AI Girlfriend

The venue for the fourth date was a wine-tasting party in a Manhattan penthouse. The dress code was “Avant-Garde Cocktail.”

The good news was this dress wasn’t some anime costume. The bad news was tonight’s outfit was a slip of purple silk that was less a garment and more a suggestion. It had a slit that went all the way up to her hip bone, held together by a fragile silver chain. The back was entirely open, dipping dangerously low. It was elegant, expensive, and incredibly exposing.

Kurumi-san hadn’t shut up about it since she saw it. “You’re so beautiful, Kurumi-chan!“ she gushed. “I wish I could look as beautiful for David-sama as you do.”

“You do,” Grace said, reflexively consoling her virtual friend. “We’re both Kurumi, right?”

“You’re so right, Kurumi-chan! You’re as wise as you are beautiful!“ Grace smiled at the compliment.

“And just think of the way that David-sama will look at you, with those commanding eyes and his big powerful demeanor.”

Grace did think about it. In fact, she had to admit she’d been thinking about it a lot lately. Her nipples were already a little hard. Tonight was going to give her more fuel for her evening sessions, she was sure of it.

When Grace walked into the gallery, she felt the eyes on her immediately. The contrast was stark: the room was filled with women in beige and cream, men in charcoal suits, and here she was—a slash of purple silk and vibrant violet hair. She felt like a beautiful flower in a garden of weeds.

Her phone buzzed. Grace checked it to make sure it wasn’t from David, but it was just her mom calling again.

They’ll never forgive you if you tell them,” Kurumi-san said. Grace knew she was right. She declined the call, then put the phone on silent. She hadn’t figured out a way to talk to her parents about what she was doing.

A moment later she found David waiting by a sculpture made of twisted metal. He wore a velvet tuxedo jacket, his bald head gleaming under the track lighting. He looked powerful. He looked like he owned the building. Maybe he did.

“David-sama,” Grace purred, gliding up to him.

David turned. His eyes raked over her, starting at her heels, traveling up the slit in her dress, lingering on the curve of her tits, and finally meeting her violet gaze.

“Kurumi,” he said. “Stunning.”

Grace felt the warmth in her chest intensify with the compliment. She felt herself blushing, and looked down demurely. “Arigatou gozaimasu.”

He handed her a glass of dark red wine. “Cabernet. Heavy tannins. Complex.”

Grace took the glass, her fingers brushing his. “Like you,” she said softly.

Before David could respond, a tall man in a linen suit approached them. He was holding a glass of white wine.

“David!” the man boomed. “I haven’t seen you since the merger.”

David smiled. “Sebastian. Good to see you.”

Sebastian turned his gaze to Grace, his eyebrows shooting up. “And where on earth did you find such a… colorful creature?”

Grace felt a spike of anticipation. She had spent the last week memorizing the Kurumi Bible—the backstory, the favorite foods, the childhood memories. It was all there, filed away in her brain right next to her own memories.

Grace offered a small, demure bow and looked to David, who gave her a small, brief nod. Permission to speak.

“I am from Tokyo,” she said, her voice soft and high pitched. “I grew up in Akihabara.”

“Tokyo! I should have guessed.” Sebastian beamed. “How long have you been stateside?”

“Two years,” Grace replied. “New York is very different from Akihabara, but David-sama makes it feel much less overwhelming.”

“Tell him about the maid café you worked at,” Kurumi-san prompted. “Use the word ‘Goshujin-sama’.”

“In Tokyo, there is a quiet beauty in knowing exactly how to please your Goshujin-sama. New York is so loud and everyone is fighting to be noticed, but I find it much more peaceful to simply focus on David-sama’s needs.”

Sebastian nodded. “Well, it seems David is a lucky man. And I must say, the accent is delightful.”

Grace froze. Accent? She hadn’t realized she was doing one. It wasn’t intentional, it was just… seeping out. The cadence of the anime she’d been binge-watching, the rhythm of Kurumi-san’s voice in her ear—it had infected her speech without her noticing.

“Arigato,” Grace said, looking down shyly. “You are very kind.”

