Cary stood in the private terminal of the executive airport, the low hum of engines in the distance growing louder as the sleek Gulfstream descended through the dusky sky. Through the tall glass windows, she watched the jet touch down gracefully, the late light glinting off its silver body as it taxied toward her.
Cary studied her reflection in the mirror and liked what she saw. Her black-laced leather bustier revealed just enough cleavage to showcase her D-cup breasts, and her matching thigh-length mini-dress highlighted her toned, dancer’s legs. Her curly, silver-gray hair framed a face that defied her sixty-three years. Strangers often guessed her age at forty-five, never more. Confidence shimmered from her like heat off the tarmac.
As the jet door opened and the stairway unfolded, Gary appeared in the opening, broad-shouldered, poised, and unmistakably masculine. The image of him from her previous encounter at the Chicago real-estate convention sent a subtle jolt through Cary’s core, an electric memory that ignited something low and warm in her.
Then Ray stepped into view behind him, and her anticipation spiked higher. She remembered every detail of their night together, their scent, their touch, the taste of them, and wondered just how far they might go this time.
But let’s not get ahead of the story.
Two weeks ago, Cary had been immersed in her world of contracts and closings, the capable, respected CEO of her real estate firm. Driven, polished, and intuitive, she was everything a leader should be, and privately, far more. Though her days were packed with deals and decisions, Cary had cultivated a luscious secret life, a sensual interior she protected and nourished.
Between these convention getaways, she satisfied her cravings in the most intimate of ways.
One particular evening, after a long bath and a glass of chilled white wine, Cary reclined across her California king bed, wearing the deep-cut red dress she’d worn to that Chicago convention, the one that had first captured Gary and Ray’s attention. With her iPad casting crystal-clear scenes from Pornhub onto the 65-inch screen mounted on the wall, she searched for a familiar fantasy: older woman threesome, slow and intense.
Cary found the MFM feature, two tall, mature, sculpted lovers who reminded her of her Chicago companions, easing an elegant woman into bliss. But this video was something different, more daring, a scenario she wanted to explore. With her favorite vibrator in one hand, Cary reached for a second toy, a nine-inch dildo. What would it feel like to have two cocks at once filling her, a DP, one in the front, one in the back?
As the scene on the screen unfolded, Cary watched the actress submit to being taken together by two cocks penetrating her openings, and Cary did the same. After buzzing her clit, Cary moved the bullet to her folds, teasing, before plunging deep inside, her slickness sucking the vibrator in, sending a jolt through her core.
With her left hand, she placed the lubed phallus against her other opening, once considered taboo. Ever so gently, Cary inched the head in, moving it deeper until part of its length disappeared, a new experience for her.
As the porn star succumbed to the dual pleasure and orgasmed, pinned between the two hunks, Cary let herself go. The room echoed with loud gasps and moans, the sheets beneath her soaked by the time she came, hips arched, fingers trembling, two erogenous zones penetrated, bringing a new sensation, one she would like to experience for real.
Later that week, as if summoned by her orgasmic energy, an email appeared from Gary.
“We’ve been thinking about you, Cary. Want to come back to Chicago? Northwestern’s home in two weeks, we’ll fly you up. Ray and I have something in mind.”
She smiled, heat blooming at her center.
Cary typed an enthusiastic yes, attaching a fresh mirror selfie: high-cut black lace panties, barely-there bra, and her hair tousled just right. The message needed no words.
Now, on the tarmac, she felt the moment stretch as she stepped into their view. Both men descended toward her with steady, confident strides. Gary’s eyes raked her body, slowly, appreciatively, while Ray’s mouth curled into that grin she remembered so well: playful and hungry.
When they embraced her, one on each side, the warmth of their bodies and the press of strong hands at her waist sent a thrill spiraling through her. They pulled her in tighter than necessary. She didn’t resist.
Cary sensed this wasn’t going to be a repeat of last time; it was going to be something more.
Cary stepped into the Gulfstream and felt an immediate thrill. The interior looked more like an upscale Manhattan penthouse than an aircraft. Soft cream leather seats with quilted stitching and brushed gold accents surrounded sleek wood paneling and expansive, tinted windows. The lighting was low and warm, a golden glow that made everyone’s skin look gorgeous. A bottle of Dom chilled in a silver bucket on the wet bar. Pale suede carpeting muffled her heels as she walked the aisle, hips swaying, aware of both men watching her every step.
