Pink Chair Diaries: I Dare You

I Dare You

(c) 2007 by Maura Anderson

Terry groaned and collapsed back onto the luxurious bed, kicking off her strappy sandals. Free at last, free at last. She chuckled tiredly at her own attempt at humor. Now a single woman again, she was determined to make the most of it and the two week vacation with her life-long best friend, Jason.

Well, almost life-long anyway. They’d met in kindergarten and cemented their friendship when he’d dared her to jump off the moving playground swing. Her broken arm was proof of her inability to turn down a dare from Jason.

Her husband, make that ex-husband, never understood their closeness. From the first time the two men had met, the animosity had been tangible. Jason disapproved silently but her ex-husband complained at any opportunity. It didn’t matter how many times she tried to reassure him, he was convinced Jason was a threat to him.

Eventually, his inability to relax and stop trying to control Terry spelled the death of their short marriage. Hell, he wasn’t even good in bed, he was so uptight.

Terry closed her eyes for a moment, picturing Jason’s muscular body and wishing he had any interest in her as more than just a friend. She didn’t want to destroy their friendship by coming on to him but some days it was really difficult to bite her tongue … and to not bite his firm ass. But without some sign he was on the same page, it would be too much to risk.

To distract herself from images of Jason, she got up and went to investigate the large basket on the room’s desk. Already in the room when she checked in, she’d assumed it was a gift from the resort management. Instead the tag was in Jason’s heavily slanted scrawl. Happy Divorce.

She chuckled to herself as she began to untie the ribbon and peel back the cellophane from the basket. Who knows what the perennially unattached bachelor would decide she needed. “Oh man, what have you done, Jason?”

There was no telling what he’d decided she needed to have right now. Terry could only hope he’d not decided on something either alive or perishable.

With some trepidation, she got the wrapping off the basket and began to unpack its contents.

A box of Godiva chocolates.

A bottle of wine.

A box of scented candles with a lighter taped to it.

A bottle of vanilla-scented massage oil.

A slender vibrator.

A bottle of lube.

Terry paused and shook her head at the last two items. Jason obviously decided that she needed some physical fun. Or he was hoping to embarrass her so he’d have the upper hand when he arrived.

Reaching back into the basket, Terry’s fingers closed over the flat square package tucked in the bottom of the basket and pulled it out.

“What the hell?”

The clear plastic package had a pink object inside and when she flipped it over, she saw an illustration of a pink blow-up chair. Candy pink, Barbie pink. But the dildo mounted in the middle of it didn’t fit at all with the color.

Terry’s mouth dropped open. This had to be a joke. Jason must be looking forward to giving her hell about this chair being better than her ex. She had no idea anything like this even existed.

Fascinated despite herself, she began to read the information on the label of the chair’s package and saw a note in thick black marker. I dare you.

*****

It took Terry a shower and nearly half the bottle of wine to get up the courage to unpack and blow up the chair. She’d be damned if she declined Jason’s dare. The pink chair certainly sparked her imagination. She ran a finger lazily up and down the pearlescent pink dildo that adorned the seat of the chair.

Too bad it wasn’t Jason’s cock instead of a plastic substitute.

She drank another sip of the wine. She had time. Jason wasn’t due to arrive until tomorrow morning. Maybe she could fulfill the dare and gain some measure of control over her libido before he joined her. It had to be preferable to tackling him the moment he arrived and telling him to fuck her.

Terry’s fingers grasped the base of the dildo and stroked to the tip, imagining it to be Jason’s thick, hot cock. Up and down, fingers tracing over the tip with every stroke. Would it drive him crazy? Would he groan out his desire?

She untied the belt of her robe with her other hand and spread the sides open so she could run her fingers over her own body. She cupped her breast and tugged on the silver ring through her taut, dark pink nipple. The sharp ache made her pussy clench in response.

Gently, then sharper, stronger, she alternated pinching her nipple and flicking at the ring. Each burst of sensation made her wetter and more aroused, her hips flexing and rocking in arousal.

Releasing the chair’s dildo, Terry spread her legs as much as she could from where she knelt on the floor and ran her other hand between her legs. She teased herself briefly, running her fingers lightly over her bare labia, barely touching her sensitive lips. What would it feel like to have Jason’s fingers there? His lips? His tongue?

A shudder rolled through her and she gave her other nipple ring a sharp tug.

