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Three in Chicago

Category: Group Sex
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Shortly after 5 AM the sun raged through the haze over the lake and began another attack on Chicago. The humidity and temperature had both been in the low nineties all week and today didn’t look like the time for moderation.

Fred sat up in bed, swung his feet to the floor and felt with his feet for his slippers. The air conditioner had been on maximum cool all night and when he reached for the knob to turn it to Low Cool he noticed moisture had accumulated on the outside of the window pane. August in Chicago, he wasn’t surprised.

He went to the kitchen and poured a cup of freshly brewed coffee, retrieved the newspaper from just outside the backdoor and sat down at the kitchen table. He scanned the headlines and the local news section; nothing caught his interest so he set about reading the comics and started on the crossword. It was a pleasant way to start the morning; a nice way to wake up.

The phone rang. It was 5:25 AM! It could only be some drunk with the wrong number or a computer trying send junk mail by fax with the wrong number. He snatched the receiver off the cradle and barked “Hello.” Silence, though he could tell that there was someone there. “Hel-lo” he said again, letting his annoyance show in his voice.

“Hi, honey.” It was Jean. He and Jean had met through a mutual friend a few months earlier and while it was unusual for her to call him that early in the morning, he regretted his terseness.

“Hey, you’re up early.”

“Sorry to call so early, but I have to leave in a few minutes and there’s something I wanted to ask you.”

“Sure. What’s up?”

“Are you going to be free tonight? I have a friend that’s coming to town for a couple of days on business. It’s a guy that I’ve known since we were in grade school together and I was wondering if you would like to come over for dinner tonight and meet him?”

“Yeah. That would be fine.”

“Great. Can you come around 6? I think you two will like each other. His name is Frank and he works for some kind of a dot com company.”

“OK. You want me to bring anything?”

“Bring a couple of bottles of red wine. I’ve got everything else. Gotta run. See you at six.”

“OK. See you then hon.” He hung up the phone.

So who was Frank? An old boyfriend perhaps? He wondered how close Jean had been to him. Had they slept together? Does it matter?

At 4:30 Fred got home from work. He checked his email. There was a letter from Bobbie Jo, a girl he had been chatting with online for over a year. The letter had a photo attached to it, which he opened. It was a picture of a very attractive girl with short blonde curled up on a sofa. She was nude, both of her hands were at her crotch, and her arms were pressing against her breasts, pushing them together and making them very inviting. He felt a tingle between his legs. She was a very sexy looking girl and she looked very much like what he had imagined her to look like. It was a picture of Bobbie Jo’s latest love interest. But there was no time to linger over her now. He had to get ready to go to Jean’s house.

He quickly took off his clothes and got in the shower. The warm water felt good as he rubbed the soap up and down and under his arms and over his chest. He took the soap and lathered generously between his legs, around his cock, and between his cheeks, letting his finger flicker over and into his very sensitive ass. He loved for Jean to play with his ass, flicking her finger, and often her tongue, in and around it. He and Jean loved playing with each other’s ass. The more they did it the better they both liked it. He poked the tip of his finger into his ass. He liked the feeling a lot and began to flick his fingertip and then two fingers in and out. But he didn’t have time for that now. He cleaned himself carefully, quickly rinsed off the soap and got out of the shower.

He took two bottles of Merlot from a cabinet in the kitchen, walked out the back door, locked it, and headed for his car.

He and Jean had met through a mutual friend over a year ago at a birthday party. There was an instant attraction between them. She had shoulder length light brown hair, constantly sparking eyes, and a very nice figure. Quiet and soft-spoken, Jean was secretary to Ann McCardle, a senior vice president at First Chicago Credit.

Fred was an opera fan, as in fanatic. He had had a season ticket to Lyric Opera for almost twenty years, went to as many dress rehearsals as he could, and frequently saw the same production several times. Jean was not always familiar with the story of the opera so Fred would relate the gist of the story in a farcical and fanciful manner, but accurately relating the story of the opera. With “The Flying Dutchman,” for instance, he was fond of pointing out that it was a German opera about a Dutch sailor with a Norwegian crew that could put into port only once a year. Very similar to Charlie on the MTA, but while Charlie was looking for a sandwich, the Dutchman was looking for love.

