Lily - Cover

Lily

Copyright© 2015 by Rich Bottom

Chapter 1

Erotica Sex Story: Chapter 1 - A big-bottomed MILF

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Heterosexual   Fiction   Anal Sex   Slow  

Rich had been crushing on Rosalyn for months, and he'd finally worked up the nerve to ask her ... if she wanted to study with him. She shrugged her shoulders and agreed to it, but she didn't seem particularly excited, so he wasn't sure if it was a turn of fortune when she offered to host their study session at her house. Rosalyn wasn't particularly catty, or mean, or cliquish, but she also wasn't as approachable as Rich would have wanted her to be. She had a "leave me alone" expression on most days, even when she was hanging out with friends, and her shredded jeans and fingerless gloves were as trademarked as they were indicative of someone rough around the edges. He was pretty sure she'd dyed her blonde hair black, but he didn't hold it against her, as he couldn't imagine her looking any other way. As he got to know her, he realized that she wasn't as violently loner as he'd first expected, but she was hardly warm. He wasn't sure if she was interested in him at all, and suspected that she wasn't, but his heart still started to race when she leaned in close to him and whispered to him as they approached her house.

"My mother's home. Just try to ignore her, or she won't leave us alone."

"Is she ... overprotective?" he said, unsure.

"No, not really. She just has a tendency to exaggerate wildly whenever I have a friend over, like it's a major event. I have to cut her down early or she'll smother us, so try to act douchey if you can."

He'd heard it, even if he didn't think she did. Friend. He felt a twang of disappointment, but he wasn't about to give up all hope.

He followed a step behind her as she approached her front door, wrangled around in the chaotic contents of her purse for her keys, and shoved one in the keyhole. She had to jiggle it a bit to get it loose, but she seemed to know the trick. She pushed the door open with her shoulder, sighing with the effort, and preemptively rolling her eyes as she called out "I'm home!"

He followed her into the front room, where she kicked off her flats, and slipped into a pair of incongruous bunny slippers, and offered him a pair of sensible toe-covering men's slippers, which he took with some suspicion.

"They were my dad's. Never threw them out, I guess."

He put them on without saying anything, and she rolled her eyes again and yelled "Ma, are you home or not?" as she stomped her way into what he assumed was the kitchen. He followed her in, and a girl with golden blonde hair down to her ... legs, was washing a dish. He tried not to let Rosalyn catch him looking at the girl's figure, which was considerably fuller than her own, if a bit on the heavy side. It slowly dawned on him that Rosalyn never mentioned having a sister.

"Rosie, you don't like it when I call back at you. You say my voice is too sugary sweet," she said, inflecting 'sweet' upwards in a sing-song manner. She turned around, spotting Rich for the first time, and he noticed that she wasn't a girl at all, but a full-grown woman. He tried to resist letting his mouth hang open when he noticed that she looked a lot like Rosalyn, but maybe ten years older, with big green eyes that she didn't have, and what he still assumed was her natural blonde hair. His eyes wandered down to her top, a modest blouse that she'd strangely taken to smuggling watermelons in. They bobbed up and down as she breathed, but it seemed more like she was trying to cover them up than show them off. He looked up to her face, suddenly aware that there were two women in the room that were probably going to be watching him for such displays of eye-wandering, but what he saw was the brightest, most innocent smile in the world, friendly and caring, trusting and hoping. He found he had to look away, ever so slightly, while smiling dorkishly, in the hopes that she wouldn't notice the utterly devastating effect her smile had on him. If she had noticed his perving out, she certainly didn't let it show. She seemed genuinely happy to see him, as if they were old friends.

"And I don't like it when you call me Rosie, either. It's Rose or Rosalyn."

The woman shook her head and laughed a small laugh. "I know, honey; I named you," she said, and Rich had to bite his lip to stop himself from boggling. It was impossible. "But everybody calls you Rose. You'll always be Rosie to me."

"Mom, can you not embarrass me in front of my friend?" she said, spitting out the "b" in "embarrass" like a curse. Rich didn't know what threw him more: that she'd called him a friend, again, or that she called her older sister "mom".

