Connor reached around from behind me, hugging me deeper into his body as he spooned me. His top hand slid down my stomach to my cock, gently wrapped around it, and squeezed. My cock responded instantly to his touch; I was hard in seconds.
"Get hard and I'll show you," he had just said. My mind was whirling trying to decipher his meaning. After all the boundaries I'd crossed with him in the last 48 hours -- losing my virginity, blowing my load in his mouth, sucking his magnificent cock and swallowing his cum -- there was yet something -- something important, he called it -- that we hadn't done yet?
I groaned as my dick elongated and stiffened. "Ok, I'm hard..." I moaned.
Connor chuckled. "Holy damn, man, it don't take you long, does it?"
"It's your damn fault, Connor," I responded.
He gently placed a few soft kisses on the nape of my neck as he stroked my cock. If it was possible to get even harder, I think I did.
"Turn over," he commanded. "Face me." I did. His hand never left my cock, and he continued to stroke it slowly. "You ready?"
"Ready for what?" I asked. "I have no idea where we're going next, but if it's as good as what we've done, I'm so in." I leaned in and kissed him, hard.
The arm he had under me suddenly lifted me as he rolled backwards. In one swift move, I was on top of him. His arms wrapped around me as we kissed more. He reached for the lube on the nightstand and deftly opened the bottle and spilled a good amount into his hand. I assumed he was going to lube his cock and fuck me, and figured he wanted me to ride on top.
"You gonna lube that up so I can sit on it?" I asked, sluttily.
He shot me a broad, toothy smile as he slipped his hand between us. "Mmm, not exactly." A moment later, his hand closed on...my cock. He spread the lube all over my shaft, slicking me up. A moment later, I felt his legs go up and wrap around my back as he slid my cock down and aimed it at his asshole.
"Connor?" -- the surprise in my voice was matched by the confusion on my face.
"Shhh," he hushed. "Go ahead. Do it."
I looked at him for a long moment, then tentatively pushed forward. He made sure my cock was on target, and the head popped into his chute. I was trembling as I started to enter him, and I thought I was going to cum on the spot.
"Go ahead," he urged, "it's ok, I can take it." I pushed down firmly and slid in about two inches. He grunted and grimaced.
"You ok?" I asked.
"Yeah, yeah, I'm ok," he said, with evident strain in his voice. "C'mon, push it in."
I could tell he was struggling. "Connor, I'm not going to hurt you. Let's go slow." I raised up on my arms, keeping the tip of my cock inside him. "You said it yourself, seven inches isn't small."
"No," he groaned, "it's not. Ok, fuck, you're bigger than I thought," he choked out.
I looked at him skeptically. "Connor, have you...? Have you ever been fucked?"
