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The Courting of Anita Caples

The Courting of Anita Caples

by Schaa
19 min read
4.4 (12000 views)
mothersonthreesomeswingingdoggie
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The Courting of Anita Caples

Chapter 01

Anita Caples stood naked in front of her full-length dressing mirror. She turned slowly, critically examining the 54-year-old woman gazing back at her. She thought she looked old and fat. Her breasts, once full and pendulous in her youth, now sagged.

If they get any bigger, she thought, they will have to add a letter to the alphabet for her to find a bra size that fits.

Her abdomen was decidedly round, her hips were broad, and her butt had a decided oval shape.

Lord, what had happened to my body?

Anita had never been a small girl. Throughout her life, she struggled with her weight. When her husband Ed was alive, they would go for walks together and occasionally jog. Her heart ached as she recalled her loss.

Next week, five years after Ed's death, she was marrying Carl Dreisson, a decent enough guy. They met two years ago. At first, she was distant. She was still grieving Ed. Eventually, after much encouragement from her son and friends, she agreed to go out with him.

Somehow, after two years of dating and lackluster sex, she agreed to marry him. She couldn't recall him asking. At some point, it was assumed.

A profound sadness filled her heart. Life was so unjust. Ed passed away from a massive heart attack just as they had reached the sweet spot of their lives.

Their twenty-five-year-old son Allen was offered a major promotion. He moved across the country to accept a good-paying job and start his life.

While her husband was thrilled to see their son thrive in corporate life, Anita felt devastated as she watched her only child leave the nest. In some ways, her bond with her son was stronger than the one she shared with her husband.

Ed was devoted to his career, leaving Anita to raise their son. They bonded over camping trips and shared a passion for sports. She was assigned the task of teaching sex education. Those awkward lessons created an unusually close bond between mother and son. They could and did discuss the intimate details of their lives.

Shortly after Allen moved away, Ed had a mild heart attack. It caused him to review his life priorities. He realized that, as empty nesters, they should explore the next chapter of their lives.

Their sex life took a significant upswing. They embarked on an exploration of their sexuality. They started to delve into the bedroom fantasies that all couples talk about, but most never do.

They eschewed the marital bed. The floor in front of the TV was one of their hot spots. They would play porn on their 75" flat screen and pretend they were in the scene with the actors.

They assembled an extensive array of sex toys. Their favorites were the ones where they could simulate threesome sex with a vibrating dildo in Anita's pussy while she sucked Ed's dick.

They became more adventurous and discovered hidden spots on their walks and jogs in the nearby park to make love.

Anita smiled wanly as she recalled when a man walking his dog discovered them in flagrante delicto. In fact, it was the dog that caught them. Her smile widened as she remembered Ed's yelp of surprise when the dog's cold, wet nose touched his bare backside. The owner followed the dog.

She and Ed were stark naked in the woods and doing it doggy style. Anita reached back and touched her ass. They were really into it that day. Ed had spanked her bare ass so hard and so often, it took a few days before she could sit comfortably.

She giggled as she recalled the startled man mumbling apologies and backing away. She and Ed kept fucking after the man left. They naughtily suggested that they should have invited him to join them. That incident led to pillow talk about their recurring fantasies of bringing another person into their bed. It was all fantasy until they decided to take a lifestyle cruise.

They surfed the internet in search of a site where they could connect with others and indulge their fantasies. They came across a website promoting adult cruises that offer a unique experience with like-minded individuals. The cruises featured clothing-optional areas, theme nights, and other adult activities.

She smiled as she recalled meeting the Andersons on that 7-day Caribbean cruise. They met on the bus to the embarkation dock.

Julie Anderson was a bubbly 47-year-old redhead. Anita recalled being jealous of the slender, big-tit, green-eyed vixen.

Julie took charge. She instructed the husbands, Tom and Ed, to sit together while the girls got to know each other. Anita smiled, remembering how annoyed she used to be at the incessant chatter of this attractive pre-senior. Little did she know that the four of them would become fast friends and lovers.

While they were on the cruise, they had their first experience with partner swapping. Anita recalled the terrifying moment when the first cock other than her husband's entered her pussy. To add to the moment, Julie was naked in the bed next to her, riding Ed's cock.