What would his reaction be to her piercings? He’d dared her to have her belly button pierced two years ago and she’d done it, but he didn’t know about the other three piercings. In a fit of rebellion, she’d had them done the day her divorce paperwork was filed with the courts. Unfortunately, they seemed doomed to remain a private indulgence.

Terry took another long sip of the wine, draining the tumbler she’d poured herself. She didn’t have a huge tolerance for alcohol and didn’t want a hangover, just enough of a buzz to take on the dare

The very nice red wine did nothing to soothe her thirst, instead the slightly spicy flavor made her wonder just what Jason’s skin would taste like.

Draining the rest of the glass, she popped a dark chocolate into her mouth. She savored it, held it in her mouth and let it melt onto her tongue. The rich dark flavor complimented the wine perfectly and made her close her eyes for a moment and moan softly. Would Jason’s cock be as rich and sweet as the candy? As dusky and mysterious?

Without conscious thought, one hand strayed again to her breast and resumed rolling and tugging her nipple and its sensitive piercing. She ran her other hand back down her belly and between her thighs to tap a finger delicately against the ring just peeking out from between her waxed labia. Her pussy grew hot and creamy as she repeatedly fondled and tugged on her clitoral hood ring. Delicious jolts of sensation made her spread her legs further apart to savor the feeling.

Terry’s tongue captured a tiny bit of escaping chocolate off her lip and she decided to tackle Jason’s latest dare. Unlike some others this would be one she would enjoy, even if it was Jason’s body she wanted, not a pink plastic substitute.

She was wet enough not to need it, but poured some of the lube into her hand and stroked it over the chair’s dildo. As if it were a real cock, Jason’s cock, she slowly stroked her hand from the tip to the base. Up and down, her grip growing firmer, she massaged the slippery lubricant into the cock. Terry imagined her friend’s voice urging her on, telling her he wanted to be inside her body, wanted to fuck her.

A few pushes so the pink chair was sitting beside the bed and Terry scrambled to her feet. Poised with her hands on the bed to keep her balance, she threw her curly brown hair back over her shoulder and lowered herself until the tip of the dildo just entered her pussy, teasing herself, anticipating the fullness to come.

Guiding the pink cock with one hand, she spread her legs and slowly, oh so slowly, impaled herself. She traced the tips of her fingers along the skin stretched around the dildo, then in circles around her clit, each bump against her ring making her pussy clench with the electric flash of pleasure.

She closed her eyes and focused on her fantasy.

She could almost feel Jason’s hands on her pussy, playing with the ring and teasing her by holding back. His sexy playful chuckle as he made her wait, made her beg. “Jase. Please, Jase. Fuck me.”

He refused to hurry, moving in and out of her with excruciatingly slowness. She pictured his square jaw clenched with the effort to control their pace. His denim blue eyes unfocused and half-closed in pleasure, his sandy blonde hair disarrayed by her fingers.

“Please, Jase. Faster, dammit, faster!”

Rising and falling on the pink chair, Terry writhed with the need to come. Just a little more. “Jason, I’m so close.”

“I see you like the chair, Terry.”

Her eyes snapped open at the sultry baritone voice she knew she wasn’t imagining. Jason was walking toward her from the door between their adjoining rooms, discarding pieces of clothing along the way.

Blue eyes blazing with a heat she’d never seen him direct toward her, he peeled off his boxer-briefs as he got within arm’s reach, revealing a deliciously erect cock jutting from a nest of neatly trimmed curls.

Her mouth watered at the sight of Jason’s body. Skinny dipping as a teen was the last time she’d seen him nude and he’d matured in ways she’d not anticipated.

Her pussy clenched around the dildo impaling her as he wrapped his long-fingered hand around his own cock, stroking it from tip to base, then back to the tip again.

“I heard you, Ter. I heard you begging me to fuck you. Do you have any idea how many years I’ve longed to hear those words from you? How many years I’ve had to stand by as ‘just a friend’ while you were sleeping with men that didn’t deserve you?”

He stalked a step closer and grabbed her face with both hands, gently forcing her to look up at his face instead of at his cock. “If you don’t want me, Ter, tell me now.”

A deep breath and Terry nearly drooled at the musty, earthy scent of Jason’s body. “Fuck me, Jason. I want you to fuck me.”

His sensual lips pursed as he looked into her eyes. “I won’t fuck you, but I will make love to you, Terry.”

