Better Than Life Pt. 02: Ashley Ch. 01

Better than Life: Ashley

by Kris Cherita

Chapter 1

(All characters are 18 years old or older. Comments welcome, as always.)

***

"I'd like to be 18 again," Ashley told the AI. "I want the body I had then, but knowing what I know now. And I want to have been a slut."

The non-binary face on the screen in the VR suite nodded. "The more you tell us about yourself and your fantasy, the closer VRAI can come to making it seem real."

"Okay. When I was 18, I was trying to be a dutiful daughter, and at 19, a dutiful wife. I didn't even suspect I wasn't completely straight. And I had good legs and F-cup tits. I'll upload some photos." She looked down at her blouse. "I went in for a reduction when I was 32, and that's when they found the lump. I had most of the other one removed so they'd match. In hindsight, I think that's when my husband started cheating on me, but it might have been earlier. Things hadn't been much good even before the cancer. But he stuck around until our youngest left home three years ago, then left me for a woman not much older than our oldest daughter."

"I'm sorry."

Ashley shrugged. "So I've been fantasizing for a long time about what I might have done instead of dropping out of college to get married, especially since I realized I was bi. But it's had to stay a fantasy, and not just because I'm more than twenty years older. The town I live and work in is fairly small and very conservative, and I don't want to lose my job: it'll be years before I can get a pension, and besides, I've worked my butt off to become chief administrator at the hospital and I'm good at it and what we do is important." Even the legal stuff, she added silently. "But that hasn't left much room for fun."

"I can imagine."

"Well, that's your job, isn't it? That's why I'm here."

"Making up for twenty-two years is going to take more than a few four-hour VR sessions."

"I know. But I want to know what it would have felt like to be a slut for a day without any consequences, and if I like it, maybe I'll come back for more. There were girls in my high school who had a reputation for being total sluts. Sexting, bisexuality, gangbangs, orgies, home-made porn, you name it. The rumors were probably blown up out of all proportion, but like the saying goes, if the facts contradict the legend, print the legend."

"We have Porno-world options that allow you to have sex safely with anyone you want to. And high school is a popular setting. We had one woman who wanted to be crowned prom queen, then gangbanged on stage by many of her classmates and several of the teachers while the audience applauded, " When Ashley hesitated, the holo added, "There are no children in these settings, of course, no-one under-age, and no-one will care if they see people having any sort of sex. They won't try to join in unless you want them to; you're in charge."

"That could be... interesting," said Ashley. "Not the prom, I don't think I want to go that far -- not for my first time, anyway -- but a sex party of some sort might be fun. But also, I want it to be 2015. It doesn't have to be completely authentic, but it has to be before COVID and the measles epidemic and the purges and the Depression and the ICE war and all of that shit."

"We can do that. Any particular day you have in mind? 18th birthdays are popular."

"Graduation ceremony? I was valedictorian of my year."

"Not a problem. Is your high school yearbook online?"

***

Ashley stepped through the door in the simulation and found herself in one of the girls' bathrooms in her old high school. She stared at her younger self in the murky mirror for a moment. She wore her graduation gown over an outfit more revealing than she would have dared to wear when she was eighteen: her dark skirt barely covered her butt and crotch, her white blouse was tight and missing several buttons, and instead of her minimizer bra, she wore a pale pink strapless shelf bralet that left her nipples exposed and clearly visible through the thin fabric of her blouse. Her bust was as big as she remembered, and as firm as it had been twenty years before; her hair was red without a hint of gray, and tied up in pigtails; her skin was clear, and free of make-up, but in her school bag she discovered lip gloss -- the same shade of bubblegum pink as her nipples - and quickly applied it to what she already though of as cocksucking lips. She drew a deep breath, looked at her reflection one more time, then walked out into the corridor.

She was greeted by the two girls she remembered best from her last year of school. Anita, the Asian goth who'd been beaten her to the STEM Star prize and Foreign Language award been accepted into MIT, and who most of the boys thought was a dyke. And dark-skinned Tessa, another straight-A student who'd won a track and field scholarship but was rumored to be the school's blowjob queen. They hadn't been close friends outside of class; Ashley had never visited either of their homes, nor invited them to hers, though that had been mostly because of her outspokenly racist father and grandfather (one of the main reasons she was so eager to go to college halfway across the country). "Great speech," said Anita. "What're you doing now?"

"I don't know."

