Chapter 4
I watch him debate, seeing all his emotions flicker across his face while he decides to kiss or fuck.
During his conversation with himself, I tug his legs straight and massage his thighs.
His cock remains hard and occasionally drips precum when I push deeper into his muscles.
As much as I want to taste him, I refrain, giving him space to think while providing reassurance with touch.
“Will we not kiss while we have sex?” He asks, flicking his eyes to my lips.
“Most likely not, since on your hands and knees will be better if this is your first time,” I explain.
He frowns, shaking his head, “but I won’t be able to see you.”
“You’re just trying to get both,” I tease.
He immediately rejects that idea with a sharp shake of his head. “No, I want to watch you, see your face, see you cum. I want to feel connected to-you haven’t had sex with anyone at the office, right?”
“No, unlike some people in this room, I’m professional,” I answer.
“I haven’t either, so I’m just as professional as you,” he counters, and I feel more than see his foot stomping on the bed.
“For a boy that says he’s studied how to be good for his daddy, you sure like to behave with a lot of attitude,” I comment. Then climb off the bed, which causes him to panic and sit up. I stop him from getting off the bed by putting my hand on his chest, “I’m just getting ready.”
He settles, sitting back on his heels, and watches me closely, like he’s worried I’ll leave.
I step into my harness, positioning it correctly, then securing it before stroking my hand down the shaft.
The preattached dildo is black, smooth, and about 7 inches with a bulbous head and not too thick.
I’m glad I chose this one, especially now knowing this is Chase’s first time.
I look up to find him staring at me, full of lust. It gives me pause.
Sometimes, the act of having to choose, then put on the harness, and get everything positioned correctly can cause a hiccup in the flow.
But here with Chase, he’s looking at me like the act itself was sexy, even though I often try to rush through the process while pushing down the slight unease of needing something else besides my own body.
“Daddy,” he nods, “I want to have sex instead of just kissing,” he says confidently.
I hum, climbing back onto the bed while he lies back, then brings his legs to his chest. “Such an eager boy, how have I missed it?”
“I was playing it cool,” he answers. Snorting, I kneel at his ass before spreading a healthy amount of lube on my fingers. “I was,” he repeats, “playing it cool.”
“Of course,” I reply as I circle his rim.
He immediately clenches, trying to suck my finger inside him.
Flicking my eyes to his cock, I remember his earlier statement, so I bring my hand down, giving his shaft a hard slap.
He yelps, half sitting up before lying back down and fisting the blankets.
“You’re not in control,” I reprimand, “you don’t set the pace.
You will take what I give you without pushing for more. ”
“You’re being too slow,” he complains, so I land another slap on his cock. He lets out a mournful whimper, “Da-” His words stop when I slap his cock for a third time.
I wait, watching him for a moment, but he doesn’t say anything more, so I go back to circling his rim. After another few seconds, I slip my finger into his hole to the first knuckle. I move on quickly, pushing in until my second knuckle, then wiggle, then push to my third one.
I pull my finger back, and he clenches around me before shouting, “no!”
Slapping his cock again, he groans with frustration, and I guess I wasn’t completely wrong about Chase.
He may be sweeter than I thought without smugness, but he’s definitely a spoiled boy who wants what he wants immediately.
Thrusting my finger back and forth, I add my second, slowly pushing right to the third knuckle, then pulling back, then pushing forward.
I purposely avoid his prostate and scissor my fingers, stretching him.
“I’m ready,” he says, spreading his legs wider. I hum, giving him a third finger, and slowly working up to a quick pace. “I’m ready,” he repeats.
“I would slap your cock again, but it seems ineffective at teaching you anything,” I say. Then slap his cock, causing him to whimper and frown at me. “We might have to stop and give you another proper spanking.”
“No!” He shouts, “I’m sorry, please, daddy, I’ll be good. Just can you fuck me now?”
“What did I say earlier?” I ask while scissoring my three fingers inside him.
“I said please, and sorry, and asked, not demanded,” he answers. “I just really want you. Why are you making me wait?”
“So, you’re properly stretched,” I reply.
“I’m ready,” he says again, “please, daddy.”
I shake my head, “you don’t listen at all, terrible boy,” I tease, pulling my fingers from him.
“I’m not a terrible boy!” He shouts, then repeats himself at normal volume, “I’m not a terrible boy.”
