Business Trip

Jill had to go out of town on a business trip. All work and no play makes even Jill dull. Business trips and conferences gave her six or eight chances a year to play in a special way.

Jill and Big Mike had a marriage that suited them both. Both highly-sexed, night in and night out they pleasured each other regularly, but once in a while each of them wanted something different, something the other didn’t begrudge or feel jealous about, but wasn’t interested in being part of. Jill’s business trips and conferences gave them the chance to indulge, kept those kinky desires from building up, and made their marriage a success.

Jill was big in ways that suited Big Mike, and attracted men like flies to a honey pot. Her boobs were a tit-man’s wet dream: 36D’s, with dollar-size aureole and stiff little nipples enhanced by piercings, usually little barbells. Her boobs had begun to sag as she entered her forties, but she favored open cup shelf bras that joined with her usual V-neck silk blouses and tunics to display her assets to great advantage. From first sight, everyone knew Jill as a sexual creature flaunting her sexuality.

If her boob-show didn’t get the point across, her flared hips, apple bottom, muscular thighs, and short, tight skirts certainly did.

Her waist was a little thicker, her dark hair color was no longer all natural. but the black with red undertones went well with the dark lipstick on her pouty lips.

The first day of the conference over, her torso was draped in a red silk tunic, beneath it, a sheer silk corset disguised her thickening waist, and emphasized her boobs and butt. As she entered the bar her butt moved in that short stretchy skirt, every step a twerk because of her high heels.

She’d come away from the hotel/conference center district to visit a bar more popular with twenty-somethings. When she walked in, everyone knew there was a cougar on the prowl. Midweek, there were more young jocks and overgrown frat-boys out than their post-coed and jockette counterparts. Tough hunting for the young men made a target-rich environment for Jill, except that her special outings made for special needs.

Jill had never had sex with any one man who was better than Big Mike. On her business outings she sought out pairs of young men. Every now and then, it takes two to tango.

She spotted her target pair, spoke with the bartender, then approached the two innocents. “May I join you fellows?”

One, a polite young fellow in a sport shirt, faded khakis, and Vans, said, “Yes, ma’am.”

The other, in polo, jeans, and converse, just gulped and nodded.

“I’m Jill. What are your names?”

Khakis, wide-eyed to take her entire form in without staring, gave his as Dean. Jeans, eyes glued to Jill’s deep cleavage, said, “Charlie.”

Just then the waitress arrived with the tequila shots Jill had ordered, and Charlie’s credit card.

“I paid your tab and bought us a round,” Jill said. “Cheers!”

“Hey Charlie,” she said, after they’d had the salt, tequila, and lime. “I love the way you keep staring at my boobs.”

His head popped up and he started stammering out an apology.

“No,” she said. “I seriously love it. Look around for a minute though, guys. The future Mrs. Charlie and the future Mrs. Dean aren’t in here tonight. If you overlook me, you probably aren’t getting laid with anyone who’s in here tonight. But don’t overlook me. Those boobs you’re getting an eyeful of, how’d you like to lay your dick between them? Tittyfuck me and shoot all over my face?”

“Dean,” she ground back against him, “You ever fuck an ass like mine? You want to?”

“Jesus, lady!”

“Jill, you have my full attention.”

“I need both of your full attention, back in my hotel room for the rest of the night. How about it? Package deal. Both of you together. What do you say?”

In no time they were all back at Jill’s hotel room where the tequila, lime, and salt Big Mike had ordered were waiting.

Jill set up more shots, then brought the young men into the shower with her.

Their eyes grew wide at the sight of her nude body. In the shower they each soaped and groped one of her breasts and one of her ass cheeks. Their hands bumped together in her ass crack and on her pussy mound. Their fingers slid across her lower lips as they took turns kissing her upper ones.

Jill ran a soapy wash cloth over Dean’s smooth chest, his wiry shoulders and down across his muscular buttocks. She worked it around his groin, beside his dangling ball sack and above and around his cock.

The water sluiced down, rinsing them clean.

It was a fine tool for the job, she thought, slender and long, perhaps 8″, a good size but not overwhelming. It was hard and standing out from his body, angling out, up, and slightly to the left. She slid to her knees and took it in her mouth.

She held the head in her mouth and worked her lips around the ridge and tongued the underside.

Dean moaned with excitement.

Hands were in Jill’s hair. She realized they were Charlie’s and that he was working shampoo into her hair, washing it as she sucked his friend’s cock. The tenderness of it humanized the animal acts they were engaged in.

