Winston’s attentions were split between fighting off a vicious case of room-spins and trying not to get a complete hard-on while watching a scantily clad Britt Ekland work her on-screen magic and having his sister’s bare ass pressed against him. “Generally or specifically?” he replied absently.
“Specifically. Like right now. I don’t suppose you got me a new toy while you were out?”
“I asked you if you needed anything this morning and you said no.”
“I didn’t think of it. I don’t think of vibrators while I’m having my morning oatmeal.”
“I’m not going through what you put me through last night,” he said preemptively.
There was a long pause.
“Actually, I don’t think you have to. You know what we did after I got off?”
“Yeah,” he’d never forget grinding along the smooth tight crease of his sister’s perfect ass.
“I really liked it. I think I could come just doing that. If I hadn’t had two humongous orgasms just before, I probably would have gotten off again.” She wiggled her ass back into him until his hardening, pajama-covered cock was caught between her firm little buns.
“Sis?” he slurred the question.
“Please? You can leave your clothes on this time if you want, I promise. The rum and the romantic movies and snuggling with you for the last couple of hours has me pretty wound up. Just hold still. If you feel like it, you can help by humping back against me.”
“Fine.”
She ground back against him for a few minutes and, against what was left of his judgment, he found himself pressing back into her. They humped for several minutes. He was soon panting into the back of her neck.
She turned her head to ask him something and in his inebriated state he misunderstood her intention. He kissed her – a long, hard searching kiss that made her gasp into his mouth. It was their first lovers’ kiss. She parted her lips in invitation and he slid his tongue into her mouth, playing it across her teeth. She teased him back with her own.
He broke their kiss. “I’m getting raw,” he whispered, “need to take my pants off okay?”
“Do it,” she said hoarsely. Actually she’d been about to ask him if he minded taking them off when he kissed her.
He shimmied free of his pajama bottoms and spooned back into his sister. She wriggled back against him until he was trapped again between her ass cheeks. The flesh-on-flesh contact was intoxicating in a way rum could never be. They resumed humping. Her crease was soon slick with his pre-cum. By the way her elbow was moving beneath the blanket, he knew his sister was rubbing her clitoris.
Jess said something so softly over her shoulder that he had to ask her to repeat it.
“I said, ‘do you know where you are right there?’ ”
He had only been following the roughened texture on instinct. He realized now that he had been twisting against her rosebud during their humping. “Oh, wow, sorry.”
“No, it’s okay, it actually feels kinda good. I just didn’t want you to get grossed out.”
The late hour and the rum made him honest: “Jess, there is absolutely no part of you that I find gross.”
“That was sweet, Tunny. Okay, more humping please. I’m most of the way there.”
They resumed their grinding. Soon, the tip of his erection caught on the dent of her sphincter and he was lined up perfectly. They both froze.
It was Jess who broke the silence. “Push a little, Tunny?”
He gently hunched towards her, barely able to breath, barely able to believe what she was asking him to do. His cock was pressed firmly against her backdoor. Even through the rum haze he knew this was wrong on multiple levels. It just helped him not care enough to stop.
“Little more?” she whimpered.
He felt her rear entrance begin to give way. Felt the barrier spread into a tiny circle. Felt that tiny circle yield to their combined pressure as she helped by gently wriggling backwards into him.
His sister grunted a soft “ugh” just as the head of his cock slowly slipped into her ass. Her clit hand moved in a frenzy between her legs. The penetration was enough to bring her orgasm on in a rush. She went rigid, her hand continuing to circle her clit. She curled into a ball, heaving a delighted “God yes!” as her orgasm rolled over her. Her curling motion pulled her away from him and he slid free of her ass.
Winston waited patiently as she caught her breath. She turned her head and she kissed him.
“That was sooooo good. Thank you.” She looked at him, her eyes glinting happily. She saw his distress, it was written across his face. “Steven evens again?” she asked, kissing him, her tongue tracing along his lip wantonly.
When he finally nodded, she wriggled her ass back against him and he resumed grinding up between her asscheeks.
Inevitably, his tip was rubbing at the loosened, rougher flesh of her rosebud again.
He angled into it instinctively to maximize the contact and he caught himself at her entrance.
“You want to go inside again, honey?” she asked, her hand drifting to his hip.
“Yessss,” he hissed softly.
She reached back and took his warm hard length in her hand. She centered him on her ass.
“Push a little again, Tunny.”
He entered her more easily this time and she released her hold on his shaft.
“Can I have more this time?” she asked over her shoulder. “I… I kind of like this,” she whispered.
He slid almost three inches of his eight inch length into her. Her rectum was furnace-hot and absurdly tight. It was also slicker than he expected, but then again he didn’t have much experience in this department.
“Does this feel good big bro?” she asked, her voice was strained.
The question had to be rhetorical, he realized even in his drunken state. “Uh huh.”
“Want to try more?” she offered quietly.
“God, yes.”
She pressed back against him as he pushed into her. Inch by inch, he slowly slid his cock another three inches into her back passage.
“Oh my god you feel huge,” Jess whimpered and paused, “Tunny, honey, I want… I want all of it… all of you inside me, okay? Hold still.”