The Matrons of Regal Bay Ch. 23

As for herself, she had friends who enjoyed a few other men outside of their marriages, and many of those were seeing men younger than themselves, by as much as half their age. Annie wasn't the jealous type, but she did sometimes wish she could go out and meet men, her own age or not. She just didn't have the courage, or maybe it was just that she was so content with having just one man in her life. First, her father, and then her husband, and now her son. Monogamy had always been her lifestyle. Maybe it was time to change things up, now that she was in her mid-forties.

"Invite him over," Annie said with a surrendering sigh. "Tell him that you're going to have your "girl-friend" stop buy and be waiting in the back, in the gazebo, for you. I'll take it from there, I guess. I'll figure something out."

"Thanks, Mom," Tim replied, hugging her nude body to his. "I think you'll have fun."

Annie pushed her son back and said in a serious tone, "I'd better, if you want to keep having any fun." With that said, Annie rolled from her bed and headed down the hallway towards the bathroom. Outside the window, the buzz of the weed-eater kicked up, and Tim wondered if Uncle Daniel had been spying on their conversation. Even as he wondered about that, Tim found his cell-phone in the back pocket of his discarded jeans. He had two calls to make, and he punched in the first number, still naked on his mother's bed.

"Hey, Ray! What's happening, Dude?" The second call would wait, since Tim knew that his aunt Charlotte, Daniel's wife, wouldn't be getting out of work for another half hour or so. He could already feel his cock twitching for his aunt's hot pussy.

***

Tim set the meeting between his mother and his friend up for the next afternoon. It was the only day of the week that both Ray and his mother would be off work at the same time, though Annie would be taking a personal day as it were.

"I told Ray to just go on back to the gazebo," Tim explained to his mother that morning over breakfast. "He's pretty excited, but I don't know if he'll go through with it."

Annie asked, "Are you sure this is a good idea, Tim? I mean, giving him the idea that you've been screwing older women and setting your friend up with me? And what if he recognizes me?"

"I don't think he's ever met you, Mom," Tim assured. "And if he did, that would have been years ago and I doubt he'd remember what you looked like anyhow." Tim put his empty plate and glass in the sink and then gave his mother a kiss. "Don't worry. Just have fun, okay? If it doesn't work out, no harm, right? You're just playing like you're a woman from the neighborhood with whom I've been secretly seeing, and you'd like to take care of my friend as a favor to me."

"I think I might be more anxious about this that he will be," she admitted as she followed her son through to the front door. "Are you sure you're okay with this?"

Tim again pulled his mother to him and kissed her. "Yes, Mom, I'm okay with it. And it'll be good for you to enjoy someone other than your own son, now won't it? Give you something you can talk about openly at work even, with all those other hot-to-trot honeys."

Annie shoved her son out the door playfully. "Just get to class. I'll see you later, tell you how much fun I had."

Tim waved her off and headed for his mother's car. They didn't have a second car, not after Tim's broke down. Annie refused to go to her family for a loan, so they would have to work it out for themselves until Tim had enough money saved up to buy another.

Annie did some house-work, dishes and laundry, to kill the hours before she was due to meet Ray in the backyard gazebo. When it was finally time, Annie headed out the backyard wearing jeans, a red blouse, and sandals. She brought with her a pitcher of fresh lemonade, made from a powdered mix of course, and two glasses. The sight of the rough wood gazebo stirred memories in her. Her husband and Tim had built it the first spring after they had moved into the North Bay home. It was a modest home in a modest neighborhood, with a large backyard that ran uphill. The homes were some of the oldest in Regal Bay, with the majority being of 1950's-style ranch homes. From the front yard, Annie's reminded her of the home from The Brady Bunch, though only on the one level.

Fresh-cut grass gave off a sweat aroma as she walked across the lawn. Two tall firs provided shade along the way, with the gazebo, butting up into the corner of the privacy fence that outlined her property, built beneath one. Inside, Annie set the pitcher and glasses on the table inside and dropped the curtains to provide just that much more privacy, though her neighbors to either side could still nib, given the slope of the yards. Annie thought that everyone would be at work, given that it was Monday, so she wasn't all that concerned.

"Hello?" Annie started and turned to find a tallish, dark-haired and bespectacled young man standing in the entryway to the gazebo.

"You must be Tim's friend," Annie said. "Do come in." Annie stepped back as the young man mounted the steps and entered. She moved to the bench that ran along the near wall, fronting the hard-wood table that took up part of the gazebo's interior.

