Emily’s Lesson

It was the summer after Emily’s freshman year of college, and it was only the third time she had come home since her parents had dropped her off last August. It was great to finally be home for more than a few days, she thought. She was attending a big university several hours away, and the only times she’d been able to visit her family were for Thanksgiving and Christmas. Now, though, she had the entire summer back home in Florida to work on her tan, relax, and spend time with her family. She had really missed her sister, especially, while she was away. Alex was fifteen when Emily went off to college – she was just getting to the age when years didn’t mean so much and the sisters had more in common. Now, back for the summer, Emily was looking forward to the opportunity to reconnect with her sister.

Alex was 16 now, three years younger than Emily’s 19. It had been lonely for her, at first, when Emily left for college. She still had her year-older brother Joey around to hang out with, and they had grown closer over the past year, which was nice. But still, it was very different. There was no one at home to talk with about girl stuff – clothes, makeup… boys. She especially wished her sister was around so they could talk about boys. Alex had gone out with a few boys from school, and the farthest she had gone with any of them was kissing. Her last boyfriend, Mark, had gotten a few good makeout sessions before they ended up breaking up. The breakup was a shame, although Alex initiated it. She had really wanted to take their relationship to the next level, sexually, but didn’t really know what to do. Unfortunately, she had put it off too long, and Mark got impatient, apparently, and ended up coaxing a blowjob out of her slut friend Stacy. So obviously, Alex had to dump him when she found out. Alex was determined to get some advice from her older sister while she was back, so as to not let such a thing happen to her again.

The first week Emily was back, she and Alex got plenty of time to hang out. Their parents worked all day, so the sisters would typically wake up late, head to the beach, find some lunch, then either go back to the beach in the afternoon or hang out with friends, or just head back to the house. One morning, while the sisters were lounging around at home about to go to the beach, Emily brought up the subject of boys.

“So whatever happened to Mark, Alex?”

Alex told her the story of him, and Stacy.

“What an asshole! I can’t believe some guys!”

“Yeah,” Alex replied, “but I guess it’s not totally his fault.”

“Of course it is! He cheated on you, Alex…”

“I know, I know. What I mean is… I don’t know, I guess I can’t help but feel at least a little responsible… you know? I mean, we were together for a few months, and anytime he tried to do that kind of stuff with me, I shot him down. I can’t say I blame him too much for getting head from Stacy when I wouldn’t do it for him.”

“Oh… well why didn’t you do it for him? I’m just asking, you know – it’s totally cool if you want to wait for a while before getting into that kind of stuff. It’s definitely your decision. I’m just curious,” Emily said.

“I know… but it’s not that I didn’t want to… I was just sort of scared, you know? I didn’t know where to start, and I didn’t want to do anything wrong.”

“So you would have had sex with him if you knew what to do?”

“Well yeah,” Alex replied, “God only knows how many times I rubbed myself raw after I got home from one of our dates…! I would have loved to have gone all the way with him, but I’d just heard so many horror stories of girls’ first times, and I knew if I got him naked then I would want to fuck him, then I wouldn’t know how to do it right, and…”

Emily cut her off, “Calm down, sis! You’re underestimating yourself. But you’re right… from here on out, if you want to keep a guy, you’re going to have to give him a reason to stay!”

“What about you? How are you doing in the boy department? What are college boys like?”

Emily chuckled. “Well, if you must know, I’m doing quite well for myself. College boys only want to fuck… but, God, it’s so great! They take you out for dinner, then afterwards you go back to one of your places and give him a handjob or a blowjob or something… Then the next time, after the date, you get to fuck! Then after that, sometimes you don’t even go on a date… you just meet up for sex – between classes, in the middle of the night, whenever. And you can do it with more than one guy at the same time, too. Nobody cares!”

“Wow,” Alex said, “That’s awesome… but everyone doesn’t think you’re a slut?”

“Of course not, everybody does it this way.”

“Well in that case, I definitely need to figure this out before I get to college. I don’t want everyone thinking I’m a prude or something.”