After a few moments, she stood and turned from Dean to Charlie to repeat the cleaning ritual. Charlie’s muscles were more defined than Dean’s, his body somehow more compact and dense, coiled tighter. His buttocks were more muscular. His cock was thicker, similar in length. Semi-tumescent when she first put her mouth on it, it stiffened, grew, and rose into an upward curve as she sucked eagerly. She was pleased to feel Dean’s fingers sliding up under the curve of her ass to work gently across her pussy lips. He had a sense of timing and terrain because the fingertips sought out the area above her clit instead of trying to prematurely penetrate her.

Clean, titillated, and stimulated, Jill rose, turned off the shower and exited. She found towels and robes, and invited the young men to join her in the bed.

Comfortably settled with one of them on either side of her, she told them, “There’s one more thing we need to take care of before we get serious about taking care of each other. My husband wants to talk with you, so I’m going to video call him.”

The young men were shocked.

“It’s cool,” said Jill, and made the connection.

At home, Big Mike was expecting the call. His face filled the screen. “Hi guys!”

“Hello, sir,” said Dean. One of his hands was busy tweaking Jill’s pierced nipple.

“Hi,” said Charlie, with a little wave.

“Guys, here’s the deal: Jill is going to do shit with you that you’ve probably only dreamed of, but you are NOT porn actors making porn. Treat her with respect, concentrate on HER pleasure. Make sure she cums first and frequently. If you do, it’s going to be a long night with a lot of fun. Also, get your phones and send me your contact info.”

The young men scrambled to comply. Quickly Big Mike grabbed a screen shot and texted it to the two. He had them show him the image: the two of them each sucking on one of Jill’s love-melons, her face outside the frame. “Okay fellas. Turn your phones off. This is your souvenir picture, no more. Jill doesn’t need shit out there fucking up her business career. Thanks for being cool, now have fun and pump her full of cum. Jill, I love you!”

The youngsters didn’t know, but Jill had set up a motion activated camera atop the room TV, Big Mike would be able to see all the room action live, and it would be available for the two of them to view together when she returned home.

With the two lying on their backs, Jill knelt on the bed facing their feet and returned to her cocksucking. Her magnificent ass and pussy were in their faces. They caressed her cheeks. Dean returned his fingers to her clit. Charlie massaged the surface of her pussy, encouraging the flow of lubrication and opening of the flower.

Jill worked Charlie’s thick cock into her mouth and took it well into her mouth. With one hand she stroked his shaft and caressed his balls. With the other she did the same for Dean. Then she switched cocks. As her arousal increased, she slid the slender member into her throat, holding it there and allowing the spasming brought on by her gagging to stimulate him.

Dean moaned in appreciation, one hand tangling in her damp hair. His fingers stopped moving, but now her pussy was wide open and Charlie aggressively penetrated it with two fingers, searching upward across the front for the legendary g-spot.

She pulled her mouth off Dean, moaned her approval of Charlie’s fingering, and captured his cock between her lips. Sheathing it into her throat, she hummed on it. Dean’s fingers got back to work atop her clit. Charlie’s stopped moving, but pressed into her.

She bounced her mouth from one cock to the other, keeping both young men on a razor’s edge of arousal. Meanwhile, their hands spiraled her upwards until trembling she tumbled over into a highly satisfying g-spot plus clit orgasm. She clutched at the two cocks, panting out, “Ah, ah, uh, unh, uh huh, uh huh, Oh yes!”

After she calmed down, she turned around. “Thanks guys, now it’s time to fuck. Dean, you’re first. Charlie, like Big Mike said, we aren’t making a porn. It’s kind of hard for two to go into one — maybe we can try that later — do what you like, get a drink if you want.” She flopped on her back, and let her knees fall outward.

Dean rolled up between them. He knelt before the altar that was her body, drinking in the sight of her lust-flushed face, the erect nipples on her big breasts, and the delta of hair pointing him to her swollen, slick, and open pussy. He used one hand to aim his cock, and worked the head up and down. He lay on her and dry-humped her. The underside of his cock pistoned slowly in the groove, teasing her delicate labia and clit.

She encouraged him, “That’s nice. Mmm, yeah, work it like that.” Her hips pushed her up to meet him, Her hands were on his back, pulling him close. She whispered at the top of his head, “Put that sweet cock in me now, Dean.”

Pulling his hips back, he used his hand to guide the head to the well-lubricated opening. He lodged the head in her love canal, then eased himself all the way in.

