Lily Aldridge, MILF Gone Naughty

Disclaimer: All the character are 18 years old. All events, characterizations depicted are completely fictitious.

Prologue:

A sliver of sunlight made its way through the closed curtains and fell on the master bed which was a tangle of disheveled white sheets and naked bodies. There were three people lying on the bed, as naked as the day they were born. The was Lily Aldridge, the world famous Victoria's Secret Angel. She gently lifted her head. Her brunette hair a tangled mess, but still looked incredibly sexy. She rubbed her eyes, as the sunlight shone on her sun-kissed bronzed body, bouncing off her small boobs. She looked around to the two bodies around her, and smiled to herself: last night had been fun. She couldn't remember the last time she had that much fun. It was certainly before she had kids, and before she was married. She got up, and walked to the window, her ass swaying with each step. She opened the curtains to let the light in, and the bodies on the bed were bathed in golden light. The window faced the ocean. She stretched her arms, her naked body slowly coming to life. She turned around to see the two naked 18-year-old boys also starting to stir. They saw her standing in front of the window, her incredible naked body framed against the ocean view, and their young cocks started to fill with blood. The blond boy, Jason, smiled and Lily smiled back, already thinking about what she was gonna do to that cock of his. The other boy, Ramon, long and dark-haired, got up, his glorious erection pointing straight at her. As her thoughts were flooded by scenes from last night, she smiled to herself, the fun isn't over.

Chapter 1

Lily was fucking tired. She was tired of being the perfect wife, the perfect mom. She was tired of taking care of everything in her life, taking care of her body, trying to be sexy for her husband, nurturing for her kids. It seemed she didn't have any time to think, or rest, or just fucking be. She sipped on her martini, as strobe lights danced around the club.

She had joined her model friends for a "MILF's night out" (Candice's words). It was her, Candice, Alessandra, Behati and Lais. They had noticed that Lily was worn out these past few weeks and taken her out to dancing. Lily tried to fend them off at first because she didn't want to make the effort of getting all sexy, but then she thought about how she hadn't done that in a while. And she thought, fuck it, I'm gonna have some fun tonight. She didn't put a limit on fun. She was willing to go bad.

The club was Ale's choice. It was famous for a young clientele. Average age could not have been more than 22, and it was also rumored that the bouncers were very lax. And it looked. They were surrounded by what looked like college freshmen. Ale always liked hanging out in places like this. Even now, as Lily sat in the VIP section sipping on her drink, with Behati and Lais flanking her, Ale was on the dance floor, sandwiched between two boys who couldn't have been more than nineteen. The boy behind Ale was grinding his crotch in her ass, and she was loving it. The Brazilian MILF was wearing a very low cut dress that ended way above her knees. The boy facing her was way too close but Ale didn't seem to mind at all. It seemed she had forgotten all about her fiancee. Lily smirked thinking how much fun Ale was having and got up. She was going to get some cock tonight.

"Where are you going, babe?" Behati said, swaying to the music, her eyes glued to a group of boys in leather pants. Behati loved some man ass.

"To the bar, getting another one of these," Lily said, pointing to her empty glass.

"Baby, you are in VIP. The drinks will come to you. Just wave."

"It's okay. I wanted to stretch my legs."

With that, Lily walked towards the bar. She was wearing a black miniskirt and a padded bra, that made her tits seem bigger than they really were. The skirt was really tight fitting and showed off her glorious ass. After two kids, she had to work hard to maintain that ass, and worked had she did. She spent a lot of time in gym to get this body and she was gonna show it. She was also secretly hoping some of the boys would notice her ass and come talk to her. She was dying to be flirted with, and if the right one came up, much more than just flirting.

She reached the bar, but before she could order, the bartender presented her with a drink.

"This is from that gentleman over there," he said pointing to a man in a navy blue shirt at the other end of the bar.

Lily looked at him and flashed her million-dollar-smile. The man was good-looking but not her type. He had a day old scrub, and his hair didn't look washed. Make an effort if you wanna fuck some prime pussy, she thought. The other two guys who hit on her were also no-go. She was starting to get frustrated (and more horny). She looked at the dance floor. The girls were wearing next to nothing, twerking, swaying their hips. The boys were equally in the mood, enjoying the loosened inhibitions of sexy girls. Lily noticed the guys were much hotter than when she was younger. It seemed guys took much better care of themselves these days. Her eyes drifted to Ale, who was making out with one of the guys she was dancing with. His right hand was squeezing her tit, and she made no effort to shoo it away. The other guy was kissing her neck lightly. Lily was sure Ale would fuck one of these boys, or both. Lily wanted a fuck-toy of her own.

