Chapter Thirteen: Anson

D addy spends what feels like forever working me open. I writhe on his bed, losing track of time and place. He uses a lot of lube, and his mouth, and he distracts me from the stretch by sucking my cock like he’s got an instruction manual on everything that makes me tick.

But, unlike when I was in college, I relax into the intrusion of his fingers. Yeah, it still feels a bit weird being filled up, but it doesn’t have the same sense of wrongness that I felt all those years ago. I can’t even say that I’ve used toys over the years, either, because that never appealed to me.

That’s probably why Daddy spends so long stretching me out. Aside from the times in college, I’ve never had anything inside me. My body hasn’t gotten used to being opened up or filled up. He’s basically working with a virgin hole.

Not that he seems to mind. He’s been moaning and groaning around my cock, whispering filthy praises about how good I taste and how tight and perfect I feel around his fingers. That has helped relax me, too.

As much as I’d like to test out being bratty sometimes, deep down, I really want to be his good boy. Especially tonight. It’s our first night together, for one. And it’s the start of our Christmas holiday. I know the original intention was to avoid getting sappy about the festive season, but now it feels like this whole experience is a Christmas present from the universe. Like, I was driving here and second-guessing all my life choices and now…now I’ve gotten exactly what I wanted when I first started exploring kink.

I’ve found myself, and I want to reward my Little side. Merry Christmas, Anson, you’ve got yourself a Daddy!

And, yeah, I want to reward my Daddy, too. He deserves a good boy for Christmas.

“I think you’re about as ready as you’re going to be, sunshine,” Daddy says, cutting into my thoughts. He pulls his fingers —all three of them!— out of me, and I feel empty in a way that surprises me. “What do you think?”

I suppose I was getting used to my ass feeling full and stretched because I whine and lift my hips. “I’m ready, Daddy.”

“Can you roll over onto your front for me? Good boy,” he adds when I do as he asks. “And on your hands and knees?”

As much as I’d like to be facing him when we do this for the first time, I know that this position will be easier for me to handle right now, so I comply again, preening when he repeats his praise.

I listen to the click of the cap from the bottle of lube, and I gasp as his fingers breech me again. It feels different from this angle. Not bad, but in the few seconds of reprieve from having them inside me, it’s almost like he’s got to work me open all over again.

“You okay? Need me to stop?”

I’m surprised to realize that that’s the last thing I want right now. I shake my head and rock back tentatively, gasping some more as the stretch becomes more intense. “D-don’t stop. Just… oh! ” I jolt as a burst of intense pleasure hits me out of nowhere. In my grownup brain, I know that Daddy’s just crooked his fingers over my prostate, but feeling very Little and vulnerable, all I can say is, “More of that , Daddy!”

He does.

It feels so good that it makes me forget the burning of the stretch. It makes me rock back and forth, picking up speed as I get him to nudge that magic spot again and again and again.

This time when he removes his fingers, I complain, “ Nooo …”

Daddy’s laugh sounds a little strained. “Sorry, honey, but Daddy was about to come without ever making it inside you. It was very hot watching you fuck my fingers.” Something much thicker than a finger nudges its way inside my rim and my breathing hitches. “Remember, baby, you’re calling the shots here. Red light and I’ll stop.”

Exhaling, I nod. With my eyes squeezed shut, I try to relax, remembering just how much I enjoyed his fingers inside me. If I liked that, surely I’ll like his dick.

He takes his time sliding into me in short, slow increments, backing out and rocking back in at what has to be a fraction of an inch each time. But the more he does, the more I push back onto him, and it’s not until I feel his balls pressed up against my bare skin that I realize he’s all the way inside me and the pain is…nowhere near as bad as I remember this feeling.

Yeah, there’s an ache and a burn, but none of the stabbing sensation I felt when my college hookups tried to fuck me.

“Is this okay?” Daddy asks lowly, smoothing his big hands down my sides. He squeezes my hips and then starts the motion all over again.

“Uh-huh,” I nod, experimentally rocking forward on my knees a fraction, then rolling back again. Daddy makes a strangled sort of sound, and then I realize I’m making one, too. “It’s…it’s good…” I sound surprised even to my own ears.

“It feels better than good for me,” he admits through heavy breaths. “Tell me when you’re ready for me to move.”

