My Sisters Best Friend
Part One

For as long back as I can remember Cindy hung out with my sister, the truth be told, they were best friends since grammar school. Cindy always treated me like her little brother. She was an only child and her father was the police chief in the small town we lived in. So I believe to compensate for wanting and not having a sibling, she adopted me more or less, as my sister thought I was a pain in the ass, and at times I was.

Cindy had waist length naturally thick curly blond hair (she could look like cousin IT from the Addams family, just by positioning her hair over her head and face); she was six feet tall with long arms and legs. She played volley ball, basketball, soft ball and enjoyed any out of doors sports. She was very attractive, had a sweet and kind heart. When she came over to the house to visit, I was always with her and if I was not, she went and found out why. Many times my sister would have school club meetings at the house. Cindy and Carrie, my sister, were members in many of the same clubs. Cindy would sit on the floor and motion for me to come over to sit with her, I did gladly, as she was always warm and affectionate with me. This time was different, I sat between her legs and she lifted her knees and crossed her legs around me, she pulled me up close to her, and covered us both in her long hair, I loved every minute of it. With her hair strategically covering me and no one could see, she gently leaned me back so my head was between her breasts. Needless to say I was in heaven. She gently rocked me forward and back, I fell asleep. When the meeting ended, she whispered to me and kissed me awake, “wake up sweat heart”. The back of my shirt tail was damp and the back of my pants was also. I learned later, the rocking motion was actually her using me to masturbate with. I was little I did not know this until I was much older. I attended all meetings that were held at the house and every time this was repeated, no one the wiser.

My Sisters Best Friend
Part 2

Cindy and I grew close over time, she was my baby sitter for many years. One such time, my sister had a track meet out of town and my parents asked Cindy if she would stay at the house and be my babysitter for about a week. Cindy was enthusiastic to say the least. The first night, she slept in my brother’s old bedroom (he was over in Vietnam at the time). I could not sleep and I tossed and turned. I got up and went into Cindy’s room, she was awake also. Cindy said,” What’s wrong sweet heart?” I responded I could not sleep. She asked, “Do you want to sleep in here with me, I nodded yes. She lifted the cover sheet, I could see she was naked and I thought,”Wow, what a beautiful body”. She then said,” Only one condition, you have to be naked also”. She said, “Don’t be shy, I have seen you naked dozens of times when I bathed you”. It did not seem so wrong then, to me. She reached over and unbuttoned my PJ’S and they dropped to the floor and I was sporting a boner that would not quit. She commented that I knew how to make a girl feel wanted. She reassured me that I had a beautiful body and there was no shame in us being in the nude. I crawled into bed next to her. She pulled me close to her, my body and my penis were touching her soft skin. The sensations were out of this world. She then started to rub between her legs, I asked her, “Why are you doing this” and she replied, ‘It makes me feel really good”. She then said,” Would you like to learn how to make me feel really good?” I nodded enthusiastically; I thought this is going to be fun. She then spread her legs real wide. She told me to crawl in between and get as close as possible to where her finger was pointing. She said, “Here is your first hand’s on lesson on how to make a girl cum.” Cindy said,” Give me both of your hands, now with your middle finger , gently hold these lips open, as she positioned my hands, on her tight little pussy lips. Cindy praised, “ Good”, “Now with your finger closest to your thumb, gently rub right here”, “Do it very lightly this is very sensitive, it is called a clitoris”, “When you rub it, that will make me very happy and I will squeal with glee. So I gently and lightly,- began to rub her stiff little bud and you know what, it got wet and it got bigger, she was moaning and telling me to keep it up. My hands and arms were wet all the way to the elbow. She even squirted in my face once. She said she wanted to wait a while and maybe do it again. I thought hell, let’s do it again right now. The both of us got up and took a shower together to clean up. I was tall enough that my face was level with her pussy. After we cleaned up, we just stood in the shower looking at each other admiringly. She then said,” Now you know how to make a girl cum.” I leaned forward and planted a kiss on her camel toe, she just smiled at me and said, “You really know how to make a girl feel wanted”. She then said, “I have a few more lesson’s I want to teach you”. We went back to bed and I slept on top of my life teacher’s body, at her insistence,. My dick next to her pussy and my mouth against the side of one of her breasts, the most restful sleep I ever had.

