Sister's Prudish Upbringing

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Nerdy brother is obsessed with virgin sis.
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gulpwolg
gulpwolg
17 Followers

"Hey Paul how come your sister's so fine and you're so ugly?"

I must have heard it a million times through middle school and high school. I was small for my age, the worst at sports, and not very good looking or charming, in other words a geek. The guys worshiped my big sister though; she was, as they would say, a stone cold fox. The teachers liked her too, because she was an excellent student, and never misbehaved. They couldn't understand how I could be her brother either. We were a little over a year apart, so-called Irish twins, but she was two grades ahead because of where our birthdays fell, hers in August, and mine in October.

By the way, I can tell you for certain that nothing sexual happened with anyone before the age of eighteen, because nothing did.

I lived a working class neighborhood in Cleveland with my parents and my aforementioned sister, Gina. As I said, Gina was drop dead gorgeous, perfect in every way. She was about five foot six, dark brown hair, big beautiful light blue eyes, a cute little nose (very rare for us Italians), and full lips. The lips needed no lipstick, and the skin needed no makeup. She had an angelic and innocent face.

She had a body made for evil though, with long shapely legs, and full thighs and hips. Her waist was very narrow, and she had a perfectly round butt that stuck out. I mean really round, like an apple. Her breasts were no more than a handful each, but stuck out nicely from her slight shoulders and narrow waist. To see her standing still was a real treat, but to watch her walk was truly unbelievable, with everything bouncing and swinging. If she was coming or going she was the most arousing thing you would ever see. All the way through high school, everyone considered her the sexiest girl in school, even though she dressed modestly. The contrast between the innocent face and that killer body is what made her special, I think.

It was too bad that all of this was going to waste. You see that Gina was not allowed to date, or have any doings with boys for that matter. Our dad was very old world Italian would not allow it. This was the cause of constant fights and arguments between her and our parents. I think Mom was sympathetic, but the old man wouldn't give in. As long as we lived in his house, we lived by his rules. In his world, if a girl went on a date with a boy without a chaperone, it meant that she had been "had" and was unsuitable for marriage. Even rumors that she had been out would make her "damaged goods." Girls had to be virgins on their wedding night, and there could be no doubt about it.

Men, however, had no such restrictions on them. When I got old enough to get "the talk" from Dad, he didn't say much, but he did say not to "bother" the "good girls". Men have their needs, but stick with the loose women and divorced women until you are ready for marriage. None of this advice or freedom was necessary for me though, because, as I said, I was basically a grade-A geek.

Gina was a very sweet girl, and as good student, always helped her little brother (me) with his homework. She never used any profanity. The worst thing she would say is "dag nap it", or "kiss my feet". She spent a lot of time reading books and doing schoolwork.

Her friends Denise and Diane, who we called Dee and Di didn't date either, not because they were forbidden, but because no one would ask them out. They were very unattractive to say the least, both homely and overweight. Not dating material. She would talk with them on the front porch for hours. I would sometimes sneak around the side of the house and hide in the bushes to listen to them, mostly girlish gossip.

I started hanging out with some nasty boys in the neighborhood, even though I was several years younger than them. Even though I had a hard time making friends and fitting into cliques, but these guys accepted me for some reason. There was Larry and Bryan and a few others. Then there were the guys at the local gas station where I worked part-time who must have been in their twenties. They were not good influences at all. There was a lot of crude talk about sex, which fascinated me. Larry had a ton of dirty magazines. Some Playboys, which only showed titties back then, and some other black and white ones, which showed women with their legs spread, but very poor quality. Larry's parents were never home and the bunch of us hung out in his garage, looked at the pictures, and talked about sex as we smoked cigarettes.

Although I was a geek, and not getting any action, I was a normal young man sexually speaking. Physically, I only got the average six inches, but to me it seemed gigantic. I was really proud of it. I was pretty horny too, above average, you could say. Up to that point, I never thought about my sister in a sexual way, though.

