With Sister's Help

byHeyAll©

I had never thought of my older sister in that way before.

Sure, she's smart, funny, and incredibly attractive; but I had never fantasized about her in my entire life- honestly.

Things changed when my sister came home for the holiday season in December. She had recently graduated with honors from a top law school and was able to land a starting position at a major firm in New York.

On the other hand, I lived at home with our parents and attended a law school nearby. Midterms were approaching and I considered it a huge relief to have her around to help me study. After all, what's more motivating than a smart and sexy older sister?

With Sister's Help

We were sitting in my bedroom, home alone, and she looked at me with her wide blue eyes and a smirk. Lizzie wore her old law school sweater and her long brown hair was tied in a ponytail. My binder was wide open and my books were on display. We were ready to study.

"Well aren't you glad to see me?" she said playfully. "I never thought I'd live to see the day where you would be fawning for my help."

I cringed at her teasing, "Yeah, well this stuff is hard. I mean, not all of it; criminal isn't bad. Torts is okay. But contracts is a real nightmare. Most of the time when people are talking in that class, I have no idea what's going on. And don't even get me started on that book. It's like I need a translator to decipher cases written in the early 16th century.

"Oh, stop being so sarcastic. The early 1900's are a lot different than the 16th century."

"Maybe to you it is. Sorry, but I'm not a smarty pants like you are."

She raised an eyebrow, "Smarty pants? I'm glad to see that law school hasn't changed you. What's next, are you going to call me a tattletale if I let mom know that you need to study more?"

"Very funny," I replied.

Lizzie rubbed her hands together to show that she was ready to begin. "So... where should we start with this? The exam is next week, right?"

"It is. And we could start with mutual-manifestation-of-consent, consideration, promissory estoppel, the mailbox rule..."

"Basically the whole thing..." she said, cutting me off.

"Pretty much. Like I said, I don't know shit in that class."

"Yikes. That's kinda scary at this point. You should at least have known about those first points you mentioned."

I sighed, "Yeah, well I don't. It's hopeless Liz. I might have to retake this class for another year, or worse, I'm even considering dropping out of law school all together."

"Cut it out," she said playful, but with sincerity. "You're a lot smarter than that and all you need is a little one-on-one attention. Believe me, contracts was no picnic for me either. Hardly anyone liked it. But I applied myself and got through it. And you can do the same if you work just a little harder at it."

"Any useful tips?" I asked. "You make it sound so simple."

"Try getting a study partner. It worked wonders for me."

I winced, "But if everyone hated that class, how would learning it with them make contracts any easier?"

"That's a great point. See, you've got enough logic and reasoning in your brain to pass this class. My study partner for contracts wasn't a first year student; he was second year student and he had the highest gpa for that year. It was kind of like fate for me in a way because he had a huge crush on me, and I struggled in a class he was great at. So we had a little deal which both of us benefited from."

"Well that's the advantage of being a pretty girl," I quipped. "I doubt there are many smart second year dudes lining up ready to tutor me in a class they've already passed. You'll be gone in a few weeks, so there goes you being my study partner."

She paused for a moment and it looked as though she was struggling with herself about what to say next.

"Fine," Lizzie sighed. "I'm only telling this little secret because you're my younger brother and I love you dearly, but my study partner and I had a little game which helped me learn quickly. It's kinda dirty so you have to brace yourself for that."

"Now this is starting to get interesting. I'm listening..."

"Okay, well, we had a game where I would basically suck his dick a lot."

"Jeez!! Liz... talk about being awkward."

She shrugged, "What? I warned you and you said you were interested. This is for your benefit, not mine."

"Yeah, I guess you're right about that. And I still think this sounds interesting. Go on."

"Okay, so, he would write down key notes for me to memorize, then when we had time, we would meet and he would quiz me on it. If I got the answer right, he let me indulge in my little oral fixation with him. It was beneficial for both of us."

"Oral fixation?" I said in surprise. "This just keeps getting weirder and weirder."

