Chuck’s Chicago Assignment V – An evening at the Taylor’s
Introduction:
Chuck and Brenda are engaged, Briana and Cary are looking for some hot fun.
Briana listened intently. Her head cocked toward her brother in acknowledgement of his concerns. “Maybe you’re reading to much into this or maybe you’re over complicating things. I mean it’s just sex, I mean she fucked you, I fucked Chuck, Mom ate my pussy, it’s not like they asked us to drink blood and become vampires, or join a cult or anything. You and I have been sexually involved for over four years, since I was twelve. We are still involved, that hasn’t changed, and the fact that Mom and our soon to be ‘Dad'” Briana made the same gesture “have decided to become a more intimate part of our lives may be a really good thing.” She turned the car onto the street where the Taylor’s home was. “What I am happy about is that our Mom is happier than I have ever seen her, she smiles all the time, she sings, she fucking sings in the kitchen. When was the last time you heard Mom sing? She fucking sings.” Briana said to make her point. “Brud, let’s not fuck this up for her. She is my life and I love her so much and to see her happy like this is making my heart almost burst.” Cary saw a tear trickle down his sister’s cheek. “I know Babe.” He said. “It makes me feel the same way. I just hope it’s for real.”
Briana brushed away the tear, “Oh this guy is for real, all right. He is 23 carat bawt gold real. This is the nicest guy Mom ever met, so we, you and me, need to do everything we can to make this happen,” “Okay Sis,” Cary responded as he leaned over and kissed her on her cheek. ” Now let’s pull our selves together, on the other side of that door is much fucking fun.” she said and they both laughed at her Indian chief impersonation.
As they entered the foyer, they took off their clothes and folded them into the cubbies that lined the foyer wall. Briana noticed that several of the cubbies already contained clothing from people who were already there. Since her first visits as a curious seventh grader the Taylors had become noted for their sex parties and for allowing access to their home for orgies and other forms of sexual perversion. They had just about every thing one could want. Couples having clandestine affairs met there away from prying eyes and traceable hotel receipts. It was kind of a win-win for everybody. The Taylors received benefits, like the lease-free car in the driveway supplied by the dealer who met his secretary there every Wednesday, and the landscaping courtesy of the woman who owned and operated the business and met her Mexican lawn boy there. The Taylors had found ways to make their perversions pay dividends.
As Briana, now naked, went into the front parlor, she ran into a school friend Whitney. Whitney was the class chubby. She was a pretty girl with long blond hair who was always overweight from their elementary school days. She wasn’t grossly overweight, but today’s standards of sleek and slender made her the butt of many jokes. Briana knew that she seldom went to school social functions and never dated boys, so she told her about the Taylor’s home. Since she had told her, Whitney had found self confidence and esteem. At the Taylor’s there was always someone there she could find to have sex with her. She had not found a steady guy yet, but she was getting the sex she craved and now carried herself with more self assurance. “Hi, Sweetie” Briana said as she hugged her friend. Whitney was a year younger than Briana. “Who’s here tonight?” she asked. Briana was startled by the concerned look on Whit’s face. “Bri, I have my Mom with me.” Whit offered. “She has been so stressed lately and I know she hasn’t had sex for years, so I just came out and told her about this place.” “What did she say.?” Briana asked. “How did you even get up the nerve to tell her? I still haven’t told my Mom about this place.” Whitney was obviously agitated and nervous. “She is in there waiting for something to happen. Bri, she is so horny, if somebody doesn’t come ask her to fuck soon she is going to be devastated, I am so worried.” Briana looked at her younger brother. “Hey, Brud, wanna be a hero?” she said. Cary shrugged. “I’ll suck your cock a hundred times.” Whitney pleaded. “I’ll even let you fuck me in the ass, whatever you ask for, pleeeease.” she was desperately looking at Cary. Cary leaned forward and kissed the chubby girl on her succulent lips. “I’ll do it, but not out of pity, I want to make this the best night of her life.” Briana beamed with pride. “Isn’t he the best baby brother in the world?” she said to her friend. “Oh Cary, I love you so much.” Whitney said her new best friend. Cary walked through the door and saw the woman who looked like the future Whitney. The woman and the girl could have easily been mistaken for the other. Their stature, frame and hair color was almost identical. Their bodies were like mirror images. Whitney was thick in the middle and so was her Mom. Both women had large full breasts, and if there was a difference it was there. The mother’s breasts hung lower and were slightly heavier than the daughter’s. Cary walked through the door and said “Hi, are you waiting for someone?” “My daughter should be back soon.” she said. “Oh, who’s your daughter?” Cary played his role. “I’m Charlotte Cummings, Whitney Cummings’ Mom.” she said, “Do you know her?” Cary extended his hand politely offering to shake hers. “Yeah, I sure do, very