"I'm sorry ... I don't mean to. Hello, what's your name?" she said, looking back to Rich again, who averted his eyes to the floor rather than face her smile again.

He tried to bear in mind Rosalyn's advice to "act douchey," but he found he couldn't bring himself to it. Instead, he smiled goofily, endured a second of eye-contact, and said "I'm Rich," offering his hand for a handshake.

"That's good news," she said, wiping her hand with a towel and then taking his hand. He felt her hand, warm and soft, and saw her playful expression, and he almost didn't want to let go. When she got closer, he realized that she smelled of lilacs, and it was the first time he ever really noticed a woman's smell. It wasn't perfume, so it must have been either the real thing or a soap or something like it, but he didn't care. He now loved the smell of lilacs. For a fleeting moment of insanity he considered caressing her wrist with his thumb, and playing it off as a satire of an overconfident ladies man, but then he nervously laughed instead. "I'm Lily, Rosie's mom."

He withdrew his hand. "It's nice to meet you, Mrs. White."

"Call me Lily," she said, still beaming at him. She turned to Rosalyn. "You make sure he doesn't go around calling me 'your mom' now, okay?"

"Okay, mom. We're going to be studying in my room. Without mom."

"Do you guys want me to make you something?" she said, looking between the two of them, before settling on Rich. "What do you like to eat?" she said, sweetly.

He fought the urge to say what he wanted to say. "Anything's fine. You don't have to, though."

"If I don't cook anything, Rosie won't eat anything," she said, and he found himself looking at Rosalyn, who was considerably leaner than her plump mom.

"I'm fine, mom. Just leave us alone, okay?"

Lily looked hurt for a second, but then her smile, somewhat sullen, returned. "I'll try to keep busy. If you guys need anything, just ask me."

Rosalyn was about to cut back, so Rich hastily replied "thanks, Lily." Her somewhat sad stare quickly flicked to him, appreciatively. Rosalyn slinked away without another word, and Rich followed her, trying not to look back at her mother one last time.

When they'd settled into her room, which was cleaner than he expected, she dropped a math tome between them. "She's always like that."

"She seems nice," he said, trying to keep her smile out of his mind's eye.

"She is, I guess. It just hasn't been the same since my dad ... she cares too much, I think."

He didn't know what to say to that. Instead, he decided to say the first dumb thing that popped into his head, with exemplary results. "Your mom's really pretty."

Rosalyn stared daggers at him, and his mind reeled trying to think of a way to backpedal out of it, but then she just laughed. "Don't you mean 'Lily' is really pretty? You don't have to call her that if you don't want to. I wouldn't," she said, flipping through the pages of the text. "She had me pretty young. And she's always looked young. Too bad I take after my dad, huh?"

Rich nodded politely. If her dad had any influence on her appearance, it was her eyes, and that was it. But he wasn't about to refute her.

"I used to have blonde hair, like her. Last year, even. I was a cheerleader, if you can believe it." He couldn't. "Sort of ... reinvented myself. And I think she wants me to go back," she stopped flipping pages, and looked up at him. "Do you think I should change back?"

He knew this was his chance. He knew there was a suave answer to her question, that would show that he really understood her. But he didn't. And he realized that, suddenly, just in time to give the honest, horribly moment-shattering answer, "I don't know."

She looked like she was about to cry. "I ... I'm sorry. I really shouldn't have dumped this on you. You just wanted to study and now I've got you caught up in my confused bullshit."

He wanted to console her, but he wasn't sure if she wanted to be touched. "It's okay. You're really not that bad."

She wiped her eyes. "Thanks. I feel kinda dumb now. I'm freaking out about nothing. Could we ... take a rain check on this?"

Rich nodded rapidly. "Sure. Uh, when do you want to try again?"

"Tomorrow. Uhm, I'm meeting up with my band after school, but you can come chill here until I get back; I know you live a ways off. 'Lily' will let you in," she said, tongue in cheek.

He stood, and she led him to the front door. He looked around for Lily, but he didn't see her. He went home, fell to sleep, and thought, upon arrival at school the following day, that he'd never woken up.

