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Wendy's Sister Has Plans

There I stood, dripping wet, looking at the clothes laying on my bed. I was hoping my suspicions were wrong. But, the more I thought about it, the more the dread started to kick in. I was staring at one of my stepsister’s outfits. It was the same outfit I was wearing earlier when I was home alone. But, I was sure that I had put it all away. Then again, this wasn’t the first time I forgotten to put some of her clothes away after wearing them.

Just 30 minutes before that, I had picked out my favorite outfit. It was a pair of pink satin string bikini panties, a white lace bra, black stockings and garter belt, a black silky soft dress that came to my knees, and a pair of black high heels. They felt amazing. I’m not sure how it started but girly clothes always turned me on. I wasn’t happy with just looking at them or even feeling them. I had to be wearing them. Before, my dad and stepmom got together though, my options were really limited to trying some on when I would visit my mom.

After I had finished, I quick jumped in the shower. About 5 minutes into it, I hear my stepsister, Erica, open the door and yell into the shower, “Hey, I’m about to start the laundry. I’m just going to grab your stuff and throw it in.” “Ok”, I responded. My dad was really strict about saving water so we washed all the clothes in the house together. Even with them gone on vacation, it was a habit for us now. 

A few minutes later, I finished up and climbed out of the shower and reached for my towel. But, there was nothing there. I look in the linen closet and there were no towels. This seemed really strange but I figured we must have used them all and forgotten to wash them.

I cracked open the door, stuck out my head and shouted, “Hey Erica! You took my towel too and there are no more towels up here!” In the distance, I hear her yell, “Sorry! I’m down in the laundry room now. Just walk to your room.” Seriously? I can’t believe she’s even suggesting that. It wasn’t that far away, but it was still down the hall and around the corner. “But, I’m naked! I can’t do that!”, I responded. “What the hell, Will!” I’m downstairs. It’s not like I’m going to see you.”, She said.

I stood there debating it for a couple minute but realizing I had no other choice, I swung the door open and ran naked and dripping wet to my bedroom. And that brings us back to the start of the story. Still hoping that I had just forgotten to put them away, I figured I would just put them back later. It was the summer before college and Erica was spending as much time with her friends as she could. So, I knew I’d probably have an opportunity later that evening.

I walk past my bed and open my underwear drawer. All my boxers were gone. Surely I hadn’t run out of boxers. I open my sock drawer. Empty. Now I’m starting to panic. One by one, I open all of my dresser drawers. They’re all completely empty. I knew I was screwed but I checked my closet anyway. It was as empty as my dresser.

She must have been waiting and listening to me shuffle around my room because just as I was looking under my bed to see if some of my dirty clothes were still under there, I heard a knock on my door. “Hey Will. You ok in there?”, Erica asked. 

Without even thinking, I responded, “What the fuck, Erica! Did you take my clothes? I can’t find anything.” 

“Are you sure you don’t have any clothes in there?” She almost sounded like she was about to laugh.

I quickly grabbed her clothes and put them under my pillow. “No.”, I responded.

“I came looking for you to ask what you wanted for dinner earlier. I definitely remember some clothes being on your bed.” I definitely heard her let out a little chuckle this time.

“Ok. But, those aren’t my clothes.” I didn’t know what else to respond. I was desperately thinking of a response to whatever her next question could be.

“Yeah. You’re right.” She said pretty abruptly. “They’re not your clothes. So, do you mind telling me what they are doing in your fucking room?” She was clearly angry now.

“I was about to take a shower and they were in the bathroom. I knew we needed to do laundry, so I quick brought them back to my room so I wouldn’t forget to add them to the load.” It was the best I could come up with. Hopefully she bought it.

“Bullshit! I know you’ve been wearing my clothes, pervert! So, put them on, sissy!” At this point, I could hear her start to turn the door knob. There was nowhere for me to hide. 

As the door swung wide open, I just stood there covering my dick with my hands and shouted, “Get the fuck out! I’m fucking naked!” She completely ignored me and walked into my room. “Seriously, get the fuck out!” I tried one more time.

“Ha! I fucking got you pervert! I was pretty sure you’ve been wearing my clothes but now I know for sure!” She said, with a fire in her eyes. She then began to look around the room. “What did you do with them?” she asked.

“Um. They’re under my pillow.” I responded. It was then that I knew I couldn’t talk my way out of it.

As if she was reading my mind, she asked, “If you weren’t wearing them, then why would you hide them?”

“I, um. I don’t know! I didn’t want you to see them and think the wrong thing.” It was a lame response, and I knew it.