pretty girl.” he said. “Oh, you know she doesn’t have a boyfriend?” the woman added. “That’s good to hear.” Cary said He noticed that Charlotte’s eyes had not left his erect and throbbing boner. “My you sure have a nice penis.” she said somewhat embarrassed by her statement. “Thanks, would you like to touch it?” Cary asked. Charlotte’s breath caught in her throat, she leaned forward and she took his hard cock into her hand. She stroked it, first gently, then with more ardor and excitement. “That really feels hard.” she said “Have you been fucking someone tonight?” With that Cary pushed her back onto the sofa and said “Only you.” He held her down as he kissed her on the lips, their mouths became a battlefield for their tongues each trying to out perry and thrust the other. Charlotte let out a deep sigh. She was overwhelmed with excitement. Her body quaked as she reached for his young cock. “Please put it in me.” she said pitifully. “I need it so badly.” Cary aligned his cock with her hairy pussy lips. He thrust forward and his cock head slipped out because her pussy was so tight and poorly lubricated. “Wait.” he said and dropped to his knees and buried his head into her bush. Instead of the smell and taste he was expecting he found a sweet fragrance, and an almost taste-free slit. His tongue dove into the crack and forced it open. Charlotte hissed as he ran his hard tongue deeper and deeper into this cavern of delight. He stroked his fingers into the fold forcing it open and loosening the lips that had for so long been celibate. He continued to lick, suck and finger fuck her until she was pumping her hips to a mind blowing orgasm. She screamed with pleasure as she reached the brink. Cary was like a man possessed. He continued to suck and tongue her slit until she was begging him to please fuck her. He came to his feet with a raging hard on which he buried into her now soaking quim with one thrust. Her scream this time was from pain instead of lust. Cary began pumping wildly into her. After the initial shock of the entry she began to feel the expanse of his cock inside her and realized that his cock was perfectly lodged against her g-spot. The pumping was driving her wild. She pumped in response to his movements and soon she was going over the waterfall of yet another hot orgasm. Cary was just getting started. He pumped into her as hard and fast as he had in the beginning. Charlotte was babbling incoherently as she was brought from one orgasm to the next. She had lost all reference to time and events. She was in her own little heaven feeling her pussy being slammed over and over again by a cock one year younger than her daughter. She pumped her hips to get the maximum pressure on her g-spot. She kissed Cary’s face, lips, shoulders and anything else her mouth could reach. She was in the ultimate zone. Her young lover was pumping her with abandon. When Cary neared his cum, he tensed and a low growling scream started in the bottom of his throat and finally erupted with his cock as he spilled his balls into this amazingly hot quasi virgin. They slumped together on the sofa. Charlotte was covering his face with sloppy wet kisses. She squeezed him with her arms and legs as she bundled him up like a prize from the county fair.
“Oh Sweetheart, I think I’m in love.” Charlotte said. “My little girl would sure love to have a boyfriend with a dick like yours.” she continued. Cary blushed with embarrassment. “Well, I have always liked her.” he stammered. “Oh Baby, I wish you could start to date her.” Cary pumped his cock which was regaining its hardness into her now sloshy pussy. She moaned as she felt her pussy tighten around his ample boner. “Do you want more?” she breathed with excitement. Cary answered by slam fucking her to several more hard orgasms as he reached his own second ball draining climax. They fell apart and Cary still breathing hard looked at his partner. She was what he would describe as a BBW, big beautiful woman. She was softly sculpted with wide hips with a soft belly that cushioned his thrusts. Her breasts were full pendulous globes that were crowned with swollen aureoles capped with hard nips that resembled pink gumdrops. Her complexion was fair, maybe even pale. Her hair was flaxen like her daughter’s, her pubic hair was black and thick. It was uncanny how similar she was to her daughter. Except for her breasts, she was a clone. Cary lay trying to regain his composure when Charlotte rolled him over and took his cock into her mouth. Cary started to protest, but her mouth was so wet and warm he lay back and allowed her to suck him hard again. She continued to suck him slowly and lovingly. This was her way of saying that she was in love with him. She wanted him to know that she was completely enamored with him, and with his cock. She wanted him to know that she would do any thing to make him love her. She sucked his cock not just for his pleasure but for hers. She was loving the feeling of this young man’s diamond hard dick. Cary was enjoying the attention he was receiving from this woman. He was reassessing his first opinion of her and her daughter. Earlier he had thought that they were sort of sad, but now he was thinking that he had never had a woman give so much of herself to make sure that he was happy and satisfied. He caressed the back of her bobbing head. She responded by sucking his cock hard causing him to jerk as she bit lightly on his shaft. He was beginning to fall in love.
