Chuck’s Chicago Assignment III
by 1stprize
They saw one another socially, which meant having passionate sex, every night at Chuck’s hotel. Brenda had a key to his room, he had a key to her house as well. They had the best of both worlds.
Brenda had to visit another plant on the West coast, so she told Chuck that she would Skype him in the evenings and they could have some hot phone sex while she was gone. She actually tried to take him along but there were absolutely no similarities between the plant she was visiting and the one in Chicago. thus Chuck was stuck there to continue the work.
The first night they Skyped, Chuck was delighted that Brenda was able to “talk” him to an orgasm. She and he watched each other masturbate on their computer screens and came to very satisfying climaxes. He enjoyed watching her sit naked as he related project news and events to her. “Why can’t we do this all the time?” he asked jokingly “Because we would never get anything done.” Brenda answered. They had fallen into the habit of saying “I love you.” at the end of each call, and Chuck was very sincere when he said it. Brenda was too, to an extent, but still thought she loved the sex and his cock more than she did the man and his heart. Time would tell.
Chuck decided to check on the kids while she was gone, they had decided to stay at home without adult supervision, and Brenda agreed owing to the fact that they had never given her any reason to question them. Chuck meant to call ahead, but got busy with other things and did not get to.
He drove to her house just after dark, and parked on the street as there was another car in the drive. He walked up to the door and rather than ring the bell used his key to gain entry. As he moved through the front hall toward the kitchen, he heard the unmistakable sounds of sexual activity. He slowed and began to back out of the front door and back to his hotel, but the curiosity overwhelmed him. He crept stealthily toward the kitchen and saw that the mancave was lit sparingly. That is where the sounds were coming from. He heard foreign accents, both male and female, seemingly begging someone to go faster and harder, the male voice unintelligible but very animated and excited. He stood in the corner of the kitchen and peered into the room.
There he saw Cary lying on his back with a beautiful redheaded girl riding his cock. He had his eyes closed and she was speaking with a very thick accent, maybe German, no it was Gaelic, she must have been from Scotland. Her breasts were gorgeous, with nipples swollen like large plums at the end of her aureoles. Her red hair was swaying with her movements as she moved toward her climax.
On the other side of the room was Briana, on all fours with a handsome young man with the same red hair and features of Cary’s lover. Brother and sister? Chuck thought to himself. Was he watching a brother and sister fuck a brother and sister? His cock was raging. He looked at Briana’s breasts swinging beneath her as she moved with her lover. She seemed totally engrossed in the process and the boy was actually speaking a foreign tongue as he drilled his cock into her. The girl riding Cary began to draw deep hoarse breaths as she picked up her pace. She was closing in on an orgasm of epic proportions and Cary was squeezing her fabulous breasts as she increased her stroke. “Oh, Cary, foook me, darlin’ poosh yer cack into me hairder, make me cum.” Instantly, Chuck fell in love with this girl from the Emerald Isles, wherever she came from. She began to romp on his cock and shortly was in the throws of an intense orgasm that she shared with her lover. Cary followed shortly with his own climax as he flipped her over and finished her off.
The boy behind Briana stiffened as he unloaded his cock into her beautiful pussy. She, like her mother had a natural growth of pubic hair. Hers was dark brown. The little girl under Cary had a pussy covered with bright red fuzz as red as the hair on her very pretty head. Chuck as backing out of the kitchen when he heard Briana say “Isn’t incest just the best?” to which the others all agreed. “I jus lo’ sooking Sean’s big cooock and fooking ‘im, do you do th’ sim to Carii?” Briana answered enthusiastically “Fuck yes, Shelly, I’ve been sucking his cock since he was ten and loving every drop of his cum.” Cary added “Every day since I was ten, she hasn’t missed a day.” Briana added, “Sean, you should start wearing a kilt, so I could suck your cock without dropping your pants.” They all shared a laugh and Chuck took that opportunity to make his exit. As he drove to his hotel, his mind was reeling. His cock was rock hard and he was lusting after the two gorgeous teenagers he had just watched get fucked. As soon as he reached his room he jerked his cock until he came, three times.
