Scott DeVine was approached by Julie, the wife of one of his best friends, Pete, to participate in an upcoming fundraiser for her women’s service organization. It would be a silent auction for five men, ages thirty to fifty. The catch was that he’d have to take this woman out for a fun Saturday night, with dinner and dancing. The organization would supply the men with $300 for drinks, dinner, wine, etc.
He reluctantly agreed but thought it would be good to put himself out there after his divorce four years ago. Scott had been on a few dates, but nothing promising. And he did not want to do online dating. “Swipe, swipe, swipe,” he’d joke with his married friends if they brought up Match or Tinder.
He was one of Oak Valley’s most eligible bachelors. The DeVine family, consisting of four brothers, were early pioneer settlers in Oak Valley in 1846, prior to the Gold Rush and California’s statehood. Scott’s immediate family, his grandfather, father, and two uncles, were successful in everything they touched.
Scott studied banking and finance in college and served as Vice President of a regional bank founded in Oak Valley in 1910. He was six feet tall with an athletic build, thick brown hair, and brown eyes.
During the week of the silent auction, he took care of all his personal grooming at his men’s salon. He had a haircut, waxed several areas, a mani-pedi, and whitened his teeth. As he left the salon, he looked in the full-length mirror and thought, “I need a girlfriend.”
+ +
Arriving Saturday at 5:30 pm, Scott met the other men backstage at the auction, where they were given a brief rundown of the evening: cocktails and mingling, dinner, and the auction results. During the cocktails and dinner periods, the women could place a secret bid in a bachelor’s locked box.
He learned he was the second-youngest guy at the auction, at age thirty-six. Besides the men, there were 20 other items the women could bid on: a trip to Lake Tahoe, a week-long beach house in Capitola, a gourmet dinner party for eight, four VIP seats for a 49ers game, and more. The bidding was open until 8:00 pm.
The chairwoman, Anne, sent the men out to “meet and greet” the women when the cocktail hour began at 6:00 pm. Scott casually mixed and mingled with the women, many of whom he knew from growing up in Oak Valley. He figured some older, divorced or widowed woman would win his auction, but was pleasantly surprised to see a fifth of the ladies in their late twenties and mid-thirties.
When dinner time was announced, about half of the women had already selected a seat at one of the round tables. Anne announced it was time to find a seat, and “the gentlemen will sit at the following tables.” She read off the man’s name and a table number. Scott was assigned to table five. Each of these tables had a small stand-up “reserved” sign on the linen placemat where the bachelor would sit.
Scott found table five and introduced himself to the ladies before taking his seat. He tried to speak with each woman, asking her name and a few details about herself. Their dinner was served, and the conversations flowed over the next hour. A few women shared their bids on a few prizes, and the bachelors.
Shortly after 8:00 pm, Anne was back on stage, ready to announce the winners of the 20 auction items. After she awarded the winners their certificates, she said those twenty items brought in $31,400. She then told the women that the five bachelors raised just over $16,000. “In all, tonight we’ve raised over $44,000! A new auction night record!
“And now for what you’re all here for… the gentlemen!” Anne exclaimed. All five men lined up on stage next to Anne. She announced the gentleman and the winning bidder. Anne did the first three guys, then said, “Only twenty-five dollars separated these last two gentlemen. Next, we have William, won by Michelle Todd. And our last gentleman, Scott DeVine, won by Susan Pierce.”
Scott looked out over the tables, expecting to see a woman raise her hand, her friends scream, something. But there was nothing. After a long five seconds, a woman towards the back stood up and waved.
“There she is, Susan Pierce. If all the winning ladies will come up on stage, we’ll take a few photos.”
As Susan crossed the room, Scott was pleasantly surprised. She was not an old, unattractive housewife like two of the other winners. Susan looked to be mid-forties, had a nice figure, blonde hair, and was dressed very well.
All the men met their “dates,” and the new friends exchanged phone numbers. As the others slowly moved off stage, Scott and Susan kept talking. They chatted out to her car in the parking lot. Susan initiated a good-bye hug, and Scott purposely held her a second too long.
In their fifteen minutes of conversation, Scott learned that Susan Pierce was ten years older than he was, forty-six. She was divorced, had no kids, and was an attorney. Susan admitted to being a fitness freak, working out 5 days a week and alternating between running and swimming.
