I never thought I would have the set of experiences described here, but it did happen. It all started one evening with a game of Carrom, but I am getting ahead of myself here. So let me first tell you a bit about me. My name is Josh and I live with my mom and sister. I am 21 and I am a college student, 5 feet 10 and 150lb. I do workout at least twice a week to maintain my physique. I didn't have a girl friend at the time and you could say that my experience with girls were limited at the time this happened. If you could believe that! My sister Sara can be called "hot" in every sense of the word. She is quite tall at 5ft 7 with 32-26-34 figure with lovely C cups that she never flaunted whilst out of the house to the disappointment of most of my buddies. She would have made any guy happy with her mischievous and playful nature and to my knowledge she didn't have a steady guy. Her skin was nice and fair with a nice tan she got from mom's genes. Her legs looked awesome and I got a good glimpse of them when she wore shorts or short skirts at home. Her wide hips were inherited from my mom although she fell short by one cup size compared to mom and don't start wondering how I knew that.
She didn't have an awesome butt like Beyonce but in shorts or tight skirts it did look quite nice and the wide hips more than compensated for this. It was tough not to look at her and she never seemed to notice or mind although I didn't know which was which, when she caught my roving eyes. She would just smile and look down or look away as I hurriedly started examining my fingernails with great interest every time she happened to look in my direction at the worst possible moment. Her clothes in the house barely hid her assets and that was my excuse for looking. That is not to say that she was practically naked, but she was quite careless in how she dressed at home. Most of the time she would not wear a bra or would have her legs in a lotus position when sitting and not caring much about what she was displaying. This was not due to her being slutty but it was because of the fact that she liked to dress comfortably at home. As you might be wondering about mom, mom was a splitting image of sis or rather vice versa with a bigger chest which was a D cup. Mom had a slightly rounded belly that I thought was nice for her age of 42.
My sister's friend Kara was as hot at 5 ft 6, with b cups and a slim boyish figure (although what I mean there is that her hips are not as wide as my sister's) that showed off her nice butt which seemed to compensate for her slightly narrow hips. Her legs were slightly muscled from rigorous exercise but it was still feminine enough to get me all worked up. She had a habit of wearing lacy bra's that showed off her hard nipples and they were hard to miss. Needless to say that I have been caught many times staring "pointedly" at those nipples if you pardon the pun. Sometimes, in my wildest fantasies I wanted to think that she liked me looking at them. I guess most girls do like it although this is not a scientifically proven fact.
The trouble, if I may call it that, started when we first got a Carrom board. My sister and I started playing Carrom. Its a board game quite similar to pool but with disks that you have to strike into pockets with a bigger disk. The thing about Carrom is that you have to have the board around 2 feet off the ground. We had to have it a little less than that since we couldn't find a stool higher than that. This meant that we had to bend over to take a shot. I hardly could concentrate during our first game. Sis wore a pair of shorts and t-shirt that showed some cleavage. Every time she bent over to take a shot, I got an eyeful of her delicious cleavage. I was glad that I wore a fairly tight underwear so that it was able to contain my hard-on. At first, she seemed conscious of her cleavage but as the game went on, she forgot about it. That night I went back to my room with a painful cock and ultimately jerked off like crazy to videos of lovely cleavages I managed to search on the Internet. I had to try hard not to use my sister's cleavage as I felt guilty, but honestly, it was quite hard not to remember her creamy breasts.
A few days later she called me for another game. Since we make a racket during the game with our sibling rivalry, mom made us move the board into my sister's room. It was a fairly large room with her bed against the wall and a wall closet. This time it was late when we started. Sis was in her night dress that was slightly large for her and it had a very delicious habit of falling off one shoulder everytime she bent to take a shot. It seemed like a comfy cotton material which had a light color and I could almost see the outlines of her bra cup which was definitely not padded. Her pink bra strap didn't help either by making an appearance as the dress slid off her shoulder. I could sometimes see the outline of her nipples when the flimsy material tightened against her body. After a while, she gave up trying to hold the night dress in place. She had her legs crossed on a chair that could hold at least 2 people.
