My Little Sister's Girlfriend
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa, Mult, Teenagers, Consensual, BiSexual, Heterosexual, Fiction, Incest, Brother, Sister, Group Sex, First, Oral Sex, Anal Sex, Masturbation, Squirting, Lactation, Water Sports, Cream Pie, Voyeurism, Doctor/Nurse, Teacher/Student, Public Sex,
Desc: Erotica Sex Story: Chapter 1 - A guy with six sisters learns a lot about women faster than most other guys. Now he needs to study up on older women as well.
I was the only boy in a family with seven children.
As luck would have it I was the oldest sibling in the litter and had to put up with their teasing and silly ways making life at home seem almost like being in a girl's sorority in a female college. I was reluctant to enter into carnal relations of a serious nature with any of my sisters because the complications were too stressful to even contemplate. A couple of my sisters were what I would consider to be "Hot" including the youngest one called Princess by my doting parents.
My name is Bill.
Not a particularly exciting name but it suited me just the same.
My sister called Princess was just turned seventeen when she walked into my bedroom with her study partner Tiffany. I was understandably upset because all I was wearing was my boxer shorts and my plaid socks that were comfortable but looked so childish that I was immediately embarrassed that Tiffany saw me wearing them on top of the bed.
"Hi, Billy, Tiff and I were hoping you would drive us to the movie over on Powell. It is the new scary Halloween one where all the girls get locked into the deserted hospital on Halloween night."
The two silly things went into those baffling fits of giggling that girls do when they are excited inside and don't quite know how to express their emotions.
I hoped that Tiffany didn't see my semi-hard erection flopping left and right inside my revealing boxers. I wasn't really jerking off or anything but just simply watching the video of the Japanese Gymnastic team. It was all those tiny girls all bent over and doing stretch exercises that got me all hot and bothered just before this irritating pair walked in my door.
Tiffany was looking super sweet in solid black leggings that disappeared up under her tiny pleated skirt with the black and white cubes that drew attention to her crotch and petite little backside. She was a bit older than my sister and had just recently celebrated her eighteenth birthday. Tiff lived downstairs in her parent's apartment on the first floor. I hadn't seen much of Tiffany since the two of us got stuck inside the big empty carton in the back of the parked semi-truck in the garage across the street but I remember how we both had hidden silently with her sweating body folded underneath mine as we hid from the other team. I was a bit old for the kid's game but when you don't have many choices of others to play with, you tend to settle. Anyway I remember the girl called Tiffany squirming underneath me and me whispering in her ear to keep quiet and not to move so they wouldn't discover our hiding place. She settled down at long last, but I noticed her heart was beating awfully fast like she had just been running a race around the block. That was a while back and she was a lot more grown up now and we wouldn't be playing any kid's games any longer.
My sister was pretending to vamp me out with her sensuous movements like she was enticing me to follow her commands. It was so cheesy that it was downright pathetic but I agreed to drive them because I was sort of glad to get a chance to meet Tiffany again under different circumstances. It was amazing to me that she didn't wear the slightest hint of make-up and yet managed to look more appealing than any of the girls with their war-paint on at the local dance hall.
The three of us squeezed into the front seat because my backseat was so crowded with all my school junk that it would have taken us an hour just to clear a space. I saw Tiffany looking back there with an amused look on her pretty face and I was a bit mortified that she had caught me with a semi in my boxers and then saw how messed up my car was like I was some sort of loser.
Tiffany was in the middle of the bench seat and my sister just spread her legs out wide and forced the poor girl to almost plaster her body against my bare thigh. I was still wearing my running shorts from school with my regular trousers getting cleaned down on the corner. I have to tell you that the leggings rubbing my hip and thigh felt like a hot iron on my leg and I could swear I could feel the movement of her muscles under the skin every time she made the slightest movement. I swear that I could actually smell her delicate female scent with the peppermint suckers in her mouth and the body odor from her armpit that was almost sitting right under my nose. I was not in the least turned off. In fact, I inhaled deeply because it was so arousing to my libido that I instantly formed a distinctive erection right there on the front seat with the two young girls sitting beside me.
I didn't care if my silly sister Princess saw my hard-on because she was such an imp she would just giggle and make fun of it. I was hoping that Tiffany would not see it because she was a real lady and it would be a disaster if she thought I was some sort of pervert or something even worse.
Of course, my sister spotted it and pointed it out to Tiffany hoping she would be able to embarrass me before we even got to the movie.
It was real strange that the perfect little lady Tiffany sort of turned away from me and grabbed hold of my sister's hands to tell her some crazy story about a boy in school who had been caught whacking off right in the science lab. Her skirt rode up real high and the soft spot of her "tween" started to rub my erection like it belonged right on top of my hardness. I came this close to shooting my load right as I was driving past a cop car with a pair of uniforms thankfully looking the other way and not seeing how distracted I was driving on Main Street.
