Cinderfella Pt. 01

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A teen boy lives with his stepmother and stepsisters.
16.1k words
4.73
87.9k
135

Part 1 of the 3 part series

Updated 06/07/2023
Created 05/08/2016
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RonCabo
RonCabo
2,045 Followers

Once upon a time, there was a family. The mother passed away at a young age, and the father was left to raise their son. A couple of years later, the father remarried and the son suddenly had a stepmother and two stepsisters. They became one happy family until many years later when the father tragically passed away and the son was left to live with his step-family . . .

* * *

Despite the late hour, the light was still on so Ella entered her twin sister, Emma's, bedroom. The latter was sitting with bare legs folded in her bed reading, clad only in the silky-looking short shorts and tank top she slept in. The former was dressed similarly; not because they were identical twins and dressed alike, which they did not, but because she happened to like to sleep in the same kind of bed clothes.

"Glad you're still up," Ella said, climbing on the bed and sitting in the same position, but facing her sister. They're legs actually touched.

"It's only 10:30," Emma pointed out.

"Rest of the house is quiet. Guess mom and Jamie went to bed."

Emma merely shrugged.

"Anyway, tomorrow is Jamie's eighteenth birthday," Ella reminded, placing her hand caressingly on her twenty-one-year-old sister's thigh. "We should do something special."

"Yeah, I've been thinking about that also, but I haven't come up with anything. You?" Emma noticed her sister's pointed nipples imprinting through the material of her top.

"Nah. He's just such an easy-going guy. It's hard to know what would be special to him." She rubbed her hand up nearly to her sister's crotch.

At that moment, their mother walked in and was not surprised to see Ella's hand seemingly about to touch Emma's pussy. Smirking, she remarked, "What are you two horny bitches doing?"

Both girls looked up to see their mother, Sally, dressed in a revealing, low-cut, knee-length negligee.

"Wow! Don't you look hot?" Emma observed. "Expecting someone in your bedroom tonight?" She teased.

"Never know who I might meet in my dreams," Sally shot back.

"A woman as attractive as you ought to be able to find a good-looking man," Ella said.

"Oh, I can. Just haven't come across one who's not an asshole."

"Yeah, I know what you mean," Emma agreed. "The guys at our college are just like that."

It was basically the same conversation the three females frequently had.

"So, we're you two about to get into it?" Sally asked, knowing they frequently enjoyed each other's bodies.

"Actually, we were discussing what we could do special for Jamie's birthday tomorrow," Ella told their mother.

"Well, that's very nice of you. Not many girls who would be so considerate of their stepbrother."

"He's a good kid," Ella noted. "He puts up with three bitchy women—"

"Speak for yourself," Emma threw in, smirking.

"What I mean is," Ella clarified, "that it must be hard for him to be stuck having to live with his stepmother and stepsisters since his father died a year ago and he has no one else."

"You're right," Emma agreed. "Any ideas, mom?"

Sally shrugged. "Not for anything special. I bought him a few things . . . what are you doing?"

Emma had reached out to tweak her mom's nipple indenting the thin nylon of her negligee. "You have the nicest tits."

"You girls need to find some guys and get laid," their mother said.

"So, do you."

"Like I said, they're all assholes."

"We said the same," Emma noted.

"And until then," Ella said, "we're content with you." And with that, she pulled her mother to her and kissed her in the most un-family-like manner.

Sally grinned and kissed back, while Emma watched with a big grin. She then started tugging on the tops of the others, causing her mom and sister to ease back and remove garments. Both Sally and Ella totally stripped, while Emma shed only her top, and then decided to go all the way also. Ella had pushed Sally onto her back, and Emma didn't hesitate to spread her mom's legs. A second later, Emma's tongue was taking swipes on her mother's pussy. Sally pulled Ella back to resume their kissing.

The three had begun these lesbian sessions not long after Sally's husband and the twins' stepfather, James, Sr., had passed away a little over a year ago. The girls had been masturbating each other for a few years and it gradually escalated from just fingers on pussies to tongues and kissing. After the tragedy, Ella and Emma had constantly attempted to cheer up their mother, and it wasn't until they caught Sally masturbating one night and "helped" her that they started regularly pleasuring each other. All three dated men when the right one came along, which wasn't often enough for them—or maybe they were just too selective—and didn't really consider themselves lesbians. They didn't do it with any other females.

