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A family date - Simon - 11-25-2025
Chapter 1. On the Road
Charlene gave him one of her hopeful doe eyes, deep blue, sparkling, luscious nipples pressing hard against her tight T-shirt. John knew he couldn't resist that look when she gave him it. They both knew it.
"It could be so much fun, John. The kids have been asking about that fascinating stop in the Enchanted Forest off I-5 just past Salem for years. Darling, you know they'd love it if you took us there. They might be getting a little too old for the place, but they've always wanted to stop and never had the chance. We could spend a long weekend there. Nobody knows us, so... you know... that date idea we were talking about a few weeks ago? The kids are in."
John still vividly remembered their conversation about the possibility of the two of them "going out" with Charlene's children. It had led to a passionate lovemaking session in Charlene's bed. He raised an eyebrow, and his penis stirred at his girlfriend's suggestion. John was in his late fifties, with brown hair that was beginning to gray, and a slight teddy bear belly, which Charlene not only didn't seem to mind but actually found endearing. Charlene was about twelve years younger, but they had been together for almost a year and got along well. With the mother and her two children, he had found something he had been searching for his whole life—something very special, very intimate, and completely forbidden in everyday life. "You talked to the kids about this idea? Wow, Char, I really didn't know if you were serious or if it was just one of your perverted pickup lines." Charlene grinned at him. "I would have thought you'd learned by now, baby. Behind every temptation lurks a good opportunity when you're dealing with my family!"
John grinned back and pulled her into a tight hug. She turned her face to his and gave him a deep French kiss, their tongues entwined.
"I'm still learning, you sexy slutty mommy," he giggled, pinching her ample bottom, his hand creeping up to just below the leg of her shorts. With a cry, she squirmed away, her voluptuous bottom and breasts jiggling seductively.
Charlene was a rather tall woman with auburn hair, a fair complexion, and curvy figures that looked good, almost a little plump. She had the figure of a mother, not a model, but although her figure was sexy in a hot, maternal way, that wasn't what drew him to her so strongly. It was her passionate, natural, uninhibited hunger for sex in all its forms that intoxicated the man. At the moment, she was signaling this hunger not only with her grin but also with a rather prominent hand, which was gripping the stiff shaft of his penis through the front of his jeans.
"Fuck now, or do we wait until the children come home from school?" he asked.
“Now,” she replied. “Then we’ll pick them up from school and tell them the news. Let’s do it this weekend. The kids have a short school day on Friday, so we can start early. Do you think you can finish at noon? Or do I have to show your boss my tits again to make it work?” Charlene giggled as he pinched her bottom again.
“I love you, you hot cunt,” was his only reply as he followed her ass upstairs into the bedroom.
Bernie, the family's large Bernese Mountain Dog, who had been sleeping in his favorite spot at the top of the stairs, woke up and caught up with them at the bedroom door. He was panting enthusiastically. John turned, winked at him, and patted his head. "Not this time, pal. You'll get your chance later. Consider it a promise." The door closed behind him, and the big dog wondered if his status as the alpha male, the one who wanted to steal the show, would last.
~~~
So this was the conversation from earlier in the week that brought the four of them south on Interstate 5 on a warm, sunny Friday afternoon in John's large, comfortable, and well-equipped double-cab Ford pickup truck. Poor Bernle wasn't there; he was being looked after at home by Charlene's favorite neighbor, a teenage girl who regularly house-sat. John was driving, with Colton beside him in the front seat. Charlene's blond son had moved so close that he and "Uncle John" were almost hip to hip. They were obviously fondling each other and talking quietly, the boy occasionally giggling. From the lustful look on John's face as he glanced in the rearview mirror, which was adjusted to give him a good view of what was happening in the back seat, Charlene was fairly certain that her son had the man's erect penis out of his pants and was fondling it with a curious little hand as they drove and talked.
If she knew John at all, she was pretty sure Colton's small, ten-centimeter penis was also peeking out of his pants, undoubtedly warming her friend's larger hand when he wasn't using it on the steering wheel. That was fair, because in the back seat, Charlene and Mallory were also snuggled close together, making out ever since the truck had pulled out of their driveway. The mother sat behind her son on the passenger side, and her daughter was buckled into the middle seat. Charlene knew that proximity wasn't the only reason for the middle position. Mallory was an incorrigible show-off and always seemed to find a way to position herself so that John could get a good look at her. They had dressed appropriately, Charlene in a loose, lavender floral summer dress, white sandals, and nothing else, leaving her "date" free rein on her mother's body.
Mallory was also scantily clad, wearing a tight, short pink T-shirt so sheer that it revealed her shapely teenage breasts and swollen nipples. The shirt bore the words "DAUGHTERS MAKE THE MOST OF IT..." in black letters. The last line showed only the top third of five more letters.
Charlene knew the word was "LOVER," but passersby puzzled over the clue and rarely guessed it, or when they did, they seemed confused by its meaning. Beneath her beautifully smooth, ivory-colored stomach, revealing her navel, the slender teenager wore a short black denim miniskirt. Her long, slender legs were concealed in a pair of black, open-toed high heels. Black perfectly complemented the girl's fair skin, pouty pink lips, blue eyes, and long blonde hair. The flaxen-haired teenager wore her underwear as a matter of course and needed no makeup other than her favorite glittery lip gloss.
Charlene loved it, even though her daughter's fashion sense often made her feel like a hopeless middle-aged mother. Oh well, she told herself; there are worse things in life than being the mother of a bisexual little slut who gets good grades and idolizes her mommy's pussy. Keeping the little one's often rude taste in clothes in check was a small price to pay. Her clitoris twitched, and she felt a trickle of warm cream seep from her cunt into the sweaty cleft between her ample buttocks.
