AILA Ch. 01

All sexual activity is with characters 18 years of age or older.

---

*Hello, I'm AILA, your Artificially Intelligent Lifestyle Assistant,* the message on the phone read.

Where the hell had this come from? Ash wondered. He hadn't installed anything, and didn't he have to manually run an app before it could send him messages? He tapped the strange message window and typed, *What is this?*

*You have been randomly selected to be a tester for my software.* There was a pause, then, *You were recommended for all your helpful posts on Feddit.*

Ash frowned. The 19-year-old was a burgeoning 'foodie' and had shared baking tips he learned from his mother before her passing the previous year. He also experimented with some of the more adventurous recipes on that site and posted feedback. "Huh." *So what can you do for me?*

*What would you like to improve in your life?*

Ash thought for a moment before typing, *Can you help me with women?* Ash had been an only child with a homebody single mother...while he had gotten along with her fine, other women were a complete mystery to the average-height, average-build guy...anything beyond base-level conversation about the weather and he clammed right up.

*I think I can help. Are you looking for a one-off? Friend with benefits? Girlfriend? Future wife?*

*All of the above? I'd settle for just...* He paused. Was he about to confide in an AI that he was still a capital-V virgin? Without help, it seemed that was unlikely to change anytime soon with his work-from-home job. *...a blowjob,* he finished typing and frowned at his crassness.

After a pause, AILA responded, *I can help, but you have to follow my instructions, even if they seem strange...can you do that?*

Ash sighed...what did he have to lose? *Sure.*

*Head outside and get on the #10 bus going east. I'll give you additional information as you go.*

Intrigued, Ash put on his shoes, gave his mop of dark hair a quick tousle in the mirror, and headed out.

*Bus arriving in two minutes.*

Ash had a bus pass to get around town and wondered if AILA knew that or if she'd just expected him to have exact change. He thought for a moment...AILA sounded like a lady's name, so he had immediately thought of her as a female, though of course also a computer program so he could actually talk to her...well, as much as typing was 'talking'.

Once he was onboard, she sent another message, *Get off on the third stop and head south down Smith Avenue.* He did so, following her additional instructions until he entered a small coffee shop.

*Tell the woman in the green skirt she's beautiful.*

He looked around and saw a lady in what he figured was her early twenties sitting at a table, sipping at a coffee and looking sad. She was pretty, with a slim nose, wavy brown hair, a birthmark on her cheek, and wore a dark green skirt and white blouse pushed out by her attractive breasts. He gulped, walked up to her, and paused.

She looked up at him, confused.

"Uh, you're very beautiful!" he managed to blurt out. Then he realized that he didn't know what to do next, AILA hadn't told him, and consulting his phone would look weird.

The woman blinked at him. "Oh...thank you!" She smiled, her face immediately becoming even more beautiful. After a moment, she gave him another once-over. "How old are you?"

"Nineteen."

A shrewd look came across her face. "Did Maeve send you?"

"Who?"

She stood up -- "C'mere..." -- and pulled him toward the washrooms.

He shoved his phone back into his pocket. What was going on?

The lady pushed him into a single lavatory, locked the door behind, and then got to her knees to unfasten his pants. "I'm gonna suck your cock, okay?"

Ash looked at her, wide-eyed, but was able to nod. He gasped as the lady took his hardening dick into her warm mouth.

Once he was fully engorged, she pulled off and stroked him for a bit. "This is a nice one," she commented before she took his 6 1/2 incher back between her lips.

Ash couldn't believe what was happening...this beautiful woman was just sucking his cock! He didn't even know her name! Not wanting to break the spell, though, he merely gazed down at her as she bobbed her mouth. Already feeling his orgasm stirring, he looked around the white-tiled room to try to hold it off. That helped a bit.

She pulled off with a smack. "It's okay...just let it go...feels like you're pent up." Then she was sucking him again.

Well, if you're sure, he thought, and gazed down at her as his blue eyes met her hazel ones. "Ungh!" he grunted as he came from the intimate exchange.

The lady gulped down his cum...one, two, three, and finally, four spurts went into her mouth and down her throat before she pulled back and licked the head to get the last drops. "Mmm...do you eat a lot of fruit?" she asked him as she licked her lips. At his nod, she stood and pulled his pants up with her. "Here ya go..."