"I'm Ray, Ray Dalton," he said, holding his hand out to her. Annie smiled and took it in hers, and then gently led him to a seat beside her on the bench. He was obviously very nervous, whether by her presence or the idea of what brought him to her in the first place.

"My name is Annie," she replied. "It's good to meet you, Ray." She paused, waiting for the awkwardness of the situation to pass before offering, "Why don't we get to know each other a little, okay?"

Ray nodded. "That'd be okay," he said.

Annie started. "My name is Annie, I was born and raised here in Regal Bay, I'm single, in my forties, and we'll leave it at that," she grinned, "I have a son who goes to college now, and I enjoy giving pleasure to young men, especially if they give me just as much pleasure in return." This last she added with a wide smile, and a subtle lick of her lips.

Ray took a deep breath. "I'm from Boise, originally, but my dad and I moved here after my mom died. Dad works on boats at the marina. I work at Fryers Electronics. I'm a service tech."

"That's nice. A suitable job for a young man," Annie grinned.

"I'm 21 now, a few months younger than Tim. He and I went to school together, did he tell you that?"

"He did," Annie smiled.

Ray grinned shyly and shook his head. "Oh, man! I can't believe I'm doing this," he muttered under his breath.

"And what is it that you are doing?" she asked after gently tilting his head up to meet his eyes with hers. "Or more specifically, what is it that you'd like to be doing? Me?"

"Tim said..." Ray started. Before he could say anything else, Annie leaned in and kissed him.

When their lips parted, she said, "I'm here for the same thing, Ray. I'm here for you." She picked up her lemonade and then handed him his. She raised her glass. "To having some fun, cheers," she toasted and then sipped, watching Ray do likewise. She set her glass back on the table and after a momentary pause looking at him, she said, "Take my shirt off, Ray."

Annie had on a red summer blouse, a shade darker than her curls. The prominence of her nipples poking at the fabric gave away the fact that she hadn't worn a bra, and her middle-aged b-cups hung low on her chest. Ray's eyes went to her chest in that moment and after a short pause, he reached out and began to unbutton her blouse, starting at the top and working down.

"Don't be shy," Annie soothed. "I want this as much as you do." Once completed with the buttons, Ray reached up to the lapels and brushed the blouse open. He took in the sight of her matronly breasts, with the hard, pale nipples jutting out from the center of pink areola excitedly. Annie rolled her shoulders back, bringing her breasts up slightly as her blouse slipped from her shoulders. Ray reached out and stroked his fingers lightly across the bottoms and sides of her breasts as she pulled her arms free and let the blouse fall to the deck behind her.

Ray was getting bolder by the moment and let his hands fall to her waist, where he tugged at her jeans and popped the snap. He found the zipper and pulled, and Annie sucked in her slight belly to give him a better angle to unzip her. The top of her white panties showed beneath her naval, and Ray's eyes took that new sight in as well.

With Ray taking her exposed flesh in with his eyes, Annie reached out and took hold of his Seahawks t-shirt. "Lift your arms," she had to tell him, and when he did, she pulled the shirt up and off. Now both were topless, sitting beside each other on the bench. She took in his naked torso, and though he wasn't well-built, he was no slouch either. Just a nice, average looking young man.

"Stand up, Ray," she told him, and again he responded obediently. Standing before her, Annie began to unfasten his jeans, starting with the thick Cowboy-style belt and buckle he wore. The denim jeans were dark blue, as if new, and she had to tug hard to get them to start down his thighs. When she did, his underwear went with them, and Ray's cock, still somewhat flaccid from his obvious anxiety, hung from the dark tangle of pubic hair, above a large set of balls any mother could be proud of. It was awkward for the next few moments, as Annie had to help pull Ray's boots off while struggling with the jeans. All the while, his cock hung just inches from her face.

Once Ray had finally been stripped, Annie stood up and told him, "Your turn to strip me," which Ray did from his knees. She noticed that once her red-haired pubic triangle came into his view, just inches from his own face, his cock began to stiffen greatly.

Again, Annie sensed her need to be in control to help him along. "Sit down, on the table," she told him, and again Ray moved to obey. His grin was locked on his face when he settled onto the hard-wood table top. Annie sat on the bench between his parted thighs and reached between to take hold of his cock. She grinned up and said, "I hope you enjoy this," before taking his purpled knob between her lips. She began to jack his shaft while tonguing his knob and rolling his balls in her hand, and Ray responded with moans of happiness only young men could make, when their dicks were in a warm mouth.