Chuck was faced with a dilema, should he tell Brenda what he had seen, or should he protect the privacy of the kids by saying nothing. His head was saying one thing, but his heart was telling another story. Brenda was due back in two days. He had time to think, and time to also fantacize about the beautiful bodies of those two wonderful girl/women that he had seen.
Brenda’s plane landed late at Ohare and Chuck was there to pick her up. They went out to dinner at a local pub near his hotel. “Well, did they burn it down?” Brenda joked. Chuck thought before answering. “They were fine, they didn’t call even one time. I rode by one night to make sure everything was okay but there was a car in the drive, and the kids that were there were apparently leaving, two red heads, boy and a girl, so I just drove by. I didn’t want the kids to think I was spying on them.” Chuck was smugly proud of his half truth, it had the ring of truth and did not reveal any of the details. “Oh, that was the McGowan kids, Shelly and Sean they have been friends of my kids since their parents moved here from Scotland three years ago.” Brenda said as a matter of information. “Beautiful girl,” Chuck added. Brenda looked across the table wryly and spat “Pervert, she’s only fifteen, her bother is seventeen. I think Bri has a little crush on him, and Cary would love it if Shelly would show him the time of day.” Chuck nearly choked at that as he thought he wished she would show him as much time as she showed Cary.
As Chuck drove her home he was devisng a plan to reveal what he had seen without involving the perpetrators. He would tell her a story about someone he knew from the past. “Would you like to stop by my hotel for a nightcap?” he asked knowing that they would almost certainly have sex and he would have his opportunity to tell his story. Brenda leaned onto his shoulder and sighed. “I thought you were never going to ask.” she said as he turned the car toward his hotel.
After they entered the room, all of one minute passed from fully clothed to stark naked occured. Brenda was on her knees sucking his cock like she hadn’t seen him for a year and they were soon involved in hot, raunchy, messy lovemaking with a large side of animal sex. After two almost violent orgasms, they rolled off each other and caught their breath.
“You know not every Mom could fly off to the West coast and leave two teenagers alone like that. You should be very proud.” Chuck started the story “Oh, I am,” Brenda offered “Those kids have always been great, well not always, until Bri was about 12 she and Cary fought continuously, but right after Cary’s 10th birthday, she started treating him like her best friend and I suppose they have become that, best friends.”
Chuck continued his story. “I had a female friend at one of my client plants,” “A fuckbuddy?” Brenda interupted. Chuck frowned at her and continued “Anyway, she had a daughter and son just like you, the boy was older I think, anyway, she left them alone for a weekend and came home unexpectedly,”
” and they had thrown a huge party and broken all the china” Brenda interupted again. Chuck once again scowled at her and continued “No, when she came home she found them having sex together, fucking like champs in her bed.” Brenda stopped to ponder what he had just said. “Damn, that is so hot.” she finally said “What if my kids were fucking each other?” her voice had a ring of excitement to it. “Oh fuck, Chuck, what if Briana was teaching her little brother about sex? That is so fucking hot!” Chuck was pretty confused now, just like when Brenda had messed with his mind early on, she was totally blowing it now. Brenda became very agitated and horny. She reached and started stroking Chuck’s cock into a raging hardon again. “I have seen Cary’s cock when it was hard when I went into his room on a Saturday morning to get his laundry. He was still asleep and his morning hard on was sticking out of his shorts. I have to say I was impressed. Even at fourteen his cock is bigger than his Dad’s was. He is almost as big as you, just not as thick.”
Now Chuck began to understand her describing Cary as her imaginary lover. “I’ve seen Briana in the shower, too. You would love to dive into that muff mister, covered with the softest fuzz you can imagine. I know how much you love my pubic hair, well hers is just as pretty.” Now Chuck’s cock was like a diamond again and he jerked her legs apart and began to enter her, “No, stop,” she said “Let’s lie on our sides and you come at me from behind, I want to fantasize about my baby boy. I am going to call you Cary while you fuck me, okay?” “Yes that will be fine, Briana.” Chuck answered. Brenda moaned deeply as he slipped his rock hard cock into her blazing hot pussy.