While he’s frowning in thought, I flip him onto his stomach, and he lets out a surprised yelp.
Quickly, I put one knee on his back, pinning him down.
People often underestimate my strength. Just because I have a healthy belly doesn’t mean I don’t work out with weights.
I spank his left ass cheek twice, then spank his right ass cheek.
He whimpers, and I continue, alternating a few more slaps on his already abused ass.
After I stop, looking at the back of his head.
His neck is red, and he’s fisting the bedding.
“Now, are you ready to be good and take my cock?” I ask, massaging his clearly sore ass. He nods and mumbles something into the pillow. “What was that?”
He turns his head, now resting his cheek on the pillow, and repeats himself, “yes, daddy.” His eyes are wet with tears, and his cheeks are flushed red. “I really want you.”
I lean over him, giving his shoulder a kiss before sitting on my heels.
He turns over and lies on his back, facing me.
I shift between his spread legs, then grab more lube to coat my dildo.
After, I wipe away the excess on my bedding before shifting closer and nudging his legs up to his chest. He holds them tightly, spreading them wide with a blinding smile.
I line myself up, letting the dildo tip breach his hole.
Pushing an inch further, I still, watching for a reaction or a wince of pain.
“Keep going,” he says.
“Such a demanding boy,” I remark, pushing in deeper by another inch. If I stop to punish him every time he’s not the submissive, good boy he promised, we would never get anywhere.
“Daddy,” he groans, then looks to be preparing himself for me to pull out and give him another spanking. I push deeper, and he takes me easily, clearly the boy may not have been having sex, but this isn’t the first time he’s done anal. “Thank you!” He shouts after realizing I’m continuing.
I hum, pushing the last few inches into him, then give him some time to adjust. Which he doesn’t want, since he immediately does this awkward shuffling up and down.
I laugh as he lets out a frustrated breath before moving so his legs are wrapped around my waist. He tightens them around me, trying to nudge me to move.
I’ve never had someone so eager to have sex with me, and it’s completely going to my head.
“Chase,” I warn, not well since I can feel my smile.
“Maybe if you give me a kiss, I can be a better boy for you,” he offers with a smile.
“You’re not getting a kiss or a reward for acting so poorly. You’ll be lucky if I let you cum,” I scold lightly, and he looks at me with shock.
“You would do that?” He asks, “you wouldn’t let me cum for being a terrible boy?” I shrug, like he often does, and he gives me a look of dejection. “But…”
“Are you going to be good?” I ask, and he takes a moment before nodding.
“I’m trying to be good, though,” he mumbles.
I lean over him, putting my forearms on either side of his head as he moves his hands to my shoulders.
He rubs up and down, looking at my chest with a slight frown before meeting my stare.
I ignore how he flicks his eyes to my lips while wetting his, and I start to softly thrust into him.
He moans, lifting his head to nuzzle my neck as I pick up the pace.
I pull away, sitting up and grip his hips to lift them off the bed.
Thrusting roughly into him, I watch him just stare at me with open adoration.
He runs his eyes down my body, then asks slightly breathless, “can you cum like this?”
I start to explain, “yes, there’s a small vibrator-”
“But I won’t get to see you cum,” he says, and I snort. “I want to see you cum.”
“You will,” I reply, then realize I hadn’t even started the vibrator, too focused on him. It feels odd to reach over to my side table to grab the remote, since I’ll most likely have to pull out. He squeezes my waist with his legs, and I notice that I’ve stopped moving.
“Why aren’t you focusing on me?” He asks, then kicks me with the back of his heel on my ass. “Daddies pay attention to their boys,” he says, then squeezes me again, forcing me to give him a mini thrust.
“And boys actually listen to their daddies,” I argue back, and unhook his legs from my waist. “Boys are good, and when they are, their daddies fuck them until they cum. But you know what terrible boys get?” He frowns at me as I force his legs away from me. “They get nothing.”
I climb off the bed, and he looks at me with utter shock.
As much as it’s fun to have him test boundaries and be a bit of a pushy baby, he needs to learn that’s not how he gets what he wants from me.
If we’re going to be in a relationship, and I don’t nip this behaviour in the bud, he’ll be uncontrollable because I let him get away with everything in the beginning.
He watches me, and it isn’t until I tug off the harness that he reacts with panic.