Inside Annie's mouth, Ray's cock grew thicker and longer, until it was a good nine inches long and so thick her fingers barely touched when wrapped around it. Panting, she lifted her mouth and said, "You've got a fabulous cock, Ray. I don't know why you can't find a girl to enjoy it." She returned to sucking him, enjoying herself as much as he was enjoying her.

It wasn't long before she tasted his tart pre-cum on her tongue, pulled from his tube by her jacking fingers. She reluctantly lifted away and told him, "I need this inside me." Annie quickly moved onto the table, straddling his waist. With his cock still in hand, she lowered herself onto him, accepting his thick manhood into her heated sex with a single plunge.

"Aaaahhh!" she moaned as Ray's cock filled her.

"Oooohhh!" he moaned into her chest. He wrapped his arms around her as she began to bounce on his lap. He'd not had sex in many months and the feel of Annie's pussy wrapped around his dick was overwhelming. "Oooohhh, Anniieeeeee!" he grunted just a minute in, and his cock began to pulse and spit. "Aaaahhhh!"

"Yes, yes! Cum for me! Cum for me!" Annie could feel Ray's cock throbbing even before she heard his groans of release. Her belly was already warming from his spitting semen as she accepted his seed high inside her womb. She continued to ride his pulsing cock, tightening her pussy hole around his shaft as she milked his cream from his balls. His fingers dug into her butt and she slowed, settling onto his spent penis a few minutes later. She could feel him softening and she rolled her hips, enjoying the sensations of stirring his cum inside her with his dick. It wasn't long, however, before he slipped out of her.

"I'm so sorry, I couldn't help myself," Ray apologized.

Annie touched her finger to his mouth and shushed him. "I understand. It happens, especially if you've not had any in a while, or when you're with someone for the first time." She pulled his mouth to hers and kissed him. At first, it was warm and loving, but quickly it began to grow more heated as Annie stuffed her tongue into his mouth, and Ray did likewise. It wasn't long before she felt his cock twitch to life beneath her ass.

Annie broke off her kiss and said, "I want you back inside me Ray." She climbed from atop him to lay beside him on the table top. Ray was quick to pick up what she wanted, and even though his cock was still a limp, damp slap hanging from his crotch, he leaped from the table and took up position between her parted knees.

Annie pulled her knees back and said, "Stick in in me, Ray," and her young lover pressed his limp cock against her slick slot. He moved the knob up and down, smearing his spent semen that leaked out across her clit and all over the pink labia. Her hole opened and he was then able to pop the knob back inside. With a little work, he was able to push enough of his cock into her so that he could let go.

Annie could feel Ray's cock growing within her and it sent sensations up and down her spine she'd not felt in years. Ray had bent over and was sucking on her nipples as his cock slowly slithered deeper into her. "Aaaahhh, so nice," she purred while stroking his back and head. He pushed a little and another inch of dick entered her. It wouldn't be long, she knew, before he was pounding her. This time, with his initial load already planted deep within her providing lubrication, he would last so much longer, and give her so much more pleasure. It was turning out very much like the first time Tim had taken her, in very much the exact location. It was however a different table Ray was about to fuck her on. And Tim's first load had gone down her throat.

"Fuck me, Ray," Annie purred as she felt his hips begin to move, pushing the fat, stiff cock in and out of her with short strokes. Ray again obliged her, and pulled back to drive hard and deep, repeatedly giving her the full length of his rejuvenated manhood. "Oooohhh, yes! Yes! Fuck me, Ray! Fuck my old pussy!"

Ray was panting heavily, poised above her. His hands were planted into the table top to either side of her shoulders as his hips slammed time and again into her crotch. His cock seemed that much longer and thicker now, and Annie felt her orgasm rapidly build. "Oooohhh, yeeeesssssss!" she hissed as she climaxed. Ray's cock relentlessly pistoned within her, forcing her to an intense climax that held her at her peak just a bit longer. "Oooooohhhhhhhh!" she howled as her orgasm exploded. Her hips jumped, meeting Ray's thrusts. His cock pounded her cervix. Her clit was slammed by his pubic bone, with jolts of pain adding to her intense orgasm.

