It all started when I was twenty years old and my little sister was 18. We came from a very strict family. My father was a bank executive and my mother worked as a trust attorney for a major firm in our town. We were taught that our grades at school came first and everything else came second. Our nights and weekends were spent studying or doing work around the house, and our only times away from home involved going to dinner or to the movies with our parents. We were also only allowed to wear certain types of clothes—I was forced to wear a suit or a pair of khakis, pressed shirt and tie and jacket. My sister was always in some sort of dress, but never anything too revealing. She wore long sleeved blouses with high collars and sensible shoes or skirts cut below the knee with pantyhose and a sensible top, and her figure was always hidden by her somewhat Victorian-era look. From time-to-time, and with the usual protests from my mother, she would get away with wearing a tight fitting sweater and I could just make out the dent of her nipples through the gauzy material. As she became older, the dent in her sweaters began to bloom into full-grown breasts that she was forced to hide with very tight braziers so that nothing would show through.
We were not allowed to play sports, and our only extracurricular activities were involvement in various academic teams at school. My family was also very strict about what types of reading materials were in the house. It would have done me no good to try to hide a Playboy or Penthouse magazine, because my mom was a real snoop and would have certainly found any magazine that I would have stashed away and there would have been Hell to pay. I spent my pubescent years masturbating to the women in Marie Claire and Good Housekeeping magazines, along with the occasional pictures from advertisement card fillers that were supplements for pantyhose packaging. I wasn't allowed to date until I left for college, and to my knowledge, my little sister had never dated. Despite the fact that we were both straight A students and were both conscientious about the way we presented ourselves in public, we were mostly home bound throughout our teen years, and relied on each other for company. My biggest thrill each week was going to church just to hang out with girls who wore clothes that revealed the accentuating curves of their bodies and their long legs clad in sheer silk stockings.
However, I did have one other masturbatory fantasy that I used quite frequently, and that was my little sister. Ever since she was very young, my sister had been a blossoming beauty who, despite her long dresses and plain hair she was forced to wear had always caught my attention. I had always daydreamed about what was under her clothes. She had long, straight auburn hair, dark deep set eyes and small, pouty lips that looked gorgeous without lipstick. As I mentioned, as she grew into her late teens she began developing quite a large bosom and I would daydream about what was under her blouse. While doing the laundry, I would often come across her cotton panties in the dirty clothes basket. Being young and curious, I would often sniff the crotch of her panties and smell the sweet aroma from the nectar of her virgin pussy.
After I went to college, I began to feel some of the freedom of what it was like to be with and touch a girl for the firs time. I still kept up my conservative look, and was forced to attend an in-town college so that I could live at home, but as I began to experiment a little with girls, my masturbating became more frequent and my illusions of my little sister became more frequent and even more nasty. I would picture us together in bed as I slowly rubbed her large breasts and licked her nipples as my hand ran up her smooth thighs to that secret honey pot that was off limits to everyone. As I continued to masturbate on a daily basis like many sex-crazed young boys/men do, I decided to drill a small hole in the wall of my and my sister's adjoining closets. The hole gave a small range of view to sis's bedroom and I would peep through the hole when I knew she was dressing or undressing. I would catch a glimpse of her legs or her ass in cotton panties, and sometimes a rare glimpse of her burgeoning breasts. Needles to say, this would bring on a quick masturbatory session in the bathroom that might end up causing 5-6 ejaculations before I was satiated.
While my parents were at work, my sister and I were left at home all day by ourselves. We would clean the house, wash the dishes, do the laundry, cook and generally take care of everything. It was pretty mundane until one day I caught my sister lying in the back yard in a skimpy pink bikini. She must have borrowed it from one of her friends. I remember looking through the back window at her luscious tits practically bounding from her bikini top, the rise and fall of her tan flat belly and the smooth roundness of her pussy mound in the nylon bikini and masturbating as I watched and fantasized about her until I thought I would drop dead from exhaustion. Wearing a bikini was definitely a no-no in our strict family, but I wasn't about to let anyone find out what a taboo my sister was breaking. I had too good a view and too much fun stroking away at my cock to worry too much about any rules my little sis was breaking. I would pound away until I was raw. Sometimes my ball sac became so drained that all I could produce was a small dribble like pre-cum as my body shook with orgasmic delight. I didn't know how big I was in the cock department since I had never seen many other cocks of my friends at school. But one of my girlfriends in college had admired my length and circumference and had made me very proud of the way my cock looked. I got hold of my mom's tailoring tape one day and measured nine inches from pubic bone to tip and five inches in girth.