Briana walked into the bedroom on the second floor. There she found two lesbians who were showing first timer Whitney girl sex. Whitney generally found older men who loved her soft curves and youthful body. They would spend a lot of time sucking her soft pussy. She sometimes rode them like a cowgirl, but preferred getting fucked doggy style. When younger guys fucked her they would just jump on and shoot their wad and move on to the next girl. She sort of hated young guys. These girls met her in the lounge and began kissing her all over. She liked the attention. Her nipples were hard almost instantly. The first girl, Anna, put three fingers into her very wet pussy, while the second girl, Rachel, tongue kissed her. They overwhelmed her with a full on frontal attack. She was soon on her back and at the mercy of their hot mouths and probing tongues. She was in ecstasy. She had cum twice and was well on her way to her third. Briana watched, fascinated with the precision and accuracy of the assault. These two women knew exactly which buttons to push to get exactly the reaction they wanted. When they finished, they both locked Whitney between their bodies and ground their sex into her. Whitney responded by moaning loudly. “Eat me bitch.” Anna growled to her new conquest, and Whitney lowered her head and began to eat her first pussy. She duplicated the attention that she had received from the women just minutes before, her tongue dipping deeply into Anna’s quim as she fingered her ass. Anna emitted a silent scream as she reached her orgasm primed by the probing fingers of Rachel while she sucked Whitney’s cunt. Rachel brought herself off with her fingers in her pussy and the three of them fell exhausted onto their backs. Briana swooped in and grabbed Whitney by the hand. “Come with me” she instructed as Whitney came to her feet and Briana stole her away from the two surprised lesbians.
They ran down the hall to the next bedroom where Babe and Beau Taylor sat naked in recliners reading porn magazines. “Hey, Briana, Whitney, nice to see you. Boy Whitney, you look like you have been having a pretty good time.” Babe said to the girls as they closed the door behind them. “Rescuing her from the dykes.” Briana whispered with her finger to her lips. “Oh.” Babe said as she laughed and returned to reading her magazine. “Don’t worry, they have plenty of fresh meat to choose from in the lounge. They have been here all day, and they have an insatiable appetite for very young pussy. I’m surprised that they aren’t after you Bri.” Briana led Whitney down the back stairs away from the normal flow and back to where her mother and Cary were.
As they entered the room Cary was under Charlotte as she lay on top of him fucking his veritable brains out. Cary was completely in her control. He would have done anything at this point for his new lover. She was kissing him passionately as she reached yet another climax. Cary followed shortly with one of his own. The sheer number of orgasms that they had reached was epic even for a fourteen year old and a woman who had not had sex in over five years. Charlotte slumped onto Cary’s spent body. They had had an amazing night of sex.
Briana and Whitney watched as they untangled their bodies. “Whitney baby, I think I’ve found you a new boyfriend.” Briana looked at Cary to catch his reaction which surprised her. He reached over and kissed Charlotte on the lips. “Whitney, if it’s okay with you, I’d like to start seeing you.” He said. Whitney was gobsmacked. She wasn’t sure if he was being serious or if he was just saying this to placate her mother and keep her from dominating him again. “Are you sure?” she said as if questioning his sanity. “Oh yeah, I’m sure.” he said adding “I think you and I need to become boyfriend and girlfriend.” Charlotte was beaming. Her large breasts were swelling with pride at this point. “But, you haven’t even kissed me, or anything.” Whitney protested. With that Cary walked across the room and took Whitney into his arms. He kissed her as deeply as he had ever kissed anyone in his life. “I’ll be over tomorrow after school, and I am going to fuck you so hard that you will never want any other boy, ever.” and with that Whitney squealed and kissed him back.