She gave me stern look as if she felt insulted. "I'm not a slut, okay? I've been with less than 7 guys in my life. Sluts don't go to top law schools and graduate near the top of the class. I'm a healthy young woman with needs like everyone else, and I'm trying to help you."

For the first time in my life, my own sister struck a sexual cord with me. I've always thought of her as being really hot and a cool person, but hearing her talk so candidly about her carefully guarded sex life was a surprising thrill.

"I don't think you're a slut. Believe me, you're one the smartest and classiest girls I've ever met. And I really do appreciate you helping me with all this. I'm just a little surprised, that's all. You've always been really private about this sort of thing."

"Good," Lizzie nodded, with a hint of embarrassment. "Now let's carry on. I think it would be best if we stuck with traditional methods of studying."

I quickly interjected, "Whoa, wait a second. What happened to this new approach you were talking about? I never said that I wasn't interested in hearing more about it."

"Ummm... I don't know if that's such a good idea anymore. I shouldn't have even brought it up in the first place."

"Hold on a minute. Liz, I apologize if I was being immature and inappropriate a moment ago. I promise to be respectful of whatever it is you have to say about your unconventional study habits. It does sound very promising to my educational success."

I tried my best to appeal to her strong sense of being a self-professed liberated feminist, and it appeared to work as she made her thinking face and gave it a thought.

"Alright," she cautiously replied. "So, you should find a female partner to do that with. Now let's move on."

"Don't you think if I had a girl to do sexual stuff with, I would already be doing it?"

"Fair enough," she nodded. "Then why don't you go out and find one? You should make an offer and suggest the whole studying arrangement."

"I'm sure that would go over well. But seriously Liz, that does sound like an interesting set up you had. I know I'd be an expert in the law by now if I had a girl to do that kind of stuff with."

"It certainly worked wonders for me when it came to that class," she smiled. "I remember being in class thinking about sucking his cock after. He had a nice cock so I made an extra effort to memorize everything I needed to know so that I could suck it. Contracts went from being my most dreaded class, to being my favorite. I never thought my oral fetish would pay off the way that it did."

A sudden surge rushed through my body and I found myself becoming very sexually aroused hearing her talk like that.

Her eyes squinted and she looked down at my crotch. "Is that... is that what I think it is?"

"It's nothing," I quickly replied, pulling my sweater down over my shorts.

"Did I just give my little brother an erection?" she asked with a grin.

"Oh god. What did you expect, Liz? That was a pretty provocative story, and in case you didn't notice, you're hot."

"So you think I'm hot and now I gave you a hard on?" she teased. "Well I'm glad to know that family boundaries don't mean anything to you."

"Hey, I'm just being honest here. You're the one telling dirty stories about giving oral to boost your grade."

"It worked, didn't it?"

"Apparently," I replied. "And I'm sure it would make a great gift for the holidays as well."

There was a sudden awkward pause in the room as we both realized what I had just let slip. I was speechless and she looked like she held back her laughter.

"My little brother wants a blowjob, eh? Or did you want to eat my pussy?" she asked with a smile.

I tried my best to do damage control. "You know that isn't what I meant. You're really pretty and all, but..."

"You're saying that you wouldn't accept a blowjob from me if I offered?"

"I... um... well no... maybe..." I stammered, struggling with how to respond.

Deep down I knew the answer was clearly and unequally yes.

"Look, I really don't mind if you would," she replied bluntly. "But here's the thing, I used up most of my extra cash to buy mom and dad something nice for Christmas. It's my way of thanking them for everything. So that pretty much left me short on cash for you. I was planning on stopping by the mall for your gift, but the weather sucks and I don't want to go out."

I tried my best to contain my excitement. "So you're saying you would... you know... to help me study..."

She rolled her eyes and smiled, "You wish. All I'm saying is that I wouldn't mind playing a version of that game with you. I want you to do well in school, and if it means that I'll have to show you my tits or something to motivate you, then I'll do it."

I suddenly found myself talking rapidly as a way to hide my nervousness. "I don't mind that at all. I mean, uh, I don't mind if you don't mind. It's not a big deal. Nothing serious. You don't have to if you don't want to. But yeah, I guess it would help if you did. That is, if you want too of course."

