My Sister Practices Diligently

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After some doubt I find my sister's idea worthy of a prize.
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imhapless
imhapless
3,575 Followers

All characters are and were 18 or older at all times where there were any sexual feelings or contact.

Growing up I had two sisters, one a year older and one a year younger. We grew up in a conservative part of the Midwest with our mom and dad. I was a fairly normal guy, though a little bigger than average, who was so devoted to sports I came upon other things in life a little later than most.

My mom and dad were pretty normal conservative folk; they and I sometimes thought my sisters were from a different planet than we were.

My older sister Jill at 19 was tall (about 5' 11", only about 3 inches shorter than I am), had an athletic build, long blond hair, and steely gray eyes in an otherwise very nice (though not gorgeous) face. Also – I only started noticing this when I was 18 – she has very shapely legs, a bubble butt, and high poke-in-your-eyes tits. She is a perfectionist, and was also a late bloomer. She works at something until she gets it right, and has from the time she was a little kid. Two examples:

She had a volcano as a science experiment she designed when she was about 10. She made, at one time or another, every member of the whole family help her set up and test her volcano at least 20 times over a three day period before the science fair. Of course it worked perfectly then, and she won 2nd prize.

As a second example, when she was 14, though she had never played softball before, Jill decided she wanted to make the high school team. She made our dad, me, or both of us play catch with and/or pitch to her at least an hour every day during the entire summer. Sometimes she would have me and some of my friends out there three hours playing with her even though her skill level was way below ours. But she was always kind to me and fun, and my friends always liked her, so there was no problem. Needless to say she not only made the team but ended up the starting first baseman.

Jill was also outspoken, and had no problem saying what was on her mind. This sometimes got her in trouble in school and with our parents, but she was always sly and smart enough to get out of it without significant consequences.

My younger sister, Kate, is very different. She is short, about 5' 3", with short brown hair with natural streaks of red, green eyes, a beautiful face, totally curvatious, and top heavy (her tits were way too big for her slim waist). She is usually a typical follower. Not as smart or as talented as Jill, she still wanted to do most of what Jill did, and succeeded most of the time (although to a lesser extent) in school and sports, and was probably the most popular girl in her class.

Soon after Jill turned 19 I started noticing changes in her behavior. She started wearing makeup and skimpier clothes, seemed to grab her crotch and breasts a lot around the house, and often asked me weird questions about guys at school. My mother apparently noticed changes in her too. One day when I was going through the medicine chest in the bathroom I shared with my sisters I came upon some prescription pills of Jill's, each pill separately packaged in a blister pack. She walked in about that time, took them from me, and said something like "Mom said you're not supposed to see these pills she got me from the gynecologist," and walked out with them.

One summer day before Jill's senior year and my junior year in high school, our parents went for an overnight at some relative's house, and we three kids were alone for an entire Saturday and Sunday morning. We did our own thing during the day Saturday, Jill and I cooked dinner, the three of us ate together, and since none of us had any plans with friends we played some video and card games, and then decided to watch a DVD. Kate didn't like our choice and said it was that time of the month for her anyway, so she went to bed about 10, leaving Jill and I with the movie.

The movie had many sex scenes and sexual overtones, and Jill was acting weird, including rubbing body parts, and squirming around, apparently immune to the fact I was nearby. At one point she said she had to pee, told me to put the movie on pause, and came back wearing only – as far as I could see – a long T-shirt. Her constant rubbing of her crotch and tits were too obvious, and I didn't like the effect it was having on me, so I asked her "What the hell are

you rubbing yourself for Jill?"

To my surprise she put the movie on pause, turned to me and said "Tom, have you had sex with any of the girls at school?"

I wasn't sure I wanted in on this conversation, especially knowing her characteristic directness, so I said "Should we really be talking about this?"

She then turned the movie off, sat next to me on the couch with her legs crossed and her T-shirt hiked up near her crotch, and made it clear that we were going to have a discussion about sex. So I swallowed hard and primarily listened, because even when she asked me questions she rarely waited for an answer.

