The Babysitter
- 2 years ago
- 38
- 0
What began as a disappointing evening, became the greatest gift my wife Ann, ever gave me.
I was 32 years old and had just been promoted to sales manager at my company. My old sales team arranged a dinner to celebrate this achievement. My wife Ann was beautiful, smart and has always been my best friend and supporter in everything I have done. She took great care of our two young children, and she managed everything around the house so that I never had a worry and could focus on my demanding job. I knew I was a lucky guy, but just how lucky, I was about to find out.
The sales team I was leaving, planned a dinner at my favorite restaurant to celebrate the promotion. Ann was proud of me and very excited to make this night a very special one. She picked up our favorite babysitter, Susan, right from her school so we could get to the restaurant in plenty of time. Susan was a junior at the nearby Catholic School. She was a little on the shy side, but very conscientious and great with the kids. She was pretty with long dark hair and sparkly blue eyes. She was also athletic, at about 5'2" she played guard on her schools basketball team. She had been our main babysitter for a couple of years and had earned our trust and we both liked her very much.
As we headed for the restuarant, I told Ann, "You know, I don't think I have ever seen Susan in her school uniform before."
Ann smiled and asked me what I thought.
"I think she looks really nice, I bet the guys at school think so too."
Ann said, "I think so too, after I picked her up today she told me that there is a guy on the football team who has called her a few times lately, she is hoping he will ask her out."
"I just hope we don't lose our babysitter, it's so great to have someone like her," I told Ann.
Ann said, "I reminded her, that if she does use the phone, to keep it short so we can stay in touch. She told me that she understands how improtant that is, and promised to not tie up the phone."
We arrived at the restaurant to find most of the group already there. We ordered drinks and socialized for close to an hour, before ordering dinner. Once we had ordered, Ann excused herself and told me she was going to check in with Susan. She returned just a minute or two later and told be that the line was busy, so she would try again in a little while.
We had a great dinner with some amazing wine. Before they came around to order dessert, Ann left to again check in with Susan. This time she came back with a distressed look.
She said, "Jim, the line at home is still busy. that is not like Susan, I am really afraid that something might be wrong. I hate to leave early and ruin your celebration, but I don't feel right about staying."
I told her, "Ann, your instincts are always pretty good, if you think we should leave, I'll just tell everyone that one of the kids is sick. They will undersand."
The drive home was about 30 minutes. A few mintes after we left, Ann called again and this time, Susan answered. Ann asked her what had happened that the line was busy for so long.
Susan told Ann, "I am so sorry, Mrs. Mann. I was only on the phone for about 5 minutes. I just now noticed that when I hung up, the phone was not set right in the reciever, so that is why the line has been busy. I am so sorry, I really messed this special night up for you and Mr. Mann, I feel just awful."
Ann told her, "Well, I am glad that there is no issue with the kids or the house. I know accidents happen, so don't worry, we will be home in a few minutes."
Ann took a deep breath of relief and told me that eveything seems to be OK. "The only problem now is that your big night has been wrecked."
"Well, things like this happen, I will be fine." I told her.
A minute later Ann looked at me with a sly smile. I said, "What is that look about?"
She kind of bit her lower lip and said, "I have an idea that you just might like."
"OK, I give up," I told her.
"Jim, how would you like to have your favorite fantasy come true tonight?"
"What do you mean by that?"
"You know Jim, you have always told me how you think about spanking a catholic school girl, right?"
"Ann, that is a fantasy, reality is a totally different thing. There is no way I could ever really spank Susan. How would that work?"
"Well Jim, I could tell that Susan feels really bad right now. I think she might feel a sense of justice, if you were to punish her for being a naughty girl."
"I could never find a way to do that, Ann."
"Jim, I know you would like to spank Susan if you could, right?"
"Well, maybe, I suppose, but that just could never happen in reality."
"Jim, when we get home, I want you to go upstairs and check on the kids. Take a few extra minutes up there. Meanwhile, I will speak with Susan and let her know how dissapointed we are, especially you, on your big night. I can play it by ear, but I have a feeling that I will be able to talk to her about what she did. I will tell her that we would like to pay her, but ask her if she agrees that she does deserve to be punished for her negligent behavior. If she agrees, I will tell her that Mr. Mann will drive her home and on the way, they could stop somewhere and she should allow him give her a good spanking. If she agrees, when you come down, I will say, I paid Susan so she is ready to go. That will be your signal."
While all of this sounded good to me, I could not understand how that conversation would go or that there was any real chance of this actually taking place. On the other hand, I know that my wife can make a very convincing argument about just about anything and if anyone could pull this off, it was her. So then I wondered, how I would act if it actually came to me giving Susan a spanking. Fantasy is one thing. This is a real girl. I would not want to hurt her and how would she act in such an odd situation?
