Chapter 1

Okay, so, like, when I was 15, I totally started borrowing my older sister’s clothes. Just trying them on, you know? It was kinda sneaky, but I’d always hide them in the laundry basket if my room got cleaned.

My sister’s three years older, and our mom worked, like, all the time – 9 to 7, sometimes even later. When I turned 18, Mom moved out to be with her boyfriend, leaving the house to me and my sis.

So, there I was, 18, living with my sister. I was in college, and she worked retail. I’d get home around 3 or 4, and since she didn’t finish work until 5 (plus a half-hour drive), I had time to raid her closet and, like, have my own little fashion shows.

Then, when I was 18 and working as an IT apprentice (short hours, so I finished around the same time as before), my sister got a better sales job and met her boyfriend, Kevin.

He was, like, a total car and sports guy, and I was a computer geek who loved video games. We were so different, but we were still nice to each other.

Kevin was a mechanic and always seemed to be on call. I didn’t really get his job, but he didn’t really get mine either, so whatever. It got harder to, like, do my thing with my sister’s clothes.

Regular stuff wasn’t cutting it anymore. So, I bought a dildo online. It was, like, amazing at first, but then I wanted more.

I’d sit on my computer on the landing (our rooms were too small for desks), with the dildo… you know. Sometimes, when I was playing games or watching videos, I’d, like, move around a bit.

My sister and Kevin just thought I was excited about something. But, like, the idea of getting caught was kinda thrilling.

I bought a vibrator, too, and used it the same way. One time, when I was using it at my desk, my sister walked by. “Hey… what’s that vibrating?” she asked. OMG! I totally panicked.

“No idea, think it might be my computer,” I said. She gave me this look, like, she didn’t believe me. “It’s never sounded like that before… it’s usually quiet,” she said.

I was, like, about to… you know, so I had to think fast. “I downloaded some new game mods, and I think they’re messing with my computer. I’m getting rid of them anyway,” I said. Luckily, she bought it and left. I totally… finished right then and there. It was so intense!

After that, I kept thinking about all the crazy stuff I could do, like wearing her heels or, like, bending over in front of her with a plug. The next day, I got home and my sister had left a note saying she’d be back late.

Score! I had, like, two whole hours to myself. I totally raided her closet again. It was so much fun trying on all her different outfits!

Then, I heard the front door open and Kevin’s voice. OMG! I freaked out and shoved everything back in the drawers.

I was wearing a black cocktail dress and heels! I hid under my sister’s bed. Kevin came into the room and started talking to himself. Then he went on his phone.

After, like, forever, my sister came home. Kevin went downstairs to talk to her. That was my chance! I snuck out from under the bed and ran to my room, still in the dress!

My heart was pounding. I changed back into my normal clothes and then walked onto the landing. Kevin saw me! “Where were you?!” he asked. I lied and said I was napping. He seemed suspicious, but he let it go.

A few weeks later, I still hadn’t put the dress back. My sister left another note saying she was working late. Yay! I had, like, four hours. I did my makeup, hair, the whole thing, and put on the dress and a wig. I was, like, totally rocking it! Then, the postman knocked.

I had to answer the door! I kept my mouth shut so he wouldn’t hear my voice. He just needed a signature for a package. I totally nailed it!

Then, when I was taking a selfie, I heard a voice behind me. “Well, this is interesting.” It was Kevin! OMG! He looked shocked but also kinda amused. He took a picture of me! I was so dead. I begged him not to tell anyone.

He just shrugged and then, like, unbuckled his pants. He told me to… you know. I was, like, totally not into that, especially with my sister’s boyfriend! But he threatened to show everyone the pictures. So, I… did it. It was so gross! Then, he took another picture of me after.

I took a shower and went back to my room. Kevin was there, with all my stuff on my bed. He said I owed him one for keeping my secret.

He said if I didn’t do what he wanted, he’d show my sister the pictures. I was so trapped! This is so crazy!


Chapter 2


Ugh, things were SO bad.

I couldn’t sleep at all. Turns out, he’d already posted those pictures online! Like, everyone knew my secret. I was freaking out.