Emma was the most accomplished at cunnilingus, while Ella was the better kisser. Sally was pretty good at both, but hadn't had as much practice as her daughters, having just started doing girls when her daughters started doing her. She was content to just let them work on her. Emma licked and jabbed her tongue as far inside her mom's hole as she could, and flicked the tip of her tongue against Sally's clit until she came fairly quickly.

Emma then eased up to suck her parent's nipple. When Ella took up the other nipple, it always reminded Sally of when they were infants and both nursed at the same time. She absolutely loved it. Emma wanted a turn kissing her mother, and so she did.

After a few minutes, Sally and Emma swapped places so mom could lick daughter. Ella was content to watch and play with her sister's tits, as well as fondle her mother's ass and pussy with her fingers. For Emma, licking was as stimulating as being licked, and with the added attention from Ella, who was now sucking Emma's nipples, the combination had Emma reaching orgasm in short order.

Emma and Sally switched back to their original positions so the former could perform cunnilingus on her mother again. Sally then called for Ella to straddle her face so mom could tongue her. Emma's technique this time was to use both tongue and fingers, inserting two into her mother's hole and finger-fucking her while licking her clit. Sally pulled on Ella's pussy lips with her lips.

Emma drove a third finger inside her mother and used her thumb to rub her clit, and this time, Sally had a more powerful climax. In fact, she trembled so much, Ella had to move aside. Once mom's orgasm subsided, it was Ella's turn, so Sally arranged her daughter on her back, spread her legs, got on her stomach and went to work on Ella.

Like her sister had done, Emma played with her mom's ass and Ella's tits. When Ella was getting close, she pulled Sally up to kiss her and urged,"Em, please finish me off," which her sister was only too willing to do. Ella then had an explosive orgasm and nearly head-locked her sister when her pussy became too sensitive to be touched anymore.

"Let Emma go," Sally whispered in Ella's ear.

"Oh, sorry."

Once they could all breathe again, they all laughed.

"Well, if you two think of anything special for Jamie, let me know," Sally said, slipping her nightgown back on. She kissed her daughters and then left.

"That was so much fun," Ella remarked, putting her clothes back on.

"Yeah," Emma agreed. "I wonder what Jamie would think about this?"

"He turns eighteen tomorrow. Maybe the something special would be to invite him to watch."

"Ooh, that's wicked. Not sure I'm ready for that, though."

Well, then, keep thinking."

* * *

It was the raging hard-on that awoke Jamie on his eighteenth birthday; typical for him to awaken with one, typical for it to awaken him. Of course, living with a gorgeous stepmother and equally as ravishing twin stepsisters, it was no wonder; particularly since they were not shy about how they dressed around him. And he was not above spying on them when he could. At one time or another he had seen each of them in various stages of dress, including on a few rare occasions, completely nude. Just recalling those images in his mind gave him an erection, or in this case, maintain the one he had.

Jamie's few friends thought it was unfortunate that he was stuck living with his stepmother and stepsisters since his dad had died of a heart attack over a year ago. His mom had lost her battle with cancer when he was very young and both of his parents had been an only child, and both sets of grandparents were deceased. His dad had remarried within a couple of years. Sally had always treated him well and had encouraged the twins to be nice to him, and they had. So, all in all, they all got along, he was grateful that he had a place to live, they were great to watch and it was a peaceful existence.

In addition, his dad had amassed a small fortune, half of which he had left to Sally, and the other half would be Jamie's on his 21st birthday.

The only concern now was whether or not to jerk off.

Pausing for a moment, Jamie listened to the sounds of the house. A quick glance at his bedside clock told him it was nearly eight a.m. It was mostly quiet, which meant that Sally was off to her exercise class—the money his dad left her meant she did not have to work.

Jamie had just graduated high school and he looked forward to a leisurely summer before starting college in the fall. The twins were both taking summer classes to get through school faster. Emma had an early class, so she was likely gone also. That left only Ella. He favored her over her sister anyway because she had slightly bigger tits; rounded, whereas Emma's were more pointed. It was a subtle difference, but he could tell. It amazed the twins that he could always tell them apart and that they could not fool him. And of course, he never revealed his secret.

Whimsically, Jamie headed stealthily down the hall to see what Ella was up to. Maybe he could get a little extra stimulation for his morning masturbation.