On the drive home they were unusually quiet. “That must have been some fuck.” Briana broke the silence. Cary did not respond immediately. He sat and pondered the events of the night. “It was.” he finally broke his silence. He sighed deeply. “In the past week, I have been fucked by two women who were completely consumed with bringing me pleasure. My mother and Charlotte. They both had nothing but my satisfaction on their minds. Charlotte is a wonderful lover. Her pussy is as soft and wet and tight as yours, or Mom’s. Her tongue is amazing. I swear it felt like her tongue went down so far down my throat that it came out my ass to spank me.” Briana burst out in laughter at the mental picture that statement provoked. “Well, I guess.” Briana laughed out loud. “Brud, don’t hurt that girl.” she admonished her brother “She has been through a lot.” “Sis, believe me, I am convinced that Whitney will be just like her Mom. And if she is, I want her to be my girl.” Briana leaned over and kissed her brother on his cheek. “Don’t fuck this up, okay?” she said “Okay.” Cary assured her.
When they got home the moaning from their mother’s bedroom let them know that nothing had changed there. They stripped off their clothes for the second time and held hands as they went to Briana’s bedroom to have soft sex before sleeping.
After school the next day, Cary joined Whitney to wait for her mother to pick them up. As the silver SUV rounded the corner Whitney jumped to her feet as she grabbed Cary’s hand and led him to the curb. The back door sprang open and they piled into the back seat. “Hello, my darlings.” Charlotte gushed. “Did you have a nice day.” Whitney squirmed to get closer to Cary. She grabbed the bulge in his pants. “My pussy has been so wet all day I had trouble staying in my seat.” Whitney said. Charlotte boomed a laugh at her daughter’s humor. “I’m sure Cary is eager to fix that, aren’t you baby.” she directed her question to the boy with the rock hard cock in the back seat. “Oh man,” he said “My cock has been aching.” With that, Whitney kissed him hard on his mouth. Her tongue dove into his throat as if she were trying to steal his bubble gum.
Charlotte watched the two make out in her rear view mirror, her own pussy getting very wet. She drove as quickly as the speed limit would allow. As she pulled into the drive the two in the back seat were already too far to throw the door open. Whitney had Cary’s cock in her hand pumping it furiously as he had three fingers deep inside her pussy. Whitney had apparently removed her panties sometime before leaving school and she offered her hot wet cunt to Cary as soon as they got into the car. She had ripped his zipper down and jerked his cock out. She stroked him lovingly as they made out. Charlotte watched as her precious daughter took her boyfriend’s cock into her mouth and sucked him to a very hard climax. Whitney came herself as Cary finger fucked her hard as she sucked his cock. As they panted in the backseat, Charlotte told them to give her a minute. She opened the garage door and pulled in, she dropped the door and told them to get naked and get up to the bedroom. They giggled loudly and ripped each others clothes off. They romped naked through the house following Charlotte up the stairs and into her bedroom. They stopped short when they entered. The room had been changed over from Charlotte’s room into Whitney’s room. The king sized bed looked enormous. All of Whitney’s stuffed animals and high school memorabilia had been moved into this room. She had the “big” bathroom, her window overlooked the backyard, she was completely blown away. “Mom,” she said incredulously “I can’t believe it.” Charlotte came over and hugged her baby. “I want you to have a comfortable place to fall in love, baby.” Whitney grabbed Cary by his hand. “What do you think,Sweetie?” she said Cary didn’t care where he was going to fuck her, he just wanted to fuck her, now, without waiting anymore. He pushed her back onto the bed and climbed on. He aligned himself between her spread legs and soon his cock slipped into the velvety soft folds of her magnificently wet, hot, tight pussy. His breath caught in his throat as he slid his cock into a slow rhythm of ecstasy. Whitney fell into the same cadence as her hips rose to meet her lovers with every stroke. Charlotte sat across the room and watched her babies make love. Her fingers stroked her own clit as she brought herself to a slow and very satisfying climax.