Just then Emily saw Joey sleepily walking out of his bedroom towards the bathroom, wearing only his boxers. All this talk about sex had her thinking somewhat naughty thoughts about her little brother. He had really shaped up in the last year! A little bit of hair on his toned chest, some stubble on his face, nice abs… he was turning into one of the college boys she was used to having so much fun with.

“Well I’d like to help you figure it out, sis. What do you say I teach you how to pleasure a guy?” Emily asked her sister.

“Yeah, Em, that would be great… but how?”

Joey was walking back toward his bedroom when Emily stood up and called out to him. “Hey Joey, come her for a sec.”

Joey looked up, then walked into the living room. Emily walked up to him, then put her hands on his shoulders. “This is going to be so much fun!” she said to no one in particular.

“Follow me, you two,” she said to her siblings.

Joey was still a little sleepy after brushing his teeth and his morning piss, so he followed his older sister without much thought. Alex was a little confused, still not really understanding what her sister was up to, but she stood and followed anyway.

Emily walked into her room with her brother and sister behind her. She told them to sit down on her bed, and they did.

“What?” Joey asked her.

“Shut up, Joey. You’ll love this,” Emily said to him, standing in front of her siblings. “Okay, Alex,” she said to her sister, “the first step is to get the guy good and horny.”

“WHAT?” Joey said again. Alex looked at her sister incredulously.

“Okay, Joey, you’re done talking for the rest of the day. This is about our sister. And Alex, you wanted my help, so here it is.”

“Well yeah, but…” she replied.

“But, nothing. We need a guy for this, and Joey’s pretty hot if you forget he’s our brother. You’re actually pretty lucky, you know. And you,” Emily directed towards her brother, “you’re really fucking lucky, so just go with it, okay?”

“As I said,” Emily started again, “the first step is to get him good and horny. Usually this is done by the two of you making out.”

Alex took a sideways glace at her brother, then glared at Emily again.

“Go ahead, Alex,” Emily said.

“I don’t know about this, Emily,” Alex said, with a somewhat worried look on her face.

“Oh, for God’s sake!” Emily said in exasperation as she moved to the bed. She put her knees on the edge of the bed, on either side on Joey’s hips, and put her hands on his naked chest, pushing him back to a reclined position. She moved her hands to his shoulders, then lowered her face to his, pausing with her lips a fraction of an inch above his. Joey lay there, still in disbelief, with his lips parted. Emily pressed her lips to his, giving him an almost sisterly peck. Then, she pressed her tongue into his mouth finding his, closed her eyes, and gave him one sexy, several-second-long french kiss. She lifted her mouth from his, then stroked his hair with one hand as she went back down and sucked his bottom lip into her mouth. Joey finally moved his hands to rest on the sides of her ribcage as they finished their kiss.

Emily lifted her head a bit and looked at her sister. “See,” she said, “Joey’s willing to play. Why don’t you join in?”

Alex sighed, turned on by the sight of her two siblings entwined, then nodded. Emily raised up off their brother, and turned onto her side next to Joey. Alex was a little more hesitant than her sister, first gently taking one hand and resting it on her brother’s chest before sliding it down his abs to his navel. She smiled at her brother, then leaned over for a kiss. Instinct took over at this point, and Alex started making out with Joey like he was one of her boyfriends. She pressed her mouth over his, and took his lips in hers. He began to take initiative and slid his tongue in between her lips and into her mouth. Her tongue found his, and she let it swirl around his as they made out. She continued to rub her hand over his chest, and his hands found their way to the side of her head and her side. Emily took a moment to remove Alex’s shirt, which left her in her short shorts and bikini top. Joey enjoyed the fact that there was more skin to touch and his wandering hands began to turn on Alex that much more. He cupped her ass with one of his hands and gave a little squeeze. Alex cradled his head in her hands as she continued the assault with her mouth, stroking his head and hair as their warm mouths explored each other.