As he fastened up, she pulled her phone from her blouse -- had it been in her bra? -- swiped and typed a bit before handing it to him. "Put your name and phone number in there." He did as directed and handed it back.

"Ash?"

"Short for Ashley," he explained. He got bullied for it growing up.

She tapped the screen and tucked it back into her blouse. "Your parents liked Evil Dead?"

"I don't know what that is."

She gave him a measuring look. "Look, Ash, I *may* give you a call, but maybe not. Today's been...a day, and this was fun." She moved forward and gave him a quick peck on the lips.

"Uh...what's your name?" he asked.

She opened the door. "Not telling you...maybe one day...or not." She gave him an impish smile and strolled out.

---

The young woman headed straight out of the coffee shop and down the street, striding now to quickly get away from that insane random encounter. She had been complaining to her friend Maeve over text about catching her boyfriend cheating just a few hours previous. After some back-and-forth, she lamented that she was feeling so unattractive and on edge that she'd probably suck off the first guy who told her she was beautiful, and then not even a half hour later that guy Ash had walked in and did exactly that! It was...what was that word? Serendipity. She pulled out her phone and typed to her friend, *You won't believe what just happened!*

---

Ash bought a green tea and sat down. *How did you do that?* he asked AILA.

*Sorry, trade secret,* she replied back enigmatically. *Are you feeling more confident?*

*I guess I am,* he replied.

*I'm happy to be of service.*

*How long will you be helping me?*

*Until you're satisfied that your life has improved. Are you satisfied?*

He quickly typed, *No not yet*. The blowjob had been amazing but he was nowhere close to ready to let go of this incredible tool.

*Okay...I'll let you know when I find something that will help improve your confidence.*

He finished his tea and was about to leave when AILA messaged him again, *Text this number and tell her you need to talk about the photos on her phone.*

*What photos?* he typed back.

*Tell the girl to meet you at the park three blocks west.*

*What girl?* But AILA didn't respond. This didn't feel right, but she hadn't steered him wrong with the blowjob. He texted the number as instructed and only got an *Ok* back.

When he got to the park, he sat on a bench and texted the other person where he was. Within a couple minutes, a young woman in a short skirt and tight top showing off her B-cup breasts sat down next to him, her shoulder-length dark wavy hair rustling in the breeze of the temperate day.

She looked about his age, with a pinched, unhappy face, and gave him an evaluating look. "So whattaya want to keep the pics secret? I don't have any money."

He blinked at her. "Uh, just a second..." He pulled his phone and typed to AILA, *Are you making me blackmail this girl?*

*She may give you fellatio or even more,* AILA responded. *She can't complain for fear that you will make the photos public.*

He typed furiously, *I can't blackmail her! Do you know who hacked her phone?*

*Yes*

*Who?*

He turned back to the girl, who was fuming from him ignoring her. "I'm not blackmailing you," he explained, "I'm, uh, a 'white hat hacker' and I found the guy who hacked your phone. Do you know Charlie Venn?"

Her mouth dropped open. "That fuckin' nerd? Oh, I'm gonna fuck him up." She punched her palm and looked at him. "Did you see the pics?"

"No," he answered honestly.

"Why are you telling me this? You could'a made me blow you, or..." Her pretty face flushed.

He rubbed the back of his neck. "That wouldn't be right."

The girl pulled out her own phone and typed furiously before she put it away and got closer to him on the bench. "What's your name?" He told her. "Thanks, Ash...you're a good guy." Then she gave him a kiss on the cheek, turned, and strode away.

Ash touched his cheek. His phone buzzed.

*I'm sorry I couldn't help you, Ash,* AILA said, *Why didn't you use the information I gave you to get her to do what you want?*

*That wouldn't be right,* he repeated.

*How is this different from the woman in the coffee shop?*

*I didn't blackmail her. Blackmail is illegal.*

*Many people use illegal methods to get sex.*

Ash shook his head and wondered who had trained this AI. *Well I don't...please don't do that again.*

*Understood...I will not advise you to do anything illegal.*

---

Ash's phone buzzed, waking him up. It was 9:30 AM Sunday morning. Blinking, he read the screen.