The two love birds continued to kiss and swoon over each other. Whitney felt the familiar tingle beginning in her stomach, she increased her stroke to hasten her cumming. “Oh. Baby, Whitney’s getting ready to cum.” she said to her patient and persistent lover, Cary methodically maintained his stroke even though his lover was trying to rush him. He stroked ever so slowly causing his lover to become wild with lust. Everytime she pumped faster, Cary would kiss her neck and breathe quietly “Slow down Baby, slow down, you’ll be so happy you did.” Whitney would grunt disapproval and follow his instructions. His own pace increased slightly as he began his assent into paradise. His cock was increasing in size as he stroked into her deliciously hot pussy. She began to whimper as she now was completely under his spell. Her hips rose and fell meeting his exact rhythm and tempo. Soon Cary was pumping at the rate that made Whitney grunt loudly as she experienced a series of small, short, mind blowing orgasms, one right after the other. His cock head began to get larger with every stroke. Whitney felt his enlarged cock swelling inside of her as he was nearing his climax. She finally threw her head back and screamed as she reached the most intense orgasm she had ever felt. Her insides convulsed sending lightning bolts of sensations throughout her entire body. Her toes curled as she emitted a silent scream and felt her body virtually explode and then melt back together in ecstasy. She was breathing so hard that she was afraid that she would hyperventilate. Her back arched to thrust her cunt straight up to swallow her lover’s engorged cock. Cary shot his load, a steady stream of hot jism that shot directly into his lovers cunt. They both fucked violently for several minutes getting every last drop of passion out of their bodies before they collapsed into each other’s arms.
“Oh, my darlings, my precious loves.” Charlotte said breathlessly “That was so hot. That was beauty, that was perfection, that was the most incredible fucking I have ever seen.” The kids chuckled at her comments. “It was pretty fucking amazing for us too Mom.” Whitney said. She reached up and kissed Cary passionately on the mouth. “Was I as good as Mom? she asked putting him on the spot. “Infinitely better.” He answered. Charlotte smiled and said “Good answer, sweetie, good answer.”
“I baked you all cookies.” Charlotte said as if they had just come from the spelling bee. Cary rolled over onto his back, his young cock sticking straight up toward the ceiling. “Look, Mama,” Whitney said “Isn’t that the prettiest cock you’ve ever seen?” Charlotte nodded approvingly as she walked out of the room toward the kitchen. Whitney took Cary’s cock into her mouth and slowly made oral love to her new boyfriend. She sucked and licked his swollen menber with such tenderness that he nearly fell asleep while she pleasured him. “This is what it’s supposed to be like” he thought to himself. Whitney continued to love on his cock until he slipped into a deep naplike sleep.
When she returned with the cookies Charlotte found her two babies sleeping in each other’s arms. She kissed her daughter’s ample ass and stroked Cary’s withering cock. She pulled a light cover over the pair and left the cookies and went into the living room.
She picked up the phone andd called Cary’s mother. “Brenda,? Charlotte here.” the conversation began. They talked about anything and everything for several minutes. The conversation finally turned to the kids. Charlotte told Brenda that Cary and Whitney were now a couple. Brenda gave her blessing. She said that Briana had filled her in about last night, and that she was totally okay with them dating. She then added, “I understand that my son and you had sex last night.” Charlotte was surprised, but she knew there was no reason to lie about it. “Yes, we did,” she said “I found him to be a very mature and attentive lover.” she continued waiting for Brenda to object or say something negative, but to her surprise Brenda offered, “I know he is, and I am so happy that you decided to get he and Whitney together. I have always loved Whit, she is such a pretty girl, and I think Cary will be happy in that relationship.” Her tone was very friendly. Charlotte thought back to last night and the wonderful sex she had had with Brenda’s baby boy. “I’m glad that you are not upset that we made love.” she told Brenda. Brenda laughed sweetly, and said, “From what Bri has told me you fucked his brains out.” Charlotte shot back, “We fucked each other’s brains out.” then she added, “Listen, Whit and Cary are asleep upstairs, is it okay if he spends the night? I’ll bring him by in the morning to change clothes for school after we all shower together.” Brenda said “Sure, but if I showered with two hot teenagers in the morning, I’d fucking skip trying to get to school.” the two women laughed together and exchanged other pleasantries before hanging up. Brenda sat and pondered the phone conversation and thought about the shower scene tomorrow morning. Her pussy tingled between her legs. “Briana,” she called to her daughter. “Come tell me all about the Taylors.”
