tagFirst TimeWith My Sister's Help

With My Sister's Help

byJumpinjetta©

"So Mark, Kelly's looking pretty cute today, isn't she?" my sister Debbie asked, standing in the doorway.

I looked up from the couch at her, all dressed in her marching band outfit, looking at me with a sly grin.

"Yea she's cute Debbie . . . " I replied, turning back to the television.

"Well, we're gonna go out on the porch and look for deer. Later why don't you come upstairs and I'll make you a sundae ok?"

"Sure" I said.

"Great! And you know what? Tomorrow Kelly and I are gonna have to stop by her house before the game, cause she forgot her bloomers!" I looked over to my sister again. "Actually, I took them out of her bag before we left! You know, just playing a prank on her!" Debbie gave me a quick wink and dashed out of the room.

I sat ther wondering what a peculiar comment that was. But I had to admit, that last comment put a new light on what happened that past hour.

I got home a few hours ago, taking a weekend off from my sophomore year in college. My parents were away for the weekend for the wedding of their oldest friends daughter in the mountains. I wasn't surprised to find my only sister Debbie and her best friend Kelly in the kitchen when I walked in, as much time as they spend together. Apparently Kelly was over for the night, and the two of them were going together to our high school's game the next day. Debbie played the trombone in the marching band and Kelly was a cheerleader.

Although they had been best friends since middle school, they really couldn't be more different. Debbie was one of the most outgoing people I knew, and even though, at 18 she was two years younger than I, there were plenty of times she seemed like an older sister to me, looking out for me and giving me advice. She had way more experience dating, never having a steady boyfriend, but seeming to go out with someone new almost every week.

Kelly on the other hand, was as introverted as Debbie was outgoing. It was only after years of Debbie's prodding that Kelly finally tried out for the cheerleading squad, and even though Debbie thought Kelly would now go to all the school parties with her, Kelly still preferred to stay at home most nights. As different as they were, they were always close, and I knew now as seniors, they were even looking into the same colleges.

For some years Debbie has been trying to set me up with Kelly, always gushing about how sweet and pretty she was, claiming she had a crush on me and that Kelly deserved a "nice guy" like her "awesome older brother".

And although I had to admit, she was turning into a real cutie, and I always thought she was a sweet girl, I knew the main motivation for Debbie's attempted matchmaking was her dislike for my girlfriend Julie.

We'd been dating for over three years now, and from the first time they were introduced, they didn't get along. I always attributed this rift to their being so much alike, but Debbie always denied this, giving her the nickname "Rich Bitch", and assuring me all Julie cared about was money and popularity.

Debbie didn't hide her displeasure when Julie went to the west coast for college and I stayed on the east. She was sure that marked the end of our relationship. But to her chagrin, our relationship is still going and consequently, Debbie's dislike seems to keep growing.

I think her anger towards Julie hit a peak this summer when I told her Julie confessed to a "one night stand" with a guy at college, but apologized and promised it would never happen again. Although Debbie had always been my confidant, I immediately regretted sharing this with her, and had to endure a renewed effort to convince me to break up with Julie.

Even last week when I called to let her know I'd be coming home for the weekend, she grilled me about Julie, asking why she never comes home when I'm there, and assuring me she was "misbehaving" at school. It really got to the point where I felt I had to stick up for Julie, no matter what the situation, just to offset Debbie's immense dislike.

So all this ran through my head as I though of Debbie's last comments: "She forgot her bloomers"?

Soon after I got home Debbie called me out of my room and asked me to take a picture of the two of them in their uniforms. Debbie had changed into her Marching Band uniform and Kelly into her cheerleading outfit. I took a few pictures of the two friends and went back to my room to watch TV.

And now Debbie made a point of letting me know that Kelly's bloomers were still at her house. So that meant what? Kelly was just wearing panties under that short yellow skirt?

I had to admit that made me think for a second.

Kelly did have a really nice little body, although her small frame did tend to make her look a bit younger than the 18 years that she was. And I remember the first time I went to a football game and watched her cheer, noticing her cute little butt as her skirt flew up during the cheering moves. And although she never seemed to have that confidence and grace the other cheerleaders had, there were times I did wonder what would happen if I took my sister's advice and took Kelly out on a date.

