Flying The Friendly Skies

"I've never come like that," she said lazily, looking at him through half-closed eyes. "Can we do it again?"

Tim eased up beside her and slid his arm under her shoulders. "Yes, but we have something else to do first," he said, as he rolled onto his back and pulled her along until she was lying on his stomach.

She could feel his cock between them and asked, "What is your servant to do now Master?"

"I want you to get up here and let me love your tits," he answered, pulling her upward until her breasts were swaying in his face. Holding them together, Tim was able to suck both nipples at the same time, almost driving Cheryl over the edge again. He could feel her cunt leaking moisture onto his stomach and slid her back until the head of his cock was at the entrance to her pussy.

She wanted to slide further back, but he held her in place. "Just take your time," he advised. She let her breasts dangle in his face and he took the opportunity to massage each breast and nipple.

"Oh, they're so sensitive when they hang like that. I could let you do that all night," she cooed, as Tim continued rubbing her tits. "But, we have other matters to attend to, don't we?" she said, as she got to her knees and moved back until her she could grasp his shaft. In one smooth, graceful movement, she squatted, held his dick erect, and slid the head and an inch of the shaft into her molten cunt. After lazily moving up and down for a few strokes, she declared herself ready.

"OK, Master. My pussy is so wet and hot, and your cock is so hard, I am ready to get fucked," she said, sliding down the entire length of Tim's eight-inch cock in one move. Her eyes flew open as she realized she had it all inside her. Her breath became ragged, and she started coming almost immediately. Tim knew that this was just the beginning, and held himself still, giving her all the time she needed.

When her spasms subsided, she looked into his eyes and said, "Well, now that we've gotten that minigasm out of the way, let's work on a majorgasm!" She began moving up and down slowly, clenching her pussy walls and making sure that Tim was getting just as much pleasure as she was. She fucked him for a few more strokes, then sat down and ground her cunt onto his cock. Her angle put his cockhead on her g-spot as she moved forward, and she began to climb that mountain of orgasmic bliss again, this time taking Tim with her. As they neared the peak together, Cheryl began humping violently, her hair flying around her head, her titties jiggling, and her pussy on fire.

Tim couldn't take any more and shot the first string of cum deep into her hot, writhing pussy. When he did, she screamed at the top of her lungs, "Oh, God, I'm cumming too!" and began to hump almost uncontrollably. Tim grabbed her hips and held her in place while he emptied his balls into the hottest pussy he had ever fucked. When Cheryl stopped squirming, he held his dick inside her, allowing both of them to bask in the afterglow. He was not soft at all, a point she noted when she said, "Damn, I'm exhausted, but you're still hard enough to fuck again. How do you do it?"

"You're one of the sexiest women I ever had the pleasure of making love to. Your beauty, your body, your attitude, your hot pussy-all make you unbelievable woman, and I want you to know I appreciate you. I could fuck you again right now, but since we have another couple of days, let's not wear ourselves out. We have plenty of time to fuck each others' brains out," he said tenderly.

Cheryl, brought to tears, crawled off his body and lay beside him, molding herself to his side. As he cradled her in his arms, she sobbed gently, and soon they drifted of into the sleep that sated lovers know so well.

Tuesday

The next morning found Tim refreshed and in the company of two executives from a much larger branch than his. One of them was a fifty-something stout man, while the other was an extremely attractive woman, looking to be in her mid- to late thirties. She made it obvious that she was on the prowl, even slipping Tim her cell number just before a break.

Tim's phone vibrated and the message read, "Shopping again! More surprises in store! Lol" His coworker, gave him a knowing eye, and they went back to work. The morning flew by, and at lunch, Tim got another message, this one saying, "Open discretely." Again going into the bathroom, he opened the file and was again amazed. All he saw was Cheryl's hips and the backs of her thighs, except for a buttplug in her asshole, and a long, flesh-colored dildo being pulled out of her pussy. It glistened in the light, as if it were wet with her juices. The caption said, "Practicing for tonight."

Naturally, Tim had trouble concentrating on business the rest of the afternoon, and when they wrapped up for the day, he wasted no time getting to his room. Cheryl was waiting for him by the window, wrapped in one of the hotel's terry robes. When he came into the room, she turned to face him and opened the robe. Her body was partially hidden in the shadow, but he could still see it was fantastic. He felt his cock begin to rise as she shed the robe and walked slowly towards him.

