so I only had about half an hour to shower, get changed, eat breakfast, and walk to school.

I’d like to be able to take the bus to school, but I live way out in the middle of nowhere, so there isn’t a bus stop anywhere near me. Also, my parents are never home, since they’re always out on business trips, so I have no one to drive me. I followed my usual morning routine and then left the house. I do have to admit, even though I can’t socialize and have no friends, I’m always excited on the first day of school. Seeing new faces and meeting my teachers.

My first class of the day was math. My worst subject. I looked around the class to see a lot of people eyeing me.

“He looks more like a girl than I remember,” someone whispered, followed by muffled laughter.

I noticed one kid in the back who I’d never seen before. Probably new to the school. He was sitting down, but I could tell he was really big and tall, someone that would fit the description of ‘Captain of the Football Team’. The seat next to him was empty, and he kindly gestured at it. Seeing as it seemed no one else wanted me to sit with them, I took up on his offer.

“I’m Davis, nice to meet you,” he said, extending his hand.

“Same here, I’m Brian,” I shyly responded, accepting his hand shake. He probably didn’t mean to, but it felt like that hand shake broke every bone in my hand. This guy was definitely strong.

When class started, I noticed that Davis’ hand slowly inched toward my thigh. My face turned red, and I couldn’t focus, but he seemed perfectly fine, being able to listen as the teacher introduced himself and explained to us what we were going to be doing throughout the school year. By the time the class had ended, Davis’ big hand was completely wrapped around my thigh. I couldn’t bring myself to say anything, but I noticed my penis was rock hard from his hand being so close.

At lunch, Davis found me and invited me to his table. There were a couple of other people there that I knew. As I suspected, most of them did sports for the school. Davis already knew these people well, laughing and joking with them. I was completely ignored though, except for Davis’ hand on my thigh once again.

I didn’t have any more classes with Davis, but I couldn’t focus the whole day because of him. When school ended, I left my last class and began heading towards the exit. When I walked out the door, I saw Davis standing outside, looking at his phone. I didn’t know if I should say anything, so I just walked past him. When I walked past the parking lot, I heard Davis call my name.

“Hey, Brian, you’re walking home?” He asked.

“Yeah, I can’t drive yet, and I live too far away from anything to ride the bus,” I answered.

“Then I’ll give you a lift,” he offered.

I know I shouldn’t get into a stranger’s car, and even if I sort of knew who he was, I still felt a bit uncomfortable. But I did hate walking home. I was already so tired, and Davis seemed nice enough, despite what he did today.

“Ok, thanks,” I responded quietly.

We walked over to his car, and it was really nice. A bright red Mercedes. He looked at me, saw my surprised face, and laughed. Davis got in the car, and I sat down in the passenger side. It was very clean.

“Watch this,” Davis said. He pressed a button on the dashboard and the roof of the car started reclining.

“Wow, I’ve never been in such a nice car,” I whispered, amazed.

Davis smiled and drove out of the parking lot. I gave him the directions to my house and he sped off. He drove recklessly through traffic, ignoring the stop signs and speed limits. Davis treated the car like as if it wasn’t even his, but I couldn’t care less. My heart was racing. It really felt like I was invincible. And I almost didn’t notice that Davis’ right hand was wrapped around my leg once again.

In just a couple minutes, Davis was pulling into my driveway.

“You’re parents aren’t home?” He asked.

“No, they’re always away on business trips and stuff,” I answered.

“Cool. Can I use the bathroom while I’m here?”

“Yeah, go ahead.”

I took my keys out of my backpack and opened the front door. I walked in, and Davis followed, closing the door behind him. I told him where the bathroom was, and he walked off. I sat down at my living room table. I took a book out of my backpack and opened it up to start reading. It was another book in my favorite fantasy series. I loved fantasy books. I could escape into another world while sitting in one place. For a while, I could just forget about the real world.

Being so focused on my book, I didn’t notice Davis walking into the room.

“Hey Brian,” he started. I jumped a little, forgetting that he was still in my house.

“Yeah, Davis?”

“Can I use your laptop for a little bit?” He asked while pointing at a laptop that was on the other side of the table.

“Uh, yeah, sure.” I walked over to the laptop and opened it. I typed in my password and watched the screen blink on. I sat back down to read my book.

