Worcester, MA, 1996
Richard Raintree, age eighteen and born Richard Marsden, peeked around the door jam into the bedroom of his eighteen year old sister, Renee. She was his stepsister really, the family now made up of his Mom, and her Dad, both on their second marriages. It was the only way really, they could look nothing like each other, and yet be born only a few days apart, Renee three days older than Richard.
Renee's mother was killed in an automobile accident when she was four, and Richard's father had had left the marriage before Richard was born. Ellen Marsden had refused to give him his father's name and kept her own for Richard. It was a tough time for all four of them, until the day Ellen and Ronald met.
When Ritchard's mother married Ronald Raintree, she'd decided her dream for a caring and honorable husband had come true and assumed her husband's name for both her and her son. Ritchie, the household name for the "cute little guy," Ronald and daughter Renee welcomed into their lives, was loved and nurtured on the surface like any other son. It was Ritchie who assumed something was amiss. He couldn't put his finger on it, but he noticed his big "sister" and he had somewhat of a different relationship than similar pairs at school. Most of course had siblings, but few if any shared his and Renee's closeness in age. And most it seemed, we're more at each other's throats than quiet and friendly toward each other.
Renee was a kind of big sister at times, having matured like most girls at a faster rate than their male counterparts, and a bit of a surrogate parent when parents left them alone. She was too much more mature to become a "buddy", and yet too young to be respected by her stepbrother like an adult. He felt she was too into other boys and grown up things to take her into his confidence. In earlier years she had even babysat and looked after him as if he were the neighbor's kid, not her brother.
While he was for many years too young to understand that the added convenience of a built in baby sitter enabled both Ellen and Ronald to more actively pursue their careers, leaving them out of the home during most business hours and on many occasions of after hours business entertainment.
Not surprisingly, it was from this environment, not forced but certainly encouraged, that his early independence grew as well. His intelligence had already begun to set him apart from others at school, for he seemed to be doing everything a year or two ahead of the class. And now he wondered, in their senior year, if he was doing this ahead of his friends at school too. Surely they must spy on each other like he was, watching his unsuspecting sister in her room.
Richard might have been immature in the social aspects of life compared to his stepsister, but he was way ahead of the masses when it came to the application of his intelligence. He had his room, and his share of the basement where he maintained his "shop." He had his interests, and they carried him well beyond the usual experimentation of most kids his age. Already he was playing with robotics and electronics in ways most college students in their fourth year of engineering would find both fascinating and beyond their understanding. For Richard was a genius.
And yet, as he peered through the door to Renee's room, and watched her reflection in the mirror over her dresser, he realized he was also a voyeur on life, a tag-along, or an outsider with no real roots, and no respected goals. He was simply there to watch, an observer of all, and partner to none. He felt a stirring between his legs, the same thing he felt at night when he was alone in his room.
Renee felt suddenly alone. Not only had her "date" for tonight called to cancel, some lie about an obligation at home, but her girl friend had suddenly gotten an offer and was now the one giggling and preparing to go out on this Friday night. She wondered only for a second if the two incidents were related, but wrote the idea off. No one had that kind of balls.
She examined herself in the mirror as she stripped down to her bra and panties, tossing her blouse and skirt on the bed to save them for another occasion. For the life of her, she could not figure out why she had trouble keeping boys. She was "stacked," as many guys had told her on their first date. She was quite pretty, as her Father had told her all her life. And she was smart, a trait both she and her brother shared, though only he had pursued.
Her breast size was a healthy 36D, though she was prouder of that earlier than of late. It didn't seem to help, despite what the boys said and tried to do, and the two hefty melons were often in the way. When she ran to keep her lovely figure, she had to wear the heaviest of sports bras. When she purchased lingerie, she had to frequent only stores with her particular size and required strength. Every time she leaned over a counter to talk to someone, she lost their eye contact as their eyes flew down her cleavage. The damn things were just a nuisance, except of course when they were handled correctly.
