Oversimplification of Amy Ch. 01

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What do I do about my girlfriend's bratty little sister?
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Part 1 of the 5 part series

Updated 06/07/2023
Created 10/18/2015
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Michael142
Michael142
546 Followers

Janie's little sister Amy was a pestering little brat and drove us crazy while we dated, but is she now driving me crazy in another way? What am I going to do about Amy?

*****

Part One, Back then:

Janie was the prettiest girl in our high school. At eighteen, she had blond hair like pure spun gold, and the clearest blue eyes you'd ever seen! She was popular and attracted a lot of male attention, but she was sweet and gentle. Her tall and slender frame fit mine perfectly at five foot eight. That meant that in three-inch heels she was nearly my height.

Many of the athletes and rich boys at school were interested in her, but I am the one she selected. We dated, attended parties together, and she was my prom date twice. As far as I was concerned a sweeter, and more gorgeous creature did not exist on this earth!

Then there was Amy! Amy was a brat! She is skinny and small, and she has light brown hair and dark brown eyes. Okay, she was also rather cute, by way of saying that she was pretty and sported budding breasts the size of plums. She had a rather attractive petite form with slender and shapely legs. She was also Janie's little sister, and at sixteen she was temperamental; there was always a storm brewing in those little brown eyes of hers.

Amy was actually attractive to boys, but she didn't seem much interested in them. Amy's main preoccupation seemed to be making my life miserable when I was with Janie. She was always around whenever I visited her older sister. Lovely Janie seemed to be more patient with "bratzilla" than I was, and would make excuses for her. Amy hated me, but I could never divine a reason why.

Janie could have any boy she wanted but for right now, I was her choice. Was I dating over my head? I thought so even back then, but the prettiest girl was giving me her full attention and I was not questioning my good fortune. My name is Mike and my friends call me that, but I so liked the way Janie made 'Michael' sound musical, that I adopted that as my preferred appellation.

God, how my heart would beat out of my chest whenever I was close to her. I loved the sight and the smell of her ... the feeling of her soft slender arms around my neck as she tiptoed up to kiss me. She had a way of walking that could only be described in poetry ... I am not a poet, but you get the idea!

Yup! I had it bad. She had me wrapped around her little finger and she knew it. We had fun, and shared many common interests; she loved old movies and classical music as much as I did, and we went on long bicycle rides. Holding her in my arms was the most wonderful things in the world. If the word love made any sense to us as teenagers back then, perhaps I was in love with her ... or ... at least in love with the idea of her.

I was a virgin back then, although I was not sure about Janie. I assumed that she was also, and I wanted to be the one to change that for her if she was. As close as we were, and as much groping as we did, I never got close enough to find out. Especially with a bratty little sister interrupting us when we were able to find some amount of privacy.

For example, one night we retreated to the basement rec room to cuddle and fondle on the couch watching a movie or listening to music. There also was little Amy, up top rolling a coffee can half-filled with marbles down the stairs. The reason of course was just to be an annoying little shit!

"Oh! Did I interrupt something?" She would say coyly with lots of giggles.

"Amy, if I catch you, you are going over my knee!" I started to get up, threatening to chase her, and she quickly mounted the stairs trailing rivulets of girlish giggles behind her.

"You wouldn't dare, 'Michael'!" she turned at the top of the stairs, had her hands on her shapely little hips and spit my name back at me as if it was an insult.

"Michael just leave her, she'll go away. Come back, I'm getting cold!" Janie's soft sweet voice could get me to do anything!

After Amy stuck out her tongue at me, I returned to my sweet girl and spooned up behind her lithe form. As I resumed my position, Janie turned around inside my embrace so we could kiss. She has the sweetest lips, and I managed to slide a hand up her blouse and onto one of her firm breasts when I heard,

"Ew! Kissing! Janie look he has his hand on your boob! I'm going to tell Mom!" It was Amy leaning over the back of the couch watching us ... taunting us.

I was up and vaulted the couch in a flash, and as Amy started to retreat up the stairs squealing for her Mother. I grabbed her little arm, and pulled her over my knee sitting on a straight chair by the bottom of the stairs.