One day I was with Larry and Bryan when my sister Gina came over on her bike. When she left, the two guys started talking about what they wanted to do with her. Bryan said he wanted to run the tip of his cock up and down the crack of her ass. Larry said he would like to have those soft pretty lips wrapped around his crank while she looked up at him with those big innocent eyes, and how he wanted to feel his balls tapping against her chin. This kind of talk was enough to get me hard in those days. It also caused me to start looking at Gina in a non-brotherly way.

When my sister got ready for bed she usually wore a very short nightie with a bra and panties. She would sometimes walk around in these nightclothes before bedtime. I would admire her shapely legs. Sometimes when she sat down, the gown and the panties would hike way up.

I could see all of her thighs and part of her ass. When she stood in front of a light you could see through the fabric, which was almost as good as seeing her in her underwear, which I sometimes would see when she walked between her bedroom and the bath.

Sometimes, she would wear nightclothes which were a lot less revealing. These were shifts, which went down to a little below her knees, and had a fairly high neck. The nice thing about these was that she didn't wear a bra underneath. Her tits stood firm, but would bounce and swing when she moved. I found out that she wasn't wearing any panties either, when one day she changed without closing her door completely. She put the shift on first and then removed everything else from underneath, including her bra and panties. It drove me totally crazy when she didn't put anything on underneath afterwards.

Gina graduated high school when I was finished with my sophomore year. She got a scholarship to Ohio State, but our dad would not let her go away to stay in the dorms, because this would effectively make her some kind of a slut, and destroy her value on the marriage market. He insisted that he trusted her completely, just not the boys.

So Gina attended a small local Catholic all girl college that she could drive to instead, and continued living the life of a nun at home. By my senior year in high school, I was eighteen, with all the hormones that went with it, and a bit of a pervert, I admit.

Nasty as I had become, my sister was still every bit as innocent as she looked. She would hear dirty jokes at school and not "get" them. She would sometimes ask me to explain them if she didn't realize it was sexual in nature. One joke involved 'getting hard' or "being hard" and she didn't know what that meant. When I told her that it meant that a man's private part was hard she said, "Why would it be hard?" I told her to go ask Mom.

The thought popped into my head of showing her my hard-on, which I already told you I was very proud of. It would have to be some kind of accident, of course. I now had the fantasy of her staring at my huge erection with wonderment. This thought was very exciting to me, because I knew she had never seen one before. She had seen me naked when I was little of course, but not since I had grown.

The images of what those nasty boys were saying they would like to do to Gina would play over and over in my head, along with fantasies of her admiring my stiff cock.

"You know your sister has a really nice pussy." Bryan would often say.

"We never heard that before," I replied sarcastically one day. "And how you would know anyway?"

"I can tell," he insisted.

I never told Gina any of this of course and this bothered me, for some reason. One time I told her that Bryan and Larry thought she was fine and wanted to make out with her.

"They can kiss my feet," she said.

On the weekends I would stay in bed later than anyone in the house, spanking the monkey, as you might have guessed, and Gina would be the one to come up and wake me up for breakfast. This was a good way for the "accident" to happen, I thought.

One lucky Saturday, we needed to wake up by seven to go visit our aunt in the hospital. I just happened to wake up a few minutes early with a serious morning hard-on, the kind that won't go away until you piss.

As I was admiring it in the mirror, I heard my mom say "go wake up your brother."

I quickly adjusted the door, leaving it slightly ajar and got back into bed in my planned pose, with my loose jockey shorts pulled to the side revealing my balls and stiff cock. I pretended to be asleep. Sure enough I heard Gina come down the hall and this time I heard the door swing open. (I wish I could have had my eyes open to see her face). I then heard the door quietly close a bit later. By the amount of time that passed between the door opening and the door closing, I knew she got a really good look.

A minute later I heard the familiar knock on the door.

"OK, I'm up." I shouted.

I snuck down the hall to listen to what was going on in the kitchen I heard my Mom say, "He probably had an erection; men often wake up with an erection, that's how their bodies work."

Then I heard Gina say, "It was huge".

Then my Mom laughed and said, "We're all surprised at how big they are when we first see one that way. "I don't think there is anything wrong with your brother; he's just gotten to be a man now. You should be careful to knock from now on."