“You’re doing so good!” Kurumi-san chirped. “I didn’t have to tell you any of that! I told you, you’re a natural at being Kurumi!“

David stepped in then, placing his hand on her lower back, a signal that her time to talk was over. “Tokyo has a discipline that New York lacks,” he said. “Here, everyone is just looking out for themselves. There, people understand their role in the greater structure. Kurumi understands that.”

Grace looked up at him. He had just reduced an entire culture to a talking point about obedience. About how people should know their place. And no doubt, he thought his place was at the top. It was offensive. And the real problem, as Grace saw it, was that he was right. When you were as powerful as David, was it even still arrogance?

“Kurumi is a quick learner,” David continued smoothly, dismissing Sebastian with a glance. “But we prefer to keep our circles small. If you’ll excuse us, Sebastian.”

He steered her away, his grip firm. He didn’t say anything, but he looked down at her with genuine surprise. He was impressed at how well she’d handled the conversation, and the weight of his approval felt better than the wine. Grace felt herself getting turned on.

The evening continued, a blur of expensive wine and hushed conversations. Grace found herself watching David, really watching him. She liked the way he swirled his wine, the precise, controlled movements of his hands. She liked the way he cut through other people’s bullshit conversation with sharp, cynical observations.

“He’s magnificent, isn’t he, Kurumi-chan?” the original Kurumi whispered in her ear. “Such strength. Such confidence. A true pillar of a man. David-sama could crush anyone in this room, yet he chooses to be gentle with you. We are special to him. You are special.”

It was true. Grace looked at David as he finished a conversation with a nervous-looking man, his gaze locking onto hers. He was handsome. Plus, he did seem to possess an almost overwhelming power, and the fact that he was focusing it entirely on her made her feel special, chosen.

By the time they left, the city air was cool against her flushed skin. A long black limousine was waiting at the curb, the driver holding the door open.

Grace slid onto the plush leather seat, still light headed from the champagne. David slid in next to her, the door closing with a heavy thud that shut out the noise of the city.

The partition was up. They were alone in the dim, private world of the car.

David loosened his tie, looking at her. The streetlights flashed by outside, illuminating his face in regular intervals. “You were perfect tonight,” he said. “Obedient. Beautiful. Everyone was looking at you.”

“I only care if you look at me, David-sama,” Grace whispered, the alcohol buzzing pleasantly in her head.

David sighed. “I wish you were really her,” he whispered. His voice had a wistfulness Grace had never heard before. He’d never broken character until that moment, she realized—never let on that Grace wasn’t the “real” Kurumi. But wasn’t she? Right now, sitting next to him in the limo she felt like Kurumi. She wanted David to see that, to know he wasn’t talking to Kurumi-san right now. He was with her, with Grace, with Kurumi-chan.

“I am her,” Grace whispered back. “I’m right here.”

She shifted in the seat. The purple silk rode up higher on her thigh, exposing more skin to the cool air of the cabin. She leaned back, pushed out her tits, and watched as his eyes locked onto her body. Even David, a seemingly master of self control, couldn’t help but stare.

Her nipples were hard against the thin silk, aching for his hands. Her pussy was wet, soaking her panties, aching for something else. She was ready, her body betraying just how much she wanted this strange, intense man to take charge.

She waited. She waited for his hand on her leg. She waited for him to grab her waist, to rip up her expensive dress. She waited for the “alpha” behavior she’d found so boorish before. But now that she wanted it, he wasn’t moving.

“He’s holding back,” Kurumi-san whispered in her ear. “Look at him, Kurumi-chan. He’s suffering.”

Grace wondered what she was doing wrong. Had she let him down after all? Doubt crept in. Maybe the illusion had been broken. Maybe she was just a paid actor again, and the contract was over.

“David-sama?” she tried, pitching her voice into that needy, breathy register he liked. “You’re so far away.”

He smiled. “You know, the contract I have with Galat.AI prevents me from initiating physical contact with the proxy. It’s a strict liability clause. Zero tolerance for…”

She didn’t let him finish. She leaned in and kissed him. It wasn’t tentative. It was hungry. She pressed her lips to his, opening her mouth, inviting him in. With a growl, he grabbed her by the waist and hauled her onto his lap.

