Asher At Bottom

Tabitha and Asher are back! Tonight they're trying something new and Asher is all in! This story features anal play and very light BDSM themes. If that's not your cup of tea you might want to skip this one. All characters are mine and everyone is over the age of 18.

Asher gasped in a harsh breath, nearly choking on the spicy tuna roll he'd just put in his mouth. He bit down a moan as he stared across the table at Tabitha.

One hand was shoved in the pocket of her loose-fitting pants, while the other cradled her chin, seemingly entranced by what Victor was talking about. Asher swallowed the food in his mouth roughly and adjusted in his chair. He was grateful for the noise level of the sushi restaurant, so Samantha who was seated next to him couldn't hear the vibration of the plug shoved in his ass.

"That's a great idea Victor! Maybe Asher would be interested joining," Tabitha said loudly.

Asher drove a hand over his forehead, swiping away the sweat that had popped out along his hairline.

"Sorry, what was that?" Asher sputtered out.

Tabitha caught his eye and grinned at him. Asher twitched as she bumped up the vibration again.

"D&D. You ever play before?" Victor repeated his question.

"Oh! Um, ye-yeah, a little in ha-high school," Asher said, trying desperately to talk normally, fighting off the groans that threatened to spill out.

"Nice," Victor paused studying Asher's face. "You OK, man? You look a little...flushed."

Asher swore he saw a knowing smirk cross Victor's face for just a split second before it vanished into innocence.

"Ha! Yeah, I'm ffu-fine. Spicy tuna huh?"

Asher stared back down at his plate for a second, then turned pleading eyes to Tabitha. She covered her mouth with her fingers and grinned at him again, but the vibration eased back down to a low hum.

He blew out a quick breath. He had already been nervous about meeting Tabitha's closest friends, but then she had suggested the butt plug thing. He couldn't resist her when she called him a pretty boy. Besides, it sounded like so much fun! He hadn't taken into consideration the challenge of keeping his cool all night, or how often Tabitha might turn on or bump up the vibration.

His cock was hard in his pants straining against the lacy thong Tabitha had him slip on. The lace rubbed at his moist, swollen head, making him wish he could stand up and go rub one out in the bathroom quickly, but there was no way he could stand up with the erection he was currently sporting. Not to mention the fact that Tabitha had not granted him permission to cum. Asher scooched his chair closer to the table attempting to hide the bulge in his pants.

"So, you'd be interested in joining our campaign?" Denise asked from her place next to Tabitha.

"Oh, uh, sure. It's been a while since I played though, I might need a little help," Asher said with a small smile.

"Oh, we could probably make that happen," Denise said returning his smile.

"Well, great! We're playing next week if you're free, Thursday night," Samantha said. "You could step in as a guest character, see if you like it before committing!"

Victor nodded in agreement, cradling his chin while he smiled a Cheshire cat grin at Asher.

"OK, sounds fun," Asher said.

The rest of the night progressed with Tabitha mostly laying off the remote in her pocket. She only bumped it up once more and that had been a more gradual increase. However, by the end of dinner Asher felt like his eyes were going to roll back in his head from the rise and fall of his arousal. She had stopped it completely about twenty minutes before everyone had finished up, so Asher could stand up without embarrassing himself.

They walked back to her car, Tabitha's arm around Asher's waist, her opposite hand shoved in her pocket. The lacy thong rubbed over Asher's taint bringing a flush of warmth to his loins again. He leaned his head on Tabitha's shoulder and sighed quietly.

"How are you doing pretty boy?" she asked, clicking the vibration back on.

Asher moaned, pressing himself into Tabitha's side.

"Mmmm, good," Asher groaned out.

Tabitha smiled, glancing down at the growing bulge at the front of Asher's pants.

"You still want to play the game we discussed when we get back to mine?" she asked quietly.

"Yes," Asher hissed out. Tabitha clicked the remote again and Asher tensed against her. "Oh fuuuck, Tabitha," he groaned.

Tabitha's cheeks flushed and she bit her lip. A wave of warmth coiled into her belly.

"You like that pretty boy?" she grumbled, pressing a kiss to his temple.

"More than I thought I would," he sighed out.

"Here we are, get in the car," Tabitha said.

Asher climbed into the passenger seat of Tabitha's car. He pulled the seat belt across his lap deliberately dragging it over the tip of his cock. He sucked a breath in through his clenched teeth, pressing his ass hard into the leather seat, wishing Tabitha would bump up the vibration intensity.

She came around the back of the car and clicked the remote up one level. A grunt sounded as she opened the driver's side door.

