The First Time I Bottomed for a Twink
I posted part 1 of me topping this twink last week so if you didn’t read that go check it out if you’re interested!
A few weeks went by and James and I continued our relationship. Topping was pretty new to me and, as much as I enjoyed it, I really wanted to bottom. So one night I invited him over, told him I wanted to bottom, and he agreed.
James was bottom vers, but hadn’t actually topped before. He was a little nervous, but was excited to pleasure me. He had me lie on my stomach and placed both hands on my ass. He spread my cheeks apart and his tongue brushed over my hole. My muscles spasmed at the sensation and I let out a slight moan. This got a chuckle out of James and he smacked my cheek, hard. I flinched, buried my head in the pillows, and whimpered. He kept eating my hole and I was in complete bliss.
He kissed his way up my body, from my ass to my neck, sending shivers of pleasure through me. His kisses trailed up my neck and to my ear and whispered, “Get on your knees and suck my cock.”
I rolled over and he took my place. James lay on his back, hands behind his head. He looked so cocky and smug. This was a totally different side of James that I hadn’t seen before, but I liked how dominant he was acting. I got between his legs and kissed his thighs, his balls, and ran my tongue up his shaft to his head. I slapped it against my tongue and took him into my mouth. I was deep throating him when he grabbed the back of my head and began thrusting into my mouth. My eyes watered, but I stayed there like a good boy, letting him use my mouth however he wanted. He released the back of my head and I gasped for air, tears sliding down my cheeks.
“Come up here,” he said, patting his lap. I wiped my face on the back of my hand and sat in his lap. He got the lube and spread some on my hole and his cock. “Are you ready?” I nodded, anticipating a slow start. James’ had a six inch cock, but was particularly thick, especially his shaft beneath the head.
Suddenly, a wave of pain blasted through me as he slammed his entire cock into me. I gasped in complete shock. Pain radiated through my entire core and we stayed like that as it began to fade and my breathing became more steady. I opened my eyes and looked down at James. He was looking up at me with a smug look on his face. My hand shot out, grabbed his face, and I whispered “Don’t you ever fucking do that again.”
James didn’t say anything back. I grabbed both of his hands and pinned them over his head by the wrists. Once the pain faded, I slowly slid up and down his cock. He said, “Keep going, that feels amazing.” He bit his lower lip and moaned. I sped up and he matched my speed, thrusting up into me. His eyes were closed and I could tell he was close to finishing. Suddenly, I lifted up off of him and his eyes shot open. “Why did you stop?”
“I waited so long for this. You’re not finishing that quickly,” I responded. I released his hands and slid off of him. He motioned for me to lie on my back.
He grabbed me by the back of the knees and pushed my legs back, my hole exposed to him. I grabbed my legs and he released them. His fingers found my hole, his other hand on his cock. He pressed into me and reclaimed hold on my legs. He began taking deep, long thrusts into me and I was moaning immediately.
“I can’t hold out any longer. Your ass feels too good,” he said. He leaned down and kissed me. James sped up, pounding my ass until he came, flooding me with his huge load. He leaned back, with his cock still in me, and wrapped his hand around mine. He stroked my cock and I rocked my hips down onto his in time with his hand until I shot my load, coating my stomach and chest.