Chapter 1

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.