Becky creeped around the bushes of her house, trying to be stay quiet and out of sight of any nosy neighbors. Her parents were likely already asleep, but it never hurt to be careful. Her friend, Harper, had had a big party at her house, and Becky had snuck out to go to it. Not only would her parents not approve of her going to a party that started at 10:00 pm and ended at two in the morning, but she had also been grounded for getting caught smoking weed by her mother.

It was a big risk, but she was not going to let herself miss such a kick-ass party. Not only did Harper hold the best parties on account of her parents always traveling, but on that particular occasion, she had got a number of senior boys to attend the party. She was in the process of hitting up a really cute senior a year older than her and everything had been going well, up until the point that she realized that one of the seniors who had been invited to the party was her eighteen-year old stepbrother, Phil, who was a year older than she was.

Several months back, her stepbrother had blackmailed her into having sex with him when he caught her smoking weed in her room. Harper caught them just as they were getting started, and she ended up joining in and they had a threesome, the first of several. Becky and Phil had been having sex routinely for several months after that, but she eventually got bored of her brother and ended their sexual relationship. This pissed him off, naturally, and she realized how much she missed annoying her older stepbrother like she did before they started fucking.

When she saw Phil at the party, Becky left, sadly leaving behind the hunk she had been flirting with for nearly half an hour. Her house was on the same street as Harper’s, so she so was able to quickly get back home. Weighing her options on how to get in, she realized that she had returned home sooner than she had planned, and as a result her parents might not have been as fast as sleep as she would have liked for her to try one of the house’s squeaky doors. Instead, she decided to open and crawl through the living room window, which she knew had a busted lock that her stepfather still hadn’t fixed.

Walking softly, Becky made her way over to the living room window and started to pull it up. It took a bit of tugging, but eventually the window gave and she was able to raise it all the way open without making too much noise. The window was a bit high, so putting one foot through it and swinging herself into the living room didn’t seem possible, so she put her arms through the window and tried to pull herself in. She was almost into the window to her waist when she suddenly felt like she was stuck on something. As it turned out, her leather jacket had apparently been caught on something in the window frame, and she couldn’t finish getting inside the house, or backing out of it.

At first, Becky tried to to take the jacket off, but it was too tight and the task of removing it was made harder by the fact that half of her body was stuck inside of the house, and the other half outside. She kept trying to pull herself out of the window, but the leather jacket remained stuck. Just as she was about to try to free herself again, she heard leaves crunch to her right, the direction of the front driveway. She turned her head to look at who was coming towards her: it was her brother, Phil, already sporting an amused smile and trying to fight back laughter.

“Well lookie what we have here,” he said as he walked up to his sister and stood behind her. “It looks like you’ve gotten yourself into a bit of a jam, sis.”

“Phil, I need your help,” Becky said as she strained her neck to look behind her at her stepbrother, fearful that her parents might hear them. “My jacket is stuck on something and the material to too strong for me to rip. I need your help.”

“Well, I don’t know, sis,” he said while emphasizing their familial relationship, something she really hated, despite the fact that they were only step-siblings. “What do I get for saving you? I mean, I think it would be more beneficial for me to let you get in trouble to take the heat off of me after that thing involving mom’s yoga friend...”

Becky grunted in annoyance.

“Look, just get me out of here, and we’ll talk about that later. If mom and dad catch me and find out I went to Harper’s party, I’ll be grounded for the next three months, at least.”

“Fine, I’ll do my best,” Phil said and took hold of his sister’s hips. He tried pulling first, and when that didn’t work, he tried pushing her forward.

In an attempt to get a better grip, Phil looked for something to grip onto as he pushed. Settling on her pants, he struggled to grip onto the slick, shiny leather of Becky's pants. After finally getting a grip on her pants, he moved his pelvis to her backside in order to leverage his body against his stepsister’s. Becky became aware that her stepbrother’s pulling on her pant’s caused the thin, imitation leather to ride up her crotch and form a camel-toe over her pussy. God, why did I decide to wear a G-string tonight?

“Oww,” she cried as Phil's body pushed against hers.

She felt her brother let go of her pants, causing Becky to initially be thankful that her pants were no longer painfully riding up her crotch. The relief was short lived though, as Phil’s hands found something else to grip: Becky's ass. She gasped, at first because of her brother’s touch, then because Phil started to straddle her, presumably to give her another push.

However, instead of pushing against her to get her through the window, he just continued straddling her.
Becky felt Phil’s hands start to reach around her waist and it seemed to her as though he was trying to find something.

“Why did you stop? Is something wrong?” Becky asked as she tried turning her head to see what her brother was doing, but her view was cut off by the ledge of the window.

