tagGroup SexNo Longer A DP Virgin...

No Longer A DP Virgin...

byCyleste©

Walking with her head high, Yurman sunglasses on, four-inch heels tapping along with each step, and looking every bit the New York woman, Clarette swiped her Metrocard and nudged the turnstile with her hip to push her way through. Heads turned, both male and female, as she stalked along to the C train platform.

One man in particular stood out of the crowd that was looking her way. He wasn't very tall - maybe 5'7, but held himself so confidently that she found herself looking longer in his direction than any other. He was dressed business casual in black slacks and a white button-up underneath a charcoal gray v-neck sweater. Thick, dark hair crowned his head, and his hazel eyes smiled as she came to stand not even a foot away from him and he looked somehow...familiar. Normally, she would push her glasses up to rest atop her head and smile over at him, but couldn't find it in herself to do so.

Today had dealt one blow after another and it was taking every ounce of strength and pride to not sulk onto the train and cry. The advertising office in her company had been late in handing over a design - which meant she was late handing it in for approval to her clients, and she had nearly lost her job along with the account. To make matters worse, her boyfriend had called and cancelled their dinner plans for that evening and all weekend plans without any explanation, leaving her stranded at their apartment alone.

The train pulled up and the rush to be one of the lucky few to spot a seat was on.

Spotting a seat, Clarette pushed her way through the crowd, only to watch a teenage girl slide in. The girl rose her brow mockingly as Clarette turned away, not willing to give her the satisfaction of a glare. As she turned, she caught his eye. The man in the sweater from the platform had gotten onto the same car with her. "Clarette." She turned, surprised and furrowing. He gave a small smile and begin to rise from his seat, a silent offering to her, but she couldn't handle his kindness or pity and just averted her eyes from his. How did he know her? She watched through her peripheral vision as he slowly sank down, a look of near disbelief on his face. Standing there holding onto the middle rail, she became angrier and angrier thinking over the course of her day as people crowded around her, and when her stop came, she didn't think twice when the man from her original station followed after her.

Coming up behind her, he curled his arm into the crook of hers and leaned in, "Clarette...it's me...Timothy." Furious, she pulled her arm angrily out of his and turned to tell him off when she caught his eye. "You don't remember me, do you?" He didn't wait for a response. "Grad school. '09. Timothy Sansone. I was in the room across from you." This was Timmy? She almost laughed. The awkward boy she had known in school had somehow been replaced with this gorgeous man. The tears that had threatened were gone and her indifference and tough bravado fell. "Tim!" She flung her arms around his neck and pulled back to smile up at him. "Listen," he started with a cute near-blush. "I know it's last minute and I'll understand if you're busy...but...would you care to join me for dinner?" Clarette thought of her evening plans - an empty apartment, TV dinner or Chinese take-out, and a romantic drama that would likely have her crying half-way through. She smiled. "I would love to." Slipping her arm through his, her heart gave a little skip as he patted her hand and winked. "I'll make it any evening to remember."

As she let herself be led through the streets of Manhattan, she and Tim caught up where life had taken them in the past two years. Hailing a cab as he explained how he started his own advertising business, Clarette found herself entranced by the man at her side. She slid into the cab after him and sat silently as he rattled off an address to the cabbie before leaning back and placing a possessive hand on her upper thigh. Gasping as if burned at the sensation of his palm lightly stroking her, Clarette looked up at him and couldn't find it in herself to turn away from his gaze. Unable to stop the movement, she leaned forward slightly, her breath catching as she watched him do the same. They stayed hovered in that position for several long seconds, lips a whisper away - but not touching, before he closed the gap, kissing her with a ferocious passion she would have never expecting from simply looking at him. Losing herself to the moment, she licked his lips lightly and nearly giggled at his reaction as he reached to grip the back of her head, pulling her closer as he kissed her deeper. The driver cleared his throat and Clarette ducked her head to her chest, blushing. What the hell was that? She had a boyfriend, for Christ's sake!

Shaking her head and attempting to shake the thought of the perfect pressure of his kiss away, she watched as he tossed a twenty through the dividing window of the cab and slid to leave the car after Tim nudged her with his hip. Looking around upon exiting, she was shocked to find herself standing in front of the Waldorf Hotel. Smiling as he gave a slight tug to her arm, Tim led her inside, nodded to the doorman, and walked directly to the elevators. She looked over at him questioningly while waiting for the elavator to drop, but all he offered was that sexy smile. Stepping into the box with him, she watched as he pressed for the top floor and smiled at the older woman riding along with them, asking what floor she needed before hitting the button for her as well. The doors opened at the eighth floor, the woman stepped out, and Clarette was left to wonder just what Tim had in mind for dinner.