Renee brought her hands up under them now, and supported them, relieving the weight from the thin shoulder straps. The relief on her shoulders felt good, and the gentle touch of her hands on her breasts felt warm and pleasurable. She slipped her middle finger in front of and up each breast to touch her nipples through the fabric of the bra. Her eyes rolled back and she sighed deeply with her touch, her nipples comfortably hardening and the sensation shooting down to her loins. If she had a choice, she decided once again, she would keep the troublesome appendages for their sensuality value, for she loved to play with her tits.
Ritchie smiled as his big sister played with herself. He'd always looked at her as his "big" sister, for she was the one with the common sense, the adult behavior, and the ear of their parents. All through their youth, from age six when they'd been joined to the same family, she had been the one in charge, the one with the mission, the one who lead. Ritchie never contested her command either, happy to have the latitude to do almost what he wanted when their parents weren't around.
He watched her looking in the mirror, so interested in her own image that she completely ignored his own sliver of refection. She was standing only three feet from him, standing directly in front of her floor length mirror. The angles made it easy for him to see her. At the edge of the mirror, he could also see the crack in the doorway he was looking through. This obviously meant that if she wanted to, she could see him as well. He felt that familiar stirring in his pajama bottoms and his toes curled as he watched. She was a magnificent vision. Once she stepped aside, right in front of his view, her big ass cheeks bulging out against her panties, and her hair flowing down her back.
Ritchie reached down and cupped his crotch in his hand and began rubbing it up and down. The last time he'd done this, a few nights before, he'd also had visions of his sister in his mind, visions of lustful things that she was doing to herself, but also visions of even better things he would arrange for her.
As he rubbed himself again, he watched his sister slip a hand down her panties and perform a similar rubbing on herself. The two of them stood like that, massaging their loins for several minutes, until Ritchie heard his parents arriving home.
He cursed under his breath at the interruption, a noise he suddenly realized his sister must have heard. Not quite sure, he thought he saw her look directly at his reflection as he pulled his hand free and ran back to his room.
Renee turned her smile back to her mirror when she heard the door slam across the hall. She'd seen him at her own door just at she'd heard her parents announce they were home. Her "little" brother had been peeping again, maybe even fondling himself as she was disrobing and admiring her form. The thought aroused her, prompted her to let her hands fall down between her legs and draw themselves slowly up the insides of her thighs and pause on the mound of her dampening panties.
"Renee? I thought you were going out tonight" Ellen Marsden Raintree said casually as she entered her daughter's open door.
Ellen had withdrawn her hands and resumed changing to more casual clothes. As her mother entered, she picked up the jeans and slipped them on, before adding her favorite soft sweatshirt, the neck seam deliberately torn out of it. "So did I Mom," She said with a touch of sadness, "Guess a second date with anyone is just not in the cards."
Her mother felt sorry for her. She knew what dating was all about. She knew how hard it was to find a decent guy. Since she too had a large pair of breasts, she also knew how absolutely frustrating it could be to have so many men try to possess her, and yet so few if any come back. The wrong boys as well as prospective mates would all congregate around the aura of her long hair and large breasts, and it would be up to Renee alone to somehow learn how to tell them apart and keep the right ones. "Oh, poor baby. I'm so sorry. I know you were looking forward to this too." She put an arm over her stepdaughter's shoulder.
Ritchie got into bed and continued to rub his groin. He lay like that for some time, enjoying the soothing sensations on his shaft, and dreaming of his forbidden lust. The vision of his sister in her bra and panties, her hands feeling herself up, was too hot to put down. He reached inside his pajamas, under the cover of the sheet and blanket on his bed, and began to pump his meat. He was about to feel that strange but wonderful feeling of ultimate satisfaction again, when a soft voice suddenly said, "Miss me?"
The boy's eyes went wide and bulged up at the ceiling. That could only be the voice of his sister, and she HAD to be in his room! Freezing everything else, he looked at the door and saw Renee standing there in her sweatshirt and jeans, leaning against the jam. She smiled at him.
Ritchie was too stunned to say much. He tried with, "What… Uh… How…?"
Renee laughed and said, "Yes to all." She laughed now, and stepped into the room, closing the door behind her. When she sat on the edge of Ritchie's bed, he let go of his manhood and moved away under the covers as if she had the plague.
