Courtney kneeled in front of Jeremy on her bedroom floor beside her mother Caitlin. She ran her hand along the length of Jeremy's cock, giggling a bit when it twitched under her light touch. She looked at her mother and asked, "This is going to hurt, isn't it?"
Caitlin said, "For a little bit, but if we can prepare you well, it shouldn't be a big thing and if you're anything like me, the pleasure will be many times greater."
"Uh huh. How do you want me, Jeremy?" Courtney asked, looking back up at the big teen.
Jeremy looked back at Courtney, his longtime friend, and suddenly today his girlfriend. "Um, I've heard it can go better if the girl's on top," Jeremy said. "So let's try that."
Caitlin smiled at Jeremy's words.
Courtney rose to her feet and Jeremy pushed himself back to lie on Courtney's bed. She unclasped the front of her bra and dropped it on the floor, then looked at her mom and peeled down her bright pink panties, revealing her dark blond, fleecy bush. The panties, with their sodden crotch, landed on top of the bra. She climbed on the bed and straddled his hips, sitting down on his stomach. She wiggled her wet pussy against Jeremy's strong abdominal muscles, then rose up on her knees and looked down and back, reaching for Jeremy's cock.
Her mother's hand clasped her reaching fingers. "Easy now, baby," Caitlin said. "I know you're excited, but let's make sure you're as warmed up as you can be, and that you and Jeremy have lots of lube."
"Mom, uh," Courtney said. "I don't think I could GET much warmer." She looked at Caitlin sheepishly. "Before Jeremy came up I was..." She held up a hand with two fingers together and twitched them in the air.
Jeremy felt a warm flush on his face and chest. He had been worried she had been angry. Now he knew that smell was Courtney's aroused juices. He wondered if she'd been thinking of him when she was touching herself.
Courtney continued, "And then we were..." but trailed off before describing the loving clinch that Caitlin had discovered them in.
Caitlin laughed gently. "Well, then. It will go even better if you have an orgasm before he enters you. Girl Scout's honor," she said, raising a hand in the sign.
"Um, okay," Courtney said.
"Let me run and get the lube and a towel," her mother said.
Caitlin returned with a big white towel and a basket holding a fresh, sealed pump bottle of Liquid Silk and a few other items. Jeremy and Courtney were lying nude on the bed, holding hands. Courtney was giggling sheepishly and looking bashful, with a pink blush on her face. Jeremy's cock was erect and slowly weeping clear fluid.
"Is everything okay, sweetie?" Caitlin asked her daughter.
"Um, I just told her how pretty she looks," Jeremy said.
Caitlin raised an eyebrow at Jeremy, then glanced at her daughter. Courtney put a hand over her mouth to stifle her helpless giggles. Caitlin suspected Jeremy's compliment had been more explicitly sexual.
"Do you think you could finish up the way you were doing earlier?" Caitlin asked, curling her fingers in the rubbing motion Courtney had made instead of saying the word "masturbating". She glanced at Jeremy, doubting whether the young man had the touch yet.
Courtney looked a little uncertain.
"May I help, sweetie?" Caitlin put down the basket and clasped Courtney's other hand.
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