Emily's First Anal

At her high school graduation, Emily was feeling particularly excited. On one hand because she was going to a renowned college after summer, but more importantly it was because her older brother Dylan had promised her a very special gift if she graduated with good grades. She'd almost always been a straight-A student, except for that time back when she discovered masturbation. She got a few B's that year. But this time she got nothing but A's, which was to be expected, really, considering her track record - this year it was no doubt motivated in part by the potential of aforementioned special gift.

Her brother was a couple of years older than her, getting his master's degree next year. While not the best with studying nor grades, he was quite experienced in other areas of life... After the traditions and celebrations at Emily's high school were over with, the family all went out to a fancy restaurant for a celebratory dinner, and Emily and her brother made sure to sit next to each other at the table. Their parents, aunts and uncles were conversing among each other, so Emily turned to Dylan.

"You have no idea how excited I am for your present," she said in a hushed voice, inches from his ear. "I'm gonna die if you don't tell me. Like, at least give me a hint!"

He smirked and looked around the table, making sure nobody was looking their way. "It has something to do with you being on all fours."

She bit her lip, not quite able to figure it out - she knew it was something sexual, and they had fucked in that position many times. But why would that be such a special present?

"What do you mean?!" she asked impatiently, excited at the mystery.

"You'll find out later, don't worry sis," he said and looked away.

He put his hand on her thigh under the table, moving it upwards and under her skirt. She looked very anxious all of a sudden, and one of their aunts happened to look at her just then.

"Are you alright, Emily?" she asked as Dylan's hand moved further up Emily's thigh.

Emily nodded frantically as a few of their other family members looked at her too. "I'm fine, super great! Just really emotional about my graduation!"

Her comment was met with a few warm smiles, but then they turned around and moved on with their conversation from before.

Dylan didn't flinch, his hand now over her panties which were starting to get damp... She gave him the side eye, loving what he was doing but still angry with him for doing it here of all places! He shrugged and gave her an innocent smile, and with his palm on her pubic mound he pressed his fingers against her. Her eyes widened, and she was forced to hold back a whimper as he increased the pressure, forcing his fingers against her opening on the outside of her panties. She could hear a faint squishing sound from down there as her wetness reacted to the pressure. That was it - she couldn't take it!

Although he was only getting started, she hurriedly whispered him their safeword before she went crazy. For a moment, he was considering not respecting it - it was tempting to continue. He could tell that she really wasn't kidding though, it was simply too much. They liked to be quite daring when out in public when nobody knew they were siblings, but for Emily, it was far too daring to do this kind of thing right next to family!

He moved his hand away from her crotch, and left her to her own devices - her panties would only get even wetter though. Not only from what he'd just been doing, but also from how now she couldn't stop fantasizing about it - and plenty other things.

A couple of hours and a 3-course dinner later, they went back home. Their parents went to sleep almost immediately afterwards, but Emily and her brother stayed up - they had plans. Going into the living room, Emily planted her petite self down on the couch as Dylan just looked at her hungrily, lusting for her... She knew that he liked to look at whatever parts of hers whenever he could, and she loved the attention. So she hiked up her short skirt as she sat down in the couch, sitting with her legs spread in an at least ninety degree angle. Her white panties were showing how turned on she was. Upon seeing the sizable wet spot on them, her brother couldn't help but immediately get down on his knees in front of her.

"Slouch down," he said.

She did, and with her butt hanging slightly off the couch cushions, he pulled her panties off. She spread his legs wider for him, and then he went to town! Having longed for his touch since the charade at the restaurant, she grinned in ecstasy as she felt his fingers rubbing her moist slit up and down. She was wetter than she felt, her juices quickly being smeared all over her vulva and even inner thighs. He placed his thumb on her clit to gently rub it as he, with his tongue, penetrated her tight pussy. She threw her head back, grabbing her top and bra and pulling them both over her head in one swift move. All she was left wearing was the skirt which was not in the way, hiked up around her waist. She placed a hand on each of her small breasts, her nipples quickly stiffening as she played with them while watching her brother's stiff tongue going in and out of her in rapid movements.

It didn't take long for her to reach orgasm like that, her soft thighs trembling as they pressed against each side of his head as she rode out her climax. Afterwards, with the taste of her pussy still on his lips and tongue, he propped himself up and reached for her lips, kissing her deeply. Getting a taste of her pussy from his mouth, she moaned into him.

"How are you so good at that? I mean, oh my god," she laughed in disbelief.