“No,” Phil answered as he looked down at his stepsister’s ass, perfectly framed by her tight leather pants. “Everything's perfect.” Then he whispered, “You're perfect.” Becky couldn’t make out the last thing he said and tried again in vain to look behind her at her brother. “Aha, here we go,” Phil exclaimed and suddenly she felt him tugging at her belt buckle.

“Phil! What the hell are you doing?” she said as loud as she could without rising above a whisper.

Phil just ignored her, as he was too busy trying to take off his stepsister’s belt. After a few seconds, Becky heard the clang of metal as the buckle came undone and swung into the side of the house and she gasped. She knew what her brother was planning on doing next. Her suspicions were confirmed as Phil began to pull down her pants, having some trouble pulling the tight material off given how she was bent over at the waist and her ass was sticking out towards him.

“Phil, NO!” Becky protested. “What the fuck are you doing?”

“Isn’t it obvious, sis?” Phil replied smugly as he finally managed to pull down her pants. He exhaled sharply and took a moment to enjoy the view of his stepsister’s perfectly shaped ass, covered only by a cotton candy pink G-string thong. Squeezing the flesh of her ass cheeks, he added, “I've been looking forward to getting a piece of this for a long, long time.”

“Ugh.” Becky felt a tingly sensation as her brother gently massaged her ass, a pleasurable one that also made her mad at how good it felt when she didn’t want it to. “I told you that you and I are not doing this anymore. Now get off of me, you pervert.”

“Yeah, well, I’m not quite done yet. There was something that you always refused to give me that I still want.” Becky’s eyes widened as she realized what her stepbrother wanted. “You always say that I’m a pain in the ass. Well-” Phil laughed lightly as he began to slowly, excruciatingly slowly, pull down her light pink thong. “That’s about to come true, literally.”

Phil unzipped his pants. Becky gasped at the sound. She had never let anyone fuck her in her ass before, and she still didn’t want anyone to, especially her perverted stepbrother.

“You can’t do this, Phil. I'm your sister for Christ’s sake,” she tried to plead, but her brother just laughed.

“Oh please, Becky. First, I’m your stepbrother, and two, you had sex with me for three months before deciding that you’d had enough of me.” Phil retorted. “Don’t act like I’m that disgusting. Granted, I am using the situation of you being stuck in a window to have anal sex with you, but at least don’t insult my intelligence by acting like we haven’t done anything sexual before.”

Phil pulled his almost eight-inch erect cock out of his pants and got into position, bending his knees slightly and aiming his cock straight at the opening of his sister's ass.

“Here’s how it goes,” He gave a small laugh. “Actually, this reminds me of our first time, when I caught you smoking weed and told you what would happen unless you did what I wanted. Well, here’s what’s going to happen tonight: you’re gonna let me fuck you in the ass, or I’m gonna tell mom and dad about you sneaking out of the house to go to Harper’s party, while being grounded no less.”

“You’ll get in trouble too, dickhead. I have photos of you at the party,” Becky reminded him in an attempt to stop him, but Phil only laughed.

“True, but you’ll be in far more trouble, seeing as how I’m not currently grounded. Besides-” Phil rubbed her ass again. “You’re totally worth it.

The compliment actually flattered Becky. She loved how much she was able to drive her stepbrother crazy, and she did in fact kind of miss having sex with him. Up until then, she had tried to deprive him of sex in order to punish him for being so annoying, but secretly, she always wanted more of him, or his cock at least. Still, she just didn’t want him in her ass, but she couldn’t afford having her parents finding out about her sneaking out of the house to go to Harper’s party, so…

“Ugh, so are SO going to pay for this, you asshole,” Becky chided him.

“If I recall correctly, you said the same thing the first time we did this, and yet-” Phil paused for effect. “You’re the only one that’s doing all of the paying.”

Becky scoffed.

“Whatever, you pathetic pervert. Just get it over with.”

Phil smiled.

“With pleasure, sis.”

Phil grabbed the base of his cock and slammed his shaft all the way into Becky’s virgin asshole; no warning, no slow entry, just fast and brutal. The pain of having her ass pierced by such a large cock for the first time, and so roughly, was so immense that Becky opened her mouth wide, but found herself unable to utter a scream despite how much she wanted to. Before the cascade of pain could even start to decline, Phil started pumping his cock in and out of her, sending fresh waves of pain throughout her rear.

“Shit, Becky,” Phil commented as he enjoyed the feeling of his stepsister’s tight asshole squeezing his cock. “You're really fucking tight, not like Harper. I guess she’s had a few too many cocks in her ass already.”

Becky wasn’t able to come up with anything to say to Phil as he thrusted himself into her repeatedly, all the while struggling to get her stepbrother’s cock out of her ass. Such squirming only added to Phil’s pleasure, making it seem as though his sister were actually moving her ass back and forth over his cock in pleasure. The more that she tried to resist her stepbrother’s cock, the harder her puckered asshole clamped down on his cock.

