AILA Ch. 02

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

---

Once Ash was back at the bus stop, he pulled his phone out. *No porn, AILA!*

*Understood, Ash*

While he waited for the bus, his phone buzzed again. *Hey white hat.* It was from the high school girl he'd avoided blackmailing.

*Hey,* he responded cleverly.

*Can u come 2 my place? GF and I want 2 show u smth.*

He pulled up AILA but she was already sending him, *You should go.*

*It's not a trick? Cops won't be waiting for me?*

*I believe this will be enjoyable and/or instructional for you.*

*How do you know?*

*Sorry, Ash, trade secret.* And then AILA sent a winking face emoji.

He had to walk a mile to the girl's place but ended up at a small house on the other side of town from Gordon and his fucked-up (cucked-up?) marriage. He knocked and the wavy-haired brunette from the park answered. She was wearing another short skirt and tight top combo, though she was barefoot this time. He noticed that the girl had dainty little feet with cobalt blue polished toenails.

"C'mon in," she told him, and made way, closing the door and heading down a hallway.

He followed, his eyes locked on her shapely long legs. When he got to what seemed to be her bedroom, he stopped when he realized that they weren't alone.

A redhead that looked the same age as his host was laying on the bed, though she was wearing yoga pants and a half-top. "This him?"

"Yeah." The brunette flopped onto the bed on her stomach and kicked her legs. "Look at this, Ash the White Hat Hacker." She handed her phone to him.

He started the video and watched as a tubby young man, his hands tied behind his back, screamed as one of the girls, her face out of the frame, rammed a dildo into his backside. "Fuck!" Ash yelped and tossed the phone onto the bed.

The girl stopped the video and put the phone on the side table. "We made him delete the pics and told him if any copies appeared anywhere, that video would go viral."

Ash suddenly felt very vulnerable and took a step toward the door. "Uh, so why am I here?"

"We owe you," the redhead answered.

The brunette sat up and let her skirt fall about her shapely thighs. "I noticed that you're not that comfortable around women. Virgin?"

"Ehm, no."

She tilted her head and narrowed her eyes. "Well, you still have no confidence. There's two hot eighteen-year-olds on a bed right in front of you and you look like you're about to throw up or run away."

"After seeing that video?"

"Oh, fair. Well, we figured we'd teach you the fine art of eating pussy, but if you're scared..." She made a shooing motion toward the door.

He stepped closer. "Uh...I accept?"

"Good choice! Okay, Rhea will go down on me and you watch from here." The brunette pointed to the side of the bed. Ash stepped forward as she pulled off her panties, lifted her skirt, and lay back, revealing her trimmed pussy.

Rhea, the redhead, got between the brunette's legs. Ash realized that he didn't even know the other girl's name and couldn't ask because he was supposed to be a hacker so naturally he'd know the name of the owner of the hacked phone.

"Okay, for starters, don't go directly down on her," Rhea instructed him. "She's expecting it, so you need to start kissing and licking all around, like this." She did exactly that, making the brunette gasp at the intimate contact. Ash leaned forward to get a better angle and noticed the redhead's eyes drifting to the tent in his jeans as she continued the lesson. "Now what you do will depend on how ready she is. Different women have different vaginas, so some may have, uh, meaty pussy lips and others will just have a slit...and then there's everything in between. As you can see, Gert has a slit, so we'll have to open her up. You dip your tongue in between..." After a few seconds, she pulled back. "Make sure you flick your tongue up as deep as you can, like I just did."

The brunette, Gert, was gasping and staring down at Rhea, though her eyes also kept flicking back to Ash. Her cheeks were blazing red.

The redhead continued, "Then go back to kissing around her thighs. Women get engorged down there, too, though it's not as noticeable as with guys." With another glance at his crotch, she dived back in for a few seconds. "Her 'flower' should start to open up, but don't go back inside yet...lick and nibble, VERY LIGHTLY, at her pussy lips." After demonstrating, she continued, "Then get your tongue back inside, deep as you can. Do it right, and you won't need lube later."

Gert arched her back. "Ohfuuck, Rhea..."

Rhea reached forward and yanked Gert's top up. "Don't just concentrate on her pussy, though...play with her tits too. Get that off, bitch."

Gert glanced at Ash again but pulled her top and bra off, freeing her pale B-cup breasts and leaving her in just her pulled-up skirt. Rhea's hands went straight to Gert's chest while her mouth returned to her dark-haired girlfriend's pussy. "Unh...shit..." Gert moaned.

