Playing With The Devil

Chapter 3

I woke up a few hours later. A clock on Aidan's side of the bed read 3.44 am. A soft groan escaped my lips. I was still hard, or at least I'd become hard again from whatever dream I'd been having. I wasn't quite sure which it was, but regardless, I needed to do something about it this time. Aidan was facing the opposite way to me now, his back pressed into my chest. I shifted my hips upwards to get more comfortable, and maybe so I could move out to the bathroom to deal with it when I heard a moan beside me. Realisation set in as I felt my cock wet and enclosed around something tight.

I looked down at my crotch, the sweatpants down about my knees with my underwear. My length was up in between his thighs and halfway inside him. Countless thoughts ran through my mind as I tried to figure out the most logical explanation. I knew I had told him to look after it if it was still hard if he woke up, but I didn't expect anything like this. I was expecting a blowjob or maybe he'd wake me up and ask for something. I mostly hoped it would simply die on its own and we would wake up refreshed instead. But if he was okay with this, maybe I could go further. Wake him.

I gently shook his shoulder and whispered, "Aidan."

"Hmm?" he groaned.

"Do I have permission to move inside you?" I asked gently. Only halfway in and I was begging for more. I wanted to push myself further, hear him scream. Gabe, calm down. Gentle first.

"Mmm..." he said sleepily.

"I need words," I said. I lifted his leg slightly, slipping my length out of him. He let out a loose whimper, his fingers gripping the pillow under him.

"Ye-... Yes," he mumbled tiredly.

I gently laid him on his back, kicking off the pants and underwear. This was messy, but as long as I kept checking in, we could make it work. I moved on top of him and spread his legs to give me room. His briefs were on the floor next to us. I leaned down and started to leave kisses along his neck, nipping gently after each one. I kept it gentle, but still knew they would leave marks. He let out soft whimpers, his breath becoming shaky.

I breathed in to keep myself in control. I was going to be gentle. I constantly reminded myself. I wanted to make this comfortable and enjoyable for him. My hand went down his body. As I reached his clit, I rubbed my thumb over it. A louder moan left his lips and I groaned at the sound alone. That's what I was looking for. Gorgeous.

"If you get dysphoric, please God, let me know," I whispered. I slid a finger inside him, curling it. "I'm going to make this feel good, not bad."

"Okay... Okay," he whispered tiredly.

I leaned up, moving my finger inside him, slipping in a second soon after. I watched his eyelids flutter open, his lips parting further as his moans became more audible. He was more awake now, able to properly see and understand what we were doing. He looked so adorable in the hoodie; it was so big on him. I wonder how he'd look in one of mine. My fingers slid out of him, and I placed them in my mouth, licking up his juices. Even in the almost pitch-dark room, with just the moonlight filtering through the window, I could see how flustered he was becoming. His hands went up to his face, hiding behind his sleeves.

I lifted his hips, lining my cock with his entrance. I looked to him for one last confirmation and with his nod, I pushed in slowly. His back arched, and a loud whimper echoed through the room. His hands went up instantly to my waist as I slid further into him. His fingers gripped at me, his nails digging into my hips, whimpering louder still as I stretched him. His body tensed causing his walls to tighten around my cock. I was already going slow. The trauma he'd gone through was clearly not out of his system and he needed me to do better. I needed to keep him talking and go slower. I didn't care how slow, I only cared for his comfort.