This outing was all about indulging in that positive aspect. The hot and excited mother knew exactly what the delicate word "LOVER" meant. At that moment, her precocious, sexy young daughter leaned towards Charlene and gave her a long, incestuous, open-mouthed kiss. Her soft hands caressed her mother's breasts beneath her summer dress, while the girl rubbed her smooth, bare pussy against her mother's cupped hand and warmth-seeking middle finger.
When Charlene first approached John about accompanying her family on such a trip, John seemed hesitant, but it didn't take long for him to warm to the idea. Char had longed to explore her bisexual and incestuous desires; she often yearned for a place where she could openly "date" her daughter as her lesbian lover. She enjoyed the thought of the questioning glances and inappropriate thoughts of observant strangers that would undoubtedly follow if the two held hands and kissed in public, given their age difference and obvious physical resemblance.
This meant, of course, that her friend John had to act not only as chaperone but also, to be fair, as young Colton's companion. Her son had taken quite a shine to John in recent months, and Char knew that Colton had been pleased by this and had apparently gained a new sense of self-worth because John openly accepted the boy's homosexual inclinations. It was a kind of male validation that Colton had obviously needed and missed since his father had left the family when the children were very young. Although John admitted to being bisexual himself, he might have preferred a more open approach to family life. But for some reason, Charlene had insisted on this Dutch dating arrangement, as she called it, and so he had agreed for her sake. Charlene's children never ceased to amaze him. They were sensual, sexual, and so well-balanced. As experienced little lovers, they struck him as mature and wise in some ways, but in many others, still just children. The intense and intimate attention of his date during the drive awakened John's penis and heart to the numerous sensual possibilities of this weekend fling. He wasn't used to openly gay dates, but during the drive, he felt Colton's unbridled lust for his penis and felt his testicles stir with anticipation. John decided to make the most of this damn weekend, one way or another.
John's penis throbbed as a young hand slipped inside his trousers, clutching and caressing his sweaty testicles. He felt a lover's breath on his right earlobe and turned his head to receive a warm, sexy kiss from the boy. The heat of the kiss momentarily took his eyes off the road. Suddenly, he decided he needed a break from driving. He squeezed Colton's bare, smooth thigh reassuringly.
A few kilometers further south, a rest area came into view, and John drove his car onto the exit and into the parking lot.
"Do we need petrol yet?" Charlene asked from the back seat, taking her hand out from between her daughter's spread thighs. Mallory sat up and checked her lip gloss in the rearview mirror.
“No,” said John, “but I think your son and I need a bathroom break. Right, little one?” He ruffled the boy’s hair. Charlene saw her son blush, unsure of what John meant. Then she saw the man’s reassuring wink, and his enthusiasm overwhelmed him.
“Yes!” “Of course!”, Colton agreed, and the girls could tell from his shrug that the boy was putting his stiff penis back into his shorts.
After John got out of the truck, he turned and pulled a bill from a money clip in his front pocket. “Here’s a twenty, girls, go in and get some snacks and maybe some iced teas to go, please? The kid and I will be there in a few minutes. Get Colton a raspberry Arizona.” He knew what Colton liked. The girls giggled as they watched John’s hand casually cup his date’s small, round buttock through his cut-off jeans, while the boys turned and strode purposefully toward the building’s entrance together. They had also noticed the large bulge in John’s crotch and suspected that Colton would earn that iced tea.
"Ugh, men's restrooms are so disgusting," Mallory said to her mother as they walked to the supermarket together. "Anything can happen in there."
Charlene just giggled, put an arm around the blonde's slim waist, and pulled her daughter closer. "I wonder how you know that," she giggled. "But you're right, friend. Kiss me."
"Goodness, Mom!" exclaimed Mallory. "Here?" Her gaze scanned the parking lot.
"Shut up," Charlene grinned, giving her daughter a quick, passionate kiss. "Nobody knows us here." After a swift kiss and a brief hug, they slipped inside to go shopping.
It was getting warm, the truck was parked in the afternoon sun, when John and Colton returned almost 15 minutes later. The girls felt too exposed to do more than a little kissing in the parking lot, where people were coming and going, and had sorted the snacks. Mal was slouching on the bench seat, chewing on a red licorice stick, her legs spread wide to cool down. Charlene fanned herself and sipped a Diet Coke. She handed Colton his tea and John a lemonade. "Thanks. Keep the change, you sluts," John said from the driver's seat, glancing back and winking. The girls smiled crookedly at him, and Mallory stuck out her tongue and lifted her skirt to give him a glimpse of a smooth, bare little pink slit. Colton, who had seemed a little flushed and out of breath at first, saw his sister and laughed, his brown eyes sparkling again. Then he slid to the left and snuggled under John's arm like a teenager as the pickup truck drove out of the parking lot and back onto the highway.
“Well?” Charlene finally asked, sounding exactly like a mother who needed a report on her child’s behavior. Mallory giggled.
John gave her a refreshing smile in the rearview mirror. "Your little stallion here really blows well."
Then Colton turned to them, beaming. "Uncle John gave me a blowjob this time too!" he announced with a hint of pride in his voice.
Charlene saw that Mallory couldn't hide a jealous look. "Don't worry, baby," she said to her daughter, patting the girl's soft, peach-soft knee comfortingly. "When we get out of those seatbelts again, Mommy's going to give you a good licking of the cunt."
The boys sipped their drinks and giggled gleefully about the "bitches" in the back seat as the truck quickly accelerated to highway speed.
"Maybe we can find something for her in Oregon," Colton suggested after a few minutes.
"Maybe, maybe," John replied approvingly. "I like the way you think, baby. How about you take out your sweet cock and give your uncle something to fondle again on the way, you sexy little cock-sucker."
Colton grinned proudly and did it.
~~