"Ohhhh," She purred, "I'm not gonna hurt you, or tell anyone. Don't worry. I'm your big sister, remember?" She looked around the room as if to give the "kid" in her stepbrother some time to collect himself. As she looked around, she saw a lot of the things one might expect to see in a boy's room, models, trains, and the like, but she also saw things that didn't make any sense to her at all. Little arms were reaching up from stands that seemed to have no purpose. A lifelike human eye in an egg-like container follower her movement as she leaned first to one side and then to the other. It was eerie and she looked away, back at her brother.
She placed a hand on the blanket, right where she thought the little pecker of her little stepbrother would be. She landed it exactly and felt the hardened shaft of it, much larger than she had anticipated, maybe six or seven inches long, and blushed. Looking him directly in the eyes, she asked, "Do you know what masturbation is, Ritchie?"
He was frozen in place, loving her touch, but afraid as hell of telling her that. "Duh, I think so." He'd never been able to lie to her, or anyone for that matter, but a little sarcasm helped him add some expression. He always seemed to know when someone was lying to him however, and it made him feel dirty for them. He was not able to live with the thought of that dirt on himself. He'd seen how his mother dealt with it and perhaps that is where the skill came from.
She curled her fingers to clutch the blanket and sheet around his prick, "It's when you do something like this." She pumped his cock a few times, "To yourself." She pumped a few more times and saw him shake with an orgasm. At first she didn't know what to say. She hadn't intended to really masturbate her little brother! She was just teasing him, while helping out in the education department a bit. Pulling her hand away, she quickly said, "I'm… I'm sorry Ritchie." She waited for his reaction before saying anything else.
Ritchie gathered his thoughts. Though he was quite surprised, and just a bit embarrassed at yet another spurt of jiz from his pecker, he didn't want to embarrass his big stepsister and discourage her from ever coming back. Quickly he rushed to say, "It's ok, Renee. It didn't hurt. Really! I, uh, liked it." His sheepish look consoled her.
"Oh, well, good." She hesitated, then relaxed slightly and added, "I am glad you don't mind. You don't, do you?" Renee looked at him, and then noticed the stain coming through the bed clothes. "Well, anyway, that's masturbation. But something tells me you already knew that, no?" She let the question sink in while she looked again at the stain. "You say my doing that, uh, didn't bother you?"
He managed a smile and muttered, "Yes. I mean, no. I mean, I liked you doing it, Renee." He waited an awkward moment, then plunged further with, "I did see you playing with your, uh, things too, and then shoving a hand in your, uh, underwear." He nodded alternately at her breasts and crotch.
She almost laughed at his innocence and said, "My tits, Ritchie. These are my tits." She held them up with her hands for him, bulging her sweatshirt in the process. "And this, down here, is my pussy. We're different sweetheart, but we probably get the same feelings." She though for a minute and said, "Daddy hasn't talked to you about any of this yet, has he?"
The boy in him felt better now that they were involved in a real conversation. "No, was he supposed to?"
She laughed again and said, "Yes! It's his duty! But knowing him, he won't. Poor Ritchie."
"Awwwe, that's not fair," He was mockingly upset at being deprived by his stepfather.
She put a hand on his arm and said, "Tell you what. I'll tell you all about it," She looked around his room again, "And you can build meeee…, one of your robots! Something so I don't have to put up with all the shit I get from men!" She was kidding of course, but thought the idea was a good one, all the same.
Ritchie truly thought on the proposal. How was he going to build a man? There was no way! Unless…
She looked at him and recognized his deep thought mode instantly. "Hey! I'm kidding! I'll teach you about the bird's and the bee's, but I was kidding about the robot. Wow! Are you really thinking about that?" She was second guessing herself due to the variety and sophistication of creations in his room. She always had to remember her little brother's penchant for facts and openness.
"Oh," He simply said, wondering what that meant to his part of the bargain. He decided to try to help anyway, "So, what would you want this robot man to do, Renee?"