"Oooohhh, fuck yes!" she screamed as she sat up and took a tight hold of Ray around the shoulders. His cock was wedged high inside her and suddenly began to pulse wildly. She was trembling in his arms as he held her, her climax continuing as Ray began to refill her with hot man-seed. She pulled his mouth to hers and slammed her tongue as deep into his throat as she could, moaning at the same time in concert with his own howls of release. It had been a long time since she'd had such an intense orgasm. Annie felt a pang of regret that she'd experienced it with her son's friend, and not with Tim. It was a fleeting regret, as Ray's cock continued to pulse within her, and yet remained hard and stiff.

"Oooohhh, yes! Fuck me again! Fuck me again!" Annie panted. She pushed her hips against him, fucking back at him, until Ray laid her on the table again and started working his cock through her battered pussy with deep, smooth strokes. Annie found herself swooning, panting and huffing as Ray pounded her with his cock again and again. Her head hung from the edge of the table and her limbs had fallen limp. Ray held her feet to his shoulders as he drove into her, even kissing her toes from time to time. Her tits bounced on her chest, unattended to, and Annie realized that a second lover would be welcome then. She licked her lips, imagining her son's cock thrusting down her throat while Ray's worked her pussy over. Tim would be man-handling her tits even, pulling and twisting her nipples and sending jolts of painful pleasures through her, until she was screaming through another intense orgasm. Yes, she would bring it up with Tim, that night. It was something she now wanted, to be taken by two young men.

Annie lost track of how long she lay there, being fucked hard by her new young lover. She had climaxed over and over, and when Ray had slowed his rutting and slipped out of her, she felt a warm gush of semen roll out of her ravaged hole. He'd cum inside her again, a third time, and was now totally spent. So was she. So much so that she didn't realize that Ray had dressed until he leaned over her and kissed her sweetly.

"Thank you, Annie," he whispered. "That was the best sex I have ever had in my life."

Annie reached up and stroked his face. With an exhausted smile, she replied, "That was damned good for me, too." Again, Ray kissed her, and then was moving away. He was through the gazebo archway before she could prop herself up on her elbows. It was dark by then, and she gave the backyard a scanning look. Yes, she imagined that any of her neighbors could have been watching, given the fact that the shades were moving easily in the light breeze. "I guess I should have tied them off," she sighed as she slipped off the table and gathered up her clothes. She walked naked, and dripping, across the yard to the back door. Once inside, she headed for the bathroom and a much-needed shower before collapsing in her bed.

***

"Man, you didn't tell me how hot she was!" Ray told Tim over beers at the Fish Heads, one of the boardwalk bars favored by locals over the college crowd. It was a straight-up drinking bar, with a pool table in the back, shuffleboard along the hallway wall leading to the bathrooms, and dozens of small tables. Tim and Ray sat towards the end of the bar, each with a cold can of Pabst Blue Ribbon in hand and a dish of peanuts between them.

"I told you. Older women are so much better fucks than girls are age. They'll do just about anything you want." Tim grinned and gulped some beer.

"And men, do I like red-heads! Her body sucked three loads out of my balls, did I tell you?" Ray was grinning wide, proud of himself. He looked towards Tim and saw something else entirely.

"A red-head?" Tim gasped. "You fucked a red-head?"

"Yeah. You set me up with her," Ray responded, now with a bit of concern in his voice. "Why?"

"Man, my girl-friend, Hannah, she's a blonde! Not a red-head!" Tim lied.

"Hannah? This woman's name was Annie, not Hannah," Ray said.

"Annie!" With a stunned expression, Tim gasped, "Oh, my god, Dude! That wasn't my girl-friend you fucked! That was my mom! My mom's a red-head, and her name's Annie! You fucked my mom, Ray!"

"Oh, shit! Dude!" Ray gasped. He was visibly upset, to the point of throwing up even.

After a lengthy pause for effect, Tim started to laugh. He gave Ray a soft punch to the shoulder and admitted, "There's no Hannah, Dude. I was just fucking with you." He took drink of his beer, trying not to choke as he watched his friend try to come to terms with what he was being told.

"Are you telling me that you set me up," Ray hissed, trying to keep his voice down, "to fuck your mother?"

Tim leaned closer and told him, "Yes, I did. And you know what else? She is my girl-friend. I've been sleeping with my own mom, Dude!" Tim raised his beer and finished it off. "Bartender! Another round for my friend and I!"