Emily reached her hand down to the crotch of Joey’s boxers, feeling the tent that his growing erection was forming. She then took one of Alex’s hands in hers and led it to Joey’s covered cock. Alex instinctively grabbed his dick through his boxers loosely in her hand, and began to rub around it.

“Okay children,” she said. “It looks like Joey is ready for step two.”

Alex removed her mouth from her brother’s and smiled, biting her bottom lip as she looked into Joey’s eyes. Joey couldn’t help but smile, not believing the turn that his morning had taken.

“Let’s start with a handjob. Sometimes, if you don’t want to go all the way with a guy yet, a handjob can be a good way of giving him something without doing too much. Joey, take off your boxers.”

Joey grinned, then was out of his boxers in record time. Alex’s lips parted as she stared at Joey’s erection. It was so big, she thought. So hard… so beautiful. His hard cock was angled up towards the ceiling, and his balls lay loosely below it. Joey propped himself up on his elbows, waiting for whatever it was to come.

“Nice dick, brother… I’m impressed! Okay, Alex. Wrap your little hand around Joey’s nice, hard cock that he is so kind to give us.”

She did as she was told, feeling how hard, yet how soft, her brother’s shaft was. Joey sighed at the feeling of his sister’s touch and let his head fall back. God, this was getting better and better every second.

“Now… pretty much, you just move your hand up and down on his dick. Don’t forget about his balls, too. Give them some attention, roll them around in your hand… Go ahead.”

Alex started to slowly jack off her brother, sliding her hand up and down his dick. With her other hand, she cupped his balls and lifted up a bit, taking their weight in her hand. She jiggled them around, smiling as she explored her brother’s body. She began to speed up her action… it was kind of fun. Joey’s breathing had also sped up considerably by this point. His cock felt harder than it had ever been in his life, and his sister was actually doing a good job. They were both starting to get into it when Emily spoke up.

“Well, that’s pretty much that.”

“What?” Alex asked, stopping the motion of her hand and resting her hand on Joey’s cock.

“I said, that’s a hand job. You did well. That’s about all there is to it.”

“But what about when he cums? I mean, what happens then? That’s the important part, right?” Alex said, confused.

Emily laughed. “Don’t worry about that, sis… I’m sure we’ll get to that part all too soon…”

Alex relaxed and lifted her hand off of her brother’s still-hard cock.

“A hand job is a great way to give a boy something to keep him coming back, without really giving him too much,” Emily taught her sister. “But,” she continued, “if you want to give him a little bit more, then we transition from using your hand to pleasure him to using your mouth.”

“Okay,” Alex responded, “What do I do?”

“It’s really hard to do it too wrong,” Emily answered, “but start by holding his dick in your hand and taking the tip into your mouth. The head of the penis is the most sensitive part, so it’s really important that you stimulate it. If you can take it further, then it feels really good to the guy if you’re able to take more into your mouth… It’s best if you let your lips and tongue rub along his shaft as you bob your head up and down on his cock.”

Joey smiled and eagerly nodded his head in agreement.

“Come on,” Emily said, “give it a try! Joey’s waiting…”

Alex smiled a shy smile as she was really about to cross a new barrier. Of course, today was the first time she’d ever held a guy’s cock, so that was definitely a milestone… But to actually take a penis in her mouth! That was a big step! And God, not to mention whose dick it was… her own brother’s! This was almost too much for her. She took a deep breath and re-gripped Joey’s dick. She looked up at Joey as her head lowered towards his crotch and saw his big grin. Well, if nothing else, she thought, she was helping out her big brother and making him feel good.

Her face stopped an inch from the tip of his dick. She gingerly extended her tongue until the tip contacted the head of his penis. At the moment of contact, his cock jumped at the sensation. She smiled, then swirled her tongue around the perimeter of Joey’s manhood. She took one hand and cupped his balls again, then enclosed the tip of his penis into her warm mouth.

“Ah… ohh, God, sis… that… feels so good,” Joey managed to say.

