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The Proper Way of Pleasure

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Tom was packing his briefcase for the day when Kevin stopped in the doorway of his study.

“Do you have a minute, Dad?” Kevin asked, taking a deep breath.

Tom smiled at him. “For you, kiddo, I’ve got all the time in the world.”

Kevin hesitated. “Well, it’s kind of an odd request. It’s just . . . well, you know how I’ve been dating someone recently?”

“Don’t tell me you’ve decided to elope?” Tom teased his son.

“Dad!” Kevin protested, before continuing. “Things are getting kind of serious really fast, and I just—I’m not sure if I really want to go all the way with this person or not. But I do know that I really, um, well.” He swallowed. “I want my first time to be with someone I really care about.” He raised his gaze to meet Tom’s. “So, I was wondering . . .”

Tom blinked. “You want to give your virginity to me?” He couldn’t help but be thrilled at the prospect.

“Yeah.” Color rose in Kevin’s face. “I just don’t want to lose it with someone else and then have him run out on me. But you’re the one man in my life I know is never going to leave me, so I figured you would be the best option.”

“Oh, sweetheart.” Tom crossed the room and pulled Kevin into his arms. “I’m flattered that you chose me. Of course I’ll do that for you.”

“Thanks,” Kevin said, still blushing. “But, Dad?”

“Hmm?” Tom pulled back to look at his son.

“I think sooner would be better than later,” Kevin told him, obviously embarrassed.

Tom chuckled. “Eager, are we?” He laid a gentle kiss on Kevin’s forehead. “I’ll home late tonight, around eleven.”

“I’ll wait up for you,” Kevin promised.

“All right.” Tom gave him one last embrace. “You’d better get off to school now. I don’t want you to be tardy.”

Kevin nodded. “Thanks again, Dad. Bye.”

“Love you. Take care,” Tom told him, watching him go.

The request hadn’t been expected, but Tom was grateful for it all the same. If Kevin was still a virgin, then Tom still had the opportunity to demonstrate how he deserved to be treated in bed. What man was better suited to demonstrating how he should be loved and cared for than his father, the one man he could trust forever?

The loss of virginity was an important milestone for a teenager, and there was no way Tom could rely on some unknown lover to properly satisfy his son. It was part of his duty as a father to ensure that Kevin’s first time was the best experience possible.

That night, he found Kevin waiting for him in the master bedroom, shirtless but with the duvet apprehensively drawn up to his chest.

“Welcome home, Dad,” Kevin said with a self-conscious smile. “How was work?”

“Long,” Tom replied briefly, stripping off his clothes and joining Kevin on the bed. “I’m glad it’s over, because now I get to see you.” He pulled Kevin into a deep kiss.

For several moments the embrace continued, and Tom luxuriated in the warmth radiating off of his son’s body, loving the feeling of his heated skin. When they finally broke apart, Kevin was panting for breath, his face flushed and his hair dishevelled. Tom could feel the blood rush straight to his groin at the sight.

“Kevin,” he said roughly, wrapping his arms around him. “You’re sure you’re ready for this?”

“Yeah.” Kevin tried to catch his breath. “I really, really want you.”

“All right.” Tom gently stroked Kevin’s hair. “If you ever need me to stop, just say the word, okay?”

A soft blush crept up Kevin’s cheeks even as he nodded. “I will. But you don’t have to stop unless I actually say so. I would kind of like it if even were a little bit . . . aggressive and, um, commanding, you know?”

Tom barely kept his eyebrows from rising even as he agreed. So, his son wanted it that way, huh? He was more glad than ever that Kevin had chosen to entrust him with this task. “Duly noted.”

Kevin looked up at him, slightly uncertain. “But, um, could you make sure to be careful all the same?”

Tom smoothed back his son’s hair, giving him a kiss on the forehead, even as he pulled away the covers to tug down Kevin’s drawstring pants. “I wouldn’t dream of being anything less.”

He removed the last item of clothing separating Kevin from him, drinking in the sight of his son’s bare form. With a reddening face, Kevin moved to cover himself, but Tom stopped him.