Once we arrived home, it was clear that Susan was really shook up. She was clearly upset and embarrassed about what had happened. I went right upstairs as my wife and Susan sat down in the living room. I made sure to give them plenty of time to talk. Finally, I decided I needed to make an appearance, no matter how odd that would feel.
Ann was alone in the kitchen, she told me that Susan was in the rest room and would be ready to leave in just a minute.
I just gave her a quizzical look, and she said, "It will all be good, Susan understands what you need to do, so don't worry about it, take your time with her. I will be waiting in bed, when you get back."
Susan appeared a minute later. She seemed a bit uncertain, but she looked so nice in her plaid skirt, white blouse and navy blue school vest, short white socks and saddle shoes. Now I was really beginning to feel nervious. Was I really going to stop on the way home, put her across me lap and spank her? Would I pull up her skirt or even take her panties off? It was hard to imagine, but it was time to leave.
Once on our way, Susan told me how badly she felt about wrecking my night. I told her that I was sure everything would be just fine. I asked how the kids were. She kind of lit up a bit and told me that kids were great, as always. She told me what they had for dinner and about some of the games they played and how much she enjoyed them.
Then with no hesitation she said, "Mr.Mann, if you take the left just ahead, there is a quiet little park, just down that street, where we could go."
I put the blinker on and could feel my hands shaking and my mouth getting very dry. I took the left and drove very slowly down the street untill Susan pointed out the small parking lot a few feet ahead. I turned into the lot and pulled into a spot near the only light in the area. Susan pointed out a small bench about 30 yards away and asked me it that looked like a good spot.
"Sure Susan, that should be fine."
I'm sure she heard the nervousness in my voice, she said, "Mr. Mann, I love babysitting for your kids. I always try to do my best. I know I was careless tonight. I have a been a naughty high school girl and I need to learn from this. I trust you completely and promise to do whatever you ask, so don't worry about that. Let's walk over to the bench, OK?"
I looked into her pretty blue eyes and just nodded. She opened her door, got out and waited for me to come around and take her arm. We walked slowly toward the little wooden bench. It was very dark and quiet. Only the little bit of light from the parking lot and the moon, allowed us to find our way.
Once at the bench, we both sat down. Susan removed the vest she was wearing and placed it over the back of the bench. She reached for the top button on her white blouse and said, "Your wife told me that if I did not want my blouse to get wrinkled, it would be better if I took it off, is that OK?"
"Yes Susan, I would like to watch you remove your blouse."
She slowly fumbled with each botton until all were finally opened then she pulled the tail out from her skirt. She held her blouse open allowing me to see her thin white bra as she slid the blouse off and placed it neatly on top of her vest.
I told her how pretty her bra was.
Susan thanked me got a serious look on her face and turned sideways, toward me. I put my arm on the back of her shoulder and gently guided her across my lap. I helped her get into the ideal position. Now I had this 16 year old babysitter lying across my lap as I looked at just the back of her bra and her uniform skirt. She turned her head back to see me and said, "Mr.Mann, I need you to spank me now."
"OK Susan, that is what I am going to do. First I need to lift your skirt up and make sure it stays out of the way. So if you can hold pretty still, that will help. I lifted the hem of her uniform skirt up and pulled it nearly up to her bra strap. She moved just a bit forward so that her panties covered bottom, was now the highest part of her body. The silky white panties matched her bra. I told her they were a pretty set and I was lucky to get to see her in her underware.
Susan again looked back and said, "Mr. Mann, are you going to pull down my panties before you spank me?"
"Yes Susan, I need to take your panties off, so if you just lift up a little bit, it will make it easier for me to pull them down."
"Yes sir," she said as I worked the smooth silky panties down across her firm and perky bottom, she then bent her legs up, allowing me to easily removed them.
I gently rubbed my right hand over her smooth little bottom and said, "Susan, I don't want to hurt you, so at anytime, you can let me know if it's too hard or if we should stop, alright?
She just replied, "I need to be punished, Mr. Mann."
I then gave each cheek a firm, but not hard blow with the palm of my hand. Her bottom tensed up slightly. I lightly rubbed my hand over her bottom and told her to try to relax. "Maybe start by parting your legs a bit, it will keep you from getting to tense."
She parted her legs as I had suggested and I began to spank her with an assortment of taps with my fingers, followed by firm smacks with the palms of my hands. Her legs kicked up a bit following some of the harder swats. I asked her if I was hurting her too much, She said, "Not at all, Mr. Mann, it would be alright to spank me a little harder, if you want to."
I got into a very study pace trying to make sure I spanked each cheek with the same firmness and number. A few times her bottom would tense up, but only for a second. Then she would again part her legs in order to relax a bit. Before too long, I realized her legs were far enough apart to offer another interesting view. I helped her to move forward on my lap, just a bit, and could now see that her clit was becoming a bit damp. I slowed down to admire the scene.