Phil leaned over Becky and reached into the window and around her to cup her breasts. Even though she was still wearing a shirt, her jacket was open and she was not wearing a bra. Her bra-lessness, coupled with the cool evening air, and the fact that she was actually starting to enjoy the feeling of a cock being slammed into her ass, made her nipples hard and erect, giving Phil something to run his fingers over and play with.

Becky gasped as her brother's fingers rubbed little circles around her nipples. Phil temporarily halted his thrusting and leaned into his sister to kiss her neck, his cock remaining fully buried in her ass. A long, quiet ‘Ohhh’ escaped Becky’s lips as he kissed her and she felt his cock fill her ass. Her stepbrother resumed fucking her, except this time it seemed that her asshole had finally begun to loosen up, as a full thrust of Phil’s cock from tip to base smoothly made its way into her ass, resulting in her moaning out loud yet again.

“It seems as though you’re starting to enjoy yourself, sis,” Phil commented in response to his sister’s moaning.

Becky let out another "ugh" at the fact that her brother noticed that she was starting to enjoy herself; she hated the idea of giving him the pleasure of being right while also getting to fuck her again. If he knew that she was starting to enjoy herself, then she figured she might as well try to enjoy it as much as possible.

“If you’re going to take so long fucking me, could you at least reach around and finger my clit for me? I can’t reach it.”

“Anything for such a good sister,” Phil replied as he took his right hand and moved it from his stepsister’s breast to her clit, which he then started to rub furiously, causing her to shudder as a new avenue of pleasure opened up to her.

Not having to worry about hiding her pleasure anymore, Becky began to let out a steady stream of "oooh's" and "aaah’s" as she enjoyed the feeling of having her ass fucked by her stepbrother. The pain of losing her anal virginity had just about disappeared, almost, and she loosened up further by allowing herself to enjoy her brother’s cock instead of trying to fight the feeling.

In response to his stepsister’s loosening asshole, Phil began to slide into her faster and deeper, causing him to hit the absolute deepest region of her ass and pushing her uncomfortably against the side of the house. Although she was really starting to get into anal sex, her brother’s increasingly brutal thrusting was too much for Becky to take, who up until three minutes ago, had never had a cock up her ass before.

“Oww,” Becky shrieked between two powerful thrusts. “Take it easy, would you? You're hurting me.”

“Sorry, sis. I’m kind of getting lost in the feeling,” Phil replied as he started to slow his thrusting a bit, allowing him to prolong the time before he came, and also allowing Becky to better enjoy her first anal experience.

“So, how long have you wanted this?” Becky asked Phil.

“A long time.”

“Since we first fucked, or after?”

Phil smiled and leaned down to kiss his sister again, and this time she turned her head slightly and they kissed each other on the lips.

“Since the day your stepmom brought you home to introduce us,” he finally replied and they both smiled.

“Ah, how sweet, but don’t go getting all sappy on me, bro,” Becky said, allowing herself to finally enjoy the taboo nature of her relationship with her stepbrother, just like he was. “You’ve slowed down. Come on, fuck me hard, I’m ready for it now.”

With a big, lustful smile on his face, Phil began to fuck his stepsister as hard as he could. Becky’s squeezed her eyes shut at the intense pleasure she was receiving, both in her ass and on her clit, which her brother had began to rub with a renewed vigor. Despite trying her best to muffle her cries of pleasure, a few "Oh fuck’s" and "Shit, shit, shit’s" escaped Becky’s lips as her ass was pounded by her stepbrother.

“Oh, God, oh God, you’re gonna make me cum. You’re gonna make me cum, stepbrother,” Becky cried out, causing Phil to increase the power of his thrusting even more. After a few more thrusts, she cried out in pleasure, as an orgasm rocked her body and threatened to cause her to lose her delicate footing.

Knowing that his turn was also about to arrive, Phil shoved his cock as deep as it could go just as he came in his sister's ass. With a grunt from both of them, Phil filled Becky’s asshole with hot, creamy cum. Becky could feel her brother’s cock twitch inside her ass as it let loose another two bursts of semen, causing her body to shake each time at the strange, yet highly pleasurable feeling. The two panted wildly in an attempt to catch their breaths, and after a minute, Phil’s cock began to soften. Eventually it slipped out of Becky’s ass and a stream of cum had begun to leak down her ass crack and even run over her clit.

“So, are you gonna get me out of here, big brother,” Becky said in a compliment to her stepbrother.

“Sure, it’s as simple as this.”

Phil pulled a piece of Becky’s jacket up and over a small, bent nail that had managed to pierce it as she tried to climb into the window. Turning to face her stepbrother, she turned to her brother...