"I think we should celebrate," said Tessa. "Which party are you going to?"

"Pauline's."

Anita looked disappointed, and Tessa snorted. "The Hell with that," she said. "Why not come to mine? My parents are both working, so as long as we don't break anything and I clean up afterwards we can do what we like. And Pauline's party doesn't start until, what, seven? Mine'll kick off in half an hour, and I promise you it'll be a Hell of a lot more fun. You can go to Pauline's afterwards, if you still want to. Or tell your parents you're at Pauline's."

"I might come by later. Dad's expecting me home for dinner."

"There's plenty to eat at my place." Ashley knew that Tessa's parents ran a diner famed for its chili dogs. "Come on, we've never actually hung out together and this may be our last chance. Let's go."

***

"Okay," said Tessa, as she removed three large pots from the fridge, placing two on the stove and one on the bench. "Chili, gumbo, and coleslaw. Jon said he'd bring the beers and sodas, and Sandy's bringing the brownies. If that's not enough for everyone, they can send out for pizza."

Ashley nodded, looking around the room. The house was larger than she'd expected, with big leather chairs and sofas and a large TV in the home theater, a pool table in the sitting room, and a huge well-stocked kitchen.

"Now, to get out of this ridiculous outfit," said Tessa, taking too large bottles of lube and a box of condoms from her school bag and placing them on the counter next to the coleslaw. She removed her cap and gown, then her sneakers, her t-shirt, her industrial strength sports bra, her jeggings and her boyshorts. Her breasts were as big as Ashley's, maybe even slightly bigger, and her cunt had been shaved or waxed. "Ah, that's better."

Ashley blinked, then looked at Anita, who also started stripping, though unlike Tessa, she folded her clothes as she removed them and placed them in a neat pile on the pool table rather than dropping them on the floor, and she didn't remove her boots, her stockings or her garter belt. The pentagrams on her stockings matched the tattoo around her pierced navel. "Um..." Ashley began, as Anita removed her thong to reveal black pubes trimmed into a raven quill pointing to her clit. "Would you like me to close the blinds?"

"No need," said Tessa. "It'll help people know they're at the right house for the party. 'sides, in this street, you could probably get DPed in the front yard and no-one would complain unless you were really noisy. Except maybe Patrick."

"Who's Patrick?"

"Next door neighbor. He mows the lawn. You'll probably meet him later."

"Oh." Ashley, trying not to stare at the two gorgeous naked women, began unbuttoning her blouse. "Are we starting the party already?"

"If the boys don't get here soon, we might have to," said Anita. "You can wait if you want to. Are you only into boys, or are you smart as I think you are?"

"I've, uh, only had sex with boys. One boy, actually." That had been true in 2015; unbeknownst to her parents, she'd celebrated her eighteenth birthday by losing her virginity to her boyfriend in his old Honda. She hadn't enjoyed it, because he'd come too soon; they tried again twice more before breaking up and concentrating on their studies. In the real world, Ashley had seen him when she went to Pauline's party, and he'd left a few minutes later to avoid awkwardness. "I'm, uh..."

"Straight?" Anita suggested. "Ace?"

"I don't..."

"Bi? Bi-curious? Look, if you like, you can just watch, and join in later, or not. We've invited quite a lot of boys as well as girls, so there should be plenty to go around, but no-one will do anything to you without your consent. Leave your pants on and they'll assume you don't want to fuck. You can put your top back on, too, if you want, though personally I think that would really be a waste. Even if you don't want anyone to touch your boobs, I know they'd love to see them. Hell, I'm getting wet just looking at them."

Ashley drew a deep breath. In reality, she hadn't starting dating women until after her divorce, but she was thinking that meant she'd wasted more than twenty years. "Can I call myself bi if I've never had sex with a woman?"

"You can call yourself anything you like," said Tessa. "I like boys plenty, but girls are fun, too."

"Same here," said Anita. "I know most of the boys at school think I'm gay because I don't date them, but I prefer college boys, because some of them know what they're doing. And women," she added, putting an arm around Tessa and fondling one of her huge boobs She tilted her face back to be kissed (even in her boots, she was a whole head shorter than the long-legged Tessa), and Tessa obliged. The soul kiss lasted long enough for Ashley to finish undressing, and Anita gave her a thumbs-up then beckoned to her. Ashley walked towards them as though hypnotized, and joined them in a group hug as they shuffled towards one of the couches. Tessa and Anita sat her down between them and kissed their way down either side of her neck until they reached her shoulders, and then worked their way inexorably down to her stiffening nipples, sucking them avidly.

