I crept into bed and straddled his hips, taking his unresisting hands and placing them on the full curve of my breasts. “Wake up, love. I want to try something new today.” Barely waking, drowsy and pliable, he smiled that wonderful smile and caressed my sides, his palms moving ever downward. He brushed against the leather straps across my hips, and came a little more awake. “What are you wearing?” When I showed him, his eyes widened, and for a moment he tried to push me off him.
But I pushed back, and as his wrists, firmly gripped in my fingers, fell back against the pillows, he remembered that he loved being my toy. To use as I please, even… even like this? No, this was too much. He couldn’t. “Baby, you know I love you, but I can’t take that, not in… not in me.”
“It’s ok, sweetness, I understand. We’ll start a little slower, then, get you used to it. Get out of bed and get on your knees.”
He hadn’t expected that. But surely it would be easier, right? And less humiliating than having a silicone cock shoved up his… he got on his knees in front of me, usually such a comfortable position for him, and lowered his head. I let him set the pace at first, but he hesitated with his lips wrapped around the head of my strap on, and could go no further. So I pressed upward with my hips, and slid the length of it into his throat.
He went along with it for a moment, but when it hit the back of his throat he gagged and pulled back. Looking up at me, there was something approaching fear in his eyes. “I can’t do this.”
“I’m hearing a lot of ‘can’t’ out of you this morning, my love. You have two choices. This is one of them.”
He closed his eyes and drew in a long breath, sighing it out of his nostrils. “Be nice to me, ok?” I smiled and nodded, and pulled myself back on the bed, relaxing back against the pillows, one hand reaching for him. He looked confused at the position I’d chosen, and I couldn’t help grinning as I made it clear.
“I want to watch you ride my cock, pretty boy. Don’t worry, it’ll actually feel better this way.”
It took him a minute to work up the courage. But he is a good boy, and so he knelt over me, placed the head of the strap on against his asshole, and pressed himself down. Gently at first, but he was tight and tense, and he had to strain to push me inside of him. He gasped once, loud, when I finally penetrated him, clearly it hurt. But, brave pet, he kept going, and when he had taken me fully inside him, when the head of my cock was rocking against that sweet spot again and again, he moaned. He moved faster, circling his hips to vary the pressure, and soon enough his head fell back and he rode me, hard and fast, lost in the pleasure of my cock deep in his ass.
He did well, for his first time. But it was his first time, and so it was over in just a couple of minutes. He had taken all he could, and the pleasure was starting to feel overwhelming. So I pulled him down against my chest and with my cock still inside him, we rolled to our sides, facing each other. He was panting, and he winced when I moved, but that smile was back on his lips. And as I petted him, and kissed him, and he slipped back into a dreamy doze, he whispered, so low I could barely hear him.