“Don’t be ashamed,” he told Kevin warmly. “I love seeing how beautiful you are.” He traced a finger down Kevin’s clavicle to his abdomen, loving the smoothness and tightness of his son’s body. Lord, Kevin was so enticing when he looked like this—color in his cheeks, shyness in his eyes, and a glow in his skin. He was the absolute picture of a virgin youth who knew he was about to be thoroughly debauched.

“So beautiful. So perfect,” Tom murmured affectionately.

Leaning forward, he lavished Kevin’s nipples with attention, dragging his tongue along one and then the other, teasing the nubs ever so slightly. Delightful moans slipped from Kevin’s mouth as Tom continued his attention, vigorously kissing and licking his son’s chest. Focusing on the right nub, he latched onto the bud and sucked for all he was worth, listening in satisfaction as Kevin lost the ability to form words. He didn’t lessen the intensity for an instant until he abruptly switched to the left side. As he did, he reached over and gave the abandoned nipple a sudden pinch, bringing Kevin’s panting to escalate into a keening cry.

While Kevin was still gasping for air, Tom moved down his body, kissing and licking the most sensitive areas. He planted kiss after kiss on his lower abdomen and then his inner thighs, careful to not even so much as brush against Kevin’s cock. Running his tongue over the smooth flesh, he waited until Kevin immersed in pleasure, letting out a constant string of moans, before giving the soft skin a sharp nip. The sudden pain caused Kevin to yelp with surprise.   

Tom leaned in to make sure his breath tickled Kevin’s ear. “The sounds you make are absolutely incredible. If only I could have you in bed all day, everyday.”

Kevin’s blush deepened, and Tom decided to have mercy on him by moving things along—not that he wasn’t eager to get to the main event himself.

Reaching under one of the pillows, he withdrew a bottle of lube. “Get yourself on all fours.”

Hesitating, his son seemed to struggle with nervousness. “Dad, I don’t know . . .”

“It’s all right,” Tom reassured him. “I’m here to teach you. I understand that you’re new at this.” He pulled Kevin forward, placing a soft kiss on his jaw. “Now, get down on your hands and knees.”

Once he had Kevin in position, he couldn’t help but smirk as he spread lube on Kevin’s tight entrance. His hole was narrow and very obviously unused. He was going to enjoy being the first one who ever was there.

The first finger entered easily, and Tom entertained himself by thrusting his finger in and out, mimicking sex, savoring the tightness of the untried muscle as Kevin let out small mewls and soft gasps.

When Tom inserted two fingers, Kevin inhaled sharply.

“Easy, easy,” Tom soothed, rubbing Kevin’s back comfortingly he twisted his fingers inside Kevin. “I know you’ll be able to cope with this.”

“It feels strange,” Kevin admitted, even as he cautiously pressed back against Tom’s knuckles.

Tom chuckled. “Well, I’m glad for that.”

The comment brought Kevin to blush and duck his head, not raising it again until Tom added a third finger. “Dad!”

“Don’t brace yourself,” Tom warned as he flexed his fingers, bringing Kevin to jerk. “That will make the stretching more painful.”

“It—I don’t know—stings,” Kevin said desperately. He opened his mouth as if to continue, but Tom twisted his digits once more, transforming whatever Kevin was about to say into a sharp, wordless cry.

He didn’t continue to stretch Kevin for very long; he wanted to leave some surprises in store for Kevin. After all, he only had one virginity for Tom to take. “I think you’re good,” he murmured into Kevin’s ear, smirking as Kevin shivered at his words.

Settling himself against the headboard, he eased Kevin into position, guiding his hands to rest on his shoulders and placing his legs on either side of his hips so that he would be facing Tom. He wanted to watch his son writhe on his cock, barely able to cope with the sensation of taking his first dick.

And sure enough, he got his wish.

Kevin’s eyes widened as the tip of Tom’s cock pressed against his entrance. “Th—that feels really big.”

“You’ll be all right,” Tom comforted him, gripping his hips firmly. He couldn’t help but enjoy the contrast of his own large, calloused hands on Kevin’s smooth skin, right by his thin waist. The display of his own power, the ease in which he could take control, sent a thrill zipping through him, and fresh rush of heat flooded his groin.