She looked back at him and laughed, but then looked back again with a more serious expression. Her brother was simply sitting there with a serious expression. "Are you kidding? You could…"
He interrupted her again and repeated, "What would you want this robot to do for you?"
She decided to play along, but kept her answers serious, just in case. "Well… wait." She got up from the bed and disappeared out the door in a rush. Ritchie took the time to lift the covers and look at what kind of mess he'd made. He was totally wet. He quickly grabbed a couple tissues from the box on his night table and began to clean himself up. He was working feverishily, his head poking under the covers when he heard, "What's the matter?"
His sister was chuckling, and holding a red, clear plastic "thing" in her hand. When he said nothing, she boldly lifted the covers, and saw his cum stained pajamas. She chuckled again and said, "It's nothing to worry about little brother." After a moment's hesitation, she looked again at the pajamas, and reached her hand down to his waist band. Before lifting it, she looked at her brother and asked, "Ok?"
He didn't know what to say. This was all so new to him, and yet not unlike a lot of his most private fantasies. He said, "Sure."
Renee hadn't seen her little brother's dick in a number of years. A lot had taken place since then! He was growing into a real man, not exceptionally huge, but not small either, and still hard! She resisted the temptation to touch him further, dropping his drawers and the covers. "You are fine, Ritchie. Just wash it off. In the future, you might do that near the toilet, or have a tissue handy." She sighed and looked away to relieve herself of the warmth growing between her thighs.
Ritchie sighed too, relieved he needn't be embarrased. His attention went back to the "thing" his sister was holding, his curiosity running wild. He reached out for it, then waited while he looked at his sister for an "Ok." When she nodded and held the dildo up for him, he took it in his hand.
Quickly, he sat up in bed, switched the dong from one hand to the other, looked the device up and down and longitudinally, and squeezed softly and then pinched it hard.
Renee was tickled to see him flinch slightly when he pinched it, empathizing automatically with the poor thing. What impressed her though, was his detailed observations and subsequent descriptions. He was rambling off a list of ingredients that he thought were used to make the stiff gelled instrument and suddenly got out of bed and walked to his dresser. Pulling out a large figurine, something like a Batman, he walked back to the bed and handed the toy to his sister.
She looked at it, felt it and twisted the arms and legs and then bunched it up in her fist and noticed it somewhat retained the shape she gave it. She looked at her brother and said, "So?"
He looked at her as if she must be kidding and said, "Same stuff."
Renee was still confused. The figurine twisted and held different shapes. Her dildo never changed. "How can it be the same stuff?" She asked.
"I have wire in mine. That's the only difference. Oh, and yours has clear plastic, while mine has coloring." He held up the dildo, looked at it some more, and said, "This is pretty simple Sis, kind of like just making an arm?" He looked at his sister to find out what was so special about this toy that looked like his prick. "You want to build a whole man out of this?"
Renee didn't know whether to laugh, or pick her brother's brain. His sincerity and apparent expert observations, led her to lean toward the latter. "No, silly. Actually, this is about the only good part a man has!" She couldn't help but laugh.
Her brother looked at her, then down at his lap, and back at the device. There was a blank look on his face when he looked again at his sister.
She decided to confide in him, having gone this far. "This is a dildo, Ritchie. Does it look familiar?" She held it in front of his face.
He looked at the device again and said calmly, "Yes. It's a… well… what did you call it?"
She was getting just a bit frustrated, but continued. "A dildo!" She looked around to see that the door was secure. Otherwise, her prudish stepfather would be in there in a heartbeat. "Yes, it's modeled after a man's… dick."
Ritchie was both amazed at the intimacy of their conversation, but also being able to tie the word he'd heard bantered about by the guys at school with its true meaning, to his sister's voice. He looked up at his her and asked, "Ok, but what do you do with it? I thought only guys had these things."
She wanted to scream and laugh at the same time. "That's the whole problem! Women want 'em, and men have 'em!" She lowered her voice again. "Men and women, Ritchie, don't just make babies by sticking these things into here," She pointed to her own lap. She wondered if he could really be this naïve. "They also do this for fun, for uh, enjoyment, kind of like what you did watching me, but even better."