Toward the end of the cruise, they attended their first swapping party. By this time, Anita considered herself a connoisseur of cocks, having had two other than Ed's.

After the cruise, the four of them regularly swapped partners. During those halcyon years, the two couples explored all aspects of their sexuality.

In addition to same-room sex, where they shared a bed with their spouses, they would go out to an event and swap partners for the night. Julie would spend the night with Ed, and Anita went home with Tom. It added another level to their relationship.

Tom and Ed tried sucking each other's cocks. They decided that in the heat of the moment, it was okay, but they didn't want a constant diet of cocksucking.

Julie and Anita, on the other hand, discovered they enjoyed eating each other's pussy as much as they enjoyed fucking each other's husbands! Primarily, as the men grew older and experienced some performance issues, watching the women engage in intimate moments became a regular feature of their meetings.

Tears streamed down her face as she flashed back to that terrible phone call from Tom. He and Ed were playing golf when Ed had a massive heart attack. She was ashamed that those days after his death were an emotional blur. Julie and Tom took charge until her son arrived from the West Coast.

Even after Allen arrived, Julie was always there. She and Allen bonded as they made the arrangements, answered the calls, and supported her through the hardest thing she had ever done. She watched her one true love being buried.

In the days following the funeral, Julie had practically moved in. She cooked, cleaned, cajoled, and finally, in exasperation, threatened as she tried to pull her longtime friend and lover from despair.

However, her grown son, her 30-year-old only child, finally brought her out of the depths.

Anita had begun sleeping on the couch. She could not bear to sleep in her marital bed because the sense of loss there was too intense.

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Initially, Allen pleaded with her to go to bed. When she wouldn't, he began sleeping on the couch with her to comfort her. She recalled his body warmth was like a balm that soothed her emotional hurts.

There were some awkward moments. Like the time she woke up sleeping spoon fashion with him, his large hand cupping her breast. She was gobsmacked. Her astonishment increased when she realized her short sleepshirt had risen around her waist. The steel rod she felt between the cheeks of her bare ass was her son's cock slipping through the slit in his boxers.

She covered his hand with hers and lay there for several moments, comforted by the familiarity. Anita pressed back and rotated her behind against her son's cock. It was at once comforting and erotic feeling his shaft slide between her ass cheeks.

She briefly considered doing the unthinkable. All she had to do was raise one leg, and Allen's cock would slide into his mother's pussy. Why not? This man loved her as much, and in some ways more, than her deceased husband.

She managed to extract herself from his erotic embrace without waking him. She loved her son and craved intimacy but feared the loss of the maternal relationship.

Later, standing in the kitchen making coffee, she felt a tingle between her legs as she recalled the incident. He was so like his father. They were both tall, husky men, standing at around 6'5" and weighing 240 pounds. She idly wondered if his cock matched his father's cock.

The aftermath was awkward.

"By the way, I enjoyed snuggling with you last night. It reminded me of your father. We slept like that a lot."

Anita noticed her son's unease.

"Uh...sure, Mom! Uh... look... let me apologize for... uh...!

Anita reached across the table and caressed her son's hand.

"Look, baby! No apology is necessary! Our intimate cuddling made this old woman feel good!"

"You enjoyed it? I mean...I don't know what I mean!"

"Baby, I'm your mother. There are certain things we probably shouldn't do. But a tit squeeze and dry humping while we are snuggling and sleeping is not going to cause a scandal."

Anita recalled grinning wickedly at her red-faced son. "Besides, I won't tell if you don't."

Still staring at herself in the mirror, Anita's other hand squeezed her full pendulous breast as she fingered herself. She could hear the wet sloshing of her pussy.

Mother and son slept like that for all of Allen's visits in the following years, eschewing the marital bed. They agreed that sleeping in the same bed as Ed crossed a line they didn't want to cross. It suggested a semi-permanent relationship they weren't sure they wanted. However, those intimate nights on the sofa where they were physical with each other but didn't have sex helped the mother and son deal with their grief.

