With Sister's HelpbyHeyAll©
I had never thought of my 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 get a good job at a large firm in New York.
On the other hand, I lived at home with our parents and attended a nearby law school. Year end mid-terms were fast 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 & sexy older sister?
With Sister's Help
We were sitting in my room, home alone, and she looked at me with her large blue eyes and a smirk. Lizzie wore her old law school sweater and her long brown hair was tied in a ponytale. 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 asked playfully. "I never thought I'd live to see the day where my little brother 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 can be 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 case book. It's like I need a translator to decipher cases written in the early 16th century."
"Stop being so sarcastic. The early 1900's is not the 16th century."
"Maybe to you it isn't. Sorry, but I'm not a smarty pants like you are."
She raised an eyebrow, "Smarty pants huh? I'm glad to see that law school hasn't changed you. What's next, are you going to call me a tattle tale if I let mom know that you need to study harder?"
"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-assent, consideration, promissory estoppel, the mailbox rule..."
"Basically in everything that has to do with contract law..." 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 have at least known about those first points you mentioned by now."
I sighed, "Yeah, well I don't. It's hopeless Liz. I might have to retake this class for another year, or even 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. I'm sure 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 hates that class, how would learning it with them make contracts any easier?"
"That's a great point. See, you've got enough logic & reasoning in your brain to pass this class. My study partner for contract wasn't a first year student, he was second year student and he had the highest in his class. It was kind of like fate in a way because he had a huge crush on me, and I struggled in a class that he was great at. So we had a little deal going on which benefited both of us."
"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 you this 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 contracts. It's kinda dirty so you have to brace yourself if you want to hear it."
"Hmm...now this is starting to get interesting. I'm listening..."
"Okay, well, we had a little game where I would basically suck his dick a lot..."
"Jeez!! Liz...talk about having an awkward conversation."
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..."
"Well, we had a fun little thing going where he would write down the 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 my little oral fixation with him. It was beneficial for both of us."
"Oral fixation?" I asked 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. Sluts don't go to top law schools, nor do they graduate near the top of the class. I've been with less than 10 guys in my life. 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. "Now let's carry on. I think it might be best if we stuck with traditional methods of studying in your case."
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 this is such a good idea anymore. I shouldn't have even brought it up in the first place."
"Hold on a minute here. 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 sort of stuff with. Now let's move on."
"Don't you think if I had a girl to do sexual stuff with, I would be doing it already?"
"Fair enough," she nodded. "Then why don't you go out and find one? You should make an offer and suggest the whole studying thing."
"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," I replied.
"It certainly worked wonders for me," 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. Sometimes it would go the other way and he would perform oral on me. Contracts went from being my most dreaded class, to being my favorite. I never thought my oral fetish would ever pay off the way that it did."
A sudden surge rushed through my body and I found myself becoming 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 this is humiliating. 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? Well I'm glad to know that family boundaries don't mean anything to you," she teased.
"Hey, I'm just being honest here. You're the one telling dirty stories about giving oral to assist in your study habits."
"And it worked didn't it?"
"Apparently so," 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 was holding back her laughter.
"So...my little brother wants a blowjob from me huh? 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..."
"But you're saying that you wouldn't accept a blowjob if I offered one?"
"I...um...well no...maybe..." I stammered, struggling with how to respond. Deep down I knew the answer was clearly and unequivocally yes, but I couldn't let it show.
"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 a round trip ticket to Italy as a Christmas present. It's my way of thanking them for everything. So that pretty much left me short on cash for your present. I was planning on stopping by the mall for a cheap gift for you, but the weather sucks and being back home has made me lazy."
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 I would I would do that for you. All I'm saying is that I wouldn't mind playing a milder 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 sis. 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. There's no pressure or anything. Don't think I'm trying to force you to do something you don't want to do."
Without replying, Lizzie grabbed the left side of her sweater and tshirt, and yanked it up quickly before pulling it back down. Her bra was lifted in that quick moment as well. It was only a brief flash, but from what I could tell, her breast was perky looking and had 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 and analyze 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 right 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 little brother," she marveled. "Or should I start calling 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.
"Ummm...You're still sitting here," I pointed out. "If you're 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 seeing a raging hard on from a guy who's pent up?"
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 halfway up, and while trying my best to stay as calm as possible, I pulled my shorts and underwear down to reveal my hard cock which pointed upwards as a I sat back down.
"Look at that thing," she said in amazement. "It looks like it hasn't had any release in years. It actually does look kind of 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 handjob 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. You feel nice."
Her eyes were glued to my manhood as she continued her handjob. 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.
"Can I 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. My oral fixation is acting up. 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 oral experience to good use as she sucked and bobbed on my hard shaft. Her mouth felt warm & 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 shouted 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 got up and 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 remember? 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 mom," Lizzie replied. "I'm sure we'll work up an appetite by then. See you in the dining room in about 15 minutes."
"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 sucking my cock 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 won't go down no matter what I do."
"You're right about that," I agreed. "I've been pent up for way too long. What I need is something stronger or else I won't be able to walk out of this room by the time dad gets back."
"And 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 got 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 your jaw doesn't get sore 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 sweat pants down along with her panties. She used her feet to kick her clothes off to the side and stood uninhibited of her lower body 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 sis," I commented. "All these years and I had no idea you were this sexy."
She looked proud of herself. "Thanks little bro. 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 up 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 grabbing me by the wrist and walking us over to the bed where she laid down on her back, lifting her knees up to expose her private area to me.
"Good. Now let's get started. We haven't got all day. Plus I'm excited."
"Shouldn't we lock the door first?" I asked. "Mom could barge in at any moment."
She winked, "It's more fun that way isn'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 to get naked. Then I did what I normally do in this situation, which was to get down on my knees and start licking. She squirmed and shivered as my mouth worked it's magic on her labia and vagina.
"Oh god..." she moaned. "You've got an awesome tongue little brother."
"Just returning favor..."
My tongue went back to work licking and lapping her womanhood. Once she was wet enough, 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 hole. Her vaginal muscles twitched a little and even more clear fluids started gushing out. Her legs and feet seemed to twitch a little as well.