Jess was in university and about to turn 21, and to make a little extra money she often baby sat for Rachel, a single mom with a young daughter named Sarah. A few months earlier, Jess began to think that Rachel was being flirtatious toward her. It began one night when Rachel invited Jess to stay for a glass of wine and then changed into a sleeping tee that barely covered Rachel's bum and showed off her fulsome breasts. A few times, Rachel bent over or sat with her legs in a position that gave Jess a peek at her body. After that evening, Rachel regularly poured some wine for them. and when they chatted Rachel would put her hand on Jess's arm or knee, and even once on her thigh.
Jess was certainly curious about, even attracted to women, and, after being seduced by her best friend's older sister, Jess had petted and a little more with two other girls, as well as having experiences with a few boys. She found Rachel sexy in an "older woman" kind of way; but Jess was afraid she was imagining things, so she forced the thoughts out of her mind. Jess liked Rachel and her young daughter and did not want to do anything to jeopardize her babysitting job.
Jess was left wondering until a recent Saturday. That day, Rachel said she would be an hour later coming from work and asked if Jess could stay until 1:00 am. Jess agreed, but Rachel got home at about 12:15. She insisted on paying Jess until 1:00 and poured two generous glasses of wine. After remarking how stressful her week had been, Rachel headed to her bedroom to change. When she came out, she was wearing a deep v-neck tee that barely reached the bottom of her butt and obviously had taken off her bra. When Rachel went to the kitchen and reached into her cabinets, the tee lifted, exposing her rear and pink t-back panties. After puttering around a bit, Rachel sat back down on the sofa near Jess, and Jess could see Rachel's nipples poking hard against her tee.
Rachel soon turned the conversation to more personal things by saying how hard it was to date as a working single mom, and she confided that she felt more awkward now "playing around" than she did when she was a teenager. Rachel refilled her wine glass, topped off Jess's glass, and kept chattering away, saying a single mom at her age had no chance to keep men interested beyond two dates without "a blow job and then some." The comment flustered Jess a little, and then Rachel put her hand on Jess's knee and said with a chuckle, "I'm thinking of trying the lesbian thing, do you know any hot girls looking for a mom willing to put out?"
It was an unseasonably warm spring night, so Jess had worn a peasant top and shorts. So, she was even more flummoxed feeling Rachel's warm hand on her bare leg. Jess blushed and mumbled something about Rachel being "pretty" and that she definitely would find someone special soon. Rachel kept her hand on Jess's knee and thanked her.
I hope you're right, Jess," she said quietly. "Is there anyone special in your life?"
"Not really," Jess said. After a pause, she added, "Well, maybe one or two people that I'd like to get to know better."
"Oh, you have to tell me more," Rachel teased, and her hand moved just above Jess's knee.
"Well one is a boy in my Literature class. We've chatted a few times, maybe even flirted I guess, and I can tell he's interested. So, who knows?" Jess said, finding it easy to confide in Rachel.
"And who's the other Prince Charming," Rachel said playfully. Jess paused for a second, suddenly a little less confident. But the wine, and maybe Rachel's hand on Jess's thigh, had an effect.
"Well, actually it's a girl," Jess said quietly but without reservation. "She works at the coffee shop with me, and she is amazing."