“Oh come on, Will! How stupid do you think I am? You’re a crossdressing pervert and I know it!” She knew she had me. “So here’s what’s going to happen next.” For the first time I noticed a hairdryer in her hand. She reached out and handed it to me. “You’re going to put the outfit on. But, before you do, you need to finish drying off. I’m not giving you anything else you can use to dry off, so use this. And, just so you know, I’m not leaving. So get started. And before you even try to argue with me again, I’ve already created a video of me walking into your room with my clothes on your bed. If you keep arguing with me, I’m going to send it to our parents and I’ll post it online.”

Reluctantly, I took the dryer from her and dried myself off. In one last ditch effort, I said, “Please, Erica. Don’t make me do this. I’m so sorry! It won’t happen again.”

She didn’t say a word. She just pulled out her phone and created a blank text. “Ok ok ok! Please don’t text our parents! I’ll do it.”

She laughed and closed the text. But, she didn’t put her phone away. “Right now.” She said.

My heart began to pound. I moved the pillow and grabbed the clothing. I started with the satin panties, then the stockings and garter. After that, I put on the bra. She had pretty small tits so there wasn’t a lot of space in the cups but there was some. After that, I slipped the dress on over my head and stepped into the heels. Just as I finished dressing, I noticed her taking a bunch of pictures. “What the fuck! Come on! Don’t take pictures… please.”

“Too bad, Wendy.” She laughed as she said the name. “Yeah. That’s the perfect name for you. Now you’re going to do whatever the fuck I want. For starters, you’re doing all the chores from now on. Second, you’re going be dressed like a sissy until our parents get back.”

But, they’re gone for another week and a half! You expect me to wear this for the next 10 days?”

“Well, not just this outfit. You’ll have others.” She said as she grinned.

“You’re going to give me more outfits? Why would you do that?” I asked.

“Oh, no. You’re not wearing my clothes anymore. In a minute, we’re going to have dinner. After that, I’ll put you in a wig and do your makeup if you’d like. But then, we’re going shopping for clothes.”

“No way! I’m not leaving the house like this!” I shouted in a panic.

“You don’t have an option sissy.” She said as she opened the text again. “And, now I really have proof. I didn’t really have the video before. I just figured you’d be too worried to question it.” Just then she looked down and saw the bulge and said, “And, it looks like you’re actually looking forward to it.”

I couldn’t say it at the moment but I really was. Deep down, I was excited.Trying to sound disappointed, I said, “Fine. Let’s just get this over with.”

We both headed downstairs. As we walked past all the other bedrooms, she spoke up and said, “And don’t get any bright ideas about getting into your dad’s room and borrowing his clothes. I’ve locked the door and hidden the key and there’s nothing in the laundry room. And don’t bother looking for your clothes. You’ll never find them.”

I heated up soup for both of us and brought it over to Erica who was already sitting at the table. I sat down across from her and we ate. After about 5 minutes of silence, she spoke up and said, “Obviously, this wasn’t your first time. The way you put on that bra, the way you walked in those heels. Obviously, you’ve done this quite a bit. Listen, don’t bother denying it or lying to me anymore. I don’t care that you’re queer.”

“I’m not gay!” I interrupted.

“So you don’t like men?” She asked.

“No! Not at all!” I said.

“Fine. Sorry. I don’t care that you like to crossdress.I just didn’t like that you were wearing mine and didn’t ask. You just took my stuff.”

“I’m really sorry, Erica.” I said. I knew I was wrong.

“It’s fine. But, you do need to be punished for it so you definitely learn your lesson. Hell, you’re probably going to like it.”

She wasn’t wrong. At this point, we both finished our food and put it in the sink. “You can clean it later, Will. For now, let’s finish getting you ready. Before we do the makeup, you need to do one other thing. Go to the bathroom and get undressed and wait for me.” I did as I was told and a second later she walked back in with a bottle of Nair. “What’s this, I asked?”

“Just lather it all over your body from the neck down.” She said.

“Ok. But what is it?” I asked again.

“It's a hair remover.” She answered.

“Please don’t make me do it.” I begged.

“You don’t have to. But if we go walking into the store and you’re covered in leg and arm hair, everyone will know immediately.” She responded.

She was right. I didn’t have a choice. “Don’t forget your crotch.” She added. I took the bottle and covered myself in the cream and waited. After a few minutes, I felt it tingling. A few minutes later, she told me to jump in the shower and rinse it off. As I did, I was shocked as all of my hair started to just rinse off of my body. I got out and Erica handed me a towel this time. “I already have you and we need to hurry this up. Dry yourself off and lets go to my room.” She said.