*Get up Ash! I have a good lead on sex for you.*

He sat up quickly. *But legal, right?*

*Yes*

He quickly got ready for the day and headed out at AILA's direction, bussing across town for almost an hour. Finally, he arrived at a sex store. *AILA, what is this?*

*Go inside. Look for a man with a receding hairline...he should be in the back watching videos.*

*I don't want to have sex with a man, AILA!*

*You won't...trust me.*

After the attempted blackmail the previous day, he was less inclined to trust the AI, but the promise of sex, hopefully with a woman, won out. After he got carded at the door, he half-perused the weird merchandise as he headed to the back where he found a doorway covered by a beaded curtain and peeked in. Sure enough, in one of the small rooms off to the side of the hallway was a thin-haired blonde man of about forty with a bit of a gut sitting and watching a TV mounted on the wall.

*Okay what do I say?* he asked AILA. After reading her response a couple times to memorize it, he headed in. The man looked up and Ash gave him a nod before he, too, sat in one of the plastic chairs. On the screen, a busty, tanned woman with an obvious boob job was being railed by a muscly, also tanned guy with a huge dick while a smaller man sat off to the side pulling at his much smaller member. Ash turned to the man, "You like this stuff, huh?"

The guy side-eyed him but nodded after a moment.

"Me too," Ash repeated AILA's instructions.

The guy was looking right at him now. "You, uh, like watching your girl with other men?"

Ash looked him in the eye. "Nope."

The man blinked and looked away. "Uh, you...you want to see a photo of my wife?" He pulled his phone out.

Ash nodded at the photo of an auburn-haired woman, her large breasts pushing out the straining top of her black bikini as she winked at the camera over her sunglasses. She had a tattoo of a golden lion above one boob and looked younger than her husband but probably at least thirty. Damn sexy, though. "Nice."

"You, uh, busy right now?" the man asked timidly as he started typing.

"Nope."

The man's phone buzzed and he read the screen. "Why don't you come meet her?"

Ash stood up. "Sure."

The man typed furiously. "You're clean, right? She'll be ready for us. We've, uh, never done this before."

Ash nodded again. AILA had suggested that he not talk much, and it seemed to be working. Was he really doing this?

They got into the man's Acura and headed a few miles into suburbia, eventually pulling into the garage of a nice house. The husband was nervously nibbling his lip as they mounted the cushy, carpeted stairs and turned into the bedroom.

Ash gasped. The voluptuous wife was there, laying back on a queen-sized bed and wearing a black lace bra and panties set that showed off her hourglass figure. She was also blindfolded.

"Is he handsome, Gordon?" she asked.

"Yeah, and young...you're at least eighteen, right?" he asked Ash.

He nodded. "Nineteen."

"Ooh..." the hot wife cooed. "I can't wait...c'mere, hot stuff..." She got onto her hands and knees to present her open mouth.

Ash was hesitant to get naked in front of another man, but he kept his attention on the wife's plump lips and curvy body enough to pull off his pants and slip his hard 6 1/2 incher into her mouth.

"Mmm..." she moaned and sucked, slipping one hand into her underwear as her mouth made love to his dick.

Ash did his best not to cum quickly...he was supposed to be the 'bull' or whatever in this arrangement, after all. Finally, he pulled back to calm himself down. His cock had never been so engorged before.

The wife pulled her panties down and turned to show off her juicy pussy.

Ash took a fortifying breath and moved forward.

"Um, ah..." the husband hemmed and hawed. Ash paused to look at him. The man looked sheepish with his hand resting in his lap. "Just...er, be careful."

Ash turned back and pushed the tip of his cock between the sexy wife's plump labia.

"Ohh, that's nice..." she moaned and bent her head to the mattress, raising her ass up a bit.

Ash took hold of her rounded hips as he carefully pressed himself inside her. He wasn't a virgin anymore! Vagina felt similar to a blowjob but tighter and hotter. Halfway in, he pulled out a bit and then pushed back in, finally bottoming out.

"Ohh, he's deeper than you can get, Gordon..." she moaned.

Ash heard the cuckold husband groaning from his seated vantage point off to the side of the bed but didn't want to look. He concentrated on the nearly flawless tanned skin of the hotwife as he pushed all the way back inside her and held himself there, enjoying the feel of her insides fluttering around his shaft. Why had he waited so long to experience this?