I have to marvel at his self-control. Knowing how long it’s been for him, and how tight I must feel, especially when we’re doing this without barriers…he really is a patient, caring man. “M-move, Daddy,” I tell him and he starts gently thrusting. “S-slo- oh !”

My front half collapses onto the pillow, and I cry out as he already manages to nudge my magic spot with his movements. Maybe it was all that time spent stroking the spot with his fingers, so he knew exactly how to angle himself. Plus, it doesn’t hurt that his cock is thick, filling me up completely.

“You okay, baby?” he asks, but he sounds smug, like he knows exactly what he’s doing.

He proves that he does when he repeats the exact same movement again and again, drawing out more “oh, oh, oh”s from me. Every time he hits that magic spot, shockwaves of intense pleasure skitter through my whole body. My cock is hard and leaking so much I almost suggest that he diapers me again, and he hasn’t even touched it.

“D-daddy,” I gasp as he propels forward again, my voice muffled by the pillow. I turn my face to breathe and repeat, “D-daddy, I…I…”

Words are evading me. Now that I’m not braced on my arms, but more like a combination of my shoulders and face, I reach underneath myself and grab my dick. I don’t even have to move my own hand much, because Daddy’s thrusts are moving my precum-slicked cock inside my fist. My balls are drawing up tight and I squeeze my dick to try and prevent the inevitable.

“You’ve been such a good boy,” Daddy pants, his movements growing steadily faster and harder, “you’re taking my cock so beautifully, sunshine.”

“I’m…I…I’m…Oh! Oh! Oh! ” I want to warn him of how close I am, but I can’t get the words out for every direct nudge against my special spot.

He breathes heavily, shakily, and I’m pretty sure I can feel drops of his sweat landing on my back. Then he asks in a low, gravelly, sexy voice, “Are you going to come on Daddy’s cock, baby? Are you gonna make a mess in Daddy’s bed with your cum?”

I nod, almost sobbing with how hard I’m trying not to do just that.

“Be Daddy’s good boy, Anson. Let go. Come for Daddy.”

“Oh,” I let out the involuntary sound with every thrust, “ Oh …oh! ” I’m too far gone and the pleasure is too intense now. I see stars as my orgasm barrels through me. “Oh , fuck , Daddy! ”

I erupt over my hand, my tummy and the sheets underneath me. It feels like I cum for hours, and I chase every last bit of the high that I can. I’m dimly aware of Daddy grunting and swearing through his release, too, but it’s not until I’m lying on my back and catching my breath that I register the stickiness dribbling out of my ass.

I scrunch up my nose and whine at the sensation, shifting my hips to try to minimize how icky it feels.

“What’s wrong, sunshine?” Daddy asks. He’s collapsed on the other side of the wet spot I made and is squinting over at me with mild concern.

“I need wipes, Daddy.” My answer is plaintive and pouty. “Feels… blech .”

“Oh, baby, I’m sorry. I didn’t think. Hang on.” He climbs out of bed and disappears out the bedroom door, but returns soon after with a wet washcloth. When he brings it gently to my ass, I’m relieved to find that it’s warm. “I guess this is part of your sensory thing, huh?” he asks me as he wipes me clean. “Not that it’s my favorite feeling in the world, either.”

I shrug, already feeling a lot better for the quick wipe down. “I’ve never felt this before, but it’s icky.”

Tossing the used cloth aside, he crawls up the bed beside me, on the side without the wet spot, and cuddles up at my side. “Well, maybe next time, if you still want me to top, we can use condoms to prevent the icky feeling?”

I find the offer really sweet. How many other guys do I know who would offer to wear a condom if they don’t have to?

Shaking my head, I answer, “Nope. I like everything else. Just gotta have wipes for after.”

“So…you enjoyed that? It wasn’t too painful?” I turn my head to find him studying me seriously.

“Daddy,” I say with exaggerated exasperation, but a huge smile gives away my real feelings, “didn’t you see how much I liked it? I made a huge mess and everything.”

He snickers and rubs his cheek against mine. I love the feeling of his beard on my skin. “I’m just checking, honey. But you’re right: you are all messy now.” He places his hand over my tummy, seemingly not at all worried that I still have a puddle of drying cum there. “I think maybe I need to give my baby a bath.”