Chuck’s Chicago Assignment
by 1stprize
In the second month an email reached his box announcing a safety week that included luncheons every day for the staff, a chili cook-off and a big cook-out to end the week. He was personally invited to participate by the plant manager and his direct report, Brenda Collins, the value stream manager he worked for.
The first couple of days of the week, Chuck was actually too busy to participate so he sent an email each day asking forgiveness for not attending. The second day, Brenda came to the project trailer with a large plate of barbecued ribs and brisket. He was slightly embarrassed by this but accepted the food and the company of his boss gracefully.
Brenda was a slender brunette, short, about 5′-2″ with a good figure. Chuck had noticed early that she did not wear a ring, so he assumed she was not attached. She dressed fairly conservatively, but seemed always to wear tops and blouses that showed off her very nice breasts. Her slacks were never too tight. She was just an extremely attractive woman.
As they sat eating their lunch, she shared that she was a single mom with two kids, a girl 16 and a son 14. She said they were both good kids and didn’t fight or bicker like most brothers and sisters, so she felt blessed. They got good grades and the older sister always helped the younger brother with homework and projects so he would succeed. Chuck offered that she should be happy they got along so well. She smiled a pretty smile and agreed. When they finished lunch, she asked him if he was going go join them for the chili cook-off in two days. He said that he was sorry that he didn’t have a place to prepare his “world famous” recipe that would almost certainly win the competition. She laughed at his boasting and said that her kitchen could be made available for the preparation. Chuck pondered that thought and said he would get back with her. She smiled over her shoulder as she left the trailer and said “You might like what we could cook up together” That statement took his mind off the rest of that days business activities.
The next morning Chuck sent an e-mail accepting the offer of a place to blend his magic potion and Brenda responded almost immediately with her address and home phone number. She called several times that day to confirm that he indeed intended to visit her.
The evening of chili cooking was pleasant, and playful. Brenda wore much more casual and sexier clothing to work in her kitchen. Her apron was over a pair of short cut-off jeans and a halter top. He had taken liberties himself wearing walking shorts and a tee shirt that showed his well trimmed chest and abs.
Brenda started the evening off with a pretty stiff vodka martini on the rocks for him, which washed away the cares of the day. She was drinking Moscata by the tumbler full and it didn’t take long before they were both pretty mellow.
The spices were blended, meat browned and vegetables added to each of their recipes and the pots were set to simmer. Brenda suggested that they move their drinking to the “mancave” so named because she decorated it in hopes of trapping a man. Chuck laughed at that suggestion, as if she needed anything to get a man’s attention.
Brenda shared that her life as a value stream leader had its drawbacks, not the least of which was a total abandonment of any kind of social life at all. As they sat and became more and more mellow, Chuck playfully suggested ways she could enhance her opportunities. She laughed at some of his suggestions, like joining an online dating group that held group parties and such. “Hell, Chuck, I’m not that desperate”, she laughed and then looked sort of sad and added “Am I?”
Chuck had struck a nerve and would like to have crawled under the sofa, when she brightened and said, “I could always hire hot sexy project managers and seduce them while we made chili”. That brought a welcome laugh and rebuttal from Chuck. They checked on the chili and Brenda mixed more martinis. “Fuck, you’re going to get me drunk.” Chuck blurted. His face reddened and he immediately began apologizing for dropping the “F-Bomb”. Brenda snickered into her hand and answered “What…the fuck…” and then she laughed uncontrollably. “Don’t worry about it, it’s one of my favorite words, just ask my kids.” she laughed even louder. “Not only is it one of my favorite words, it is also one of my favorite activities” with that she doubled over in laughter. Chuck was still embarrassed and continued to apologize. Brenda, by now, free of all inhibitions, looked at him and offered “I’m serious, I would rather fuck than just say fuck.” Her body was convulsing in laughter at this point and Chuck loosened up and joined her in the joke. “Well we have way too many clothes on to fuck anyway.” Chuck shot back. Brenda’s face looked surprised and determined to make that statement false. “Well, fuck, then” she blurted as she ripped the apron over her head followed by the halter top. “Let’s see about that.” she concluded standing there half naked, her truly magnificent breasts jutting out from her chest proudly. While Chuck was elated he was not just a little bit worried that this game had gone too far. His contract was very lucrative and he was at risk of blowing it here.
Brenda ran her hands over her breasts and asked “Do you think my titties are too small?” Chuck’s brain had reached overload about five minutes ago. He wasn’t sure even how to answer that question, or actually whether to answer it at all. Brenda had obviously drank too much, and she was not the precise professional she was in the office at all.
