Maggie's Night Out

Grabbing her wallet and keys, Maggie leaned down to kiss her two sons on the head.

"Ok, kiddos, I'll be back in a few hours. Marie is going to put you to bed. Marie, dishwasher's dirty so feel free to pile the plates in. I'll be home by ten, kids in bed by 8:30."

Maggie closed the front door behind her, and smiled as she heard her sons exuberantly start asking their babysitter to set up a Nerfgun dotted obstacle course. Maggie took small steps to ensure that her low-healed sandals didn't slide off as she walked down the front porch stairs. Not her typical footwear of choice, but this was not a typical night. In fact, Maggie had never done anything like this in her life before. She wasn't quite sure she was going to go through with it now. Shaking her head to dislodge the doubt, Maggie climbed into her sensible, kid friendly SUV and drove the ten minutes across town in silence. Absentmindedly she picked at the waistband of her skirt. It was a bit tighter at the waist than she remembered. She sighed.

"Two kids and approaching forty will do that," she mumbled to herself.

Still, the skirt nicely showcased her freshly shaven legs, and the pale cleavage barely peeping out of the V-neck of her summery blouse was likely sufficient distraction from her middle. She felt sexy. Not "23 with no stretch marks, turn heads, crop top, itty bitty waist" sexy. She felt confidently sexy. Sexy like a woman who knew what she wanted, had 20 years of experience learning to enjoy her body, could instruct a partner in how to make her cum, and was about to engage in her first clandestine hook up.

Once in the parking lot of her destination, Maggie flipped down the visor of her car, quickly checking to see if her berry lipstick had remained in place on the drive over. One hand reached up to fluff her wavy brown hair as she felt a thrill of excitement loop-de-loop in her stomach. Snapping the visor shut, Maggie took a deep breath to calm her nerves and slid out of the car. She gently tugged down her white skirt, smoothing out the wrinkles, before locking the car behind her. The beep beep of her car locking in the dark parking lot caused Maggie to look around cautiously to see if she was alone. There was only one other car and she knew who belonged to that black Mazda. Quickly Maggie began walking towards the door to the three-story commercial building, shivering as the night breeze slipped around her bare legs.

Once in the lobby, Maggie faced a choice. Climb the three flights of stairs and reach her destination quickly and with heart pounding or take the ancient elevator and prolong the suspense. With a quick exhale Maggie hit the button for the elevator. She pushed the button for the third floor and admired her freshly shaped and painted pale pink nails. A quick image of her fingers wrapped around a penis caused Maggie's pussy lips to begin swelling in anticipation. As the elevator clicked past the second floor, she gave her left nipple a pull with her manicured thumb and index finger. This elevator was taking forever. Biting her lower lip, Maggie glanced around as if remembering she was in public. The elevator quietly dinged as it reached the third floor. Maggie shifted her weight from one foot to another before exiting, appreciating how her thong slipped against her pussy's wet heat.

Standing outside the door that read Dental Care Center, Maggie smiled to herself. Most people were not nearly as excited as she was to visit the dentist. Maggie slipped off her sandals, setting them outside the door. She knew she needed to be as silent as possible from here on out; he did not know she was coming. Treading lightly through the waiting room, dark except for the emergency lights, Maggie wondered how Dr. Winn would react to her showing up unexpectedly. Maggie's lubricating labia betrayed her hopes. Softly Maggie eased the waiting room door open, purposefully allowing her nipples to brush against the door's edge as she eased it past. Shivering from the contact, she peered around the door and towards Dr. Winn's office. His door was half open, throwing a triangle of light into the hallway. Automatically looking to her left to ensure there were no hygienists working late, Maggie began to slowly feel her way down the dimly lit hallway. She trailed the pads of her fingers against the wall, enjoying the sensation of the textured wallpaper. When she was within two feet of his door, Maggie paused, suddenly nervous. What if this was a terrible idea? What if Dr. Winn would think she was delusional for trying to seduce him in his office? Her desire quickly overrode any hesitation and Maggie stepped up to the doorframe. For a brief moment, Dr. Winn didn't notice her presence. Peering solemnly at his computer, he seemed to be finishing up some paperwork. Maggie saw the slight furrow in his brow and noticed how quickly and deftly his fingers moved across the keyboard. This man was so skilled with his hands. Maggie's pussy clenched as she imagined those fingers dexterously urging her towards orgasm.