Before he flew home after the funeral, there were nights when their nocturnal makeouts came close to penetration. One night they were dry humping when her son's cock slipped between her thighs and slid between her labia.

Anita was prepared to take it to the next level. She raised her leg, grasped her son's cock, and was going to slip it into her creaming pussy. Allen stopped her, reasoning that it might be hard to stop once they started.

Later that year, she did what she once thought was unthinkable. However, that night marked a turning point in her road to recovery.

Before Ed's death, she and Julie used to have long intimate conversations about their husband's cocks and sexual prowess. It always happened over a bottle of wine while their men were away.

Julie was hooked on Anita's husband, Ed's cock. She said it was the largest she ever had. Julie would sip her wine and shiver as memories of her best friend's husband fucking her flooded her mind.

Anita, on the other hand, enjoyed Julie's husband Tom's cock as a nice change of pace. At 6 1/2 inches, he was two inches smaller than her Ed. However, he had tremendous staying power. Anita could not count the times she and Tom cuddled watching Julie and Ed in one of their marathon fucking sessions. They teased them about being closet porn stars.

Ed was a one-and-done guy. His magnificent tool took her to unimaginable heights. However, once he arrived, he was rarely able to perform again that night. It usually fell to Tom to finish her off. She shivered as she recalled him switching between her and Julie. He could fuck them both senseless and still not cum.

Anita watched herself in the mirror as her hand trailed to her neatly trimmed, greying pubic hair. She touched herself as she remembered seeing the bulge in her son's boxers as he sidled into the breakfast nook that morning after they nearly fucked on the sofa. He was trying to hide his hard-on and his embarrassment.

"You understand, Momma, it's not because I don't want to have sex with you. It's been a fantasy of mine since I was a teenager with so many hormones they were running out of my nose. But what happens afterward?"

"Afterward, I go clean up. Maybe we shower together," Anita said, teasing her son semi-seriously.

"Momma," he said in mock outrage, " you're being bad!"

"When your mother is being bad, she is very good at it!"

It was the first of many times that she thought of Allen as her grown son and the other man in her life. The relationship was platonic initially. They were more affectionate, and the kisses on the cheek evolved into quick pecks on the lips.

They were two adults helping each other get through the emotionally draining grieving process and becoming more intimate as they did. Allen arranged his work travel and vacation schedule so that, in addition to Thanksgiving and Christmas, he was home two to three times a year. She and her son's level of intimacy grew with each visit.

Anita experienced a petite orgasm as she watched herself in the mirror. She was not surprised that during these masturbatory interludes, it was her son's face she saw, not Ed's anymore. He was still a warm, comfortable memory, but her son was her fantasy lover.

It was not Tom Anderson. The three of them still had sexual interludes, though as they aged, the intensity waned. It was definitely not the staid, comfortable, colorless Carl.

Why am I marrying him?

She answered her own question

. Because I'm lonely, and no one else wants a fat 54-year-old overweight widow!

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The ongoing threesomes with Julie and Tom were satisfying. The frequency dropped from their weekly session to two to three times a month. Tom still did yeoman's duty fucking her and Julie. However, even Tom, with all of his sexual stamina, couldn't replace having her own man.

She heard the shower in the hall bathroom come on. That would be her son getting ready for her "bachelorette party." The party was Julie's idea. Her rationale was that every woman needed one night to celebrate or commiserate before her wedding.

She and Allen were having dinner with Julie and her husband. There would be dancing and maybe a little too much wine. Anita wanted to let her hair down one last time before getting married.

Anita entered the en suite bathroom, adjusted the water temperature, and stepped in. The hot water streamed across her large breasts. She flinched as she realized her nipples were still sensitive from masturbating and pulling on them. Steam wafted about her as she retrieved the loofah from the tray and began to lather up.

She lingered over her nipples, moving the loofah in a circular fashion over each nipple. Her hips pumped involuntarily as the sensation wracked her body.

She recalled a Christmas two years ago when Allen came home. It was just before she met Carl. He was downtrodden because he and his longtime girlfriend broke up.

"What happened, baby?"

"Momma, she said I was distracted when I made love to her. She said there must be someone else."

"Sweetie, is there?"