Chuck handed her the halter top and told her that he thought they maybe should call it a night. Brenda expressed objections, but Chuck helped her put her halter top back on, and led her into the kitchen. He brewed a pot of coffee and sat her down for a cup. She once again objected, but he insisted and she complied under protest.
He gathered his things and told her that he was leaving.
Embarrassed, Brenda said she had a good time, but they probably shouldn’t do this again. He agreed and left, his chili still simmering on her stove.
Chapter two:
The next morning Chuck’s head was the size of a basketball, and the pounding was incessant. He showered and was at the plant a half hour early. He brewed very strong coffee and drank it quickly trying to shake the thunder from his brain. He busied himself with excel spreadsheets and project management software to try to get the image of Brenda’s gorgeous tits out of his head. “Stupid Fuck” he thought aloud, as he imagined how good it would have been to suck those amazing nipples into his mouth.
“Boy, you just don’t know when to quit, do you?” he heard Brenda’s voice behind him. His face once again reddened from embarrassment. “Oh Brenda, I’m sorry, I didn’t have any idea you were here.” He said apologetically. “Let’s not go there again, okay?” Brenda said with a half smile and a stifled chuckle. “No, let’s not” Chuck agreed.
They went to work assembling materials for a morning meeting when Chuck asked why she was there at all. “I had to bring in the chili” she said, “And I wanted to apologize for my stupid, slutty behavior last night.” She looked him in the eye to see what his reaction would be.
Chuck cleared his throat nervously and spoke, “No apologies necessary, we have all done things when drinking that we would rather have never done.” she moved to the other side of the table they were working on and continued, “No, I was not that drunk, I knew what I was doing, I had that planned all night, you just gave me the perfect opening when you dropped the f-bomb.” Chuck looked surprised and puzzled. “Weren’t you just a little curious about why my kids weren’t there? I mean you knew I had kids, I didn’t hide that, and it was a school night?” Chuck looked at her with that amazing dumb look men get when women mess with their minds. “I called my sister and told her to have the kids spend the night at her house.” I was planning to fuck your brains out, but you turned out to be a nice guy, which is exactly what I would love to have but haven’t been able to find.” Now Chuck’s embarrassment was turning into pity. He felt sorry that he had ever placed Brenda or himself in that position. She was truly beautiful and now he realized that she was also very sweet.
“Look,” he began, “Maybe we need to start all over again. Maybe we need to have a date that isn’t charged with sexual energy and fueled by alcohol. Hell, Brenda, you’re a chemical engineer for Christ’s sake, you know how volatile alcohol is.” with that they both chuckled. “Yes I do know,” she said “And I was about to burn my whole house down last night.”
Chuck put his arms around her and gave her a hug. “Can I have another chance?” he asked.
She lifted her face to his and their lips met. “Yep, stupid fuck.” and then they both laughed loudly.
The chili cook-off was an amazing success with nine entries, Chuck didn’t win, but everyone agreed that his chili was one of the best. Everyone admitted that it was more political than culinary, and each person voted for the chili made by either their direct supervisor or someone higher to make them feel good.
A quick e-mail from Brenda suggested that they do Chinese that weekend in Chinatown. Chuck agreed and told her that he would pick her up at her place early Saturday evening. They were like two college freshmen anticipating their date.
Chapter three:
When Chuck pulled up into the drive at Brenda’s home he noticed what a nice home it was. Two story, probably three or four bedrooms, the kitchen was very nice with all the modern amenities, he liked the “mancave” and was impressed that there was a three car garage. Brenda answered on the dong of the ding-dong of the doorbell. “Eager, are we?” Chuck joked. “Shut up and kiss me.” She said “Come here, I want you to meet my babies”
Standing at the kitchen counter was a beautiful girl with long dishwater blond hair that fell freely off her shoulders down to just above a perfectly sculpted ass. Her legs were long and wonderfully muscled as if she participated in running or swimming sports. Her face was breathtaking. She looked up from her snack and smiled sweetly as her mother introduced her. She wasn’t a clone of her Mom, but a smaller version with refinements. Chuck was taken by her. A young man with broad shoulders that paid evidence that he worked out and lifted free weights appeared in the door between the kitchen and the mancave. “And these are my pride and joy. “This is Briana, and this is Cary.” Chuck extended his hand to Cary who shook it with authority, and Briana nodded smiling a pretty smile.
“I am depending on you to being on your best behavior.” she admonished. “Have we ever given you reason to worry?” Briana offered, and with that Brenda kissed both of them on the lips and they were off.
On the ride downtown to the dim sum restaurant Chuck had selected off the internet they talked about Chicago, and the reputation of corruption and crime, they spoke about her children, chuck telling her that he was spellbound with Briana’s beauty and charm. She said that Cary was her imaginary lover. She was totally enamored with his boyish manners and killer bod. They laughed at these observations and the conversation quickly turned to sex and the other night. “Well, what did you think?” Brenda asked Chuck knew exactly what she was referring to, and he answered honestly. “I had a raging hard-on all the way home, and had to beat off twice to get to sleep.” Brenda squealed loudlywith approval.