Rosalyn wasn't exactly dressed like the student council president, but she wasn't in her usual punkish attire, either. He didn't really cross paths with her much throughout the day, but from a distance he spotted her, wearing a halter top and a skirt, and most shockingly, her hair was bleach blonde. She looked like a completely different person, and his heart beat twice in one when he realized who she looked like.

She reaffirmed their engagement as class ended, climbing into a beat-up minivan that was undoubtedly her bassist's parent's car, and he made his way to her house on his own memory, alone. He had complimented her hair, and she had, smiling, thanked him, and he felt pretty good about that, but there was an extra bounce in his step all the way to her front porch, at which point he became suddenly timid. He rang the bell, and tried to find a good place for his hands, only to discover that at moment's such as the one he was in, there are no good places to put your hands. He settled for his thumbs in his pockets, his shoulders shrugged, his back straight.

She opened the door and he could smell her immediately. She was sweating lightly, and he could smell that too, but the scent of lilacs was the same as the day before, and just as sweet. She was wearing a running shirt and possibly the most powerful sports bra known to man, he assumed, while keeping his gaze at eye level. Sweat pants and running shoes confirmed his theory, even before she said anything.

"Hi, Rich! Sorry if I'm a little exhausted; I just got back from a run. Come in!"

He stammered out a "Hi, Mrs. White" only to be corrected to "Lily" again, which he then followed with "Hi ... Lily." He followed her inside, letting his gaze droop well below eye level, only to have it snap back up when she turned to him over her shoulder.

"I must look terrible. I just got in when you rang the bell. Do I smell?"

'Like sweet flowers' would have been his response if she were fifteen years younger, but instead he just said "I don't mind."

"That's kind of you. To tell the truth, I'm sort of embarrassed to let anybody see me run. I stick to the old train tracks so nobody spots me. Guess I don't have to tell you now that you've seen the new Rosie, or the old Rosie, I guess, that I used to look just like her," she said, taking a seat on the sofa in the living room, gesturing for him to sit down opposite her.

"You still do," came his response, automatically, and he was horrified to hear his voice was less casual flattery and more emphatic declaration.

"Thank you! That's so sweet. But we both know that any mirror that made us look the same would be in a funhouse. I've gotten a little fat ... you can be honest."

"You look good," he found himself saying, again a little too strongly.

"And you've earned yourself some free tips," she said grinning like a cat.

"Tips?"

"For wooing my baby. You're interested in her, right?" she said, twirling her hair in her finger, watching him for his reaction.

"Um ... I mean, I was, but..."

"Don't give up!" she said, suddenly getting to her feet. He watched her breasts take the long way up, and then bounce in place. She sounded a little full of energy, and a little desperate. "I know she can be a little cold, but she's a really nice girl."

"I think ... I think she just wanted a friend. To talk to. I'm okay with that..."

"Are you?" said Lily, smiling at him in admiration, melting his resistance. "You really are a gentle boy. But she hasn't told you no yet, right?"

"Well, no, but..."

"When a girl doesn't know if she's in love, you've got to let her know how you feel! And with me on your side, you can't lose," she said, full of youthful energy, offering her hand to him. "Deal?"

Without thinking, he took her hand, and said "deal," shaking his head and laughing at her good-natured spirit.

She walked over to the pantry and took out a towel. "Alright. She won't be home for at least another few hours if she's practicing. I'm gonna take a quick shower, and then we can put our heads together."

At the mention of Lily showering, Rich suddenly wanted very much so to put something of theirs together, but it wasn't their heads. He watched her walking towards the bathroom, and knowing that no one would see him staring, he stared. Her running shirt had a racerback, and he watched her neck and her shoulders with some fascination. If Rosalyn would look like her some day, maybe he really shouldn't give up, he thought.

She disappeared into the bathroom and he heard her turn on the shower. She emerged a second later, and he felt stupid when he realized that he had been hoping that she'd already taken her shirt off when she did.

"We could roleplay," she said, eyes bright.

"What?" he said in a scared monotone, as a very different kind of roleplay came to mind.

"I could pretend to be Rosie, and you pretend I'm Rosie, and maybe you'll be able to work up your courage that way."

"Oh. Uh ... okay, I could do that."