"Dr. Winn," Maggie breathed out. Startled, he looked up. His eyes, so brown they were almost black, flashed with surprise as he realized who was in his office doorway. Without looking away from her, Dr. Winn closed his laptop and slid it into the right hand desk drawer, turning the key that was in the keyhole.

"Maggie." Dr. Winn's voice was warm and inviting. "What are you doing here?"

"I..." suddenly unsure Maggie briefly considered running. She took two barefoot steps into his office and closed the door behind her. "I had to see you."

"Are you ok? Where are the...?"

Before he could finish his thought, Maggie strode towards Dr. Winn, not breaking eye contact. She adjusted his office chair so that he was facing her, eye level with her navel. She bent down until she was inches from his face, her skirt riding up her behind.

"I needed to see you."

A slow smile spread across Dr. Winn's face as recognition of what was happening dawned. His eyes crinkled in the corners as his cheeks pulled into a smile. Maggie's gaze searched his face as she ran her left index finger down his smooth check, along the jaw, and towards his collar bone. He had a square face, plump lips, and the white, straight teeth of a man who spent his life caring about oral hygiene. She pushed aside blue scrub material so that she could trace his collar bone lightly with her nail. Scrubs were probably not most people's idea of seductive attire, but Maggie loved them. Soft and made without much structure, they could reveal everything. Maggie imagined pressing herself against Dr. Winn and easily feeling his erection through the soft scrub pants.

As Maggie's gaze traveled along Dr. Winn's face, he peered into the v of her blouse. With an exhale, Dr. Winn gazed at the two puffy white mounds edged by simple lace. He envisioned licking along the edge of Maggie's bra and pausing in the small cleft between her breasts. His cock began to awaken, his breathing getting subtly quicker and shallower.

Looking back up to meet Maggie's gaze, he eased his head towards her. Responding in kind, Maggie brushed her lips against his, moving from left to right and back again. For now, she was in control and she enjoyed making them both wait. She had been planning this for two weeks, and she intended to enjoy every second. Leaning back in, Maggie pressed her lips against Dr. Winn's, feeling the pressure of his lips against hers. He began parting his lips, but Maggie refused to open her mouth and allow the kiss to deepen. She moved her lips from his mouth to his jawline, pressing small kisses up towards his ears. She lightly blew into his ear before lathing the earlobe with her tongue. Dr. Winn shifted in the office chair, giving his cock more room to swell as Maggie's lips traveled along his opposite jaw line.

Eager to touch the woman who had appeared in his office door, Dr. Winn cupped Maggie's hips in each of his hands, trying to pull her nearer. Maggie responded to his touch by swaying from one side to the other, and took one step closer. Encouraged, Dr. Winn ran his thumbs from her hip bones to the crease of her thighs and pulled her to him once more. This time she yielded. Maggie stood, pulled Dr. Winn's office chair towards her, and threading her legs between the gap in the arms of the chair and the back, settled her butt on his thighs with her slit centered over his cock.

Dr. Winn rocked his hips into Maggie's pussy. He could feel moist heat through the fabric of his scrubs, causing his cock to pulse. Rhythmically thrusting his hips upwards, he threaded both hands into Maggie's soft waves and pulled her face to his. His desire climbing, he tilted his face to meet hers and met her mouth with parted lips. Alternating between caching her lower lip in his teeth and snaking his tongue to meet hers, Dr. Winn was relentless in his kissing. Maggie began to inhale heavily, unable to fully catch her breathe. She was humping his lap now, desperate to increase the pressure on her pussy lips and clit. For a tantalizing moment during each thrust she could feel the ridge of his cock head brush against her. Pearlescent fluid was beginning to seep around the edges of her thong, leaving a wet patch on his scrub pants.

Maggie pushed her hands against Dr. Winn's chest. With her fingers spread against his pecs, she could feel the solid hardness of his body against her palms. Pulling her hands down towards his nipples, she allowed her fingernails to scratch through his scrubs. Still scratching lightly, she traced loops around his nipples, waiting for them to respond and stiffen. When they did, Dr. Winn sucked air through his teeth. He pulled back from Maggie's swollen, berry-stained lips. His eyes hooded with desire, he uttered a single word.

"Shirt?"

Without waiting for an answer, his fingers began trailing up Maggie's stomach, lifting the fabric from the curve of her abdomen. Instead of continuing up towards her breasts, he slid his hands around her ribs until they rested on her back. He kneaded the pads of his fingertips along her spine. Disappointed with the detour, Maggie crossed her arms in front of her and slipped her blouse over her head.

