“Pick a hole. You know what happens next.”

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Content warning: This story contains Daddy/boy play, lots of ownership/possession, force, and some humiliation. Everything depicted is between consenting adults, intentional, and previously negotiated to be well known that this is what we want to play with. The whole thing is based on an actual morning text message exchange with rife, and edited to make it more of a story.

I wake him slow in the morning. Light comes in easy through the blinds, gold on his skin and the bed. Our limbs are tangled as they often are while we sleep together. He is in small little boy briefs and nothing else, which is what I prefer he wears while he sleeps, and one of our rules is to respect my preferences and execute them to the best of his ability. (The flip side of that is that it is my responsibility to suss out my preferences, and to make them clear and known. It’s quite vulnerable, and transparent, more than I am used to being. And good practice.)

He shifts as I wake, getting out of bed to pee, drink water, and put my dick on. When I come back, he curls into my armpit and shoulder, snuggles his cute little boy butt up against me, pulls my arms around him tighter and sighs. Still drowsy and not really waking yet. He could cuddle for hours.

I let my mind wander to what I’ll do to him, getting hard. He is soft and warm against me. I slip the tip of my finger into his mouth and he suckles in his sleep. Sucking and then drifting into sleep slowly, pausing, then sucking again.

“Good morning, little boy. it’s not time to get up for school yet, but Daddy wants that ass of yours just for a little while. You’ve been wriggling against me all night.”

“Ohhh. Daddy …”

“I like the way all my soft warm skin feels. When I wrap around you all night and you writhe and press, you get me so hard. Feel that, little faggot? You get Daddy hard. Pick a hole, little one. You know what happens next.”

“Uhh yes Sir. I like when it pokes me all hard and hot. I like when you push the tip against my tight tight hole and pull me onto you with your big strong hands on my hips. I like thinking of you popping out and in just to feel that threshold give and grab your head tight and make me squirm.”

“You just stay still, baby, and let me use you. Rub it up and down against your little pink hole. Slide it between your cheeks. Daddy gets so hard for you, baby boy.” I pull his briefs down and tease his asshole with the dripping swollen tip until I can’t take it anymore. Until I have to have it. I plunge inside, burying it deep down to my balls, too fast, too hard, but I need it. To be inside. All the way.

“I don’t like to hurt you. But I need it, you know I need it.” My balls slap against you while I shove in hard.

He gasps and takes it, swallowing you up so deep. “Oh Daddy…” Whimpering a little with each thrust just makes me want to hurt him more.

I push his face down into the pillow. “Shut it, boy. Take it. Cry all you want.”

“Uhh no please Daddy.” My dick completely fills him. I feel him dripping already. The resistance is palpable as I push deeper, filling him up. His tight little young body tries to push me out, but it just gives you more to push against. I’ll force it in all morning if I have to. He’ll get used to it.

I fist his hair and hold his hole open. “You know I like it when you struggle. I can shove harder that way.” He’ll learn to open up for me, to give that hole, to open up and take it, in time. Right now I don’t mind shoving it in. I work it in and out. So tight.

“That’s my boy. Just for me, just for Daddy’s cock.” I like forcing it. Winning every inch with my size and strength. Filling him up so deep. I like knowing that I owns this ass. Only Daddy’s cock has ever ploughed it like this. I like how he squeezes me so tight when he wriggles and struggles. I like watching his body move under me.

“Mmm so pretty, my good boy.”

I like watching the tears darken the sheets and his tight little fists catching the pillows.

Into his ear: “I’ll just hold you down and let you writhe. Feels good as you resist, you squeeze so hard. Harder than when you come even.” The pressure is almost too much all around my cock. I feel like it could all come rushing out of you. Pour into this boy’s tight little ass. Why not? That’s what he’s for. My little fuck-slut. My holes to fill. Who’s going to know? Look at him. He’s a sobbing mess. Pathetic little fag. Daddy will set him straight. Daddy will make him a man.

“You just need some guidance, my boy. You’ll be just fine. Just do what Daddy says. Just take it for your Daddy. Take it all from Daddy’s cock.”

“Yes, Sir. I’m trying. I’m your prize, your toy, your slave. Yours.”

“All mine baby. That’s right.” He moans one more time and quiets under my words.

“This is what I need. My good boy. Daddy needs to bury deep in you. Empty out all that seed. Bury deep in those little holes, just for me.” He arches his back and does as he’s told. I feel it all open up. All mine.

“Mmmm. Yes Sir.”

“Unh fuck. Yes like that. Just like that. Open up deep for me.”

My dick starts pulsing harder, that shudder of getting close. He can feel it, starts begging. “Give it to me Daddy, please. I want your come. Please. I need it. Please.”

I’m panting in your ear. Coming hard inside. Thrusting until every drop is squeezed out. He pushes back onto me, panting and heaving to my rhythm. “Fuck. That’s what I needed, my sweet boy’s tight little ass. Good boy. Take it all. Fuck yes.”

“Ohhhh god,” he moans low and slow, releasing and letting himself come harder. “Thank you Daddy. I’m yours. All yours.”

I slowly ease my dick out and we collapse, breathe, soothe each other, until we get up and take on the day.

Featured image courtesy of Indie Porn Revolution

Published by Sinclair Sexsmith

Sinclair Sexsmith is a genderqueer kinky butch writer who teaches and performs, specializing in sexualities, genders, and relationships. They've written at sugarbutch.net since 2006, recognized numerous places as one of the Top Sex Blogs. Sinclair's gender theory and queer erotica is widely published in anthologies like Take Me There: Trans and Genderqueer Erotica, and online at Feministing, Autostraddle, AfterEllen, and more; they are the editor of Best Lesbian Erotica 2012 and Say Please: Lesbian BDSM Erotica, both published by Cleis Press. Sweet & Rough: Sixteen Stories of Queer Smut, Sinclair's first book of short erotic stories, was published in 2014. They use the pronouns they, them, theirs, themself, and live in Oakland, CA with their boy.

36 thoughts on ““Pick a hole. You know what happens next.””

  1. Ren says:

    Ooof. Cold shower time.

  2. DiAnna says:

    …and now *I’m* panting!

  3. Kyle says:

    heh heh heh… oh yeah, Daddy needs this, do it for Daddy.. mmmgod, love it so much, Sin… nicely done. Good thing I finished mine before reading this, or I’d be all distracted.. looking forward to Day 2, my friend.

  4. Trish says:

    “While he sleep”.

    Got me right there. Delicate use of English = totally sold.

    1. Sinclair says:

      Trish … I think maybe you’re being facetious? Because I think that “while he sleep” was a typo. But maybe it made sense in some way I wasn’t aware of? Anyway I’m confused.

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