So now, what was my sister up to? I grabbed my digital camera and quickly scrolled through the pictures I had taken of them, now looking with a bit more interest in the cute cheerleader.

She did look pretty cute, her dirty blond hair pulled into a pony tail, tied with a ribbon. Large brown eyes. Sexy legs. . .

I had to shift in my seat, starting to feel a bit aroused. I looked more closely at her face. She did seem to have a strange, almost embarrassed look to her. Although she was a shy girl by nature, there seemed something more. And now that I thought about it, Debbie had been trying to get her to jump around while I was taking pictures, telling her to do some "kicks and splits". And I remember the dirty looks Kelly gave her.

Out the partially open window I hear the porch door open and heard the two friends go outside.

"You can see them best from that far corner, over there" I heard Debbie say, and with those words it dawned on me. I knew what Debbie was up to.

To understand, you need to know a bit about the layout of our house, and what happened when Debbie and I were kids.

The den (where I was sitting) is actually in the basement. But because our house slopes downward in the back, there is a small window high on the wall in the den, overlooking the backyard. If you sit against the wall, looking straight up through the window you can see the edge of the wooden porch which comes off the kitchen. Specifically the far corner.

It was years ago when my parents had some sort of a dinner party and Debbie and I were hiding out in the den that our aunt Darcy was standing on the porch, in that far corner. I remember watching some stupid cartoon when Debbie tugged on my shoulder and with a look of disgust on her face pointed up and out the window.

We had a perfect "underneath" view of Aunt Darcy, her skirt hanging off her quite obese rear end, and saw her hot pink panties surrounded by mounds of droopy flesh hanging from her legs.

We had a giggle fit, and spent the next hour gazing up at the guests, ease dropping on the conversations with the window slightly open.

Years later when we'd be out together and we saw an obese woman wearing a skirt we considered too short, Debbie and I would race to beat the other in proclaiming "I'd hate to see her in the corner!"

So now it was clear! My sister had schemed to place her friend in a position where I would have a perfect view up her little cheerleading skirt! And took away her bloomers as well, letting her big brother check out her friend's panties!

I was a little pissed at first. Who did she think she was, trying to manipulate me (let alone Kelly) like that. Did she think it was that easy to get me to break up with Julie?

"Oh look! There's a doe with two little ones", I heard Kelly say. Our backyard was adjacent to the woods, and there were always deer coming and going.

"Cool! Here Kelly, have some more wine." Debbie said, perhaps a bit louder than usual, and I wondered if she was making sure that I heard.

I couldn't believe it, was she trying to get her drunk too?

"Maybe just a little more. It's so nice out here."

I sat staring at the TV, my mind racing. Perhaps I could take a look. Just to see what color panties she had on. Slowly I moved to the end of the couch and looked up and out the window.

And it was a nice sight I saw. From my vantage point I could see Kelly standing at the corner of the porch above, looking across the field. I looked up her legs, her panties seemingly just out of view.

A breeze must have blown across the porch behind her and her yellow skirt blew up just a bit in front, and I got a full view of the front of her enticing powder blue panties contrasting against the smooth white of her thighs.

I had to force myself to blink, hoping for another fortuitous breeze to show me again what I had seen. Instinctively I looked to my camera. Do I dare take pictures? There was something so sexy about those panties, something about that blue instead of the matching yellow bloomers that normally go with her uniform.

But no. This was all Debbie's plan wasn't it? And as much as I had to admit she was succeeding, was I reduced to peeping on my younger sister's friend, hiding in the basement? And as I adjusted my now prominent erection, I thought back to that famous scene in "Fast Times at Ridgemont High", when Judge Reinhold is caught masturbating while spying on his sister's friend. No, I'll just continue watching TV . .. .

Over the next half our or so, I tried to keep focused on the show I was watching, but couldn't resist peeking out the window a few more times, sometimes catching a glimpse, sometimes just listening to the friends talk, perhaps laughing a bit more frequently as they continued drinking the wine.

"Kelly, you wanna go inside and watch a movie or something? We'll get some ice cream and maybe pop popcorn." I scooted over for one more look before they went inside, but could not see her anymore.

"Sure, just let me change first. .. "

"No!" Debbie interrupted, "Let's keep our uniforms on! Anyway, you look a whole lot cuter in your cheerleading outfit than I do in my band uniform."