"Ughn, yeah," Asher moaned.

He rubbed his hands roughly up and down his thighs.

"Careful, pretty boy," she purred. "No touching."

"Hhhahh, I know," Asher groaned.

His pants strained against his growing erection. Spreading his legs open a bit more, he gripped and massaged his thighs. A dark spot appeared at the top of the generous bulge.

"Oohh my, pretty boy. You're enjoying this quite a lot," Tabitha said, feeling the drip of moisture in her own panties.

Asher grunted loudly again.

"Hhoohh god, yeah," Asher sputtered out.

His fingers kneaded wildly at his thighs, rubbing up and down, but never touching his throbbing cock. His head fell back against the head rest, eyes squeezed shut, mouth hanging open, panting slightly. His hips rocked in the seat rhythmically, moving the lace over his sensitive spots, deliciously shifting the plug.

"Asher, are you going to cum?" Tabitha asked.

Asher opened his eyes and held Tabitha's gaze with a pleading look.

"Please can I cum Tabitha?" Asher asked in a small voice. "Please?"

She bit her lip, pinching a nipple over her shirt between two fingers. Leaning forward she put her mouth to Asher's, tongue dancing forward tasting of Sake. She grinned as he desperately kissed her back.

"You can cum if you keep it quiet," she whispered.

"That's hha-hard," Asher moaned out.

Tabitha knew this of course. They had been playing together for months, and Asher was always very vocal, which was a huge turn on for Tabitha. But she wanted to challenge him tonight. Give him a difficult command and see if he could follow the rules. He was such a good boy, always following her rules.

"I know it is pretty boy," Tabitha said, dragging an almond shaped nail down his cheek. Asher groaned as another dark wet spot joined the first. "Show me you can follow the rules. Aren't you my good boy?"

Tabitha dragged a hand through Asher's hair and down his neck. She licked at his earlobe, sucking it between her teeth for a second, biting lightly.

"Hhhaaa," Asher moaned loudly. "F-fuck, OK. I'll, ugh, I'll be quiet."

At that he clamped his lips closed, breathing deeply through his nose.

"Alright," Tabitha smiled.

She clicked up the intensity with her remote. Asher's mouth dropped open, but no sound came out. He slowly closed it again biting hard on his lower lip. The vibration rumbled through his ass and straight to his cock. His hips rolled, shifting the plug in his ass, rubbing his tightening balls against the rough lace of the thong he wore.

His breath tore through his mouth and nose, but he made no sounds, just a quiet panting. His hands rubbed wildly on his thighs, grabbing and squeezing the fabric tightly. His brow scrunched up and another dark spot appeared where his cock strained. Tabitha leaned forward and whispered breathily into his ear.

"You can touch yourself pretty boy," she said, increasing the intensity to its highest setting.

Asher's hands immediately kneaded over his balls roughly and gripped his cock squeezing slightly. He panted out a breath as his mouth fell open soundlessly again, eyes scrunched closed, and his hips rolled upwards as he came, cock spurting slightly through the fabric of his already moistened pants. He panted quickly, looking down at his lap now as his hips rolled with the pulses of his cock. Tabitha hummed from her seat and Asher looked over his orgasm began to ebb away.

"Good job," she said, voice deep and husky. "I cannot wait to get you home."

Her eyes darkened as she shut off the plug and started the car. Asher caught his breath and smiled, his eyes sliding closed as Tabitha drove back to her house. As she merged onto the highway, Asher fell into a light sleep, his head resting against the cool window, with a small smile on his lips.

~~

Tabitha pulled the fabric of the thong he wore to the side and eased the plug from Asher's ass gently. The fabric snapped back over his sensitive hole, and he twitched. Tabitha told him to get on his knees while he waited, still wearing the lacy thong, coldly moist from his exploits in the car.

He could hear her behind him. Just the thought of her nude and the game they were about to play made his cock begin to swell. Admittedly, he was nervous about this one. Although he was slightly reassured since wearing the butt plug all through dinner had gone so well for him. Wearing it in front of her friends, after meeting them only very briefly before this dinner had been intimidating, but he thought he did alright.

"Are you ready Ash?" Tabitha asked.

He heard the clink of buckles.

"Yes," Asher said.

He shifted on his knees a little.

"Turn around," she demanded.

He leaned forward on all fours and turned around the face her going back on his heels once he'd turned.

"Remember the rules?" she asked. Asher nodded. "Tell me."

"Two taps for stop. Turnip's the safe word," Asher recited.

"Good boy," she purred.