Due to her fitness obsession, she had an incredible athletic body. Susan was taller than average, about five-ten, Scott guessed. She was a toned, size six, and about a 36C bust. Her eyes were a sparkling blue, and she had shoulder-length blonde hair with curls in the bottom third.
Scott called her the following afternoon, Sunday, and told Susan he secured a table for Saturday at one of Oak Valley’s nicest fine-dining restaurants, Vines.
They talked two more times that week, getting to know each other, discussing their careers, divorces, and being single and living in Oak Valley. Scott confirmed her address so he could pick her up for dinner on Saturday night.
+ + +
He wasn’t surprised to pull up to a newer home in the Sunwest subdivision. The homes in this development were over $1 million custom homes, with a handful of contractors’ speculative homes. Susan’s house was a “small” 2,500 square foot craftsman-style home. Most of the homes in this area were about 3,000 square feet in size, on large residential lots.
Susan was dressed beautifully in a mid-thigh “LBD” (little black dress) and nude two-inch stilettos. She wore pearl earrings and a short single-strand pearl necklace. She had her blonde hair curled a bit more than the first night they met and had a touch more makeup for the evening on the town. Scott liked what he saw and had a few naughty thoughts.
Susan and Scott were promptly seated upon arrival at Vines for their 7:00 pm reservation. They discussed a wine selection and ordered a Spanish varietal, Tempranillo, from Sunset Farms. Susan said she was in their wine club, and it is one of her favorite wines.
As dinner progressed, Scott noted that Susan was being a bit flirty and had dropped a few innocent sexual innuendos. As they split a slice of blackberry cheesecake for dessert, Scott mentioned the dance club, where he had a VIP table reserved, and noted that dancing didn’t start until 10:00 pm. It was now 9:00 pm.
“We have an hour, would you like to move to the bar for another drink?” he politely asked.
Susan looked at him, smiled mischievously, and said, “The only dancing I’d like to do with you is ‘Dirty Dancing’ back at my house. What do you think?”
Jokingly, Scott slightly raised one hand and whispered, “Check, please!”
After they both laughed softly, he continued, “I like your forwardness. Yes, let’s return to your house.”
Fifteen minutes later, Susan was leading Scott into her home. She asked if she should open a bottle of wine, but Scott passed. “I would like a small glass of water.”
Susan retrieved two bottles of water and invited him to join her on the couch. As they briefly discussed the other auction men and women, and wondered what those couples did for their dates, Scott moved his arm up and around her shoulder. She inched over right next to him and placed her hand on his thigh.
Scott leaned in and softly kissed her full, luscious lips. Her mouth opened slightly, and Susan began darting her tongue in his mouth. Their tongues were slowly waltzing. After ten seconds, he thought, She is a great kisser.
As they continued to kiss passionately, his free hand gently made its way to her breast and softly squeezed, and then teased her nipple, causing Susan to moan lightly.
Her hand only moved a few inches up his thigh before she could feel his erection. Using a fingernail, she went up and down his hard, veiny shaft. When she reached his glans, Susan squeezed hard and then simulated jacking Scott off.
“Ohhh, fuck. That feels good,” he whispered.
Susan snickered, “Just wait until my pussy squeezes your cock when I climax.”
“Really?” he said sarcastically.
“I paid a lot of money at the auction, so I hope you’re planning on spending the night. I want you to fuck my brains out. I haven’t been with a man in a long time,” Susan said.
“How long?” he asked.
“Over two years,” she stated. “I need a good ‘dicking.’”
Scott took those statements as an open invitation to speed things up and to take charge. He quickly unzipped the back of her black cocktail dress and then unclasped her pearl necklace, saying, “Just in case we get carried away.”
He stood up and gave his hand to Susan, assisting her to her feet. He unzipped the lower third of the LBD, watching it fall to the hardwood floor. As he kissed up and down her neck, he told her, “I love the no panties look. And keep on the stilettos.” Lastly, he made quick work of removing her bra.
Scott gazed at her perfect body, thinking of all the things they could do. “Damn, even better than I imagined,” he mumbled.
“Not bad for forty-six, right, kid?” Susan joked.