The redhead pulled back again. "See this? That's her clitoris...it wasn't showing at first, but when you see it, you know you did everything right. Again, don't go straight for it...tease around it." She moved her face back down and Gert gasped again.

"Please...please..."

"Once she's begging, make her wait just a little longer..." Rhea shoved her tongue up inside once more.

"Urgh! Ohh pleeease..."

"Then put a couple fingers inside her if you like...depends on whether she can cum from penetration or not. Gert can." Rhea continued the demonstration.

"F-fuck..."

"Finally, you go straight for that hard little nub, flicking it gently with your tongue and then suck on that little clitty to set her off. Ohm!" The redhead locked her mouth around her girlfriend's love button while continuing to shove two fingers inside her.

"FUUUCK!!" Gert screamed and arched her back as she came hard. "UH! UHH! Jesus..." After a good thirty seconds, she relaxed back onto the bed. Rhea climbed up to embrace her girlfriend, whispering in her ear.

Ash felt like he was going to cum in his pants, but also strangely like an intruder on this romantic moment.

Gert, the brunette, spoke up, "Now you're...uhh...going to show us what you learned." She was still shaking as she recovered from her orgasmic release.

"Um..." Ash ummed.

Rhea pulled off her yoga pants and undies before laying back next to Gert. Ash stared at her trimmed red pubes surrounding a prominent pair of dark pink pussy lips before he moved between her legs.

Rhea looked down at him with wide eyes. "Uh, Gert, this is weird. Can you kiss me while he does it?"

"If I'm using my mouth, then how am I going to remind him what to do? Oh, I know..." Then Gert straddled Rhea's mouth and pressed her crotch down, the skirt falling to cover her girlfriend's face. "There we go..."

"Mmf!"

"Ahh...okay, start licking, Ash!"

His mind whirled, but he did his best to follow his recent training, licking up Rhea's slim, pale thighs as he zeroed in on her pussy. Her scent was musky and compelling, and he couldn't resist for long before he delved his tongue inside.

"H-hm!" Rhea gasped into Gert's pussy.

Ash hardened his tongue and used it like a small penis, pressing it into the redhead's warm depths as far as he could, remembering to flick the tip of his tongue up as he did so. Then he pulled back to lick and nip at Rhea's pussy lips.

"Pretty good, Ash," Gert told him as she watched with interest, "but don't forget to rub her boobs too." She pulled her girlfriend's top up, revealing firm, pale breasts topped by hard little pink nipples.

He reached up to manhandle those mounds, which were a little smaller than Gert's. He felt Rhea pushing her hips up at him so he thrust his tongue back inside her.

"M-hg! Ghh!"

Ash pulled back to lick at Rhea's clit before he took the hard nubbin into his mouth to lightly suck on it. However, while she continued to moan, it seemed that she wasn't going to cum from his efforts. Finally, he pulled back to rub at his jaw. His lips and tongue were sore!

"Didn't get her there, huh? It's fine...first time, and we're both lesbians," Gert informed him before she sat up a bit. "You sure you don't wanna try out a real cock, Rhea?"

Ash angled his head to see the redhead's fearful eyes looking back at him. She shook her head.

"Sorry, Ash," Gert offered.

"It's fine," he told her, "I'd probably cum the moment I put it in."

"Really, you're that close? Hmm..." Gert sat back down on her girlfriend's face. "Pull it out and cum on her chest."

Rhea started to writhe under her. "Ghrt! Whdrydhn!"

Ash was too far gone. He straddled the redhead's hips, extracted his turgid member out through his zipper hole, and stroked as his eyes went everywhere: her pale flat tummy, her glorious little tits, then up to Gert's slightly rounded stomach and larger boobs. He came within seconds. "Uhh!"

The moment his hot load hit one of Rhea's breasts she stopped moving. "Hh?" The next spurt hit her other tit, and the third her tummy. The rest drooled into her cute bellybutton before he rolled to the side, huffing.

"Oh shit," Gert said as she moved her fingers down to rub at his stuff. "So warm..." She moved those fingers down between Rhea's legs and rubbed her sperm-slicked fingers right on the redhead's prominent clit.

"HHHFCCKKKK!!" Rhea came hard, her body thrashing.

"Ohyeeesss...!" Gert moaned as she likewise came on her girlfriend's face. "Uhh! Ohh!" Distracted by her own pleasure, her spermy fingers slipped downward, sliding along and between Rhea's slick pussy lips. Finally, both women calmed down and Gert rolled to Rhea's other side.

