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Chapter 18
by
Zingiber
Can Gary help his girlfriend? How?
"Please put a finger in my butt?"
Bernie raised her head to her mother. Her forehead was damp and her cheeks were flushed pink as she paused in her grinding into the long pillow. "M-mom?" she asked. "I'm almost there, mom. Please put a finger in my butt."
Gary's eyes widened. Bernie's mom helped her that way? Had she forgotten he was there?
Joyce answered dreamily from her chair, "Perhaps your young man could help?"
"Ooh!" said Bernie, remembering. She looked up at Gary pleadingly, embarrassed, aroused, and needy. "W-would you?" Her glasses flashed at Gary.
"Uh..." Gary stammered. "Okay." He felt a stab of guilt and blushed. Just last weekend he was eating out Mrs. Sonia Rubin, his summer employer and his doctor's wife, when she demanded he finger her ass. The busy Dr. Rubin knew Gary was helping take care of his highly sexed wife, but Bernie didn't.
Gary jumped up from his chair, his erect penis bobbing. He knelt on the carpet next to his girlfriend and patted her butt gently. She did have the most perfect, big, peach-shaped butt he'd ever known. "God, your b-, I mean, you're beautiful," Gary said, catching himself before he complimented her butt. Bernie was sensitive about it being too big.
Gary's hand was slick with rose-scented lotion, but he added some clear lube from Bernie's pump bottle. She was breathing fast and deep, her knees apart as she straddled the bolster. The vibrator buzzed underneath her. "Okay, Bernie," he said. He moved his index finger down her rear cleft until it touched her anus. His heart thumped. He'd dreamed of this but never felt brave enough to ask.
"Two," she said.
Gary crossed his middle finger over the nail of his pointer. "Okay."
He felt her ring press out at him, opening, and his fingertips slipped in. She sighed.
"Deep," she said.
Gary pressed his fingers into his girlfriend's hot, slick backside. Her tight ring squeezed his stacked fingers. The vibrator's buzz tingled on his fingers.
"Yeeeess," she groaned. "Oh yes."
Gary smiled. Anal fingering seemed to be working well for Bernie, just as it did for Sonia. And for his very first lover, Meg.
"Touch yourself?" Bernie said.
Gary put his other hand on his cock. "Yes."
The wet sound of his stroking hand made Bernie smile. "Yes," she said.
"Oh, Bernie," Gary said. He stroked his cock as his other hand fingered her ass, tight, deep, and hot.
"Ahhhhh," she sighed, pressing down into the long firm cushion, feeling the vibrations more deeply. "Yes. Yes. Come with me, lover, yes..." Bernie's hips started to pump as her orgasm finally caught her. Her glasses fell off onto the carpet, and her mouth opened with a loud groan of pleasure. Her dark curly hair tossed as her head bucked. Her toes curled and stretched.
"Uhhh!" Gary groaned as his cock exploded, shooting silver seed across the skin of her golden back and buttocks. "Yes, yes, yes!"
Bernie clicked off the vibrator to savor the glow of her orgasm.
"Out," she said.
Gary slowly withdrew his fingers, his knees trembling. "Oh, wow," he said. "Oh wow. Thank you."
"Th-thank you," Bernie said. "So good."
Gary gently patted a towel across Bernie's back to mop up his semen. Looked like it was a big load. He looked up to see Joyce Bernstein beaming at him and her daughter.
"It was beautiful to see the two of you together," she said. "I hope you're always so good to her, Gary."
Gary swallowed. "Thanks. Guess I need to get going before the women start showing up for the Circle," he said. "Um, hope my sister has a good time."
He kissed Bernie's cheek and accepted a tight hug from her naked mother, body to body, before tiptoeing out to dress and leave.
Follow Gary or the Pleasure Circle?
When The Cat's Away
Parents' sex cruise lets college kids play until their surprise early return.
Updated on May 20, 2026
by Zingiber
Created on Jul 16, 2003
by Zingiber
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