With a soft groan, he pushed inside of his son, reveling in the sensation. Lord, Kevin was tight—being inside him was like a vise.   

Kevin apparently thought so, too.

God!” He gasped. “That’s—that’s—”

“That’s just the head,” Tom informed him, amused, before giving him a second thrust and then a third.  

Kevin’s breathing hitched, and his mouth moved, but only strangled syllables emerged. Already shaking with nervousness, he began trembling violently as Tom pushed further and further into him. Tom could already feel Kevin’s hole spasming around the large intrusion.

“Take a minute and just relax,” Tom instructed, caressing Kevin’s jaw. “You’ll adjust to me, don’t worry.”

“You’re—you’re already so big,” Kevin panted. “I don’t know if I could ever get used to you.”

“You’d be surprised,” Tom told him fondly, before feeding Kevin another thick inch.

From the expression on Kevin’s face, he had just realized just what it was going to feel like to take all of Tom. “Dad,” he managed through his pants and moans. “Maybe this wasn’t such a good idea.”

“No, you’re doing fine,” Tom reassured him, pushing in deeper and enjoying Kevin’s gasp. “You just need to relax, sweetheart.”

No parent liked to see their child in pain, but Tom couldn’t deny how arousing it was to see his son splayed out before him, naked and perspiring, struggling to take his cock. He could feel Kevin’s arms and legs shaking from the strain and the sweat rolling down Kevin’s back. He relished into being able to so easily take control, to render his son helpless and mewling, to force him to endure pleasure and intensity never before encountered.

“How does it feel?” Tom asked as he moved ever further inside Kevin.

Kevin did not respond. Noticing that his son was biting his lip to stifle his moans, Tom gave a sudden, sharp thrust, making sure to spear in deep.

God! ” Kevin whimpered, but Tom wasn’t finished. Two more times he rammed into Kevin suddenly, as deep as he could go in one push

“When I ask you you a question, I expect an answer,” Tom told him, his tone firm, gently tilting Kevin’s chin up to force him to meet his eyes. “Tell me: how does it feel?”

“It aches,” Kevin told him, color evident in his face. “Sometimes it stings. I can really tell that you’re stretching me.”

Tom kissed his temple. “There we go. Isn’t it just better to talk?”

Kevin opened his mouth to reply, but when Tom pushed into him once more, the only noise coming from his throat was a long, thready moan.

Smirking, Tom realized he had hit Kevin’s prostate, and thrust against it several more times in quick succession, loving the sounds Kevin made.

Oh!” Kevin gasped, throwing his head back, his hair catching the light. “Oh, oh, oh!

Tom laughed softly. “Glad you like that, son.”

His next thrust pushed his cock in past Kevin’s prostate, brushing against it but not hitting it with full force, and Kevin was back to squirming and whimpering with discomfort as Tom’s cock forced him open.

“Dad, you’re too big,” Kevin protested. “I’m not going to be able to take all of you!”

“Don’t worry. You can.” Tom reached out and stroked Kevin’s cheek softly as he gave him another thrust. “And I think you’ll enjoy it.”

“Oh, Dad,” Kevin groaned, no doubt feeling the sear of stretching beyond his limits as Tom drove deeper and deeper inside him.

“You’re doing so well,” Tom soothed him. “Just accept what I’m giving you, Kevin.”

“I don’t think I can!” Kevin let out another cry as Tom continued to press inside of him.

“We’re almost done,” Tom told him, without pausing in his movements. He knew Kevin must be full to bursting; Tom’s cock was huge for anyone to take, let alone a virgin like his son. “Just a little bit more. You’ll be all right, you’ll see.”

“It’s too much!” Kevin exclaimed. “Oh, God, Dad! It feels like you're splitting me in half!”

Tom could feel Kevin’s walls clenching tightly around him and was unable to hold back a groan at the intensity of the feeling. “Just trust me,” he said roughly, even as he drove deeper into Kevin.