"Sorry to jump out at you like that. It's just Rosie hand-washed some of her old clothes, and I just saw them in there with all her old jewelry she stopped wearing. I forgot I didn't have any clothes in there, so I'm just going to run and grab some," she said, and went to go towards her room.

"Wait," said Rich, his mouth ahead of his mind, "why don't you wear her stuff?"

"Why would I ... oh. Oh! Hey, that's a good idea," she said, and he tried not to chuckle at just how blonde she appeared when she said it like that. "But ... there's a problem."

"What?"

She pointed to her hip, and he jumped at the invitation to look. "It'll never fit me."

"You think so?" he said, diplomatically, and he couldn't help but smirk when she blushed at him. Then, in a moment of either evil genius or pure dumb luck, he said, "I mean, Mrs. White, we don't have to do this if you don't..."

"What was that?" she said raising an eyebrow.

"I said you don't have to..."

"Lily," she said, walking over to him.

"Lily," he replied, dutifully.

"Say, 'Let's do this, Lily!'"

Images burned in his retina as he watched her smiling eyes and she watched him. "Uh ... let's do this, Lily."

"I'll make them fit," she said, disappearing into the bathroom, closing the door behind her. He could see the steam of the shower starting to seep out at the top of the door frame. In spite of himself, he waited a few seconds, and then he slowly approached the bathroom door. It was opposite Rosalyn's room, and so he readied the excuse that he was just looking inside her room; a lesser sin that he could readily confess to.

He listened at the door. He heard Lily's clothes hit the floor, and then her soft footfalls on the tile, and he knew that her body was bared. He heard the water stop hitting the ground for a moment, and knew she had stepped into the shower. He heard the splashes as water accumulated on her and fell, and he heard her pick up a bottle of what he assumed was lilac-scented soap or shampoo.

He saw in his mind how her hands caressed her own body, her neck, her breasts, and even ... he was woken from his trance by the sound of her humming, and he could hear that her voice was lower than she let on, a womanly tone with softness and honey to spare. She sang a song filled with a bygone happiness, and more than a little sultriness, and he started to seriously wonder what Mrs. White's bed slept like. Lilac, or lust?

His schoolboy fantasies came to an end with the shrill noise of a shower being turned off. He heard her step out of the shower, and took a few safe steps away from the bathroom door, for plausible deniability. He heard her say "oh, these are cute!" and heard jingling, and he heard fabric being unfolded, but then he heard her mutter "oh no."

Silence followed. Maybe after half a minute of her speaking under her breath, trying to puzzle something out, the door opened slightly, though Lily didn't emerge.

"Rich?" she called out, trepidation in her voice.

"Yeah? Lily?" he called back, from an even further distance than he'd been waiting.

"Um, so ... I was right ... it doesn't fit..."

"It's okay. What's the problem?"

"Well, there's two," she said, nervously chuckling, "I threw my clothes down the laundry chute, and the basement is locked. I'd have to look for where Rosie left the key."

"Is it really that bad?" he said, curious.

"Not ... that I can see ... but there's the other problem. There's no underwear in here."

The situation was quickly becoming too much for Rich to bear. "Do you ... need underwear?"

"In general or right now?" came the jovial, if anxious reply.

"Right now."

"Well," she said, and then took a deep breath, "this skirt doesn't ... cover as much as it does on Rosie. Which isn't much either. So, can you ... please do me a big favor?"

Rich nodded, even though she couldn't see him. "Sure. What do you need?"

She hesitated. "My room is the one on the right. The bottom drawer of the left cabinet."

He swallowed. He'd never been in a situation that demanded swallowing for before, but this one did. She closed the door sheepishly as he passed it, made a right, and entered into her bedchamber, as he came to imagine it. It was dark, but he didn't want to turn on the light and see a place he really wasn't supposed to be, so instead he scouted for the cabinets, found the one on the left, and opened the bottom drawer. He sort of knew what to expect, but the sight was still a lot to take in. You couldn't say Lily was an ostentatious woman: most of her underwear was plain and white, a simple cut, some with lace and some with words. All of them were large or even extra large, which didn't surprise him, but the actual size of them did. Without thinking, because he was beyond thinking at that point, he spotted something purple and picked it up to investigate it, only to realize what he was holding and nearly drop it. To his relief, it looked as if it had never been used, but he carefully placed it back where it was regardless, picked up a clean white pair of panties, closed the drawer, and evacuated the room with haste.