It was the weirdest feeling. Everything felt differently but it felt good. As I put the clothes back on, I couldn’t believe it. It was amazing! I thought I was going to cum right there. She could tell I liked it. “I knew you’d like it.” She said. “Ok. Lets go to my room.”

When we got there, she sat down across from me with her makeup kit. It didn’t take long. “Tomorrow, I’m going to teach you to do this yourself.” Next, she put the wig on me with some pins to make sure it didn’t fall off. “I’ve got one more thing for you before we go.” She said as seh walked to her closet. A few seconds later, she walked out with some small breast forms. “Put these in your bra. She had to help me out a little bit, but we got them both in. I couldn’t believe it. It looked natural. With that, she said, “Ok. We’re ready to go.”

Nervously, I walked out with her to the car and got into the passenger side. “What if we see someone we know?” I asked.

“Stop worrying. Nobody will recognize you like this. And if someone asks, I’ll tell them you’re my cousin.”

Having seen myself in the mirror after she finished, she wasn’t wrong. I barely recognized myself.

At every single light, I would get so nervous that someone would see me and know. But, with each light, seeing that nobody even looked over, I got more comfortable. After about 15 minutes, we arrived at the mall. “Alright Wendy! Here we go!”

There didn’t seem to be any point in fighting it. I got out of the car and started to follow. The feeling of the skirt brushing over my legs was amazing. The feeling of the wind blowing up the skirt… I had never felt anything else like it.

“Let’s head to Kohl’s first. They’ll have most of the stuff you’ll need.”

First, we went to the dresses. She picked out a few and handed them to me. Next she grabbed a few pairs of nice pants and then a couple blouses. They were all so pretty. Several things were pink. A few pieces of clothing had flowers. And there was one pink plaid skirt she saw that I couldn’t take my eyes off of. After that, we went over to the lingerie section. “We won’t get everything here, but I know they’re going to have a lot of what you like. You prefer satin panties, don’t you?” She asked. I nodded quickly. We walked through the panties and picked out two 6-packs of satin panties and a pack of satin thongs. Along with that, she grabbed a few pairs of stockings and a garter belt. She obviously knew what I liked.

After that, we headed over to the shoe dept to pick out some new heels and flats. With each pair, she made me put them on and walk up and down the aisle to show her. 

“Ok. Off to the changing room to try the other clothes on.” As the attendant pointed out the stall to go in, Erica said, “Be sure to come out and show me each item. I want to give it the ok.”

I go in and try on the first dress. It’s white knee length flowy dress with flowers all over it. It felt amazing. “Are you ready yet?” I hear from the other side of the door.

I open the door a crack and I hear her say, “Come out. I want to see it.” Aside from the attendant, I noticed one or two other women walk past to their dressing room. “Spin around for me.” By this point, I had no fight left. I was actually really starting to enjoy it. So what if someone saw me.

This continued for the next 30 minutes as I tried on each piece of clothing and showed her. By the time we were done, I was left with three dresses, two pairs of pants, two pairs of jeans, three blouses, a pair of heels, a pair of flats, and a pair of pink girly sneakers.“Ok. Let’s check out. I’ll pay.” She said. Not that there was much choice. I didn’t have the money. But, her dad was pretty loaded and gave her a really big allowance each week. 

“Thanks.” I said. “Time to go home yet?”

“No. We still need to get you some more lingerie. From there, we went over to Victoria’s Secret. We walked around for a few minutes before she started picking out a handful of silky and frilly bras. After that, we went over to the other lingerie and she picked out a few teddies for me to sleep in. They were all soft, pink, and almost see through. She hands me one of the one-piece teddies and says, “Ok. We need to try this one on first to make sure it fits.” As we get to the changing room, she leans in and says, “Don’t forget to tuck it. You don’t want anyone to notice your cock when you come out to show me.” I went in and started to get dressed. It took everything in me to get it tucked so it wasn’t noticeable anymore. I quickly opened the door and said, “Please. Let’s hurry up.I can’t stay like this for long.”

“Ok. It looks good. Get changed and we’ll go. Hand me the teddy when you get it off and I’ll get everything paid for.” I did as she said and by the time I finished redressing, she had everything paid and was starting to walk out the door.

“Are we heading home yet?” I asked.

“Just one more stop. But you can wait in the car.” She answered.

About 5 minutes later, we pulled up to an adult book store. “Just wait here.” She said. Then she disappeared into the store. About 15 minutes later, she walks out holding a couple black plastic bags. They looked full. “You’ll get to see this later.” She said with a mischievous grin. “Time to go home.”