"I hope your meeting was productive," she said as she slipped into his arms and their lips met. Cheryl knew just how to get Tim's engine revving and she started with fervor. Her tongue was in Tim's mouth before he realized it, her breasts were mashed against his chest, and her hips were grinding into his groin.

Tim held her closely and let his hands wander over her exquisite body, eventually sliding down her back to cup the globes of her full ass. Tim knew he had never felt such a perfectly shaped, resilient ass. Just thinking about it, along with Cheryl's tongue and breasts, gave him a raging hardon very quickly.

Breaking their kiss, Cheryl said breathlessly, "Let's get you out of those clothes and into something a whole lot softer and sexier." She knelt and began untying his shoelaces while he took off his tie. Soon they were down to his briefs, with his erect cock straining against the elastic at the waist. His cock was at eye level and she said, "Ooh, it's even bigger today! I don't know if I can handle that monster!"

Tim laughed softly and said, "My dear, you can handle it. You just need to take your time and let it happen." He chuckled softly and stood her up, drawing her to his body for another passionate kiss. She reached between their bodies and caressed his cock, finally sliding her hand under the waistband and freeing the shaft. Smearing the drop of precum with her thumb, she said, "Let's get these off and eat our dinner. I think you'll need all your energy tonight."

She stepped back and knelt, taking Tim's briefs with her. Sliding them down his legs, she realized how muscular he was. Looking upwards, she saw his balls were tight in their sac, his abdomen was toned, and his chest was extremely well developed. "Damn, Tim. I didn't realize you were in such great shape. That makes you even sexier!" she said, arising and taking his hand, leading him to some pillows on the floor, near the coffee table.

"I hope you like steak," she said, as she took the top off a hotel serving plate.

"Love it," said Tim, as he stretched out on the pillow, Cheryl kneeling beside him.

She cut a piece of the filet mignon and fed it to him, then taking a small bite herself. They shared a glass of wine, and she continued to feed her lover. Meanwhile, Tim found a use for his hands. Each time Cheryl would lean in, he massaged a swaying breast or caressed her thigh, causing a slow buildup of heat that he knew would soon erupt.

Finally finishing their meal, she picked up the tray and carried it to the door, setting it in the hall. Rick took in her swaying ass as she walked to the door. She opened it, stepped out in the hall and set the tray down, never looking to see if anyone may have been watching. Tim told her, "You know for someone who's limited as far as sex goes, you sure are brave."

"What on earth are you talking about?" she asked innocently. "Well, for starters, you agreed to spend the night with a man you met on the plane that brought you here; then you sent him very sexy messages and fucked him silly; and now, you just sashayed to the hotel door naked, opened it and stepped into the hall without looking," said Tim, pulling her down so that she lay at an angle across his body. He could rub her ass and she could stroke his cock.

"Look, after my husband and I split up, I almost went crazy with desire. I found a lover who tutored me and brought me to his point. That's the help I keep referring to," she said, as she turned and took his cock in her mouth. She held the head in her lips and licked a drop of precum from the slit, then tickled his shaft with her tongue. Taking it out of her mouth, she looked at him impishly and said, "Enough talk. Let's fuck."

She threw her thigh over his hips and positioned herself so that her dripping pussy was directly over his cockhead. Holding it in her hands, she guided it into her channel, sliding down its eight-inch length slowly, enjoying each inch. When she reached bottom, the head was pushing against her cervix. Her eyes flew open and she exclaimed, "You've gone where no man has gone before, and if my ass has its way, you'll do it again before the night is over!"

With that, she simply ground her hips into his groin, causing here cunt walls to contact every centimeter of his throbbing cock. Moving in a lazy circular motion, she moved his hands to her breasts, urging him to pinch her nipples, which he did with pleasure. Her breasts seemed even more aroused than they had been the previous night. Tim massaged them, rubbed them gently, rolled the nipples between his thumbs and fingers, and finally sucked them.

The attention to her titties served only to stimulate Cheryl's body even more. She had ceased to grind and begun fucking like there was no tomorrow. Her hips were in constant motion, her titties jiggled, and her mouth hung open. Every breath brought a groan of pleasure, and through her pleasure, she could feel Tim getting close. He had grabbed her hips and was pistoning his cock in and out of her wet cunt. He held her in place and shot a spurt of cum deep into her pussy, followed by two more.