Her fingertips ran through his dark brown hair gently, lightly scratching at his scalp. He leaned into the touch, his eyes sliding closed as goosebumps erupted down his neck, cock beginning to strain against his thong. She picked up Asher's choke chain and held it up in front of him.

"What do you think good boy?" Tabitha asked. Asher thought for a minute, eventually shaking his head. "Hmm, no? Are you sure?"

Tabitha set the choke chain aside carefully, almost reverently. Asher had used the choke chain at least once each time they had been together. He had even gone as far as wearing it out to get a meal after they had finished one night. He adored the weight of it around his neck, like a reminder of what a good, pretty boy he was. But tonight, he was doing something he had never even thought of doing. The whole thing was Tabitha's idea. He had been surprised by how aroused he became when she had first proposed the game.

"I want to feel everything the first time," Asher said.

Tabitha smiled down at Asher's upturned face, tracing her fingers along his jaw. His eyes blazed with excitement, overriding any nervousness he felt, his cheeks flushed.

"Oh Ash. You truly are such a good boy," Tabitha growled. "So, pretty boy, you know what we do first."

Asher grinned and nodded.

"Yes, Tabitha," he murmured.

A wave of arousal crashed through her and nestled between her legs. She ticked her legs open a little as Ash rose up on his knees. He brought his fingers to her rapidly moistening slit. His fingers ran between her labia quickly, swiping up and circling around her clit. She sighed slowly; one arm dangled loose while the other hand slowly stroked through Asher's hair. He leaned his head on her stomach as his fingers rubbed over her slit, circling her clit repeatedly.

"Mmmm, yes," Tabitha purred.

Asher's cock grew in the lacy thong he wore, dripping copiously through the delicate fabric.

"Put your fingers in your mouth pretty boy," Tabitha demanded.

Asher took his fingers from her pussy and pushed them into his mouth. He tipped his head up, looking up at Tabitha through the lashes of his half-closed eyes as he sucked her arousal off his fingers, soaking them with his spit.

She clenched her teeth and sucked in a long breath. Her fingers gripped into his hair, and she pulled it with a sharp tug. Asher's eyes closed for a second and his mouth dropped open with a little whimper. Tabitha groaned, the moisture between her legs dripping freely.

"Jesus, Ash," she moaned as he whined at the sting of her hair pulling.

She pulled his head back to lean on her stomach, loosening her grip and scratching her nails gently over his scalp again. He moaned again and nestled against the soft squish of her belly.

"Keep going pretty boy," Tabitha groaned.

She grabbed his wrist and brought his warm, wet fingers back to her pussy. He slid his spit slicked fingers over her slit again, circled her clit, then pushed them back through her dripping arousal. Two fingers slid easily into her entrance as Ash's thumb pressed on her clit.

"Hhhughn, yeah," Tabitha moaned. Her hips began to roll over his hand. "Harder pretty boy. Make me cum."

Ash pulled his fingers out and pushed three in roughly, rubbing savagely at her clit. He wrapped his free arm around her hips, clinging to her as his fingers drove into her. Her hips began to roll harder and faster. Her breath came in quick pants. She clutched at Asher's wrist as his fingers pumped in and out of her, his thumb still moving over her twitching clit.

Tabitha's back arched and her head fell back, curls bouncing as she moaned opened mouthed. The shaking of her thighs preceded the rough squeeze of her soft silky walls around his fingers, and a rush of hot arousal came flowing from her, seeping down his wrist. Her nails dug into his wrist as her rolling hips began to slow, her orgasm ebbing away slowly in little jerks.

"Oh, god, that was good. What a good boy."

She leaned down, tipping his chin up so their lips could meet. Her tongue danced forward, both hands cupping his face as she kissed him.

"Are you ready for your turn pretty boy?" she asked.

Ash didn't even have to think about it.

"Yes, please Tabitha," he said.

She smiled and nodded.

"Give me one minute sweetheart," she murmured.

She kissed his forehead then turned to her bed. He watched her slip into the harness, pulling the straps and buckles snugly around her body. She turned and Asher swallowed hard.

The dildo wasn't huge, it was his first time after all, and Tabitha wasn't looking to wreck her favorite toy. She had assured him that it would be a perfectly average and reasonable five inches.

Asher stared up at Tabitha's face then down at the dildo.

"There's...there's balls on it," he said, feeling like an idiot for pointing out the obvious.

"Yes..." Tabitha said slowly. "Is that OK?"

Asher nodded once quickly. His eyes flicked between the two for a minute while she stood making some last adjustments. He felt a wave of anxiety and excitement rising in him. His cock dripped with the anticipation, remembering the butt plug vibrating away inside him.

