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Babysitter Stories

babysitter

Can You Be Cukolded By a Woman?

Dora's pissed at her husband's fantasies about their sexy babysitter!

Dora answered the door, knowing full well who was on the other side.  TT, also known as Theresa Tammy, her babysitter.  She lived just a few houses down and had become almost a member of the family since the baby was born.  Dora loved her because she was so perfect with the little one, so gentle and caring.  She came by not to babysit but at Dora’s request.  She had no idea why she was here, and knowing how innocent TT wa...

The Former Babysitter

He meets his ex-babysitter and helps her.

It was a spring day bright and sunny but not too warm. Jakob and some of his friends were in town at the street fair drinking beer and enjoying themselves. As the evening slowly approached, fair attendance shifted from families with small children to teenagers showing off in front of each other by buying alcohol whether they were allowed to or not. Jakob saw some of his son's friends trying to buy beer though they were wa...

The Babysitter II: Distraction

After a frustrating failure, he needs a distraction. She knows what he needs.

When I woke up the next morning, I first had to recall where I was and how I had ended up there. The environment seemed familiar, yet unusual. That was until I vaguely remembered I was lying on the living room couch—alone. Drowsy as I was I tossed and turned a bit until my face came to rest on Emily's pillow. Unconsciously, I hugged the pillow and dug my nose into it to catch her smell which set just a few butterflies in...

Halloween Fun Followup

Roxanne was not going to be denied any sinful pleasures. I was in deep trouble.

After a serendipitous hookup with Roxanne on Halloween night, I was quite smitten by our unplanned intimate exchange. Roxanne had babysat for Janice and me on several occasions and while she was very cute, I had never entertained any untoward thoughts about her. Now, after our Halloween hookup, my mind was full of all types of inappropriate thoughts and designs. I didn’t quite expect to fall into an illicit relationship w...

Bailey, Our Baby-Sitter and a Friend

Bailey was the type of teenager you couldn't ignore even if you wanted to . .

Bailey was our very outgoing, vivacious, high energy, family baby-sitter. How I managed to survive after she headed off to her freshman college semester, is beyond me, but somehow, I managed to readjust. I was a little depressed the first several weeks, as Bailey had upended me, unlike anyone else I had ever known. When Bailey texted me that she was looking forward to being back home at the Christmas break, I became a lit...

Bailey, Our Babysitter

Bailey was the type of teenager you couldn't ignore even if you wanted to

Bailey was our very vivacious seventeen-year-old babysitter and from the moment I first laid eyes on her, I knew I wanted to experience a little private one-on-one time with her. Bailey was an elusive catch, but one that was worth pursuing. Our relationship was very casual at first and very businesslike, but the more she took on babysitting duties for Ally and me, the more desirous I became. I loved Ally, but our marriage...

Blackmailing Breanna, Chapter 1

She was caught on hidden camera by a past girlfriend. What will the consequences be?

"Hello, Breanna? This is Mrs. Duncan. Would you be able to babysit for us on Friday night? It's Tom and I's anniversary and he's taking me out for dinner and dancing. It's been a long time since we went dancing and I'm really looking forward to it!" she said. "Sure, Mrs. Duncan, I'd be happy to! Sally and Bobby are great kids and we always have a lot of fun. It sounds like an exciting night for you too! What time do you w...

Straight To Hell

Babysitting was a better job than I expected it to be.

I had known Carter for a few years now.   He worked in the same office as my mother and we had come into contact here and there at work functions. As much as I hated these functions, I very much enjoyed watching Carter. He’s awkward but in a way that only makes him hotter. You know the kind, glasses, sweaters and that hair that can’t be tamed. He always looked like he had just gotten fucked and forgot to fix his hair afte...

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The Babysitter and The Nudist Campers Chapter 4

"You boys need to get those trousers off and join the rest of us in natural nakedness."

CHAPTER 4     As only to be expected, the sun came up that next cloudless morning on the faraway shimmering horizon highlighting the shapes of the merchant ships sailing in both directions in the deep channel that paralleled the beach with narrow alignment making them all seem a little too tight for comfort. Strangely, they were close enough to make out a number of distinct details about their cargo and design, but they w...

The Babysitter and the Nudist Campers Chapters 1 - 3

She never knew getting it from behind could be so satisfying.

Little Dolly Packer hadn’t been a babysitter very long. In fact, she had only started to babysit for money the previous month. Her father was away on a long sea cruise earning much needed cash for the family of five. She and her three other younger sisters were a burden on their sickly mother’s shoulders and Dolly did her best to help out with the earning of income to put food in their mouths and the rent inside her mothe...

They hired a hot babysitterShe was eighteenShe communicates on twitterAnd wears the tightest jeans She's quite a flirtLikes to prance aroundShe wears tight shirtsHer breasts are quite pert This girl was no virginShe acted like a slutShe's really hot in personAnd wiggles her sexy butt After the couple came homeThe sitter was laying downShe was talking on the phoneShe had put on her nightgown She didn't hear them come inShe...

Somebody Had To Take The Babysitter Home

She needed to keep her job, he needed something else.

Mike’s night was falling apart. “But honey, this is supposed to be a romantic evening with,” he struggled to phrase it with finesse, “an intimate ending. How are we supposed to do that if you end up falling asleep before I get back home? Can’t we just call her a cab?” His wife, Cindy, sighed in response. “Sweetie, someone needs to bring Megan home, and I’ve had too much wine, so it’s going to have to be you,” she explaine...

Sweet Little Katie— Part Two

Sometimes teasing can get out of hand.

It was Friday afternoon and Katie was walking home from school by herself. Her best friend Emily usually walked home with her, but today she had some group project to work on after school, so Katie was walking alone. Katie loved to stroll down the main street of her little village on the banks of a lazy river, with its variety of little gift shops and antique stores. It was a warm spring day and there were lots of people...

It was twenty seven minutes to two. Twenty seven minutes until I’d see him again. I’d deliberated over what to wear all week and even after getting dressed I’d changed three times. I’d done my makeup carefully; painstakingly trying to emanate online contouring tutorials. Letting out a breath, I frowned at my reflection. I was trying too hard. It bordered on ridiculous. I had far more important things to worry about. Like...

Jules

When Jules came to live with us, little did I know...

Four years ago, my son - Ethan, was born. We needed a babysitter for those times when we went out or would be late returning from work. We had a neighbor's girl named Jules that was highly recommended and mature for her 14-years of age. She really hit it off with Ethan, and he absolutely loved her. About two years ago my wife abandoned Ethan and me, leaving us to have to rely more on Jules than I’d have liked. Ethan took...