The door to Ella's bedroom was slightly ajar. Jamie listened for a second and could hear heaving breathing. He pushed the door open a bit further, just enough to get a wider view. She was sitting on her bed on her calves. She had a summer dress on, but the hem was around her waist and revealed that she wore no panties. He could vaguely make out the slit of her pussy. The straps of both her dress and bra were down around her biceps, her tits were mostly out of the cups of her bra and she was playing with her nipples.

Pulling her breasts completely free of her bra, Ella leaned back against a bunch of pillows propped up. She stretched her legs out and shoved one hand between them, playing with her pussy.

Grinning for no one to see because he had come at the right time, Jamie pushed his boxers down, letting them drop to the floor. He grabbed his erection and gave it a few tugs. He knew the big show was still to come, so he didn't want to stroke himself too vigorously just yet.

Ella was rubbing all over her body with her other hand, and then turned slightly onto her side and played with her ass. She then returned to her back, spread her legs and became serious with her pussy. Her other hand twisted and pulled on her nipples. She sat up slightly to completely remove her bra and gathered her dress around her waist, and then lay back down.

When she started moaning, Jamie pushed the door open a bit further.

Ella was thrusting her hips to meet the motion of her fingers on her clit. A moment later, she sat up and squirmed to the edge of the bed, allowing her feet to touch the floor. This gave her more traction to pump her hips, as well as, jam a couple of fingers into her pussy.

Jamie love the squishy sounds of her fingers fucking herself. Her moaning also became louder. He beat his cock a little harder, but still not enough to make himself come. But his stepsister was now writhing on the bed, her fingers a whir going in and out. And then she calmed down a bit; however, he couldn't tell if she had orgasmed, so he leaned in further, which caused him to step out of his boxers.

At that moment, Ella looked up and saw him standing there. "What are you doing?" she asked, although not in anger. "Get over here."

He hesitated and quickly lost his erection, but made no move. He'd never been caught and now he feared what the outcome might be. They'd always given each other space, but now he'd violated hers. If she told her mother there was no telling what would happen.

"Come on." Ella patted a place on her bed beside her. "Sit down."

Believing it safer to comply and maybe talk his way out it, as he took his first step, he was surprised that she made no attempt to cover herself up. Perhaps this wouldn't be as bad as he thought.

When he finally sat without saying anything, Ella said, "I suspected you were watching me. This is not the first time, is it?"

Jamie was too stunned to speak, both from being caught and still being able to look at her beautiful body.

"You like watching me?"

He nodded hesitantly.

"So, today's your 18th birthday. Happy birthday. I wanted to do something special for your birthday, but I couldn't think of anything. But now. Have you ever watched a girl masturbate?"

He merely shook his head, watching her toying with her nipple, but trying not to be too obvious.

"Have you ever been with a girl?"

"No, not really," Jamie responded slowly, his voice raspy due to his nervousness.

"Have you ever seen a pussy closer than from the doorway?"

"No."

"Would you like to learn more?"

With wide eyes and raised eyebrows he nodded.

Ella took his hand, move closer to him and sat on her haunches.

"What if your mom finds out?"

"Don't you worry about her," Ella assured with a snicker, thinking if he only knew about her mother and sister. "But don't say anything to her."

"I won't.

She took his palm and pressed the tips of his fingers against her pussy. "How does that feel?"

He could barely get the words out. "Feels good."

She spread his forefinger and middle finger slightly. "Rub them against my lips." She moved his hand up and down." Then she took just his forefinger. "And then rub my clit." She did it for him and it made her breathe heavier. "Now, stick your finger in there." She pumped his middle finger in her hole a couple of times until he got the hang of it. "Oh, yeah!" she moaned. "You like that?"

"Oh, yeah."

"Are you still a virgin?"

"Yeah."

"Well, one day, you'll put your dick inside of one of these."

Jamie continued to finger fuck her. He didn't want to stop. Ever. His erection had returned and it felt bigger than ever. She rocked her hips to meet his thrusts. She grabbed his arm and move it faster. He got the message and increase his tempo, amid her moaning.

"Oh, yeah," she kept repeating. Another wicked thought occurred to her and she grasped his hand, brought it to her mouth and licked just the very tip that had been in her pussy. "Mmmm." She then lifted his hand to his nose. "Smell it."

"Nice."

"You want to smell the real thing?"