She paused for a moment to take it all in.
“This is next-level,” she said, slowly turning in place to appreciate the layout. Four oversized seats faced each other, two on each side, and a long leather divan stretched behind them, with fluffy pillows and a cashmere throw.
Gary offered her a flute of champagne, and Cary accepted, their fingers grazing. “Only the best for our favorite travel companion,” he said, eyes twinkling with desire.
Cary sat across from them, legs crossed with intent, her daring top just right to offer them both a prime view of her cleavage as they settled in for takeoff. Their conversation started light, catching up on work, travel, bits of gossip from the real estate world, and Gary’s consulting firm. Ray sipped whiskey neat, his gaze rarely leaving her face.
Cary returned the sly smile. “Well, just so you know, I’ve been keeping busy. There was San Diego,” Cary purred. “A hunk named John, ex-Navy SEAL, great body. We damn near did it right on Coronado Beach. Later, I taught him how to make love to an older woman. I was in control the whole time,” she said, legs slowly uncrossing. “And I liked it.”
She let that hang a moment, then added, “I also had a little girl-on-girl escape in Myrtle Beach… a yoga instructor, Cindy. Gorgeous. Taught me how to stretch in all the right ways.” She let the word “stretch” linger.
Gary and Ray both leaned in.
“She was young,” Cary continued, brushing a finger along the stem of her glass. “Tight, toned, utterly devoted to my pleasure. That night ended with my thighs shaking, my face buried between hers. I swear we climaxed together.”
Ray exhaled sharply, visibly adjusting his jeans.
Eventually, he leaned forward and smiled. “Shay, you know, my second wife, we flew her in this afternoon before coming to get you. She’s already at our suite in the Ritz-Carlton and is excited to meet you tomorrow at the game.” His eyes darkened with a suggestion Cary didn’t miss.
She sipped her champagne as both men stared, stunned and turned on.
Gary finally found his voice: “So you’ve been very… productive.”
“Inspired,” Cary smiled.
Gary leaned forward, fingers brushing her knee. “And what are you most looking forward to this weekend?”
Cary tilted her head, lips curling in a slow, sexy smile.
“Well, the football game for one… and… I was thinking about… a DP… maybe a mile-high version.
Gary didn’t flinch, didn’t even blink. He looked at Ray, then back at her. “We can handle that.”
“But first,” Cary purred, “I’ve been dreaming about tasting you two.”
Cary bit her bottom lip and leaned back into the plush seat, legs spreading just enough to hint at the lace beneath her skirt. The jet engines roared outside on their way to Chi-Town, but in that moment, there was only silence in the cabin, charged, promising.
The mile-high fantasy was no longer just a suggestion. It was a destination.
Cary rose slowly from her plush leather seat. She faced the two men across from her, her gaze playful but unmistakably commanding.
“Strip,” she said, her voice low and sultry, the single word curling around them like smoke. “I want to see you get hard.”
Neither Gary nor Ray hesitated. With the low hum of the jet engines and the golden lighting casting warm shadows on their skin, they stood. Jackets hit the floor. Shirts peeled away. Bare chests rose and fell with growing anticipation. Belts unbuckled. Pants dropped.
Cary watched as they stepped free of their boxers, Ray first, thick and already half-hard, his impressive nine inches growing longer by the second. Gary followed, his cock shorter but deliciously thick, veins pulsing as it swelled to full length.
She let out a breath, eyes locked on their cocks as they stood before her, completely naked, bodies taut with need. “Beautiful,” she whispered.
Then, with deliberate slowness, Cary began to undress. Her hips rolled in a sultry rhythm as she slid her skirt down her long legs, revealing the curve of her hips framed in black lace panties. She stepped out with grace, barefoot now on the suede carpet.
Their eyes tracked her every move.
She reached for the lace of her bustier, undoing each one, teasing, revealing her breasts straining against the fabric, her nipples dark and erect, now visible.
The bustier slipped from her breasts to the floor.
“Stroke yourselves,” she said softly, her gaze now locked on their erections.