Jean buzzed him into the condo building and he took the elevator to the thirty-second floor. While her condo was not a lot of square feet, the living room and bedroom faced the lake and the eastern wall was glass, so there was a feeling of great space.

Jean met him at the door, put her arm around him and gave him a kiss on the cheek, and said “Fred, I’d like for you to meet Frank.”

“Hi, how are you? Nice to see you,” said Fred, and shook Frank’s hand. Frank had short blonde hair, he was smooth shaven, and was wearing a white turtleneck and black leather pants. It was obvious that he worked out.

“I’m good. Very nice to meet you” he said as they shook hands.

“Frank and I have known each other since about the fifth grade” said Jean. “He lived about three houses away from me and we were in school together all through grade school and high school.”

Jean fixed Fred and Frank drinks and left them in the living room to get acquainted while she finished a few things in the kitchen and got the table ready for dinner.

She enjoyed having a friend or two over for dinner once in a while, but was not one for much entertaining. Ann, her boss, came over once in a while and on two or three occasions she had helped Ann entertain clients. She and Ann had become quite close through their office relationship, and they frequently went to the movies or shopping with each other.

Jean had worked for Ann for over a year before she discovered that Ann was gay.

Ann was in her early forty’s, had an MBA in finance from Northwestern, and had risen rapidly at First Chicago Credit. She was one of the youngest department heads at the bank and the only woman. She was very attractive, with short blonde hair, green eyes, and a sense of authority that said here was a woman that knew what to do and how to do it. She was brilliant not only in financial matters, but as a people manager, which was the main reason she earned a substantial six-figure income.

Late one fall afternoon Jean went into Ann’s office to pick up some reports and found her staring out the window at a grey Chicago sky. She had been crying and the tears were still welling up in her eyes. Jean asked what was wrong. Ann took a deep breath, dabbed at her eyes with a tissue, and grasped in vain for control.

Jean put her arm around Ann. Ann was not at all a weak person and Jean had never seen her so overwrought. As soon as Jean put her arm around Ann her broken heart poured out all the smoldering ache and sting. She buried her face in Jean’s breasts and sobbed uncontrollably.

Jean helped her to the sofa and sat down beside her, keeping her arm around her and holding her close. After a few moments Ann regained her composure enough to tell Jean that her lover had found someone new and was moving to New York.

Her lover? Yes, her lover. Ann told Jean that she was gay, that the woman she had fallen in love with had just dumped her, and that she hadn’t seen it coming at all, which is why she had fallen apart.

Jean was genuinely sorry for Ann because she knew that heartbreak was a very special kind of hurt. Rejection by a lover of either sex can be devastating. The two women sat on the sofa, Jean holding a very vulnerable and hurting Ann.

After a while Ann regained her composure and sat up, wiped her eyes, and squeezed Jean’s hand. “Thank you. I’m sorry to have fallen apart on you. Thank you for being here. And I would appreciate it if you would keep this between us. No one else at the bank knows about me being gay, and circumstances being what they are, I’d like to keep it that way.” Jean assured her that everything would be kept in strictest confidence.

That experience had made Jean think long and hard about her boss. Here was a very powerful and highly respected female executive of one of the ten largest banks in the country who exposed her deepest, most intimate feelings to her secretary. That confession stirred enormous respect in Jean for Ann. She had admired Ann on a professional level from the first day she started working for her; watching her make decisions involving hundreds of millions of dollars with supreme self-confidence, and that self-confidence was even more in evidence when she let Jean see her at such a sensitive, human moment.

“Dinner’s ready” called Jean. Fred and Frank joined her at the table for roast beef, twice-baked potatoes, broccoli, and freshly baked bread.

After dinner the three took their glasses and the remainder of the wine and settled in the living room. Chopin Nocturnes played softly while the three sipped their wine and admired the view from the thirty-second floor in air-conditioned comfort. It was a clear night and there were a lot of people on the beach and in the park because of the heat.

Jean snuggled up next to Fred on the sofa. Frank sat in an easy chair with his feet stretched out in front of him. She put her head on Fred’s shoulder and gently ran her hand over his chest, letting her fingers ripple across his nipples. He kissed her head, nuzzling his nose in her hair. Jean turned her head and shifted her body so that she could kiss Fred full on the mouth and press her body against his. She took his head in her hands and kissed him repeatedly while running her hands over his body. Fred put his arms around her and ran his hands up and down her back. Her noticed that she was not wearing a bra or panties under her knit dress.