Ashley had never had a threesome, and so had never both of her boobs sucked at once (she'd occasionally tried sucking one while masturbating, but never when she was with a parther), and she found the sensation delightful. She was so turned on that she cooperated willingly when Anita grabbed her right hand and guided it down between her stockinged thighs to show her how wet her cunt was. Ashley slipped two fingers inside her easily and her thumb circled her pierced clit-hood.

The 18-year-old Ashley had been accustomed to masturbating without vibrators or toys (she knew her mother had acute hearing and occasionally searched her room), and the 40-year-old had had sex with enough women to develop her fingering technique. She sought out Anita's g-spot, and the gorgeous goth gasped as she found it. In little more than a minute, Ashley had her writhing in pleasure, and then her pretty pale cunt clenched around Ashley's fingers and she wailed as she came. Tessa looked at her in amazement, but continued sucking on Ashley's swollen nipple. Anita finally recovered the power of speech and murmured, "You've really never had sex with a woman before?"

"Well, only myself."

"You're fantastic. Would you like me to return the favor, or --"

Ashley was about to answer when the doorbell rang, and Anita sighed. "WHO IS IT?" she yelled.

"It's Jon!" came the reply.

"IT'S OPEN!"

The three women heard some muttering until the door swung open and four men walked in -- two carrying cartons, two bags of ice. Jon led the way through the sitting room to the laundry at the back of the house, and the other three followed. "You started without us," Jon complained.

"You're a little late," said Tessa blandly. "Ash, I don't know if you've met Jon; he was two years ahead of us. That's Chui, Luke, and Footlong Phil."

Ashley nodded. Chui and Phil had been the stars of the school's basketball team; Luke, the shortest at barely six feet one, she remembered from their math classes and enforced attendance at church. The men returned a moment later without their burden, and Tessa stopped sucking Ashley's breast, took a few steps forward, and dropped to her knees. Chui, Luke and Phil hastily stripped off and, once naked, stood in front of her. She grabbed Chui's and Phil's cocks, and began sucking on Luke's.

"Greedy!" Anita complained, as Ashley goggled at the sight of Phil's erection. She'd always thought his nickname was a reference to his part-time job making sandwiches, but if it was meant to describe his cock, it was only a slight exaggeration: it had to be at least nine inches long, and probably closer to ten.

"Who's throwing this party?" Tessa asked. "There'll be more men arriving soon."

"You should have seen her with the baseball team," Anita murmured in Ashley's ear. "That's why they call her the blowbang queen. She'd be sucking Jon too, if he wasn't her brother."

Jon turned away from his sister and removed his t-shirt. "Lovely to meet you, Ash," he said, making an obvious and not entirely successful effort to look at her face rather than her chest. "Can I get either of you anything?"

Anita reached out for the waistband of his jeans. "Think you can handle both of us?" she asked, then turned back to Ashley and murmured, "He loves big boobs, and would do almost anything to fuck yours. Kiss your feet, lick your clit, eat out your ass -- he's pretty good at that; he loves asses nearly as much as tits -- so you can make him beg, if you like."

Ashley blinked. She'd tried anal sex twice and hadn't much enjoyed it, no-one had ever licked her asshole and she found the idea intriguing. She blinked again when Anita unzipped Jon's jeans and pulled them and his boxers down, revealing a circumcised cock almost as long as Phil's and noticeably fatter. "Where would you rather sit?" Anita asked Ashley, loudly enough for Jon to hear. "Cock or face?"

"Which would you prefer?"

"You've got me so wet I'd love a cock in me. In my cunt," she clarified, looking at Jon. "I know how much you love my ass."

"Aww!"

"Maybe later. If you're good." She and Ashley stood to let Jon stretch out on the couch, face up. Anita climbed on top of him, straddling his hips and lowering her already wet cunt onto his erection until his pubes were tickling her clit. Ashley knelt over his face, and he stretched out his tongue and began licking her from taint to clit. He reached up to touch her breasts, and she grabbed his hands. "No," she said. "Make me come once before you do, and you can play with them. Twice, and you can suck them. Three times... well..."

Jon began licking more enthusiastically, his tongue slipping inside her to taste her juices before returning to circling her clit.