Gary and Ray obeyed, wrapping their fists around their shafts, slowly pulling, the sound of skin on skin filling the cabin. Cary watched as Gary’s cock thickened even more, a drop of pre-cum pearling at the tip. Ray’s swollen head flushed purple, veins thick and throbbing.
Cary lowered herself gracefully to her knees between them, her panties still on, a deliberate visual for their pleasure.
No hesitation. She knew what she wanted.
She took Ray’s cock in one smooth, hungry motion, her lips stretched wide as she swallowed nearly all of him. He groaned, head dropping back, hand gripping the armrest to stay grounded. Her hands were busy too, stroking Gary’s shaft, her fingers wrapping around his girth with skillful pressure.
Then she switched, mouth on Gary, taking him deep, while her hand glided up and down Ray’s shaft, her thumb circling the underside of his tip.
They moaned her name in turn. “Cary… fuck… Cary…”
Again and again, she alternated, mouth to cock, hand to shaft, each transition seamless, confident, utterly controlled. She kept them teetering on the edge, knowing exactly how to pull back before either could tip over.
And then she slowed it down.
Her lips barely brushed Gary’s cock as her hand cradled Ray’s balls, stroking softly. She seductively licked their shafts from tip to base, tongue flat and slow, savoring every reaction. Her fingers played, teasing the entrance to their asses, and they both groaned low and deep, their bodies trembling from the intensity.
Then Cary stopped altogether. Now it was their turn.
She stood and slowly wriggled out of her panties, revealing her slick, glistening pussy, shaved and swollen with arousal. With a knowing smile, chest heaving, lips parted, Cary reached for her pocketbook and tossed Ray a tube of lube oil.
Then she walked to the divan, her ass swaying as she went. Cary turned, lowered herself slowly onto the soft leather, reclining, one leg bent, the other stretched, exposing herself, revealing a butt-plug fully inserted.
“I wanted to be ready for you,” Cary purred as she removed it.
Ray stood before her, his presence commanding and unmistakably ready. His cock glowed with the sheen of the oil. The heat in the room shifted.
Cary looked at him, and her eyes widened slightly with lust, her smile welcoming. Ray eased onto the divan behind her, leaning back with his arms folded behind his head, cock proudly waiting. Cary took her time joining him, one knee at a time, her bare thighs straddling his waist, her back towards him.
With breath drawn in, slow and steady, she lowered herself onto him, Ray filling that forbidden zone, deep, penetrating.
The stretch was intense. She gasped, but didn’t stop. Ray’s hands gripped her waist, steadying her. Slowly, purposefully, she rocked back and forth, finding a rhythm that let her breathe.
Gary moved closer. He knelt before her, his hands parting her legs gently, lips pressing reverently to her inner thighs. Cary let her head fall back, hips now circling. The sensation of Ray buried beneath her, Gary’s mouth teasing her folds, blurred her edges.
Gary looked up at her, eyes soft but intent, and she felt it again, that rising tide of connection. Not just lust. Something more.
He kissed her once, just above her clit, then rose to his knees and met her mouth again.
“I want you inside me,” she whispered against his lips.
Cary lifted slightly, holding herself poised as Gary pressed against her entrance. Slowly, with exquisite patience, he entered her. Her body trembled with the sensation of being so thoroughly filled, above and below, her pulse quickening.
Now fully surrounded, Cary let out a low moan as the pressure, the warmth, the connection overwhelmed her. She moved slowly, instinctively, adjusting to the twin fullness, her hips rolling as Ray began to thrust beneath her, while Gary moved with careful precision in front.
They began to move as one. Ray’s hips rising, Gary’s body pressing forward, their rhythm perfect, a balance of tension and release. Cary was the center of something primal and beautiful. Every thrust excited her.
Gary kissed her again, this time deeper. She reached for his shoulders, pulling him closer, their sweat mixing as her body strained and softened all at once. Ray’s hands roamed her breasts, pinching and teasing, while Gary’s fingers circled her clit in tight, deliberate pulses.
Cary’s breathing became erratic. Her skin flushed. Her toes curled against the leather.
“Gary,” she whispered, her voice trembling. He opened his eyes.
That was all she needed. Her release rose with a fury she couldn’t hold back. She came in a burst of gasps and shudders, crying out his name, her body convulsing, writhing between them.