Without replying, Lizzie grabbed the left side of her sweater and tshirt, and yanked it up quickly before pulling it back down. It was only a brief flash, and from what I could tell, her breast was perky looking with a light pink nipple.

"Oh... that was really nice. I didn't think you were actually serious about this."

"Well I was," she smiled. "And you'll get to see the rest once you memorize the main elements of contract law. I'll test you on it tonight along with some hypotheticals to see if you can apply it correctly, and if you do a good job, you get to see both of my tits for a reasonable amount of time."

"I'm going to have to wait until tonight for that!? I thought the purpose of this was to help me study now? God, I'm rock hard over here. It aches so bad it almost hurts."

My sister reached down and briefly touched my stiff erection through my shorts.

"Yikes! You weren't kidding about that aching part," she marveled. "I guess I might have to call you big brother now. That thing feels like a steel rod."

I nodded. "Yeah, I haven't gotten laid in a long time. And all this stress had really taken away all my desire to... you know... masturbate and relieve myself. But hearing you talk about oral sex and then flashing me has really woken things up in a big way, if you know what I mean."

She raised an eyebrow, "Then I suggest you take care of that right now if it's interfering with your ability to study."

It was hard to tell what she was thinking at that moment. She looked kind of serious, but also kind of playful. She had practically told me to masturbate to get rid of my erection, but she just sat there staring at me.

"You're still sitting here," I pointed out. "If you were serious about that, you might need to give me a little more privacy."

"I think you're forgetting some of the points of the deal I made with my study partner. I gave him something, which was oral sex, and he would also perform oral sex on me. It was a mutual exchange. So if I'm going to show you my tits later, I would also need to see something in return. And what better than a raging hard-on from a guy who's pent up?"

"Seriously?

She nodded. "Yes, seriously."

My heart raced. My sister was dead serious about seeing my hard cock, and the thought of actually showing it to her was an unreal thrill in a way that I had never imagined.

I stood slightly, and while trying my best to stay as calm as possible, I pulled my shorts and underwear down to reveal my hard cock which stood straight up as I sat.

"Look at that thing," she said in amazement. "You look like you haven't had any release for years. It actually does look painful."

"Tell me about it. With a sex drive like mine, it feels like it's already been a decade. Anyway, I'm in serious need of relief. What do you want me to do now? Jerk off in front of you?"

She reached down and stroked my hard cock for me. "That was the original deal. But my gosh, there's no way I can resist not touching this. Brother or not, you've got an irresistible cock."

Her hand gripped my shaft and began to stroke me up and down. As expected, it felt amazing. The fact that I was getting a hand job from my own sister was an extra bonus since it was so naughty.

"Holy shit that feels fantastic," I sighed. "It's been a while since I've felt a woman touch me like this."

Lizzie gripped my cock even tighter and stroked with even more vigor. "And it's been a while since I've felt a cock like this as well. You feel nice."

Her eyes were glued to my manhood as she continued her hand job. Never in my life would I have ever imagined that I would be doing sexual stuff with my sister of all people. The more she stroked, the harder I seemed to become and the more attention I needed.

Suddenly, she got down on her knees.

"Do you want me to suck it?" she asked innocently, like it was no big deal.

I nervously replied, "Um... yeah. Sure, if you want too."

She continued stroking me while on her knees and she gave the head of my cock a little kiss.

"Yes, I want to. It's kind of been a fantasy of mine for a while now. You can consider this an advance on your Christmas gift."

With that said, she swooped down, and in one motion, she engulfed most of my cock in her mouth. She put her experience to good use as she sucked and bobbed on my hard shaft. Her mouth felt warm and wet, and her suction was incredibly tight. Getting a blowjob from my own sister felt phenomenal as she put her self-proclaimed oral fixation to good use. Her head moved up and down faster and faster. The room was silent except for all of the sucking and slurping noises she was making. That was, until...

"Hello, anyone home?" mom hollered as she came home from work.

As always, she entered through the front door, while my sister and I were upstairs in my room with the door wide open.

