Windy City Conference

It looked as though it was just another one of the many necessary, but forgettable, business trips Charles had to endure as part of his position at an energy equipment engineering company.

This time, it was a 3-day energy symposium to be based at a large hotel in downtown Chicago. Charles had grown up years ago in the Windy City, although living now on the West Coast, but he remembered well the ordeal that flying into O'Hare during changeable weather afternoons in late Fall could be. He wasn't disappointed…his 767 flight from Seattle had to hold for traffic delays, then hold for gusty winds, landing almost an hour and a half late under a brooding gray sky. A long limo ride downtown in rush hour traffic at last delivered him to the hotel.

Tired and irritated, he checked in, went up to his suite and decided he'd take a long hot shower and unwind from his travels. The lights of North Michigan Avenue and the nearby Hancock Building were twinkling outside his room window as he dressed in slacks and a turtleneck and decided a drink in the dark old walnut-paneled hotel bar would be a very good thing to improve his perspective on the world.

As soon as he was seated in the soft leather chair of the bar near the fireplace, he saw her, instantly.

She was also seated alone in a leather chair about 20 feet away. Her presence and demeanor clearly stated a powerful business elegance, and that "look" that people who travel extensively for business seem to get, impossible to define but totally recognizable to another road warrior. Wearing a tailored gray wool business skirt, a navy blue silk blouse, and expensive flats, she was looking into the fireplace while sipping her glass of wine. This was not a hotel bar pickup sort of woman. She was a phenomenon…her hair, her eyes, the shape of her legs. Charles sipped his wine and sighed, but he also found himself glancing at her frequently and he thought, surreptitiously. She seemed lost in her own thoughts with the fireplace and took no notice of him at all. Or so he thought.

After a long travel day Charles decided he'd better get some dinner despite still running on West Coast time…it was two hours later here and he had a 7:30 am sign-in for the energy symposium the following morning…the start of a long day of panel discussions, presentations, yada yada yada. So he wandered into the most upscale of the hotel's restaurants, told the maitre'd he was dining alone, and was seated off at one of the tables in the back corner that are usually the fate of lone diners in a hotel restaurant. As he finished his crabmeat cocktail appetizer, he noticed the maitre'd seating a woman alone at the next ‘dinner for one' table over from his. It was her again.

Charles didn't know that the woman, whose name he would later learn was Margaret, had in fact been very aware of Charles's scrutiny in the bar, and had slipped the maitre'd a "little something" to be seated for dinner near him. She wasn't at all sure why, as the last thing she EVER did on these damn business trips that filled her year was to latch onto ‘encounters of chance' with anyone. That just wasn't her style. So why, she wondered to herself as she placed her dinner order with the waiter, did she find herself now seated next to this strange man on purpose, glancing at him over the leather-clad menu.

It had to happen sooner or later… Charles and Margaret, exactly at the same moment, glanced up from their dinners and made eye contact. It was very brief, but one of those locking of eyes things that seem to convey in a second or two many things that are powerful, and promising, and as old as time. They both quickly glanced back at their dinners, but they were affected and changed by just that quick communication of their eyes. They both had held the glance a little too long to be just casually taking note of their surroundings.

They both finished their dinners and left the restaurant, but a few minutes apart. Charles looked at his watch and it was getting on toward 9pm with an early day looming, but he decided to return to the bar again for a nightcap….perhaps an afterdinner brandy would be a good thing before he headed back to the suite. He rarely got involved with women on business trips, having survived a divorce a couple of years ago and since then mostly immersing in his career.

Although Charles always found hotels rather erotic places for the opportunities that they offered for meeting, wining, dining, and bedding willing females, he had resigned himself that this was just to be another night alone in a hotel king bed before meetings that only somewhat interested him. Settling himself back into one of the bar's leather chairs, this time at a table with two chairs, he enjoyed the fragrance of his Benedictine brandy and sighed to himself.

At that moment, he heard a woman's voice just behind his chair say, "That brandy looks like a perfect idea. Would you like to enjoy it with someone?" Oh my God. It was her.

As she seated herself with a crossing of her stockinged long legs and her brandy was placed in front of her, she said, "We were spending so much time glancing at each other all evening that it seemed foolish not to at least introduce ourselves. Are you also here for the energy conference?". That was the start of a casual conversation over a first, then a second brandy, of shared business interests, ‘who do you knows', and a bit of their personal lives in that intimacy of travelers that sometimes discloses things on ‘fast-forward'. They learned they were both unattached, both had traveled internationally, and both had various, well, unsatisfactory romantic histories. She had been a trader and investment banker in the past, he'd held various management jobs at the director or VP level. Although she was very sexual, and loved to fuck with all her heart and imagination, a series of bad situations had been the summary of her sex life for quite a few years now.

Margaret's long legs looked delicious encased in their expensive stockings as she casually crossed and recrossed them while they chatted easily together. Her expensive wool skirt shaped her womanly hips in a way that only tailoring can achieve. Her blue silk blouse shimmered in the bar's firelight. Very ample firm breasts were contained within, and their slight movements and the buttons of her nipples against the silk suggested to Charles she had foregone a bra as she'd dressed for the evening.

