If Matt was worried about Cass taking this seriously, he probably wouldn't have liked the face Cass made when he felt Matt's cock pressing into him: an almost-pained, squeezed-up expression that came with a short, involuntary groan.

Just past the point where it turned painful, Matt backed off and started making it easier, though only enough that it was right on the other side of not hurting. Cassidy felt his head tipping back, breath deepening to help him ride out the feeling of being stretched.

"Christ," he exhaled with a grunt. He did what he could to help make his descent steady and slow, although it meant the muscles in his legs started to burn after a moment.