Without a word, Lily stretched out her hand from behind the door. He handed her the underwear, and she took it back into the bathroom with her. A few seconds later, she emerged, and Rich would never forget what he saw.

Her hair was wet, and her handkerchief was tied up in it, but she let it flow relatively free, all the way to her backside. She was right about the skirt, as even from the front Rich could see that anyone behind her wouldn't have to so much as crouch to get a clear view of her underwear, and if she hadn't been wearing any, her nudity. The "cute" jewelry she'd found she probably wasn't aware of the connotations of, as they were large, gold hoop earrings that Rich couldn't even see her daughter wearing with a straight face. Her appeals to modest notwithstanding, Lily clearly didn't pay much mind to her breasts, as the belly shirt that would have been tight on her daughter's modest bust didn't at all reach her belly, and in fact barely covered her breast, the underside of which was similarly visible to anyone capable of bending at the knees. Moreover, though she'd asked for underwear, she either hadn't thought to include or was too embarrassed to ask for a bra, as the proverbial cherry on the cake was that Lily's nipples were clearly outlined in the fabric. She looked at him with a certain pride that she managed to fit into all of it, though her blush was a little redder now than it had been before, and she held her hands in front of her timidly, afraid that any movement endangered her purity. While she may have had little insight into how large her breasts truly were, she knew enough that if she lifted her arms above her head, she was going to fall out of her shirt. Rich wondered if he asked her to get something on a high shelf ... no, that would be wrong.

"Hey Rich, you ready to study?"

She imitated Rosalyn's voice, which had the exaggerated inflections of a teenager, and Rich suppressed a snicker. She was already getting into character, in spite of the dangers of her chosen wardrobe.

"Of course. Been waiting for you for a long time now. Your room again?"

"Yeah. This way we don't have to deal with my mom" she said, rolling her eyes hyperbolically, and Rich laughed out loud, a genuine laugh that surprised even him. Lily smiled back, and the tension about her appearance dissolved.

"You wanted to study math, right?"

"I suck at math. My dad used to help me with it, but..." she trailed off. He couldn't tell if Lily was really good at acting, or if she'd suddenly forgot she was.

"I could help you with it. In fact, I want to help you with it," he said, and Lily sat down on the floor, where the math text from the previous day still conveniently lay.

"Oh yeah? And why's that?"

He sat down next to her. "Because ... because I..." Lily's big green eyes were looking at him. He couldn't say it.

"Relax," she said, nudging him, "it's just me. Go on."

"Because I care about you," he said, and strangely felt tears coming to his eyes.

"You care about me?" she said, feigning surprise rather well.

He took her hands in his. "You ... you always seem like you've got a little sadness, and you don't have anyone to help you with it. You're so bright and cheerful otherwise, that I just want to make you happy."

"That's..." Lily said, and felt tears in her eyes, too. She leaned her face close to his.

"Uh..." he said, not sure what to do.

"You can't panic if she goes in for a kiss. Just relax and do what feels right, okay?"

"Okay," he said, willing every fiber of his being not do what felt right.

She leaned back. "Let's try again. Um ... so, are you saying ... you have feelings for me?"

"So many feelings," he said, smiling, and she grinned nervously back. She hadn't expected a somewhat smooth answer.

To catch him off guard, she leaned in close again, and said in a full, sultry voice, "really?"

In riposte, he took her hand in his, and put his hand on her neck, caressing her face. "Really."

To diffuse the situation, she said, "Rich, don't you think we're going too fast? I mean, I don't know what I should do ... I'm conflicted," she said, and then in her own voice, she whispered conspiratorially, "now you'd have to reassure her," her face still close to his, and he nodded.

"I know what I want," he said, his thumb touching her lip, and then he brushes the hair from her eyes.

"You do?" she said, looking down at his lips, and then up into his eyes.

He nodded again. "You, Lily."

She smiled, prettily. "Good," she said, approving, watching his finger trace along her cheek, "but you mean Rosalyn."

