“Relax. Don’t be nervous. You’re doing great. I’m enjoying this. It feels… Tunny… this feels really, really right to me. Is that weird?”
Winston chuckled nervously. “It’s your hormones talking. You’d say that to the twelve year-old kid who delivers our newspaper if he was in my place right now.”
“Maybe,” she giggled again.
“Tunny?”
“Yeah?”
“I love you,” she said simply. She turned her head to softly kiss his nose. It was a sweet but absurdly chaste gesture given where his hand was.
“I love you too, sis.”
She closed her eyes and settled herself. He watched her lick her lips, her little pink tongue darting out to trace their outline. It made Winston wince. He watched quietly as his sister began to masturbate. His eyes darted between her flushed face and the outline of her hands moving beneath the concealing blanket.
At one point, on pure instinct, Winston began to move his fingers in and out a little without realizing it. Jessica’s eyes immediately flew open and she shook her head. “No,” she whispered hoarsely. He nodded and held still.
A minute later, his sister’s body began to move jerkily. Her breathing had become quick and shallow.
“Tunny, tell me to cum?” his sister whimpered.
“Go ahead and cum, Jess.”
“More. Tell me more.”
“Let it out honey. Let it out and be happy.”
“Dirtier.”
Winston blurted out what he was thinking. “Cum on my fingers, Jess. Let me feel your perfect little pussy cum all over my fingers.”
“My brother’s fingers,” she moaned. That did it. She groaned and spasmed. Her twitching walls clutched at the two fingers just inside her. Winston had to bite his own lip to keep quiet as he watched her vibrate through her release.
“How was that?” he asked as his sister finally relaxed.
“Wonderful,” his sister opened her eyes and looked at him. They were glazed and her pupils were huge and dark.
“I’m glad.” He gently eased his fingers from her. “Maybe now you can get some rest…”
Jessica frowned. “Not yet, I need more.”
“What?”
“What can I say? I’m not really a one-and-done kinda girl. I usually go at least twice. Do you have any condoms, Tunny?”
“Whoa, no I don’t. Do we really need to…”
“Shit. And, yes, I know what I need right now. How’s your willpower Tunny? Oh god, why am I even asking? You’re like a walking pyramid of willpower. That’s half our problem…” she muttered that last part to herself only semi-cryptically. “It doesn’t have to be a big deal, I’m just going to borrow the first inch and a half of your grade ‘A’ thing for a couple of minutes. Got it?”
“Let me see if I have this right, you’re going to use my real thing as a substitute for your fake thing which you need in order to properly fantasize about getting the real thing and have another orgasm so you can sleep.”
“Yep.”
“Right. Great. This makes perfect sense,” he said sarcastically.
“Don’t be mean. It’ll make it harder for me to relax.”
“You’re serious… why do you need me to do this?”
She turned to look at him. A lock of her dark hair covered one eye. Her ivory skin glowed in the light of the television. “Am I pretty?”
She had to know the question was rhetorical. “Yes,” he said softly.
“Do you love me?”
“Of course.”
“Did you lose at stolen kisses?”
“Yes.
“Do you want to help me?”
“Yes.”
“Then let’s stop talking about the ‘why’ and get down to the how.” She looked at him a little more seriously. “Besides, frankly, at least one part of you is really enjoying this. I felt your nice, big thingie poke me in the side a few times.”
She reached down and gently inserted her hand into the waistband of his pajama bottoms. He didn’t move to stop her as her fingers circled his erection. The unfamiliar and illicit contact between his sister’s hand and his cock made his head spin. His eyes slid tightly shut. So wrong. So very wrong. She stroked his end a few times, distributing his pre-cum, then grabbed the waistband and hauled it down over his hips. His erection sprang free.
The boldness of her move made Winston’s eyes fly open and fix on his sister’s face. She was staring at him intently, her mouth hanging open. She pursed her lips and exhaled as she drew his cock beneath her raised leg and towards her opening. He felt the heat radiating from her entrance before she placed him to her hot wet sex. They were just barely touching.
“Hunch into me a little?” she whispered.
He curled more tightly into her. Slowly, painstakingly, she rubbed him at her opening. She was warm, slick, and tight. So tight that he had to help by pressing into her steadily. It was the most intense feeling of his young life as he entered her. She gently but insistently stopped him before he was two inches inside her.
She was panting already. “Wow. That’s good. You’re ah… don’t take this the wrong way, but you’re nice and meaty in the way it counts. I feel stretched.”
“Jess!”
“Sorry, but it’s true. Okay, seriously, no cumming, Tunny. As bad as this is… as bad as what we’re doing is… if you come it would be really bad. Okay?”
“‘Kay,” he choked out. This was going to be even more difficult than he thought. He might as well never had sex before. The sensation of being inside of his sister made sex with other women pale by comparison.
He felt her hand moving above his shaft, playing at her clitoris again. Periodically, she traced a few fingers down around his girth to gather moisture from their leaking intersection to continue her masturbation.
For the first two minutes Winston forced himself to think about anything not sexual.
His sister interrupted his focus. “Tunny? Can you get on top of me? Please? It feels funny from this angle. It’s unbelievably good though. I’m going to cum really hard, I can tell already.”
He slipped out of her briefly then rose and slid between her legs. She carefully pulled him back into her, no further than before, and went back to masturbating. He looked down at his beautiful kid sister’s face, flushed with excitement. He fought the urge to lean down and press his lips to hers. He made the third and fourth minutes by exerting his considerable willpower.
Moving into the fifth minute, he starting formulating a way to tell his sister that he needed a break before…
Hallelujah! She rescued him with her second orgasm. Moaning a steady series of softly grunted “Ugh hugh ugh hugh, yeah,” she jerkily rocked forward and back in her enormous release. To his relief, her orgasmic rocking caused him to pop free from the warmth of her vagina.