She stood up, moved over to Frank, put her arm around his neck and said, “I don’t want you to feel left out” and pulled him over to the couch, placing herself between the two men. She kissed Frank on his mouth and at the same time ran her hand down Fred’s chest to his crotch where she began to massage his cock. She could feel his excitement mount, as evidenced by the bulge between his legs, as well as her own. These were two very handsome men, as she was abundantly aware.

When Fred was in high school his roommate, Ernie asked him if he had ever had sex with another guy. By the time he had gotten to high school Fred was very much aware of the fact that he loved sex and the intense feelings it generated, but he had no experience except when he was alone. He liked looking at his cock when it was erect. He liked gripping it tightly with his hand. He liked to masturbate, and loved the feeling of breathlessness that engulfed him immediately after he came. He liked watching his cum shoot out of his cock and if he were lying down he would shoot over his tummy. Most of the time when he came he came in his hand and licked and sucked it into his mouth. He had grown to like the taste and feel of his own cum. But he had never done anything with another guy.

When Ernie brought up the subject of sex with another guy Fred was at first astonished. It was only after several minutes of conversation that he finally realized that Ernie was really sincere about having sex, that he was admitting that he, too, liked sex. At that point Fred began to realize that this was a sincere invitation to something he already knew he was eager to try. He was afraid to admit too readily how very eager he was to try sex with another guy, but Ernie made it so easy, and definitely inviting.

One night, as he was taking his clothes off and getting ready for bed, Fred turned to see Ernie standing next to him, nude. Fred smiled, quickly stepped out of his underpants and looked intently at Ernie. The two simply looked at each other’s cocks for a few moments, then Ernie took Fred’s cock in his hand, and gently squeezed it. In the next instance they were caressing each other and feeling each other get hard.

Ernie made the first move. He knelt down, began to lick the head of Fred’s now erect penis, then taking the head in his mouth and sliding up and down the shaft. Fred’s heart began to beat rapidly from the excitement. Nobody had ever done this to him before. He was almost overwhelmed by the wonderful sensations streaking through him. Ernie held his lips tightly around Fred’s cock and began moving his head faster and faster and taking the cock deeper and deeper down his throat. He grasped the base with his hand and began to jack Fred off while he sucked his cock, twisting his hand as he moved his mouth up and down the shaft. With his other hand he began to gently pull on Fred’s balls. In practically no time Fred was on the verge of cumming, and had an overwhelming desire to do exactly the same thing to Ernie. He could feel his cum welling up inside when he pulled his cock out of Ernie’s mouth and helped him stand up.

By now, Ernie was sporting a very hard, very inviting cock. Fred wasted no time at all kneeling down and taking it without hesitation into his mouth. Feeling a cock in his mouth for the first time was sensational. He put his arms around Ernie and little by little took his cock deeper and deeper in his mouth. It was a fairly thick cock, thicker than his own, but not so long that so he couldn’t take it completely in his mouth and throat without any problem. When he went down as far as he could, with the cock completely in his mouth, he could feel Ernie’s pubic hair brushing against his upper lip. Fred was struck by how much he enjoyed these new feelings. How very erotic they were and how tingly they made him feel. He could feel his own cock throbbing and his ass contracting each time he took the cock deep in his mouth. Copious amounts of saliva were lubricating each thrust and in no time at all Fred developed a rhythm that was obviously bringing Ernie to a peak of ecstasy. Fred was pulling on Ernie’s balls while he had his hand wrapped around the shaft and at the same time taking him as deep into his mouth as he could. He pulled on Ernie’s balls, gently at first, then with stronger force, when he noticed that each time he did so Ernie gasped and moaned with obvious pleasure. Faster and faster and deeper and deeper holding his lips firmly around this great cock he had in his mouth.