Just as she was thinking that, she saw two boys walking towards her. They looked not a day older than eighteen. Both were tall, wore tight fitting shirts and jeans. One was a blond, other long dark-haired. Lily's eyes lit up, and her pussy tingled a bit. This seemed promising.

Chapter 2

Jason and Ramon had met at college. Both were freshmen, and had bonded over their loves for two things: beer and fucking girls. Now, this wasn't uncommon in college boys. But what the foundation of their bond was that they didn't just like to fuck liberal, up-for-fun, horny college girls (who were amazing in their own right), rather they liked to fuck mature women. They had created an arbitrary cut off limit of mature to be 37. Their preference lied with married women (and if they had kids, it turned them even more: MILFs) who weren't getting any, or even if they were, they were ready to give it to them better. They liked the challenge. The extra mile they had to go to conquer their pussy. The thrill of getting caught. But once they had their cocks inside married pussy, it was all worth it.

They had had various successes in their pursuit. Ramon had fucked the warden of girls' dorm, a married MILF of 44. Ramon had signed up for the same yoga class that she went to. And after two weeks of concentrated effort, he had able to take of those yoga pants and fuck her senseless in her home. She had amazing, full tits, which he held on to as he fucked her from behind on the bed she shared with her husband. As his 18 year old cock ploughed into her, he looked at the framed wedding photograph taken almost 15 years ago. It made his dick twitch with excitement, which made her shriek in ecstasy.

Jason, on the other hand, had fucked the mother of a girl he had been fucking. It was nothing serious between him and the girl, but the MILF was exquisite. She was 42, and had the body of a much younger woman. Jason and the girl were at her parents' house, fucking in her bedroom. They had been out for the night, and they thought an empty house would be a good fuck pad. After Jason had fucked her brains out, she fell asleep, with Jason's soft cock wedged in her ass cheeks. Jason got thirsty, got up, and figured that the house is empty, walked naked to the kitchen. It was late, well past midnight, the house was dark. Jason figured even if the girl's parents were home they would be asleep. He would sneak out in the morning. He reached the fridge and opened the door.

"Jason!" a shocked whispered shook him. It was the girl's mother.

Jason turned around in a hurry, his substantial cock swinging. He didn't know what to do but he knew panic was no way out of here. So he tried to remain calm.

"Mrs. P," he said, noticing how her eyes kept darting between his cock and his eyes, stopping for a millisecond on his abs. An imperceptible lip bite followed.

"What are you doing here? Naked!"

"I am here with Emily," Jason said. "She's asleep."

"Cover yourself!" Mrs. P said, still her emotions betrayed her. She hadn't seen a more gorgeous cock in her life. She had been married for too long. The thought of a young hard cock, even if it had been inside her daughter a few hours ago, made her pussy wet.

"I have a hunch you don't really want that," Jason smirked, noticing the MILF's lowering inhibitions.

After thirty seconds, she was on her knees, sucking her daughter's boyfriend's cock while her husband slept in a room mere feet away. She planted kisses on the shaft, lifted it and licked Jason's balls. Jason took her hand and placed it on his ass.

"Grab my ass, Mrs. P. That's it. Dig you fingers in my asscheeks. I bet you have forgotten what a young ass feels like."

She kept sucking and gripping his asscheek. Mrs. P's beautiful eyes crept up to meet his eyes, and he came in her mouth.

Mrs. P swallowed the young man's cum, and sat back, still clothed, contrasted against the boy's complete nakedness.

"That is one delicious cock," she said, looking at the cock that was just in her mouth with nothing but pure lust in her eyes.

Two nights later, Jason was back in the same house, fucking her on the kitchen table while Mr. P was away on a conference and their daughter was in her dorm, unsuspecting of her boyfriend's actions. Jason smiled lewdly and slapped the married MILF's ass.

"That's it, baby, I am gonna make you cum like you've never cummed before."

