SSS Awakening: Conquering Worlds with My Cupid System

Anna didn’t wait. She leaned forward and took him into her mouth in one smooth motion, her lips sealing around the head. Silas’s head fell back, a guttural groan escaping his throat. The heat of her tongue was wet and insistent, tracing the ridge of his cock as she sank lower.

"Fuck! Miss Anna!"

She hummed in response, the vibration traveling straight through him. Her cheeks hollowed as she sucked, her head bobbing slowly at first, then picking up a rhythm. Her hand worked the base of his shaft, twisting and pumping in counterpoint to the motion of her mouth. Spit pooled at the corners of her lips, glistening in the light.

Silas’s fingers found her hair, tangling in the soft strands. He didn’t pull, only held, grounding himself in the sensation of her mouth working him, taking him deeper with every stroke. She gagged but didn’t pull away. Instead, she pushed through it, her throat opening to accommodate him.

"Look at me," he rasped unconsciously, his eyes glowing slightly, barely noticeable.

And she did. Her eyes, dark and lust-blown, met his as she took him to the base, her nose pressing against his pelvis. She held there for a moment, her throat clenching around him, before pulling back with a wet gasp.

"You taste so good," she said, her voice wrecked. "I could do this all day."

"Prove it."

She smiled, a filthy, knowing smile, and dove back down. This time, she was faster and more aggressive, her tongue swirling around his cock like she was trying to memorize every inch. Her hand cupped his balls, squeezing them gently, and Silas’s hips bucked involuntarily.

"Shit! Miss Anna, I’m close-"

She pulled off with a pop, her lips slick and swollen. "Not yet."

She proceeded to wipe her mouth with the back of her hand and stood up, her knees popping. "I want to try something."

She unbuttoned her dress with quick, efficient movements, letting it fall open to reveal her breasts. They were full and heavy, tipped with dark nipples that were already hard and glistening. She climbed onto his lap, straddling him, her knees pressing into the leather of the chair on either side of his thighs.

"Lean back," she ordered.

Silas obeyed, his chest heaving. She pressed her breasts together, sandwiching his cock between the warm, soft flesh. The sensation was electric; the smoothness of her skin, the friction of her nipples brushing against his shaft. She began to move, sliding her tits up and down his length, the head of his cock emerging from the top of her cleavage with every upward stroke.

"Look at that," she breathed. "Your cock between my tits. Isn’t that beautiful?"

"Fuck, yes!" Fortunately, the distance between her door and the main part of her office was a bit wide, not to mention outside, or else everyone would’ve heard what was going.

She leaned forward and licked the tip every time it appeared, her tongue flicking across the slit, tasting the pre-cum that beaded there. Her rhythm was steady and practiced; she knew exactly how to angle her body, how much pressure to apply, and how to drive him wild.

"That’s it," she murmured. "Let me take care of you. Let me make you feel good."

Silas’s hands found her hips, guiding her movements. The wet sound of her tits sliding along his cock filled the office, mingling with her soft moans and his ragged breathing. The head of his cock was slick with her spit, glistening as it pushed through her cleavage.

"Miss Anna... I’m going to-"

"Not on my face," she said quickly. "I want it on my tits."

She squeezed her breasts tighter around him, increasing the pressure. Silas’s hips stuttered, his balls drawing tight against his body. He watched, mesmerized as his cock disappeared between her tits one last time, and then he was coming, hot ropes of cum spilling across her chest, painting her skin white.

She didn’t stop moving. She kept sliding her tits along his shaft, milking every last drop, smearing his cum across her breasts until they were glistening and slick.

"Fuck," Silas breathed, his body slumping against the chair.

Anna sat back, still straddling him, and looked down at herself. A satisfied smile spread across her face. She dipped a finger into the mess on her chest and brought it to her lips, licking it clean with exaggerated slowness.

"Thank you," she said, her voice soft. "That was exactly what I needed."

But if she thought they were done, then she was kidding because Silas’s dick was anything but soft. In fact, it had become harder, and... thicker.

"You wa-" 𝒻𝘳ℯℯ𝑤ℯ𝒷𝘯ℴ𝓋ℯ𝘭.𝑐ℴ𝑚

"My turn," Silas said in a deep voice, causing Anna to shiver unconsciously. Before she could react, he shoved his hands under her thighs and raised her slightly. "I’m sure you are not a virgin..."

"No, why?" Anna was confused by his question for just a moment when she felt something poking her wet pussy through her panties.

"Wha-" she shivered again as her mind instantly processed what was happening, but it wasn’t that quick. She felt her panties moving to the side and her wet and dripping pussy making contact with the tip of something hot.

"Wai- ANNGH!" She quickly helped her mouth, trying to suppress the moan. The penetration was immediate, and she could only pray that someone wouldn’t hear it. But it seemed like her prayer wouldn’t be answered.

Knock. Knock.

"Miss Anna? Are you alright? Do you need help?" a male voice sounded from behind the door, causing her eyes to widen. Her cry had been really loud.

"I am- An-" she tried answering, only to close her mouth and clamp it tight at the last moment. That was when she realized that Silas’s full length wasn’t even inside her. She looked down at him with an apologetic gaze and shook her head, but the smile on his face made her shiver for the third time in fear and pleasure. She instantly orgasmed.

"Miss Anna?" the voice sounded from behind again, making her look at Silas again.

"I- fuck! Am... alright. Do n’t-angh ~ worry~" Anna found it hard to speak, as anytime she tried to, Silas shoved her down and down his dick.

"We are just getting started," Silas said with a wide smile as the system’s screen flashed in front of him.

[+5 EXP Gained!]

[+5 EXP Gained!]