Cheaters Never Prosper - Sex Stories

Cheaters Never Prosper

... to cover his hands since there was nothing we could do with them today. Sitting there, I ran my fingers through his hair to fluff it up a little and give it a bit more body, finally leaning back to admire how pretty he was standing there with me. His bright blue eyes were on me as I rose suddenly so I towered over him, my hands falling to his shoulders. "Ok, Jamie," I said, smiling at his new name. "It's time to earn my favor back and we can see about maybe getting you a passing grade eventually." With my fingers curled around his shoulders, I pushed him down to his knees before he knew what was happening. There was something erotic and taboo about seeing him there all dolled up on his knees, the confused look on his face as he stared at my crotch for a moment. "I don't understand," he said, his voice almost a whisper. He looked up at me with wide eyes and a terrified expression but I know it was fear of accepting what was in his heart. I'd seen enough to know he wanted to wear the clothes in his writing and doodling but was afraid of what it meant. He wouldn't have to fear now, just trust in me and let me lead him to the right place. With a quick motion of my arm, I slid my hand into his hair and pulled his head back as I leaned down towards him, my eyes blazing as I stared at him. "You don't need to understand, my little slut," he growled, a feral smile on my lips. "You'll do what I tell you and make sure you do your best or you can say goodbye to your life and your ...

... future. There's a video camera in the closet that just captured you eagerly putting on girls' clothing, how do you think that will make your senior year go here?" Holding his hair in one hand, I reached down and unzipped my fly slowly, the sound of the metal against metal loud in the quiet room. Then, I reached in and hauled my half hard cock through the flap in the boxers and let the cool air wash over it as I brought it full you for the young sissy to enjoy. Despite himself, his eyes were staring at it with a mix of dread and fascination, it was probably the first adult cock he'd gotten to see live and up close. Wrapping my fingers around the base, I pulled the k**s face close to me until I could smack the head against his cheeks and lips, smiling at his uncertainty. "Kiss the head," I commanded. "Lick it like you want to, Jamie. Make it all wet and shiny with your mouth like you know you want to, sweetie." I placed the tip at his pink lips so the fluid leaking from the slit would smear over them, giving him a good first taste of what was to come. Looking up at me and then my member, he puckered his lips and kissed the tip and around the bulbous head. Then, he parted his lips and licked under the head before swirling it around the sensitive head. His breath blew over me as I enjoyed the first ministrations of the boy, watching the curious look in his eyes as he tasted and experienced a man for the first time. He didn't look disgusted when he swallowed down his first taste of the ...