They rolled around on the couch for a while, her near-naked body grinding against his clothed one as they made out - his bulge desperately pressing against her naked skin. She loved how it felt, and despite feeling like she could keep making out with him for hours on end, he couldn't take it. He was way too horny to go on like that.

He broke their kiss by leaving her soft lips to take her nipples in his mouth - one at a time of course - teasing them for just a moment before standing up. As he quickly undressed himself, she took her skirt off, tossing it carelessly on the floor next to them.

"Now for the all-fours part," he said with a smile.

He directed her to get on her knees and to spread them far apart, and to bend over. With her ass in the air, he smiled hungrily. His big cock was already about ready to burst, precum hanging from the tip. He could have very easily found himself sliding inside of her right then and there, and blown his load in minutes like he'd done so many times in the past. He contemplated that option for a second, biting his lip at the sight of her little pussy, glistening wet. Looking so alluring, so very luscious on display like that. He contained himself though, remembering the gift he'd promised her.

For a long time now, Emily had been asking him about anal sex. She'd never tried even putting a finger up there, it was simply the idea of it that she was in love with. She'd brought it up quite a few times, but each time he found a way to avoid it, change the subject, or pretend like he was busy. He was opposed to it because it was a way too naughty thing to do - as if fucking one's sister isn't naughty... With that said, he felt like he owed her for all the sexual favors he'd accepted in the past. Getting goodnight handjobs, good-morning blowjobs, good afternoon sex, and so on. He did return the favor once in a while by going down on her, but never even close to as many times as she'd serviced him - she was just the giving type, he reasoned!

But tonight was the night, and as he leaned in, he moved his flattened tongue along her slit, lapping up her juices in one go. He'd usually stop at her entrance, so she didn't expect him not to. She was exhilarated at what the present was going to turn out to be, waiting in desperation to find out. She wouldn't have to wait much longer though - because as he licked along her pussy, his tongue continued and only stopped once he'd given her *other* hole a good, long lick. She whined in excitement, smiling from ear to ear as he began to kiss, lick and tongue her anus. That tight, pink asshole of hers...

She was in that position for an excruciating amount of time, the feeling of her brother eating out her ass almost too much to bear. Droplets of juices were hanging from her labia, and some had already let go and dropped onto the couch. But she sat still, letting her brother work that magical tongue of his. A few minutes later however, he stopped. Her anus was at this point just as wet as her pussy was, but she didn't feel any other touch for the moment.

"This is the best present *ever*!" she exclaimed, not knowing that this wasn't even half of it.

He moved a set of fingers over her anus, gliding them up and down, in circles, and gently prodding at the tense hole. He figured that he needed a little more lube to get them in there, and so he moved his two fingers in front of her vagina. She let out a small moan as he drove them all the way inside of her, as deep as he could. But he wasn't about to finger her or anything. He just wanted to get her to relax back there, and to get his fingers lubed up more. And it worked - she loosened up a little bit from the pleasure of his fingers in her pussy. And as he pulled his fingers out, they were entirely coated in her natural lube.

Pressing a single digit against her anus, it took a little bit of force but he eventually managed to get it in there. He kept going, pressing further into her asshole. She held her breath, focusing on the pleasure of this new sensation. He moved the finger in and out a couple of times - all the way in, and all the way out. He pushed it in as far as he could, and started to fuck her with it properly, moving it only about an inch out before going back in. He got into a rhythm, letting her get used to having her asshole filled before he added a second finger. She could feel how inexperienced she was from how tightly the ring of her hole gripped around his fingers, but she let him force himself further inside her anyways. She closed her eyes shut, in pain from being stretched around his two fingers. It wasn't quite what she had thought it would be, and she even briefly regretted having asked for anal so many times! It hurt a lot - but it wouldn't take long before she begun immensely enjoying it...

As he slowly guided his two fingers further into her, she let out some heavy sighs from being in slight pain. She resorted to gripping a pillow with her hands, her knuckles going white as she firmly held onto it while she felt Dylan's fingers bottom out inside of her.

"I don't think I can take it much longer," she said.

Her brother's fingers sat still inside of her, not moving. He wanted her to get used to the size of them - it was double what she'd felt just now, after all! With his other hand, he gently caressed one of her butt cheeks.

"You're doing great, baby," he said, and knowing fully well the effect compliments have on her, he continued, "You look so fucking hot like this, do you know that?"

"Really?" Emily asked in glee, feeling weak in the knees all of a sudden.

"Absolutely," he said softly, "but to be fair, you can't not look hot."

