He probably wouldn't have allowed anyone to do this to him before either. It requires a certain amount of trust that Dean can't afford to put in his one night stands.

The construct in front of him rocks his hips forwards to drive himself in, matching Gabriel and the other construct's pace. Gabriel starts pinching Dean's nipples telekinetically, in an effort to help push him over the edge far enough to lose his mind, even if he can't actually come yet.