Roland said nothing to that, but slowly withdrew his fingers, leaving a generous amount of the lube inside her. This time he coated three fingers with the lube, liberally, and pushed them into her. Her anus made the briefest resistance to this new, more challenging intrusion, and Teresa wriggled briefly on the desk. Roland said, “You all right? Comfortable?”

She smiled, which he wouldn’t see, then nodded. “You take a lot more care than Julian, that’s for sure. He just whacked it in. Poor Tessa. Though there was a hot side to that… On paper, anyway. And the last boy who had his cock up my arse wasn’t all that much better. So I feel cared for. Sir. You can be rougher with me if you need to be.”

“You’ll know when I need to be.” He pushed his fingers further into her muscled tube, past the second knuckle, and held them there for several moments. Then he pushed the fingers all the way inside her, as far as they would go. Her hips moved, and began to churn, back and forth, fucking his fingers while he held them deep in her.

But he withdrew at last, pressing a thigh against hers to make up for that absence, and lubed his cock. He pressed the head against her lube-glistened entrance, then held still. Teresa, still bent over his desk, raised her arse for him and tightened her hands into fists. She knew she was shaking lightly, trembling under him. It wasn’t fear. 

At last she made a questioning noise. Her anal muscles had accepted the head of his cock, and were holding it, tight but comfortably enough; but he wasn’t pressing forward. She wondered how much willpower that took. He said, “Would you like me to fuck your arse, Teresa?”

She made a gurgle of frustration and impatience. So he smacked her again. She was out of her floaty space, so the blow hurt and she yelped. She tried to push back, to impale herself on his cock, and he smacked her again, more firmly.

“Well? I asked you a question?”