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Chuck Taylor’s Wake

Kategori: Genel

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Greetings all; in my stories my characters exist in my head, but there might be real life inspirations for some of them. Who knows?

I first introduced Kayli Taylor and her son Charlie to my readers in 100 Years in purgatory Ch 8. I decided to write a standalone story about them with a soap opera style plotline.

Kayli suffers from a case of Genetic Sexual Attraction to Charlie’s good looks and his perpetually hard cock, which she resisted acting upon until she surrendered to temptation and grasped the head of his hard cock one day.

He was an eighteen year old senior in high school at the time, which is when that kind of thing typically happens in the city of Literotica. In order to avoid doing something that might destroy the family Charlie decided to go to college as far away from home as possible and he hadn’t returned for five years.

Shortly after Charlie left for college Kayli’s very girly younger son Melvin came out to her and announced that he was in fact a girl.

The loss of both of his sons sent Kayli’s husband spiraling to his death five years later.

This story chronicles Charlie’s five day visit home after his father’s passing, in true soap opera ridiculousness.


Chuck Taylor was a Baker whose specialty was making doughnuts. Ironically he was a diabetic whose only pleasure in life was eating a hot doughnut from the first batch he cooked after they’d had the sugar glaze poured on them, and then he’d wash it down with a glass of cold milk. On August the second they’d tasted so good to him he’d had another one and another one until he’d eaten a dozen of them. By that time his blood sugar had risen to eight hundred and fifty milligrams per deciliter which put him in a coma before he died.

When he expired he left behind Kayli, his wife of twenty five years. Together they had a twenty one year old son named Charlie who’d recently graduated from college, and an eighteen year old daughter who was a rising senior in high school. Her name was Melissa, but it had been Melvin before she transitioned.

When Charlie received the news of his father’s death he took a week of bereavement leave from an internship he’d scored on a cruise ship that was deployed off the coast of Alaska. He hoped to make it home to Literotica in time to participate in his father’s wake, but when the uber driver dropped him off at his parent’s house three days later the vigil had already ended and there was nobody there.

He tried to make the best of the situation by drinking a couple of beers while waiting for his mother and sister to come home, but he nodded out on the couch.

Melissa came home around midnight, brushed her teeth, washed her face, freshened up her private parts, then turned in for the night without noticing that he was there. She was in bed naked with ear-buds in her ears when he woke up needing to take a leak. After he stumbled into the bathroom and drained the lizard, he went into his old bedroom stripped down to nothing and took a swan dive onto his bed.

Kayli was dropped off a short time later by the designated driver after sharing a couple bottles of wine with her girlfriends. She was buzzed but not too lit to do a quick check of the ground floor of her house before arming the security system. After getting undressed and following the same routine as Melissa, she went to peek in her room to make sure she was there.

She was about to go back to her bedroom when she noticed Charlie’s door was closed though she always kept it open. She assumed that Melissa had pulled it shut until she opened it and saw Charlie on his bed laid out like a starfish. After squealing like a schoolgirl before she realized it she called out his name.

When he opened one of his eyes and saw her, he grabbed the comforter and covered his cock as best as he could. She ignored his nakedness and sat on the edge of his bed, then proceeded to kiss each part of his face.

“Hi mom,” said Charlie as he smelled wine on her breath.

“Look at you,” she said smiling and staring at him lovingly. “You’re even more handsome than you were when you left home.” She then briefly looked at his broader shoulders and thicker chest and added, “You’ve really filled out,” and smirked to show her approval.

She then went on to ask him question after question, “How was your flight? What time did you get here? Why didn’t you call me? How long are you staying?”

He patiently answered her questions. “I got here around nine. I was bummed about missing dad’s wake and decided to have a couple of beers with his memory, just me and him. I’ll have to extend my bereavement leave, but I plan to stay five days.”

After he’d answered all of her questions she said, “I woke you up didn’t I? I’d better let you get back to sleep.”

After standing up she looked at him lovingly again. In the days since her husband’s death, more than anything she’d needed to be held by a man, but she wondered whether it was a good idea to lay down with Charlie? Muğla Escort She’d cuddled with him often when he was in high school, mostly because she had a crush on him. Their snuggling had revealed that he has a big cock, and the infatuation her discovery caused prompted her to try to see his morning wood. Once she finally saw it she had to touch it which she did.