I carried everything in except the bags she got from the toy store. After we got in, she said, “Ok. Go get changed into one of the dresses we picked out. Let me see which is your favorite.”

A few minutes later, I came back down wearing the flowery dress we picked out first. It was so soft and cute. I put on a new pink satin thong and my new heels. I couldn’t believe I had my own girls clothes! It was a rush. I wanted to masturbate right there. Erica must have been reading my mind because just then, I heard her shout, “No jerking off perv! Get dressed and come down.”

I snapped out of it and headed downstairs and sat down on the couch across from her. “Ha! I could see that bulge from across the room! I’m glad I told you not to jerk off.”

I noticed she was sitting with a blanket on her lap. I thought it was odd, but was so caught up in everything else that was going on. Just then, she said, “Ok. Time for your next step stepbro.” and she pulled the blanket off her lap. There she was, sitting with no pants on, just a pair of my favorite pink satin panties with little hearts all over it. “What do you think?” She asked, as she reached down and rubbed her pussy gently through the soft satin.

“Holy shit!” I yelled! I couldn’t believe this was happening!

“You want to touch it, don’t you?” She asked.

“Seriously?!” I asked. I couldn’t believe it.

“Ha! No. Not yet, anyway.” She said as she put her pants back on. Just then, I heard the doorbell. 
“Oh goodie! She’s here!”

“What?! Who’s here?” I asked.

“It’s Sarah. You have to know that I’d tell her. I tell her everything! Now go answer the door.” Other than Erica, Sarah was the only other girl at school that I was really attracted to.

“Please, no!” I begged. “I can’t let her see me like this.”

“She already has, silly!” She responded. “I’ve been sending her pictures all along. Trust me. She won’t say anything. Now go answer the door or other people will find out. I thought we were past this fighting me stage.”

She was right. There was no point in fighting it. So, I went over and answered the door.

“Holy shit!” Sarah shouted. “You weren’t kidding! This is going to be so much fun!”

Just then, I noticed the plastic bags from the adult store sitting out on the sofa. Little did I know that the fun was really about to begin.

So, there I stood in my flowery dress, pink thong, and new high heels in front of Erica and Sarah. My face instantly turned beat red. I felt completely vulnerable. I would’ve rather had them walk in on me naked.

“Holy shit, Erica! I can’t believe your brother is just standing there in front of us in girls clothing!” Sarah exclaimed. “Are you gay?” she asked.

“Holy shit! No! I’m not gay! I don’t know how many times I have to say this.” I said, finding myself getting more and more irritated by that question. But, deep down, I knew that it was a valid question. I mean, I’m  turned on wearing women’s clothes. It only took a moment for me to snap out of it though. I wasn’t gay. I had no interest in guys. I just loved the feeling of girls' clothing on me.

“Ok! You don’t have to freak out. I just don’t know any straight guys who want to wear pink, flowery, girly clothing.” Sarah responded.

“It’s ok.” Erica interjected. “He’s just a little embarrassed. We’ll make her feel comfortable soon. Won’t we Wendy?”

“Don’t call me Wendy!” I shouted.

“Well you have to have a girls name when you’re dressed up. What do you want to be called?” Erica asked.

“I want to be called Will.” I responded immediately.

“Well, that’s not an option. Pick a name or I’m going to keep calling you Wendy.” Erica said sternly.

I shifted around uncomfortably. I didn’t know what name to give her. Then it came to me. “Fine. Chloe. You can call me Chloe, but only when I’m dressed like a girl!”

Sarah and Erica looked at each other, giggled for a moment, then looked back at me. “Chloe! I love it!” They both said and clapped excitedly.

“So Erica, when are you bringing out the other stuff?” Sarah asked while nodding her head towards the black bags.

I had forgotten all about them in the middle of figuring out my new name. My curiosity was piqued.

“Now, actually. OK, Chloe. Don’t forget, you have to do anything and everything I say. That now extends to Sarah as well.” Erica said as she walked towards the bags. She could barely contain her excitement.

She reached into the bags and shuffled stuff around a bit. I could hear the sound of some metals and plastics clinking around. 

“Don’t forget, you still deserved to be punished. You obviously can’t control yourself. I was pretty sure you were wearing my stuff before because there have been way too many times that I’ve seen spots on my clothes that looked like cum. So, we’re going to bring that under control until we can trust you again.” Sarah said with a grin.

Just then, she pulled something out of the bag. I hadn’t seen anything like it before.

“What is that?” I asked.

“They’re anal beads.” Erica said busting out laughing.

“Anal what?!” I asked, completely confused.

“They’re called anal beads. You put them up your ass.” She said.

