“Did I hurt you?” I asked, praying I hadn’t.
“No,” he said, a wide smile on his face. “You’re doing just fine. Try again.”
This time my fingers breached him, and he hissed. I watched his expression. He wasn’t in pain, I knew that, so I didn’t stop. I did as he had and pushed in slightly.
“Oh God,” he groaned. “Go deeper.”
I pressed in until my fingers were buried to the second knuckle. He let me explore, moving my fingers in different ways to see if it heightened his pleasure at all. Before I realized it, my fingers were all the way inside of him.
“Do you feel that bump?” he asked. “That’s my prostate. If you touch it lightly, it feels so goddamn good.”
I searched for it, and when I brushed against it, Charlie groaned.
“Fuck yes!” he cried, his hips pushing off the bed. “Add another finger now.”
There was no hesitation this time. Seeing the look of rapture on his face had me willing to do anything he wanted. I quickly spread a little more lube and slowly pressed the fingers into his opening. Watching them sink in was fascinating. He let me go at my own pace, but I noticed his head rocking back and forth as his hips canted.
“Matt, I need you now. Do you think you’re ready?” he asked, his voice pleading.
“I…. Maybe?”
He opened his eyes. “Baby, it’s okay if you’re not. I swear, I won’t be upset or angry. I think what you did today is amazing.”
“No, I want to, but…. Would you be hurt if I used the condom?”
He chuckled as he sat up and stroked my arm. “No, not at all. I only showed you the report so you knew. If we decide one day to go bareback, then we do. It’s not a deal breaker, I promise.”
My hands trembled slightly as I reached for the box of condoms Mr. Gianetti had sent me long ago. I pulled one out, tore the foil wrapper slowly, and rolled the condom down my length. My every thought focused on what we were about to do.
Charlie smiled when I put a little bit of lube onto the condom. “You’re learning,” he said, obviously pleased.
“Good teacher,” I mumbled, wanting to distract myself from the erotic haze I found myself enveloped in.
“Kneel between my legs,” he said, pulling them up.
After I’d positioned myself where he wanted me, he smiled. “Okay, here’s the deal. You’re quite a bit thicker than three fingers, and it’s been a long time, so I’d appreciate it if you go slow so I have time to adjust to having you in me. Okay?”
I did my best to focus on my target. My cock throbbed so hard I feared it would burst. After scooting forward a little, I took my shaft in my hand and positioned it at his opening. “Are you sure?” I asked.
“Very” came the reply. “I’ve been wanting this for a year, but if you need more time, then we’ll take it.”
“No, I’m okay,” I promised, though every nerve in my body was set to high. I put my hands on his legs as I pushed in, just a little. I made sure to keep checking his expression, needing to ensure I wasn’t hurting him. As soon as the head of my cock breached his hole, this incredible pressure surrounded it. I immediately stopped, because the sensations were damned overwhelming. My teeth sank into my lower lip, the small bite of pain giving me something to think about.
“Matt? Are you okay?” Charlie asked.
I nodded. I could feel warmth trailing down my cheeks. I knew I was crying yet again.
“You can push in some more.”
I shook my head, unable to move.
“Baby, what’s wrong?” he asked me, rubbing my arms.
“I’m going to come,” I said, embarrassed that it would be over any moment. “I can’t make it good for you.”
He gave me a warm smile. “Come if you want. You’ve already made it better for me. To know that I’m your first and, just so you know, your only? That’s pretty goddamn heady. If you come now, then we try again later. There’s nothing to be embarrassed or ashamed of.”
Without replying, I pushed in a little deeper. Charlie groaned, his head thrown back and mouth open. I couldn’t believe the heat that flowed around me. I had to bury myself all the way. It became my focal point. Slowly I pressed in a little deeper, each inch burning me up from the heat in his body. When I found myself unable to move any more, I realized I was fully seated inside Charlie. He squeezed his ass muscles, and I groaned at the combination of heat and tightness.
