Matthew blushed at the question. If he would say no James couldn't cum but at the same time strange man would get his satisfaction. He licked his lips not really knowing how to answer James's question.

"I mean, if you don't want me to, I quess we could stop," He said slowly pulling his fingers out.

That made Matthew shiver. He bit his lip and was silent for few moments. At last he decided, feeling bad for James.
"Mhm.. Ok. But.. only this one time. I won't let that asshole blacmail me with you."
But in fact he wanted to cum too and scratch the itch he felt in his hole.

He smiled, and moved up his cock, getting behind him. "Ready," He asked, gently putting the head of his cock into his hole.

Matthew gasped when he felt the head of James's cock going inside. Then, with a little blush, he nodded his head.

"I'll be gentle," He promised, slowly wiggling it into him.

Matthew moaned a little, feeling hard member going inside him while his hard package was tightly hugged by device the strange man installed. James could feel twitching of his hole around his penis.

"So tight," James moaned, pushing in a little harder.

That made Matthew arch his back with another moan slipping past his lips.

"How am I doing," He asked, trying to be gentle.