Chapter 34: A Gentle Union

As Silky had deemed that Jason was stretched enough, he took his fingers out of Jason's hole, his eyes never leaving Jason's face as he searched for any signs of discomfort. He poured some lube onto his hand, his movements slow and deliberate, and lathered his cock up, the slick sensation a stark contrast to the gentle stretching that had come before. With his cock prepared, Silky lined it up with Jason's hole, his heart pounding in his chest as he steeled himself for what was to come. He took a deep breath, his eyes locked onto Jason's, and slowly began to push in. Jason's eyes widened, his face scrunched up in concentration, as Silky's cock breached his entrance. Silky paused, his body still, as he waited for Jason to adjust to the intrusion. Jason whined, a soft sound that tugged at Silky's heartstrings, and Silky immediately stopped, his cock still partially inside Jason's hole. "You okay?" he asked, his voice low and gentle. Jason nodded, taking a deep breath, and Silky could see the tension in his body begin to ease. Silky smiled reassuringly and slowly began to push in again, his cock gliding deeper into Jason's hole. Jason winced, his eyes flashing with discomfort, and Silky paused once more, letting Jason adjust to the sensation. This dance continued, Silky pushing in slowly, pausing when Jason showed signs of discomfort, and waiting for him to relax before continuing. It was a slow and gentle process, but Silky was determined to make it as painless as possible for Jason. He could feel Jason's body adjusting to his, the muscles relaxing as Silky's cock glided deeper into his hole. As Silky continued to push in, Jason's expressions changed from discomfort to a sense of resignation. He was still tense, but it was no longer from pain; it was from the unfamiliar sensation of Silky's cock inside his body. Silky could see the trust in Jason's eyes, the faith that Silky would take care of him, and it filled him with emotion. Finally, Silky's cock was fully inside Jason's hole, and he paused, his body still, as he let Jason adjust to the sensation. Jason took a few deep breaths, his eyes locked onto Silky's, and Silky could see the tension in his body begin to ease. Silky smiled reassuringly and leaned forward, his lips brushing against Jason's as he began to move, his cock gliding in and out of Jason's hole in a slow and gentle rhythm.