I was shocked that she told Mom what she saw (that was not part of my plan) , and was afraid that

I would get in trouble, but neither of them said anything to me about it.

I lustfully replayed the whole thing over and over in my mind, picturing my sister looking at my cock, and hearing her say "It was huge."

My eyes were always on Gina after her bath and before bed, as she would walk around in her nightgown, watching the jiggling of her boobs. I loved it when it would get stuck in the crack of her butt. Gina's hips were just wide enough so that you knew she was a girl, but her butt stuck out pretty far behind her, and she had a nice deep crack. Her nightgown would get stuck in it, when she bent over. When that happened, it was even more fun to watch her walk.

Those shifts I told you about had no sleeves, and large armholes. I could occasionally glimpse her tit, and sometimes a nipple, through these holes if she was positioned just right. Like everything on Gina, here titties were absolutely perfect. Her nipples weren't as big as the ones in the magazines, only about the size of a nickel, but were a nice dark pink, almost brown, and the center part stuck out really far, like the end of your little finger.

What I wanted most though, was to see her pussy. I knew it would be perfect like every other part of her, and I had never seen one before. I tried to peek under the bathroom door when she was taking a bath and no one else was around, trying to use a toy periscope that I had as a kid. It was still in the basement after all those years. It was too big, so I took the mirror out of it and would slide it under the door. The first thing I would see was her pretty little feet. As I moved the mirror further under the door, I would be able to see further and further up her legs, but only up to a point. I didn't see much, but was a tremendous turn on to see her clothes fall to the floor and then see her shapely bare legs stepping out of them. Depending on how far she was from the door, I could sometimes see most of her thighs. That may not sound like a big deal, but it was to me. It's funny how sometimes the things you don't see turn you on more than those that you do see.

She would always play Abby Road by the Beatles on her cassette player when she was in the bath. I could smell the fragrance of her bath oil under the door as I heard her splashing in the tub. Soon the fragrance of the oil was enough to drive me crazy. I could still smell it on her body when she came out of the bathroom. I'll never forget that smell. Even hearing that album gives me a hard-on to this day. One evening my luck was right and she went to the furthest part of the bathroom and put one leg up on the tub to clip her nails. You see, the further she got from me, the higher up I could see with the mirror.

As I adjusted the mirror more and more of her beautiful legs became visible. I remember trembling as a huge thick pelt of black hair came into view. I was struck by how big that patch of hair was. That's when I first realized why they called it a beaver. Beneath the hair, I saw a short slit, on her puffy vulva; I was expecting it to be much longer. Everything was pushed up inside there. It looked like it was pouting. "Why doesn't anyone fuck me?" it seemed to say. As my sister moved, I could see the supple flesh stretch and relax, causing the hair of her muff to move. I saw the slit changing length and even open and close a little. It was more wonderful than I ever thought. I could vividly imagine sinking my cock into one of those things.

When she finished, she turned, and I saw her from the front. Her triangle was huge, dark and thick, but with very straight edges, like it was drawn with a ruler. Not a single hair was outside the lines of that perfect triangle. That triangle, and that big beaver, was the only parts of Gina that seemed too big. Way too big, totally out of proportion. I was shocked at how much hair she had, because she had none on the rest of her body. In my mind, that thick crop of black hair meant Gina's pussy was ripe and ready for fucking, despite her innocent looks and behavior. From that day forward every time I looked at my sister, I thought of that ample black crop of hair between her legs. She needed a dick, I thought. She needed it bad.

I was now fantasizing about fucking my sexy sister. I crossed a line there. I let myself get turned on by her many times, but always imagined someone else when I was jerking off. Now at least in my mind, I was fucking my sister. Maybe I should never have crossed that line, but I did.

The fact that my parents were keeping her unspoiled made me want to spoil her all the more. Well, maybe not to spoil her completely, but only to have a little fun. You see, I had actually bought into that virginity business, for her, anyway. But, then again, this is exactly what made the fantasy of fucking her so hot, and difficult to resist. The forbidden nature of it raised my level of lust to a point that I had never experienced before.

