Henry leans down, his lips brushing against Riley's in a slow kiss... deep, passionate, almost coaxing, as if he's trying to steal every ounce of thought from Riley's mind and replace it with nothing but sensation which will distract Riley from feeling the mild pain that might come with taking him in.
As he kisses him, Henry shifts his hips slightly, aligning himself perfectly with Riley's entrance, letting the tip of his cock press against him.
The heat, tight and impossibly warm, makes Henry tremble slightly. When he pushes in just enough for the tip to slip inside, Riley flinches immediately, tensing sharply.
His body stiffens, almost instinctively closing up, as though realizing that Henry's cock isn't the same as his fingers. Bigger. Hotter. Fuller. Too much to take all at once.