Page 170 of Bad for Me

"Ian," Henry whines, face down on the pillow.

"Shhh, I've got you, I promise."

My hands move from his thigh, down his leg and foot. Then up the other leg until I'm massaging both thighs at once, kneading up to the bottom of his ass. Trying not to let my dick graze him, because I'm not trying to frighten him off, I climb up on the bed, massaging his ass cheeks and up to his lower back. I add more oil, pouring it directly on his skin, letting it trickle down his ass crack.

Gently running my fingers through the mess, I press against the outside of his hole with my lubed up fingers before moving back up to massage his back and shoulders. My dick lays against his back when I lean across him to gently suck on his earlobe.

"Trust me?" I whisper. He turns his head enough for me to see him nod.

I make my way back down his body, focusing on his delectable ass. I knead the flesh, spreading his cheeks apart and running my thumbs up and down his crack. After dripping a bit more oil on my fingers, I rub them all around his hole, pressing in the slightest bit, pushing the lubricant inside.

"Roll over now," I tell him, hovering over him and kissing him lightly once he does. Then I lay next to him on my side, slowly stroking his cock with my lubed-up hand. "The CBD will help your muscles relax so you can take my fingers," I tell him gently. He doesn’t look too surprised or apprehensive. With this much prep, it's probably pretty obvious what I'm about to attempt. "If it's too much, tell me to stop or slow down." He nods against my lips. I can tell he's nervous, just like the first time I rimmed him by the hot tub, but he doesn’t move away. Instead, he bends his knees so I can get access from the position we're in. "I'm going to make it so good for you, Daddy."

Directing him to keep stroking his cock, I trail my fingers down, circling his hole with slightly increasing pressure, until the tip of my pointer finger barely breaches. Slowly, I press in farther, to the first knuckle, massaging back and forth gently until he seems to relax into it.. When I remove my finger, he actually flexes his hips like he's chasing it.

"Why did you stop?" he asks breathlessly.

"Just getting more lube," I assure him, and I work more of the oil into his asshole little by little, until I'm a full finger deep inside him. I muffle a groan against his ribs. "Your virgin ass is so tight." The words slip out before I can think better of them, and Henry clenches. His ass tightens around my finger, which just makes me groan more, and my cock jerks, leaving sticky, wet pre-cum all over his hip. I roll my hips into him, rubbing my length against him. He seems to relax when he sees how affected I am by him and relaxes again. I resume massaging my finger in and out of his ass before teasing a second finger.

"Breathe," I say, soothingly, watching his face as I push the second finger inside. He breathes out and then groans as the second digit pushes past the tight ring of muscle. "Bear down for me," I tell him. "Like you're trying to push me out." He does, and the muscles relax further, the motion sucking my fingers further into his ass. "That's it. Just like that. That's how you get the muscles to relax. Your instinct is to clench up, but you have to bear down instead." I feel his ass ripple around me as he tries it again, and I push both fingers all the way in.

"So good," I praise him, and he leans down to kiss me while I fuck him gently with my fingers. "How does it feel?"

"Different," he says, his voice low and thready.

"You ready for the next part?"

His eyes widen a little, and I chuckle. "No, not that. You're not ready to take my cock yet." I pull myself up to my knees, situating myself so I can see all of him. "God, I love watching my fingers disappear inside your tight ass," I say huskily, looking away only to watch his face as I flex my fingers.

Henry hisses in a breath.

"Oh yeah, there it is."

The pads of my fingers brush over the soft, smooth mound of his prostate, and he bucks. I massage him from the inside, his moans driving me just as wild as he is. He's not even touching his dick, he's just gripping the towel beneath him, writhing against my hand. His moans are low and guttural, and I have the primal urge to rut into him like a fucking animal. His climax comes fast, and he shouts out as if surprised by it, but I also know how intense it can be. I reach for his cock, stroking his orgasm from him, still massaging his prostate. He keeps coming, his dick jerking and pulsing even after the fountain of cum has stopped aside from the milky white fluid that drips from the end.

"Ian," he cries. "Fuuuucckk!" He roars as a fresh wave of cum spurts from his cock in spectacular fashion.

"Holy fuck," I exclaim, reaching to jerk my cock because I'm about to come whether I touch it or not. I barely get two strokes in before I'm coming all over his cock, balls, and ass.

Once I catch my breath, I gently pull my fingers from him and wipe them on the towel beneath us before collapsing next to him. He turns to face me, pulling me against his body and kissing me fiercely. Our bodies come together, spreading our combined release between us. Eventually we manage to come down, laying face to face, staring at each other in awe in between light kisses and awkward chuckles.

"I hate to break it to you, Daddy. But you're a born bottom."

He looks a little unsure of himself, like he’s rethinking his entire identity and not just his sexual preferences. He almost looks embarrassed, and I’m quick to correct that nonsense. "That was?—"

"The fucking hottest thing I've ever seen in my life," I finish for him. "I didn't think that really happened. You're like a fucking unicorn sex god."

Henry barks out a laugh. "What?"

"Baby, you just came once from my fingers in your ass alone, and then fucking erupted a second time when I milked your prostate."

"And that's a good thing?"

"It was so hot,Ifucking came. Did it feel like a good thing?"

"Well, I mean, yeah, it was pretty… Okay, it was the most intense orgasm I've ever had."

I bite my lip and move my mouth to the shell of his ear. "Just wait until you're coming with my cock buried in your ass," I whisper.

---