She stepped up to Scott, kissed his lips, and began unbuckling his belt. His clothes were soon on the floor adjacent to her dress, leaving only his boxer briefs. Susan went to her knees, looked up at Scott, smiled, and winked.
“Let’s see what we have here,” she teased as she pulled down the black undies.
Scott’s rock-hard eight-inch cock was pointing straight up toward the ceiling. Susan tried to wrap her left hand around his manhood, but could not fully circle his girth. She slowly stroked him a few times, producing one drop of pre-cum on his dick slit. She playfully licked it off.
“Don’t tease me,” Scott told her. “Suck it.” He paused for a couple of seconds. “I said suck my cock.”
He quickly grabbed her head and brought his large mushroom head to her lips. She opened her mouth, and Scott thrust his hips, shoving his dick into her mouth, hitting the back of Susan’s throat. He quickly face-fucked her for five more thrusts, making her eyes water, causing tears to run down her cheeks.
“OK, give me a second to catch my breath after gagging on your cock. I’ll suck the cum right out of your balls,” Susan laughed.
She had Scott sit on the couch, and she positioned herself between his legs. His ass sat right on the edge of the cushion, his large, hairless ball sack hanging down.
Susan began licking his long, thick shaft several times, then swirled her tongue around his meaty head, sending shivers down Scott’s spine. One hand softly rubbed his balls while the other held his cock at the very base as she bobbed on his knob. She’d suck on the tip for a couple of seconds, then take as much dick in her mouth as she could.
“Yes, suck on the head more. That will get me off,” he moaned.
She continued with the same method before going to all sucking. As she did this, her hands were stroking his shaft and fondling his jizz-filled testicles.
“Man, you can really suck cock. That feels so good,” he softly moaned.
Susan made eye contact, tried to smile, and mumbled, “Thank you.”
A minute later, Scott said, “I’m going to cum. You want it in your mouth? Tits? Face?”
Susan double-downed with her superior sucking skills, driving him crazy.
“Oh, shit, I’m going to nut,” he told her quickly.
She started jerking him off and told him, “Cum in my mouth. C’mon, Scott! Give me your spunk!”
“Agh!” Scott yelled, a split second before he climaxed.
Susan’s mouth was locked onto his large bell-shaped head, trying to suck the cum out of his balls, as she promised, with one hand jacking him off.
“Agh!” he repeated.
Scott’s cock twitched, and his hips bucked off the couch cushion, shooting a large volume of jizz in her mouth. A split second later, another gusher erupted in Susan’s mouth.
She pulled off his helmet and tried to swallow his huge load. As she gulped down his jizz, another rope of cum shot out and splattered against her face, down her right cheek, and chin.
“Yes! Cum on my face!” Susan said as she slowed down her stroking. She took another blast of jizz partly in her mouth and down her chin, then two more small blobs of cum landed on her upper right breast before his seed oozed out of his dick. Seeing this, she licked the cum off his helmet.
“Damn, that felt great. You can really suck cock, babe,” he told her.
Susan had a big smile on her face. She wiped up the two small blobs of spunk off her tit and licked her finger. “You came a lot, that’s why I had to swallow. I thought I was going to choke.”
“I’ve been told I have big loads by several women,” Scott said. “One woman had me cum on her tits. It was a lot of jizz.”
They both drank some water and then cuddled on the couch for a moment, catching their breath. Scott knew he needed a few minutes to get hard, so he anticipated going down on her freshly waxed pussy. His hand started mid-thigh and began softly rubbing a little, then moving closer to her kitty.
“I want you to eat me, and finger both holes,” Susan whispered as he began to spread her legs. “Wait, let’s go to my bedroom. C’mon,” she said.
She gave Scott a mini tour as they walked to her primary bedroom. He was impressed with the overall style of her boudoir. Not too frilly, but just enough touches of femininity here and there in the room. Susan had a king-size bed, a large, paneled headboard, two nightstands, a large dresser, a bucket chair, and a bench at the end of the bed. Her bedding was a light gray with a lavender paisley design, and the furniture set was a darker gray with silver hardware. There was a large HDTV high on the wall opposite the headboard.
“I brought you back here because I asked you to finger my holes, but let’s use my toys,” she said. “Fuck my holes with the toys and suck on my clit.”