"No, I don't," he said, leaning in closer. Lily hesitated to pull away, and was a second too late: their lips touched, briefly, and she slowed her retreat, and he followed, and drew her face to his as he kissed her lips again, longer now, with even less of a pretense.

"Roleplay" she managed to stammer in between kisses, but even as she leaned back, she returned his kisses, her body shaking, her breath quick, so that it was less of a rescinding gesture and more of an invitation. He was inexperienced, and he knew it, but he pressed the attack, watching as the grown woman beneath him, with him, embracing him and staring lovingly at him became as full of anticipation, wonder, dread and lust as any young girl with a new love, and he knew then that she was just as vulnerable as he was, just as forbidden, and yet free. He smelled the lilacs from her shower as he followed her to the floor, kissing at her neck, then, as she prepared her quivering heart and her aching loins for something she had long denied either. Her legs curled around him and he noted that they were stronger than he expected, likely due to her efforts in running, but he knew that she didn't mean to trap him, only to reassure him that he was welcome in her arms and that she hoped that she was welcome in his. Their clothes were still confining them but they both knew that it was all in due time, as they explored each other's bodies as they were. She took his finger into her mouth, he gently teased her nipple through her shirt, not wanting to hurt her but wanting very much so to please her. She rubbed her hands over his body, and guided his hands over hers. They started to exchange words, then far past the point of deniability, and she asked him in simple terms if he liked her body. He answered with action, barely able to control himself as he ran his hands down her form, her breasts, her waist, and though he hesitated, she helped his hands under her, to her soft cheeks.

Having given her body to him, she reached down his front, and between them places a hand on the hard outline that's pressed against her leg. For a moment, Rich lost his confidence.

"Uh ... sorry..." he said, but when he looked at her face, that same smile she wore when he first saw her looked back at him. Without being told to, he adjusted himself so that his prominent manhood rested just under her skirt, and then pressed his body against hers. No longer in the realm of adolescent play, they entered the realm of the adult, and she felt the weight of his sex on hers, and he felt her heat, her moisture, and began to smell the scent of a woman beyond lilacs. She wanted to watch as he went wild with lust, but she was in little position to judge, as the feeling of his hard cock with just a thin, meaningless membrane of fabric between it and where it belonged, had made her realize firsthand what years of neglect will do to a woman, and she grew ever more acutely aware that if he did not find his courage or let his passions overtake him soon, she would climb on top of him, and use her leg muscles to get what she needed.

She didn't have to wait long, however, as suddenly she found herself on her belly, her soon-to-be-lover pressed against her back, biting at her neck, feeling her up and down, waist and hips and ass and back. She'd never done anything on the floor before, but she knew that she was about to. She thought for a moment about being mounted from behind like an animal and then it was the only thing she could think about. Rich, meanwhile, had satiated his tactile curiosities, and in almost retrograde motion was taking in the visual. He knew better than to concern himself with Lily's ass, and instead lifted her too-short skirt, and sees in full view what before he had only thought to glimpse, her underwear so soaked through that it was essentially invisible. She felt his stare and reveled in it, even though she was still somewhat embarrassed about being viewed from behind. Jolts of sensation made her claw at the floor when first his breath touched her, and then a finger prodded through the fabric, and then, without warning, he pressed his nearly-freed erection directly against her, and though he was off the mark, he pressed instead directly against her clitoris, and her moans were evidence that he had done something right. She held back, as she knew that she did on occasion ejaculate, and that was not something she wanted to explain to a curious virgin while he massaged her pearl with the head of his cock. Despite holding back, she felt something wave over her, too small to be an orgasm but large enough that her body remembered what an orgasm felt like and then, more than ever, wanted Rich inside of her.

"I'm ready," she said, her sweet voice now teeming with deep undertones, as she brought herself up onto her knees. She waggled her hips and looked back at him, and nearly squealed with glee as he moved her panties aside, exposing her to the open air. She dropped her head and steeled herself, and he fumbled to free himself from his own underwear, when she spotted it on the floor: her daughter's math textbook.

"We can't do it in my daughter's bedroom!" she said, suddenly, and before she could even begin to voice her suggestions, a man's voice said "in the bathroom, then," with a commanding authority he drew from somewhere unseen.

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