Gary held her through it, with Ray beneath her, hands gripping her thighs, chasing his own edge.
Cary shifted forward into Gary’s arms, their skin sticky with effort and sweat. Ray slipped from beneath her, then stepped away, giving them space.
Gary caught her, laid her gently back on the divan. “Are you okay?” he asked, brushing a thumb over her cheek.
She nodded, still breathless, smiling through her haze. “Better than okay.”
They traded places without a word. This time, Gary took the reclined position. Cary climbed atop him, cowgirl, her body still trembling but eager, welcoming.
She slid down onto him slowly, facing him, hands braced on his chest, their gazes locked. Gary filled her again, and she sighed, this time from tenderness more than urgency.
Their lips met again, slower now, exploring with warmth. Her hips rose and fell in smooth waves, while Gary’s hands roamed her back, her waist, her breasts. They moved together like dancers, their tempo easy, grounded, intimate.
Then she felt Ray again, his hands gliding along her back, his lips at her neck. She felt the pressure at her backside and gasped in anticipation, but this time there was no rush. Ray eased in behind her, his movements tender, careful, deliberate.
Cary exhaled as he entered, the stretch intense once more, but this time made easier by a growing trust. Gary’s hands cupped her breasts as she rose above him, Ray’s grip steadying her hips from behind.
The rhythm built again, Cary suspended between them, every inch of her body alive, on fire. Their hands, their mouths, their eyes, it was all so much, too much, and just enough.
Her climax came again, quieter this time but no less powerful, a blooming from her center that pulsed outward, stealing her breath.
Gary followed, holding her close as his body tensed and released, his warmth filling her. Ray, last to the summit, let out a growl behind as he spilled into her, his hand still gripping her hip tightly.
When it was over, Ray kissed her shoulder and headed off toward the bathroom. Cary collapsed forward onto Gary’s chest, both of them flushed, breathing hard.
He wrapped his arms around her, and for long moments, they didn’t speak. They held each other, letting their bodies calm and their hearts sync.
Finally, Gary shifted beneath her. “We should probably clean up.”
“Shower?” she murmured.
He smiled. “Together.”
When they returned, dressed and freshly scrubbed, Cary took the seat beside Gary, her hand resting lightly on his thigh. Ray sat across from them, smiling with satisfaction.
Just then, the captain’s voice came over the intercom:
“Gary, we’re on final descent into Chicago. Touch down in thirty minutes.”
The three of them looked at one another.
In perfect unison, they said, “Touchdown.”
And then they laughed, easy, full, and free.
…
The light filtered under the curtains. Cary found herself wrapped in Gary’s arms, a feeling she longed for, waking up beside a lover. She had felt the void ever since Mark had passed five years ago.
“Nice.”
She pulled the cord as early morning sunshine flooded the room, revealing the magnificent view the corner suite offered. Straight ahead was the Lake Michigan waterfront, and to her right, downtown Chicago.
“Look who is Miss Rise and Shine,” Gary sleepily said, rolling over to face Cary, who gently placed a kiss on his cheek.
“You promised me a full day, and I am ready to get started, Mr. Sleepyhead.”
“As you wish,” reminding Cary of one of her favorite lines from the movie, The Princess Bride.
Gary was an excellent guide. After breakfast, he took Cary to the Shedd Aquarium, followed by the Field Museum. They worked up an appetite biking ten miles on the Lakefront Trail, and had lunch at a local Italian joint, Cary’s first taste of Chicago’s famous deep-dish pizza. She thought it was good, but nothing like the NY-style pizza she grew up with on Long Island.
When they returned to the Ritz, they decided to shower and rest before leaving for Ryan Field, where tailgating would precede the game.
In the oversized shower, more like the kind found in a luxury spa, they took turns lathering each other’s backs and then their fronts. When they ended with a passionate kiss, they knew that rest would have to wait.
They sat on the bed naked, facing each other, legs overlapping. They left the curtains open, wanting to fully take in each other with nothing to hide.
Cary took his cock with both hands, smoothly gliding over its length and thickness. Gary had one hand caressing her boobs, the fingers on the other gently parting her folds down below.
They looked at each other, eyes locked, and knew this was how they would come, mutual, from each other’s touch. And so, they did, rocking together until a tidal wave overwhelmed them both.
