Author's Note: While this story and its various chapters are primarily incest themed, it will often contain things such as excessive cum, anal play/pegging, and whatever else amuses me at the time. Reader discretion is advised.
****
Jaime woke up to the bizarre sensation of someone licking his butthole. He was lying on his back and his legs had been pushed up toward his chest to make room. He looked down to find his sister Emily with her head partly hidden behind his hard cock. She was busily tonguing away at him.
"What are you doing?" he asked.
Emily stopped licking and looked up. "Morning," she said cheerfully.
"Good morning to you too. But seriously, what?"
Emily tilted her head. "You don't like it?"
Jaime shrugged. "I dunno. It's weird, but... kinda nice? It's like... well, it's not like anything, really."
His sister seemed to parse his feedback, then gave a curt nod and started licking again. His butthole had never been more covered in saliva in his life.
"Em?"
"Oh fine. I'm getting you prepped."
"Prepped for what, dare I ask?"
Emily smiled and finally let go of his legs. He let them drop back down to the bed. She pulled out the nondescript bag Lilith had given him for his birthday. His eyes widened as he remembered what the bag contained.
"I found this just lying around," Emily said, pulling a brand new butt plug from the bag. "I thought that now might be a good time to try it out."
"It's not even mine," Jaime said quickly.
"Of course it is. It was in your room." Emily frowned. "Are you embarrassed about having it? You don't need to be, you know."
"Lil gave it to me. I didn't even want it."
"Oooh, it was a present from Lil. That actually explains a lot."
"Right, so we don't have to try it out."
"Au contraire. If there's one thing Lilith's an expert on, it's weird sex stuff. She wouldn't have given you this if you weren't going to like it." Emily pulled the bottle of lube out of the bag and tore the plastic wrapper off the top. "This might be easier if you roll over."
"Em...."
Jaime wanted to protest, but Emily wouldn't have any of it. She was far too intrigued to let the idea drop. She whipped out her sad puppy eyes and pouty bottom lip. Jaime never stood a chance.
"Fine," he said.
He rolled onto his stomach and, at his sister's urging, pulled his knees under him to stick his ass upward. She poured some lube in his ass crack, then massaged it in with her fingers. Again the feelings that Jaime experienced were new and unfamiliar, but not unpleasant.
"How's that?" Emily asked.
"It's... ok," Jaime admitted grudgingly.
"And how about this?"
Emily poked a finger gently into his butthole. She only had small fingers, so it wasn't much of an intruder at all. It didn't hurt the way Jaime had feared it might. It felt kind of interesting, actually. In some ways the sensation was more anticipatory than physical.
"That's fine," he said.
Emily nodded to herself and carefully added a second finger. She stuck them in deep and wiggled them around. Now Jaime could really feel something happening. He was mildly distressed to find that he actually kind of liked it. It was a new and decidedly sexual touch on a previously unexplored part of his body. Mostly it made him very confused.
"Right, time for mr. plug," Emily declared.
Jaime felt a disturbing sense of longing when her fingers withdrew. He was just starting to get used to the idea of being anally penetrated by his sister.
"Wait. Em, this doesn't make me gay, does it?"
He couldn't see the look of sheer incredulity she gave him.
"Well," she said in the tone of voice one might use with a particularly slow child, "I'm a girl, and we've spent the past two days with your penis inside me at every conceivable opportunity. In fact, you can't seem to stay soft when I'm around. And you seem to react to other girls being sexy too. But no, you're right. Maybe having a girl play with your butt makes you a guy who enjoys sex with other guys."
"It sounds completely fucking retarded when you put it that way," Jaime said sheepishly.
"'Cause it is."
Emily licked the brand new butt plug for luck. She pressed it against her brother's asshole, then shoved it in without giving him any more chances to protest.
Jaime experienced a brief flash of pain as the widest part of the toy entered him, but it was over before it registered. He was left with the sense that... something was there, where it shouldn't be. It didn't hurt, and didn't feel gross, but also didn't feel like any particularly sexual.
"That's it?" he asked.
"That's it. Do you like it?"
"I don't not like it. But it's not really doing anything for me."
"Hmm...."
Emily quite enjoyed playing with her brother's butt. He looked so sexy and vulnerable with his face against the mattress and his ass sticking up at her. She wanted him to enjoy it too, but so far the results had been mediocre. She reached out and touched the base of the plug, wiggling it experimentally.
"Ooh," said Jaime before Emily could ask how it felt.
"You like that?"
"Yeah, that's nice. Weird, but nice."
So Emily wiggled the toy, and pulled it slightly out, and generally just played with it. Jaime moaned and squirmed beneath her. She had him now.
"We'll make a butt slut out of you yet," Emily said.
"Hey! Don't make me sound like a weirdo."
"Perish the thought."
Emily wrapped one hand around her brother's hard cock while continuing to finger his toy with the other. It might have been an illusion, but she could have sworn she felt his cock react to the movements of the plug in his ass.
