Chapter 5: The Fourth Lesson: The First Time
The knock on Lucy's door was the hardest thing I'd done all week. My knuckles rapped against the wood, and I heard the soft shuffle of feet inside, then the click of the lock. The door swung open, and Lucy stood there in a loose white blouse and tight jeans, her hair down and shiny, her grin already in place.
"There he is," she said. "I was starting to think you'd chickened out."
"No," I said. "I'm here."
She reached out and pulled me inside by the arm. The room smelled like vanilla and something else, something floral, body wash maybe, that clung to the warm air. The fairy lights were on, the curtains drawn. The wooden chair sat in the corner with a fresh tissue box on the floor beside it.
Emily was already on the bed, sitting cross-legged in a light blue sweater, her hands folded in her lap. She looked up when I came in, and her eyes searched mine. I tried to smile. I think it came out more like a grimace.
"Hey," she said, soft.
"Hey, Em."
Lucy guided me to the chair. I sat down, the wood creaking under my weight. I set my hands on my knees and forced myself to breathe. For a long moment, the three of us were quiet.
"Okay," Lucy said, clapping her hands together. "Tonight's the night. I know you're both nervous, and that's okay. That's normal." She walked over to the bed and sat down beside Emily, taking her hand. "But this is important. I keep my promises, and I promised to get your body ready for your wedding night."
Emily nodded, her eyes dropping to her lap. "Where's Kaleb?"
"He'll be here soon. I texted him before you knocked." Lucy brushed a strand of hair from Emily's face. "But first, we need to get you ready. You got tense the second he walked in the room, didn't you, Caleb?"
I blinked. "I'm fine."
"Mmm." She gave me a knowing look, then turned back to Emily. "Here's what's going to happen. Kaleb's going to come in, and you're going to learn something new. Something important. But before he gets here, I want to make sure you're wet and ready for him. That's part of having good sex, sweetie. It starts with a warm-up."
Emily glanced at me, then back at Lucy. "You mean... here? Now?"
"Yes. Right now. You've been practicing for weeks. This is just the next step." Lucy leaned in and pressed a kiss to Emily's temple. "Lie back, sweetie. Let me take care of you."
Emily hesitated for a heartbeat. Then she lay back across the bed, her blonde hair spreading over the pillow case. Her eyes found mine, wide and soft, and she held my gaze as Lucy unbuttoned her jeans and pulled them off her slim hips.
"Lift up, love," Lucy murmured. Emily obeyed, and the jeans slid away, leaving her in a pair of pale pink panties. Lucy hooked her fingers in the waistband and pulled them down. Emily's bush came into view, dark and full, and her thighs trembled as Lucy parted them.
I swallowed hard. My hands tightened on my knees.
Lucy leaned in and pressed her lips to Emily's inner thigh. Emily let out a shaky breath. Then Lucy's mouth moved higher, dragging across her slit, and Emily gasped, her hips lifting off the bed.
"Oh," Emily breathed. "Oh, that's..."
"See?" Lucy's voice was muffled between Emily's legs. "You're already getting wet. Your body knows what it wants."
I watched the back of Lucy's head move between Emily's thighs. I watched Emily's hands find the sheets and fist them. I watched her mouth fall open, her cheeks flush pink, her eyes slide half shut. The sounds she made, soft and breathy, filled the room.
"Please," Emily whispered. "Lucy, please, more."
Lucy's tongue worked her in slow, steady strokes. She pushed two fingers inside Emily, and Emily's back arched, a raw moan tearing from her throat. I could see the wetness glistening on Lucy's fingers when she pulled them out, could see the slick shine of Emily's swollen flesh.
"God," Emily gasped. "I'm so wet. I'm so wet, Lucy, I can't believe how wet I am."
"That's perfect," Lucy said, lifting her head. Her lips were slick and red. "That's exactly where I want you. Ready and open. You're going to take him so well, sweetie."
A knock came at the door.
Emily's eyes snapped wide. Lucy smiled and rose, wiping her mouth with the back of her hand. She crossed to the door and opened it.
Kaleb stood in the frame. He was taller than I remembered from the video, broader through the shoulders, wearing a black tank top and loose jeans. A silver chain glinted at his throat. His skin was smooth and dark, and his smile was easy, laid back, like he did this every day, which I suppose he probably did.
"Hey," he said. "I'm not interrupting anything, am I?"
"Not at all," Lucy said. "Come on in."
He stepped inside, and his eyes found Emily on the bed. He took her in, the flushed cheeks, the parted thighs, the glistening wetness between them. His smile widened.
"Hey, Emily. Good to see you again."
"Hi," Emily whispered. She pulled her knees together, a sudden shyness washing over her. But Lucy moved to the bed and gently pushed them apart.
"None of that," Lucy said. "You've already met. And tonight, you're going to get much better acquainted."
I sat in my chair, frozen. The tissue box was beside me, and I hadn't touched it yet, but my cock was already straining against my jeans, thick and hot, a traitor's pulse.
"Okay," Lucy said. "Kaleb, let's get you ready too."
She crossed to him and put her hand on his chest, fingers splaying over the tank top. She pushed it up, and he lifted his arms, letting her peel it over his head. His torso was lean and defined, smooth dark skin over hard muscle. Emily stared at him, wide eyed, her lips parted.
"Are you ready?" Lucy asked him.
"Always," he said.
She dropped to her knees and unbuckled his jeans. They fell to the floor. His boxers followed, and his cock sprang free, thick and heavy, longer than the dildo, darker, veined. Emily's breath caught in her throat.
"Oh my God," she breathed.