After some typing, Davis kept looking back and forth from me to the computer screen. Then he nodded.

“You’ll do,” he whispered.

“Hm?” I asked, not quite able to hear what he said.

Without responding, Davis walked over behind me and took the book out of my hands, then slid it to the middle of the table. I instinctively stood up and bent over the table, reaching for the book. Then I felt Davis’ hands grab my hips.

Davis pushed the chair out of the way and stood right behind me. I was no longer trying to reach for my book, but I was completely still, afraid of what was going to happen.

I was about to ask Davis what he was doing, but when I opened my mouth, his big hand covered my mouth.

“Shh… Don’t worry about it. We’re gonna have some fun,” Davis whispered soothingly.

Davis leaned over to grab the laptop. He turned it around to show me that he had a porn site opened up. Being a lonely dork like myself, seeing anything porn related had my little penis hard. Then I looked at the video that was opened. It was a boy wearing a black skirt and a matching black bra, bent over a table. Behind him was a big, buff guy.

Davis didn’t say anything, but just unbuttoned my jeans and slid them down to my knees. My boxers followed suit. Davis looked at my pale ass and gave it a smack. Then he reached under me and grabbed my little cock, which was rock hard at this point. Davis squeezed my cock just a little, and I don’t know what came over me, but I moaned and came in his hand immediately.

“Someone’s a bit excited, I see,” Davis leaned over and whispered in my ear.

I was going to say something, but his hand covered my mouth again. This was the hand that was covered in my cum.

“Lick your juice off my hand and swallow it. I want you to swallow all of your cum.”

I was so afraid and turned on at the same time that I couldn’t resist. I licked Davis’ hand clean. I held my cum in my mouth. Obviously I’ve jacked off before, but I’ve never gone as far as tasting or even swallowing my own cum. There wasn’t much, but the salty taste was pretty strong. When Davis removed his hand, the cum was replaced by my saliva.

“From now on, whenever we’re alone or whenever I tell you, you aren’t male. You’re a girl, and your name is Sasha.”

In a way, my wish had come true. I did say I would do anything to be a girl. I guess this was it. Even after I had just cum, my cock was getting hard again thinking about what would happen.

“You couldn’t look more like a girl, you know that? You have such a nice big fucking ass. If you just grew out your hair a little, and maybe got some bigger tits. Has anyone ever touched your asshole before, Sasha?”

“N-no…” I whispered.

“Oh fuck yeah. And I’m gonna be the first to put my big cock inside your tight little asshole.”

I was trembling. I know I did just cum, but I didn’t want to. I couldn’t let this guy take control of me. “Stop! You can’t just do what you want!” I yelled at him. My voice cracked. I tried to stand up, but his hand just pushed down on my back, forcing me back onto the table.

Davis laughed. “You don’t really mean that, do you? Besides, it’s a bit too late for that now. Let’s just get this started.”

Davis unpaused the video on the laptop. The big guy standing behind the sissy opened up the zipper hole in his jeans and stuck his big cock through it. Davis did the same. Davis kept going, doing exactly what the guy in the video was doing. Davis rested his big cock on my crack.

“You’re a bit dry, Sasha,” Davis said. He reached his hand around my face again. It was the same hand that had my dried saliva on it from when I ate my cum off it. “Spit on my hand so I can get nice and lubed up.”

With the pressure of Davis’ warm cock pressing up against my ass crack, I spit on his hand. He moved his hand back and rubbed my spit on his big cock.

“And I guess since it’s your first time, I warm you up. Just suck on my fingers a little.” Davis moved his hand in front of my face again. He stuck out his index, middle, and ring finger and forced them into my mouth. “Be a good girl and get my fingers nice and wet.”

Davis’ three fingers were probably thicker than my own penis, and I had some trouble fitting them in my mouth. When his fingers were deep in my mouth, I bit down hard. He immediately pulled them out.

“Fuck you!” I yelled.

“You fucking bitch!” Davis yelled back. “You really think you can fight back against me? I was going to go easy on you, warm you up first, but I guess I’ll have to teach you the hard way.”

Davis lined up his cock with my asshole. He pointed at the video. The big guy was already fucking the sissy deep in her ass.

“I’m gonna fuck you ten times harder than that.” Davis growled.

