tagTransgender & CrossdressersPunished in Step Sister's Clothes

Punished in Step Sister's Clothes

bygenericusername96©

Editor's note: this story contains scenes of incest or incest content.

*****

Growing up with a step sibling is weird when you didn't meet them until so far along in life. That's how it was with me and my step sister, Haley. We first met when we were both early on in our teen years and by then our personalities were already forming: she was preppy and bitchy while I liked to keep to myself. Our parents quickly moved in together and she and I were forced to spend a lot of time together.

We all got along well usually except I always felt awkward around Haley. She was always dismissive of me if not straight up rude and was fairly messy. She would just leave her laundry everywhere, including her panties and bras. That's what started it all, really. My interest in what it would be like to wear girls' clothes. She just left them laying there and I just would get curious and try some on.

By the time both of us were 18 we were still living at home while attending college. Now that we were older our parents were gone nearly all the time and the house was left to us. Haley got lazier and, in addition to not cleaning up her laundry, she would barely wear anything. She would prance around the house in a long shirt that barely covered her plump, curvaceous ass and her nipples would regularly poke out of the cloth covering her small, yet sexy, boobs.

There were a few times where I would keep a pair of her panties after cleaning up all her dirty clothes or borrowed a tube of lipstick to see how the shade would look upon my lips. Her panties would hug my dick and squeezed my ass, making it look like I had the ass of a sexy girl when looking in the mirror, but it wasn't enough. I wanted more.

It was a day when everybody would be out of the house and I could really go into her room and raid it. She barely payed attention to anything and wouldn't notice a few pieces of clothes go missing; after all, she had so many. I entered her room and began to dig my way through things until I made my way to her closet. I opened the door up and saw a menagerie of sexy clothes hanging there. She had corsets, dresses, bikinis, skirts, tube tops, and all other clothes. I ran my hand over some of the fabrics and decided to go with a matching set of black, red, and lacey bra and underwear. After that I picked out a dress that I thought looked cute: it was a beautiful, simple white dress. I took the clothes into my room and stripped off everything I had. I slid the panties up my legs and smiled when I felt them hug my hips and my soft dick. Even though my ass didn't look nearly as nice as Haley's I liked to imagine that people would stare at mine like I stare at hers. After that I adorned the bra and checked myself out in the hallway mirror. Damn, I looked good. The bra was loose since Haley has more boobs than I do, even if it isn't by a huge portion.

A voice from behind me said, "Oh my god, what are you doing!" I turned around quickly to see Haley standing there, staring dead at me. She began to walk towards me and I froze like a deer in headlights. She shoved me against the mirror before shouting, "Those are my clothes why the fuck are you wearing them!" I tried to stutter out an answer, but she cut my off by slapping me in the face. My face stung from the slap and as I looked at her with my face searing red from the embarrassment her eyes widened. I felt my dick pressing against the panties, trying to burst free. I could see the anger boil up inside of her.

I quickly said, "Please, I'll do whatever you say! Just don't tell anybody! This was just a one time thing!" I tried to press my boner down and do what I could to hide it but nothing worked.

"You are a fucking pervert!" She shouted as she came over and grabbed me by the arm. She started to pull me into her room and when we got in there she told me to go sit on her bed. "This is not okay. I am so fucking pissed off at you. That's my favorite set you're wearing! And why are you getting hard from this!" She turned around out of frustration.

She was wearing leggings today and they really hugged her ass nicely. The way her butt made it seem like the fabric would tear was just divine. I could tell that she was wearing pink underwear today. Things weren't too bad, after all, she's just yelling at me. So maybe she actually was happy to see me get a hard on. I could play this to my advantage. "Well maybe if you stopped strutting around looking so slutty and leaving your underwear everywhere I wouldn't have done it. Plus, you don't seem that angry to see me." When I finished that line I placed my arms behind me on the bed and spread my legs so she could see how hard I was.

Haley turned around and I saw a vessel pop. She turned around for a second, took a deep breath, and turned around quickly. Before I knew it I saw she had her phone out and I heard the snap of her phone's camera. "Now you listen here you fucking pervert. I just got a picture of you in your 'full glory' and sent it to my second account on SnapChat. I will destroy you if you don't listen to me. Forget just my Dad and your Mom seeing this. Everybody will see it. You think I like slutty? I'll fucking show you slutty." She walked over to me and slapped me across the face again before moving over to a box hidden in her closet. She pulled out a razor and some shaving cream. "You are going to go into the bathroom and shave all the body hair off of you. Then come back out, completely naked."