…
Cary first met Shay in the back of Ray’s Bentley Continental on the way to the game. She was tall, beautiful, and blonde, a double of a younger Michelle Pfeiffer. And even though they were all wearing vintage Northwestern jerseys, there was no mistaking those dangerous curves out front covered by the Wildcat logo. Cary could also tell she had a wild side ready to let loose.
The tailgate was another scene altogether: Winnebago’s, camper vans, luxury cars, right down to undergrad junkers; all using every portable cooking device known to man to put out the most delicious food. And the amount of drinking was off scale. No wonder they all made it into the stadium in time for kickoff.
The game itself was exciting with nonstop high-scoring action. It wasn’t until the fourth quarter that Northwestern pulled ahead and won by two touchdowns. Gary, Ray, and the rest of the alum players spent most of their time high-fiving each other, leaving the WAGS (Wives and Girlfriends) on their own. Cary and Shay got to know each other pretty well.
…
By the time the group returned to the hotel, it was nearing midnight. Gary and Cary returned to their room to change. He donned a pair of black silk pajamas, while she opted for a daring, low-cut bra that accentuated her cleavage and a short black skirt.
Ray had already put out the pot, marijuana being legal in Illinois, and soon the foursome was buzzed. Cary, next to Shay on the couch, began to make out, putting on a show for the boys. First off came Cary’s top, followed by Shay’s gown, their hands playing with each other’s boobs, nipples standing at attention. Shay’s were youthful and bouncy, Cary’s a bit heavier, both massively impressive. They were lost in one another.
Then they shed their bottoms, reaching down below, instinctively knowing what turned the other on; Shay knelt over Cary and kissed and sucked on her clit, taking her to new heights, as only a woman could, and when Cary came, it was different, from a woman’s touch.
Cary returned the favor, her two fingers searching for Shay’s G-spot, Shay guiding her hand. With Cary’s fingers probing inside, together they played with Shay’s clit, massaging until she let out a soft, satisfied moan, completely surrendering to Cary.
Gary and Ray had their hardened dicks out, voyeurs to the girl-on-girl action, and when they couldn’t stand watching any further, they joined in. What followed could only be described as frenzied fucking.
Shay lay spread-eagled on her back on the couch. Her head was turned, and she was giving Ray, standing alongside her, a most sensuous blow job. As his wife, she knew all the right spots to hit. She would tenderly suck his head with her lips, then slide her tongue down his shaft, before coming back up to flick his underside. With one hand, she would cradle his balls, and with the other, alternately make circular motions, driving him wild. His moans echoed around the room. When she finally took him deep throat, her mouth engulfed his length.
Cary, also on the couch, was on all fours, her fingers moving in Shay’s pussy, her lips butterflying her clit, giving Shay what she wanted. Cary’s ass was raised, and Gary was behind her, rubbing oil on her back, letting some drip into the fold of her cheeks. She could feel his presence, but sensed hesitation on his part.
Cary reached behind and placed her own finger at her back entrance.
“Yes, Gary, this is what I want, to feel you in there.”
With that, Gary gently entered and moved carefully until Cary had taken all of him. Then slowly, as Cary gave her approval, Gary picked up speed, until his piston-like movements blended with her screams for him to cum.
Cary could feel his hotness inside.
Ray came next, pulling out of Shay’s mouth and jerking on her tits, long streams over her perfect body.
Cary moved up onto Shay, her silver-gray hair contrasting with the blonde’s ringlets. Then, in one motion, Cary bent down and sucked one long ribbon into her mouth and gave Shay a steamy cum kiss. A nice way to finish what the two of them had started
Shay had other ideas, however, and suggested they all head for the bedroom, “To get more creative.” They did, exploring numerous positions and possibilities deep into the night.
But for Cary, savoring that moment, with Gary nestled now alongside her, that is what she would remember from this perfect day.
…
The following afternoon, with the corporate jet down for routine maintenance, Cary rode with Gary to Chicago Midway and her commercial flight back home. They had said their real goodbyes earlier at the hotel. Now, as she headed to the main doors, she turned and blew Gary a kiss just as he was pulling away from the curb. He air-kissed her back.
Now, she had a long, interrupted stretch of work, but oh, what memories to carry her until her next adventure.