"Fine. I guess . .." Kelly's last remark was cut off as the door closed, the girls now back in the kitchen.

Once again I sat there, wondering what was going on. Did Debbie have more schemes planned? I once again tried to immerse myself in the television program.

. . . . . . . . . .

"Mark?" Debbie peeked her head in the door. "Your sundae is served! We're in the living room." And before I could say anything, she ducked out.

So not sure what to expect, I got up, and headed upstairs.

I turned the corner to the living room and stopped in the entranceway. On the coffee table in front of the couch was a carton of ice cream and all of the ingredients needed for an ice cream sundae. And on the floor in front of the table, Debbie and Kelly were lying on their stomachs watching the TV in front of them, each with a bowl of ice cream.

Of course my eyes went straight between Kelly's legs at the triangle of blue panties showing under the back hem of her skirt, her legs slightly parted. I could feel my erection swell again, and wondered how long I could just stand there, staring at that beautiful sight.

"Mark." Debbie called, her head turned back, noticing me standing there. Kelly glanced back and immediately pushed herself into a seated position, smoothing the skirt under her.

"Hey. . " I said lamely, walking around to sit on the couch. "Looks good" I dug into the carton of ice cream, trying to look busy.

"Kelly, why'd you get up?" Debbie actually looked annoyed looking at her friend.

"Just more comfortable . .." Kelly's face was flushed, and I wondered how much was from the wine.

We finished eating like that, me on the couch, Kelly sitting on the floor and Debbie lying down, watching some stupid comedy show.

"Hey bro, can you give me that back massage you used to give me, you know when I hurt my back that time?"

"Sure." I hesitantly walked around the table and knelt down by her left side, opposite to Kelly. Leaning over, I dug both of my thumbs into her lower back on either side of her spine and worked them up and down. A couple of years ago Debbie went to a chiropractor after hurting her back and after her treatments ended she trained me to perform his recommended massage techniques.

"Oh, that really is nice" she sighed. "Can you get the hips too?"

I scooted down, kneeling next to her thigh and moved my hands down to the sides of her hips, massaging inward just under the points of her pelvis. Debbie gave an exaggerated moan. "This is sooo relaxing. . . ."

I noticed Kelly glancing down at her friend and started feeling really awkward eliciting such sounds from my sister, with my hands practically massaging her butt.

After several minutes Debbie suddenly got up. "That was awesome!" I sat back, and it seemed that both Kelly and I were just waiting to see what Debbie would do next. "Can you do me one more favor Mark? Please, please, please?"

"Uh, sure." I said hesitantly.

"Sweet!" Debbie quickly knelt down next to Kelly and all but forced her back to her stomach. "Give Kelly one of those massages too!" Suddenly on her stomach again, Kelly looked up at Debbie with a mix of surprise and perhaps fear.

"I don't need . . ." Kelly began, but was quickly cut off.

"Oh come on Mark! You said you would!"

After a brief hesitation, I replied. "Ok, sure. .. " I shifted over, kneeling next to Kelly.

"Here!" Debbie exclaimed and placed a pillow under Kelly's head so she could rest on it, her head turned to the side.

Now with Kelly turned away from me I looked over her extremely enticing body. But with my sister still right next to us, I reached over and stared massaging her back. Once again I could feel the beginnings of an erection as I pressed my thumbs into her flesh.

"Doesn't that feel good Kelly?" She asked.

"Yea. . " came the muffled reply with a slight shake of her head.

I had to admit I was really starting to enjoy this. I continued massaging her back for a few minutes.

"Now the hips." Debbie said. I hoped the bulge in my pants wasn't too visible to my sister as I took a step back on my knees and placed my hand on Kelly's hips. "Here", Debbie scolded, putting her hands on mine and pressing in and up on Kelly's sides. I could feel Kelly's body stiffen under my hands.

With this motion her skirt slid up a few inches over her bottom, now exposing a small view of her blue cotton panties, disappearing between her tightly closed thighs.

I knew my sister was watching me, but couldn't keep my eyes off her partially exposed bottom. Slowly as I continued massaging I felt Kelly's body relax, but started to notice how much her breathing seemed to be increasing.

"Isn't that nice Kelly" She asked again.

"Mmmmm" was the only reply.