I watched my sister most of the summer without saying a word to her about what she was doing. Then, one day, I looked out the window and saw her remove her bikini top. Her tits were round and firm, not dripping with sweat and oil and, free of constraint bigger than I had imagined. Her nipples were erect and as long as the first knuckle of my pinky finger and stiff in the light breeze. They were definitely more than a mouthful, and the pink nipples standing erect that just begged to be licked and sucked had me drooling and stroking at a furious rate. I almost blew my load right then and there without even with the slightest touch to my cock. It was then that I decided to make my move. You see, although we were brother and sister and were from a very strict background, we had always had a special bond toward one another, and I think she knew that she could tease me when she was at a very early age. I would become aroused around her, and although I had a very rudimentary knowledge of sex, I knew what was where and what was supposed to be done with a woman. Masturbating to the thought of my sister's tight, little body had become a daily fascination with me. I didn't know how she felt, but sometimes she would rub up against my legs or my butt or run her hand through my hair playfully. This would cause me to spend an inordinate amount of time in the bathroom with the door locked as I masturbated to her sly little teases.
When my little sister came in from her tanning session, she was wrapped in a large terry cloth towel, and as usual, tried to sneak in through the back door without anyone seeing her. I stood at the entrance to her bedroom, and when she walked around the corner, I quickly grabbed the towel that was covering her body and saw up close the wonderfully gorgeous woman she would turn out to be. With a squeal of fright, she fought me for the towel, but I held it away from her flailing grasps. I chuckled to her and asked her what she had been up to. She was almost on the verge of tears, but said that she was tired of wearing frumpy clothes and not being able to look like her teen friends and was wanting to have a tan when she went back to high school after break. Even though I knew that she would be in some deep shit with my parents if they ever found out, I, being a compassionate big brother, agreed that she should try to look her best, and that her secret was safe with me.
She reached up to me and gave me a huge hug of relief. I could feel her breast rubbing against my chest, and my cock stood at attention at once. I know she could feel my bulge through her tight nylon bikini bottom, but she held me fast for a very long time. When we pulled away, my erection was bulging like a tree limb against my pants.
I asked my little sister if there were any other secrets she had, and she told me that she did, but was embarrassed to talk to me about them. However, after much taunting and, to admit it, a bit of begging, she told me one thing that she had always wanted to do. And even though she was very hesitant to tell me at first, she finally looked down sheepishly and admitted that she had always wanted to dress up in some lingerie or a short skirt or shorts so that she could look in the mirror to see what she would look like. She wanted to look more like her friends or even like a grown up woman. She thought that if she could see herself dressed like a sexy female, she would be less shy and more likely to have a boyfriend or not hear her peers at school making fun of her wardrobe. While she told me this, a tear slid down her left cheek and I wiped it away with the ball of my thumb. I knew she had been taking quite a bit of heat from people at school about the way she had to dress, and I did feel sorry for her. However, I didn't think she would have to look frumpy and meek all the time. If I could play my cards right, she could look any way she wanted while she was at home, and I would be there to help her out. Of course I had ulterior motives, but I didn't let her know that I was thinking perverted thoughts the whole time.
I knew we didn't have any short skirts or shorts in the house, but I also knew that my mother kept a stash of silky lingerie hidden in the back of her closet. I was sort of a peeper and a snoop as a kid (must have taken after my mother), and still am, I guess, and had gone through my mother and father's room on many occasions. I had even found a small dildo that my mother had stashed in a chest of drawers underneath a pile of yarn and sewing supplies. I guess you could say that although my parents were religiously strict, they too had a kinky side that they hid from view. I didn't need anymore encouragement, and told my little sister to lie on her bed and that I would be back in a minute.
I quickly made my way to my mother and father's closet and scrounged around until I found a perfect outfit: a purple lace bra and panties with garters and hose to accentuate the apparel. My mother is a small woman, and I didn't think the fit would be too large for my sister. I was about to leave with my bounty, when I spotted a pair of black sling back stiletto heels that my mother never wore. She and my father must have been playing some games of their own, because I knew that these items were something that would never be appreciated outside the home in public.
I almost ran back to my sister's bedroom, and when I did, I found her sitting on the edge of her bed with her legs tucked up so that her chin was resting on her knees. I could see the slight V of her pussy stretching the cloth of her bikini bottom. She looked at me, then at the garments in my hand, and smiled a little as she realized what was about to happen. I knew that she was nervous, but I was just as nervous as she was at the thought of her body encased in silk lingerie.