I walked into the bathroom and started to do as she said. Shaving my arms and legs was easy, but when it came to my privates I just felt dirty. Rubbing the shaving cream all over my crotch and slowly shaving away the hair started to make me feel vulnerable. After that I started to shave my ass. It was tricky to accomplish. My entire body felt smooth like brand new silk. Now that my body was naked of all hair I returned to Haley, and each step filled me with a combination of humiliation and pleasure.

Once I reentered her room I saw clothes laid out on her bed. There was a small red thong next to a black bra and beside that was a white tube top and a black skirt. While I stood their naked in front of Haley she laughed before snapping another picture. "I can't believe my step brother is such a pervert. I want to you put those clothes on after you prove to me you shaved everything like I told you to." I went over to where she was sitting and slowly spun in a circle. "Not bad, but lift up your arms above your head and hold them there. I want to make sure you shaved your pits." I did as she commanded and raised my arms. She approached me and ran her hand down my raised arms to my chest before pinching one of my nipples. I let out a girly moan and she continued to play with my chest. Her fingers pressed together with my nipple in between them and pleasurable pain shot through my body. I could feel my dick jumping every time she pinched me. After a moment of that she stepped away. "What a fucking wimp. Okay, now let's make sure you shaved your butt enough." I turned around and stared at the wall. "Spread those cheeks, show me you really tried." I placed one hand on each of my butt cheeks and spread them apart as wide as I could. She laughed some more and I felt her slap my ass once, twice, and then a third time. After that she told me I was okay to put the clothes on.

I slid the thong up my legs and felt the string go straight between my cheeks. It was hard to keep my dick contained within the tiny crotch area, but I managed to. Next I put on the bra, which wasn't nearly as loose as the one I tried on earlier. The frame of the cups sat nicely on my body and the band really hugged my chest. If I were a cup size or two bigger it would probably fit perfectly. After that I slip on the skirt, if it could really qualify as that. Once it was hugging my waste it didn't even feel like it was covering my ass. It felt like it was covering half at most. Lastly, I put the tube top on and that's when she led me out to the mirror. While my face was still clearly masculine, the rest of me did look slutty. The skirt barely covered my ass and if I moved at all it shifted to reveal half my ass from the back and my entire hard on from the front. The tube top's white color made it so you could see through the fabric to my black bra, and it just happens to fit well enough to give the allusion of me having really tiny boobs. Haley grabbed my ass and my boob and started to fondle me. "You look like so slutty right now, like you're just waiting to take some big dick in all of your holes." Her words started to turn me on more while her fingers dug into my ass and her other hand massaged my tit. I accidently let out a feminine moan.

"I'm not gay and are we done yet?" I squeaked. Haley looked at me with a devious smile, let me back into her room, and told me to sit down in the chair in front of her makeup studio. She rummaged through some of the drawers and pulled out a needle and some hoop earrings. I stood up, "No way am I getting my ears pierced. That is too far!"

"Shut up and sit down! Either I am piercing your ears and putting these hoop ear rings in there or I'm gonna pull out my vibrator and make you feel like a real fucking faggot! But hey, maybe you'd like that. You are dressed like a slut after all!"

The thought of my step sister having my bent over her bed with her sliding her vibrator in and out of my ass seemed like a great idea. The thought of her fucking my ass until I couldn't help but explode didn't seem too bad for a single instant. But that'd be gay! And I'm not gay. I quickly discarded the thought, "I'm not gay! You can't make me do either of those things!"

She set down her needle and earrings and took a drink of some water she had laying around. "You're right. That is too far. Here, take a drink. I'm sorry." She handed me the other bottle of water. I felt like this was her way of having an apology toast. We tapped bottles and chugged the water. After a few seconds I started to feel light headed and dizzy. I fell back onto her bed. She climbed on top of me and for a split second I was able to feel her tights grind up against my dick. Haley whispered into my ear, "When you wake up you're gonna look like such a slut that you're gonna look in the mirror and wish you could just fuck yourself in the ass. I won't have a step brother. I will have a slut sister."

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bygenericusername96© 13 comments/ 50253 views/ 44 favorites
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by Anonymous

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Um, you stopped in the middle.

Yep. Right there in the middle. So, clearly, this is Punished in Step Sister's Clothes Ch.01. I am looking forward to Punished in Step Sister's Clothes Ch.02.

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by Anonymous06/18/19

Construction please

Will he be chaned to a slutty little sister again guy's hold on and let fuck him.

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by Mamut2206/07/19

Quickly next chapter

Such a hot story pls more

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by Anonymous03/18/19

Moreeeee

Moree I had a sissygasam to this story hope he wakes up locked and plugged

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by cdCindy103/14/19

please continue

Love this story but I myself don't need to be drugged to crossdress. I love sucking cock too and also getting fucked. I can't wait to read what she does next to sissy.

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