My sister quickly walked towards the hallway to greet her. "We're in the middle of studying, mom. I'm making sure that my little brother gets an A+ in his contracts class. That's the class I told you I had a hard time with. I'm teaching him my study tips."

"That's very kind of you sweetie. I've got some leftover holiday pastries from a party at the office. Your father should be home soon. Maybe we can all have a snack together in a few minutes."

"Sounds great," Lizzie replied. "I'm sure we'll work up an appetite by then. See you in the dining room in a moment."

"Wonderful. And tell your brother not to work too hard," mom replied playfully. "At this rate, he'll have a meltdown if he doesn't relax."

"You don't have to worry about that mom! He's in good hands!"

Lizzie smiled and swiftly headed back inside my room and shut the door, returning to her rightful spot between my legs.

"Now where were we?" she asked rhetorically before continuing to suck me off.

"God that was close. Hearing you talk to mom after giving me oral was a surprising turn on. I think I'm even harder than before."

She took my cock out of her mouth again. "Tell me about it. And you're right about being even harder. This thing just won't go down, no matter what I do. The average guy would have been finished a while ago."

"You're probably right about that," I agreed. "I've been pent up for way too long. What I need is something stronger else I won't be able to walk out of this room by the time dad gets back."

"What did you have in mind?" she asked with a skeptical look on her face.

"Sex? Do you think we could try it? It's been forever since I've gotten laid and it's the only thing that keeps me calm."

"Whoa... Giving you a blowjob is one thing, but actually having sex with you is something else entirely. Besides, I'm not on the pill."

"Fine," I replied. "But I hope you don't get a sore jaw easily. This might take a while."

She put her hands on her hips and gave me a stern look. "Make it fast. And only because it's the holiday season. Don't expect this to happen again okay?"

Lizzie stood up pulled her sweatpants down along with her panties. She used her feet to kick her clothes off to the side and stood uninhibited of her nudity. And of course, my eyes took in everything they could. She had long and slender legs, and her crotch looked freshly shaven. Best of all, I was able to catch glimpses of her pink labia when she kicked her clothes off.

"Holy shit, nice body," I commented. "All these years and I had no idea that you were this sexy."

She looked proud of herself. "Thanks I could say the same about you. Anyway, I'm not on the pill like I said, so we'll have to try something else to relieve you. Do you like anal?"

A sudden shiver went down my spine and I found myself becoming even hornier and even more excited.

"I fucking love having anal with girls," I proclaimed. "Not many like it though. So if you're offering, then yeah- I'd love it."

Lizzie wasted no time, grabbed me by the wrist, and walked us over to the bed where she then laid down on her back, lifting her knees up to expose her private area to me.

"Good. Now let's get started. We don't have all day. Plus I'm excited."

"Shouldn't we lock the door first?" I asked. "Mom could barge in at any moment."

She winked, "That makes it more exciting, doesn't it? Now make sure things are nice and wet before you enter. And go slow..."

I took a deep breath and pulled off my sweater and tshirt. Then I did what I normally did in this situation, which was to get down on my knees and start licking. She squirmed and shivered as my mouth worked its magic on her labia and her vagina.

"Oh god..." she moaned. "You've got an awesome tongue little brother."

"Just returning the favor..."

My tongue went back to work licking and lapping her soft labia and vagina. Once she was wet enough there, the fluids from her cunt along with my saliva leaked down and coated her tight little brown anus. She spread her butt cheeks apart and I used my finger to lubricate her asshole.

"Stick your finger in," she said. "Don't be shy. It needs a little loosening up first, don't you think?"

I did as she asked and pushed my finger inside her anus. "You bet I do. I love how tight you feel."

My finger went as far in as it could go in her little hole, and I moved it in and out. More than anything, I loved seeing how her body reacted to something foreign penetrating her most intimate area. Her vaginal muscles twitched a little and clear fluids started to gush out. Her legs and feet seemed to twitch a little as well.

"Enough with the teasing already. I'm ready. Just fuck me," Lizzie stated almost impatiently.

