Use the lube

You consider it but if the man suggested it to make it easier he is probably referring to the abortive attempts you've previously had, and having some way to prevent those. Sure, your skirts will no longer pull his manhood from you, but the rest of the process lacked ease and it is probably best to use this mans superior experience in the matters of 'anal sex'. So you nod and meekly submit.

"Yes, use the lube. Please."

He reaches down to the floor where next to a crumbled pair of three quarter length trousers and pair of dark boxer shorts is a pack of wet wipes and a small cylindrical bottle. His hand snatches up the bottle and he presses some sort of pump at the top of it and a clear gel spews forth which he spools on to his fingers and rubs into the black flesh of his manhood, making it shimmer in the poor light of the room. You can tell from his expression that he is ready so you stand and turn, bending and pressing your buttocks back up against the hole.

You feel something odd against your hole, until you realise it is his fingers and he must be rubbing more lube against your hole. The build up and anticipation is making your heart thump in your throat. His fingers slip away from your ass and a moment later the head of his shaft presses against your rear and burrows into your behind with ease, almost silkily sliding it's way deep into you.

The sensation is so different than before, it is definitely uncomfortable but it is not painful like it was before. It is not the commandment of suffering, you mew out and groan as you realise that this sensation is many things but overall it is pleasurable! The mans speed builds and with it the delight which makes you squeal. You can't allow this to continue, can you? You are supposed to suffer, but you don't know how and this feels good - maybe the discomfort is suffering enough?