In her typical direct manner she said she had started to really badly want to have sex, but thought she was way behind other girls, and didn't want to make a fool of herself with sexual partners. She told me I should be interested in that too, and that the best way for us to go about it to gain some experience without being buffoonish was to experiment with each other. She said she had gotten as much information as she could from reading, and now needed some actual "field work".

With that, she stood up and pulled her T-shirt over her head, exposing her glorious – My God was it Glorious – completely nude body. My dick was instantly rock hard.

She apparently was a little non-plussed by my wide eyed, gap-jawed, staring, and barked – "I know you're on porn sites all the time; you've seen naked women before. Now I need your help because I don't have a dick, or a tongue that will reach the places I need, so you have to help me out. Now close your mouth and take off your clothes."

To be honest, I felt like a zombie at that point, my mind shanghaied by the site of her breathtaking body. Knowing how relentless Jill was and how anxious I was to see where this was going, I did as instructed. But I was still inhibited and undressed hesitantly, so she got impatient and started pulling my clothes off faster. Her first

comment when my boxers dropped was,

"Wow, is your dick always like that?" to which I replied "No, only when it's aroused."

Her next comment, "Alright, I want to give you a blow job. You critique me as I'm doing it and let me know what I can do better".

Without waiting for a response from me, she pushed me down on the couch, knelt down between my legs, and started sucking and tonguing my dick like it was the last ice cream cone on earth. Holy shit did it feel good! I had only two other blowjobs in my life, and this was off the charts better than either of those. I could barely breathe, let alone talk, as she ran her lips, tongue, and lightly her teeth, up, down, and around my head and shaft, every once in awhile sucking so hard and long she looked like she wanted to siphon a swimming pool. At the same time she was massaging my balls – WOW, what magic fingers!

It wasn't long before I told her I was about to cum. She immediately stopped, and unemotionally said, "Not until we talk about what I do with your ejaculate." Her sudden stoppage and words made my dick and balls calm down a little, but my brain was still spinning.

"Why didn't you give me any advice while I was working on you?"

"Geez, Jill, you did it so well I didn't know how you could possibly do it better. That's why I didn't say anything."

She smiled but then quickly got back on topic, "What do guys want girls to do with the cum when giving a blowjob?"

"Well, uh, most guys would love the girl to swallow it, but it may be difficult for the girl to do. You could spit it out if you chose, or just pull your mouth away and let it hit where it might."

"Would I appear more experienced if I swallowed?"

"Uh, yeah."

"That's what I'll do then," she matter-of-factly shot back.

Without further hesitation, she started back on me and had me rocketing my wad in less than a minute. It felt SOOO much nicer than masturbating or the other blow jobs I had gotten, and I produced a much bigger load; but she sucked the entire blast down like a pro. After she was sure she had gotten every drop, she let go of me, licked her lips, and pronounced "That wasn't hard and it was really fun. Did you like it?"

Laying almost comatose on the couch I said "Sis, that was by far the best experience of my life."

She jumped up, clapped her hands, and said "Great. Tom, now I want you to fondle me and eat my pussy. I want to know what it feels like to have a tongue and fingers on my pussy lips and clit, and my nipples massaged and squeezed. Do that for me now, will you?"

At this point all my inhibitions were gone. The only thing in my mind was that I had to do whatever I could to please her so that I could fuck her tonight. I had concluded that her "experimentation" idea was worthy of a Nobel Prize. Bringing myself back to alertness the best I could, I laid her on the floor with her legs open and got to work.

Having eaten only one other pussy before, but considering myself a book knowledge (actually Internet knowledge) expert, I enthusiastically went to work. I first licked her pussy lips up and down, then sucked each into my mouth for a few seconds at a time alternating from one to the other, while at the same time massaging both of her conical turgid breasts with my hands, occasionally lightly twisting a nipple. I don't think she was really ready for the effect it would have on her – up until now she had an almost clinical approach – but she sure knew this was going to be a different experience when I started tonguing her clit.