“I have to admit, my pussy was pretty wet when I got into bed, I won’t say that I masturbated, but I will say that my vibrator did.” Chuck laughed loud and long at that one. “Was I good?” he asked her and with that she doubled over and sceamed that she thought she was going to pee her pants, adding “If I had worn any.” They both laughed very hard and just made it to the restrooms of the second floor restaurant he had selected. When they rejoined each other they had a fabulous meal at the oldest Chinese restaurant in Chinatown. As they left the restaurant, Chuck led her through the various shops and sidewalk stands that created a wonderful blend of old and new offering anything anyone could possibly ask for. At the door of one shop a small man whispered that he had potions that would keep Chuck erect for hours and make his lady a tiger in bed. “Oooh Baby, let’s get some”, Brenda joked “would you like a little tiger pussy tonight?” Chuck smiled and led her away from the shop. They spent an hour or so walking through the array of stands and storefronts until they reached the car. When they got in, Brenba put her arm around Chuck’s neck and she kissed him passionately. He kissed back. Her hand was massaging his swollen cock through his pants and his hands were molding the firmness of her breasts.
They made out like teenagers for several minutes, when Brenda said,” Take 159th street to Torrence turn right to 172nd, we have an account at that suites hotel there.” Chuck manuevered the car into traffic and before he knew it he was lying naked on the bed at that hotel with Brenda sucking his cock like she was starving for it. He pulled her around to get her pussy close to his face, her natural growth of pubic hair excited him as he ran his nose through her bush. “Do you want me to shave,” she mumbled as she talked around his dick. “No, I love it the way it is,” he answered as he ran his tongue deep into her folds and massaged her clit with his lips. They ate and sucked each other for several minutes, bringing Brenda to at least two orgasms and heightening the sensativity of both of their bodies. Chucks cock was diamond hard and throbbing in her mouth, he wanted to release his cum into either her mouth or her cunt, he was not particular, he just wanted to cum. She increased her sucking and bobbed her head more quickly over his cock, sensing his need for relief. His head jeked away from her pussy just long enough to choke out “Oh fuck, I’m cumming, oh baby suck that cock” Brenda took the whole length of his shaft into her throat and swallowed his copius load as he pumped it from his swollen balls.
Brenda actually experienced another orgasm as he came. She was ecstatic.
They lay quietly for several minutes letting the magic of the moment fully sink in. Brenda kissed his cock lovingly and he returned the gesture by dipping his tongue deep into her pussy and licking toward her asshole causing her to squeal with delight.
They rested for a short time and Brenda began sucking Chuck back to life. “Baby, I need this deep inside my pussy, please.” she said as his cock began to return to its fucking posture. Chuck sank his cock fully into her in one stroke, and Brenda grunted approvingly as he bottomed out. “Oh yeah baby,” she moaned “fuck that tight cunt of mine, give me the fucking of my life.” Chuck did just that, three more times that night before they left the hotel at three in the morning when he took his date home.
Sunday morning, Brenda awoke to sounds in the kitchen that told her that her babies had been making breakfast. She drug her sore pussy out of bed and wrapped a robe around her and walked down the stairs to the kitchen. “Holy shit, Mom” Briana gasped. Brenda was surprised by her language, but realized that she probably did look awful. “Language, young lady!” she spat at her. “Mom, you look like you got gang banged by a herd of caribou.” That comment caused Brenda to chuckle and reflect on her previous evening. “What’s for breakfast?” she asked “Breakfast?” Briana shot back, “it’s two in the afternoon. You need a good spanking young lady.” she continued causing her mother to blush deeply. “Okay, okay, so I had a little fun last night. It’s not like I do that very often and besides I really like this guy.” she said defending her appearance and obvious lack of decorum last night.
“Hey, Mom, we’re just messing with you. We were so glad you went out and got laid, you were getting bitchy as Hell.” With that Brenda shot across the kitchen and slapped her daughter hard on her cute little ass. They both laughed as they wrestled around together in mock anger. “He must be something, Huh Mom?” Briana ventured. “That’s none of your nosey assed business, you little shit.” Brenda said playfully. “Well, from the looks of you, he must have some stamina, too.” Cary added. With that Brenda said “Enough. I am going up and taking a shower.” Briana said “Take two, and douche”, Brenda chuckled all the way back to her bathroom. “Douche” she laughed, “Fuck I need a firehose to get all that out of me”
To be continued : See Chuck’s Chicago Assignment II
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