Susan turned and opened the bottom drawer of her dresser, pulling out a black canvas bag, about the size of a shoebox. She set it on the dresser, unzipped the bag, and reached inside. She set a bottle of lube, an eight-inch jelly dong, and a stainless steel butt plug on the dresser.
“Are those for you?” Scott inquired.
“Maybe. You can use any of my toys, if you’d like,” she said, carrying the three items to the bed.
“I don’t think so. I’m an anal virgin,” he admitted.
“Oh, you don’t know what you’re missing. What about rimming? Has a woman licked your rosebud?”
Scott’s face showed his displeasure. “No, but one freaky chick licked my ‘taint’ after sucking and licking my balls,” he told her.
“I’ll be gentle, I promise. We’ll do it after you eat me,” Susan said. “Remember, I want both holes filled. The jelly dong in my ass, and the vibrator in my pussy. It can be adjusted to hit my clit when you’re not licking or sucking my pleasure nub.”
Scott felt a bit like a novice in the sex department as Susan finished her sentence. What other freaky things is this cougar into? he wondered.
Susan positioned herself leaning back on several pillows up against her headboard, with her shapely legs spread wide. Scott alternated between the legs, kissing and/or licking about a foot at a time, then switching to the other leg. As he approached her wet honey pot, Scott was met with the musky aroma of warm, wet pussy. He slowly inhaled, savoring her scent.
Mr. DeVine placed his open palm over her promised land and then lightly vibrated his hand. He kissed up and down each side of her “kitty kanyon” before running the tip of his tongue up her slit, making sure not to touch her sensitive sex button. Scott went down and probed his tongue into her glossy pink passageway before sucking and slurping on her lower lips.
“Don’t forget my toys,” Susan whispered.
Scott scoffed, “It’s not my first rodeo. Are you in a hurry? I’ll get there.”
He licked two fingers and slid one into her slit. This gave him a better idea of how warm and wet Susan’s pussy had become. He buried the finger deep into her pleasure palace. Upon exiting, he added the second finger and slowly went deep, in search of her G-spot. He felt a soft bump, so he added a bit of pressure. This caused Susan to flinch and buck her hips into his hand.
“Yeah, right there,” she mumbled.
He moved up the bed slightly, and he kissed Susan a few times before suckling on her left tit. When he curled his finger over her G-spot, Susan was moaning lightly and wiggling her hips an inch or two sideways.
She began panting for breath, and Scott knew she was close. He doubled down by turning up the speed and pressure of his hand, banging her and putting pressure on her G-spot.
“Yes! Right there,” she said. “Suck my clit!”
Scott circled her engorged pearl with the tip of his tongue before he started slurping and sucking. This caused Susan to begin playing with her tits, pinching and pulling her large nipples. The overwhelming stimulation was driving her crazy, causing her to moan in pleasure.
After about thirty seconds of sucking her clit, Scott could feel her inner walls begin to flutter and then tighten around his fingers as she climaxed. He did not stop, and shortly thereafter, Susan had another orgasm. He stopped sucking and looked up to see her slapping her tits, so he doubled down with the banging of her sex.
“You like it rough? You’re a freaky cougar, aren’t you?” he chuckled.
“Yes, I like it hard and fast,” she stammered as she rode out the wave from her second orgasm.
Scott started banging her sex as hard and as fast as he could with the two fingers on his left hand. He wondered what else he could do that she might enjoy that is considered rough play? Bingo! He had an idea.
His right hand suddenly grabbed her throat and squeezed, choking the forty-six-year-old vixen. He knew instantly that she was into it as she had a big smile. When they made eye contact, she nodded her head, “Yes.”
With his right hand around her throat, Scott had been banging her for close to a minute, so he changed tactics. His two fingers pressed hard on her G-spot and rubbed the sacred spot. Susan mumbled, “YES! Right there!”
Her legs shook, and she once again squeezed his fingers like a vise as the third started. Without any warning, Susan’s whole body shook, and she began squirting, blasting short pulses of sex liquid, soaking his left hand and the comforter.
He released her throat, and as she gasped for air, Susan said, “I’ve never done that before. Holy fuck, that was intense.”
Scott cuddled her in the big spoon position, saying not a word as her breathing returned to normal. After a couple of minutes, Susan said, “Let’s go to the kitchen for more water, come back here and change the bedding.”
The End – Chapter One.
