Riley’s body was lighter than he thought it would be. He had more difficulty propping it up than he did actually lifting it. He raised her butt into the air and leaned her against the island. With his fingers he poked at her anus slightly as her cunt was still occupied with the wine bottle. The hole opened up only slightly. Even while she was asleep she did not relax it enough for him to push his fingers inside easily.
When he finally had it spread enough to fit a finger inside, she moaned in her sleep and shifted. The ring tightened around his finger like an elastic band. With his other hand, he worked the wine bottle out of her cunt and set it down so he could finger both of her holes at the same time. She made noises but still did not wake up.
After a while of enjoying the sight of his sister’s face contorting as he swirled his fingers inside her asshole and cunt at the same time, Adrian came up with an idea. He uncorked the bottle of wine and pressed the rim to her anus. It took a good shove to get it past the tight opening. A little bit of the wine spilled out and ran down her back when he inverted the bottle but most of it ended up pouring into her asshole. He watched with a gleeful smile as the dark liquid swirled into the neck like a whirlpool and vanished inside his sister.
Looking down at his own crotch he knew he was extremely turned on. Despite how much he disliked how his sister treated him, he could not deny she was attractive, especially with a whole wine bottle neck shoved inside her asshole. With some effort, he was able to hoist her into his arms and set her down on the island, lying on her side so the bottle in her butt would not fall out. He took his time spinning and pulling on it until it was right at the end of the neck. With one last tug, he pulled it out, unleashing a splatter of wine that quickly shrank to a trickle when her asshole was finally able to close, almost completely.
He poked at the hole a few times, causing her to moan in her sleep again. When she shifted, it opened enough for more wine to slip out. “I guess I’ll have to plug it with something,” he announced sarcastically.
After a few minutes, Riley finally awoke in a daze. She was confused about her elevated position. Her feet were propped on the edge of the island with her butt hanging off. Looking down she could see her cunt stretched around the neck of the now empty wine bottle. While most of it hand ended up on the floor, her dizziness proved she had absorbed at least some of it.
The final thing she noticed was a sore pressure in her butt. Her asshole felt like it was being stretched around something large. Looking behind her she saw her brother holding her in her precarious position on the island’s edge. He was on a stool so his height standing was about even with hers squatting. “What are you doing?” she asked drunkenly.
As if to iterate, Adrian pushed his hips against her butt, allowing his cock to slide inside her asshole and stretch it. “Raping you,” he admitted pompously.
“You don’t have the balls,” she laughed at him.
He wrapped his arms around her waist and leaned over her, pressing deeper into her asshole and also forcing her to squat on the bottle in her cunt more. She groaned as it stretched to accommodate more than the neck. Her eyes spun dizzily in her head and her breath was pushed out of her lungs as he compressed her body beneath him.
It was difficult for Riley to keep looking over her shoulder at Adrian so she went back to looking down at her cunt. While the neck of the bottle fit into her perfectly, the rest of it was stretching her and it looked oddly interesting to the drunk girl. Her cunt was wet, as if she was enjoying being violated by a thick bottle. The underside of her clit was sore and raw from being rubbed against the smooth glass.
She opened her mouth and let her tongue hang out as a stream of drool poured off of it. She had seen the many cocks of her boyfriends entering her but obviously they were not big enough to stretch the edges of her pussy and cause it to fold in on itself this way. She was more intrigued by how it looked than felt but she was still turned on. Her eyes glazed over as she spread her feet apart, taking the weight off of them and placing it solely on her cunt and the bottle. She had to grab it with both hands to keep it steady so she would not fall over.
Even from behind, Adrian could tell how messed up Riley was. Her expression as well as her actions; she was not resisting at all. She was entirely at his mercy. With a final shove, he buried himself deep in her asshole and began to cum. She moaned as she felt the warm goo splattering amongst the cold wine still filling her bowels. After six spurts, Adrian pulled out and stepped down off the stool to admire her round gapping asshole.
On more than one occasion, he had been able to hear his sister getting it one with a boyfriend in her room and had always tried to ignore it and found it gross. Now he was thinking back to the moans she used to make and hoping she looked just like this after getting fucked; naked sprayed out on her bed, unable to close her legs as cum leaked from her cunt or even her asshole as it refused to close.
With one hand still on her waist, he could feel her lower muscles moving in preparation to expel his cum and presumably the remainder of the wine inside her bowels. For some reason he did not want that and thinking fast grabbed the cork to the bottle and pushed it into her tiny asshole. Her anus went from gapping to puckered as it closed around his fingers the moment it felt the intrusion.
“What?” Riley gurgled in confusion as she fell forward on her face with her butt in the air. “Pull it out,” she whined. He slapped her ass a few times and even poked her anus but it was obvious he was not going to get his fingers in or the cork out until she relaxed more.
Instead, she rolled over onto her back and then lifted herself onto her knees, leaning slightly back so her cunt was thrust forward, almost at the edge of the island. She began to moan louder as she clenched her lower muscles around the fat bottle. She might have still been trying to expel her bowels but she was feeling it more in her cunt now.
Adrian grabbed her phone from her discarded shorts and snapped several pictures of his sexy athletic sister masturbating with a bottle in her cunt atop the kitchen island. He even caught a picture of the moment she threw her head back and howled in orgasm as liquid squirted out around the bottle. Before she lost control of her bladder, she grabbed the bottle and moved it so the lip was right in front of her peehole. Adrian obediently pulled the chopstick out so she could catch her urine in the bottle.
She bit her bottom lip to keep her voice down and stared forward at her brother with her eyes crossed as her whole body shook. When she realized he was taking pictures she let go of the bottle and folded down the middle two fingers on her hands like a punk rocker and posed with them beside her face. He loved how innocent her bit lip expression made her look; trying to maintain her composure while obviously enjoying her orgasm and showing off her enjoyment with her hand signs. She was a slutty contradiction, just like his feelings for her.