Her clit was hard to miss. However, since it was longer than any I had seen on the Internet at first I wasn't 100% certain it was the erectile organ of her vulva. But when I put my tongue to it I knew instantly it was since she stuck her fist in her mouth to muffle a scream (so Kate wouldn't awaken) and involuntarily bucked her hips up in the air, causing me to apply even more force to her clit. I tormented her for a good twenty minutes. Being no actual expert I wasn't sure she was having multiple orgasms, but I concluded it couldn't be anything else when on three occasions she went rigid, covered her face with a couch pillow, and started leaking pussy fluid.

Suddenly, I don't know why, I remembered reading about something called a G-spot, and actually seeing a You-Tube instructional video. "Why not try and find it?" I thought, "after all this is The Great Experiment." So I went looking for it with two fingers. Unbelievably, just as related by the video, I found a rough patch about a finger's length into her cunt.

I started a "come here" motion with my fingers, and at first was worried I had done something to hurt Jill since she started writhing around screaming into the pillow and almost convulsing, so I stopped. Virtually out of breath and sweating she lifted the pillow off her face and blurted out

"What are you doing – don't stop – keep going and going."

Now knowing I had found the magical and sometimes elusive area on my first try, I vigorously punished her G-spot with my fingers.

After a good ten more minutes of near convulsions, she finally almost completely stopped moving and panted "Please stop now, I can't take it any more."

I immediately withdrew my fingers and must have had a Cheshire-cat look on my face because she looked at me with her steely gray eyes, smiled the best her weary facial muscles allowed her to, and said "You have every right to be smug. Holy shit was that off the charts amazing," then she held her arms out to me.

I laid on top of her, snuggling her, and we started kissing for the first time. Though her body was wasted and lethargic, her kisses were passionate, more amorous than any in my humble experience at the time. Ten minutes or so of lip-locking seemed to perk her up. She stopped for a moment, penetrated my brain by staring at me with her steely gray eyes, smiled, and said,

"Now we need to fuck!"

MY DREAM COME TRUE.

I convinced her we needed to go to my room to be on a bed, and as far from Kate as we could get. Once we got there, giggling like a little girl waiting to see Santa, she said "Now I know the three main positions are missionary, doggy, and cowgirl. Which do you want to try first?"

FIRST? Holy shit, my virgin penis wasn't sure it could do one, let alone "first." Thinking that doggy looked the most interesting on the web sites I had seen I said "Doggy, but first you need to suck me hard."

With great alacrity she started sucking my dick, and in less than a minute I was hard again. I put her on her hands and knees, knew enough to finger and tongue her cunt for a minute or so before porking her, and then slowly inserted my dick into her pulsating pussy.

Sweet moans burst from her mouth as I continued to bury my tool, until I bottomed out. I then slowly started banging her. To my surprise, every one of my forward thrusts was met by a back thrust from her. We were in perfect sync as we picked up the pace and soon she had an over the top climax and shortly thereafter I blew my wad into her tight vagina. It was clear it was the best experience of both of our short lives, as I lay on top of her back panting while I massaged her tits, and she emitted low guttural sounds as she reached back with one hand and massaged my balls. After about five minutes of this bliss, we collapsed on the bed, and faced each other side-by-side with big shit-eating grins on our faces.

"I had no idea fucking was so emotionally and physically draining," Jill said. "I don't know if I can do missionary or cowgirl right now."

I laughed and said, "Jill you would kill me if we tried. Let's go to sleep and maybe we can try another position tomorrow morning." She gave me a big sloppy kiss, put her head on my shoulder, and in seconds we were both in dreamland.

I got up about 8 Sunday morning. Jill was in the bathroom, and I went to check on Kate. Kate was snoring away. I got back to the bathroom as Jill was exiting looking like Lady Godiva with her glistening vivacious naked body and long blond hair. She smiled broadly at me and gave me a little smooch.