"Asher," Tabitha said seriously, the playful dom gone for a moment. His eyes flicked back up to her. "Do you still want to?"

Asher nodded.

"You look flushed," Tabitha said. "Are you OK?"

"I'm nervous," Asher said.

She nodded knowingly. That was what he appreciated most about this woman. She never shamed him, never laughed at him, had always validated his feelings, creating a space where he didn't feel embarrassed admitting how he was really feeling.

"That's OK," she said. "We can stop, if you want. Try it another time."

"No!" Asher said quickly.

His asshole was already aching from the butt plug, and despite his nervousness he still wanted this, hadn't realized how much he'd wanted to try it.

"Alright gorgeous," she smiled wickedly. Asher allowed himself to relax a little, seeing her slip back into her role. "Get on the bed pretty boy, all fours."

He climbed onto the bed and positioned himself as he was told. Tabitha's hand traveled down his spine and over his exposed ass cheeks.

"Down in front sweetheart," Tabitha grumbled.

She smacked one ass cheek hard. Ash grunted with the sting and let out a ragged breath. She rubbed her hand over the stinging mark for a moment before smacking the other cheek, leaving matching hand shaped marks. Asher pressed his chest to the bed, his head turned and pressed into a soft pillow.

"That's better, good boy," she said and ran her hands over the stinging slaps.

He sucked in a quick breath.

"Uughn, Tabitha," he groaned.

She growled quietly as she leaned forward to grip his stiff cock in her hand. Her fingers slid under the lace and traced over his generously dripping tip. She squeezed, stroking up and down Asher's cock gathering as much of his dripping precum as she could.

Carefully, she brought her hand back to his crack, running her fingers under the lacy fabric, pulling it to the side. Then she ran her slick fingers through it. He shuddered and grunted. She pulled his cheeks apart and rubbed a finger around his puckered hole, smearing his precum in little circles.

"Oh! Hhhhaa yeah, oh Jesus," Asher groaned.

Tabitha pulled both cheeks apart again and brought her mouth to his hole. She licked up with the flat of her tongue tasting his precum, his musky scent filling her nostrils. Saliva rolled off her tongue and over his tight hole. She circled around it slowly with her tongue. Rubbing at his taint with her free hand, cupping his balls and massaging them gently occasionally.

She could feel his asshole twitching under her tongue as she pressed it forward, in circles, up his crack. Finally, she pulled back and took the lube from her bedside table and squirted a generous amount into her hand. She let some drip into Ash's crack, rubbing it over his already slick hole and used the rest on the dildo, coating it generously.

"Give me your hand pretty boy," Tabitha said.

Asher pushed himself up a bit and put one hand behind him. She coated two of his fingers in lube.

"My nails are too long," she muttered as she used Ash's fingers to press into his asshole.

"Hhhhhohhhh," Asher moaned as Tabitha pressed his middle finger into his asshole.

"How does that feel sweetheart," Tabitha asked huskily. Asher moaned and pumped the finger in and out in reply. "Hmmm, I think he likes it."

Asher continued to finger himself for a minute while Tabitha watched, grabbing a remote and clicking a button. The vibrator she'd attached to her harness started with a low slow buzz. Her pussy exploded with warmth and moisture at the sight of Asher fingering himself and the rumble of the toy.

"Try two fingers, gorgeous."

Tabitha took hold of his wrist and pressed two of his fingers to his asshole.

"Oh, my god, yes," Asher groaned as he pushed them deeply into himself.

"Fuck, Ash..." Tabitha groaned.

She pulled his fingers from him and pushed him back down to the bed. The tip of the dildo pressed against his asshole, and she pushed forward slowly. Asher panted and groaned at the press of the firm toy in his ass.

"You alright pretty boy?" Tabitha asked as she pressed forward.

"Ughnn, yeah. Please. Please, keep going," Asher begged.

Tabitha stroked her hands down his spine again and pressed farther in until her hips met his ass cheeks, the balls of the dildo rubbed against Asher's.

"You like that gorgeous?" she asked with a slight pant.

"Hhhaa yeah," Asher groaned, pushing backwards a bit. "Ugh, please fuck me, Tabitha."

She gripped the strap of the lacy thong twisting it around her hand and tugged it hard. The delicate fabric ripped, scraping over Ash's stiff cock for a second. He yelped at the sensation and Tabitha panted. She clicked up the intensity of her vibrator and began to slowly and carefully pump into Asher. Her teeth clenched tightly together.