[Note: A character expresses reluctance and gets overruled. If that's not your cup of tea then this story won't be for you.]
*
Jason, Frank, Harold, and Theo were childhood best buddies whose lives had sent them to opposite ends of the country. But every year without fail, Jason would invite them to his house in Colorado for a week of hiking, fishing, the works. Vanessa's dad loved them like brothers and insisted on hosting the reunion every year.
Vanessa also "happened" to plan another visit home this year that overlapped with the tail end of their reunion.
"Why are you always picking dates when we have guests over! What about family time!" Her mom complained over the phone but Vanessa could tell she was happy.
"Can't help it mom, you know how it is. I'll see you soon."
Weeks later, Vanessa pulled into the driveway just as they were putting the dishes away from dinner. After a round of hugs, her mom pushed her into the kitchen. "You must be starved! I saved you some dinner, go heat it up before you dig in."
It looked like it was her dad's and Theo's turns to do the dishes tonight. Her dad handed Theo a plate to load into the dishwasher and toweled off his hands to give her a hug.
"How's work?" Theo asked.
"It's alright, lots to do," she shrugged.
"She's real busy now that she's gotten that promotion," her dad started and Vanessa rolled her eyes fondly.
When dad turned away to find that wine he'd saved for her to try, she took the opportunity to brush her hand along Theo's arm, scratching her nails through his coarse arm hair. He watched her with a predatory smile.
They had played this game since she'd been in college, ever since she accidentally fell on him and felt his dick twitch under her ass during a picnic by the lake. His hands had pressed a little too long against her soft belly as he helped her up. She hadn't minded it. He had always been the good-looking one of the group, with a strong hooked nose and bright eyes, undiminished by the growing gray in his hair and wrinkles around his eyes. Vanessa found them sexy, actually.
The game had started small, with innuendos, looks, but after she graduated he'd retaliated with a tongue down her throat and a hand up her shirt at the side of a rest stop. She hadn't been able to stop blushing the rest of that memorable hiking trip. Things had escalated year after year, until now she was regularly planning her visit around the entertainment of sneaking around with him. It was just too boring otherwise.
"Later," she mouthed right before her dad turned back.
Vanessa's parents had a guest bedroom, a pullout bed in the basement, and a couch. Every year the men drew lots; this year Theo was on the couch. Vanessa looked forward to it.
She crept down that first night after midnight, avoiding the creaky stairs, dressed in a loose t-shirt and her smallest pair of sleep shorts. It was chilly but she knew she'd get warm soon. Crossing through the living room to the kitchen, she saw Theo's eyes follow her from where he was lying prone on the couch. Pouring herself a glass of water, she took a sip. Then she went to sit boldly across his lap. Under the throw blanket, his thick thighs flexed and she felt his cock start to fill.
"I was wondering when you'd come," he murmured. Fingers snaked through the leg of her shorts, their rough callouses petting the top of a soft thigh, teasing the edge of her panties, before digging into the furred space between her legs without hesitation. It gave her a thrill, the way he always touched her like he owned her. He grunted when he found her already sopping wet.
"You always make me feel so good," she whispered as she leaned back against the couch, legs falling apart to allow him more access. Theo's large hand somehow felt larger when it was trapped in her shorts.
He ran his knuckles along her slit lightly, enjoying the tacky juices flowing out from her pussy. Gathering her wetness, he parted her pussy lips and teased her clit with a few light rubs before pressing harder against the nub, just the way she liked it.
"How's Wendy?" Vanessa murmured. It was dark in the living room, but faintly she could see his hand undulating inside her small shorts. She shifted her ass again so she could do him a favor and trap his cock under her cheeks. He thrust up lazily in reply before freezing at the couch's loud creaking.
"Broke up with Wendy months ago, didn't your mom tell you?" Theo's string of romances was the group's prime source of gossip. "I'm dating Sheila now."
"How's Sheila?" She wriggled a little as he sank his middle finger into the deepest part of her.
"She's fine." He added his index finger and then pumped them. The thick digits explored her as his thumb diddled relentlessly with her clit. The warmth in her belly pooled through her body, and her limbs were starting to tingle.
There were sudden footsteps on the stairs. They both froze. Her heart pounded in her throat and she clenched around his fingers so hard that it almost hurt. Vanessa slapped at Theo's wrist, trying to get him to pull out of her. "Theo!" She hissed. Even in the dark she could tell he had on his shit-eating grin. The bastard kept his hand where it was. She quickly grabbed her cup of water from the coffee table for at least a little bit of cover.
"Vanessa, stop bother Theo, he's had a long day. Go back to bed," her mom said crossly, rubbing her eyes as she made her way to the kitchen. It must have looked like Vanessa was innocently sitting on the couch beside Theo, rather than right over his hard cock. "What a terrible privilege it is to be your favorite." Theo's teeth flashed a smile and he rewarded her with a grind of his wrist. Right at her sweet spot too!
