1. Valentino’s First Time #2
Oswald cupped Valentino’s cheek and slowly, carefully bent his head. Inch by inch, he brought their lips closer. Then he softly nipped, once, twice. Valentino gave out a broken moan.
Their tongues touched, and Oswald could have burst into flames from that first taste alone. He let himself be lulled by the perfect fantasy of the innocent eighteen-year-old omega who wanted to give himself to him. He guided the clumsy virgin until the kiss deepened and turned dirty.
He broke off a minute later, and Valentino panted against his lips.
“I want to be touched. I want to know how it feels to…to make love.” His hot breath fanned Oswald’s face. “Will you do it? Will you teach me?”
“Come with me.”
Oswald took Valentino’s hand and strode through the crowd, straight to the elevators and down to the garage. True to his role, Valentino stood in the elevator car, hunched over and nervous, sneaking shy glances at him. Oswald hugged him to his chest, and the boy sighed, nuzzling his shirt.
The tiniest smirk escaped Valentino when Oswald’s silver Aston Martin lit up at the press of his key. Oswald opened the passenger door for him, and Valentino climbed inside.
“It’s a beautiful car. My father has one just like this but dark blue.”
“What does your father do?”
“He’s in finance.” Valentino looked outside at the passing city lights. “You can never tell anyone about this,” he said in a shaky voice. “Please?”
“I won’t. I promise.”
He nodded and took a shuddering breath.
“I’ll bring you pleasure, angel, so much pleasure. It’ll be our secret.” Oswald placed a hand on Valentino’s thigh and stroked it gently. Then he turned his hand palm up, and the boy took it, interlacing their fingers.
Watching Valentino deep in his role, visibly trembling, Oswald wondered if he’d been too hasty in inviting the omega into his home.
None of his enemies could have sent the boy as bait because nobody, not even Oswald, had known where he’d be tonight. He most definitely hadn’t been followed, and the omega had already been at the club when he’d arrived.
But if Valentino ever decided to make a living as a con artist, he’d be most successful.
Afraid the fantasy would slip between his fingers, he guided his beautiful conquest straight to his bedroom.
“Do you want something to drink, sweetheart?”
Valentino shook his head, his lips parted, as he looked around the room. Oswald crouched at his feet and caressed his hips.
“We don’t have much time,” Valentino said timidly. “My father might already be looking for me.”
“Do you trust me?” It was a ridiculous question—trust must be earned—but it was perfect for their game about a clueless virgin and his wily seducer. Oswald unzipped Valentino’s pants. “Will you let me take care of you?”
“Yes. I trust you.” The naive reply made his dick throb.
“Turn around for me, beautiful.”
Valentino shuffled around and wrapped his hand around one bedpost.
Carefully, Oswald tugged the white slacks over Valentino’s ass cheeks. What he revealed took his breath away. The most beautiful, youthful fuzzy peach of an ass framed in the pearly white lace of a barely there jockstrap.
He nuzzled the bare crack and brushed his lips through the groove.
Then he painstakingly slowly dragged Valentino’s pants down, tapping on one leg and then the other, pulling them off.
He knelt behind Valentino, his face level with the omega’s crease. A distinct scent of arousal drifted from between those flawless ass cheeks.
“Put one knee on the bed, angel.”
Valentino took a deep breath. He lifted one leg, knelt on the edge of the mattress, and leaned forward. The move opened his crease and exposed his pucker.
Oswald bit back a moan.
Smooth, pink, precious. A tiny dry hole, clenched tight, surrounded by the softest pale skin. He looked one hundred percent the eighteen-year-old virgin he was pretending to be.
“You’re breathtaking,” Oswald murmured and pressed a chaste kiss on the boy’s small, completely hairless balls. He nuzzled higher. Kissed the warm taint. Brushed it with the tip of his tongue. Then he opened his mouth and kissed the sweetest pucker he’d ever seen, swirling his tongue against it.
“Oooh,” Valentino breathed. A shiver went through him.
“Is this okay?” Oswald asked, putting as much hesitation and care into his voice as he could muster. He licked tenderly over the closed furl of sensitive skin.
“I…I think so.”
“You can tell me to stop any time, precious angel.”
“Oh… Okay.”
Oswald kissed and prodded with his tongue, tenderly at first then a little firmer. The little hole remained closed, but Valentino began making small sounds, low gasps and tiny whimpers. Oswald palmed Valentino’s ass cheeks, a perfect fit for his hands, and jabbed his tongue at the clenched rim.
Finally, the muscle began softening up. He could press the tip of his tongue inside and wiggle it.
“Oh my God!” Valentino cried out, pushing his ass back on instinct.
“I’ll make you come with my tongue in your ass, baby boy. You’ll love it. Just relax.”
“Feels so good when you kiss me there.”
