The Babysitter
- 2 years ago
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Introduction: It was punishment time…. Casey entered the van. The automatic doors locked. Jane said nothing and drove. Eventually they arrived at Caseys house. Jane told her to get out. Casey did and went inside. Casey wondered what was going to happen. Jane drove away.
About a week later out of the blue Casey received a call. It was from Jane. At the mere sound of her voice Casey began to sweat. She had been stressed all week waiting to see her punishment.
Jane was as nice as pie on the phone. She acted like nothing had happened. Was this lady fucked in the head Casey wondered. Jane asked Casey to come over Friday evening to baby sit for awhile. She was asked to arrive at seven pm. There was no further discussion.
Until Friday night Casey thought through all sorts of scenarios. What could happen to her at the house. She had no idea. She thought about up and quitting but she was excited to see her punishment. Before going to baby sit Casey showered and waxed to be nice and clean for the weekend. She put on a pair of blue tight jeans. Casey had the perfect body for them. The pants hugged her curves and ass like they were painted on and her body made them look awesome. If you looked at her from behind she had the perfect little space between her crotch and legs that looked like it could fit a cock in when she stood with her back to you.. She wore a button up long sleeve cotton white shirt. It fit her figure really well.
When Casey arrived at the house it was dark. A note on the door said to let herself in. Casey did so. The interior of the house had a few lights on but looked deserted. Casey could hear talking in the basement area. She was reluctant to go down there as she knew there was a sex room.
Casey had a drink upstairs while she waited for someone to show up and give her instructions. She called out and the muffled voices stopped.
A minute later she could hear footsteps coming up from the basement area. It sounded like heels clicking on the hard cold marble floor. Louder they got. All of a sudden Jane appeared in the dark hallway.
Is that you Jane, Casey asked. Yes you little bitch Jane answered. Are you ready tonight for your punishment? Yyyyyyes stammered Casey. Follow me then you little bitch Jane said with a firm voice.
Casey thought about running for the front door, but as that idea manifested in her head Jane had walked over to her and grabbed her tightly by her right arm. She pulled her down the hall. Jane was a lot stronger than Casey realized. Casey was dragged, her socks helping her slide to her doom.
Casey started pleading with Jane and asked her not to punish her too badly. Jane told her that it was her turn to teach her a lesson for fucking her husband and friends, then lying about it and taking her clothes from her home.
Casey could not escape the vice like grasp Jane held her with. Jane had an agenda. She pulled her down the stairs almost as if faster the closer they got to the basement sex room.
Casey had seen this room when she initially checked out the residence on her first night of babysitting. It was dark, windowless and filled with shit she had never seen before. There were sex swings, tables, chairs and other things. Not normal furniture. This shit would torture the recipient of it. Jane remembered the wall display of items. They were set up like a tool board in a garage. Dildos of all sizes, ball gags, chains, whips. Fuck she thought to herself. She was done in her hands.
Casey was pulled into the room. The large door loudly shut. In the room were 2 other people. They sat in the corner on chairs. It was dark. She could not tell if they were male or female.
Jane told Casey that it was irrelevant to scream for help. The room was soundproof. She did tell her though that she could scream as loud as she wanted as she was fucked. The sounds would turn her on more.
Jane told Casey to climb on a table face down that resembled a large letter X. The table was designed to have the recipients legs and arms spread in a wide x pattern and be strapped down by the wrists and ankles. The head unsupported would hang down if you could not hold it up. This would allow easy access to a cock for face fucking if so needed. Casey asked Jane if she wanted her to undress first. Jane yelled at her to get on the table now.
It was not built for comfort. The cold hard steel could be felt through her clothes. The leather wrist and ankle straps were also very thin and tightly tied. Jane pulled them hard as she strapped her down. This made Casey cry out. They dug into her wrists and ankles. Casey thought to herself. How many other poor girls have been abused on this table.
Jane looked towards the two people sitting in the dark corner of the room. She told them to watch how she disciplines cute little bitches for fucking and stealing things in her home without her permission.
Casey watched Janes feet walk around to her ass area and between her widely spread legs. Jane rubbed and massaged her lower legs through her jeans and then slowly and methodically massaged ever higher up to her asshole and crotch. This got Casey wet quickly. She bit her bottom lip lightly and moaned.
Jane was also getting a little excited. Casey could hear here breathing a little faster as she rubbed her cunt through the old denim jeans. Casey thought if Jane was gentle for her the pay back it would not be so bad.
Casey loved the massaging of her ass and cunt through the jeans. It aroused her and her clit even started to tingle. She then heard Jane whisper fuck this. Jane walked over to the tool board her heels clicking loudly as she walked with a purose. On the wall she picked out a large nasty looking black strap on. It was double ended. Casey lifted her head to look but the stress on her neck was too much. Down dropped her head towards the floor. In the brief time Casey saw that the strap on it was terrifying. The double end that Jane was wearing would only insert into her about 6 inches into her. The end Casey was to receive was a good 15 inches. It had slight ribbing on the shaft every inch of it. That meant Casey could count the inches that were shoved into whatever orifice Jane chose.
Casey started to protest. Jane walked around to the front of her. She grabbed a bunch of her hair and lifted her head by it. Jane knelt down and faced her. Casey could smell Janes breath. It was fresh like strawberries. Jane told her the more you complain you little whore the worse you will get it. Casey apologized. Jane let go of her hair and her head sank down.