“Dad, I can’t—oh! You’re too big—God! I can’t take it all—Dad! Oh, Dad!” His words continued to break off into wails as Tom filled him with even more of his length. “God, you feel so huge!”  

“Almost there, darlin’,” he murmured into Kevin's ear, relishing in how he was able to make his son come positively undone. Never before had he seen him like this, warm, pliant, and moaning, but damn if he didn’t like the sight.

“Dad, I—Dad—” Kevin could barely form a coherent sentence, only clutch desperately onto Tom’s broad shoulders as Tom bucked up into into him. “Too much—you’re too big!”

“Don’t worry,” Tom said as he fully sheathed himself inside of Kevin with one final thrust, savoring in the heat and tightness of his son’s body. “You made it, son.”  

Thoroughly impaled, Kevin remained still on Tom’s lap, gasping for breath, his fingers clenching on Tom’s shoulders and his eyes pupils dilated wide. He was absolutely stuffed, and he certainly looked like it, his hair in a disarray and his entire body trembling.

“Oh my God,” Kevin managed. He reached a shaking hand behind him to lightly touch the base of Tom’s shaft, as if making sure it was actually inside him. “I can’t believe . . .”

“And to think you didn’t trust me,” Tom admonished gently. “What does it feel like to my cock inside of you? The one you never thought you could possibly take?”

“Full,” Kevin said, his cheeks darkening even further. “Very full.”

Tom gave him a gentle kiss on the forehead. “What do you want, now, sweetheart? What should I do with you?”

“I want—” Kevin hesitated before shyly continuing. “I want you to fuck me. Just hold me down and press me into the mattress without stopping.”

“You sure you want me to be rough with you some more?” Tom asked, brushing his fingers through Kevin’s hair. “Wouldn’t you like some TLC instead? Something slow and gentle?”

“No. I want you to show you that you own me,” Kevin breathed. “Just take what you want and don’t worry how I’m doing."

“Your wish is my command, sweetheart.” Easily flipping Kevin onto his back, Tom draped his son’s body with his own, pushing him deep into the mattress, holding him down so he could maneuver him however he pleased. “You ready for this?”

“Please, please, give me everything you have,” Kevin begged despite the blush staining his cheeks.

“You got it.” Tom pulled him into a deep kiss before withdrawing and then plunging into him again.

Kevin gasped at the sensation of being so thoroughly and suddenly.filled, but Tom just continued driving in and out of him at a speed that had both the bed and his son shaking beneath him. The furious pace left Kevin breathless, incapable of doing anything but moaning and gasping helplessly beneath Tom.

“You like this, Kevin?” Tom demanded as he ruthlessly hammered into Kevin. “You like me pinning you down? You like me taking control?”

The only response he received was a sharp cry from Kevin, and Tom realized that with his frenzied thrusts, he had again rammed into Kevin’s prostate. Wanting to extend his son’s pleasure as long as possible, he slowed his movements, now sliding in slowly, carefully only just nudging the spot

“I think you like being at my mercy,” he growled, as Kevin keened at the sudden absence of pleasurable contact. “I think you like not being allowed to object, not being given a say in what happens. But don’t worry. I’m here to take care of you, and I will take care of you.”

With that, he resumed his relentless pace, Kevin’s frantic cries driving him closer and close to the edge. But Tom was determined to do right by his son, and he made certain he held off his climax until Kevin achieved his own. It didn’t take long; with Tom pounding away at his prostate, Kevin’s climax hit sudden and hard, and he let out a long wail, shuddering violently from the intensity of it. Only then did Tom let himself go, pumping his seed deep into Kevin’s body, claiming him.

Collapsing back against the mattress, Tom pulled Kevin close and wrapped his arms around him. “Are you okay, Kev?”

“More than okay,” Kevin replied, weary but obviously happy, as he curled up against Tom, resting his head on his chest.

Tom ran his fingers through Kevin’s hair. “Whatever you want, whatever you need, you can come to me. Just let me know what it is, and I’ll make sure I provide it.”

“Thank you, Dad,” Kevin murmured, closing his eyes as he cuddled against Tom.

Tom gave him a gentle kiss on the forehead. “You’re welcome, son.”