My Sisters Best Friend
Part 3

The next night, I was in bed with her and she said, “I want to repeat what we did last night, but a little differently. Eagerly, I got into position, my face was only inches from her clit, her pussy smelt great, lightly perfumed, I thought Food of the Gods. I began to rub it gently, she started to writhe rhythmically, and then she said to stop. I asked why and she said, “I am going to teach you something new”. Cindy said,” I want you to hold the lips back like I showed you, I want you to get your mouth as close as possible to the rubbing point. I eagerly complied, and she praised it. Now she said, “I want you to use your tongue and lick it like you would ice cream.” So I put my tongue on her clit, it was smooth and salty tasting. It did not taste bad at all. So I licked her and she instructed me to take longer strokes and slower, I eagerly complied. As I made those long strokes, my tongue surveyed every micro inch of that girls pussy. I was like an explorer in a foreign land and enjoying every inch of it. I improvised and gently inserted my tongue into her now moist and very pink pussy. I was really enjoying tongue fucking her and boy did she love it to, this time when she came, I literally took a shower in pussy juice. She begged me to stop, this time I did not comply and four more showers came my way. I really enjoyed her coming it was a blast. She smiled at me and said,” I have more lessons for you, are you eager to learn. I nodded exuberantly. We again got up for our ritual shower, which was fun in itself. We went back to bed and slept the night away in each other arms.
The next night she taught me how to finger fuck a girl, in my case I used my whole little hand. She instructed me to move my hand in and out, which I did and boy did she scream with glee. Natural blondes do have the prettiest, pinkest pussies hands down or up in my case. The rest of the week we practiced everything she taught me. When my parents and sister came back, my dad asked her “Well, how was my little man.”, she quipped, “ More of a man than when you left him.” My Dad curled up his nose, as if to say, “What the hell did she mean by that?” My dad did not like Cindy or her father, I never understood why.

My Sisters Best Friend
Part 4

Cindy remained my baby sitter until she went to college and even then she came back for breaks from college, she always found time to spend with me, a willing student. Cindy’s father bought her a then brand new 1970 hemi cuda ragtop. It was her High School graduation present and I got to ride shotgun, top down, her hair flowing in the wind, like the mane of a prized Arabian Stallion. Cindy had a distinctive walk, one that commanded respect and awe. I turned twelve years old, the summer before she went to college. She spent a good part of the summer with me. We went swimming, to the museums, parks and movies. I also got lessons on how to fuck with my dick. She took me to this pond that had a waterfall, it was out in the sticks, if you know what I mean. We went skinny dipping, I was in heaven. We got out after some fun and frolic in the water and laid down on this huge blanket. I leaned over and kissed her nipples and licked them and caressed her beautiful, pert, supple breasts. She leaned over to my stiff dick and basically inhaled it. She sucked and stroked it, moving her mouth over my shaft, up and down, she had both hands on the back of my butt cheeks. She felt me tensing up, she shoved my dick further down her throat, I screamed, “I AM GOING TO CUM. “ I did and she swallowed every last drop.
She licked her lips and looked up at me, with another one of her characteristic smiles, and cute quips, “This time” she said, “Let’s go for the pussy.” I fell backwards onto the blanket, my dick was as limp as a sock. I was truly spent, the tank I was sure was empty. She crawled over and started stroking and sucking my dick, as if she was trying to breathe life back into it. The greatest surprise to me was it did spring to action, and Cindy commented,” See your dick does want to play some more.” Cindy grabbed my dick and talked to it as if she was giving a pep talk to a football player. Before I knew it my dick was as hard as a rock, it was so hard it hurt. Cindy climbed up and over me, and inserted my rock hard cock into her moist and willing pink pussy. I could not believe how great it felt and it met with hymenic resistance, and she pushed down hard on my cock. Blood dribbled down the sides of my shaft. She moaned and winced. She then seductively said, “Now neither of us are virgins.” She moved up and down on it, I asked her to take it slow, as I did not want to cum to soon. Cindy took long slow strokes, up and down my dick. The feeling was indescribable and Heaven is all I thought at the time. Before I knew it, I could feel I was going to cum again, this time it was stronger and of greater pressure. I came not once, but three times in a row, cum was bursting from around the seal of my bloodied dick shaft to Cindy’s pussy hole. Cindy stopped and then started again, the pleasure started to well up inside me again, this time another torrent of cum burst forward, literally showering my balls with white cum, she pulled my dick from her bloodied creampie and sucked it some more, the fifth and final torrent of cum burst from my dick into her mouth, she had the look as if she was drowning, she did swallow all but a few drops, she licked her lips with a prideful look and grinned at me, and quipped,” I have some more lessons for you”, I grinned and nodded with great approval.