As if in a daze, Cheryl placed her hands on his chest and screamed at the top of her lungs, coming right along with him. She collapsed onto his chest, sobbing quietly, and planting tiny kisses all over his chest, neck, and finally his lips. The kiss turned hot quickly and Cheryl was delighted to feel Tim's still-erect cock throbbing in her dripping cunt.

"That was great!" she murmured, as she began to rub her clit up and down his cock. "But I have a special favor."

"What's that?" asked Tim, feeling his dick getting harder.

"I want you to fuck me in the ass," said Cheryl, pushing herself upright and grinding down on his cock again. "I know that's a lot to ask, but I want to give you something special for all the pleasure you've given me. I've never had a real cock in my ass, and I want the first to be yours."

Tim was overwhelmed and reached up to embrace her and roll her to his side. Looking deeply into her eyes, he could sense her sincerity. The feeling he got touched him and he said, "First of all, Thank you. Believe me; I've received just as much pleasure from you as you have from me. For you to choose me to share this added pleasure with you absolutely blows my mind. You are such a beautiful, young, and sexy woman; I don't understand what you see in an old geezer like me."

Cheryl punched him in the arm playfully. "Old geezer my ass! How does sexy and experienced fucker sound?"

"Well, whatever we choose to name it, I think we make love beautifully, and I know I enjoy it immensely," said Tim, as he took pressed his lips to hers, making the kiss last without using his tongue. Sliding a hand down her side to her hip, he cupped her ass and massaged it sensually.

"You know I'll be gentle and let you set the pace, but don't you think we might need some lube?" Tim asked, as he began to probe nearer her crack.

"Got it covered," she said as she hopped off the bed and ran into the bathroom, coming back with a partially used tube of lube. Tim looked at her with a question in his eyes, and she said, "Yes, it's been used. How do you think I got the buttplug in there today?"

Crawling onto the bed, Cheryl reached between her legs where the cum was leaking. She took the first dollop and slipped it in her mouth, making a show of licking all of it off her finger. She then collected another scoop and made a show of rubbing it in her asshole.

"Well, are you just going to lie there, or fuck me?" she asked.

Tim's cock swung menacingly as he rolled off the bed and pulled Cheryl to the edge. Taking the lube, he applied some to her cum-soaked asshole, as well as his cock. Taking a few seconds to stroke his cock, as well as Cheryl's ass, he then rubbed the head up and down her cunt, adding more lube. He told her, "This is going to be a very special time for both of us. Right now, all I want to do is ram my cock in your ass to the hilt, but I know you're not ready. I'll go as slow or fast as you want, provided I can stand it. Damn, you are one sexy woman!"

Cheryl reached behind her and pulled her asscheeks apart. "I want it just as bad as you, but we need to start slow. Put the head up to my rim and rub it around," she said, her body quivering with anticipation.

Tim did as she asked, and applied gentle pressure to her anus. Surprisingly, the head slipped in quite easily. "Oh, God! I hope the rest is that easy. Goddamn Tim that feels good!" she said, pushing back and urging him deeper.

Tim's cock stretched her asshole, but encountered little resistance. The friction created intense feelings along his cock. He proceeded gently and with Cheryl's help, he soon had half his cock buried in her ass. Stopping, he took in the scene and was overwhelmed by the eroticism. Cheryl's shoulders and back tapered to a delectable waist; her tanned hips were just the right size for grabbing and ramming a cock into her pussy or ass; their flesh inviting a playful slap, and that's just what Tim did, loving the resulting jiggle of flesh.

Cheryl squealed and pushed back against his cock, burying more of it in her ass. He smacked her asscheek again, and she slid further back onto his cock. "Oh, Tim! Slap my ass again! Nobody's ever spanked me before. It's so sexy," said Cheryl as she wiggled her ass.

Tim slid his cock completely into her ass and felt the contact between her hips and his thighs. "How's that?" he asked. "You've got it all in your ass now."

"Oh, I know" said Cheryl, her breath already becoming ragged. "I think I'm ready for you to fuck me."

