Blackmailing my best friend's stepbrother

My best friend Sarah and I had been planning this prank for weeks. Her stepbrother Mark was so arrogant, always walking around like he owned the place, making snide comments about our clothes and our “girly” interests. Today was our chance to get some payback.

Sarah was in the shower, and I was supposed to be keeping watch while she planted a pair of her lacy panties in Mark’s underwear drawer. The plan was simple: later, we’d “accidentally” find them and tease him mercilessly about wearing women’s underwear.

“Coast is clear,” I whispered as Sarah tiptoed out of the bathroom, a mischievous grin on her face. She crept toward Mark’s room with me following close behind.

Mark’s room was exactly what you’d expect from a cocky jock—posters of half-naked women on the walls, clothes scattered everywhere, and that distinct guy smell of sweat and cheap cologne.

Sarah carefully pulled open his underwear drawer. “Okay, time for phase one,” she whispered, reaching in with the panties.

But then she froze. “Wait a minute,” she said, her eyes widening. “What’s this?”

I leaned in closer. Tucked away at the back of the drawer, partially hidden by a stack of boxers, was something that made both of us gasp. It was a sleek black prostate toy, curved in that distinctive shape. And next to it? A large, realistic-looking dildo that was at least eight inches long.

We stared at each other in shock. Mark, the ultimate ladies’ man who was always bragging about his conquests, had sex toys hidden in his underwear drawer.

“Oh my god,” I breathed, feeling a strange mix of shock and excitement. “I never would have guessed.”

Sarah reached in and picked up the dildo, examining it with wide eyes. “This explains so much,” she said. “Remember how he never brings girls home, even though he’s always talking about them?”

“And how defensive he gets when anyone questions his masculinity?” I added.

We were so absorbed in our discovery that we didn’t hear the shower stop running. Suddenly, the bathroom door opened, and Sarah’s stepbrother Mark stood there in just a towel, his hair dripping water onto his shoulders.

“What the hell are you doing in my room?” he demanded, his face turning pale when he saw what Sarah was holding.

Sarah dropped the dildo as if it burned her. “I…. we were just…” she stammered.

Mark’s expression shifted from anger to pure panic. He rushed over and slammed the drawer shut. “Get out!” he yelled, his voice cracking.

But instead of leaving, I found myself speaking. “We’re not going to tell anyone,” I said softly, “but we want something in return.”

Mark looked at me, then at Sarah, his eyes filled with fear and humiliation. “What do you want?” he asked cautiously.

Sarah stepped forward, a mischievous glint in her eyes. “We want to use these on you,” she said, pointing to the drawer. “In exchange for our silence.”

Mark’s jaw dropped. “You can’t be serious.”

“Oh, we’re very serious,” I said, stepping closer to him. “Either we use these toys on you, or we tell everyone at school what we found. Your choice.”

He stood there for a moment, his mind racing. Finally, he nodded slowly. “Fine,” he whispered. “But you have to promise not to tell anyone.”

“We promise,” Sarah said, already reaching for the drawer again.

Mark lay down on his bed, his towel still wrapped around his waist. Sarah and I exchanged a look of excitement as we pulled out the prostate toy and the large dildo.

“First, lose the towel,” I commanded.

Mark hesitated for a moment before slowly unwrapping the towel, revealing his semi-erect cock. Sarah and I both stared, surprised by his size.

“Not bad,” Sarah commented, causing Mark to blush.

I picked up the prostate toy and coated it with lubricant from Mark’s nightstand. “Roll over,” I instructed.

Mark did as he was told, revealing his tight ass. I slowly inserted the toy, causing him to gasp. Sarah watched, her hand already moving between her legs.

“How does that feel?” I asked, moving the toy in and out.

“Strange… but good,” Mark admitted, his voice strained with pleasure.

Sarah picked up the large dildo and positioned it at Mark’s entrance. “Ready for round two?” she asked with a wicked smile.

Mark nodded, bracing himself. Sarah slowly pushed the dildo inside him, causing him to moan loudly. I watched in fascination as his body responded to the stimulation, his cock growing harder with each thrust.

“Touch yourself,” I commanded.

Mark reached down and began stroking his cock in rhythm with Sarah’s movements. The room filled with the sounds of his moans and the wet sounds of the dildo moving in and out of his ass.

“I’m going to cum,” he gasped after a few minutes.

“Not yet,” Sarah said, pulling out the dildo. “We’re not done with you.”

She replaced the dildo with her fingers, finding his prostate and massaging it expertly. Mark writhed on the bed, completely at our mercy.

“Please,” he begged, “let me cum.”

I leaned down and whispered in his ear, “Beg for it.”

“Please, please let me cum,” he pleaded, his body trembling with need.

Sarah and I exchanged a look, then nodded simultaneously. “Cum for us,” I said.

With a loud cry, Mark exploded, covering his stomach and chest with streams of cum. Sarah and I watched in satisfaction as he came down from his high, his body still trembling.

But we weren’t finished yet. As Mark lay there panting, Sarah dipped her fingers into the warm cum pooling on his chest. “One last thing,” she said with a wicked grin.

Before Mark could react, Sarah smeared the cum across his face, marking him with his own release. I joined in, using my fingers to spread the sticky fluid over his cheeks and forehead. Mark flinched but didn’t resist, his eyes wide with a mixture of shock and submission.

“Now you’re properly marked,” I said, admiring our handiwork.

As we cleaned up, Mark looked at us with a mix of shame and gratitude. “Thank you,” he whispered, his face still glistening with his own cum.

“Don’t mention it,” I said with a wink. “But remember, this is our little secret. Things will be different if you want us to keep it.”

Mark nodded, already looking forward to our next “encounter.” And as Sarah and I left his room, I knew our relationship with Mark had changed forever.