Forced to Jerk in Panties: Sissy JOI Phone Sex

I had just come home from a long day at school, and I was ready to relax. As I walked into my bedroom, I saw something that made my eyes widen. There, on my bed, was my little brother, Tyler, wearing one of my dresses rubbing his cock on the outside of his boxers. I couldn’t believe what I was seeing.

“Tyler!” I squealed, “What are you doing?”

He jumped, startled, and quickly pulled the dress down, trying to hide his embarrassment. “I-I’m sorry, Emersyn,” he stammered. “I was just… I don’t know. I was curious.”

I raised an eyebrow, a wicked smile playing on my lips. “Curious, huh? Well, little brother, I think we can arrange something.”

Tyler looked at me, his face flushed with embarrassment. “What do you mean?”

I walked over to him, my heels clicking on the floor. “I mean, I think it’s time for you to learn a few lessons about respecting other people’s property.” I sat down on the bed next to him, my dress riding up slightly to reveal my thighs.  “I think you should start by dressing up for me every day after school.”

Tyler’s eyes widened in surprise. “What? No way, Emersyn. I can’t do that.” I leaned in closer,   to whisper “Oh, but you can, Tyler. And if you don’t, I’ll tell Mom and Dad about your little cross-dressing habit.” 

He hesitated, clearly torn between his embarrassment and his desire to keep his secret. “Fine,” he finally said, “I’ll do it.” I smiled, “Good boy. And not only will you dress up, but you’ll also jerk off in front of me. Every day.”

Tyler’s eyes widened in shock once again. “That’s too far, No, I’m doing that!”

I moved around to his other ear, my lips touching him “Oh, but you can, Tyler. And if you’re a good boy, I might even let you touch me.” He swallowed hard, his Adam’s apple bobbing in his throat. “Fine,” he said, his voice barely audible. “I’ll do it.”  And so, our little game began. Every day after school, Tyler would come home and dress up in my clothes, and then he would jerk off in front of me. I found it so exciting and hot to watch my little brother pleasure himself dressed up in pretty pink clothes.

One day, as he was stroking his cock, I couldn’t help but reach out and touch it. He gasped, his hips jerking slightly at my touch. “Emersyn,” he said, his voice filled with desire. “You’re not supposed to touch me.” 

I smiled, my fingers wrapping around his length. “Who says I have to follow the rules?” I asked.

 Tyler moaned, his hips moving in time with my hand. “Fuck, Emersyn,” he said. “That feels so good.” I stroked him faster, my hand moving up and down his length. “You like that, don’t you, Tyler?” I asked. I smiled, my hand moving even faster. “Good boy,” I said, my voice filled with approval. “Now cum for me, Tyler. Cum all over my hand.”

Tyler groaned, his hips moving faster. “Fuck, Emersyn I’m gonna cum.”

I felt his cock pulse in my hand, and then he started squirting cum, his hot seed spilling onto my hand. I stroked him through his orgasm, milking every last drop from him. As he came down from his high, I looked at him, a wicked smile playing on my lips. “You know what, Tyler?” I said “I think it’s my turn now.” He looked at me, his eyes filled with surprise. “Your turn for what?”

I smiled, a wicked glint in my eye. “For you to make me cum.”

Tyler hesitated, clearly uncertain. “But I don’t know how,” he said, his voice filled with embarrassment.

I laughed, my hand reaching out to touch his cheek. “Don’t worry, baby brother,” I said, my voice filled with affection. “I’ll teach you everything you need to know.”

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