Chapter 4: The Chat Room
The notification came through at nine thirty on a Tuesday night. I was at my desk, tracing a diagram for my engineering class, and my phone vibrated against the wood. Three times. Then six more. A new group chat, created by Lucy Serrano. She'd named it "Practice Makes Perfect."
Emily: "Lucy, is this necessary?"
Lucy: "Absolutely."
Lucy: "I've been thinking. You did so good with the dildo, sweetie. But plastic can't teach you everything."
Lucy: "A real man moves differently. Breathes differently. Comes differently."
Lucy: "You need to know how it feels before your wedding night. That's the whole point."
I stared at the screen. The words glowed in the dark of my dorm room, my fingers resting frozen on the keyboard. Across the hall, someone laughed. A door slammed. But I couldn't look away.
"Real man?" I typed, then deleted it. My thumb hovered. I typed it again and hit send.
Lucy: "Caleb, sweetie. You can't give her practice. You're saving yourself, the same as her. That's beautiful. But it means you need a stand-in."
Emily: "Lucy..."
Lucy: "I know a guy. Kaleb. He's a friend of mine. He's clean, he's careful, and he's very good at this kind of thing. I've seen him work."
My jaw tightened. Kaleb. She'd mentioned him once, in one of her meandering stories about her first year here, a name that moved through the apartment like gossip. I'd pictured him as some older student, a guy with a gym bag and a lazy grin.
Lucy: "He can come over Saturday. We'll make it a real lesson. Emily learns what it's like to feel a man, and Caleb, you watch. Same as always."
Emily: "I don't know. I said I'd stay a virgin until our wedding night. Caleb and I promised."
Lucy: "And you will be. Kaleb will penetrate you, yes, but that doesn't count. It's practice. Your covenant is with God, sweetie. You're the one who decides what that means, not the letter of it."
The words hung in the chat. I read them twice. Three times. My pulse hammered in my throat.
Then my thumb moved before my mind caught up.
"That's me," I typed. "You're talking about me, right, Lucy? You want me to be the one. To get Emily ready."
The chat went quiet. Three dots appeared. Then vanished. Then appeared again.
Lucy: "Oh, Caleb."
Lucy: "You misinterpreted, sweetie. I'm talking about Kaleb. You're the husband. He's the lesson. You'll watch, like always."
My face went hot. I could feel the blood in my ears, the sting of embarrassment crawling up my neck. I'd offered myself like a fool, and she'd corrected me with that soft little laugh in her voice that I could almost hear through the screen.
Emily: "Caleb. You don't have to do anything. I don't have to do any of this."
I typed back fast, before I could think. "No. It's fine. I want you to practice. I agreed to this, and I trust Lucy. If she says Kaleb is safe, I believe her."
Emily: "But you'd be here, right? You'd be watching?"
Lucy: "Of course he'll be there. Same as every Saturday. Caleb sits in the chair, and you learn. It's like we always do."
I stared at the message. The word "practice" burned in my chest like a coal. I told myself this was fine. This was exactly what we'd agreed to. Emily learning her body, so our wedding night would be perfect.
Emily: "Okay. If Caleb's okay with it, I'll do it."
The message sent. My stomach knotted in a way I couldn't name.
Then Lucy sent a string of emoji: a purple devil, a kissing face, a flexed arm. "Saturday. Seven o'clock. I'm so proud of you both."
I turned the phone over and stared at the ceiling. The weight of what I'd agreed to pressed down on me, and I couldn't tell if it was cold fear or a heat I didn't want to name.
Saturday came with a price I hadn't expected. My engineering professor had announced the project due Monday, a structural load analysis I'd neglected all week. I'd been so tangled up in Emily, in the Saturdays, in the slow drip of her unraveling under Lucy's hands, that I'd let the assignment slide.
I called Emily that morning. "I can't come tonight."
The silence on the other end stretched. "Caleb. You have to be there. I can't do this without you."
"I know. I'm sorry. But if I don't turn this in, I fail the class." I could hear the desperation in my own voice. "It's one Saturday. We'll pick it up next week."
"Then we should postpone. Tell Lucy we're not coming."
