Offer him a massage

Jessie just watched for a long while, until they were finished, and he was about to leave.

"W-wait!" she blurted out, and he looked at her.

"I feel bad about just letting you go, after you did all that for me."

"Oh," Brian replied, "it was no trouble at all, I was happy to help."

"But you must be tired from all that. I know, let me give you a massage!"

"A massage?"

"Yes." she said, as firmly as she dared, and trying not to sound like she was thinking about his body. "I insist on it, in fact."

Brian decided that Jessie was simply trying to be nice, and there was nothing wrong with that. While he felt like a massage was a little intimate, people got them from strangers all the time. "Alright," he said, "I'd love a massage."

She smiled, and thought where they should do it. "I suppose we have to do it in the bedroom." she decided, as the house was still pretty bare, "head on up and lie down."

He wasn't put more at ease by doing it in her bedroom by a longshot, but he had seen the house, and knew that she had a point. And besides, it would be rude to argue, especially to imply that she had some sort of sexual intentions for him.

He ascended the stairs and lay face down over the blanket, and she climbed on after him. As she did, her skirt slid up, showing him her leg, and he blushed and looked away. Soon, however, he realized that whenever he looked up, he saw up her skirt, or down her dress, or something similar. She was more unguarded than any woman he had ever met, and he felt incredibly guilty for his thoughts when he saw her accidentally exposing herself. He decided to keep his eyes closed entirely, so as not to betray her trust.

Even without looking at Mrs. Goodman, there was a problem. She was not a very strong woman, at least not in comparison to Brian, and her touch felt very little to the strong and firm massages he had been given in the past. It didn't feel like she was kneading his shoulders half so much as caressing them. It was everything he could do to keep himself from becoming erect at once.

Jessie didn't have any idea of Brian's internal struggle, and thought that he simply didn't feel anything from her techniques. She tried leaning over so that her breasts brushed over his neck, but aside from a slight tremble she assumed was surprise, he didn't react.