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Older woman/teen Stories

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older woman/teen
john456berry

Babysitting For A MILF, How A Young Lad Learns So Many Lessons, And Answers To His Questions

The story of a young lad who babysits for a MILF, She gives him so much more than he ever hoped for.

Maggie arrived home just a little after ten thirty, the earliest since I had been babysitting. She went through her usual checks before returning to the lounge. I was still sitting on the sofa when she spoke. “You said you don’t have a girlfriend?” “No.” I went to say more, but Maggie raised one hand. “And your sister has not told you anything about me?” “No.” I left it at that. “Can you keep a secret as well as your sist...

Tmac1957

The Paperboy: Epilogue -- Moving On To Hotter Times

Teens forced to find new outlets for sexual release and end up in each others arms

A few weeks after the lusty age-gap four-some. I was shocked to see that both the Johnson's house and the Crawford's house next door were for sale. I knocked on the doors as I delivered papers, and no one answered; odd since I knew my MILF lover and her mother were nearly always home. The day the moving vans arrived, my friend Steve and I sat in my car across the street and watched, hoping to see Mrs. Johnson or her mom,...

john456berry

Babysitting For A MILF, How A Young Lad Becomes Obsessed And Perhaps Teased A Little

The story of a young lad who babysits for a MILF, He becomes obsessed and it appears she has noticed his feelings

Mrs. Green lived at the end of our road with her two kids, a girl of about 8 and a boy of about 10. I think I remember there was a Mr. Green too, a long time ago. My older sister would babysit for Mrs. Green twice a week while she went out, midweek and Saturday evenings. Three months ago, my sister was going to a friend’s party on Saturday and asked Mrs. Green if I could stand in for her. I was sixteen and a half, a quiet...

Tmac1957

The Paperboy Chapter 6: Wet dreams Do Cum True

Mom and Daughter continue a lovefest with teen-age boys

After a short rest on the cum soaked carpeting, Mrs. Crawford suggested we move the party to the bedroom, "for a proper fucking," as she put it. I watched in awe as this grandmother, Jerry, with short-cropped hair and luscious G-cup breasts walked naked across the room and down the hall, her tight wide ass a lovely sight to behold. My adolescent playmate Steve followed quickly and I helped Candi, Mrs. Crawford's hot thirt...

Tmac1957

The Paperboy Chapter 5: A Mother, Daughter Tryst

Paperboy Collects More than Cash Visiting Customers Who Have Playtime on Their Minds

The paper route customers returned from their vacation about a week after the late-night pool party. I made sure there was no evidence of our little orgy so the Johnsons and the Crawfords continued to think of me as a responsible teenager they could trust to keep an eye out on their ritzy homes while they were gone. When it was collection time for the paper -- I went door to door to my 100 customers each month to collect...

EmmaMoon

Playing With My Babysitter

My babysitter introduces me to sex toys and anal play.

Dressed in only a sheer pink babydoll that barely covers my buttcheeks with no panties underneath, I walk barefoot downstairs and into the kitchen, where my babysitter, Mrs. Jones, is slicing up fruit for breakfast. Her hips sway in a seductive rhythm as she hums a soft melody. My mother's silken robe clings to her supple figure like a second skin, accentuating every curve. I can't help but notice how she's pinned her red...

ezzguy

How Mrs. D. Took Her Neighbor From Dud To Stud

A young widow finds the sexual release she needs in her young neighbor.

When I was a high school senior I was a skinny, shy kid. Although I didn't have a problem talking and communicating with my guy friends, I clammed up when talking to the girls. As you can guess, it was frustrating when my friends started hitting on and dating the girls. I felt like a fish out of water. In my high school years, my body changed big time. I have always loved football and decided to play in high school. My co...