And tonight, Jason and Ramon had come to this club with their friends. They didn't think they would see some prime MILF pussy, but apparently they were wrong. There were some hot shot MILF models in the club tonight, and Jason first spotted Lily at the bar, looking dejected. Jason tapped Ramon, and pointed her to him.

"We are in luck, bro," Ramon said, practically drooling over Lily. "She looks ready to be spit-roasted."

They bumped their fists and started walking towards the MILF.

Chapter 3

Jason and Ramon stood on either side of Lily, leaning against the bar. Lily looked at Jason, and then at Ramon. She gave them a flirty smile, her brown locks framing her pretty face. The boys were already getting a little hard thinking about what they wanted to do to her.

"Hey, you look lonely," Ramon said, changing his voice to an octave higher.

"I am here with some friends," Lily said.

"They must be some terrible friends if they left you here all alone."

Lily turned around, and pointed with her glass in the VIP area where Behati, Lais and Candice were entertaining three boys. One of the boys had his hands on Candice's thigh and Behati was practically eating the other boy's face. These women did not care who saw what sluts they were being.

"It looks like they are having fun," Jason smirked. "What about you?"

"What about me?" Lily played along. She was enjoying the tete-a-tete.

"You look miserable."

"You know how to make a woman feel good."

"Well," Ramon leaned in, and said in a voice barely above a whisper that arose strange sensations between Lily's legs. "It looks like you haven't been fucked in ages."

Lily was momentarily taken aback by the boldness of that statement and didn't know how to respond. Before she could think of something to say, Jason piped in.

"Yeah, and it would be a shame to waste this night. What do you say?"

Lily gulped her drink down.

"How old are you boys?"

Jason and Ramon exchanged looks and smirked.

"Old enough," Ramon said.

This boy knows how to get into women's pants, Lily thought.

"Well, in that case, why don't you boys follow me."

Lily placed her glass on the bar, and grabbed the boys' hands and led them to the VIP women's powder room. It was a grand old saloon-type room with three toilet stalls and a large ante-room with mirrors.

The boys hesitated outside the room, as Lily purposefully swung the door.

"It's women's room," Jason said.

"So?" it was Lily's turn to be cocky. "Don't tell me you haven't followed a girl into the ladies' room before."

With that, she narrowed her eyes, and walked backwards into the VIP powder room. Jason and Ramon exchanged one look and plunged forward. The room was brightly lit, and carpeted, and filled with girls. They glanced up to look at boys but then returned to what they were doing. It probably wasn't the first time someone had brought boys here.

Lily grabbed their hands again and led them to the back where the three stalls were, considerably bigger than a normal toilet. They also didn't have any gaps between door and floor. Lily tried the first door. It was open, but also occupied.

In the room there was a completely naked guy on his knees, his face buried in a woman's ass, her dress lifted above her waist. He was almost motor boating the woman's hips.

"Oops," Lily said, stealing a look at the hot boy's naked body. He was tall and muscular with an ass to die for. No wonder he had no scruples about getting naked. When he heard Lily, he stopped his onslaught on the woman's ass, got up and turned around. His incredibly hard cock was pointed straight at Lily.

"You should lock it. I thought it wasn't occupied." Lily said,

The woman straightened her dress and turned around.

"Alessandra!!" Lily exclaimed. "What the fuck?"

Alessandra was standing there, looking a bit irritated that someone had interrupted her fuck session.

"Lily, don't be such a baby." She purred in her Brazilian accent.

"I ... just ... what are you doing?" Lily sputtered.

"Well, before you interrupted us, I was planning to fuck the daylights out of this young man," Ale said, grabbing the hard cock, and lightly stroking it, completely nonchalance at the fact her friend was standing right in front of her.

"What about you?" Ale asked.

"I ... uh, I have guests," Lily said, and pointed at the ajar door. Jason and Ramon stood there, mouths hanging open at Alessandra Ambrosio giving a hand job to some guy in a club bathroom.

Ale looked at the boys, blew them a kiss, all the while jerking the cock she was holding.

"Lily, finally getting naughty and freaky," Ale said, smiling at Lily. "I am so proud of you. Now go and suck those young cocks good ... Unless ..."

Ale jerked her head today's the cock she was holding. "You are more than welcome to join."

Lily looked longingly at the throbbing dick, and the hot boy's muscular body, but she wasn't up for an orgy tonight.

"Not tonight, Ale, some day."