She smiled warmly, and a few moments later he began withdrawing his fingers. She let out little sounds of enjoyment, the pain seeming to subside slowly but surely. He pulled them out until only the tips of his fingers were inside of her, and then he moved them back in all the way. He repeated that dozens of times, soon increasing the speed at which he was doing it until he essentially couldn't do it any faster. Pumping her ass with his fingers, she was moaning loudly at this point, and he had to remind her to keep it down because their parents were upstairs. She was in her own little bubble though, and had completely forgotten about everything else. She managed to keep it down, but only because of burying her face in a pillow.

Dylan was continuing to pump his fingers in and out of her, but with one last deep push, he pulled them out of her. Her pink hole was left looking plump and soft, definitely loosened up... Knowing she was ready, it only took one more thing to get to the good part. He stood up from the couch and stepped in front of her. Seeing as she could take a hint, she didn't hesitate to take his cock into her mouth. She'd always moan in desire whenever she initially got to taste him when blowing him, and this time was no different - it was better, even, on account of his tip being nearly entirely covered in precum, and a large droplet hanging from it too. She only barely managed to catch it on her tongue before it would have dripped down onto the couch, and as she accepted his hard cock in her mouth, she closed her eyes in enjoyment. The familiar taste was all too good for her, her lips moving back and forth on his shaft. He couldn't possibly be any harder than this, and once again he contemplated just blowing his load right then and there. He once more refrained from it, and instead summoned the willpower to exit her warm, wet mouth. She looked almost sad when he did, but he gently clapped her cheek.

"Time for your present, sis," he said.

Emily grinned in excitement, moving her upper body back down and her ass back up. She was swaying her hips from side to side in anticipation, and with Dylan's cock lubed up with his sister's saliva, they were ready to go. He wanted to be fully certain though, and ran his fingers from her clit to her hole, gathering up as much of her wetness as he could. He smeared it around her anus and then positioned himself directly behind her. He placed a hand on her hip, and with his other hand he placed his diamond hard penis at her hole. Feeling his head against her hole like that made Emily elicit a low moan of wanton lust. But he hesitated for a second, standing still. He couldn't believe he was about to fuck his sister in the ass.

"Come on Dylan... Put it inside of me already! Take my anal virginity," she said in impatience for him to get going.

Since he didn't seem to react, she instead decided to move herself backwards, and Dylan then felt his cock going ever so shallowly inside of her.

"Oh fuck," he whispered under his breath.

The sensation was too much, and he pushed forwards, the tip of his cock penetrating his sister.

"Mmh!" she moaned sharply.

In fulfillment from the entire head of her brother's cock going inside of her, she continued to push against him until he bottomed out. She certainly felt herself stretch to fit around his girth, but it was pure pleasure at this point.

Unlike when he was fingering her ass, he didn't gently move in and out. Instead, he took charge and grabbed her by her hips, steering her body back and forth in using her almost like a sex toy.

"Oh my god!" Emily exclaimed in surprise of how it felt.

She wasn't at all opposed to the way her brother was taking control. Her ass getting pounded created sounds that were like music in their ears. Her hole was comfortably snug around his shaft, and as he plunged himself in and out of her, she countered his thrusts by moving her hips back and forth.

Emily was dripping wet, the proof of her arousal dripping down on the couch in greater amounts than before. They were heavily breathing, moaning in unison as they fucked. The beautiful scene of his hard cock inside of her teenage ass would soon prove too much to handle for him, and he couldn't take it anymore.

"Em... Emily," he groaned in between thrusts, "you're making me cum!"

He only barely managed the warning, shooting rope upon rope of cum inside of her a second later. He bottomed out in her, his hands forcing her ass against his hips and cock. As deeply inside of her as he could possibly be, he sat still while he ejaculated, his cock spasming in climax. His sister's moans of satisfaction were all he was hearing as she felt the warm semen being shot into her asshole - her at this point well-used asshole.

She softly squealed at this new sensation, biting her lip white from how much it turned her on to feel his cock so deep in her ass, throbbing a few final times as the last spurts of cum shot into her. A few more dribbles of her girl drool soaked into the wet spot on the couch, and as he slowly pulled out, her asshole closed shut, looking nearly as tight as it was before.

"Put your panties back on so it doesn't get everywhere," he said.

She did as he said, and over the next several minutes, it slowly leaked into her panties. The same panties that were so very stained from earlier on. He leaned back in the couch, soon with his sister next to him. Cuddling up against each other, she looked up at him happily.

"Best present ever," Emily said with a grin, more than satisfied with her present.