Another Reunion

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Anal Fucking

[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. Escort 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!

She choked back a moan, turned it into a cough. “Okay, I’ll go after we finish chatting.” Theo, the fucker, was still gently stroking her, thick fingers slowly working through her juices, stretching her slick walls and twisting around her clit as if he was trying to wind her up. She felt hot and cold, praying that Theo wouldn’t stop but also praying that there wouldn’t be any wet noises. If her mom noticed them, Vanessa would be so dead.

“Just five more minutes alright? Tomorrow’s a new day.” Mom took a sluggish sip of water as she headed back upstairs.

Vanessa finally let out a breath when she heard the door shut upstairs. And then she immediately muffled a shriek. Theo started fingerfucking her for real now, making her body bounce as he sawed three meaty fingers into her pussy, his palm scraping her clit every time.

“So… rough,” she moaned. “Slower… slower!” Ignoring her words, his fingers continued plunging into her, the frantic squelching making her feel so dirty.

The feeling in her stomach built until she was a trembling mess on the couch, mouth gaping, legs splayed, Theo’s fingers still fucking her through her aftershocks.

“Stop, stop!” She felt like her body was flying apart, she wanted to climb off his lap, but Theo sat up and pinned her against his chest with a strong arm around her waist. She gulped for air as her pussy went from hot to burning.

“C’mon,” he coaxed, “I know you can give me another one.”

“I can’t! Stop, Theo, please!” She half-cried and half-whined, writhing against his strong arm. It was too much. Something was happening in her body. It was melting her mind. It felt like all of her was trembling, shaking, stretching, until suddenly she came again, toes twitching and eyes unfocused. It felt like her brain just shut off. He gently pumped her a few more times before sliding out his fingers with a slick pop. Vanessa gasped at how empty her pussy felt now, and Theo took that chance to lick into her mouth, kissing her long and sloppily. She snuck back upstairs while Theo took care of himself in the bathroom.

The next morning when Vanessa came down for breakfast, wearing more decent pajamas this time, it took everything she had to greet everyone without flushing at the sight of Theo.

“Some urgent files came in, I’m thinking I’ll skip the hike so I don’t have to miss the barbeque tonight.” Theo caught her eye for a split second. She hid her face and pretended to concentrate on her cereal.

Her dad shrugged easily. “As long as we can count on your grilling expertise tonight. Vanessa, you want to come hiking with us old folks today?”

“Meeting up with the old gang later, Escort Bayan sorry Dad.”

“Thought so. Why do you even come home anyway?” Her dad joked and they all laughed, Theo loudest of all.

Not ten minutes after the group drove off, Vanessa and Theo were sucking face against the kitchen counter, hands groping wildly under their clothes. It was like being a teenager again, and the thought made Vanessa laugh. Playfully, she pulled at his pants. They fell around his ankles before he kicked them off.

Before she knew it, her back was on the floor with her shirt rucked up high so his lips could suckle at her small boobs while his hands yanked her sweatpants off in one fluid motion. She was practically naked but Theo was still wearing his shirt, and this seemed unfair.

“Take off your shirt, let me see that sexy chest,” Vanessa teased. Theo sat back on his heels to comply and for the first time, Vanessa saw his hard cock jutting out of his dark pubic hair. The two of them had always snuck around before, and she’d rubbed him off or had him grind against her slow and dirty, but she never had the chance to look too closely at what he was packing. It was fat and stout. Thick like his wrists, his legs. Apparently Theo was broad everywhere.

“Like it?” He winked.

“Yeah…” she licked her lips subconsciously, trying to figure out if it she’d ever seen a fatter cock in real life.

“Yeah you’re gonna love it,” Theo smirked. Seemingly from nowhere, he produced a foil packet and a small bottle. “Put this on me,” he said, throwing the condom to her and popping the cap on the lube as he knelt between her legs. She sat up to rolled it onto him, giving him a few mischievous strokes and squeezes before she was distracted by the cold lube being generously massaged into her.

“Aren’t I wet enough?” Her eyes half closed, savoring the sensations.

“You’ll want to be wetter for this,” he shuffled forward to tap his cock at her entrance, sliding through her folds teasingly until his cockhead was nice and wet. His face was flushed and dark with anticipation.

“Uhhh… hm?” Her eyes opened wide as she suddenly caught up with what he was saying. They followed the motion of Theo’s hand as he humped himself once, twice, and then lined himself up.

“What are you doing?” She gasped. This was an exciting game, but she had honestly never thought about going all the way with him.

“No more of your teasing,” Theo growled.

“I don’t know…” Vanessa felt a spike of guilt. They’d never gone further than this. Messing around was one thing, but actually fucking one of her dad’s best friends felt different, weird, too real somehow.

Theo raised an eyebrow and swirled two fingers deep into her pussy before withdrawing them. They came away glistening, covered in lube and her juices, and he brought them to his mouth, appearing to savor the taste while staring her dead in the eye. Her pussy spasmed, feeling lonely.

