Chapter 7: The Fifth Lesson: The Back Door
The days blurred. I went to class, ate meals I didn't taste, answered texts with smiling emojis. Emily called me every night, her voice bright with wedding plans, venue options, flower arrangements. She'd found a caterer. She'd picked out favors. She talked about our first dance with such warmth, and I listened, made the right noises, and prayed she wouldn't ask what I was thinking.
On Thursday, Lucy texted the group chat. "Saturday. 7pm. I have something special planned."
My thumb hovered over the keyboard. I typed "What kind of special?" and deleted it. Typed "I'll be there" and hit send before I could second-guess myself.
Emily replied with a string of hearts. "I can't wait."
Saturday came cold and gray. I left my dorm at six thirty, my stomach in knots, my hands clammy. The walk to Lucy's building felt shorter than usual. When I reached the door, I paused, one hand raised, and my breath came shallow.
I knocked.
The door swung open. Lucy stood there in a black silk camisole and shorts, her hair loose, a knowing smile on her lips. "There he is. Come in, we've been waiting."
We've.
I stepped inside. The apartment was warm, vanilla-scented, the fairy lights casting soft golden pools. My chair sat in its usual place, tissue box waiting. But the bed caught my eye first.
Kaleb was sprawled on it, shirtless, bare-chested, propped on one elbow. His jeans were unbuttoned, riding low on his hips. The silver chain glinted at his throat. He grinned when he saw me.
"Hey, man. How's it going?"
"Fine," I said. My voice came out rougher than I meant.
Emily emerged from the bathroom in her thin white nightgown, her hair loose and soft, her face bright. She crossed to me and pressed a kiss to my cheek. "I'm so glad you're here."
"Hey, Em."
Lucy closed the door behind me and clapped her hands. "Okay, everybody. Tonight's lesson is about something a lot of couples forget. Something you might want on your wedding night, especially if you're in a season where the usual is off the table."
I felt cold. "What do you mean?"
Lucy smiled, slow and deliberate. "Anal, Caleb. Some women love it, and some men really want it. Emily should know what it feels like before she's married. That way, if you ever want to be with her that way, she'll already be comfortable."
Emily's eyes went wide. Her fingers plucked at the hem of her nightgown. "Lucy, I don't know..."
"Trust me, sweetie. It's just another way to be close. And I promise, it can feel amazing if you do it right." Lucy moved to her, took her hand, guided her to the bed. "Lie back for me."
Emily looked at me. Her eyes were searching, seeking permission. The words came out of me before I could think.
"It's okay, Em. I want you to learn."
Her face relaxed. She lay back on the pillows, her knees together, her hands folded over her stomach. Lucy knelt beside her and lifted the hem of the nightgown, sliding it up over her hips.
"First, we need to get you ready," Lucy murmured. "Warm and open. You're going to be so tight back here, sweetie. We need to make sure this is pleasure, not pain."
She pushed the nightgown up over Emily's breasts and off her head. Emily lay bare, her pale skin glowing in the fairy light, her bush dark and full. Lucy spread her knees, slow and gentle.
"Let me taste you first."
Lucy pressed her mouth to Emily's cunt. Emily gasped, her hips lifting. Lucy worked her tongue in long, slow strokes, building a steady rhythm. Emily's hands found the sheets, fisting them.
"Oh," Emily breathed. "Oh, Lucy, that's, that's so good..."
"Mm." Lucy nodded against her thighs. "Good girl. Let me get you dripping."
She pushed two fingers inside Emily's cunt, curling them upward, and Emily cried out, her back arching. "Yes, right there, please, please..."
Lucy's tongue circled Emily's clit while her fingers pumped. Emily's moans grew louder, higher, her hips grinding against Lucy's mouth. Her skin flushed pink, sweat beading at her temples.
"I'm close," Emily gasped. "I'm so close, please don't stop, please..."
"Not yet," Lucy said, pulling back. Emily whimpered at the loss. "I want you on the edge. I want you desperate. That's going to make what's next so much better."
She rose, wiping her mouth. "Kaleb, come here. Lie back against the headboard."
Kaleb shifted, moving to the head of the bed, his back against the pillows. Emily watched him, her eyes hazy, her thighs trembling. Lucy touched Emily's shoulder.
"You're going to finish getting him ready, sweetie. Mouth first. You've practiced before, so show me what you've learned."
Emily hesitated, then crawled across the mattress toward him. Kaleb's jeans hung open, his boxers tented. He reached down and pushed them aside, and his cock sprang free, thick and dark, already half-hard.
Emily's breath hitched. She stared at it, her lips parted. Then she leaned forward, her small hand wrapping around the base, and took the head into her mouth.
"Oh, fuck," Kaleb breathed. His head fell back against the pillows. "Yeah, just like that, Emily."
Her mouth slid lower, taking him deeper. He grew in her mouth, filling her, stretching her lips. She bobbed slowly, her head moving in an unbroken rhythm, her eyes closing. Wet sounds filled the room, soft and obscene.
"Good girl," Lucy murmured. She was beside Emily now, stroking her hair. "You're so good at that. He's so hard for you."
"Yes," Kaleb groaned. "She's got a mouth like a dream. Fuck, Lucy, she's better every time."
“Every time” Caleb thought. “I thought she only did it once?”