Joey’s encouragement made Alex feel a little bit more at ease. She took another half inch of Joey’s dick into her mouth, then pulled up to its tip. She started to get into a bobbing motion, able to take a little bit more of Joey’s cock into her mouth each time, until she maxed out at a little more than half of his length. She blew him slowly, drawing out her motions as her lips slid along all sides of his cock as she bobbed up and down.

“Okay, Alex… From the looks of Joey’s face, he’s getting pretty close to an orgasm. I don’t blame him… he’s had an exciting morning so far. You have a couple options here. You could either take it out of your mouth and jack him off as he cums; or, you could leave it in and let him cum into your mouth.”

Alex momentarily popped her brother’s dick out of her mouth to ask, “Which is better for him?”

“Leave it in,” both Emily and Joey answered at the same time.

Alex resumed the blowjob with a new sense of purpose. She was about to make her brother cum. The first guy ever that would orgasm as a result of her efforts and hard work… She had to make this good. She looked up at Joey and made eye contact as she sucked him. His face was scrunching up a bit, and his mouth was hanging open. He rested his hand on the back of Alex’s head and loosely grabbed her hair.

“Alright, Alex, here it comes,” Emily warned her sister, experienced with guys at their moment of orgasm.

Alex swirled her tongue around the tip of Joey’s cock as the first ribbon of semen spewed from his cock. She continued to suck him in as the second, then third, and fourth spurts of Joey’s cum shot into her mouth. Alex instinctively swallowed the thick liquid that was invading her mouth as she felt Joey’s balls twitching in her hand, feeding his cum into her waiting mouth.

Joey was mildly bucking his hips at this point, absolutely loving the warm sensation of his sister’s mouth enclosing his most prized possession as he came. He shot more semen that he thought he probably ever had before during this seemingly never-ending orgasm. Finally, his orgasm died down, his body collapsed, and he let out the breath he had been holding in for several seconds. Alex gave one last swallow and removed her mouth from his cock, letting it go with a sloppy ‘pop’. She smiled up at her brother with a small glob of his cum showing on her bottom lip.

“That was so fucking hot!” Emily said as she dropped to her knees. She took Alex’s face in her hands and, before her sister knew it, gave her a full-on, full-tongue kiss. Although surprised, Alex wasted no time in embracing her sister’s kiss. She moaned into Emily’s mouth as their tongues danced. Emily gave her sister one last peck on the lips, then caught the one glob of Joey’s cum that was still hanging on Alex’s lip with her tongue before she leaned back and admired her sister.

“Damn our brother tastes good, don’t you think?” she said.

Alex smiled as she sat back on her heels, tasting her brother’s flavor in her mouth.

Emily took the quiet moment as an opportunity to continue her lesson. “A blow job is always a good move. Apparently it feels amazing, so the boy is always satisfied if that’s as far as you’re going to take it that night. Also, guys are always way too excited their first time with you, so if you want to fuck him it’s still a good move to get him to cum once before he penetrates you. That way, he lasts longer when he does fuck you.”

“Before he penetrates me with this?” Alex asked, lifting and dropping her brother’s limp cock.

“Well, obviously we need to get him hard again…” Emily continued, “A good way to get him nice and horny is to let him eat you out. It’s a good way to get yourself warmed up, too.”

Joey already began to perk up a bit from the nature of his sisters’ talk.

“Okay…” Alex replied, a little nervous about completely exposing herself in front of her big brother, even though she knew it would happen eventually… and even though she had just swallowed a load of his semen. She kind of knew from the start that she and Joey would be fucking by the end of Emily’s lesson, but as of this point she was still wearing both her bikini top and bottom, and her shorts.

“Well, the first step is to get that top off…” Emily said, getting impatient.

Alex faced Joey on the bed, then reached up and untied her top, letting it fall to the floor. Joey was in awe as he stared at his younger sister’s full, perfect breasts. God, had her chest changed since last time he saw it when they used to bathe together as kids. Her breasts weren’t large, but they definitely weren’t too small. They were just… perfect. Small, dark, erect nipples capped the tips of her beautiful tits as they hung from her chest magnificently. Joey couldn’t help but stare.