"Mark, why don't you rub a little lighter, on top . . . "

As if in a trance I obeyed my sister, moving my hands over Kelly's cute skirt covered butt, not yet daring to rub below the hem. My erection was now starting to throb and I had to resist the urge to press against Kelly's thigh.

My massages were getting lighter and lighter as I circled each of her butt cheeks, and finally let my palms slide off her skirt and slide over the juncture where her buttocks joined her thighs, delighting in the feel of her bare skin and the texture of her panties. My eyes were riveted on her panties, disappearing between her thighs. I so badly wanted to slide my hand down the blue fabric, part her thighs. . .

"Here Kelly, let me take off your shoes" Debbie knelt down at Kelly's feet and removed her sneakers, and as she pulled on each foot, she pulled each leg outward, opening Kelly's legs and giving me a view through her upper thighs to her panty covered crotch on the carpet.

As my hands traveled all over her bottom, now fully under her skirt, I heard Debbie get up. "I'll put all the dishes away. I'll be back in a bit. . ." She left the room.

My right hand slid down the back of Kelly's right thigh, crossed to her other leg and started sliding slowly up the inside of her left. I stopped just before touching the fabric of her panties, feeling the heat of her body, watching her cute butt flex, pulling her panties ever so slightly between her cheeks. I waited just like that, my hand so close to her most private area, until her body started to relax again.

I Turned my hand and with my middle finger, gently stroked upwards on the center of her panties, tracing the crease of her lips beneath the thin cotton material.

At first contact I heard a sharp intake of breath and saw her lift her incredible behind slightly upwards. I looked up at Kelly. Her head was still facing to the right away from me, her body stiffened once again. I looked down, seeing my hand disappeared between her spread legs, under her beautiful panty covered butt.

I started gently moving my fingers up and down, lightly rubbing her lips through the thin material, delighting in the way her body was now reacting, grinding tentatively into my hand, her buttocks clenching and releasing with each movement.

I located the little nub of her clitoris and started focusing my attention there as her hips started pushing more and more strongly against my fingers. And when she turned her head towards me, her eyes closed, her mouth opened with a quiet moan, I had to press my left hand in my lap, my excitement now almost too much to bear.

"Mmmm, mmm, mmm, mmm . .." Kelly started almost humming to the rhythm of my fingers, her panties becoming damp with her wetness.

As her body sped in its gyrations, her butt lifting and falling, grinding into my hand as it clenched and unclenched with each moan, Kelly partially opened her eyes and looked up at me. It was the most erotic sight I had ever seen.

She reached down and took my left hand from my lap, bringing the palm to press against her cheek.

Suddenly she closed her eyes and her body stiffened, driving my one hand underneath her into the ground, pressing my other hand tightly against her open mouth.

"Uhhhhhhh, ooooooooo!" She cried out, a powerful orgasm shaking her body.

I sat there for a moment, listening to Kelly's rapid breathing as her body seemed to melt, her eyes still closed, my left hand still clutched to her cheek, my right hand trapped in the damp warmth of her groin.

And just as I was wondering how to take care of my almost urgent needs, Debbie was there again. And to my amazement, she knelt next to Kelly, and with a hand on her hip, puller her over so that she was now lying on her back.

"Kelly", she scolded standing back up. "Your panties are a mess! I'll have to throw them in the wash!" She shook her head and looked at me. " Mark, can you give me her panties?"

I looked down at the beautiful girl lying there, her little skirt pushed up, only partially covering her now dampened blue cotton panties. But Kelly just looked up at me, her eyes half closed, still recovering from her recent orgasm.

So I reached up under her skirt and slowly pulled her panties down, over her hips and down to her knees. I stopped momentarily, looking at the light pubic hair just above the still moist pink folds of her vagina. Pulling her panties off fully, her knees fell once again to the sides, displaying her fully to my lustful eyes. I simply held the panties behind me for Debbie to take as I lowered my head between her spread legs and gently touched my tongue to her.

Kelly's hands went right to the back of my head as she spread her legs wider, and began moaning once again. I slid my tongue up and down, exploring every crease, my senses overwhelmed by the taste the musky smell. I found her clitoris once again, and greedily sucked and nibbled all the while being rewarded by Kelly's moans of pleasure, her hands forcing my head forcefully against her.

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byJumpinjetta© 10 comments/ 211014 views/ 22 favorites

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