Jack wants to sleep in but his puppy is wide awake (NSFW)
Jack Abbot / Dennis Whittaker (hucklerabbot mentioned)
CW: explicit nsfw, old man things, casual sex, puppy space, cockwarming
It’s 7 in the morning and Dennis hasn’t been able to fall back asleep since Robby left for his shift. His body is far too used to their schedule, despite staying up late. Poor Robby is the only one who has to get up, sleep deprived after their…eventful night.
His body isn’t only affected by his sleep schedule, though. After starting HRT around six months ago, Dennis has been needy. Needing extra cuddles and affirmations due to his mood swings. Needing to fill the never ending void that is his stomach. Needing the AC on full blast or he’d sweat buckets.
But most of all, what really made Dennis feel like a man, is his most unsatiable need; the need to be fucked.
Every morning, like clockwork, he wakes up extra sensitive. Now, this isn’t usually an issue—really quite the opposite, Robby tends to wake up just as eager. Jack, unfortunately, not as much due to his age. Of course Jack loves to please Dennis, as well as himself, he simply can’t get it up as much anymore. He tends to use his hands or preferably his mouth, tasting and lapping up Dennis inside and out. Inspecting every inch of his changing body, telling him how beautiful he is. Adoring the effects of testosterone, and how they make Dennis so happy.
But right now, Jack wants to do nothing but sleep. His jaw is sore from last night, eating Dennis out and gulping down Robby’s cock. Sleep deprived— and traumatized— from his shift the night before. Exausted physically and mentally.
When soft wet licks pull up Jack’s cheek, his arm lazily waves, shooing Dennis away. A low, sleepy grumble of disapproval comes from Jack, who’s face is buried in a pillow.
“Jack,” Dennis whispers, “Jack….” He knows he’s awake. No answer.
So he resorts to what always works, “Daddy.”
Jack’s eyes remain closed, but Dennis finally gets an answer from him, “what, puppy?” His voice his sleepy, deep and gravely from exhaustion. Dennis cuddles closer, wriggling a leg between Jack’s thighs.
“Need you.” Dennis whines, slotting himself between Jack’s leg, mounting it and rocking their bare bodies together.
“Good, good…like that.” The praise mindlessly comes from Jack, barely even conscious.
“No…” Dennis whines, “I need you inside.”
Jack’s face stays turned into the pillow, avoiding those begging eyes he knows are pointed at him. “Dennis,” he’s never in the mood when he calls him that, “I’m fucking exausted. Just use my leg.”
Dennis starts to hump his leg again, slowly grinding his slick folds along Jack’s leg. “Feel how wet I already am for you.” He mutters, “how much I need you.”
Jack is fighting a loosing battle. “So whiny,” he teases. “You’re a big boy, you can do it puppy.”
“Please, Daddy? Please—I’ll be fast.” Dennis stops the rocking motion an lays flat on top of Jack.
“But I won’t, you know I won’t. I’m not even hard, Den.” Jack admits, not awake enough to care for his ego. His face is pried out from the pillow by hands on either side of his face, eyes begrudgingly open.
“I can fix that.” Dennis hums, ghosting their lips together, feeling his hot breath but not meeting for a kiss. Leaving Jack unsatisfied, “if you let me.” A finger reaches out to twirl one of those silver curls.
Jack sighs, knowing he won’t have much of a choice, “show me what you’ve got, then we’ll talk.” Dennis smirks at his reply, attempting to slip under the covers. But his face is caught by a large hand, Jack pulling him into that kiss he never got. “And quit teasing.” He huffs.
“Yes, sir.” Dennis breathes, kissing his face and then jaw. Then lower and lower, down his neck and to his chest. Teething carefully on his pink nipple. Suckling and kissing at each one before traveling down further, giving attention to every part of his body. His hands trail behind, ghosting over where he’d previously been pressing his weight onto Jack— who is loving the attention. Dennis lets the blanket slide off of them as he works his way down, making sure Jack can watch him.