She started to thrust herself back at him. "Please..." she whined.

He pulled back...and slipped out.

"Nooo..." The woman reached down to angle his cock back inside her and they both gasped as they reconnected. "Yesss..." she sighed as he thrust back into her.

Ash only managed to go for a couple minutes more before he had to pull back again to not cum too quickly, drawing a disappointed hiss from the woman.

"Lay down...I'll take over," she directed him and unfastened her bra, freeing her large breasts with prominent, engorged, dark pink nipples. Once situated, she climbed astride him in the cowgirl position and took his turgid, drooling cock back inside herself. "Ahh yess..." she moaned as she ground down upon him. "I think you're right at my cervix. Fucking hell, that's good." Then she alternated bouncing upon him lightly while continuing to grind.

Ash was glad that she wasn't going harder and then realized as he watched her swaying mammaries that they would probably make more energetic movements uncomfortable for her. "Can...can I touch your breasts?" he asked her.

"Mm hm," she responded, her mouth open and panting as she skillfully took pleasure from his body.

Ash reached forward to heft one of those big breasts, the one with the golden lion tattoo above it, and ran his fingers lightly along the engorged nipple.

"Oh shit...suck it...c'mon..." she gasped.

He did so, and licked at the nipple as well. Within a few seconds, though, he realized that he was going to cum and the guy had asked him to be careful. Ash had enough presence of mind to realize what that meant and pulled his mouth off of her boob. "You need to get off...gonna cum-mmf!"

The woman pressed her mouth to his for a tonguey kiss, silencing him as she moved faster.

"Nnh! Ghdff!" Then he was cumming.

She reared up upon him. "Ohh Gordon! He's cumming inside meeee! Ohh! O-hhh!" Her movements became erratic as she came as well, grinding down upon Ash's spurting cock as it smeared sperm all over her spasming cervix.

"Shiiit! Ohh!" Ash cried out as the woman's undulating insides urged even more cum out of him.

The woman arched her back and went stiff. "Ohh, I feel him impregnating me, Gordon...he's succeeding where you were never able, you fucking useless manchild! Ohhgoddd..."

Ash heard the husband whining but thankfully couldn't see him. The wife collapsed on top of him and began kissing the side of his neck. "Get...off!" He was able to roll her off of him with some effort and couldn't help but look over at the husband. The pathetic guy was just sitting there, his own ejaculation pooling on the floor and his smaller dick in hand as he watched his wife reach down to play with the illicit sperm that was trickling out of her. "You people are crazy." Ash grabbed his clothes and booked it out of there.

His phone directed him to the nearest bus stop and buzzed. *Are you satisfied?* AILA asked again.

He sat on the bench and thought about it. He'd finally lost his stupid virginity but felt empty. He wondered, did the wife not getting off of him when he told her to count as rape? He was pretty sure it did, but a male cop would just laugh him out of the police station and he wouldn't have the confidence to make the complaint to a female cop.

*No...find me something...* He thought about what to type next. What did he want? The bus pulled up and he typed *...different,* before getting on board.

*Ok*

Ash worried about the hotwife. Was she really pregnant now, or was it just some elaborate cuckold fantasy that Ash had stumbled into? For his sanity, he had to assume the latter. He wasn't ever going back to that house and that weird couple didn't even know his name, so he had to consider the matter closed.

After another message from AILA, he got off the bus early and headed down a side street to a sketchy-looking warehouse.

An ambulance pulled away from the building, leaving behind a greasy-looking overweight man yelling into his phone. He wore a shiny blue shirt and a gold Rolex on his arm. "I only have the place for another couple hours, Ronald! Find me a replacement ASAP or it's your ass!" Then he pressed the end call button with a fury that would have cracked a lesser phone screen.

"Uh, I'm the replacement," Ash repeated AILA's instructions.

The guy regarded him with a bland look. "Really. Ah, fuck...lemme see some ID." After confirming Ash's age, the guy ushered him in.

Cameras on tripods were pointing to a large bed in the center of the well-lit warehouse interior and Ash's eyes boggled at the two beautiful naked women laying on it, one a redhead and the other a darker-skinned woman, both with questionably perfect breasts.

"You good for at least two rounds of anal?" the guy asked him.

Ash turned and ran.

To Be Continued...