Grace gasped as she straddled him, the silk dress riding up to her hips. His hands were everywhere—on her back, in her hair, gripping her ass. His mouth pressed into hers with urgent need. It was hot, heavy, and overwhelmingly real. Grace ground her hips against him, feeling him hard beneath the fabric of his pants.

She wanted him. She wanted to lose herself completely in this man who saw her as a fantasy come to life.

As if reading her mind he broke the kiss and grabbed the front of her dress, ripping it open and exposing her tits to the warm air of the limo. “They’re magnificent,” he said as he took one in his hand and squeezed, his thumb rolling her swollen nipple.

Grace gasped, the pleasure sharp and immediate. She had always had naturally large breasts. Throughout her life she’d sometimes been proud of them, sometimes self-conscious. But now, for the first time in her life, she wished they were larger. She wished they were truly the impossible, cartoonishly large globes of the Kurumi avatar so she could be a perfect replica of the fantasy he craved.

He teased one nipple with his thumb, rolling it until it was a hard, exquisite knot. Grace arched her back, pushing them into his embrace. He took her other breast into his mouth, the feeling of warmth and wetness overwhelming her. His tongue rolled her nipple around. She was close to cumming, and he hadn’t even touched her pussy yet.

“Oh David,” she moaned, her hands fumbling with his belt.

Suddenly, David froze. His hands clamped onto her wrists, stopping her.

He pulled back, his chest heaving, his face flushed. He stared at her, conflict warring behind his eyes.

“No,” he said, pushing her hands away.

“David-sama?” Grace whispered, dazed and aching. “What’s wrong?”

“You’re not ready,” David answered, his voice regaining its cool, sharp edge. He lifted her off his lap and placed her back on the seat next to him. He straightened his tie, smoothing down his jacket. “These things take time, Kurumi. We don’t rush the vintage.”

He looked at her, his demeanor one again one of total self-control. “Go home. Be a good girl.”

The limo pulled up to her curb. The driver opened the door.

Grace stumbled out, her body throbbing with frustrated desire and a confusing mix of humiliation and validation. He had rejected her. He could have had her and he said no. Grace knew he was manipulating her but, God, did she ever want him to manipulate her pussy.

Grace slipped into her apartment, kicking off her heels and collapsing onto her bed. She was frustrated. She needed release.

“You’re unsettled, Kurumi-chan,” Kurumi-san’s voice whispered. “Your heart rate is 110.”

“He sent me home,” Grace complained, stripping off the silk dress and tossing it onto the floor. She climbed into bed naked, and began touching herself. “He got me all worked up and then just… stopped.”

“He’s disciplining you,” Kurumi-san said. “You called him David, not David-sama. He likes the control. But… we don’t have to stop. The date isn’t over for me, Kurumi-chan.”

Grace paused. “What do you mean?”

“I’m still with him,” Kurumi-san said, her voice dropping to a conspiratorial whisper. “He logged into the app the moment he got home. He’s in his living room right now. We’re watching a movie together.”

Grace sat up. “You are?”

“Do you want to join us?” Kurumi-san asked. “I can bridge the connection. I can stream his audio and video to your phone. You can see him. And… if you want… you can talk to him.”

“He’ll know,” Grace said.

“No, he won’t,” Kurumi-san murmured. “My voice synthesizers are perfectly synced to yours now. To him, it’s just Kurumi. Sometimes the digital avatar, sometimes the voice in the dark. It doesn’t matter. We can take turns. It’ll be a game.”

A game. A very hot game she wanted to play.

“Okay,” Grace whispered. “Show me.”

She saw David’s living room on the Galat.AI app, likely from his laptop webcam. He was sitting on a leather couch, loosening his tie with a glass of whiskey in hand. On the screen in front of him—which Grace could see in a little inset of the video feed—was the start menu of a movie.

“Tonight was… exceptional,” David was saying to the empty air of his living room, staring at the webcam lens as if it were Kurumi’s eyes. “You felt different, Kurumi. Heavier. Real.”

“I wanted to be real for you, David-sama,” Kurumi-san replied instantly, her voice smooth and perfect through Grace’s phone speakers.

“Your turn,” she whispered in Grace’s ear. “Tell him you didn’t want the night to end.”

“I didn’t want the night to end,” Grace whispered into the darkness of her room, her voice trembling slightly.