"No! Michael! Stop! You can't do this, I'm ... I'm ... just a little girl. I'll tell Mom!" Amy's pleas fell on deaf ears. She kicked and squirmed, so I held her arms tightly behind her back as I started to paddle her behind. They were not hard blows at all, but just firm enough for me to make my point with her and no more. I gave her only five swats, but she screamed as if I was murdering her.

I noticed what a pretty, shapely little butt this brat had on her as I paddled her, and I was surprised at feeling a little twinge as my hand make contact with her body. I pushed her off my lap onto the floor, and as she rose rubbing her butt, she spit out at her sister,

"Janie I'm telling Mom! You boyfriend beat me and you are both going to be in big trouble!"

Janie, against her normal calm nature fumed, and with her teeth clenched replied to her bratty kid sister,

"If you do, I'll tell Mom what a brat you are being when I have company over, and she'll give you worse that Michael did ... and with her hairbrush on your bratty little bottom!!"

Amy's brown eyes burned as she yelled back at her older sister, "Brat!"

"Brat!" Janie counter-punched just as quickly.

Sisters, right? Janie and Amy had a typical sister-sister relationship, sniping at each other at times, and just being sisters at all other times. With our renewed attentions to each other, and calming my girl down a little, I was able to get my hand inside Janie's panties, and I fondled her sensitive little 'button' to a nice little shudder as we kissed, and groped each other.

Janie and I dated for nearly a further two years, before she went east to a large university, leaving me at at the local college. I started in pre-law and was doing quite well. I dated some and attended parties, and even got laid out of a couple of them! As I was starting my junior year at the college, I happen see a very pretty, but familiar face on the quad.

"Hi Amy, how's your butt?" I said to my former bratty little tormentor as she approached.

"Michael! I was afraid that I might run into you here. I got a letter from Janie, and she has a new boyfriend. He is tall and handsome, and rich, so I guess she will have no further use for the likes of you!"

"Still a little sweetheart, aren't you?"

"Not that you will ever find out ... Michael!" My name is seven letters long, but she always makes it sound like a 'four-letter' cuss word!

She turned on her heels and disappeared into the crowded walkway. It did not escape my notice that Amy had filled out quite nicely in the past two years, and had become quite a beautiful girl, but beautiful poison as far as I was concerned!

I was dating a couple of girls at that time, but nothing serious ... just companionship, sex, and fun. At the various dances, and mixers at the college I did see Amy, but it seemed that she was always with different boy. Either she was very particular, or they found her hard to get along with. My money was on the latter explanation. I steered clear of her as much as possible but damn, she looked so good all dressed up!

At the latest mixer, I was with Kathy Miller and noticed Amy from the other side of the dance floor. She was with some geeky little guy that I thought was beneath her notice, as attractive as she had become. I grabbed Kathy for a slow dance, and we tried to move to an area away from adult chaperons, so we could dance a little closer and kiss a little. At one point moving backward, I bumped into another couple. I turned to see Amy looking into my eyes. She was just about to say 'excuse me,' when she recognized me in the darkened dance floor. Before she could react, I said,

"Oh, sorry Amy, hope I didn't hurt you little ... butt!" It was then that I realized that she would have smiled at me, but her expression dropped as she said to her partner,

"Ugh! Let's get out of her Henry!"

As I watched her walk away, I felt embarrassed and ashamed at being so mean. I couldn't let a little girl smile at me? I felt like a jerk! But, as cute as she was, little Amy was nowhere on my radar.

"C'mon baby, let's dance." Kathy said, pulling me back into our close embrace. She did not say anything about what she witnessed, but Kathy likely just filed it away.

Kathy is pretty. She has soft silky brown hair and dark brown eyes. She has a couple extra pounds, but it looks good on her, she is very shapely. As I looked back into her eyes, I thought, just for a split-second that they had the same dark hue as Amy's brown eyes.

"What are you looking at Michael?" Kathy brought me back to reality.

"Uh, uh, nuthin sweetie, let's dance."

I slid my hands down to her hips and then around her back as she put hers on my chest with her cheek resting between them. She felt so good in my arms. Her hair smelled wonderful ... sweet ... perfumed. I breathed in her aroma as we danced slowly ... very slowly!