"I think these are what you were looking for."

Maggie arched her lower back, pushing her lace-cupped breasts closer to his face.

"Mmm, " Dr. Winn exhaled.

Supporting the arch in Maggie's back with his hands, he rotated the desk chair so that he was once again facing the work surface. Maggie reached back, placing her elbows on the desk, causing her back to arch further and her breasts to stretch the lace of her bra. Her nipples were buttons pushing through the fabric, and Dr. Winn could see the shadow of her areola peeking through the gaps in the lace. Maggie brazenly displayed her breasts for him, pussy involuntarily contracting. Maggie was so swollen and wet down below that the string of her thong was being slowly swallowed by her expanding pussy lips. She could feel the fabric brush her clit when she clenched her ass.

Presented with a feast, Dr. Winn happily fell to satiating his desires. Just as he had imagined earlier, he kissed the swell of Maggie's breast at her the bra strap, and began working his way towards where the mounds met. Halfway down, he flicked his tongue under the edge of the fabric and towards her nipple. Maggie gasped and twisted her body, trying to force her nipple to make contact with his tongue. Undeterred by her movement, Dr. Winn held Maggie's hips steady and continued licking towards where he breasts met. He kissed and licked up the slope of her left breast, and brought his left hand up to cup her right. Maggie's breast spilled out of his hand. He lifted his hand as if measuring the weight of her. Squeezing his thumb towards the rest of his palm, Dr. Winn enjoyed the smooth squish of tissue. He flicked his thumb over her nipple, eliciting a quick inhale of breath. Continuing to circle his thumb around and over her nipple, Dr. Winn reached behind Maggie with his right hand and unclasped her bra. She pulled her arms free and allowed the garment to fall to the floor under the desk. Dr. Winn moved his mouth to Maggie's right nipple. When he sucked her into his mouth, Maggie felt fractals of electricity shooting from her nipple to her clit. Allowing herself to be pleasured, Maggie leaned back onto the desk, writhing her hips into the air as Dr. Winn sucked at her nipple, finally scraping his teeth against her skin as he pulled off.

Taking the weight off her elbows, Maggie settled back onto Dr. Winn's lap, leaving more space between her tummy and his chest. She pushed the flat of her palm against the outline of his cock. It twitched into her as she rubbed her hand, open palm, against the length. The looseness of Dr. Winn's scrubs allowed her to grab almost all the way around the shaft of his penis over his clothes. She began gently squeezing and releasing the shaft, moving her hand up and down the six inches of length that was rigidly at attention.

With Maggie working Dr. Winn's cock, he slid his right hand under the outside of her left thigh until he could just reach her pussy with his fingers. What he lacked in range of motion in this position, Dr. Winn made up for in eagerness to pleasure her. He ran his three middle fingers along the sopping line of her cunt. He felt his way up her thong and pushed into her pubic mound, trying to put pressure on her clit. Moving his hand back underneath her, he pulled the string of her thong tight against her body and began moving it left and right so that the fabric scraped against her aroused pussy lips. Unable to wait any longer, Dr. Winn moved the thong to one side and began tracing the outside of Maggie's damp opening. Maggie began thrusting down against his hand, anxious for his fingers to reach high enough to stimulate her clit. On her next thrust, Dr. Winn slid his middle finger into her hole.

"Oh shit," Maggie breathed. She paused in the midst of stroking his cock.

"That bad?"

"No, you know what I mean." Maggie scoffed and Dr. Winn smiled. He added another finger to the one buried in her pussy. "Not bad, not -- ohhhhhhh." She drawled and relaxed her pelvis even more onto his hand.

His cum-leaking cock pushed against the fabric of his scrubs. Dr. Winn pulled Maggie to him and pushed the chair away from the desk in one fluid motion. He lifted her off his lap, helping her to standing, her bare toes curled into the carpet. He looked her up and down. Breasts luxuriously hanging free above hard nipples and a skirt bunched up around her thighs. He wanted to take this woman. He wanted his cock buried so far into her he would lose himself. He reached for the tie that secured his pants. Dr. Winn stepped out of them as he moved towards Maggie in his boxer briefs, scrub shirt forgotten in his haste.