Susan turned her head again and asked, "Mr. Mann, are my legs open enough for you to have a good view?"
"Yes Susan," I replied, as I slowly moved my fingers which had been rubbing her bottom, down between her legs and gently stroked the moist clit, I had been admiring. Susan was now moaning with pleasure as my fingers found just the right spot. I then worked two of my fingers well up inside of her. She squirmed and began to moan louder and louder letting out a low scream as my fingers found their way deeper and deeper. Finally she screamed, "I'm coming Mr.Mann, I'm coming....don't stop, please don't stop!
Finally it came to a end. She said, "Mr. Mann, Can I just lay here for a minute?"
"Sure Susan, everything is fine now."
"Mr. Mann, if you would like to see me tits, you could open my bra, if you want to."
"That would really be nice, Susan," I said, as I undid the single hook and helped her to sit up on my lap. I held her breasts for a while, and kissed her rock hard nipples. Finally Susan said, "Mr. Mann, I know that your cock was really big and hard while you were spanking me. I need to take down your pants and suck your cock until you come in my mouth, OK?"
With that, Susan knelt on the grass in front of the bench, opened my belt, unhooked my pants, pulled my zipper down, then took down my pants and underpants. She sucked my dick for no more than a minute or so until I shot blasts of cum down her throat like I had never done before. She not only swallowed it all, she licked up every bit she could find off of her face, chest and tits.
Finally we both got dressed and straighened up. When I dropped her off she said, "Mr. Mann, thank you for taking the time and caring enough to give me such a good spanking. I will never forget it."
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Jessie Flanders checked the time on her cell phone as she neared the elegant Carter home. She was a minute early for her babysitting job. As she made the turn onto the Carter’s front walk, a cab pulled to the curb and blew its horn. She reached the door and was about to ring the doorbell when it popped open. A good looking woman in her late thirties dressed in dark slacks and sweater peered at her over her glasses. “Are you the babysitter?” she asked. “Yes I am,” Jessie said. “The sitter’s...
I walked towards the door and saw her through the small window. 'Oh, there she is the barely legal dazzling brunette I have babysitting my son. What I wouldn't do to give a ride, and I don't mean in my car. Shit, she is wearing a dress like that to a babysitting gig? Is she trying to turn me on now?'I opened the door and saw her through the glass storm door. She just smiled and waved for a few seconds, and I had to return the favor.I opened the storm door too. "Hello, Alli, you are looking...
TabooThe following is a continuation of the original story "The Babysitter" previously published on this site under the Taboo category. If you haven't read the original story, please do so before reading this one, as it will introduce the characters and circumstances so this one will make more sense. * The extra week that my wife was gone stretched into two. Amy had gone to her sister's to help her while she and her husband were having troubles. They had split for a time, and Amy's sister was...
TabooBlondie/Dennis The Menace: The New Babysitter (Or When Dennis Meets Blondie)by Sniper32One Friday night Dennis was introduced to his new babysitter, a nice younglady named Blondie Bumsted. She was a 35 years old friend of his mother, shewas a stunning 5'9, slimmed hipped, long legs, a nice ass and a perfect setof 38c breasts.Denise's parents Henry and Alice were going out for dinner and dancing fortheir anniversary and would be gone most of the night.Now as everybody knows Dennis is a handful...
I couldnt believe I was staring at a picture on my computer of my 18 year old babysitter's naked pussy. Leaning back behind my desk in my home office, maximized on my monitor, was a picture of Missy lying on her back nude with her legs spread, and a perfectly shaved, glistening pink pussy pointed at the camera. Wow. I mean -- wow. It was the second of the fifteen pictures that I'd opened. The first pic, ME, had a nice smiling photo of her sitting on the bed wearing a bra and panties. And, of...
Jessica's Live-In Babysitter - Part 1 by CutePatti ________________________________________ Sam had doubts about Becky's idea when she had broached it to him over lunch at the office. Sam and Becky had known each other for many years and had even had a serious relationship at one time. But that was long over and they were able to remain friends since they worked for the same company. "I have a problem," she said, "and I think you're the perfect solution!" She went on to explain...
I love my wife. One of her best qualities is how she let’s me treat her thirteen year old daughter, Michelle. My first treat was when she informed me that I should be the one spanking her, and that she would be stripped first. I went along and spanked her thinking it was just the way they did things in their family; the fact that I was enjoying myself I kept to myself. Than one day I came home to see that my wife had invited all of her friends over and had Michelle in diapers on the...
It's never easy for a child when his parents split up. Circumstances affect circumstances and usually for the worse. In Billy Bonds' case, his parents' impending divorce was all the harder because he knew deep down that, despite what they always say, he was the cause of it all. He wasn't, of course. But what's a 14 year-old boy on the edge of puberty and teenage defiance, painfully self-aware and utterly confused about everything supposed to know about life? You could say Billy was a...
