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The Tomboy's Journey

"Her journey to discover her sexually."

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Author's Notes

"I invited my wife's high school crush over Christmas evening 2020. I told her he was her present."

“She fell for him all over again”

Back in our high school days my wife was a tomboy.  Plain, flat, awkward, no make-up or fancy clothes.  Too tall, her legs too long for the rest of her body...  Not the kind of girl who got any “boy action” in the 1970ʼs.  The one thing she had was basketball.  Being six feet tall and very competitive she became the captain of the girls’ team and her senior year was an “all area” center.  But lonely, no boy action.  No homecoming dances, no proms, no making out with a boy in the backseat of the car at the drive-in movies on a summer Saturday night.  That was reserved for the cheerleaders, the pretty girls.

He was the “All-American Boy.”  Captain of the boys’ basketball team.  Drop dead good looking.  A date with a different cheerleader every weekend.  Girls fell at his feet. They all became his conquests.  He was her crush.  She wanted him and no other.  But she knew, he was way out of her league.  He never gave her the time of day.

I liked tomboys.  I liked her.  Her long legs, her firm small chest, her jet black hair.  Her milk-white skin.  And what did I like the most about her?  She did not have other boys' hand prints all over her breasts.  She would be mine and only mine.  I pursued her.  Watched her games.  Cheered her on.  Talked to her.  Walked her to class.  Carried her books.  We became high school sweethearts. 

After I finished college, we married.  I was the only man who ever saw her naked.  The only man she ever slept with.  That would all change before 2020 came to an end.  We built a good life together.  Great careers, big house in the burbs, money in the bank, wonderful kids.  But there was always something missing. We were more like friends than lovers.  It was him that she always wanted.   He was the only boy who could make her fall apart.  I wondered how she would react if we ever saw him again.  I got my answer at our twenty-five-year high school reunion.

Our high school reunion changed everything.   He was still the most popular guy there.  Still in great shape, still drop dead good looking.  But everything else had changed.  The cheerleaders were fat and wrinkled.  Their football star husbands were fat and bald.  The homecoming queen he took to the dance looked sad and lonely.  It was all so boring until she walked in with me.  The tallest woman there.  The black dress that covered her to her neckline, but was V cut in the back all the way down to the top of her firm nice ass. 

Playing pick-up basketball with the men on our block kept her ass looking good.  Her body was slim from her three workouts a week at the club with a personal trainer.  Her face was soft and relaxed from the yoga class we took together.  It was as if the world stopped when we walked in.  People stood still and looked.  The music seemed to stop.  All eyes were on her as she walked to the bar. The Tomboy who got no boy action in high school had become the most beautiful classmate of them all.

I admit it.  I looked for him.  I wanted to see the look on the face of the guy who thought he was too good for her in high school.  He did not disappoint me.  I loved the look on his stuck-up face.  Eyes bugged out.  Mouth wide open.  He could not take his eyes off the girl he never gave a second look.  As we walked to the bar it was as if the Red Sea parted.  The tomboy who could not get a date was the center of attention all these years later.  He tried to stay away.  He tried to pretend he did not notice her.  But every time he talked to another, his head turned to her.  Her milk-white skin.  Her jet-black hair now peppered with gray.  Her small firm breasts that he never got to touch.  Her long legs that he never looked twice at.  And her ass, the nicest one at the reunion. 

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Oh, how I enjoyed how he looked at me.  The “you are so lucky” look on his still handsome face.  As hard as he tried he could not stay away from us.  He walked over and said hello.  And, my wife fall apart all over again.  She blushed, tripped on her words, hung on his, and even spilled her drink on his pants.  As I watched them talk I could not deny one simple fact.  After all these years, she still was not over him.  She settled for me, but it was him that she wanted.  He knew it too.  I could tell by the sly smile that appeared on his face.  It was the same smile he would get in high school when he told the guys in the locker room which cheerleader he had a date with, and what he planned to do with her in the back seat of his car.

She went to talk to her old girlfriends.  Just me and him now.  He bought me drinks.  Told me how lucky I was to have her.  How dumb he was for never asking her out.  I loved it.  She was mine, not his.  I had the one girl in our class that he did not get naked in the back seat of his car.  Or so I thought.  From across the room, she still could not take her eyes off him.  I knew that look.  She bit her lower lip.  I knew it was still him she wanted.

     She came back and we talked the night away.  She laughed and blushed all night.  Hung on his every word.  Before we knew it was 3 am.   He gave me his card and said “We must stay in touch.”  I said that we would.  

My wife and I went home to our big house in the burbs.  I peeled the little black cocktail dress off of her.  I laid her in our bed and made soft gentle love to her.  Then she did something she had never done.  She put her hands on my shoulders and rolled me to my back.  She jumped on top of me and eased my cock inside her, and then she cowgirl fucked me like a wild woman.  Hips flying, pounding into me again and again.  Her breasts bounced wildly when she was not smashing them all over my face.  

After I came she rubbed her wet dark bush all the way up my chest.   The look on her face, I had never seen such passion in her eyes.  She moved up even higher.  Her knees touched my ears as I felt her cream-covered sex pressed to my mouth.   The all-American girl closed her legs tightly and, face fucked me until she screamed with delight.  It was amazing.  As she fell asleep I lay awake and thought to myself, I make love to my wife, and then she fucked her high school crush.  Our life would never be the same.

   

Published 
Written by MySharona
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