Tim withdrew his cock slowly and stopped, leaving only the head in her ass. Knowing that she was not ready for fast thrust, he began a slow rhythm, burying his cock to the hilt, then withdrawing it slowly. As he began to fuck faster, his balls slapped her cunt, providing another thrill for Cheryl. As they fucked faster, Tim was amazed at the ease with which Cheryl seemed to accommodate his eight-inch cock.

"I'm ready. Fuck me hard!" shouted Cheryl, burying her head in a pillow and moaning incessantly. As he increased his tempo, Tim began to spank her again. Her ass was beginning to turn red, creating even more heat. He felt the familiar churning in his balls as they slapped her pussy, and knew he was going to come soon.

She screamed at the top of her lungs. "Oh yeeesss! Fuck my ass! Spank me! Let me come on that monster cock! Oh God! I'm cumming!!" She continued to push back onto his cock, and wiggling her dick-filled asshole. Her orgasm was intense and lasted for a full minute.

Tim let her begin to slow down, then fucked her hard for a few strokes, bringing her back to the height of her climax and spurting his load of cum deep in her ass. He seemed to come for minutes, emptying a new shot of jism with each thrust. Finally spent, he slid his cock from her ass and watched the head slide out with an audible "Pop" and watched the thin stream of cum follow it out of her asshole.

They collapsed on the bed, and just before drifting off to sleep, Tim felt Cheryl curl up in his arms.

Wednesday

Tim was paired with the same guys as he had been on Monday, but he noticed a subtle change. When they had completed their assignment, each of the other guys headed off to talk to one of several older attendees. When they got back together, Tim asked what was going on. They told him that this conference was a perfect opportunity to change positions, branches, or managers. Tim was completely happy in his present position and location, so he passed the information off.

At lunch, his phone buzzed. The message from Cheryl read, "Help has arrived!" and included a pic. Stepping into a nearby restroom, Rick opened the pic. There lay two perfectly shaped, full, oil-covered asses, naked as the day they were born, but certainly sexier. The picture, taken from their feet, showed two very inviting slits of paradise. Naturally intrigued, Rick felt himself getting hard, and knew he was in for another night of fun.

The lady exec from Tuesday, whose name was Susan, made eye contact several times that afternoon, but she and Tim were never able to get within speaking distance, and when the session was over, he went to his room.

When he entered, Cheryl was putting her phone away. "Syd's going to meet us for dinner at a small club downtown. She's dying to meet you!" she said, as she slid the hotel robe off her nude body. Tim pulled her to him and kissed her deeply, feeling his cock begin to rise.

Cheryl reached down and fondled his dick, but pulled away from his embrace.

"Look," she said, still holding him by the dick. "I know I've asked a lot of favors, but this one is very special to me. Syd is the 'help' I keep referring to. She had a couple of really ugly experiences with men, and she hasn't had any desire to be with one since. I told her about you, and for the first time in three years, she seems excited about meeting a man. She knows we're lovers, and doesn't feel threatened; she said that maybe you could help her get over her anxiety. I have assured her that you are sweet and compassionate, and won't pressure her into anything."

Bending down and planting a very wet kiss n the head of his now very erect cock, Cheryl looked up as she tongued his cockhead. "I don't know what to say," said Tim, as he was reveling in the sensation of her lips putting pressure on his dick's crown. "You have a very convincing way of getting me to do about anything."

"Well, let's get a shower and get dressed," she said coyly as she led the way to the bathroom. "I'll get the water hot."

Tim disrobed quickly and joined Cheryl in the steaming shower. He washed her back, paying special attention to her asscheeks and reaching around to fondle her breasts. She moaned and leaned back into his body, reaching around to stroke his cock. "We need to wait so Syd can get the full benefit of that monster," said Cheryl, as she soaped Tim's chest, stomach, and cock. "I promise you that if things don't work out with her, I'll make it up to you."

She rinsed herself and stepped out of the shower. "Come out and let's dry each other," she said, handing him a towel. The mundane task became hot as they found each others' erogenous zones with the soft towels. Again, Cheryl bid him patience, assuring him that it would be rewarded.

He started to dress casually, and Cheryl stopped him as he was putting on his underwear. "Syd and I have rules when we go out. First, no underwear of any kind; second, everybody dances-no wallflowers. Do you think you can abide by the rules?"

"Well, since I haven't seen you with underwear on since Sunday, I guess I can stand it one night. As far as dancing, I'm not very good at it," he said, as he pulled on his trousers and a polo shirt.