“I’m not putting anything in my ass!” I shouted.

“Um, you say that like you have a choice. Besides, we’ll start with the smaller beads and I’ve got lube. You’re going to like it. Trust me.” Erica said.

“She’s right.” Sarah interjected. “Now come over to the couch, kneel down, and bend over the couch.”

She then grabbed the beads from Erica and started rubbing lube all over them. I closed my eyes. I was so nervous but couldn’t think of any way out of it. Just then, I felt her hand grab the edge of my thong, pulling it out of my ass. I tensed up.

“Just relax.” Sarah said softly in my ear. A moment later, I felt the first bead touch the rim of my hole. She held it there for a second and started to slowly apply pressure. I felt the first bead go in. I never felt anything like it. I couldn’t believe it. It sent a shock through my whole body. Moments later, I felt the next bead and the next bead and the next bead. With each growing bead, I got a new shock. It felt amazing.

“I think he likes it.” said Erica. “Keep going.”

She continued to push more and more. I started to lose count of how many beads were in my ass. But I couldn’t help but want more.

“Holy shit!” Sarah exclaimed. “You’re right. He does. Chloe, lay down on the couch and lift your legs in the air.”

Without hesitation, I got up off the floor, laid down on the couch, and lifted my legs as she commanded.

Sarah had a huge grin on her face. She got down on her knees and grabbed the beads again. “You’re about three quarters of the way, Chloe. Let’s keep pushing.”

Just then, I felt another bead go in. I could feel they were starting to get big, like almost the thickness of my cock. Then the next bead went in. It was starting to get a little uncomfortable but only until the bead was fully in. Next thing I knew, I felt her finger, which was hooked to the ring at the end touch my ass. The combination of knowing it was all the way in and feeling the finger of such a hot girl touch my ass while dressed as a girl was almost more than I could bear. My cock was throbbing in my panties.

“I think he’s ready for the next step.” Erica said, as she walked over holding something new. It looked kind of like a microphone. As she got close, she pushed a button and it began to make a loud vibrating noise.

Sarah resumed playing with the beads, pulling them out just slightly and pushing them back in.

“Yeah, he’s not going to last much longer.” Sarah said to Erica. They both laughed.

“You’re going to really enjoy this, Chloe. Every girl needs to feel a vibrator on her clit.” Erica said as she kneeled down next to Sarah.

She barely touched my perineum and I jumped a little. I was really caught off guard. But, it only took a moment before I calmed down. She put it against my perineum again and started to rub it around softly. It was the most incredible feeling. I could feel it from my ass, in my balls, and all the way through my cock. Slowly, she started to move it closer and closer to my clock and the feeling just kept getting more intense. I wasn’t sure how much longer I would last.

Moments later, the vibrator reached my cock and I couldn’t help but let out a loud moan. Both of them looked at each other and giggled. “He really likes it! Keep going!” Sarah said.

Just then, I felt it. I was reaching the point of no return. “Oh shit! I’m going to cum!”

“Open your mouth.” Sarah said.

I didn’t even think. I just did what she said. No sooner had I gotten my mouth open when I felt it happen. My cock constricted and cum came squirting out harder than I had ever cummed before. It actually reached my face and a little bit got in my mouth. That was when I realized why Sarah wanted me to open my mouth.

My cum was everywhere. It went from the bottom part of my dress all the way up to my hair. I couldn’t believe what just happened. It was the best orgasm I ever had.

Moments after I stopped cumming so much, I felt Sarah’s hand run over my dress. “Open up, Chloe.” She said.

Again, I responded without thinking. A second later, I saw her hand reach towards my mouth. As she reached the edge of my mouth, I realized what she was doing but it was too late to try and stop her. Her hand was covered with my cum that she wiped up off of my dress. “You better swallow it! Don’t spit it out!” Erica commanded.

It tasted strange. It was a little salty. But, oddly enough, I actually liked it. And I couldn’t hide it either. I let out a loud “Mmmm!” At this point, it was pointless being embarrassed. I could see them both smiling and quietly giggling. I reached down, wiped more cum onto my hand, and put it in my mouth. Needless to say, I swallowed again.

It was only a second later when I felt one more shock. Without any warning, Sarah grabbed the anal beads and ripped them out. I jumped and they both started laughing hysterically.

“Go clean yourself up and get dressed in this.” Erica said as she handed me this cute, silky, pink nightie. “When you’re done, come to my room. We’re going to have a sleepover.”

“Yeah, but don’t expect anything else to happen tonight, Chloe.” Sarah said. “You’re going to need your rest for tomorrow.”

They both laughed. I was nervous but excited about what was to come.