I could picture her expression, the worried pinch between her brows. The part of me that loved her, the part that wanted to wrap her in my arms and protect her from the world, screamed at me to say yes, we'd postpone.
But the other part, the one that had been slowly growing in the dark of Lucy's apartment, whispered that Emily needed this. That if she got comfortable, she'd draw back. That this was necessary.
"Go," I said. "Lucy will take care of you. I'll be there next Saturday, I promise."
The silence again. Then, soft: "Okay. I'll go."
"Send me updates? I want to know everything."
"Okay, Caleb."
She hung up. I put the phone down and stared at my textbook. The diagram blurred.
At seven oh seven, my phone vibrated.
A text from Lucy. A video.
I clicked it.
The frame was dim, lit by fairy lights. Emily sat on Lucy's bed, naked, her legs pulled up under her. Her chest heaved. Beside her, Lucy knelt, wearing her black robe, open in the front. Beyond them, on the edge of the bed, a man sat with his back to the camera.
Kaleb. He was lean, shirtless, dark-haired. I could see the curve of his shoulder, the flex of his spine as he shifted. My heart slammed against my ribs.
"This is Kaleb," Lucy said, her voice a warm purr through the speaker. "He's going to help you practice, sweetie. Just like I told you. Say hi."
Emily's voice came tiny through the phone. "Hi."
Kaleb turned. I caught a flash of a face, young, handsome, a smile that looked easy and kind. "Hey, Emily. Lucy's told me a lot about you. Don't worry. We'll take it slow."
Lucy: "Caleb, I thought you'd want to see. Since you couldn't be here."
I gripped the phone so hard the screen cracked under my thumb. The video kept playing.
"Now," Lucy said, "before anything happens, there's one thing I want to teach you first."
"What is it?" Emily asked.
"Your mouth. There are things you'll need to know on your wedding night that aren't just about what happens between your legs." Lucy gestured to Kaleb. "Show her, sweetie."
Kaleb stood. He unbuckled his jeans. They fell to the floor. He stepped out of them, and his boxers came next, and I watched Emily's eyes go wide as his cock sprang free, thick and hard, longer and heavier than the dildo she'd taken last week.
"Oh my God," Emily breathed. "That's..."
"He's a little bigger than the toy," Lucy said. "But you're ready for him. You've been practicing."
"I can't," Emily said. "I can't put that in my mouth."
"Sure you can. It's just like licking a popsicle, only warmer. Your future husband is going to want this, sweetie. You need to learn."
I watched Emily crawl forward on her hands and knees. I watched her reach up, hesitant, her fingers brushing the base of Kaleb's shaft. He let out a low breath. She leaned in and pressed a kiss to the head, tentative, like a question.
"Good girl," Lucy said. "Now open your mouth. Let him guide you."
Emily obeyed. Her lips parted, and I watched Kaleb's cock disappear between them, inch by inch, watched her cheeks hollow as she sucked. The sound, wet and rhythmic, came through the speaker. Kaleb's head fell back. Lucy stroked Emily's hair.
I was already hard. My hand moved, unbuckling my jeans, pulling myself free. I was so worked up I came before I could even get a grip, spilling hot across my fist, my breath ragged in the empty dorm room.
But I couldn't stop watching.
The video went on. I watched Emily learn to take him deeper. I watched her gag, her eyes watering, and then pull back and try again. Lucy coached her through it, gentle and patient, the way she'd coached her through the bullet and the dildo.
"Slower, sweetie. Breathe through your nose. Use your tongue. That's it. You're so good at this."
Emily's cheeks went hollow. Her head moved in a rhythm. Kaleb's hand cupped the back of her skull, not forcing, just steadying. The video ended.
"Please," I sent.
"She can't talk," it said. "He's coming in her mouth."
I stared at the words. Then another message, a new video. This one showed Emily pulling back, her lips slick, a white strand of something connecting her mouth to the head of his cock. She swallowed, and her eyes were glassy and pink, but she was smiling.
"Caleb," Emily's voice came thick through the speaker. "I did it. I'm learning so much."
I sat in the dark, my hand sticky and spent, and I watched my fiancée smile at another man. I typed back, my fingers clumsy. "I'm so proud of you."
Lucy's message came a moment later: "Saturdays are just the start, sweetie. There's so much more to learn."