My Sisters Best Friend
Part 5

The last time I seen Cindy, was when she and my sister graduated from college. I just turned sixteen. Carrie got a job in another state and mom and dad helped Carrie move and settle into her new apartment. Cindy stayed in the guest room at our new house, my parents bought a year earlier, presumably to be my baby sitter and prevent me from throwing a wild party, while the folks are gone. If they only knew, Cindy was my wild party, I fucked every orifice on her that week at least one hundred times. That week I learned how to butt fuck a girl. Cindy gave me more blowjobs and pussy than I ever got as an adult. When my parents came back, they helped Cindy get ready to fly out to a major medical teaching hospital, to complete her internship and residency for her medical degree. I rode with Cindy in her hemi cuda to the airport, I walked with her to the gate, my mom and dad were standing back with her father, I had tears in my eyes, as I said good bye to her. She took me in her arms and gave me a French Kiss. As I write this, I can still taste that kiss in my mouth almost forty years later. She reassured me we would see each other again. I watched as she boarded her plane. My dad looked at me and said,” You were fucking her weren’t you?”. The only second time in my life I ever hit someone, was at that moment, when I knocked my father completely out with one punch, and I did it right in front of a on-duty police officer, Cindy’s father, the police chief. The police chief, asked me if I loved his daughter, I told him “I will always love her for the way she treated me”. Cindy’s dad then handed me an envelope, it had a letter in it and what felt like a set of keys. Cindy wrote me a goodbye letter and in it she gave me full ownership of the ‘cuda, she said she wanted to give me a present every teenage boy wants, his first car. The truth was she gave me a better present than that car, she gave me herself. I still own the ‘cuda to this day and have restored it twice, it is worth over a million dollars, but to me it is priceless, I learned all about girls in it from a wonderful girl.

My Sisters Best Friend
Final Chapter

Fast forward about thirty years, I am lying in a hospital bed and my heart is failing, bad genes are partially to blame. My sister, Carrie is at my bed side, she says that Cindy became a cardio-vascular surgeon and she has called her. Cindy was flying out from Johns-Hopkins. About a day later, a familiar voice, distinctive kiss and a familiar massage of my cock, awakens me, “Wake up, sweet heart”. I am looking at Cindy, still stunning as hell and definitely a dick straightener, I did get a boner, even as weak as I was. We had a long talk about my condition and the fact I needed a heart transplant. I asked if she would head up the transplant team, as I knew of her accomplishments and tracked her career. I could tell she was flattered. I told her that if I died on the table, I would still love her. She reassured me, she would do everything in her power to keep me from dying. A donor heart came in, a motor cycle wreck victim, everything matched up, it was a go. I was whisked to surgery and was on the table for 20 hours. Cindy was my surgeon, they said I died 3 times during that procedure, each time she brought me back, the last time I seen my parents and her father. My dad and I talked out our differences and Cindy’s dad told me to say hello to his pumpkin. I was in ICU for a week and Cindy stayed at my bedside. I woke the fourth day after the surgery, I told her that the last time I died, I seen and talked to her dad, he said to say hello to his pumpkin and tell her he is proud of her. Cindy broke down and even in my weak state, I held and comforted her. She told me only she and her dad knew of her nickname. She asked me about the other side, I told her how peaceful it was, I also confided in her I tried to stay, but God sent me back, he told me to tell you he loves you. I had a long recovery, and Cindy stayed by my side for six months of rehab. She helped and encouraged me every step of the way. Carrie asked me about my relationship with Cindy. I told Carrie it was none of her business. Carrie said she knew that Cindy was fucking her underage brother at the time. I said then I guess, you also know just how much I loved and cared for Cindy. Carrie, said the only reason I liked Cindy was I was getting a piece of ass regularly. At that point I tossed a full bed pan at Carrie and hit the bitch in the head with it, knocked her stupid ignorant shit covered ass out. She also ended up with a lightening bolt scar on her forehead. The floor nurse noted my bad behavior and reported it to my surgeon, Cindy asked me about what happened, I told her Carrie figured us out or was snooping on us. Cindy asked me about the knockout, I told her that Carrie went where angels would not even tread and I was determined to send her to the angels. Cindy and I talked at great length about us in the past. I told Cindy that both of our actions flowered the way I dealt with women in my life and I had her to thank for all those wonderful experiences. I told her that every young boy should have a roll model like Cindy to teach them about girls. My sexual experiences with her were mutually consenting, between two people that loved and respected each other, age was not a consideration. The laws in the United States are archaic at best and detrimental to human psycho-sexual development.

Anonymous readerReport

2016-02-28 14:33:45
I must say.
That escalated quickly

anonymous readerReport

2013-01-22 01:20:05
Great story! I really enjoyed it.

anonymous readerReport

2012-11-02 21:58:10
Wow that's so interesting

anonymous readerReport

2012-02-20 16:26:24
That Was A Good Story!

anonymous readerReport

2011-11-06 14:35:47

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