She hissed with pleasure. He matched it with a grunt.

Dean set up a rhythm with long steady strokes. Jill rolled her hips beneath him, so that his cock slid along the underside of her clit, and then, with a kind of a waggle inside her, angled up to stimulate the area of the g-spot. Magical!

Jill felt herself building quickly toward another orgasm. She thought to add a Kegel-squeeze to her motions. She was moaning on her exhalations and hissing on the inhalations, “Uhhh, ysss, uhh, ysss….”

Dean felt the rhythmic clenching of the Kegels squeezing his cock. It set him on a path to inevitable impending orgasm. “Uh, yeah, oh, jeez, uh…” He couldn’t maintain the steady pace, but started bucking and pounding for all he was worth.

The extra depth and pressure, the clashing of his pubic bone with hers, combined to roll Jill over the edge. She clutched at Dean’s back, and pumped her hips up at him. Her head thrown back, she moaned out her wordless ecstasy.

Dean grunted into her neck and pumped his seed into her, balls tightening as his cock throbbed out four or five spasms.

His weight rested on her, pinning her to the bed. His clenched ass muscles held his softening cock deep inside her.

She rolled against him, gently stimulating herself in the afterglow.

He lifted his head to say, “Gosh, that was so hot! I’m sorry if I finished too fast.”

She kissed him and said, “Honey, it was great, and lasted long enough for round one. That’s why I brought two of you here, and why I like you young fellows. You’ll be ready for round two soon enough. Before we’re done, I want your cock in my ass.”

She kissed him again. “Charlie, it’s your turn.”

He was sitting in the nearby chair, and had actually poured himself another shot of the tequila. Now he downed it and moved toward the bed. Sloppy seconds. The young man had heard the term and it always seemed negative, like you were second best, or like there was something less about the woman who participated, but in this moment he was turned on. His cock was as hard as it had ever been in his life. He gazed down at Jill’s splayed form.

Her eyes were lidded with lust and sensual pleasure, her nostrils flared, her lips pouted around her open mouth. A flush rose from her chest to her neck and cheeks. Sweat beaded her cleavage and shone on her belly. Her breasts sagged outward, the nipples erect nubbins. Her pubes lay matted with a mix of fluids. Her legs flopped outward. Her exposed pussy, rimmed with a froth of love juice, shone bright pink, deep red and streaked with white.

Sitting beside her, Charlie lay his hand flat on her pubic mound and rubbed it, sliding his fingers into the damp and welcoming canal below.

Jill had seen many an attitude among young men at this moment. Some could not perform, some repulsed by what had recently attracted them, some only able to act like animals and disdaining her for her part. This kid was learning how much he loved it. She egged him on, “That’s it, finger my cumhole, rub me! God it feels good. Doesn’t my pussy look wonderful? This is how it’s meant to be. Push those fingers up inside me. Oh, that’s good!”

And it was good. She was already on the verge of another orgasm.

Charlie pulled two fingers, dripping goo, from her, brought them to her face, rubbed them on her lips — she licked at them eagerly — then he kissed her.

Her hand went to his cock, grasping the thickness, pulling him to her.

He rolled above her and plunged, full length, into the welcoming cum-pool of her pussy. “So good!” He said. He immediately set up a jack-hammering rhythm that had the bed flexing with the dual load and then rebounding to push her onto his descending dick.

In no time Jill came, gasping, legs twitching and jerking, pussy clasping and spasming around Charlie’s thick dick.

He move upward in relationship to her, so his cock was scraping directly across her clit, and his pubic bone clashing with hers on every downstroke.

Squealing and moaning, she came again.

The wide open dripping slackness of her pussy lent Charlie an endurance beyond what his hard fucking had anyone expecting.

As she descended from the newest climax, she calmed his motions. “Now you lie on your back and let me ride.”

They changed positions. She posted on him, bouncing up and down. Her massive breasts flopped and bounced enchantingly. Off to the side Dean’s eyes widened at the show. Charlie’s hands came up to grasp them, pinch the nipples, push them upward.

Jill felt another wave of orgasms growing in her. She squeezed hard with her Kegel muscles, and pressed her knees inward along Charlie’s ribcage. As the pleasure wave maxed out, she dropped onto his chest, and switched to grinding herself on him. For both of them this was the ultimate sensation.

He grabbed her ass and pulled her tight against himself, even as she lost all control in the moment of her “little death.” His cock pumped and pulsed, pouring his essence into her center.