Rational thought fled when he captured her lips with his own. Gently teasing and nibbling, he coaxed her to open to him, to allow his tongue to explore her mouth and tenderly stroke her. He slowly intensified the kiss until they both gasped.

Jason dropped to his knees in front of her, parted her knees and ran his hands up and down her thighs. “Sexy nipple rings, Ter. Dainty body piercings on a woman turn me on.”

The last words were muffled as he captured a ring between his teeth and tugged gently on it before releasing it to suck her hard nipple into his mouth.

The feel of his hot tongue and lips on her breast made Terry writhe. His talented tongue flicked and teased the nipple and ring while his hands continued to stroke up and down her thighs, coming close to her pussy on every stroke but never actually touching her.

“Jason, please.”

Releasing the nipple with a pop, he licked his way across her chest to her neglected breast and gave that nipple equal attention with tender bites and licks, seemingly oblivious to her hands clenched in his hair.

Unable to stay still any longer, her hips moved in small circles, the dildo still inside her suddenly a poor substitute for Jason’s hot, hard cock. “Please, Jase. I need you inside me.”

He captured her hips and held them still. “A hood piercing? Oh man, that is so sexy. I didn’t think you had it in you.”

Before she could respond he’d buried his face between her legs and was exploring her bare slit with his tongue and teeth. Nibbling and stroking, he tugged on the small silver ring and then slid his tongue down to where the pink chair’s dildo still impaled her. His hot, wet caresses drove her right to the brink of orgasm, her body clenching in anticipation.

He pulled away suddenly. “Oh no you don’t.”

She whimpered and released the death grip she still had on his hair, letting him lift her off the blow up chair and arrange her on her knees using the pink chair to support her head and shoulders. She rocked back and forth on her knees, her pussy weeping with need for him. The smell of her own cream filled her nostrils, the scent of sex only driving her lust higher.

The distinct sound of a condom wrapper behind her made her realize this was really happening, she was really going to have the man she’d wanted for as long as she could remember inside her.

Strong hands grasped her hips and Jason nudged her knees further apart. “Lick it, Terry. Taste how delicious you are. I want you to imagine you’re sucking my cock, tasting your flavor on me.”

Groaning, she moved her head toward the center of the chair and captured the base of the dildo with one hand. She made sure Jason could see what she was doing, her hair pushed away from her face before she trailed her tongue in a long, slow line from the base of the chair’s dildo to the tip. Her own juices made the taste raw and somehow risky, a bit dangerous.

As she opened her mouth to take in the tip of the pink cock, Jason eased his hot, hard cock into her pussy. Slowly and steadily, he fit himself into her until he was buried to the root, stretching her more than she’d imagined.

Groaning her name, he stayed there, not moving.

She rocked her hips, then licked up and down the dildo again, trying to inspire Jason to action. She needed him to move. Needed him to pound into her – to need her the same way she needed him.

Moving his hips in small circles, he seemed unwilling to move more than that.

Finally, Terry let go of the chair’s cock and shoved back at him. “Move, Jason. I need your cock, so move.”

Her growled order seemed to set something free in him, something primal and raw. He grabbed her hips and began to glide in and out of her. Each thrust stroked over her g-spot, driving her closer and closer to an orgasm almost frightening in its intensity.

Her pussy clenched around his cock, relishing the feel of his hot, hard length.

“I love you, Terry.”

She knew she should be surprised by his announcement but she was far too close to coming to worry about it, to do more than react with the truth she’d not really acknowledged to herself. “I love you too, Jason.”

As if the words tore away the last of his inhibitions, Jason pounded into her, reaching his hand around her body to rub her clit in time with his strokes. “Come for me, Ter. I can’t hold out much longer.”

The orgasm she’d been on the edge of burst over her like a tsunami, her body convulsing in waves of pleasure.

Jason thrust into her and cried out her name as he came, his cock pulsing hotly within her. He hugged her close to him and collapsed onto his side on the floor, still buried deep inside her.

Their breathing slowed gradually and Terry tried to not think too much, not wanting to spoil the spell.

“Terry, I love you and have for years. Will you marry me?”

Somehow Jason’s proposal fit their entire relationship, spontaneous, irreverent and full of love. Just as she took a breath to tell him yes, he made sure she’d agree.

“I dare you.” He whispered.