“Alright Joey, I’m pretty sure instinct should take over at this point,” Emily coaxed him. “Make our little sister feel good.”

Joey tenderly reached out and cupped Alex’s breasts with both hands. He had never really fantasized about his younger sister before, but he had certainly noticed how she had grown into a beautiful young woman. It was never really sexual… he just admired her, he guessed. But now, it was definitely sexual feelings that he had. All of the pent-up, unrealized feelings that he had for his little sister came to consciousness as he held her breasts in his hands. He leaned his sister back until she lay flat on the bed, then he bent down and took one of her glorious nipples into his mouth and sucked. Alex dropped her head to the mattress and let out a sigh. Even after all the fun she and Joey had had this morning, this moment was still the first real sexual pleasure she had ever felt from a man.

Joey continued to tenderly suck on her breast as his hands wandered around her chest and abs, then down to her crotch. Alex jumped a bit at the feeling of his strong hand on her pubic mound, but quickly relaxed as she realized that she would rather be nowhere else at this moment. As he reached his mouth up to give Alex another sensual kiss, Emily helped out by first pulling off her sister’s shorts, then her bikini bottom. Both of Emily’s siblings were now completely nude.

The new change in attire allowed Joey’s wandering hand full access to Alex’s beautiful young body. His fingers found the entrance to her vagina as he continued to make out with her. As one of his fingers made its way into her sopping wet pussy, Alex came out of her stupor and began to rub her hands over her brother’s back. She gripped his shoulders as he began to finger her pussy.

“Ahh… that feels so nice, Joey…” Alex moaned as their mouths parted.

Joey slid down the bed until he was on his knees on the floor. Alex’s ass was on the bed with her pussy at the edge. Joey positioned himself so her legs were spread and resting on his shoulders and his face was near her crotch. He looked up as Alex grinned down at her brother, anticipating the pleasure that he was about to bring her. Joey concentrated his effort back to the task at hand. He had eaten out a couple of girls before, but he felt like he was really being put to the test here as his older sister watched.

Joey extended his tongue and let it drag across one of the outside lips of Alex’s sex. Her abs clenched and she drew a sharp breath in. Yes, she had masturbated before… but this was already so much better. Her hand came down to rest on the side of her brother’s head as he teased her. He continued to lick around her pussy without making contact until Alex broke down and pulled his face towards her pleasure center. He obliged and thrust his tongue into her.

“Oh God Joey, yes!” she yelled.

He swirled his tongue around inside her sex before contacting her clit, which sent her overboard. She clenched his short hair with both hands and spread her legs wide as he ate her out. The sharp pleasure she felt flooded her head and she lost track of time as her brother’s tongue worked wonders on her. Just as her breath began to quicken, she barely heard her sister once again call off their fun. She lifted her head and looked down to see Emily behind Joey with her head on his shoulder and her hand around Joey’s rock hard cock, gently stroking him.

“I said,” Emily repeated, “he’s hard again. It’s time for our Joey to fuck your brains out. You ready sis?”

Alex stroked her brother’s hair lovingly. “Oh yeah!” she answered.

Neither Joey nor his sister had been this far before. Although neither of them had previously considered the other a candidate for sexual pleasure, they were so entwined in their current affair that all they could think about was fucking. The two siblings wanted nothing more than to fuck each other until they were both satisfied.

“Alright, Joey,” Emily said, “this is your time to shine.”

Joey gave Alex one last lick for good measure, then rose to the bed beside his sister. He lay on his side next to Alex, and rubbed his hand over her stomach and breasts. He lowered his head to hers and forced his tongue into her mouth, where it swirled about with hers. While they kissed, he swung one leg between Alex’s knees as he settled himself on top of her, then he spread her legs with his other knee. He broke the kiss as Alex reached down and grabbed his hard cock, pointing it toward the entrance to her warm, sopping wet hole. He lowered his buttocks until his dick was pressed against her opening, then gave a push until the head of his penis was enclosed comfortably within her. Both of them stayed in this position as they breathed heavily, their mouths open, waiting for the next step. Finally, Joey grabbed her shoulders and pushed all the way inside her, letting out his held breath and nearly collapsing on top of her.