Then Ernie gasped and gently touched Fred’s head with his hand. “I’m going to cum!” Fred pulled his head back so that he could have his hand around the shaft and only the tip of Ernie’s cock was in his mouth. He felt the first spasm with his hand, then a warm stream of cum filled his mouth. The force was astonishing. It was like nothing he had ever felt before. All of these wonderful sensations were merging together in one magnificent moment. Fred was quite taken aback with how hard Ernie had shot in his mouth and he was also surprised at the amount. He had to swallow two or three times in quick succession to keep up with the flow. The taste was so mild and the texture enhanced the eroticism of the moment. He could feel his own cock throbbing as Ernie filled his mouth with cum. When the orgasm finally subsided he milked Ernie’s cock with his hand, licking the last drop of cum off the tip and giving his balls one last tug. He looked up at a smiling Ernie. Fred stood up and all he could manage to say was “God, that was great!” Ernie smiled at him and said, “Now it’s my turn” and knelt down and took Fred’s hard cock in his mouth.

He started sucking, taking it deep in his throat in long, steady movements, and turning his head slightly as he went down on it. He put one arm around Fred and pulled his body toward his face as he took Fred’s cock deep in his throat. He grasped Fred’s balls and began to pull. Fred was so turned on from having Ernie shoot in his mouth that it was only a few short moments before he was at the very brink of orgasm, straining to make it last as long as possible. Then Ernie let his fingers slip between Fred’s cheeks and gently poked a fingertip into his ass. This produced an electric sensation that Fred could no longer resist and he shot into Ernie’s mouth with intensity never felt before. He was almost overcome with the sudden rush of rapture and Ernie milked every last drop of cum out of his cock using his lips then flicking his tongue over the tip collecting every last drop.

Jean rubbed Fred’s crotch harder and faster and when she felt his erection grow she turned and began to undo his belt. While working on Fred’s belt she put her hand between Frank’s legs and discovered that he was already hard. He helped her unbuckle his belt and unbutton his tight leather pants. He was not wearing any underwear and a very large erection popped out as soon as the pants began to come down. Jean smiled and turned to look at Fred. Fred’s eyes were riveted on Frank’s cock.

Now that the ice had been broken both men stood up and quickly got out of their clothes. Jean stood between them and with a cock in each hand kissed first one then the other. She was kissing Frank as Fred began to lift her dress over her head and she while her arms were raised Frank cupped her breasts and began to run his tongue over her nipples. After pulling her dress off Fred knelt behind her and caressed her hips and began kissing her buttocks. He held her hips and slowly began to run his tongue down the crevice between her cheeks. Frank then knelt in front of her. Jean was smooth shaven, which aroused fiery passion in Frank as he knelt before her and began to explore between her legs with his fingers and tongue. At almost the same instance Fred parted her cheeks and let the tip of his tongue touch her ass while Frank spread her labia and the tip of his tongue found her clit. Jean felt a wave of arousal course over her and felt herself getting very wet. She cupped her breasts, began to pinch her nipples, and threw her head back reveling in the exquisite passion engulfing her. Fred’s tongue was probing her ass and Frank was sucking on her clit and slowly moving first one, then two fingers into her pussy. She moved one foot a step sideways, spreading her legs and making herself more available to the two men.

The sensations generated by the two men had her on the brink of orgasm almost immediately. She began to squirm as Fred thrust his tongue into her ass as forcefully as he could. His mouth was brimming with saliva and as he used his thumbs to spread her cheeks he let the tips inch closer and closer to her ass. Her ass was well lubricated by now and little by little Fred worked just the tips of his thumbs into her anal opening all the while probing her ass with his tongue.

Frank was licking, then sucking on her clit while moving his fingers in and out of her pussy. She could feel her wetness spreading as he pressed his mouth against her. As Fred probed harder with his thumbs she began to swivel her hips, pressing against his thumbs and letting them incrementally enter her then thrusting forward to meet Frank’s mouth and hand.

Her nipples were firm and erect and she cupped her breasts, pressing them together as she pulled her nipples inward. She felt herself beginning to cum. She bent her body forward, pressing her ass onto Fred’s tongue and her pussy onto Frank’s lips. Her legs began to tremble as waves of ecstasy rolled over her. Both men could feel her passion spreading through her body and entering their own, increasing their fervor and excitement.

By now Fred had both of his thumbs in her ass and was able to get his tongue deep inside. He pressed hard against her bringing her to one exquisite climax after another. He stood up and while still keeping his thumbs in her ass let his very hard cock rub against her opening. He took his thumbs out, grasped his cock in one hand and put his arm around Jean’s waist and slowly began to press his cock into her ass.