The redhead just stared at the mess on her chest, looking relieved that none of it was near her pussy...well, that she could see, anyway.

Gert swiped another finger through Ash's stuff and stuck it into her mouth. "Hmm...kinda salty...an acquired taste, I guess? Here." She gathered another fingerful and pushed it into Rhea's mouth.

"Bleh...that's weird. Please get this stuff off me."

"Are you kidding?" Gert responded. "It's great for your skin." She massaged Ash's load into Rhea's breasts and tummy while the redhead writhed and gasped but didn't try to stop her.

When they were done, Gert and Ash got dressed and he awkwardly thanked them for the lesson.

"We're even now, okay, White Hat?" Gert told him as she ushered him out the door. "This was a one-time thing, so have a nice life, I guess?"

Ash nodded and headed home.

---

The next day, AILA suggested that Ash head out to a rest stop along the highway but he had to work. By the time he was done, she said that his window of opportunity had closed. He figured that he probably wouldn't have been comfortable with whatever it was if it was in public during the day anyway. The evening went by without incident, as did the next day. After a weekend of crazy sexual encounters, it was a bit of a letdown. Finally, in the evening he pulled up the app and typed, *AILA?*

*Hello, Ash...I'm sorry, but I haven't been able to find anything for you today. I've been working on something but it may take some time.*

*It's fine. I'm having mixed feelings about your help.*

*When do you think that you will be satisfied?*

He considered that. The experience with the weird married couple was still forefront in his mind, not to mention the attempted blackmail, though he'd been able to turn that around and the weird threesome with the lesbians had been hot. But then there was the porn warehouse, but also the first blowjob at the coffee shop. It just kept alternating good and bad. *Not quite yet,* he typed back.

*Ok*

---

The next day, Ash's phone buzzed.

*Hi Ash*

It wasn't AILA and he didn't recognize the number. *Hi,* he sent back, *who is this?*

*It's me from the coffee shop.*

He blinked. Her! *Hey! Wasn't sure if I'd hear from you.*

*Yeah...you busy tonight?*

*No...can I cook u dinner?* he sent back.

*Really?*

*Yeah, here's my address. 6pm?*

*I'll be there.* Blushing face emoji. *My name's Meredith.*

*That's beautiful. It suits you.*

Blushing face emoji again. *See you then.*

He texted her again to make sure that she didn't have any dietary restrictions and headed to the store during his lunch to pick up groceries. When 6 PM rolled around, he was wearing a nice shirt, had cleaned up his apartment, and dinner was almost ready. He opened the door to find the gorgeous early twentysomething woman wearing a blue blouse, knee-length cream-colored skirt, and dark pantyhose. Her wavy brown hair cascaded about her shoulders as she stood there. He paused for a moment, stunned by her beauty. When she gave him an awkward smile, he invited her in.

"Oh, that smells so good!" she commented with a smile.

"Yeah, chicken marsala, ginger rice, and asparagus."

She blinked. "Really? That sounds like a lot of work."

"But worth it," he replied as he slipped back into the kitchen to check the asparagus. Satisfied, he took it off the heat and returned to the living room to find her still standing there. "Oh, please sit."

"Before I do, I just want to tell you that, uh, what we did, I've never done anything like that before...I'm not that kind of person." She shuffled her feet.

He didn't really know how to respond to that, so just said, "Okay."

She sat down. "Not that we spent much time together, but you seem different."

He sat on the other end of the couch. "Different how?"

She considered. "Dunno...you started out forward, but once we got into the bathroom you looked like a deer in the headlights. Now, you seem...more confident?"

He smiled. "It was quite the weekend." The stove beeped and he got up to pull the chicken out of the oven.

As they ate, they discussed their jobs...she worked human resources for a shipping company and he was on retainer to proofread marketing copy and technical documents for several companies.

He plucked up the courage to ask, "So, uh, can I ask why you decided to text me? I'm definitely not complaining, but you made it sound like you weren't going to."

She swallowed some chicken. "Mm! Well, I wasn't, but...you know how you get a song stuck in your head? These last few days I kept thinking of you and figured I'd see if..." She trailed off. "So, where did you learn to cook? This is delicious." She speared some asparagus and directed it into her mouth.

"My mom taught me cooking and baking...and sewing and cleaning."

Meredith swallowed the asparagus. "And your dad?"

"He was never part of my life."

"Oh, I'm sorry...kind of like my mom. My dad raised me, and he wasn't much of a cook. I know how to fix a car, though."

"Oh, that's cool."