Well, fantasies are harmless. That's what everyone says, anyway.

The next time we were at Larry's talking about girls, he mentioned seeing Gina and how fine she was. "Face it, she makes all the other girls look like men," he lamented.

"I told her that you all liked her, and wanted to make out with her," I said. "She said you guys could kiss her feet," I added.

Larry replied "I'll kiss her pretty little feet. I'll suck each one of her toes, just before I lick out her pussy."

Larry had a point about her feet. As I said, Gina's feet were really nice, with perfect toes that were always polished. The soles looked as soft as a baby's. They were very kissable, small and cute, like a little girl's.

"She is definitely beautiful, but I'll bet that pussy still smells like fish," "someone said.

"Just like your Mom's," someone else retorted. Everyone laughed.

"Nope, when a woman is that fine, even their shit doesn't stink," Larry argued. "I'd even push my tongue up her cute little puckered asshole. It would taste as sweet as candy. You sure are lucky having that sweet piece of ass living at your house, Paul."

"That's his sister, shithead" replied Bryan.

"I don't give a damn, if my sister looked like that I'd fuck her till she walked bow legged," replied Larry.

"Incest is best," laughed Bryan.

"Put your sister to the test!" someone added.

They asked if I ever saw her naked or in her underwear, and I told them about her being naked under her nightgowns.

Everyone started howling like wolves.

"She would be so easy to fuck!" said Larry incredulously.

Bryan added reflexively, "she has a really nice pussy."

On my way home I kept thinking about what Larry had said. I contemplated that slit beneath my sister's dark mound and what it would be like to lick it, after doing her feet first. I wondered if she would enjoy it. How wonderful it would be, to pleasure her like that, I thought.

After I crossed that line, and thought about actually having sex with my sister, it wasn't long before I was thinking of nothing else.

I hope that I didn't bore you with all of this, but I needed to explain how I got to be so horny for my sister. As I said before, I think I had bad influences, and I didn't want you to think it was my fault. Well, at least not all my fault, anyway. Besides, they were only harmless fantasies, right?

The problem with harmless fantasies, you might say, is that you soon start thinking about how to make them become reality. Well, in my case, I was totally clueless about how to make something happen. Sometimes, you need something to happen by chance. A lucky accident, if you will. The next thing that I will tell you about was just such an occurrence.

One weekend I was working in the yard, and I got pretty wet and muddy in the process.

When my Mom saw me she said "You're filthy, don't come through the house like that, take those muddy clothes off in the garage. I'll leave you an old towel in there. Put the towel on and go straight for the shower, and don't forget to wipe your feet."

I did like I was told, and was stark naked in the garage, and Gina suddenly opens the door and walks in, surprising me completely. She looked right down at my crotch. She starred at it lot longer than she needed to. It seemed like forever before she looked away and said "Oops, Sorry! "

"Don't you knock? " I said angrily as I put the towel on. It was cold in the garage, and my pecker was shriveled up and practically inside of my body. It looked like an acorn in a bird's nest. I was so humiliated.

"No, I don't normally knock before going into the garage," she said.

Feeling even more humiliated, I stormed past her and went into the bathroom and slammed the door. After my shower I got dressed and went to my room.

Gina came in and apologized. "I'm sorry; I didn't know you were in there. I didn't even realize you were naked at first", she said. "I've seen you in your underwear before, but I never remember seeing a pair like that," she chuckled.

I had to laugh. "It's OK," I said. "No charge for the free show."

A look of relief came over her face. Then something occurred to her.

"The show was better last time," she said teasingly.

"What do you mean?" I said.

"I think you know. Your bedroom door was never open like that before."

"I don't know what you're talking about," I said.

She stared suspiciously into my eyes, as if to see if I was lying. Being a good liar, I acted dumb.

"That Saturday when we went to visit Aunt Maria in the hospital, I came over to wake you up and the door was open, so I walked in. It was all swollen up and sticking out of your shorts. It was huge."

gulpwolg
gulpwolg
17 Followers