Maggie watched his cock bob as he moved towards her. Maggie wanted to run her hands around his solid thighs. Dr. Winn was what Maggie though a man should be. Hard torso, slightly thicker thighs, and strong arms, but without the excessive definition of a weight lifter. She noticed that he also had some extra weight around his middle, but Maggie was undeterred. She loved the way the curve of his stomach met the hard angles of his hips. Only one thought was running through her mind now, Maggie stepped forward to meet Dr. Winn, eager to have his cock between her legs.

Dr. Winn pushed Maggie up against the wall, one hand kneading her breast. His lips were insistent against hers, and their mouths opened. Slowly, Dr. Winn was grinding his cock against Maggie's mound. She began moaning through their kisses. Her free nipple rubbed against Dr. Winn's chest, her tongue battled with his, and her entire body felt electric. With each moan, Maggie felt Dr. Winn's cock push against her. Maggie gripped his ass cheeks and lifted one leg, wrapping it around his hips. Her crotch hit his cock with more pressure. This time it was his turn to moan

Maggie broke away from the embrace to drop to her knees. She tugged Dr. Winn's briefs down his body and he helpfully stepped out of them. She gripped his thick, cut cock with both hands. Pressing a thumb under the head, she jerked him off. Her hands were sticky with fluid as they moved in tandem up and down the shaft. She leaned in to wrap her lips around him when she felt him grab her elbows and lift her back to standing.

"No time, need you now," he grunted.

Maggie found herself pushed again against the wall as Dr. Winn guided her legs apart. She was expecting his cock, but not what happened next. Dr. Winn slid Maggie's thong down her legs and pushed his thigh into her dripping pussy. Gasping, Maggie was lifted slightly off the ground by his leg. At the same time Dr. Winn dropped his head to resume sucking on her nipples. Caught off guard, Maggie found herself on the brink of orgasm. As Dr. Winn sucked and teased her aching breast, Maggie's pussy began clenching against the force of his thigh. She tipped over the edge and into bliss, her entire body awake and alive with pleasure. Her pelvis rocked against his body and she heard herself moaning, gripping his back as if she might fall.

"Oh, I'm sorry, I didn't mean to." Maggie looked sheepish.

"No apology needed," Dr. Winn breathed heavily. "Keep going?"

In answer, Maggie looked up, catching his dark eyes studying her face. She slid her hands around his head and pulled him back in for kiss. Dr. Winn deserved pleasure, and she was ready to oblige. Deepening the kiss, Maggie and Dr. Winn took turns sliding their tongues into each other's mouths. Maggie gripped his ass and pulled his cock tight against her pelvis.

"How do you want me?" she breathed out, between kisses.

"Just like this."

Dr. Winn lifted Maggie by her upper thighs, settling her weight between the wall and his body. Maggie slung her arms around his shoulders, taking some of her weight, as he guided his cock between her swollen lips with one hand. She was so wet and ready that Dr. Winn was immediately buried in Maggie's pussy. He knew he wouldn't last long. Maggie began squeezing her vaginal walls around his cock, urging him closer to orgasm. Short, quick thrust were all he could manage as he watched Maggie ride his cock. Wanting to give as good as she got, Maggie began whispering how she could feel Dr. Winn's cock plunge into her, the flared head rubbing against her insides. He began grunting lightly with each thrust, close to the point of no return.

Unexpectedly, Maggie began feeling an itching tension building. She could count on one hand the number of time she'd had multiple orgasms, but this seemed to be one of those times. Her own desire building, Maggie frantically squeezed her pussy walls and began grinding against Dr. Winn at the end of each thrust. She slipped one hand down to her nipple, twisting gently.

Maggie felt Dr. Winn's back muscles tense. Piercing deep into her he began to cum. They both continued grinding. Feeling warm liquid inside her, Maggie reached climax again. In unison they moaned, muscles clenching, cock twitching, pleasure swirling. As they began to relax, Dr. Winn leaned down to give Maggie one last kiss.

Ten minutes later Dr. Winn was back in his scrub pants. He and Maggie sat on the floor of his office, his arm around her shoulders. She was leaning against him and absentmindedly folding the fabric of his top in her fingers.

"You look good in scrubs."

Maggie looked over at Dr. Winn. "Much more comfy than getting back into that skirt and top. Glad you keep extra here in case of emergency," she paused, a small smile settling onto her face, "Dr. Winn."

"Really getting off on the doctor thing today, huh Mags? I'm not gonna complain. But where are the kids?"

"Oh, they're with Maria. I told her we wouldn't be back until ten, so we still have a good hour and a half. Wanna order takeout?" Maggie began to stand up, looking for her phone so she could place an order.