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I couldn’t believe that he was more than likely gay, maybe bi, but had never played with his ass. How did you figure out if you were a top, a bottom, or vers if you didn't at least explore a little? Then again, some guys never wanted their ass penetrated at all. I just sure as fuck hoped Adrian wasn’t one of them.
Finally returning his gaze to me, Adrian leaned in and gave my lips a little lick. It wasn’t quite a kiss, but it was still tender and intimate somehow.
Laughing a little, I reached out and ran a hand through his hair and down his back. I shifted into a more comfortable position then patted my leg. “Over my lap, Pup. We’re going to show you how good your tail’s going to feel.”
When he obeyed, I could feel his cock against me, and I fought not to squirm. I ran my hand slowly along his ass cheek, murmuring, “Relax. We’ll take it slow. Okay?”
Adrian gave a little whimper, but he let his head rest against the floor and closed his eyes. His muscles were still tense, but I could tell he wanted it, even if it worried him.
“Shh.” I stroked his back, down his spine. I kept my voice low and even, every bit the master he wanted me to be, as I began to murmur to him. Not everything I said made sense, but he was my pup. It wasn’t about the words themselves. It was about soothing him with the sound of my voice, with my touch. I had to earn his trust and keep it when he was faced with something scary.
I had to deserve it, too.
A sigh escaped Adrian as my hand skimmed over his ass and down his thigh. Running my hand back up, I let my fingers trail just over his hole, barely touching. He tensed for a moment, then relaxed back as my fingers kept going.
Every time I brought my hand up and down his cheeks, I tried to get him more used to my touch — a feathery caress over his clenched opening, a firm touch from my fingers as I kneaded one cheek, a gentle tease as I circled his hole but never quite touched him.
Needy little sounds eventually started tumbling out of him, and I knew he was ready for more when he started grinding his cock against my thigh.
I opened the lube as quietly as I could, and while he briefly tensed, it wasn’t long before he relaxed again. I poured some into my palm, setting aside the bottle and warming it up with my hands before I slid a finger over his ass. Just one, barely touching, at first, then carefully sliding in.
I remembered what it had been like the first time I’d explored there. It had been a stretch, a weird feeling, but it had gone from discomfort — and a little bit of pain, admittedly — to something euphoric. I didn’t want him to feel that pain, and I was going to make sure he was damn good and ready before I slid the tail in.
I glanced at the plug, trying to judge how much to loosen him before sliding it in, but kept going as I murmured, “Good boy.”
I kept my finger still, just letting him get used to the feeling while I used my other hand to caress his back. I could still feel his dick pressing against me. It felt a little softer, but it was easy to tell he was still turned on.
“That’s my good pup.”
When he finally gave a low huff and rocked his hips a little, carefully fucking himself on my finger, I knew it was time to move.
Slowly easing my finger almost all the way out, I let it gently sink back in as Adrian gave a low moan. “That’s right. I think you like having Master touch you. I can’t wait to see how you look with your pretty tail.”
Adrian gasped as I pushed in deeper, then clenched hard around my finger. Bingo. Prostate. Making small circles over the sensitive gland, I felt a rush of something as he pushed back again and whined for more.
I wanted to keep touching him, to taste him, but I wanted to see the tail in him even more. A second finger, slow and careful, joined the first. I found his prostate again and stroked. Over and over, I whispered what a good boy he was, thrusting my hips up against him.
When I thought he was finally stretched enough and turned on enough for the tail, I eased my fingers out. Adrian let out a needy whimper, but arched his ass up, instinctively begging for more. “That’s right. Master’s going to give you everything you need, Pup.”
Picking up the plug, I spread a little more lube over the base and brought it up to the stretched ring of muscles that were desperate to be filled again.
“It’s going to feel so good. You’re going to love how it feels when you wag your tail for Master.” My free hand was rubbing up and down his back, over his ass and then back up, making long, soothing strokes. “You’re going to be such a pretty pup. You want to be a pretty pup for your master, don’t you?”
Adrian gave a low bark and arched his ass up again. Letting the plug rest just against his hole, I let him get used to the feeling as I kept up the gentle touches and tender words.
When I could feel his body start to relax again, I pushed the toy gently against his body and watched it stretch him as it sank in. He gave a low whimper but didn’t use his safe word. Little shivers ran through his body as I slowly eased the plug into him.
“It’s going to feel so good. It’s going to look so incredible, Pup. My pretty pup is going to love his tail.” I leaned into him, wanting him to feel like we were doing it together. He wasn’t alone in this. Master was right there with him.
When it was about halfway seated, I started kneading one cheek. Pressing my thigh up harder against his cock, I started urging him to move. “Show Master how good it feels. That’s right, my sexy pup. Show me how you like it.”
Adrian made desperate little sounds, and his head finally came up off the floor. Bracing his elbows against the carpet, he rocked his hips. It was almost too small a movement to even notice, but it brushed the toy up against his prostate. He made the sexiest little sound and started thrusting back and forth on the plug, desperate for more. He was going to be a needy little bottom, and I loved it.
He made it easy to focus on him, to let the world fade away. It was so fucking difficult sometimes, but not in that moment. It felt so natural to slowly push that plug inside of him until it was fully seated.
I groaned, the sight of it even hotter than I’d expected — which was saying something. “Fuck,” I whispered, “you look so good for your master. So good. Do you like your tail?”
I put my hand in front of him, close enough for him to nuzzle, or lick, or do anything to — and I wanted him to, wanted to sink even further into this place and state of mind. He buried his face against my hand, and I felt the lightest little caress of his tongue.