Vanessa squirmed. Maybe it would be fine…

“Okay,” she said uncertainly.

“You a virgin?” His skeptical face made her blush.

“No! I’ve done it, geez!”

“Yeah?” He caught her mouth in another dirty kiss, tasting her until she melted. “Yeah, I thought so.”

“I’ve fooled around plenty. It’s just…” For some reason she felt herself suddenly defensive. She wasn’t even a virgin, why did she have to feel embarrassed!

Theo seemed to struggle for a minute before he blew out a breath and shot her a comforting smile. “You know, my waist ain’t what it used to be… let’s go do this on your bed, yeah? Maybe it’s being in the kitchen.”

Vanessa blushed. If they fucked in her childhood bed she’d never be able to sleep there again without getting hot and bothered. But then that had never stopped them from messing around in the rest of the house. Wordlessly she let him pick up their clothes and herd her up the stairs, feeling him leer at her ass the whole time.

Scooting back down on her sheets, she wavered again. It was hot having Theo naked in her room, no doubt about it, but did she really want to cross this last line with him?

“Theo, maybe…” Her eyes were big and round as he rearranged her legs until he could settle on his knees comfortably Bayan Escort between them. Calloused hands gripped her thighs and pulled her until her ass was half in his lap. His cock was so hot it burned her when it brushed the inside of her thigh.

“You don’t want this?” He asked doubtfully, running his hand along her flank. It was clear he was running out of patience, his expression a little annoyed.

“I don’t know…” Vanessa bit her lip. Strong hands gripped her waist, testing their hold. “I just never thought of doing this…”

His eyes watched her struggle. “Where did you think this was going to go, sweetheart, besides my cock stirring up your sweet cunt?”

Without waiting for a reply, he pinned her legs wide and a hot fat cock speared into her, parting her inner walls, thick and unyielding and utterly devastating. The fire in her stomach bloomed. Tears formed at the corner of her eyes; she looked like she was having a religious experience.

His thrusts punched out small animalistic sounds on every stroke, small moans and cries that could have been either pain or pleasure. His body folded over her, the wiry hair on his chest scratching at the tender skin of her boobs, her belly. She clawed at his shoulders, trying hard to hold on, but he fucked her until she’d ended up half-braced against the headboard, trying to fuck herself back onto that magnificent cock.

“Look sweetheart, look how much your tight cunt loves it,” Theo panted in her ear. Vanessa stared dumbly at her pussy gobbling him up. He was so thick and she was so small, and the pressure of his shaft against her walls was intense but each inch sunk into her like she was made to hold his cock.

Clutching her to him, he rolled them until she was slumped docilely on top of him, gravity helping impale her even deeper on his dick. The new position made his fat cockhead hit that sweet spot every time. She was drooling now, gasping, arms braced against his chest, sweat-matted head lolling on her limp neck, trying to hold on for dear life. She loved it, she loved feeling so used, she loved his calloused hands groping her ass, pulling and squeezing until her pucker felt the cool air. A sly finger pressed flat against the wrinkled skin as a promise of things to come.

It seemed like she was on the edge for hours, always so close, but she clenched her teeth and tried to hold on. Finally she came with a shout, eyes teary with overwhelming pleasure.

“Gobbling me right up,” he gritted out. Her sweet pussy was milking him greedily now, crying out for him to give her more. “Gonna fill you up and then I’m gonna fill you up again later, fill you up tomorrow, gonna fuck you until you only know how to take my fat cock and cry.”

Theo shifted so he could sit up and wrap his arms around her limp body, tight so she couldn’t dismount, keeping her bouncing bonelessly on his cock as she moaned shamelessly. His tongue thrust into her ear with each stroke. “Slut,” he chuckled when she gasped, “your sweet cunt is even better than Sheila’s.”

He made her come again, sobbing, before he finally shot his hot load, giving her body what it desperately wanted.

“Next time we’ll try for three,” he promised as they lay on her ruined bed, catching their breath. Vanessa vaguely wondered if he’d ruined her for anyone else… no wonder there was always a line of people waiting to date him. Suddenly she was jealous of Sheila.

Though Theo knew he couldn’t get hard again for a while, he made her try, kneeling between his legs and lathering his soft cock. The view wasn’t too bad, her ass up with drool soaking her chin, almost cross-eyed with greed.

True to his word, he fucked her again that afternoon, expertly playing her body until she squirted. She didn’t even know she could squirt. Maybe he really did ruin her, because now she couldn’t imagine waiting another year to worship that cock again.

They had to stop and prepare for the barbeque when the rest of the house returned. Vanessa had to fake a story about a fall when her mom noticed her walking strangely. In the last days of the reunion, they were back to stealing moments to avoid suspicion, though Vanessa couldn’t help but feel disappointed.

A few weeks later, her mom called, gossiping that Theo had broken up with Sheila and gotten ribbed by the entire group, but didn’t say a word about whether he was dating anyone now. Vanessa let out a relieved breath and went back to the bedroom where he was waiting for her.

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