He ignored his alarm clock one school day, so she went into his bedroom to wake him up. She found him lying on his back with his cock tenting his boxers. He was in a deep sleep and having a sexy dream at the time, so when the temptation to touch his cock overwhelmed her and she tapped it gently while saying wake-up he ignored her. After doing it a couple more times with no response from him she grasped the head of his hard cock and pumped it several times.

Her ministrations coincided with the action in his dream. He was plunging his cock into the warm wet pussy of Suzy Homemaker from across the street as Kayli pumped his cock more times than she’d intended, which inadvertently made him cum. In true soap opera style, in order to avoid further interaction with Kayli Charlie moved to another country to go to college. Technically he went to college in Alaska, but you get the point.

Kayli still felt the pull of her attraction to him, but under the circumstances she thought it would be ok to lay with him a little while then go to her room. “Cuddle with me,” she finally said softly.

Charlie remembered that incident too, and though he was older now with more dick control, he’d never snuggled with her while she was wearing so little and he was concerned that he’d get hard. Kayli noticed his hesitation and spoke to him softly and reassuringly saying, “I know what you’re thinking. It’ll be alright. I’ll lay on top of the cover. You can tuck your cock between your legs and wrap the comforter around your midsection before spooning with me.” She then bit her bottom lip and confessed, “I really need to be held.”

The guilt both of them felt about the past incident served to help them control themselves for a time, but the combination of Kayli’s thin nightgown and Charlie being bare chested allowed for so much contact between them til his cock soon came to life and sprang from between his legs. When Kayli felt it throb against her ass she apologized again for waking him up, before getting out of his bed.

When she got up Charlie was sure that he smelled the distinctly musky scent of her pussy. “See you in the morning,” she said before closing his door behind her.

Charlie lay awake for a long time after she left, but he refused to give in to his need and stroke his shaft while thinking about his mother. Eventually, somehow, some way, he was able to nod off. He was awakened the next morning by the chime from the alarm clock app on his cellphone. After taking a moment to completely wake-up he realized that his mother was standing in the doorway to his room wearing a duster.

“Morning sleepy head,” she said while smiling at him.

“Morning mom,” he replied.

Before leaving his room she turned to him and said, “Should I make you breakfast?”

He glanced at her a second before he responded saying, “Nah, I’ll eat cereal.”

She smiled at him warmly and said, “Okay, come on down stairs and eat with me and your sister when you get done in there.”

She was referring to the bathroom.

Kayli had never made a fuss about her or her kids hiding their bodies, and Charlie used to get out of bed and walked to the bathroom in front of her, even if he had morning wood, but he felt weird about getting up while he was buck naked, so he waited for her to leave the room before he went to the bathroom.

Kayli wanted to see the cock that had been pressed up against her ass last night, but she noticed that he was stalling before getting up, so she faked him out by giving the impression that she was leaving. No sooner than he stood up she turned around and got her wish; his cock was three quarters chubby and getting harder.

She gasped when she saw him naked, but she didn’t look away. Not only had he put on muscle his cock was even longer and noticeably thicker than it was the last time she saw it and it’d been big back then.

“Aw shit, sorry mom,” Charlie said over his shoulder before making a mad dash into the Jack and Jill bathroom he shared with his now eighteen year old sister. “Oops, shit, sorry,” he said a moment later, when he saw his sister Melissa standing at the sink buck naked while brushing her teeth. When she turned and saw him she screamed, “Charlie,” then took a couple of steps and hugged him with toothpaste in her mouth, and her toothbrush in her hand, never noticing that he was naked.

Charlie had only seen her face when they video called each other, so he hadn’t seen her body since their late father allowed her to transition after she turned sixteen. He was used to her being effeminate, but he didn’t know she looked like that. The hormones Muğla Escort Bayan she’d been taking for two years had caused her to blossom. She was curvy, but not fat, with small round titties and to his surprise somehow she looked feminine downstairs even though she still had a cock.