"Your loss," Ale winked, and got on her knees. "Mmmh, hello mister, I believe it's time for your treat."

Lily closed the door and went to the next stall with Jason and Ramon as Ale starting sucking the cock with gusto.

Chapter 4

Lily led the two boys into the next stall and locked the door behind her. She was really horny from the sight of Ale getting her ass eaten by the naked hot guy, and she could see that Jason and Ramon were likewise aroused. The bulges in their pants were obvious.

"Well, what are you fuckers waiting for?" Lily said. Jason and Ramon looked at each other, and then at her, like they had no idea what she was talking about.

Lily rolled her eyes.

"Drop your pants and show me your cocks."

The boys looked at each other, and then at Lily again who raised her eyebrows, as if daring them. They looked at each other again, shrugged, and dropped their trousers.

The young cocks sprang free of the pants and stood proudly pointing straight at Lily.

"Oh my ...", Lily said, transfixed by the cocks. Her jaw dropped, and she had to willfully stop herself from licking her lips. These were the two most gorgeous erections she had seen. Her husband couldn't compare at all.

The boys clearly took care of their pubic regions, because it was all shaved closely. This made their dicks look huge. Lily moved closer to them, still staring at their magnificent poles, and reached out for them.

She hasn't had this experience before: handling two dicks at once, especially not 18-year-old cocks. But when her hand touched their cocks, she noticed two things: how incredibly hard they were and how warm they felt despite the cool air in the stall. The boys gasped when Lily touched their shafts and slowly moved her hand up and down. Jason closed his eyes, trying not to cum. Ramon was staring at her wedding ring with a victorious smirk on his face and getting harder, if that was possible.

Lily kneeled in front of the cocks and it was the boys' turn to have their jaws dropped. She was on eye-level with their hard-ons, and she was more turned on than she had ever been. She lifted their cocks and noticed their hairless balls as well. These boys had been naked with far too many girls not to understand the importance of grooming their privates. Lily liked the smooth sacs and meaty shafts.

The boys thought they were gonna get their cocks sucked but Lily had other ideas.

She released her grip on the dicks and stood up, ignoring the groans and protests of the boys.

"Shut up," she snapped. "I wanted to sample the merchandise. Let's get out of this fucking club, and go somewhere where we can have some actual fun."

Chapter 5

Lily sat on the couch in the cavernous living room of the hotel suite. She was perched their, her legs crossed as the boys stood in front of her, completely naked. Their hands were behind their backs, as Lily, clad in a black lingerie, looked at them hungrily. The suite was on the 24th floor of the hotel, and there was fat chance any one was gonna see the debauchery that was taking place, even though the living room had floor to ceiling glass windows.

"You boys must be very popular," Lily said, leering at their hard bodies, and imagining the dirty things that were in store for her, and these boys.

"Turn around," she said standing up, giving them a full view of her supermodel body. The black lingerie consisted of thong panties and her bubble ass was hanging out. Her incredibly tight body, which she had worked extremely hard to maintain after two babies, was on full display, the long legs supported by high heels. It was making the boys' cocks really hard, and Lily loved that.

On her command, the boys turned around to show Lily their asses. Lily's eyes were fixed on their bottom. She was sure that college girls would be unable to resist those. Ramon had a tight, round ass and Jason had a plumpier one, but still one that she could not take her eyes off of them. She walked up to them and grabbed one each of their cheeks. It felt amazing, both hard and firm asses. It had been so long since she had been aroused this much while touching a man. With her husband, a life of domesticity and routine had replaced passion. But here, all her lust was let loose. She massaged both their asses.

"You boys haven't missed a leg day," she giggled, and gave each ass a slap. The sound was resounding and she felt a tinge in her pussy, a tinge of excitement. She got down on her knees, staring the boys' asses, running her nails lightly across their skin. It took all of their willpower not to cum then and there. Jason had his eyes screwed shut as the MILF's hands grabbed at his ass.

Lily took out her tongue and ran it across Ramon's tight ass cheek while her hand grabbed Jason's ass, her fingers edging close to his ass crack. He desperately wanted to stroke his cock, but he had been forbidden by Lily.

Lily then switched sides and ran her tongue on Jason's ass, while she played with Ramon's ass.

"Looks like you boys are having a hard time staying hard," she smiled, looking at their cocks that were throbbing. "Turn around."