Tiff bounced on my groin a few times letting me know she was loving my thing digging in deep between her leggings hoping to find an entrance to the good stuff. We both knew that was unlikely but it made for interesting speculation anyway. My sister Princess had no idea what fun we were having just out of her sight. I was certain the little moans Tiffany tried to hide were a dead giveaway of the internal stirrings her closest friend was experiencing only inches from my sister's face. I saw the little imp trying to look over Tiff's shoulder to see what was going on but the clever girl had such a grip on her hands that all she could so was rub her chin on the other girl's boob. I thought it was funny but kept it to myself because I had other things on my mind.
Fortunately, I was able to keep my spunk contained and when my sister told me she would pay my way into the movie as a pay-back for driving them to the show, I accepted because I figured I could find a way to sit between them and maybe get a little finger action with Tiffany's leggings.
I decided to go with them and chance the embarrassment of my girlfriend seeing me with the two conspirators inside a darkened picture show.
Of course, we sat in the balcony because we were certainly old enough and in this neighborhood nobody would suspect one of the little teasers was my ball-busting sister and the other her closest friend. It looked like I was the sort of guy that needed a minimum of two teenaged females to keep him satisfied watching a movie about screaming girls running from monsters.
I did see my old English teacher Mrs. Stern sitting in a row in front of us and she turned around looking closely at me trying to determine if it was that same Gallagher boy that was such a bother in her classroom. I tried my best to make myself invisible between Tiffany and Princess and they wondered why I was suddenly so quiet.
The lights went down low and I focused on the back of Mrs. Stern's head thinking about how I used to fantasize about guiding her pretty face between my legs by holding her ears real tight and forcing her to open her lips to take me inside all the way to the hilt. In my fantasy, she never once gagged or showed the least bit of reluctance no matter how hard or how nasty I make her take it. Just thinking about that now gave me a huge erection that caught the attention once again of my kinky sister. She saw me fooling around with my hand in Tiffany's lap and assumed it was the touch of her friend's pretty pussy that was making me all agitated. I have to admit I was pushing the fabric of Tiffany's spandex leggings inside the damp folds of her camel-toe with sneaky furtive motions.
Princess was happy the lights were down low now because she could open me up and pull out my equipment whilst I was distracted with Tiffany's happy hole. I whispered to Tiff to lean forward and when she complied, I slid my other hand inside the back of her leggings and was able to wiggle my middle finger into her heated crack and find her brown eye waiting to be pushed open.
Now I had one hand in the lovely Tiffany's bum and the other buried in the folds of her labia learning her vaginal geography just in case I needed to find my way in the dark.
My silly sister was stroking me with her milkmaid hands under the cover of the darkened movie house lights and I could make out the profile of Mrs. Stern's head looking over her shoulder at me using both girls in a nasty macho way that made them both objects of my degraded desires. I was ashamed that my sister was involved but I felt it was really all her fault for being so downright aggressive. Since I had no other choice, I grabbed hold of my sister's hair and pulled her face down into my lap to absorb my spunk when it came time for me to sprinkle it freely in Tiffany's direction.
The little Princess managed to swallow it all down with a skillful flair that impressed me beyond my wildest expectation. At the same time, the horny perfect lady Tiffany sprayed my fingers with her female juices letting me know that even perfect ladies liked to have an orgasm every now and then as well.
The two girls were soft and calm now hanging onto my arms like I was their boyfriend out on a date and in all honesty I was not entirely opposed to that.
When the lights came back on at the end of the show, Mrs. Stern stood up and I could see her perfect heart-shaped mature woman buttocks just as ripe and ready as I had pictured them back in the classroom. I knew she had divorced her husband who was fooling around with an intern at work and I simply could not understand how any male could have turned away from that delectable treat in favor of some untrained teenage girl with no talent at humping.
She smiled at me and I knew she had recognized me even though I was certain I looked vastly different than five years ago. I figured she was probably in her late twenties now but her boobs were still perky and her cheeks were not drooping in the least little bit. Not that that would have bothered me because I kind of liked that comfortable change in a female's shape. I pretended to go to the men's room but I followed Mrs. Stern to the lobby while my two companions waited for the next show to begin.
The older woman was bending over to close the top of her boot and I could not resist banging into her bottom like it was an unavoidable accident. The feel of her soft package filled my groin with a promise of paradise and she looked up seeing it was her former student. I was certain she suspected that I had a "thing" for her but was hesitant to do anything about it.
"I thought it was you, William. You are so adventurous to have not one but two girls with you at the picture show."
She made me laugh but I wasn't about to tell her one of them was my naughty sister Princess because she would have a bad opinion of me fooling around with one of my sisters. At least I had the gorgeous Tiffany to show off as a major conquest and I had the scent of her pussy on my fingers to prove it.
"Hello, Mrs. Stern. I am at college now and should graduate in June. Then, I have to face the real world and find a job."
She still had her backside touching my legs and when she looked up into my eyes she smiled and said,
"Well, you are welcome any time over at my house if you want to discuss your future in the business world. I might be able to give you a few pointers to help you over the hump."
The way she said, "Hump" was an unspoken promise but I was certain I was on the right track from the lust in her eyes. I promised to visit as soon as possible and hurried back to the two girls so they wouldn't think I had abandoned them when they both were thinking we had some unfinished business to conclude as soon as the lights went down again.