Then there was stillness.

When Jill roused herself she saw that Dean had set up another round of tequila shots. She clambered from the bed, followed by Charlie. Jill luxuriated in the squishy, stretched feeling at her core, the damp stickiness of her thighs. In a happy, playful mood, she took the shot glass, ignored the salt, instead bending to suck Charlie’s cum-coated cock clean before shooting the tequila and sucking on the lime.

Charlie, in the grasp of a passion he didn’t understand, but was driven to explore, took a lime slice and squeezed the juice onto one of Jill’s nipples. He dropped to his knees before her and licked her slit and clit, gathering a tongue load of salty goo. Then he shot the tequila and licked the nipple.

Jill was thrilled. These two young men were her finest finds ever. Some of her previous hotel threesomes had been on their way downhill by this point in the proceedings. This one, already orgasmically rewarding, seemed to be picking up steam and heading into uncharted territory.

Dean stared at Charlie, mouth agape.

Charlie said, “That’s so fucking hot! Dean, I don’t fucking care what you think. I don’t understand it, but I’m already getting hard again.”

Dean didn’t reply to Charlie, instead he whispered in Jill’s ear. She giggled and obliged him by turning, bending forward and tilting her big apple ass upward. Dean licked the salt, shot the tequila, then squeezed the lime onto Jill’s asscrack and lapped it off her asshole as it ran down. Now it was his turn to speak defiantly to Charlie, “You do your thing, brother. I’ll do mine. As long as Jill likes it and we like it, it’s all good.” He buried his face back in Jill’s ass, tonguing her crinkled hole obsessively.

“Damn, boy!” Jill exclaimed. “That’s so sweet! Tongue my backdoor! Wet it and spread it. I want your cock there soon.”

Now it was Charlie’s turn to whisper in her ear. Again, she complied. In a moment, Charlie lay on his back on the bed, Jill climbed atop him in a 69 position. Plunking her greasy pussy onto his face, she looked over her shoulder at Dean. “Tongue me some more, lover.”

He dove in.

Charlie lapped at her sopping snatch. Dean poked his tongue at her asshole. Jill held Charlie’s thick fuckstick in one hand and rubbed it on her face, then took the bulbous head into her mouth. She licked at the meatus and swirled her tongue over the frenulum. Soon, as she rose toward another climax, all she could do was hold the very tip between her lips as she panted in ecstasy. Again she shuddered and gasped. Globs of congealed cum slid down the walls of her pussy and into Charlie’s waiting mouth as he tongue-slapped her clit.

Soon it was too much for her to take. Pulling her mouth of Charlie’s cock, she asked him to stop licking, but please stay right there, and then begged Dean to put his shaft into her ass.

Dean drooled saliva onto her wet and relaxed anal ring, spit more into his hand and rubbed it on his cock head, and poised the head against her tiny hole.

Jill, long-experienced in anal penetration, was readily able to relax the muscle ring. Charlie from below, and Dean above, watched in fascination as Jill’s asshole opened to swallow Dean’s slender shaft. Gently, but smoothly and steadily, they worked together to ease the intruder to its full depth.

Dean, thrilled by the tight squeeze of the rectal sphincter and the furnace-like heat inside, began to aggressively hump Jill’s butt. He grabbed her meaty asscheeks in both hands and clutched them, working to spread and squeeze them as he hammered his cock into her.

Jill was driven forward and pulled back, her pussy sliding across Charlie’s face, smearing it with commingled love juice.

Charlie was in his own unfamiliar heaven, offering his face as a love-toy, seeing up close the penetration of Jill’s ass, and feeling Dean’s ball sack slap against his head with every stroke. He also put his hands onto Jill’s ass to pull her tightly down onto his face.

Jill’s senses were overloaded with pleasure, her mind also taken to unfamiliar levels of depravity. She couldn’t think to do anything for Charlie’s cock, but simply rested her face against it, and let all her muscles relax.

Dean brayed his ecstasy to the ceiling and shot throbbing ropes of cum deep inside Jill’s bowels.

Jill’s anal orgasm was an out-of-body experience unlike she’d ever had. Fluid gushed from her to flood Charlie’s welcoming mouth. She fell inert atop him.

Eventually Dean’s shriveling dick slid from her shit-chute, which gaped, winked, and closed, oozing jizz. Jill rolled off Charlie. His face was red with exertion and shiny with ejaculations. His cock stood strong at attention.