I went to the bathroom and then went back to my bed to find Jill happy as a clam laying on her back with her arms open and her legs far apart exposing her divine fuck hole. As I quickly and joyfully got on top of her I said "Missionary or cowgirl?" She playfully bit me on the nose and said "Missionary."

I got in a 69 position, licked and flicked her clit and pussy lips, and more gently than the day before massaged her G-spot, as she sucked my hog. We were both raring to go in just a few minutes, and I flipped around, penetrated her in one thrust as she squealed, and then started acting like a jack hammer as I banged the shit out her while she wrapped her creamy long thighs around my waist. The relative movement between my rock hard dick and her moist soft cunt was so erotic my mind was flooded with endorphins. I instinctively simultaneously sucked a nipple as I was rhythmically hammering her, while she rubbed her hands over my back and occasionally dug in her nails. We had another almost contemporaneous over-the-top orgasm, and then just lay with our bodies interlocked until finally my totally flaccid penis popped out of her leaking vagina.

We didn't get to experiment with cowgirl that weekend because Kate woke up and our parents got back home about an hour after our joint climax. But we found time to do cowgirl during the week, again with a 69 prelude. Jill was totally magnificent – a veritable rodeo champion. She bounced on me so vigorously I couldn't reciprocate, and just laid back and enjoyed it as she vacuumed every ounce of cum out of me.

While Jill and I always had a great relationship, it was now phenomenal. There is nothing we wouldn't do for each other. Our family members noticed the change, but didn't know why.

I knew that our fucking sessions wouldn't continue because Jill obviously was interested in fucking other guys (the whole reason for the experiment), and I had a number of girls I really wanted to poke. By the time Jill left for college after the next summer she was considered the sex goddess of our high school idolized by every hetero male there, and her fame rubbed off on me. In large part due to Jill's fame, I had no trouble getting laid almost whenever I wanted.

To commemorate our wonderful experimentation, and because no one either of us knew was close to Jill in blowjob ability, or close to me in G-spot activation, every week or so Jill and I would surreptitiously get naked together for an hour. She would give me a blowjob and I would stimulate her G-spot, and we would gently massage each other. We never fucked again - except for a consummate doggy style good-bye fuck two days before she left for college, the highlight of my life.

While I have had more than my share of ass, no other woman up to this point in my life ever held a candle to sister Jill when it came to providing carnal pleasure. I love her dearly.

No one ever found out about the details of our relationship – or so I thought.

I was totally depressed at the start of my senior year after Jill left for college. I was laying in my bed early one Saturday morning with the drapes closed and wondering how I could possibly get past my blues and do something constructive, when the door opened. Kate, now 18, snuck in, and closed the door behind her. She saw the puzzlement on my face, sat down on the bed, put her hand up to the side of my face, and smiled.

"I know you and Jill learned how to make love with each other's help," surprising the shit out of me, "and I need your help now. There are a couple of guys at school that really turn me on, and I want everything to be perfect with them; but I don't have any experience or confidence. You have to help me, please?"

With that, she stood up, removed her robe exposing her sublime naked body with unmatched tits and tiny slit, bush-less except for a reddish hair landing strip. With an expectant smile on her face, she then pulled the sheet off my bed, exposing my quickly rising cock.

Needless to say my depression instantly flew out the window, not to reappear until I had to leave for college myself the next year.

imhapless
imhapless
3,575 Followers
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  • COMMENTS
14 Comments
PEATBOGPEATBOGabout 7 years ago
Lucky B**t**d.

What more could he wish for?

TLMorganTLMorganabout 11 years ago
Kate?

Will he get to nail her? Great story!

GizmorGizmorabout 12 years ago
Practice

Hey Anon. Watch "Survivor" for Reality! Great Fuck Story! Keep us Cumming! Thanks.

AnonymousAnonymousover 12 years ago
Reality not a requirement

I didn't know that reality was a requirement for stories -- if so 99% would have to be deleted. I loved the development of the characters and the sex was great.

mcbtwsmcbtwsover 12 years ago
Reality

Went out the window!!

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