“It’ll get even better.”
With that, he peeled the lace jockstrap off.
“We can’t have you getting these dirty.”
He set the underwear aside and delved into Valentino’s hole. Humming, he licked inside, as deep as the tight channel allowed him. So fucking tight! How was the boy doing it? Was he truly a virgin?
It’s a fantasy. A wonderfully realistic one. Let yourself dream.
He worked his tongue deeper, and Valentino moaned, his voice like music. He began meeting Oswald’s licks, pushing his ass into Oswald’s face.
“Oh God! Oh God! I can’t… Ooooh!” He squealed, and his little hole released a mouthful of fresh slick. Oswald drank it and licked some more, tongue-fucking the trembling flesh until Valentino collapsed on the bed, boneless.
The taste of Valentino’s orgasm burned down his throat, making his heart slam against his ribs and his balls hurt. Being gentle and patient was becoming a challenge.
He lifted Valentino under his arms and flipped him onto his back. The small omega was easy to throw around. He blinked up at Oswald, face blotched with pink and eyes half-lidded.
When Oswald removed Valentino’s luxury white top, he revealed a transparent camisole, Valentino’s nipples visible. Oswald brushed one nipple with his thumb through the fabric.
“Do you like having your nipples played with?”
“I don’t know. Nobody has ever done that to me.”
“Do you pinch them when you jerk off?”
A head shake and a blush. “Will it feel good?”
Oh lord. Those quiet, shy questions! Oswald’s dick leaked precum in his pants. “We must try.”
He pushed the camisole up and took one nipple into his mouth. He suckled on the very tip, grazed the nub with his teeth, and sucked some more. Then he switched to the other one. When he sucked harder, Valentino gave out a soft cry of pleasure.
“That’s nice, hmm?” Oswald looked up.
Valentino nodded, biting his lip.
Braced on his arm, Oswald licked one nipple then began sucking it rhythmically. He paused for a second to instruct Valentino to play with the other one. The boy obeyed eagerly, writhing and moaning. His cock was hard anew.
With his free hand, Oswald reached between the boy’s legs, past his balls. He circled a finger around the wet hole. It was softer than before. He easily slid one fingertip inside and began slowly moving it in and out.
Had the boy truly been a virgin, Oswald would have taken hours to tease and torture him. But this was a game. A filthy fantasy.
And he was done being patient.
He pulled out his finger and knelt between Valentino’s spread legs. Big blue eyes gazed up at him, full of anticipation.
Oswald opened his pants and slowly stroked his cock.
Valentino stared at it, mouth agape, fear bleeding from his eyes. When the omega made a move to scramble backward, Oswald grabbed his legs and folded him in half, swiftly lining himself up.
The next second, before his shy little virgin could protest, he pushed at the tiny hole, forcing his cockhead inside.
“Augh!”
Valentino scrunched up his face and panted, digging his nails into Oswald’s pecs.
“It hurts!”
His rim was locked around Oswald’s dick, squeezing him like a fist. It felt absolutely incredible.
This is way too real.
“Breathe through the pain, sweetheart,” Oswald said hoarsely. “It’ll pass.”
“Hurts so much…”
“I know, baby boy. It must. Breathe.”
Valentino’s chest rose and sank, and he slowly peeled his eyes open. Tears escaped from the corners.
Oswald bent over him and kissed him gently, just a brush of his lips.
Then he thrust deeper.
Valentino keened but made no move to push him off. He placed a shaking hand on Oswald’s nape and gasped against his lips. Oswald paused, counting to ten. He was going to lose it in the snug heat of Valentino’s body.
“Does it still hurt?”
Valentino gave one jerky nod. “Not as bad as before, though,” he whispered. “You’re so big.”
“I’ll make the pain go away.”
He pulled out an increment and thrust back in, fucking Valentino with barely half of his length.
Suddenly, Valentino’s eyes grew big, and he stared at Oswald open-mouthed. On the next thrust, he sighed. Oswald pushed only one inch deeper, and Valentino let out a sweet moan.
“Better?”
“Yes. Yes. Oh God.” Another moan. “I’m so full. You’re so deep in me.”
“You’ll take me to the hilt tonight, baby boy.”
“I can’t. You’re too big. It’s my first time… I can’t…”
Oswald silenced him with a kiss and continued feeding his hole with slow, lazy fucks.
When he felt the omega relax a little more, he braced himself above him, watching with contentment the innocent beauty spoiled one thrust at a time.
A deep flush crept up the omega’s chest and spilled into his cheeks.
He whimpered at every fuck, his frail hands clasping Oswald’s upper arms. His forehead glistened with sweat.
His hole remained snug, the smallest, tightest little ass Oswald had ever fucked, but it leaked slick like a faucet, wetting Oswald’s balls.