The top floor came quickly and Clarette felt a moment of panic as he led her to a suite at the end of the hall. He noticed her hesitation and put his hand on the small of her back, propelling her forward. Once inside, he quietly shut the door before turning and stalking towards her. Unconsciously stepping backwards, she bumped against the wall and felt her heart skip as he gripped her wrists and raised them until they rapped the wall above her head. Nuzzling her neck, he whispered her name, "I've wanted to do this for so long..." She gave a half-hearted attempt to freeing her wrists from his grip before saying through shallow breaths, "What...what have you wanted?" Groaning, he grabbed her right wrist and lowered it slowly to his face, sucking a finger into his mouth before passing it across his chest, and lower still to his jean-clad cock. "Clarette..." Pulling her left wrist free, she leaned in to kiss him and whispered a soft "Shhhhhhhhh..."

Tugging his sweater up and over his head, she leaned forward and kissed him with the opening of every button. Pushing the fabric over his broad shoulders, she bit her lip as she gave him an obvious once-over before sinking to her knees, dragging her nails over his bare chest as she did. Looking up at him and licking her lips, she undid his fly and slowly lowered his zipper, exposing a long, thick cock. Pushing his pants down around his ankles, she leaned forward and stroked the full length of his cock across her cheek, turning her head as it passed by her mouth to lick. Holding him lightly, she grinned mischievously up at him as she flattened her tongue and licked from the bottom of his cock to the slit at the top...over and over, she repeated the motion until she felt him shudder. In one swift motion, she pulled him fully into her mouth, feeling him bottom out at the back of her throat. Losing herself in the moment, she savored feeling him grow thicker and heavier as she sucked, and didn't think twice when she felt him lace his hand through her hair and pull her away from him so he could kick his pants off completely.

With a swoop, he swung her up into his arms and grinned at her giggle as he unceremoniously dropped her on the bed. Turning away from her, he opened a drawer near the bedside and removed several items before turning back, blindfold in hand. Her giggle faltered, but he gave a slight shake of his head, understanding her fears as he softly offered a gentle, "Trust me." Not wanting the fun to end, she smirked and tipped her forward, allowing him to slip the snug blindfold over her head. The instant her eyes were covered, he gripped her around the waist and tossed her higher up on the bed, eliciting a yelp and giggle an instant before she felt the first handcuff link her wrist to the bedframe. "Hey...hey!" Opening her mouth to yell for help, she felt a gag shove past her lips. What was this? Not a ball...a...penis? Oh god. She was laying there, blindfolded, handcuffed, with a... -she tongued the latex- ...three-inch cock in her mouth. She tried to shake his hands away as he secured the gag around the back of her head, but to no avail. Expecting to be taken roughly, his soft kisses against her collarbone shocked her. He moved his kisses lower as he unbuttoned her shirt, taking a moment to pull her demi bra down under her swollen breasts and take each into his mouth, swirling his tongue lightly around each nipple while suckling her. Forcing herself to bite back a moan, she found herself sucking and twirling her tongue around the latex cock in her mouth, focusing all of her concentration on doing so as she tried to take her mind off what Tim was doing to her body.

As he moved down, she felt a twinge of relief as she thought of the sexy garter and cheekies she was wearing under her skirt. No grandma panties would be accepted in this situation... Gasping, she felt him tear the delicate fabric of her lingerie away and extend a single finger at her opening. Working slow circles around her clit, she felt herself arching as he slowly slid himself into her. Buried inside of her, he curled his finger up towards the roof of her pussy in a "come hither" motion, and chuckled under his breath as she shuddered. Slowly and rhythmically, he began to slide his finger in and out of her before pulling out unexpectedly. There was a moment of silence where Clarette attempted to gather her thoughts and breath until she head a soft sucking sound and realized he was cleaning her juices off his fingers. Moaning around the cock in her mouth at the thought of him tasting her, she lifted herself off the bed, wanting his mouth on her. Without warning, he slid three fingers inside of her, stretching her for what was to come. She could feel his hot breath on her lips and sighed in satisfaction when he slowly spread her and drew her clit into his mouth...gently at first, then sucking her fully into his mouth while pulsing his fingers in and out of her hot pussy. Unconsciously, she thrust her hip against his mouth, trying to keep pace with his demanding tongue as he sucked her in and out, licking her fully, and darting his tongue all over her as if he couldn't take her in quickly enough - all the while pumping his fingers inside of her. Trying to hold strong, but unable to last any longer against his insistently suckling mouth, she felt her orgasm rising within her, a tidal wave crashing down, and she gripped his head with her knees, holding him to her as she cried out against the gag in her mouth, her body heaving.