I had to stop him, but seeing him almost three times a week was torture. I just kept my head down at work and at home, trying not to set him off. I did NOT want a repeat of… well, you know.

Then, my sister comes home all happy, telling me how Kevin “really appreciates” me helping him. I was so confused! Turns out, he’d told her I was going to help him clean his mom’s house on Friday! Without even asking me! I was like, “When was I supposed to have agreed to this?!” Two hours later, Kevin shows up, and I go straight for him. “When were you planning on telling me I’m busy Friday?” He just laughs and says he “forgot” to mention it was for “volunteering” to clean his mom’s house for her birthday. So rude! I told him I wasn’t doing it, that I clean up enough of his messes already.

He just smirked and pulled out his phone, saying he might post more pictures of me on Twitter or Facebook. Seriously?! I caved. “Fine. Where is the house?” He was all smiles then, saying he’d pick me up. And then he had the nerve to pat my butt! I was so nervous about Friday.

Friday night, I was a nervous wreck. Waiting for something bad is the worst. My sister and Kevin came in, she said bye, and he whispered “play time” in my ear. Shivers. We drove to his mom’s house, which was in the middle of nowhere. I seriously thought he was going to, like, murder me.

The house was a mess – dirty clothes, stains everywhere, old food… gross! Then, he throws a pile of clothes at me. It was a French maid outfit! I was like, “What the heck?!” He told me to put it on and get to work. I knew I had to play along.

The outfit was SO revealing – all lace and basically nothing underneath. I looked in the mirror, and even though I hated it, I have to admit, I looked kinda good. I went downstairs and started cleaning. Kevin hadn’t moved from the sofa. Jerk. After an hour of cleaning, I was exhausted.

He comes in, eating an apple with his mouth open, pieces flying everywhere. “Whatcha doin’?” he asks. I said I was taking a break. He kneels down next to me and says I have 30 minutes to finish the rest of the house, or “puppy gets punished.” shudders.

I finished downstairs and went upstairs. His mom’s room was a disaster, and the bathroom was even worse. Then, I went into what I thought was his room. It smelled awful. Under the bed, I found a box with a heart on it. Inside were red panties, a camera, and a note that said, “Don’t forget about this.” I looked at the pictures on the camera and realized they were of my sister! Her face was covered, but it was her. I freaked out and found a used condom too! Eww!

Kevin came in. “Well?” he said. I was confused. “What?” He said I had a time limit and I’d failed. I told him the house was way better than before, and he just said, “Tut tut tut, follow me.” He grabbed my arms from behind and put something on them. Handcuffs! He took me to the living room and sat me in a chair.

Then, he yelled, “He’s here!” A tall Black man and a pretty blonde girl came in. I was SO embarrassed, sitting there in that outfit, basically naked, in front of strangers. The girl whispered something to the man and giggled at me.

Kevin came back with a bag that was making clinking noises. The Black guy, Blake, told the girl, Cindy, to grab something. She pulled out a pink… egg. I knew exactly where that was going.

She gave it to Blake, who put it… you know… inside me. Kevin turned it on, and it started vibrating. I tried not to react, but then Cindy started touching me… down there. I couldn’t help it. I started getting… you know.

Then, Kevin pulled out a paddle and started hitting my butt! It hurt SO bad. Cindy put a ball gag in my mouth so I couldn’t scream. Then, she went back to… you know… with Blake.

Kevin finally stopped hitting me and threw me on the floor. Blake made me… you know… and Cindy… you know… at the same time. It was… intense. I even… you know… myself. After they left, Kevin unlocked the handcuffs.

I got dressed, and then my sister and Kevin’s mom came over to see the “hard work” we’d done. Kevin took all the credit, even though he’d done nothing!

My sister and I went home, and I just lay in bed for hours, thinking. I was so confused. I hated what happened, but part of me… kinda liked it? I know Kevin’s a jerk, and the fact that it was him and my sister’s boyfriend made me feel sick.

But I need to get those pictures back, or I’m going to be his slave forever. I need a plan. And I need help. I can’t tell my family, so I’m hoping my best friend can help me.

by Lexi

Categorized in:

Sissy Blackmail Stories,

Last Update: December 24, 2024