Caught with My Stepsister's Clothes Pt. 02

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.

End of part 2