I like Kathy for her genuine sweetness, and her great sense of humor. I like her voluptuous body, so different from some of the skinnier and bitchier girls I have dated. I can't say that I am in love, but more 'in like' with Kathy. We were, for all intents and purposes, boyfriend and girlfriend but with no agreement on exclusivity. After the dance Kathy and I returned to my car, and as we started off, she said,

"Michael, can we go to ... you know where?" This was her way of asking me to drive her to Pine Crest ridge, a local shady make-out spot. I gave her a broad smile in response.

She cuddled up to my right arm in the car, resting her hand lightly on my thigh. We could have just gone back to my apartment for more privacy, but this is more romantic and its more exciting fooling around in public ... well, semi-public.

We moved into the back seat when we parked at our destination, and we were in a tight clench very quickly. By the time we settled in the back seat, she already had her sweater unbuttoned, with her lacy bra, in view. Kathy has the loveliest breasts: large, round and cottony-soft to the touch. As we made out, I fondled and kissed those magnificent orbs, sucking and pinching her nipples.

She is not a slut, and I never treat her like one, but she is very generous with sharing her delightful physical charms. Unfortunately, there are parts that are still off limits ... at least for now. As I reached up under her skirt, hoping to liberate her from her panties, she would pull my hand out, and said reluctantly,

"No, Michael. I want to, but we have only dated a for few weeks ... I would feel more comfortable waiting a little ... please be patient honey... we'll get there." Her pretty eyes searched my face and she continued,

"You-you're not mad are you Michael?"

I gently cradled her face in both my hands, looked into her sparkling brown eyes, and kissed her full on the lips,

"Of course not honey. I won't rush you into anything."

"Y-You will call me again won't you Michael?" She looked worried. I kissed her and said,

"Pick you up next Friday night, seven o'clock, the movies. Okay?" I said with a smile.

She let out her held-in breath, and beaming with a wide smile, she said,

"Yes, Michael. It's more than okay!"

She took my hand and placed it on her naked breast, and we spent the next two hours doing just about everything else but fucking. Ah, what the hell; I liked Kathy and could wait for her. She allowed me to fondle anything I wanted to, but stopped short of oral sex and actual intercourse.

We stopped at our favorite café afterward for a coke and a burger. Kathy is fun to be with, and we had a great time talking and laughing. She is an 'A' student, also in pre-law, and is smart enough to make one hell of a lawyer someday.

For now, she is my girlfriend and although the word love does not come up, I really enjoy being with this lovely and smart girl. We continued to date through our junior year, and toward the end of it, she did let me fuck her.

It was wonderful, and her body was incredible. Finally being able to slide inside her soft luxurious body was an amazing turn-on, as she pushed her ass up against my thrusts. The first time we did it, we came simultaneously. We made love often after that, and I have to say ... I just never tired of fucking that girl!

As I entered my American history class as a senior, I smelled a familiar aroma as a pretty girl sat in the seat just behind and to the right of me. I turned slowly to see Amy sitting in my class. She didn't notice my at first, but then she did. She just gave me a wry half-smile, and returned her attention to the class syllabus we all retrieved from the table as we entered.

A senior and a sophomore taking the same course is odd since it is a lower level course, but I could not fit it in earlier, and still needed it. I found out that Amy was smart. She always had her hand up and not only had the right answer, but her responses were intelligent and well thought out. After that first class with her, I hurried out of the classroom without looking back because I knew that Kathy was waiting for me in the hallway. We both had a break in our schedule, and were going to breakfast. She embraced me sweetly and we were kissing when I felt a little jolt. Kathy looked up and asked,

"Did that little girl just bump into you?"

I looked to see Amy quickly padding down the hall as her short crisp pleated skirt swished attractively. My eyes followed her as she walked away until Kathy turned my face toward hers with her hand and asked,

"Hey, remember me darling?" then her eyes searched mine with her brow wrinkled a little, "Do you know that girl Michael? She looks like that one from the dance that time."

"Yeah, she is the little sister of a girl I dated in high school ... she hates me!"

"Oh!" Kathy said brightly, giving me a smile that said she wanted to know more.

"She is a brat, and I got so sick of her act one time that I turned her over my knee and spanked her. She has hated me ever since ... she's just a kid!"

"Well Michael, you were not looking at her just now, like you thought she was a kid!"