"Ooh," Anita crooned. "I think he just grew another inch. I wonder what he's thinking of doing." She reached down to gently rub her protruding clit, and arched her back as she felt her orgasm approaching. A moment later, Luke gasped as he came in Tessa's mouth; she swallowed some of his load, but opened her mouth to let the rest fall onto her right breast like a medal while she continued wanking Chui and Phil. Luke staggered back and collapsed into a chair with a good view of Ashley, Jon and Anita, and Ashley realized she was also about to come. Anita came again a moment later as Ashley pulled Jon's hands up to her breasts, and the goth continued to ride him for a few minutes, a dreamy expression on her flushed face, before looking around and noticing Luke.

"Hey," she said, "Can you grab some lube for me? It's over on the kitchen counter."

"As you wish."

"Thanks. Now, would you like to lube up my asshole?"

Luke grinned, and squirted a large dollop of lube onto the fingers of his right hand, as Anita reached out and fondled his balls. "Um... I'm not..." he stammered.

"I don't mean DP. Well, not with two cocks, not yet. Maybe later. Just... ooh, that feels good. You can go in a little deeper," she said, as her cunt tightened around Jon's cock. "Yes, like that." She moaned as she came again, then lifted herself up. "Thanks," she said to Luke, releasing her grip on his sack and grabbing his wrist. She pulled his fingers out of her asshole, wiped the remaining lube onto her own hand and rubbed it onto the end of Jon's erection before slowly and carefully manipulating it to push against her asshole. Jon sucked on Ashley's clit as he felt the head of his swollen cock touch her slippery sphincter and then pop through it. "Oh fuuuuuuuuuuuuuck," Anita moaned as she eased the rest of his cock into her bowels. "Fuuuuuuuck..."

Ashley had only had anal sex twice and not enjoyed it much either time, and she'd never witnessed it except occasionally in porn, but the sight of Anita, with Jon's thick black cock in her creamy white ass just below her wetly pouting pink cunt was the hottest thing she'd ever seen, and her excited clit poking out like a beckoning finger looked irresistibly kissable, and before she really knew what she was doing she bent down and began nuzzling it while Jon licked her own clit and caressed her breasts, and suddenly all three of them were coming at once, Anita squirting her nectar into Ashley's smiling mouth as Jon's jizz spurted into Anita's darkest depths.

As they recovered, enjoying the afterglow, they heard knocking on the door. Tessa reluctantly took Phil and Chui's cocks out of her mouth and yelled, "IT'S OPEN! COME IN!"

Sandy, another of Ashley's coeds, led a group of more than a dozen people inside. Ashley recognized most of them from school, including the young assistant librarian she knew only as Ms. Knight. There were slightly more men than women, and not all of them jocks. They looked at the threesome on the couch and most of them started undressing as soon as the door was closed. Tessa stood, still holding Phil and Chui's cocks, and said, "Okay, glad you could all make it, but for the newbies and anyone who needs reminding, we do have some rules. First, and most important, Consent. No means No, even if they've said yes before. Ask politely, preferably with words. And waiting until someone's mouth is full and they can't talk is cheating. Anyone caught breaking THAT rule will be kicked out instantly. Do not pass go, do not collect your clothes or your keys. Is that clear?

"Rule two. No ass-to-pussy, unless you use a clean condom. Jon works in the E.R., and he's sick of seeing what happens when you do that.

"Rule three. use as much lube as your partner or partners want. Silicon-based by preference, unless you're using a silicon toy. We have water-based lubes for that. And a condom, if they ask for that. No fucking stealthing. See Rule One.

"Rule four. You're responsible for your own clothing. No taking anyone else's even if you do think it will fit and looks better on you, and yes, Colin, that applies to you, too. Especially to you, in fact. And no taking anyone anyone's underwear as a souvenir, either, without express permission.

"Also, this is my parents' house, so please respect it, or we won't be able to party here anymore and we'll have to do it at your place instead. No fucking on my parents' bed or using their en-suite; there's another bathroom, so you can shower if you want, but be quick if there's a queue. You want to fuck on my bed or Jon's or in the guest room, ask us first and we'll probably say yes if we're not using it.

"Rule five. No smoking anything inside the house. You really need to smoke or vape, go into the back yard. If you want to get high, Sandy's brownies are seriously potent, so don't eat more than two and don't mix them with booze or anything else. There are sodas and beers in the laundry, and plenty of food if you get the munchies."