"Don't worry," Lucy said, wrapping her fingers around the base of his shaft. "You're not taking that yet. First, I get him ready for you."
She leaned forward and took him in her mouth. Kaleb let out a low groan, his head tilting back, his hand finding the back of Lucy's skull. She worked her lips down his length, slow and deliberate, coating him with saliva. When she pulled back, his cock was slick and glistening.
"There," she said, reaching for a small foil square on the nightstand. "Now for the important part." She tore it open and rolled the condom down over his shaft, smooth and practiced. She gave him two firm strokes through the latex, and he groaned again.
"Good," she said. "Now, Emily. Come here. Kneel on the bed."
Emily looked at me. I gave her a small nod, my jaw tight. She rose to her knees, the sheets rumpled beneath her.
"Lie back," Lucy said gently. "Spread your legs for him."
Emily obeyed. She lay back, her knees falling open, her bush dark against her pale thighs, her slit glistening. Kaleb moved to the bed and climbed up between her legs. His weight dipped the mattress. He positioned himself at her entrance, the head of his cock pressing against her.
"Caleb," Emily whispered. Her eyes found mine. "Caleb, I'm scared."
"Breathe, Em," Lucy commanded. "Don’t worry about him!”
Kaleb looked down at her, his jaw set. "Just relax for me, Emily. I'll go slow. Tell me if you need me to stop."
She nodded, her chest heaving. He pressed forward. The head of his cock pushed against her opening, stretching her wide, and Emily gasped, a sharp, broken sound.
"Oh," she breathed. "Oh, God, he's so big, he's so much bigger than the toy..."
"Breathe through it," Lucy murmured. She was beside Emily now, stroking her hair. "Let him stretch you."
Kaleb pushed deeper. Emily's walls clenched around him, trying to push him out, but he kept going, slow and steady. I watched her cunt stretch around his girth, watched the condom gleam, watched every inch of his thick cock disappear inside my fiancée.
"Fuck," Emily sobbed. "Oh, fuck, it's too much, it's so deep, I can feel him so deep..."
"You can take it," Lucy said. "You're doing so well. Just keep breathing."
Kaleb bottomed out. His hips pressed flush against her, and he held still, letting her adjust. Emily's face was wet with tears, but her eyes were wide and dazed, her lips parted around ragged breaths.
"There," he said softly. "Feel that? Feel how full you are?"
Emily nodded, a hiccupping sound escaping her throat. "So full. I didn't know. I didn't know it could feel like this."
"Good," Lucy said. She moved her hand down between Emily's legs, finding her clit, swollen and slick, and began to rub it in slow circles. Emily's whole body shuddered.
"Oh," she gasped. "Oh, Lucy, that's, oh God, that's too much, that's so good, please don't stop..."
Kaleb began to move. Slow, deep, rhythmic thrusts, pulling his cock almost all the way out before pushing back in. Emily's moans filled the room, raw and unguarded.
"Yes," she keened. "Yes, yes, that's it, oh God, right there, please, right there, don't stop, please don't stop..."
I watched her body take him. I watched his hips drive into her, watched her breasts bounce with each thrust, watched Lucy's fingers work her clit in a steady rhythm. Emily's hands clawed at the sheets, her back arching, her mouth open in a continuous keen.
"I'm close," Emily sobbed. "I'm so close, oh God, I'm going to come, please, please, I need to come, please, I need to come so bad..."
"Come for him," Lucy said. "Come on his cock, sweetie. Feel it, let go, come."
The words broke her. Emily's body convulsed, her hips bucking up to meet Kaleb's thrusts, her cunt clamping down around him. She screamed, a raw, ragged sound that cut through me. I watched her come, watched her face contort, watched her body ripple and shake.
Kaleb drove into her through it. His rhythm stuttered, his jaw clenched. "Fuck," he gritted. "Fuck, she feels so good, Lucy. I'm going to come."
"Pull out," Lucy said. She was already there, her hand on his hip. "I want to taste you."
Kaleb pulled out of Emily with a wet sound. The condom was slick, and Lucy peeled it off in one smooth motion, tossing it aside. She wrapped her fingers around his bare shaft, still slick with lube and Emily's wetness, and took him in her mouth.
Kaleb's head fell back. His hips bucked, his hands fisting in Lucy's hair. "Fuck, yes," he groaned. "Just like that, Lucy, yes, I'm going to come, I'm coming..."
I watched his body tense. I watched Lucy's throat work as she swallowed him down, as his cock pulsed and spilled into her mouth. She pulled back with a soft, wet sound, her lips glossy, and swallowed again, a satisfied smile curving her mouth.
"Perfect," she said.
My hand was already on my cock. I hadn't even realized I'd freed it. It was slick and aching, and I fumbled for the tissue, my fingers clumsy. A single stroke, two, and I came, spurting hot and thick into the crumpled tissue, my breath ragged and raw.
Emily turned her head toward me. Her face was flushed and wet, her eyes hazy, but she was smiling. A soft, stunned smile.
"Caleb," she breathed. "Did you see? I did it. I really did it."
I wiped my hand on the tissue and set it aside. My chest ached, and my heart was hammering, and I couldn't tell if it was arousal or dread or something worse.
"Yes," I said. "I saw."
Kaleb lay back on the bed beside her, catching his breath. Lucy curled up on his other side, running her hand over his chest. The three of them looked like a painting, warm and intimate, in a way that shut me out. Emily was glowing.
"Thank you," she whispered to Kaleb. "That was... I didn't know it could be like that."
Kaleb smiled. "Anytime, Emily."
Lucy lifted her head, her eyes finding mine across the room. "And that's just the start, sweetie. There's so much more to learn."