Leo (Vigilance 3)

I tongued him until he was panting, whining, begging. Then I slid a finger in too. He gasped, but I kept going, working my way into him. He needed to be well stretched if he was going to take my cock, and he was, every fucking inch.

It had been years since I’d fucked a virgin, and even then, it had been a hardened operative who’d decided he wanted to experiment. Ezra said he wasn’t fragile, but I knew how easily I could break someone his size. I didn’t mind giving pain during sex, but this wasn’t the time for it. Ezra needed care. He needed to know just how much pleasure his body was capable of.

When I reached under him and touched his cock, he jumped.

“Oh God, I’m so hard it hurts.”

“I know, sweetheart. I’m going to give you some relief.”

“Again?”

“Yes, I want you to let go and come for me while I open up your gorgeous ass.”

“You’re… too much.”

“Nah. You can take me.”

“I don’t… I mean… Yeah, that too.”

I laughed. “You’re mine. You can do anything I want you to.”

“Oh fuck, I…”

“I’m going to fuck you until you can’t think, can’t do anything but feel. You’re never going to forget this.”

“I couldn’t. Not with you.”

His words sent warmth through me. I wasn’t going to let him down. “Don’t move.”

I leaned over and retrieved lube and a condom from my nightstand. I slicked my hand, then positioned myself behind him again. As I slid my lubed hand up and down his cock, jacking him with smooth, careful strokes, I lapped at his hole again before pushing two fingers into him. He groaned, but he didn’t fight me. “You can do it.”

“Your hands are so big.”

I smiled. “They are, but that’s good because—”

“Your cock is huge.”

“Oh, sweetheart, you’re going to do just fine.”

Somehow I was going to go slow enough for him. I was used to men who’d often prepped themselves so I could drag them out behind a bar and drive right into them. I thought that was all I needed, but I’d been wrong. Feeling Ezra tremble under me, knowing he was depending on me to teach him what he needed to know was pure bliss.

I worked my fingers deeper until his passage loosened and his tension melted away. When I pressed against that secret spot inside him, he cried out.

“Please.” I did it again, and he pushed back against me. “More.”

I knew it wasn’t what he meant, but I pulled almost all the way out of him, then added a third finger, watching as his ass stretched to accommodate me. His body’s grip on my fingers was almost painful.

“Oh my God. That’s too much. I don’t think… I don’t think I can…”

I took hold of his cock again, moving my hand up and down as I held him in a tight grip. “This will help.”

A few moments later, he relaxed again, and I was able to push farther into him. I twisted my wrist, and he gasped.

“That’s… Fuck… I don’t know if that hurts or feels good.”

“Do you like it?”

“Yes!”

“Then it doesn’t matter, does it?”

“No… I don’t…” I pulled out, twisting my hand as I did. “Oh God, Leo that’s… incredible.”

“It’s time to make you come again. Ride my fingers while I work your cock.”

“I don’t think—”

“Do it. I want to watch you fall apart.”

“Please.” I wasn’t sure if he was begging me to stop or to get on with it. I doubted he knew either.

I squeezed some lube on my hand and took hold of his dick again. This time I gave him faster strokes, and he thrust his hips, pushing himself into the circle of my hand. “That’s it, take what you need.”

I finger-fucked him, and he took it so well, driving himself back, impaling his ass on every stroke.

“Jesus, I love watching your hole stretch. Think about how it’s going to feel to have my cock in you.”

“So much. So full.”

“That’s right. I’ll fill you up and make you beg.”

“Yes. Leo, please.”

“Come for me, sweetheart. Show me how much you need this.”

He whimpered, and his movements got faster and faster until he cried out, and I felt the sticky wetness of his cum coat my hand.

He collapsed against the bed when he was done, and my fingers slipped from his ass. “That was so good, Ezra. I’m proud of you.”

“Mmm,” was all he said.

I rubbed his back. “I’ll give you a few minutes before you take all of me.”

“I really don’t know if…”

“You can come again. I’ll make you. Tell me your fantasies. Tell me what you want me to do to you.”

He shook his head.

“Ezra, turn over and look at me.”

He stayed still for several seconds before finally rolling to his side and looking at me with heavy eyes. His cheeks were pink from exertion or embarrassment, probably both.