She also was not unaware of Charles's large hands, powerful shoulders, athletic legs, and the way his expensive but casual clothing rode his frame. She was further very aware of his glances at her breasts, and she also had caught him several times glancing at her legs as she shifted and re-crossed them. She felt stirrings from the attentions and the conversation she was thoroughly enjoying with this man in a hotel so far away from home. More than stirrings….she knew that her thong panties inside her snug skirt were becoming damp, and she was surprised to feel her nipples begin to harden against the prison of her slinky silk blouse. She couldn't help but notice that there was a large interesting bulge in Charles's pants as he had turned his chair a bit to face her. She wondered if he could tell, although there had been no sex talk at all, that she was becoming quite sexually aroused.

They finished their second brandy, and it was now almost 11pm with the conference start looming the next morning. As they took a friendly walk together across the elegant lobby to the elevator banks, it happened. Without a word, they simultaneously turned toward each other and kissed. One brief, cool touch of their lips. That's all. A friendly little peck. Just two people who barely knew each other but had passed a pleasant evening in each other's company.

The elevator arrived, it was just the two of them at this late hour. As soon as the doors closed, like an explosion, Charles and Margaret were just all over each other. One of those open-mouthed, tongue-lashing, gasping-for-breath kisses…..his hands dropped down to tightly grasp her skirted ass and pull it against him hard—he could feel the straps of her gstring thong through her skirt; her left hand reached down to grasp his hard cock now straining against the front of his slacks as she moaned into their kissing. Her breasts were crushed against his chest, her 5'7 height was a perfect match for kissing to his 6'2 stature.

With a soft "ding" the elevator reached Charles's floor. Eyes shining with desire, hearts pounding, they wordlessly entered Charles's suite. Crushing into another amazing full-body kiss, he was able to gasp, "be with me tonight Margaret". She was able to gasp "I want you Charles".

Neither was in any mood for foreplay… not the two of them, not this night. They moved to the king bed and Charles unbuttoned Margaret's silk blouse. As soon as her braless breasts emerged, he was licking, sucking, and caressing them, biting lightly on her big erect nipples. His hand shot up her skirt, closing over the mound of her pussy, finding the thin tight thong crotch dripping wet, stretched tightly over her now very swollen and sensitive outer lips. He grasped her panties and pulled them off of her fast, a tearing sound as the little straps parted. Kneeling in front of her, his tongue snaked up into her swollen wet lips, tasting and enjoying the perfume of her most secret scent on his face.

With her silk blouse unbuttoned but not off of her, she quickly moved to the bed. Getting on all fours with her skirt pushed up above her hips and her legs spread, Margaret gasped, "Charles, I want you to fuck me. All night. I need your big cock in my hot cunt. Don't make me beg, I want to be your Dirty Girl tonight."

Dropping his pants and briefs to the floor in one urgent movement, pulling his turtleneck up and off quickly, Charles's big cock sprang out hard and precum-coated. Moving behind her upraised hips at the edge of the bed, he entered her tight hot cunt in one thrust while standing. Margaret was able to withstand only a couple of Charles's deep, fast cock thrusts before her overheated pussy contracted hard and with a scream of passion she began cumming on his cock. She didn't know it was possible to cum like that, not ever before, and as Charles kept fucking her deep and hard from behind she found herself riding a wave of cumming plateaus that she had hungered for, heard about, but never felt between her own legs.

The suite now smelled like aroused hot pussy and the scent of passion-perspiration on both of them; the sounds were of liquid thrusts into a dripping wet cunt and their mutual cries and moans and grunts of animal passion. They both caught glimpses of their copulating in the gold-rimmed wall mirror. Margaret urged Charles on with the dirty talk of lovers that is as old as time, the "fuck me with your big cock" and "I'm cumming again" announcements, again and again. The loud slapping sounds of Charles's thrusting thighs against the back of Margaret's legs were like animals mating….his big balls slapped against her swollen red cuntlips as they fucked each other's brains out with skill and experience and powerful attraction in every thrust and counterthrust of their sweat-glistening bodies together. Margaret gasped, "Use me! Fuck me! Take Me, Charles!".

With a long tightening and buildup of pressure, Charles knew he was soon to be filling this amazing woman's insatiable cunt with his first big load of hot semen. She felt him grow huge inside her sopping, spasming pussy and started to beg him to cum inside her, to give her all his cum, to fill her hungry cunt with every drop of his hot seed. With a roar of triumph, Charles felt himself spinning into the vortex of orgasm, his big cock slamming stream after stream of man-cum deep into her pussy.

It felt like the whole world was emptying out of his balls, down the long thick pipe of his cock into this woman's milking, squirting, fucked-raw core. As she felt the first strong thick ropes of his semen slamming against her cervix, Margaret's body exploded in the biggest orgasm she'd experienced yet… all she could do was scream and babble dirty words and gasp with mouth open wide for air as she took all of his spurting hot cumload deep in her clenching raw pussy.

The next two days (and nights) of the Chicago conference, at which Charles and Margaret often found themselves seated together in the hotel meeting rooms, is a story for another time. But suffice to say, despite their East/West coast distance of their residences, the two of them still maintain contact with each other as exceptional lovers that they do not choose to lose track of, and they do manage to somehow coordinate their travel schedules to allow for other erotic times in other elegant hotels.