My First Sex With Sister's Help

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."

" 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!! 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. " 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.

" 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?"

" 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 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 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


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


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 checks 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.

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

stated almost impatiently.

I did as she told and stood back up with my hard cock pointing towards

her spread-open asshole. Her hands squeezed her butt checks even

harder and I pushed the tip of my erection against her anus. She

squirmed as I entered her. I took my time and her body adjust 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 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. We're so


"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 our mother walked away. We

were so close to getting caught, and it was obviously a real thrill

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 know that we're fucking

would we?"

"No we wouldn't."

I pushed my cock in and out as her anus and her 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 expose 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. They

were small and her areolas were light pink, and her nipples were a

slightly darker shade of pink.

I reached down as I continued fucking her up the ass to massage her

tits. Her nipples were hard and I pinched them with my fingers. All

the while I continued fucking her and filling the room with sounds of

my crotch slapping against the flesh of her rear end. 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 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 while 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."

"And I had no idea that my older sister was into this kinda thing."

Lizzie winked and stood up. "Older sisters 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

younger 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 big sis...I don't think I would have cum that hard

if it weren't for those gorgeous 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 around know...when everyone is asleep..."

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

The End
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