This is my first try… Leave comments to what you think could be improved! * * * It was six oclock on Friday night when Abigail began to make her way down the street towards the OLachlan house. She grumbled under her breath. There were plenty of things that she would rather be doing on a Friday night that didnt involve babysitting two teenage brats. Her mother had pressured her into babysitting the OLachlans kids, though Abigail didnt see why they needed babysitting. The oldest, Jacob, was...
Introduction: After Jimmy takes Kayleens innocence, breeds & seeds her. she gets set for another lesson- swallowing protein. Then Jimmy teaches Kayleen how a real man pounds a real woman. And then.., all hell breaks loose. Me, Beth and Kayleen took a breather to catch our breaths. Then Beth says to Kayleen, Now that my husband filled you up by shooting his pearly-white spunk deep inside your young, fertile womb, youre gonna give him a blowjob. Then I chimed in by saying, And not only are you...
Instead of taking their daughter to a daycare, they have a babysitter come in to watch her during the day. They had just recently hired a new babysitter, Jennifer, an 18 year old freshman at the local university. Jennifer only took afternoon and evening classes, so she was able to babysit until Tina or Paul got home. Jennifer stands average height, with an average build. She did play sports in high school, along with being a cheerleader. She was excited about finding the babysitting job so...
Paul and Tina have been married for about 6 years, and have a 3 year old.Instead of taking their daughter to a daycare, they have a babysitter come in to watch her during the day. They had just recently hired a new babysitter, Jennifer, an 18 year old freshman at the local university. Jennifer only took afternoon and evening classes, so she was able to babysit until Tina or Paul got home.Jennifer stands average height, with an average build. She did play sports in high school, along with being...
Originally published as Best Father's Day Gift Ever but due to low response I am re-posting under a different title. True storyIf you have read our earlier posts, you will know that nearly 6 years ago my dad, Liam, had done a nude painting of Babs, which she gave to me for my birthday. You will also know that Babs and my dad have had sex before also on more than one occasion. My dad and I look very much alike so it wasn’t difficult to see why Babs fancied him so.Last year, Bab’s mom Helen was...
I awoke the next morning after a night of intense lucid dreams with no recollection of how I had ended up in my own bed. All I remembered was venting my unmet desire to get laid with a quick, loveless wank. It took me a while to realize Emily had come to my room to wake me up.She was gently rubbing my cheek with the back of her hand when she spoke, “Rise and shine, sleepyhead. Breakfast is ready?”I looked at her through half-closed, drowsy eyes and mumbled something unintelligible about...
TeenIntroduction: This is the continuing story of Rose, her husband Ron and the babysitter Jenny. Rose had just recently found the opportunity to dominate another and to even punish and be sadistic. She found it a rush and it was changing her life. Jenny lived with so much guilt because of an over religious mother. Their story continues. Rose woke up first and realized it hadnt been a dream. Here she was in the bed with the 16 year old babysitter Jenny and her husband. She could hardly believe the...
My wife, Amy, had left to go see her sister for a few days, apparently her and her husband were having some marriage troubles and she wanted to be there to support her. That left me at home to watch our two little girls Sarah, who was three and Paula, who was five. They were good girls and helped Daddy as much as three and five-year old girls can. My wife was supposed to be gone for a week but maybe longer, it would depend on what happened with her sister. I didn't mind her going, I try to be...
TabooIn a sudden delusion caused by two simultaneous synapses crossing each other, I thought, "Gee, wouldn't it be keen to tell the story of how I, Harvey Marcus, got started with all of this screwing around. I mean, it didn't just happen out of nothing. Everything has a cause, a spark, an ignition. So, here's my first Official Retrospective. Appropriately, it is my Origin Episode, how I involuntarily got sucked into a campaign of accidental sex with all of the world's eighteen-year and older...
Introduction: Submissive babysitter Jenny seduces her sexy teacher. Bedding the Babysitter 4 Brief Summary: Jenny attempts to fulfill an order from one of her two Mistresses, when she meets with her unknowing teacher to finish a seduction she had slowly been doing all week (a brief sub-plot in Bedding the Babysitter 3). Note 1: I recommend you read parts 1-3 to know the complete story of Jenny from shy, nervous in the closet lesbian to submissive, sexy cheerleader and seductress. That said,...
Falling victim to the fashion trend of the tight black leggins, left almost nothing to the imagination, as her legs, small hips, and the tiny gap between her thighs, were open-season for anyone who dared to view them for more than two seconds. She was not the first babysitter Mister I would have chosen to watch his k**s, since Teagan was just a k** herself, yet he also didn't dare to tell his wife that he found her to be somewhat of a distraction as well."The k**s love her," she always said,...