They fucked like that long enough for Brenda to have two intense orgasms. They were both spent when they finished. They lay and held each other until the alarm went off. It was morning. They had finally done it, they actually spent an entire night together.
Brenda went into the shower, and sent Chuck to the car for her suitcase and makeup bag. She showered and they went out to breakfast. She texted the kids that she was fine and that she and Chuck had some business to take care of and she would be home Sunday evening. If her kids were fucking each other she wanted to give them as much opportunity to enjoy each other as possible.
After breakfast they returned to the hotel and watched a movie on the room TV. They had been, for the most part, silent throughout the movie, just some petting and kissing during the more romantic parts, but both reflecting on the revelations of the evening before.
Finally Chuck broke the ice. “So, do you want to tell me about it?” he asked Brenda looked at him and her eyes were filled with excitement.
“When I was thirteen years old my older brother came into my room and began playing with my pussy. I enjoyed it so much that I asked him to do it again the next night. We started playing with each other every night which led to us fucking and sucking. We did that for a couple of years. My Mother never knew but my Dad caught us in our barn hayloft one day. I was fiteen. Daddy took me to his room and fucked me with his big fat cock. Instead of being mad or horrified I was so happy and I started fucking him and my brother as often as I could.
Mom passed away when I was seventeen and my brother who was two years older went off to the service, so my Dad and I fucked every day, I slept in his bed. If my kids are fuck buddies, I want them to feel free to fuck or suck as often and as freely as they want to. I want them to feel free enough to fuck in front of me. I would love it if Cary would crawl into my bed and make love to me. I know that is a little out there, but that’s is what I am thinking.”
Chuck took her into his arms. “My turn.” he said “I was eleven, when my aunt saw me peeing behind the garage, she told me that she was going to have to punish me. She took me into her apartment which was above our garage and fondled me until my little cock got hard. Then she sucked on it until I actually peed again. She played with my dick as often as we got the chance, which during the summer was almost everyday. She was the youngest of my Mother’s sisters, so she was quite a bit younger than Mom. One day when I went to her apartment to get my dick sucked she was there sucking my younger sisters pussy. She showed me how to put my dick into my little sisters pussy and we went to town. That went on until I packed up and left for college.”
Brenda’s eyes were wild with excitement and wonder. “Oh Chuck, no wonder you and I are so compatible. We share so much of the same kind of history. Oh, Baby, I so hope that the kids are incestously involved.” Chuck took her hand and told her the truth about the night at the house. Brenda was so hot that she immediately stripped off her clothes and they fucked right then and there. When they finished she told Chuck to get dressed. “We’re going to go over to the house and fuck our babies.” she said.
When they reached the house, Chuck saw the McGowan’s car in the drive. His heart leaped in his chest. Brenda looked at him and smiled, “Maybe we are going to get some Haggis with our main course.” She giggled as they quietly entered the house.
The sounds from the mancave were inmistakable. They stripped naked and entered the kitchen, as they moved to the door they heard the Scotish Brogue coming from Shelly’s pretty little mouth. She was begging her ‘loover, shoov yer loovstick into me arse’ They stuck their heads around the door and Briana was sucking her brother’s cock while Shelly was lapping at her pussy, and Sean her brother was slamming his cock into her tight little ass.
They walked into the room and began fucking on the floor right next to the kids. It was a few seconds before they noticed the intruders. “Fuck, mom, what the fuck?” Briana was freaking out. “Holy shit.” was Cary’s remark. Brenda and Chuck didn’t miss a stroke, they fucked until both fell into a heap after cumming harder than they ever had together before. “Did we do okay?” Brenda asked the kids. Sean ,moved over and positioned himself to fuck Brenda, “Oh yeah, Baby, I’ll take some of that.” she said as she stroked his fat hard cock and guided it into her waiting cunt. Chuck moved over to Shelly, “May I?” he asked as she spread her legs to take his swollen member. “Aye” was her immediate response.
Briana looked at her brother and smiled. “Looks like we aren’t going to have to sneak anymore baby bro'” and with that she mounted him and fucked like there was no tomorrow.
The End Thank you for reading, I hope you enjoyed the series.
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