"Uh-huh," Jamie agreed. This might be his one chance so he wasn't going to turn down anything she offered.

Ella laid on her back and spread her legs. Jamie rolled onto his stomach and moved his head in for a whiff. It didn't smell bad, but he wasn't sure it smelled good. However, he was closer to a real pussy than he had ever been and that part of it was fantastic. Without waiting for her approval, he raised his hand and touched it with his fingers, as she had shown him before.

"Want to lick it?" All the while, subconsciously, Ella was convincing herself that she truly was giving her stepbrother a lesson. She was exposing him to the female anatomy in a way that he needed. He was a good guy, one any girl would be lucky to have. So, when the right one came along, he would be better prepared. Of course, the other reality was she was horny and had found a new way to get off.

"Yeah." When he'd touched it with his hand and stuck a finger inside, it felt pretty much as he expected, at least from a tactile perspective. From a psychological viewpoint, it was incredible and made his head swim. However, as he stuck his tongue out and leaned his head in until he made contact, he didn't know what to expect. He'd seen guys do oral sex on girls in porn videos, and while that was exciting to watch, he had no concept of what it would actually taste like. He'd only gotten a hint from the smell. His first lick was tentative, and there was no immediate distaste. So, for his next swipe he moved the tip of his tongue around a bit. His cock pulsed and he quickly realized that it was the cerebral sense of it that got him: he was licking a real, live pussy, regardless who it belonged to.

Ella pointed to her clit. "Lick it right there." He did and she moaned loudly, loving it. "Now, while doing that, stick two fingers in my hole." When he did, she whimpered. "Yes, yes, yes, keep doing that!" She grabbed her tits and squeezed them. "You enjoying this?"

"Hell, yeah!" he exclaimed, finally with some excitement.

"Do you think this is dirty or wrong, doing it with your stepsister?"

"I guess not." But he wondered why she would ask that.

"Good. Now, curl your fingers and reach up and—" Ella helped move his hand until he hit her G-spot. "You feel that? Kinda spongy?"

Jamie nodded.

She pushed his head away. "Just your fingers. That's my G-spot. Find that on any girl and she'll love you and you'll make her come. Keep doing that. And while doing that, use your thumb on my clit." He did and all the nerves in her body tingled. She then came in a massive orgasm. He kept doing, but she had to yank his hand away because her pussy became too sensitive. It was so powerful that even with nothing touching her, she was still feeling it. When she had pushed his head away he had sat up slightly to get a better angle with his hand. Now, she could see his massive hard-on and couldn't believe how big he was. She reached for it.

Her touch caught Jamie by surprise and he scrambled to move away. No one had ever touched his penis.

"It's okay," Ella whispered to calm him. "You got to touch me; it's my turn. You'll like it. It'll feel good."

And suddenly feeling another hand wrap around his cock did feel good. It felt great!

Ella pushed him onto his back. "Wow! I had no idea you had such a big dick! It's beautiful." It pulsed involuntarily. "And it likes me holding it."

Jamie couldn't believe what he was hearing. But he liked it. He'd always admired his stepsisters, and now to have one admire him . . . it was wonderful. He thought his cock would explode when he saw Ella stick three fingers in her pussy, slosh them around, then rub her juices all over his penis and start stroking him.

"Does that feel good?"

With bulging eyes, all Jamie could do was nod. He felt pre-cum ooze out.

Noticing also and grinning, Ella stuck out her tongue and licked the clear drop off.

Jamie felt lightheaded. Watching porn and living with three gorgeous women had him constantly fantasizing. His spying had given him specific bodies to dream about. But never in his wildest imagination had he expected anything to ever really happen. He'd never even hoped it would really happen because it was just too far-fetched. Now. This was the greatest experience of his life. He would have been just as excited if it had been Emma, but he was extra thrilled that it was Ella first.

Feeling bold, as Ella continued to stroke him, he reached out and played with her pussy.

Ella giggled. "You naughty boy." But she moved her hips with his fingers. Some of this was new to her, as well. She'd been with boys, had sex, done things. But holding a cock this big—certainly she'd never fucked one this size—while he was finger-fucking her was incredible. With her other hand, she held onto his thigh to steady herself and bounced on her legs to meet his thrusts. "Oh, oh, oh. This is fantastic! I'm gonna come again. Make me come, Jamie, make me come."

RonCabo
RonCabo
2,045 Followers