“Ahh… Oh, Joey… God… oh fuck,” Alex moaned. She breathed heavily, savoring the feeling of fullness she felt as her brother’s long cock was sheathed entirely within her. She relished the feel of his muscular body covering hers, his toned body pressed on her pert breasts, her nipples smashed to his chest, the stubble of his face resting against her smooth cheeks. She wrapped her arms around his body, her hands resting on his shoulder blades as they lay, growing accustom to one another.

Joey kissed his sister once again, then withdrew his cock from her. He gently slid it back into her warmth as she moaned, then withdrew once again. Alex’s lips were parted and her eyes were tightly shut, concentrating only on their joining. Joey was now getting into a rhythm, pulling out and entering again as Alex’s hands slid down to the sides of his rib cage. Joey sucked on the nape of her neck as he continued his assault on her body. Her legs wrapped around his lower back, pulling his cock further into her with every thrust as he continued to fuck his sister’s young body.

Alex loved the feeling of her brother inside her. She couldn’t imagine a person more suited to take her virginity than Joey, who she knew loved her and would take care of her. Likewise, Joey was certainly enjoying the sensations that his sister’s soft, slick, warm pussy was giving him as they were joined on the bed. Alex reached down and gently grabbed and massaged Joey’s balls in her hand as he fucked her. Every time his cock entered her body, it gradually stretched her insides until it bottomed out inside her as her narrow canal squeezed the head of his cock. Then she would feel him pull out until only his engorged head was left inside her. By now, she was getting warmed up to the point that her hips were beginning to rise and fall to compliment his thrusts. She began to buck her hips as a warm, tingling sensation started to build up in her loins. Her breath began to become sharper and more frequent as Joey’s efforts paid off.

“Oh God Joey, this is so… fucking… GOOD!”

His confidence boosted yet again as he sped up his thrusts. Alex wrapped her hands around her brother’s neck and pulled his face to hers, once again interlocking their lips and tongues as they pleasured each other. As the pleasure began to build within her to an almost unbearable level, Alex spread her legs wide and began to hump her butt off the sheets. All at once, the pleasure crashed down as she began to come.

Alex’s pussy began to rhythmically clench and release her brother’s cock as he pumped into her still. She closed her eyes and let out a soft, prolonged moan as her orgasm took over. Joey, realizing that his sister was cumming, allowed himself to finish as well. He grabbed her shoulders from beneath and pumped into her depths for all that he was worth. He released one strong rope of semen into his sister as his orgasm took over his body. He managed to pull his spewing cock from its home after the first spurt as he collapsed onto his sister. Joey continued to thrust as his cock slid, slick from his sister’s pussy, between his and his sisters’ stomachs, pressed tightly together. He squirted three, then four more gradually weaker spurts between their hot bodies until he finally completely collapsed onto Alex.

They lay there catching their breath for several moments as they regained composure from their mutual orgasm, their sweaty cheeks pressed against one another. Finally, Joey raised up onto his elbows, separating their stomachs and leaving a string of cum connecting them. He rolled onto his side and stared at his sister, drained and sexually satisfied. She opened her eyes weakly, smiling at her brother with her hand on his side. She eyed him up and down, from his sweaty matted hair to his heaving toned chest to his gradually softening cock, admiring the man that her brother had grown into. She wiped his cum from his stomach and spread it onto hers, joining it with the semen that he had deposited on her during his orgasm.

“I’m almost speechless,” Emily said, watching her siblings in their post-orgasmic glow. “I’d have to say our lesson is complete. You’re ready for college, little sis!”

“Maybe…,” Alex said, biting her bottom lip and still looking at her brother. “But I think we might have to practice again later, just to make sure.”

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