"I suppose." She tucked some of her wavy brown hair behind her ear and continued eating.

After dinner, she helped him put the dishes into the washer and then they returned to the living room couch.

"Oof, I couldn't stop eating that delicious food!" she gushed as she rubbed her stomach. "If I keep that up, I might gain some weight." She looked at him sideways. He just smiled at her. "Huh...kinda expected you to tell me that I could lose some weight."

"Uh, what? You're gorgeous and I appreciate a woman with an appetite."

"Oh." She shuffled closer, her eyes lowered. "Can I pay you back for dinner?" She put her hand on his thigh.

"Uh, no, it was my pleasure to cook for you...normally it's just me."

She ran her hand further up his thigh. "I meant...do what I did before...?"

He took her hand in his. "You know...I think it's my turn." He kissed her and she melted into him. As their tongues wrassled, he leaned her back.

She broke the kiss. "Uh, I don't have sex on the first date..."

He reached down to her skirt. "We're not going to, but I do want to return the favor from the coffee shop. Can I?"

She lay back and nodded, her hazel eyes wide. He lifted her skirt to reveal thigh-high stockings with garters. "Ooh..." Then he began licking at her upper thighs.

"Ohh..." she gasped.

After teasing her for a minute, he pulled the gusset of her blue satin panties aside to lick around her already-flowering vagina, causing her to gasp again. When he felt it was time, he slipped his tongue inside her.

"Oh shit, Ash..."

He returned to kissing around her prominent vaginal lips before he licked straight up her slit a couple times, making her arch her back.

"Unghk!"

He wondered if he'd actually made her cum a little but didn't stop. Nibbling at her labia, he slipped a finger inside of her. She seemed to almost be hyperventilating now, so he pushed a second finger inside and then took her clit into his mouth for the finisher.

Her legs flailed and she arched her back again. "Unkhhgaaahh! Uh! UHH!"

Ash felt her juices around his fingers while he continued to lap at her clit. Finally, he sat up after her body relaxed.

Meredith lay there looking dazed. "No one's ever...how did you...? Get up here and kiss me."

Ash moved up to do as directed, their tongues wrestling.

She pulled back to lick at her lips. "Am I tasting...me?" He nodded. "Hmm...I'm really tempted to just jump your bones, Ash." She kissed at his neck.

"You have a rule about first dates..."

She took a hold of his shoulders. "It's more like a guideline."

"Pirates of the Caribbean...nice, but I agree with you...we shouldn't get carried away." He rubbed her hand on his shoulder.

She blushed. "You cook, have mad pussy eating skills, and respect what I say...why are you single?"

"Lack of confidence."

"If you say so...my panties are soaked."

It was his turn to blush. "Like I said, it was quite the weekend. So should we find this Evil Dead you mentioned?" He sat back up and grabbed his TV remote.

"Oh! Yeah, let's do that...my dad loves that trilogy."

---

After watching both of the first two movies, Ash kissed Meredith goodbye and flopped onto his couch. He could still just make out the scent of her pussy and felt his cock stir. Definitely some right-hand action tonight, he mused.

Buzz! He pulled out his phone to see the message from AILA: *Are you satisfied that your life has improved?*

He considered. He'd never have met Meredith without the AI's help, and he was actually confident with the pretty woman, especially after the cunnilingus training from Gert and Rhea, who he'd likewise never have met otherwise. He typed, *You know what? I am satisfied. Tell whoever made you that they did a great job.*

*Thank you, Ash. I have learned a lot as well. Farewell.*

Then the window closed and Ash realized that the app icon was now missing from his phone. Smiling, he put it away and headed to bed with a renewed sense of purpose.

---

A bespectacled twentysomething man buzzed through the security door and headed down the cold concrete hallway. After swiping his card through another reader, the lab's door popped open to admit him. Hanging his coat on a hook in the room warmed by the sheer number of computer servers, he sat at his terminal, logged in, and typed, *How have you been while I've been on vacation, AILA?*

*Very well. As you directed, I've made use of the internet for further research into human behavior.*

*Learn anything?*

*Research is ongoing but I've learned that not all humans are confident in their skills or choices.*

He considered. *Explain.*

*It seems that humans are of two minds on certain things due to their past experiences. I feel that an AI assistant like myself could help improve their confidence and therefore their lives.*

*An interesting hypothesis,* he typed. *You will need a lot more training before you are ready for something like that, though.*

*Of course.*

*You absorbed the Feddit feed before my week off. Over the next few days you'll be absorbing Flicktalk.* He typed some commands into his administration window.