I did as she was told and stood back up with my hard cock pointing towards her spread-open asshole. Her hands squeezed her butt cheeks even harder and I pushed my erection against her anus. She squirmed as I entered her. I took my time and her body adjusted to my cock. Inch-by-inch, I slowly slid my way inside of her.

As good as my sister's tightness felt against my cock, it was equally as exciting seeing her make faces as she tried to hide the pain.

Suddenly, with my cock nearly all the way in, I heard my mother's footsteps before she knocked on the unlocked door.

"Your father is home. I made some hot chocolate with marshmallows to go along with our Christmas treats."

"We'll be out in a minute!" my sister shouted with my cock up her ass. "I'm in the middle of teaching him about contract formations. It's a pain in the ass but we're so close."

"That's good. I'll keep the drinks warm on the stove until the both of you come down. Don't keep your father and I waiting too long.

Lizzie wrapped her legs around my backside in an attempt to get to fuck her again while she continued talking to mom through the door.

"We're coming soon," she playfully replied. "See you downstairs in a minute."

"Alright you two."

My sister and I smiled at each other as mom walked away. We were close to being caught and it was obviously a real thrill her for her.

"Why do I get the feeling that you enjoyed that?" I asked.

"Because I did. This is the most fun I've had in a long time. Now hurry up. We wouldn't want mom and dad to get suspicious of us, would we?"

"No we wouldn't."

I pushed my cock in and out as her anus and rectum loosened up to my size. Her breathing became more labored and her eyes had that classic 'fuck me' look from a woman who really needed it.

"Oh god..." she moaned softly. "Fuck me like that. Fuck..."

Lizzie rubbed her hands all over her body, and suddenly, she pulled her sweater and tshirt up to her bare stomach and her bra. Her hands ran all over her waist and chest. Then, to my delight, she lifted both sides of her bra to expose her bare breasts to me. The were small and her areolas were light pink, and her nipples were a dark shade of pink.

I reached down as I continued fucking her up the ass to massage them. Her nipples were rock hard and I pinched them with my fingers. All the while, I continued fucking her ass, filling the room with sounds of my crotch slapping against the flesh of her posterior. She continued to make faces, showing the pleasure she was receiving, and she tried her best to keep her moans down.

"I'm going to cum in a moment," I huffed, with my hands still all over her breasts.

Lizzie reached down and rubbed her engorged clit. "Me too. Shit this feels great."

An overwhelming feeling swept over me and it felt as if my cock was relieving my body of a ton of pressure. Load after load of my cum shot inside my sister's rectum. Each pump I gave brought me even more pleasure, and I watched her orgasm before my very eyes and she rubbed herself furiously. It was obvious that her orgasm was every bit as powerful as mine, as her back violently arched, her toes curled, and her eyes nearly rolled back, before she stopped and went limp.

When it was over, I pulled my limp cock out of her anus and laid next to her.

"God, that was fucking amazing," I panted.

"You bet it was. I had no idea my little brother was such an amazing fuck. I'm going to have to study with you a lot more often now."

"I had no idea older sisters were into this kinda thing."

Lizzie winked and stood up. "Only older sisters that can be naughty when the situation calls for it. That would be me. And you would be surprised to know how many other 'big sisters' wouldn't mind screwing their little brothers."

"Is that right?"

"It is," she nodded.

She pulled her top down to cover her breasts, and she walked over to a nearby table to grab a piece of tissue paper to wipe some of the cum that was dripping down between her thighs.

"You know something," I said. "I don't think I would have cum that fast or as hard if it weren't for those tits of yours. You've got nice tits along with a great ass and body. This was so hot."

She smiled as she pulled her pants up. "Well I had to pull them out, they were swollen. Anyway, I can hear mom and dad talking downstairs, let's not keep them waiting any longer."

"Do you think we can continue 'studying' again soon? Maybe we can finish this at night... you know... when everyone is asleep..."

Lizzie bent down and gave me a kiss on the lips. "It's a study date."

With that, she opened the door and walked across the hallway and down the stairs to greet our waiting parents, with her asshole filled with my cum.