Breathing heavily in post-orgasmic bliss, she collapsed down as he released her arms from the bedframe, furrowing only slightly as he recuffed her hands behind her back. Exhausted, she allowed him to do everything without a struggle and when he leaned down and offered to take the gag out, she nodded, still in a haze, but not thinking of leaving a man who could bring about an orgasm of such intensity. She was shoring herself up for what could be coming when she heard the hotel door open briefly and close. Sitting straight up on the bed, blindfold still in place, she panicked. Did he leave her here? Would he do that to her? She was there on the bed, handcuffed, blindfolded, and naked except for the skirt crumpled around her waist. "She's all yours," Tim said. "Actually," a second voice rumbled. "She's all ours."

The bed bowed beside her and she could feel and smell the presence of one of the men, but still gasped in surprise as she felt herself lifted to him. Straddling his waist, her hesitation evaporated, and she wiggled her ass backwards until she felt the head of his cock pressing against her pussy. Sighing, she sank down, impaling him in her come-soaked cunt, and slowly began to ride his shaft as he reached up to capture her swaying breasts. She quickened the pace and moaned along with his groan, feeling herself getting close to a second orgasm when a pair of hands gripped her waist. "Lift." Without questioning, Clarette obediently lifted herself off the stranger she was riding and felt Tim kneel between the man's legs and plunge into her. Slowly at first, he worked up to a hard and heavy pace, fucking her roughly doggy-style before slowly pulling his now slick cock out of her. Sliding several fingers inside of her, he pumped gently before drawing them out and spreading them around her tight, little asshole. Breathing heavily, completely lost in the moment, Clarette only briefly considered what was about to happen as she felt the stranger underneath her slide back into her pussy while Tim lined up his cock with her ass, pulsing at her moans as her sphincter spasmed around him when he pushed past her entrance. Once he was fully inside, the men lay still, allowing her a moment to get used to the sensation of being completely filled.

In a well practiced move, they rolled the threesome onto the side so each man had the freedom to slide in and out as they pleased and quickly developed a rhythm of motion. Fucking her harshly, the stranger in her pussy, Tim in her ass, Clarette's sexual input was completely overwhelmed and she began to moan loudly. "Oh...oh god...oh yeah...Tim...Tim...oh Tim...don't stop...fuck me...fuck my ass..."

"We should have invited a third guy in to shove into her mouth," Tim grunted as he fucked her ass harder. The stranger chuckled. "I think I can help with that. Roll over." As the stranger pulled out of her pussy, Clarette felt strangly empty with just one cock inside of her until the head of a cock rubbed against her lips. "Open your mouth, honey...show Daddy what you can do." Immediately turned on at the nickname and suggested incest, Clarette opened her mouth and pushed her head up and forward to swallow him into her throat, feeling tears sting the corners of her eyes as she did. His groan and fingers lacing through her hair made it worth it. Gripping her head while standing in what she assumed must be a squatting position, he began to fuck her mouth roughly as Tim gripped her waist with one hand, and with the other, began stimulating her clit. Moaning, all she could think about was how hot it would be for the three of them to come together. Pushing her ass into Tim as he slammed up into her, she sucked the stranger harder as he continued to fuck her mouth, and moaned, attempting to warn the men that she was close before she began to climax.

Her whole body writhing, she gagged at the unexpected shoot of semen down her throat before slurping the stranger's cock, emptying him as she cleaned him off. Feeling her anal and vaginal muscles spasm and seeing his friend come in her mouth must have been too much for Tim, who let out a primal yell as he emptied himself into her tight asshole. The three lay together for a few minutes, breathing hard, before the men withdrew. Leaving Clarette on the bed, she listened as the men cleaned themselves up and said their goodbyes. The bed bent to the right as Tim leaned over and kissed her lightly on the mouth. "You were wonderful...let's not let another two years pass before doing that again." Reaching behind her, he carefully unlocked the handcuffs, and pressed a business card into her hand. "Call me. Anytime." She heard his steps retreat and the hotel door open and close.

Slowly reaching up and pulling the blindfold off, she gasped at the stranger standing in the bathroom doorway, looking at her. Her boyfriend. Staring at each other, neither saying a word, she watched as he made his way to the bed and crawled his way up to her. Opening his arms and cuddling her into his chest, he kissed the top of her head. "You go to hotels with strangers often?"

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