Emily sped up, her head moving faster. Her cheeks hollowed, her hand pumping the base in a matching rhythm. Kaleb's hips began to move, shallow thrusts into her mouth.
"That's enough," Lucy said gently. Emily pulled off with a wet pop, a string of saliva connecting her lips to the head of his cock. She panted, her face flushed, her eyes glassy. Kaleb's cock stood fully erect, slick and glistening.
"My turn to prep you," Lucy said. She reached for a bottle on the nightstand, clear liquid in a flip-top cap. "This is lube, sweetie. More than you think you need, and then a little more."
She poured a generous amount into her palm, then touched Emily's backside. Emily flinched at the cold.
"It's cold," she whispered.
"It'll warm up. Just breathe." Lucy's slick fingers pressed against Emily's entrance, circling it. Then one finger pressed inside, slow and gentle.
Emily gasped. "Oh. Oh, that's strange..."
"Just breathe through it," Lucy said. "Your body needs to learn to take it. This is practice, remember."
She worked her finger in and out, slow and steady, coated in lube. Emily whimpered, her hands twisting the sheets. Lucy added a second finger, and Emily's whole body tensed.
"Shh, sweetie. Relax. You're doing so well."
"Please," Emily breathed. "It feels so full, I don't know if I can..."
"Just breathe. Let your body open up."
Lucy's fingers worked her, stretching her with practiced patience. Emily's breathing grew ragged. Her eyes were squeezed shut, her face a mix of fear and something else, something I couldn't name.
"Okay," Lucy said, pulling her fingers out. "I think you're ready."
She turned to Kaleb. "Slow. She's new to this. Gently, and stop if she says stop."
Kaleb nodded, moving into position behind Emily. She was on all fours now, her forehead resting on the pillows, her hips raised. Trembling. Her cunt was slick and wet, dripping. Her asshole glistened with lube.
I gripped the arms of my chair. My cock was painfully hard against my jeans, a sick heat in my belly.
Kaleb positioned himself at her entrance. The head of his cock pressed against her. Emily cried out softly.
"Easy," Lucy said. "Just the tip first."
He pushed. Emily's body tensed. A sharp gasp tore from her throat.
"Too much," she whimpered. "It's too much."
"Just the head," Lucy said. "Breathe, sweetie. Let him in."
Kaleb held still, giving her time to adjust. Slowly, the thick ring of muscle gave way, and the head popped past her rim.
"Fuck," Emily sobbed. "Oh, fuck, it's so big, it's so full..."
"Good girl," Lucy murmured. "You're doing so well. Tell him when it's okay to move."
Emily's breath shuddered. A long moment passed. Then, softly, she nodded. "Okay. You can move."
Kaleb pushed forward, another inch. Emily cried out, her hands clawing at the pillows. But she didn't tell him to stop. He drove deeper, filling her slowly, till his hips pressed flush against her ass.
"Oh God," Emily breathed. "He's so deep. It hurts, but it's, it's so much..."
"That's good," Lucy said. "That's exactly how it should feel. He's going to move now."
Kaleb pulled back, then pushed in again. Slow and deep. Emily moaned, a raw, broken sound. He built a rhythm, unhurried, his hips sliding against her, his balls swinging.
"Harder," Emily gasped. "Please, it feels, it feels so good, I need it harder..."
Kaleb obeyed. His thrusts grew deeper, faster. The slap of his hips against her ass filled the room, wet and rhythmic. Emily's cries grew louder, higher.
"Yes," she screamed. "Yes, yes, right there, oh God, oh God, I'm going to come, I'm going to come..."
"Come for him," Lucy said. Her hand snaked between Emily's legs, finding her clit. "Come on his cock, sweetie. Feel it."
Emily shattered. Her body convulsed, her ass clamping down around him so hard Kaleb grunted. She screamed, raw and ragged, her face buried in the pillows.
"Fuck," Kaleb gritted. "She's so tight back here. I'm going to come."
"Inside her," Lucy commanded. "I want her to know what it feels like."
Kaleb drove into her, harder, faster. His rhythm stuttered. Then he froze, his body tense, his jaw clamped. A deep groan tore from his throat, and Emily cried out as heat flooded her bowels.
"Oh," she breathed. "Oh God, it's so warm, I can feel it, I can feel him coming inside me..."
Kaleb collapsed against her back, his breath ragged. He pulled out slowly, with a wet sound, and fell onto the mattress beside her. Emily lay there, trembling, her ass pink and slick with lube.
"Beautiful," Lucy murmured. She leaned in and kissed Emily's shoulder. "You took him so well, sweetie. And that's what your husband can do during your cycle, if you ever want to be close that way. Just remember this."
My hand was already on my cock. I hadn't even realized I'd pulled it out. I fumbled for the tissue, my fingers clumsy. Two strokes, and I was coming, spurting hot and thick into the crumpled tissue, a choked breath tearing from my chest.
Emily turned her head toward me. Her face was wet with tears, her eyes hazy. But she was smiling. A stunned, overwhelmed smile.
"Caleb," she breathed. "Did you see? I did it. I really did it."
Something cracked inside me, deep and silent. I wiped my hand on the tissue and set it aside. My heart pounded slow and heavy.
"Yes," I said. "I saw."