Page 24 of Reckless

He was dead silent. Then he groaned softly. Encouragement? Protest?

I went on. “With your permission, I’d like to see whether that’s possible for you.”

He half-sighed, half-laughed into the pillow, and I hoped he didn’t find me completely ridiculous.

“Hm?” I asked.

“Yeah,” he whispered. “I…I guess.”

I stroked his arse. It was a thing of beauty, broad and curved, curls of light-brown hair dispersed evenly over it. The thought of parting his arsecheeks and slipping my fingers inside him had me harder than ever. But I made myself wait for it, taking a moment to feel between his legs to the dampness on the sheet below, nudging his softened cock with my fingers before returning my attention to his arse. Eventually I spread him, exposing his hole. I took a moment to enjoy the sight, then let go and squeezed some lube onto my middle finger. Robbie took a deep breath when he heard the cap click shut.

He was very tight. I added more lube, and tried again. “Good,” I praised quietly when the muscle slackened to admit my finger. After a moment’s probing, I attempted to add my forefinger as well. Robbie tensed immediately. “It’s alright,” I murmured, and went back to just one.

Robbie made a small, strained noise that didn’t sound like pleasure.

“No?” I asked quietly.

He didn’t answer.

“Is it uncomfortable?” I asked.

“I dunno.” He turned his face out of the pillow so his voice was less muffled. “I don’t usually…do this sober.”

Ah.

“Do you want to stop?”

A hesitant, “No.”

I wished he sounded more certain.

“Alright.” This was one of those situations where I’d probably benefit from being a warmer, more caring person. I considered what I knew of Robbie. Recalled his horse standing in my yard, his smile when the animal had blown snot into his hair. The memory made me smile too. “Robbie,” I said, and I hoped I sounded a little warmer and a little less Siri-Does-Your-Prostate-Exam. “Open for me. That’s the way.”

“Sorry,” he muttered.

“Nothing to be sorry about. Think about what I’ve asked you to do.”

I could see him trying, unsuccessfully, to relax. He took a deep breath and let it out. I adjusted my position so I could run my free hand lightly back and forth across his shoulders. Gradually, his body softened.

“Good,” I murmured. And he relaxed further.

On the next slide of my finger, I used a slight pressure on his prostate. His breath hitched, and he moaned into the pillow, the sound surprisingly loud. I did it again, and he pulled harder against the restraints, muscles going taut. When he had eased into the new sensation, I pushed my forefinger in. He froze for a second, then his whole body seemed to shudder out the worst of the tension.

“Very good,” I praised, genuinely proud of him. He really was doing well.

I pushed inward and left my fingers buried in him as deep as they’d go. Closed my eyes and savoured the sensation of him clenching around me. I made a gentle crooking motion. The reaction I got was different this time, a soft whimper.

I worked like that for several minutes, testing out what pace, what pressure, what patterns drew the best responses. Soon he was moaning steadily, and the sound had just as much of an effect on my cock as before. I focused all my efforts on his prostate, manipulating it with more confidence now.

“Go ahead and come,” I urged. He stiffened, and I thought he was going to do it. But he just stayed like that, thighs quivering, before a breath of frustration burst from him.

He panted into the pillow for several seconds as I tried once more to get him to the edge. “Uh. Stop. I think.”

I stopped at once and withdrew my fingers.

“Sorry,” he said between breaths. “I don’t think I can. It kind of hurts.”

“That’s alright.” I wiped my hand with one of the disinfecting wipes. “Would you like me to untie you?”