She was confused why he wasn’t hugging her back when she felt something poking her in her belly. She pulled away just enough to be able to look down where she saw the slit in the middle of the bulbous head of his cock staring back at her.

Charlie finally broke free from her embrace and he tried to get into the water closet as fast as he could.

He closed the door then leaned against it for a few seconds as he replayed the sight of her body in his head. “Damn, Melvin gon make a fine looking woman,” he said to himself. Then he tended to his aching nuts by pumping a load of cum into the toilet.


He’d dressed more modestly around his mom since the incident with her four years ago, opting to wear baggy basketball shorts around the house. But after the way they’d responded to seeing his cock, he said fuck it and wore a t-shirt and boxer briefs to breakfast. When he walked in there his sister Melissa was now wearing boy-shorts style panties with her tank top while sitting at the table texting. She shifted her eyes to look at him and smiled without raising her head.

His mom looked up at him as she was eating from her bowl of oatmeal and smiled as well. He was sure it wasn’t his imagination that she looked at his cock. His hardon was completely gone but his package was noticeable in the form-fitting underwear. While he was at the pantry getting a box of cereal his mom stared at him. “Look at you,” she said smiling. “You. Really. Have. Filled. Out. When did you start wearing that style of underwear? They’re cute, aren’t they Melissa?”

Melissa glanced at her brother for a couple of seconds and she spent the entire time looking at the bulge made by his dick. Then she bit her bottom lip and went back to texting.”

His mom and sister’s attention to his body stirred up his dick again and he felt another boner coming. He tried to will it down while he grabbed a bowl and the jug of milk, but he was only partly successful. By the time he sat at the table his mom was grinning at him again.

He ate a couple of spoonfuls of cereal while looking out the corner of his eyes at her, and she kept looking at him and biting her bottom lip. Finally he said, “What?”

She didn’t say anything right away, but after a few seconds she said, “I just can’t get over how much you’ve changed.”

Then she looked at his sister and said, “Hasn’t he Melissa?”

Melissa looked at him and giggled, then she said, “I think he stole a hot guys body.”

“Okay, okay,” he finally said. “You guys are embarrassing me.

“Its just that we like the man you’ve become,” said his mom. “Don’t we Melissa?”


For the next few hours they talked about their memories of Chuck and promised each other that they’d carry on with their lives the way they knew he’d want them to. All the while Charlie’s stole fleeting glances of his mom and sister. Melissa’s tiny boy shorts were giving her a wedgie, and they fit her pubic mound like a glove. He couldn’t believe how much her tucked cock made it look like she had a fat pussy.

His mom on the other hand was covered up, except for the fact that the gaps between the buttons on her duster would open as she moved, and he got lots of looks at her kinky pubic hair.

Eventually Charlie stopped fighting his erection and just let nature take its course. It turned out that his cock wasn’t rock hard all the time, in fact most of the time it was only chubby. He was a little surprised though at how often he caught his mom and sister checking it out.

Later that day they buried Charles Chuck Taylor and closed that chapter in their lives.


One year later.

During the year since Chuck’s death Kayli remained celibate, and stopped eating refined sugar. Melissa dealt with her grief by seeking attention from other men. She did so by becoming an exhibitionist. Charlie decided that life was short, and you should go places and do things, so he hired on with a cruise ship company and set out to see the world.


Kayli asked Charlie to come home to be with her and Melissa on the one year anniversary of Chuck’s death.

A month later Charlie’s Uber driver pulled into the parking lot of the Curly Bush Supper Club, and a few minutes later the hostess led him to his mother, his sister, his aunt and his mother’s girlfriend seated at a table near a window.

Charlie did a double-take at the changes in his mom’s and his sister’s appearance since the last time he saw them. His unassuming mom had colored the gray in her hair, and she was wearing make-up which was unusual for her. His sister Melissa had completely changed her appearance from looking like a passable girl to appearing Escort Muğla to be a CIS woman. She was wearing a wig that was fiery red, and hung down to her ass. There was a spike in her left nostril, and her red eye-shade matched her lipstick and hair. But the thing that was the most startling was Melissa’s facial resemblance to their mother. He knew she’d gotten some facial feminization surgery, but it was strange to see her looking so female.