I smiled at her softly, looked into her incredible brown eyes and said, "Have I told you yet how beautiful you look today?"

She stifled a giggle with her fingers, and said, "Nice save, Michael ... and no, you haven't! Tell me!" She wrapped both arms around one of mine and as we walked away, she pressed me, "Tell me Michael, tell me, TELL ME!"

We walked down the hall laughing, giggling, and joking back and forth, both very happy being together. I had a wonderful time as usual with her at the café, and I loved listening to her talk. My mind did wander a little, returning to the sight of that little pleated skirt retreating down the hallway, and shapely ass of the little brat wearing it.

Kathy was right ... I no longer saw Amy as a kid. Hell! Doesn't make any difference since she detests me so much, and I am so happy with Kathy ... for now. After classes a month later, I got a phone call from Janie.

"Hi Michael! Taking a little break from school, and thought I would give an old friend a call. How about lunch today? My treat!"

"Janie! It's great to hear your voice! Yeah, lunch is good. Meet you at um, that place we went that time ... noon."

"Okay Michael, see you there!"

Janie looked great! She seemed more mature, and dressed in expensive clothes. We talked mostly about her schooling out east, and her career goals. She wants to be a corporate CEO by the time she's thirty, and talked about getting her MBA right after college. We talked back and forth for an hour and a half as we ate and drank. During a lull, she asked,

"So, how is Amy? I understand you two have a class together."

"Amy? Why should I know anything about Amy?" I asked, not understand the question.

"Well, I just thought that you two might have had lunch together or ... something."

"Amy hates me ... you know that! She would sooner spit in my eye as talk to me!"

"Michael! You mean to tell me that you never noticed when we were together, that Amy had a crush on you?"

"What do you mean? She was a pestering little brat. She is your sister, but why would you think that she crushed on me."

"Michael, haven't you ever heard of Hamlet? Shakespeare? 'The lady protests too much, methinks'? It means that sometimes a girl might resort to inappropriate or, say, bratty behavior to attract the attention of someone she really likes."

"Sorry, I guess I was sick that day in English literature! Do you remember when I got pissed at her, and spanked her in front of you? All the times she threw things at me, that little girl had it in for me!"

"That's not what she told me Michael. We talked about it afterward in my room. Her panties were a little moist after you laid hands on her little teeny-butt. Later, she told me that she was embarrassed and mad at the time, but that she tried to be bratty enough for you to do it to her again."

Janie lowered her eyes and smiled at me and continued, "I have to say Michael, I was a little jealous of Amy for her admiration of you, but we didn't stay together, so no big deal."

"Well, that's a real mind-blower Janie! She slammed into me in the hallway after a class one day, and just continued on without saying anything ... my girlfriend noticed."

"Don't you see, Michael? That was classic attention-getting behavior. Amy likes you."

"Are you saying that I should call her up and ask her out? She'd tell me to go to hell."

"Yes, under that scenario, I believe she might, but that doesn't mean she wouldn't try to find a way to say yes sometime."

"Janie, this is Amy we are talking about. Remember her? That skinny little sixteen-year-old that drove us crazy on dates?"

"Michael, she is not sixteen anymore ... she is almost nineteen, and has become quite a looker."

"Well, the point is moot, since I have a girlfriend I like." I said hoping to settle the question.

"I didn't hearhe word love in that sentence anywhere, Michael!" I took Janie's hand in mine and said,

"Janie honey, you were my fantasy girl in high school and as thrilled as I was to be with you, I guess we never really loved each other either."

Janie smiled in agreement with me and just said, "Okay Michael ... just saying!"

We continued with our lunch with a lively discussion, and then I looked at my watch, remembering an appointment, and walked Janie back to her car, giving her a hug and a brotherly kiss on the cheek.

On the way home, I just could not get my mind around what Janie told me about Amy. I never for an instant thought about Amy in any romantic way, since she was so young when I dated Janie. "She's just an f'ing kid!" I told myself, and in truth, I still saw her as a kid.

I called Kathy when I got home and made a date for supper that night. Kathy and I have no secrets (at least not from my end), and we did discuss my lunch with Janie. Kathy is not jealous of Janie since she understands that I never had real feelings for my ex-girlfriend. At one point Kathy did ask,

Michael142
Michael142
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