Anita and her son sat hip-to-hip in the breakfast nook, partially facing each other. Her breast pressed lightly against his shoulder, and her hand rested familiarly on his thigh. Allen was distraught, and she was trying to comfort him.

Allen was in his boxers, and she wore an old sleeveless V-neck spaghetti-strap sleepshirt. She had gained weight, and instead of being above the knee, the length draped to mid-thigh.

Since Ed's death, they have been more casual in their dress. They dressed not as mother and son but as intimate friends.

A dispassionate observer would have noticed that they were more handsy. Allen's hand rested on his mother's ass cheek as they stood at the kitchen counter filling their coffee cups, and discussing the events of the coming day became commonplace.

Anita no longer wore a robe to cover her sleep shirt. Walking around the house in her bra and panties became common as she dressed for the day. Also, seeing Allen's morning wood bulging in his boxers was distracting but not embarrassing.

"Mom, I don't understand," Allen cried, tears streaming down his face. "Why can't I keep a girlfriend? I'm not rich. However, I do alright. I'm reasonably good-looking. What is wrong with me?"

Anita embraced her son, pulling his head to her bosom. She stroked the back of his head, trying to comfort him. From childhood, he had always sought comfort by lying on his mother's full bosom, and it was no different now.

His hot tears dripped onto her breasts as she stroked his head. He was her only child. She would always be there for him.

Anita recalled letting him nurse until he was almost eight. It helped to soothe him after the travails of elementary school. She would bare her breast, take him in her lap, and let him munch on a cookie as he nursed and told her about his day at school.

In her distress with her son's crying, she reverted to something that had worked in those early years. She freed one of her arms and slipped off the strap on her sleeveless silk nightgown.

"There, there! Mommy will always be here. Go ahead and nurse. It'll calm you down like it used to. It'll be our secret."

"Momma, I'm 30! I can't do that. It's...it's wrong!"

She took her tit in her hand and offered it to him. "You'll never be too old to be momma's baby! And nothing a mother does to ease her baby's sadness is wrong."

She offered her teat again, and her son, reluctantly at first, took it in his mouth and began suckling. Anita cooed as she caressed his head, just as she had back in the day when he was overwhelmed by the everyday stresses of going to school.

Allen moaned as he suckled while holding his mother's massive breast in his hand. The other hand dropped and caressed her behind as he did. However, he was no longer a prepubescent boy; he was a sexually active man. The eroticism of nursing the teat of the most important woman in his life was too much. Inevitably, his cock hardened and poked out of his boxers.

Privately, he knew his girlfriend had been right. He was distracted while they made love. He thought of his mother, wishing it were her moaning beneath him. He deeply regretted not having sex with his mother the night he woke up with his shaft between her labia.

They both realized that they were more than just mother and son. They were lovers with unconsummated love. At a visceral level, they knew they would eventually have sex.

They were inching toward it, trying to reconcile the intensity of maternal love with the intimacy of sex. If they could control those emotions, the sex would be epic. If they couldn't, it would consume them.

Several times a year, he came home to visit his mother and sleep on the couch with her. They cuddled while watching old movies. Allen would squeeze her breast, and his cock poked through the slit in his boxers and rested between the cheeks of his mother's ass.

Their relationship evolved to the point that they would routinely dry hump. Once while they lay locked in an intimate embrace dry humping, Allen's cock, lubricated by his precum, slid over her anus, and his cockhead slid between her engorged cunt lips while his shaft rubbed her anus.

"Oh my God," Anita exclaimed, pressing back to increase the pressure.

"I love you, Momma."

"I love you too, baby. But it's my turn to say we mustn't have sex. I want to, but I'm frightened of what making love to you would do to our relationship. I don't want to gain a lover and lose a son."

In the five years since Ed's death, it was the closest they came to having sex. They both wanted it but feared it would damage their close relationship.

Sitting in the breakfast nook, letting her son suckle, Anita glanced down and saw his donkey dick poking through the opening in his boxers.

So like his father, she thought!

Her son stopped suckling, and his lips rested on her areola just above her nipple. She sighed when he squeezed her tit and then kissed her areola.

"How can I be so strong and still be like a baby with you?"

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