When Jean felt Fred’s cock press against her ass she inhaled sharply as a surge of anticipation flooded her. She felt the head of his cock pressing harder and harder against her ass, fighting her resistance. Then, as if surrendering, she felt herself open up and his cock plunge inside. His cock slipping inside her triggered another orgasm. He grabbed her hips and thrust himself forward, maximizing his penetration. She stood erect now, and in doing so clasped her ass tightly around his cock. He cupped her breasts, feeling her erect nipples. Fred was seven or eight inches taller than Jean and it seemed that if he were to stand fully erect he could support her entire weight with his cock. She wiggled her ass slightly as though to get even more of his cock inside her. He moved one hand from her breast and ran it down her body, across her smooth skin, caressing her as he continued to thrust his cock into her ass.

Frank stood up and began to stroke his cock. Seeing Jean impaled on Fred’s cock was exciting him immensely. He went to her, and holding his cock in his hand began to rub her pussy with his cock. She was so wet that his cock was glistening after only one or two brushes against her.

Fred, holding her completely off the ground, slowly walked backward until he could sit on the couch, his cock still deep in Jean’s ass. As they settled onto the couch Frank followed, knelt down, spread her legs and once again began to lick her pussy and clit. Now, while he ran his tongue over her clit he let his fingers slip around Fred’s balls and little by little began to gently massage them as he pressed his mouth against Jean. Fred could sense the intense pleasure Jean was getting from Frank, and when he felt Frank’s hand on his balls he began to thrust with even greater vigor.

Frank wanted to do more. He moved his hand under Jean’s leg, then Fred’s leg, spreading them wider apart. Fred could sense what Frank wanted and put his leg up on the couch, swiveling his rear so that he was lying on the couch his cock still firmly lodged in Jean’s ass, their legs spread wide apart. Frank then moved on top of them, and lowered himself, getting his cock next to Jean’s pussy. She reached down and guided it inside her. Fred immediately felt Frank’s substantial cock pressing against his own cock as it entered Jean. With both cocks in her body, Jean put her arms around Frank’s butt and pulled him hard into her, their closeness bringing yet another orgasm.

Frank began to fuck her faster and faster. She held him as close to her as she possibly could, he hands at first cupping his cheeks, then spreading them, then her finger tip finding his asshole. Jean was so wet that moisture had spread almost everywhere and she lubricated Frank’s ass with her own wetness. Once she had the tip of her finger in his ass she simply held her hand and let Frank’s backward thrust drive his ass around her finger. After a few short moments she had her finger into his ass up to her second knuckle. He began to moan with pleasure and the sensation of her finger in his ass made him thrust his cock into her harder and harder.

The increased fervor with which he was fucking her drove Fred to the very brink of cumming. He felt Frank’s every move, each orgasm Jean had caused her ass and pussy muscles to contract heightening the sensations for everybody. His breath began to come in short gasps, he clutched her tighter and tighter, and buried his face in her neck. He could feel her firm breasts and nipples pressing against his chest. He felt a great welling up inside and Frank’s rapid thrusting put him over the edge. He felt the spasm building then his entire body went rigid as he shot an explosive stream of cum into Jean’s ass. Frank knew immediately that Fred was cumming and it triggered his convulsive climax. Fred could feel Frank’s cock throb with each spurt of cum. The synergy had been so overwhelming for all three they lay motionless, completely drained, and breathless.

It was several minutes before anyone was able to move. They each lay perfectly still, savoring each final ebbing contraction and slowly getting their breath back. Jean could feel their cocks growing soft inside her. Their bodies were slick with sweat. Frank, being on top, got up first. When he pulled his now limp cock out Jean felt his cum began to leak across her inner leg. She put her hand between her legs and as more and more of Frank’s cum oozed from her pussy she smeared it over her legs and tummy.

She grasped the back of the couch and pulled herself to a sitting position. Fred’s cock, though completely limp, was still in her ass. Frank held out his hand to her to help her up. She slowly pulled herself away from Fred, feeling his cock slip out of her ass as she rose.

The three smiled broadly. It had been a rather exciting evening so far, and, as the saying goes, the night was still young.

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