I slid on the condom. My erection wilted slightly — partly because it always did when I first put the slippery latex prophylactic on — but it was also partly because of nerves. Sure, Leo enjoyed it when I fingered him, but a dick felt a lot different to fingers, and I didn’t want him to hate it.
“Tell me to stop at any time,” I told him as I squirted lube onto my hand and slicked myself up. I warmed up some more and gently rubbed it against his entrance. “You can change your mind at any time.”
“I know,” Leo said.
“It’s going to hurt,” I warned him.
He gave me a wry smile, and I knew I’d said something completely obvious, but he didn’t seem as worried as I expected. Maybe it was because he was still stroking himself.
“I know,” he repeated. “But it’s okay. I want this. And —” he said before I could interrupt. “I’ll tell you if I need you to stop.”
I nodded. I took my time stretching him out with my fingers — maybe too long because Leo knocked my arm with his knee and told me to put it in. I moved closer, holding his hips, our skin flushed. Slowly, I eased myself in.
Leo stilled, his face tightening, and I stopped. “Are you okay?”
“Fine,” he said. “Keep going.”
I did, and when I was about halfway in, Leo’s hand resumed stroking his erection. Soon, I was completely inside, and it felt mind-numbingly pleasurable, but I couldn’t really enjoy it because I was too busy scanning Leo’s face.
“It’s…” he began. “…it’s not bad.”
That shocked me into laughter. “That’s reassuring,” I teased.
“‘Not bad’ is a compliment.” He closed his eyes as if to better focus on the sensation. “I feel really stretched out, really full, but also you’re pressing against my prostate, and that feels good.”
“Tell me when you want me to move,” I told him.
“You can move now.”
So I did. I got him to raise his hips and tried a bunch of different angles, listening to Leo’s feedback. “It’s a bit deeper than that,” he said. “Maybe that’s it? Can you try a bit harder?”
At one point, he started laughing, covering his face.
“What?” I asked, going still.
He peeked at me through his fingers. “It sounds like I’m giving you directions on how to park your car or something,” he said.
I chuckled. “It’s like that sometimes.”
“I always thought it’d be more…glamorous. In movies and TV shows, they just…do it.”
“That’s true. One character just sticks it in, and then they both start moaning in ecstasy,” I said.
“We do a lot more talking,” Leo said.
“Yeah,” I agreed, “but I like talking.”
Leo’s smile became shy. “Me too.”
I grinned at him, then rolled my hips, and his smile slipped. “Yeah,” he breathed. “Do that again.”
I did, again and again, until his hand was a tight fist around his leaking cock, until my skin was covered in sweat, until we were both shaking and kissing and gasping against each other’s lips. Leo’s eyes went from wide to hazy to slits under lowered lids to squeezed shut as his orgasm racked through him, and I didn’t look away once.
A phone alarm shocked me into awareness. I was in a cocoon of warmth, the blanket pulled up to my neck and smelling of familiar laundry detergent.
The alarm kept blaring.
“Jesus,” I said, rubbing my eyes. “What time is it?”