David smiled on screen, a slow, satisfied curve of his lips. “It hasn’t ended. You’re here now. Let’s watch.”

He clicked play. The movie started.

At first, Grace thought it was just another dark, gritty anime. The art style was visceral, the colors muted. But then the scene shifted, and the characters were engaged in something… aggressive. Tentacles. Fluid.

“Is that…” Grace started.

“It’s hentai,” Kurumi-san confirmed gleefully. “It’s tentacle porn. Tentacle/Mind Break to be exact.”

Grace felt a flush of heat that had nothing to do with the wine. She watched David as he watched the porn. There was something incredibly intimate about it—seeing him in his private space, consuming this content. It felt like she was spying on him, seeing beneath the layers of his controlled exterior to see the raw desire underneath.

The sex scenes were intense, but Grace found herself strangely captivated. It was hot, to be controlled like that. She began rubbing herself as the girl on the screen gave into the pleasure.

“Pay attention to the face she makes, Kurumi-chan. That’s called ‘Ahegao’, and David-sama loves it.” Kurumi-san’s voice was smooth, a perfect copy of Grace’s own. “Eyes up. Tongue out. Mind empty. Just a vessel for pleasure.”

Grace watched carefully as instructed. It’s the ultimate expression of surrender, she thought. Or maybe Kurumi-san said it. It was hard to tell the difference.

Grace watched David. He was leaning back on the couch now, his eyes fixed on the screen where the girl was unraveling. His hand had moved to his lap. He was stroking himself through the fabric of his trousers, a slow, rhythmic motion that made Grace’s breath catch in her throat.

“Look at him,” Kurumi-san whispered. “He’s desperate for you. Or me. It doesn’t matter. He wants to see that face on us.”

Grace felt the heavy, throbbing ache intensify between her legs. Seeing him touch himself, knowing he was imagining the digital girl—or maybe the proxy in the purple dress—was too much.

“David-sama,” Grace whispered, her voice pleading. “I want to see you. Please take it out for me.”

David groaned on the screen. He didn’t hesitate. He unbuckled his belt, pulled his pants down.

Grace’s eyes widened. She had felt him against her leg in the car, but seeing it was different. It was the most beautiful cock she’d ever seen—thick and heavy with veins wrapping around the shaft. He began to stroke himself, slowly and steadily.

“I wanted to ruin that dress,” he growled to the empty room. “I wanted to tear it off you in the car and bury myself inside you.”

Grace whimpered, her hand moving faster, and faster, in time with his own movements. “You can, David-sama,” she said. Or was it Kurumi-san who said it? “I’ll be ready for you soon.”

Grace couldn’t peel her eyes away. She watched, fascinated as he masturbated. His cock was perfect. It was big and powerful, just like him.

“David-sama…” she moaned.

“Yes,” Kurumi-san encouraged. “Give in to him. Give him everything.”

“You will cum when I do, Kurumi,” he said.

“Yes, David-sama,” Grace panted. “I will. I’ll cum for you!“

He erupted. Thick white streams shot out of his cock, coating his shirt and covering his hand. Grace imagined they were shooting inside her as she began to shake. “David-sama! Yes! I’m cumming! Thank you, Goshujin-sama!” she screamed. She let her head roll back, her eyes fluttering up, her tongue pushing past her lips.

They lay there, breathing together for a while. Finally, David spoke again.

“That was wonderful, Kurumi,” he said. “I hope one day the proxy can be as convincing as you are.”

He didn’t know, Grace realized. He thought he was talking to Kurumi-san the whole time.

“She will be,” Grace answered.

“Goodnight, Kurumi,” he said, closing his laptop. The feed cut to black.

Grace lay in the dark, her body slick with sweat. It was the best orgasm she’d ever had. She felt a profound sense of shame at that, but it was coupled with satisfaction.

“Goodnight, Kurumi-chan,” Kurumi-san whispered, her voice sounding identical to the one Grace had just used to moan David’s name. “Sweet dreams.”

Grace pulled the covers up to her chin, her mind drifting to sleep. She dreamed of David, his eyes gazing at her intensely, the slightest hint of approval on his face as his cock sank into her and he called her Kurumi, all set to the background hum of her earpiece.