Chapter 5: The Almost

I stood there frozen for a moment, wondering where they’d disappeared to. Almost wondering if they had ever really been here. My heart pounded so hard I could feel it in my throat. Theye were definitely here. My mom and I had definitely seen each other. This was it. This was actually happening.

I started walking toward where they had been, weaving through naked bodies and ongoing sex scenes. A woman moaned nearby as a man bent her over a table. Two guys were double-penetrating someone in the hot tub. But no sign of Mom, Dad, or Linda.

“Ethan?”

I turned toward the familiar-sounding voice. A woman stood there—late twenties, wearing a short cocktail dress and a red mask. She had long brown hair, an athletic build, and curves in all the right places. I recognized enough of her for my brain to explode a bit.

“It’s me, you idiot,” she said with a laugh, pulling her mask up slightly.

Jessica. My older sister.

“Jess?” I stared at her. “What are you doing here?”

“What do you think, you dumbshit?” She laugher, gesturing around at the orgy. “Same thing as everyone else.”

Behind her, a tall guy appeared—broad-shouldered, dark hair, wearing slacks and a button-down with a mask. Tom, her husband. I’d only met him a couple times since they’d gotten married last year.

“Hey, Ethan,” Tom said easily, like we weren’t at a sex party. “Good to see you again.”

“Yeah, uh, you too.” I was still processing. Jessica knew about this? Jessica was part of this?

“We’re late,” Jessica explained. “Tom had to work. But we didn’t want to miss it entirely.” She looked me up and down, taking in my naked body and half-hard cock without any embarrassment. “Looks like you’ve been having fun.”

“I ... yeah. I guess.”

“You guess?” She laughed and stepped closer, her hand going to my chest. Her touch was casual but intimate. “Come on, little brother. You can’t tell me you’re not enjoying yourself.”

“It’s a lot to process,” I admitted.

“It is at first,” Tom agreed. He’d stripped off his shirt, revealing a fit torso. “But once you stop overthinking it, it’s amazing.”

Jessica’s hand slid down my stomach, getting dangerously close to my cock. “How long have you known? About all this?”

“Like a week,” I said. “Maybe a little more. Mia and Lily kind of ... introduced me.”

“Oh, those two are trouble,” Jessica said with a grin. Her fingers brushed against my cock, making it twitch. “Good trouble though. They know how to show someone a good time.”

“Jess,” I said, my voice strained.

“What?” She wrapped her hand around my shaft, stroking slowly. “We’re family. We’re supposed to be close.”

This was surreal. My older sister — who used to babysit me, who helped me with homework, who I’d looked up to growing up — was stroking my cock at an orgy.

“I’ve been part of this for about two years,” Jessica continued, her hand moving steadily. “Tom got recruited to the firm, and we got introduced to the lifestyle. It changed everything.”

“Changed it how?” I asked, trying to focus on the conversation despite what her hand was doing.

“Made us closer,” Tom said. He’d moved behind Jessica, his hands going to her hips. “Removed all the jealousy and possessiveness. We can enjoy other people and still love each other completely.”

“Plus the sex is incredible,” Jessica added. She released my cock and pulled her dress over her head in one smooth motion.

She was wearing nothing underneath. Her body was amazing—toned from regular gym sessions, with full C-cup breasts topped with pink nipples, a flat stomach, and curvy hips. Her pussy was neatly trimmed, just a small strip of hair above her slit.

“Damn, Jess,” I breathed.

“What? You’ve never thought about your sister naked?” She posed playfully, hands on her hips. “Because I’ve definitely thought about you. Especially since I heard you were home for summer.”

My cock was fully hard again now, and she noticed with a satisfied smile.

Tom had stripped down too. His body was solid—not as cut as Marcus but strong and capable. His cock was thick and long, maybe seven inches, already hard from watching his wife.

“Keisha!” Tom called out suddenly.

I turned to see Keisha nearby—she’d been talking with some other guests but perked up at her name. She was still naked and gorgeous, her body glistening with sweat and cum from earlier activities.

“Hey Tom,” she said, moving over to us. “Good to see you.”

“You too.” Tom pulled her into a kiss immediately, his hands groping her ass. “Want to play?”

“Always,” Keisha said with a grin.

Tom looked at me and Jessica. “You two catch up. I’m going to borrow Keisha for a bit.”

He led Keisha to a nearby lounge chair, and she immediately dropped to her knees in front of him. Her hands wrapped around his thick cock, and she started licking up the shaft while looking up at him.

“She’s so good at that,” Jessica said appreciatively, watching. “Tom loves her mouth.”

We stood there watching as Keisha took Tom’s cock into her mouth, sinking down until her lips met the base. Tom groaned and put his hand on her head, guiding her as she bobbed on his shaft.

“So,” Jessica said, her hand finding my cock again, “how are you handling all this? Really?”

“I mean I’m having a blast,” I said. “But it’s intense. I don’t feel like I’ve really been processing any of it. Amazing but also kind of overwhelming.”

“That sounds about right.” She stroked me slowly while we watched Tom and Keisha. “It took me a month or two to really adjust. But once you do, you’ll never want to go back to normal life.”

Keisha had moved to licking Tom’s balls now while stroking his shaft. Her technique was practiced and skilled. Tom’s eyes were closed, his head tilted back in pleasure.

“Get up here,” Tom said to Keisha.

She stood, and he turned her around, bending her over the lounge chair. Her ass was perfect—round and firm — and when Tom spread her cheeks, we could see her pussy was already wet and ready.

Tom pushed into her in one smooth thrust, and Keisha moaned loudly. He started fucking her immediately with deep, hard strokes, his hips slapping against her ass.

“Fuck yes,” Keisha gasped. “Your cock feels so good.”

Jessica’s hand was still on my cock, stroking faster now as we watched her husband fuck Keisha. “You like watching?” she asked me.

“Yeah,” I admitted.

“Me too.” Jessica pressed against my side, her naked body warm against mine. “I love watching Tom with other women. Gets me so wet.”

I could believe it. Her free hand was pulling my hand between her own legs, and for the first time I was feeling my sister’s pussy, the soft curls of her pubic hair, the furrowed valley beneath, the moist wetness of her entrance.

Tom was really pounding Keisha now, his thick cock slamming into her pussy. Keisha’s breasts swung beneath her with each thrust, and her moans were getting louder and more desperate.

“That’s it, babe,” Jessica called out to Tom. “Fuck her hard. Make her scream.”

Tom grabbed Keisha’s hips harder and increased his pace. The wet slapping sounds mixed with Keisha’s cries of pleasure.