However, Jack is still half asleep, the soft touches and tender care only making sleep find him easier. Though that changes when he feels the flat of Dennis’s tongue runs up his soft dick, hilt to tip, earring a pleased hum from Jack. “I love the way you taste.” Dennis starts, gripping him with both hands and lapping gently at the head, small puppy licks. Tongue turns to lips, kissing right over the top before taking it into his mouth. All his attention focused on the sensitive tip, suckling, running his tongue back and forth. He pulls away, “mmmh, the top still so sensitive, isn’t it?” Dennis asks, putting it back in his mouth.
Jack chuckles, loving when his puppy talks dirty to him, “yeah, a little. Feels good like that.” His eyes fall closed again, petting Dennis’s hair, enjoying the soft stimulation.
Going a little further, Dennis strokes up and down his soft shaft with both hands. His mouth works harder too— fitting the entire head inside. Popping it in and out, swirling circles over it with his tongue. He’s giving Jack all he’s got. Knowing if he works hard enough he’ll get a reward.
“Jesus— when did you get so good at that?” Jack groans, satisfied.
Pulling his mouth away to reply, those hands keep themselves busy, “had a lot of practice with Robby.” He tries to say nonchalantly but a big smile is plastered on his face. “Been wanting to show you— and to taste you.” He laps at the tip more, “you always do such a good job helping me, Daddy.” Dennis hums, “I want to make you feel good too.” One hand shifts to massage his balls, the other still stoking. He feels a small twitch come from Jack’s shaft, earring a pleased hum from Dennis.
“You’re so fucking adorable.” Jack hums, peeking down at him, unable to help himself from the beautiful sight. Dennis beams at his praise, wiggling his hips against Jack’s knee.
As those hands carefully work Jack, Dennis looks to him, “you know…you could still put it in soft.” He suggests shyly.
“And do what? Wait for me to get hard?” Jack jokingly suggests, but the shade of red Dennis goes tells him that’s exactly what he had in mind. “Really?” Jack asks, intrigued. Dennis smiles when he feel the shaft in his hands pull a little, twitchy and starting to harden.
“Please?” Dennis begs, still stroking him up and down, slowly but passionately.
Jack smirks and pats his thigh, signaling for Dennis to get on top. And that he does—eagerly but still carful as to not hurt his oh so generous lover. Lining himself up, Dennis carefully slips Jack’s slightly hardened cock in. His pussy is incredibly wet, allowing Jack to slide in with ease. The warm sensation of pushing in makes the older groan in pleasure, his cock happily responding too.
“See, told you I’d be fast.” Dennis teases, pleased that he can feel his hard work staring to take effect.
“Easy there, cowboy. You’ve got a long way to go.” Jack coos. Dennis nods, leaning down so that their chests lay flat against each other. He’s carful to only rock his hips slightly, not letting the soft appendage fall out.
Dennis continues like this, not getting any help from his sleepy partner, only the occasional mumbles of affirmations or gentle head scratches. But he doesn’t mind, adoring how Jack feels inside of him even like this— especially like this. It’s somehow more raw and intimate. And he’s so sensitive between his legs, clit perking out about an inch and half at this point, that any stimulation feels good. It feels amazing actually, slicked up and stuffed full, despite Jack not being at his full length— yet. As this motion continues, Jack gets closer and closer to standing at full attention.
“Thank you. You feel so good inside me.” Dennis leans even closer to finish the sentance with a kiss, rocking his hips so carefully.
“Anything for my sweet boy.” Jack hums, lazily meeting the movements once or twice, allowing himself to get worked up. “Now keep riding, juuuust like that if you want a treat.” Jack whispers, low groans of approval following.
“A treat?” Dennis repeats, more excited than before.
“Yes, a treat. Work hard and daddy will stuff you nice and full, sound good?”
Dennis nods, rolling his hips in slow practiced movements, “mmhm, yes— yes please.” With each stroke he can feel Jack getting harder, Dennis’s moans get more difficult to stifle as the cock inside of him grows in length. Sitting up, those hip movements get more confident, the strokes getting longer and faster.
“Fuck, that feels good.” Jack moans, slinging an arm over his face.
“Doing good?” Dennis asks, a little out of breath and falling further into that fuzzy space. He places his hands on Jack’s stomach to balance himself, gently pawing and kneading.