Kayli hollered then called out his name as soon as she noticed him standing there. She then stood up and hugged him so tight until he gasped for air. When she released her hold on him she took his face in her hands and said, “Look at you, you look just like your daddy did when he was your age.” Then she kissed him full on the mouth.

There wasn’t anything unusual about her kissing him on his lips, she always kissed her kids like that. The thing was, this kiss wasn’t like the kisses moms give their children, it was more like the kisses wives and girlfriends give their men.

Charlie flinched and his body tensed when she slipped him some tongue. She then tilted her head to the side and kissed him so passionately until Sandy said, “Get a room you two.”

Seconds later Kayli broke the kiss and responded to her while still looking at Charlie. “We have one already,” she said, then she laid her head on his chest.

Charlie tried to play it off by laughing at Sandy’s wisecrack, but in reality he was shocked by what had just happened. His mom had never done anything like that to him before, but if he were honest it aroused him. Suddenly he was thinking about how good her soft curvy body felt underneath her dress, when he normally would have blocked it out the best he could. Now he was allowing himself to focus on the fact that It felt like she wasn’t wearing anything underneath it, and his cock had thickened automatically. He took a half step back as soon as he felt his dick get firm. He was sure his mom had felt it too, and she hadn’t moved a muscle.

“Harrumph,” went Kayli in Sandy’s direction as she sat back down. “Put your chair right here next to me honey,” she said to Charlie.

With his mother no longer standing in front of him his hard cock was laying on his left thigh and clearly visible. When Melissa saw it she sprang out of her seat and hugged him. “Sit in my chair big bro,” she said into his ear, “So Aunt Alice and Sandy won’t see that your dick is hard.”

“Thank you babygirl,” he replied as they embraced. The Estrogen she’d taken since she began her transition had caused her to grow b-cup sized breasts and made her skin feel like that of a CIS woman. He silently scolded himself as his dick got a little bit harder because of her.

When she felt his erection grow more rigid she ground her mound against it and teased him in a whispering voice. “What’s going on down there big bro?” she asked into his ear, then she giggled.

“Stop that,” he said louder than he intended to as he tried to quickly unhug her. She had on a loose fitting basketball jersey that showed off her toned arms and shoulders, and in his hurry he hiked it up in back.

“Watch out there now,” she said playfully. “I’m going commando, and you almost showed everybody my ass.” The other women at the table laughed when Charlie grimaced and said, “Oops.”

In spite of Melissa’s best efforts Sandy and Alice had seen the print Charlie’s cock had made along his left thigh, so when he turned toward his aunt Alice and tried to give her a polite hug, the sexy BBW said, “Don’t be shy honey,” as she pushed her thigh against his bulge for a second. She then touched his face and ran her tongue in a circle around her lips suggestively before saying out loud, “You really do need to get control of that big ole thing, cause there’s no way you can hide it when it gets hard.”

Charlie grimaced with embarrassment, then gave her a peck on her cheek as he wondered what the hell was with her dry-humping him, and what was the thing with her tongue about?

As soon as they broke their embrace his mom’s friend Sandy stood up and aggressively put her arms around his neck and pressed her round body against his suggestively. “Hello handsome,” she said without trying to hide her lust for him. “You sure have turned out to be a fine looking young man,” she said, then she nipped his ear with her teeth.

Charlie had been caught off guard by his mom, his sister, and his aunt Alice, but he was used to Sandy’s flirting, so he smiled and pressed his hard cock against her belly. By the look on her face she liked what she felt. After watching them for a moment his mother said, “Ahem, he’s spoken for.”

“Be that way then,” responded Sandy as she let go of him. As she sat down she said, “Woo lawd. Kayli that boy of yours sure has a big dick.”

All of the women laughed as they looked at Charlie lovingly.

He had nothing.

Once everyone simmered down Kayli looked at him again for a long moment before telling him that Sandy and Alice teased him because they love him.

Charlie gave a half smile with one side of his mouth.

Kayli saw that he was uncomfortable with the talk about his dick and moved on to a more appropriate conversation. “How long are you staying this time?” she asked.

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