I had goosebumps now I was so scared. “No! Please! I’ll do anything, just don’t fuck me! Please!” I was shaking, and I tried to moving my body around.

“You had your chance. And you know how much you really want this. I guess I just have to bring out the slut in you.”

With that, Davis grabbed my hips to hold my ass still. Then he rammed his cock all the way into my ass.

“NO!” I screamed. I kept pushing away from him, but the pain was too great. Davis let go of my hips and grabbed my throat. He pulled me back so that my back was arched.

Davis started thrusting his cock into me, and through the pain, I started feeling a little bit of pleasure. The way he was fucking me, it seemed his cock was ramming into my prostate every time he thrust into me. Davis tightened his grip on my throat just a little more, so that I wasn’t getting enough air to be able to resist, but I was still conscious enough to feel his big thick cock filling up my asshole.

Davis showed no signs of slowing, and I came again. When I came, my asshole contracted around Davis’ cock, only pushing him to fuck me harder. I could feel the head of his cock pushing deeper and deeper into me with every thrust. I could feel every vein on his cock along the walls of my tight hole. I could see that the video on my laptop had already ended, but Davis was still going strong.

Davis continued fucking me, and the pain in my ass was starting to get replaced by pleasure.

Davis was grunting like an animal every time he thrust into me. My moans were reaching higher and higher pitches.

“This asshole is mine, Sasha. Your whole body belongs to me, bitch,” Davis grunted.

At this point, Davis let go of my throat and wrapped his hands around my stomach. With his cock still thrusting in me, he lifted me up and started bouncing me up and down on his cock. One of his hands moved down and squeezed my little penis, causing me to cum again.

“Does your little clitty like it when I destroy your asshole? Huh?”

I nodded my head up and down vigorously. “Yes, my little clitty loves it!” I moaned.

“That’s right, slut.”

After what seemed like forever, Davis dropped me on his cock and pushed deeper into me than he had before. He shot a huge load inside of me.

This sudden change caused me to cum again, shooting just a few drops of cum. I could feel Davis’ load filling me up. It was so warm and smooth in my asshole. Davis dropped me back on the table. I was almost sad that it had ended. But I wasn’t sad for much longer, because quickly passed out from exhaustion afterwards.


When I woke up, I was still on the table, with my ass sticking up, cum dripping out of my asshole. I was completely naked. I groaned and pushed myself up. I slid off the table and dripped some of Davis’ cum on the floor. My floor was completely covered in cum, sweat, and saliva. My mouth was a bit sore, and that’s when I realized I couldn’t stop smiling. That was the greatest thing that had ever happened to me.

My laptop was still open, and the video Davis showed me was still on the screen. Everything seemed to be left untouched, for the most part. I did notice a little sticky note on the table, though.

“I took the liberty of getting your phone number. If you ever get any phone calls or texts from me, you must answer, or else.”

I wanted to regret what I did, but I couldn’t help it, it was just so good. I wanted more.

I grabbed my phone, wanting to say something to Davis. I didn’t know what, but I just wanted to talk to him. He was the only person that gave me any attention. I know it’s really strange, but I feel like we have some sort of fucked up friendship.

I realized that I didn’t have Davis’ number, but I didn’t need it. It seems he had already texted me.

Over 20 pictures of me from different angles, unconscious, on my living room table. The cum dripping out of my asshole, my naked body. He made sure to get my face in the pictures, too.

The last thing he sent me was a video. It was in a slightly lower resolution, but you could still tell it was me.

“How did I not notice him recording me? I should’ve seen his phone,” I thought to myself.

I looked over to where his phone would’ve been. My laptop. It has a webcam. And it was facing right at me. Davis was good. Then I got a call. Davis.

“I see you’re awake, Sasha.”

“Y-yes… how did you know?”

“I think you’ve already noticed, but I recorded us from your laptop’s camera. I’m pretty good with cameras and tech. Wherever you go, I can see you. From now on, you’re going to do whatever I say, whenever I say it, got that?”

“Y-yeah, I g-got it Davis,” I whispered.

“No, no more Davis. Call me ‘Master’ when we’re in private.”

“O-ok, Master.”

“Good girl. I think we’re gonna have a lot of fun together.”


From the Author:
This is my first time writing here, hopefully you enjoyed it!
If you have any feedback or want to speak with me, email me:
[email protected]

Thanks for reading!