“Yes puppy, you’re doing amazing. That’s a good boy.” Jack assures him, reaching his free arm out to hold his thigh and gently thumbing the side.
Falling into soft moans, Dennis doubles he effort eager to please, to get his reward. Jack is fully erect inside of him now, reaching the deepest parts of his insides. Feeling every curve and vein slide in and out of him. He gets lost— gets sloppy.
Jack squeezes his thigh to get his attention, “hey—fuck— hey, slow puppy, slowly.”
“Yes, sir.” The pup complies immediately, “sorry daddy,” he whispers.
“It’s okay, you just got excited, didn’t you?” Jack comforts him, soft moans returning from both of them. Dennis nods, making sure his strokes are slow but passionate.
Dennis is expecting a punishment, something Robby loves. However, Jack tends to take a much more gentle approach when Robby is gone. Not to mention how he’s far too tired to do anything but let the pup get himself off. If Jack finishes too, that’s just a bonus.
But he knows Dennis wants it. His boy loves nothing more than being stuffed full of his warm cum. So he guides Dennis’s hips to where they are perfectly aligned, where he feels best. “Just like that, follow my hands, okay?”
“Mmhm..” dennis replies, barely audible. He feels mushy inside, loving every moment.
He mindlessly bucks into Jack, following his movements until both of them are panting and close to the edge.
“M’ close..” Dennis huffs.
“Me too—fuck, just a little more puppy, can you go a little longer?”
“Yes, daddy,” he nods eagerly, slowly laying himself down so her can hug Jack tight. “Can try.”
Large hands wrap around Dennis’s back, “Such a sweet puppy, aren’t you?” Jack hums, one hand moving into his hair.
“Mmhm…” Dennis barely registers what Jack’s saying, knowing his sweet tone means praise. His goal is in sight, and that’s all he’s focused on. Rolling his hips so that he can feel every inch inside of him, “Can’t…can’t wait.”
“Aww, you gonna cum puppy?” Jack asks, rubbing his back. All Dennis can do is nod. “That’s okay, I’m close enough, you can cum for me baby.”
With permission, Dennis rocks just a little harder into him, clasping his legs tightly around Jack’s waist. Chasing his orgasm, feeling his cock spread him wide and continously rub against his clit. “Sososo good…” Dennis whines, closing his eyes and humping helplessly until he finds that sweet spot— seeing white. His walls clench around Jack, making them both moan. Pleasure washes over him, twitching and shaking as he peaks.
The sight is adorable, Jack feels himself getting closer to the edge too, enjoying every moment of Dennis cumming all over his cock. The slick pooling out of his already leaking cunt. “Keep going puppy, I’m almost there.”
Dennis doesn’t really need to be told, still keeping a steady pace, though he nods eagerly at the command. His brain may be foggy, but he still wants his treat.
And a treat he gets. Jack groans pulling Dennis deeper onto his cock, one, two final strokes before he bottoms out. Hot ropes of cum shoot into those velvet insides, the two of them moaning together at the sensation. Dennis carefully grinds against him a few more times, making sure to milk him of every last drop. “‘Mmmh…so full, daddy.”
“That’s right. Full of daddy’s cum, aren’t you?” Dennis nods, burying his face into Jack’s neck. Teething at the skin, suckling and kissing upwards. Over his jawline and to his lips. Sloppily making out with his lover. Devouring each other.
When Jack tries to push Dennis off, he won’t budge, gripping tighter. “Den, puppy, you gotta let go.”
Shanking his head, Dennis finds shelter in his neck once more. “Stay. Like this.”
“I’m really, really not up for another round Dennis.”
“I know. Just…wanna feel you. Sleepy.”
Running his fingernails along Dennis’s back, he hums, thinking, “you want to sleep…like this?”
“Yes please.” Dennis wiggles his hips, adjusting so that he’s comfier.
Sighing, unable to deny his sweet puppy such a request, Jack agrees. “Okay. But I’m gonna get you cleaned up as soon as we’re awake, alright?”
Dennis nods, giving a chaste lick to his cheek as a sign of aprooval. Jack hums, pleased that his pup had been lulled back to sleep. The two rest easy like this.