I was wearing a pair of shorts that were quite comfy and loose and made it a point to wear something under them considering the stress my sister would create for my blood pressure as the game progressed. Secretly I wished her to see up my shorts but I was scared to try anything bold. I did wear a t-shirt that would help me hide any excessive bulges which was a backup plan. A few minutes into the game, something strange happened. I still can't figure out what really happened but it could have been all those silent sexual fantasies that had gripped my mind in the last few days. Anyway, I might have been too excited by a glimpse of Sara's cleavage as she bent to try and distract me from getting ahead of her by pocketing my Carrom men as they are called. I don't think she meant to show me her cleavage but she found out that gazing intently at me or my fingers just before an easy shot did distract me. What she didn't know was that it was partly the cleavage that did it but I would always blame it on her gaze just to get her to do it more! So I was about to take the easiest shot in the world and then my finger slipped and I applied too much force on the striker disk, that sent the Carrom man in the air. There was a squeal from Sara as it obeyed the laws of physics diligently and flew towards her face in a downward arc. She seemed transfixed for what seemed to me like an hour before she started rising up. The disk continued on its trajectory to end up conveniently inside her night dress.
She looked at my face and then down at her body and giggled. "Woah Josh, that was quite a shot! Who is going to find the little guy?" she asked, looking at me mischievously.
I laughed, "I will look away," I said without having any intention of doing so. She started patting her chest and moving lower feeling over her dress, giving me lots of naughty thoughts. She went right upto her crotch, and shook her head puzzled. Finally, she put her legs down and put her hand between her thighs and started looking for it. I was able to catch a few glimpses of her panties as she finally found the lucky Carrom man. Then she smiled at me and said, "Well I seem to have found the man," and moved forward and placed it on the board. I was breathing like I had run a mile very fast or so it seemed to me.
"Next time you do that, I am going to have to ask you to look for it," she said giggling. I tried to look shocked but it was half-hearted. Either she must have assumed that I would never agree to do it or it was surely a challenge. As usual, with her, it was hard to figure out.
"Better not give me challenges. I love challenges."
"I am sure you do. Lets see how it goes," she said, her eyes twinkling. She bent over to take her next shot and I bent over to give the same look that she did to make her lose her aim and obviously to stare down her dress. My feet were planted on the floor as I could never hold the lotus position for a long time. Her next shot got her a point with the Carrom man going into the pocket easily. She squealed and lined up for the next shot. I could see her hand tremble as she tried to ignore my gaze. I cheated. Just as she was about to take the shot, I felt her shoulders tense and I screamed. The shot went wild with too much force being applied and the heavier disk ended up on my lap. In the confusion I managed to slip it under my thigh inside the shorts. Sara was annoyed and giggling at the same time.
"You are so mean! Where's the striker disk?" she asked.
"I don't know, I think it went inside my t-shirt or was it my shorts?" I said, smiling. She rose up, fixing up her dress and walked over to me. Her breasts jiggled invitingly under the dress as she walked over to me. She was so close and lovely. She started running her hands lightly over my t-shirt looking for the disk. I pretended I was ticklish. I was trying to prevent her two hands from searching me and that lead to delicious bodily contact that I was starting to enjoy. When she bent over, I got a glimpse of her lovely breasts encased restlessly inside her bra.
"Close your eyes!" she said.
"Why should I?" I asked.
"I am not exactly dressed for a wrestling match with you. Close your eyes until I find the disk!"
That seemed like an interesting proposal. So I closed my eyes. She put one hand over them anyway, not trusting me and she bent over me touching my upper body. Her fingers were gentle and filled with curiosity as she looked for the disk.
"Where is it?" she asked when she had exhausted the possibilities on my upper body. Each probe was exciting because I was picturing her hands moving closer and closer to the sensitive places on my body. As I had my eyes closed, it was even hotter.
"I guess you will have to try my shorts!"