Jane strapped on the dildo and moaned as it went inside her. It even had some sort of vibration mode as a quiet whirring sound started. Jane went back in between Caseys legs and started slapping her ass crack with the dildo. It was solid and hard. Casey pleaded for her not to use it on her ass. This made Jane hornier and angrier. Jane told her she was going to take all 15 inches in her ass.
Jane had a small knife on her. She took it and cut the top of the vertical seem of Caseys jeans at the belt line about an inch. It was the seem that went down through the crack of her ass. Casey thought to herself there goes another pair of denim at this house. Casey felt Janes two hands grab each side of the cut and start pulling. Casey wished the jeans would not tear apart and she would be spared the ass annihilation. The wish worked at first but then slight quiet tearing of fabric turned louder. Jane was using all her arm muscles. A loud rip separated the ass cheeks on the jeans right to her pussy area. Open the jeans lay spread apart and showing her ass. . All that protected her ass from the dildo was small thin smooth lacy pair of panties. Jane tore then off forcefully giving Casey a temporary wedgy.
Please lube me Casey pleaded. Warm wet liquid dripped onto and down her ass crack. It tingled when it made its way to her pussy. It was some sort of massage gel.
Casey waited and then it started. Jane grabbed Caseys left ass check and pushed it outwards to make some room. With her other hand she grasped the giant didlo and using it like a penis started massaging the big tip around Caseys outer asshole. Casey could feel it vibrating slightly. Casey thought to herself that Jane must be either getting off or building up to a huge orgasm. Jane did not rush. She moved the cock head of the vibrator up and down her slit. It prodded and probed Caseys pussy and entered it an inch. It then withdrew and slid from her cunt to her ass. It poked at her ass. It could not get in.
Casey knew it would hurt like a mother fucker but she wanted it over and done with. Casey told Jane to fuck her. Jane was furious. Jane yelled that she was controlling this show and to shut the fuck up. With that Jane snapped her fingers. Out of the darkness came one of the unknown people. He was a man Casey had never seen before. Tall, naked muscular and hung like a horse. Of him hung a throbbing hard 4 inch circumferanced cock that was probably 10 inches long. Jane told the man to fuck her face and throat so she would shut up.
Casey tried to keep her head down and turned away. The man was too strong. He grabbed a huge clump of hair and twisted her head upwards. Casey kept her mouth closed. The man slapped her face repeatedly with his hard angry cock. Pre cum drizzled and splashed her face. He then plugged her nose with one hand and forced her to breath in and out of her mouth. When she opened her mouth for a gasp that was when he shoved his cock in. Hard and deep. Casey had never had a cock go at least 3 inches down her throat. Pre cum lubed her passage and it slipped in and out nicely.
Jane also assisted in the mouth opening. She hooked two fingers from her right hand into Caseys mouth like picking up a fish and wrenched her mouth open.
Jane then had her way while the face and throat fucking took place. Casey felt the tip of the dildo break the precious puckered vault entrance to her asshole. Once it broke in she counted the number of marked rib inches on the beast. She started at one two three and then it got up to fourteen. The pressure and pain from this giant thing pressed all the way up into her stomach cavity. The further Jane entered Casey the more excited she got.
Casey passed out a few times from the sheer pain but when she came to she knew Jane was finally getting off from the vibration and sheer dominance she possessed over her. Jane thrust her strap on hard up into Casey. It was if Jane had a giant penis. In and out repeatedly. Caseys firm tight ass rose slightly with every thrust. Casey had a small orgasm from this abuse but her attention was mainly on the cock stabbing her throat. The fucking had been going on for about ten minutes and the room had warmed up with the door shut.
All parties involved were sweaty wet messes. Caseys hair hung down dripping with sweat. She could smell cum and body odor from the man.
She knew when the man was ready. It was like she had an iron rod in her mouth with pulsing veins around it. She had never sucked or been force fed such a hard thing in her life. The man plugged her nose and rammed his cock as far as it would go into her little throat. Casey was forced to swallow. Casey did not realize how so much cum could come from one man. It continuously pumped out his gigantic cock for what seemed like ten seconds. As she was forced to swallow Jane pulled out of her asshole. Her ass puckered shut. Casey could not cry out or make noise during the sex romp. She just made gurgling and choking sounds.
Jane walked up beside her and rubbed her flat little stomach. It was now distended somewhat from the load of cum. Jane whispered to her that she should not drink lots of protein like that. It may make her fat.
Casey lay there exhausted and motionless. Sweat dripped off her hair ends as if she had been out in the pouring rain. She was sore and in pain.
The man grabbed her now soaked button up shirt she was still wearing. Like an animal he tore it off and used it to clean his glistening wet cum dripping cock. He threw it on the ground when he was done with it.
Casey lay there spent and finished. She thought it was finally over. Jane was beside her. Casey was so out of it she did not realize Jane had knelt down beside her. Jane told her quietly that they were almost done.
Casey knew her cunt was going to be the recipient of something from Jane. Jane walked back up to the board and pulled off some anal beads and two vibrators. The anal beads were a long pink string of rubber attached balls. The smallest probably about the size of a little grape. The balls by the end were like pool balls. The string in total was about a foot long.
Jane knelt beside Casey and immediately turned on both vibrators. They had fresh batteries and sounded good to go. Jane jammed them in Caseys pussy with ease as lube and moisture had already lubricated her inner thighs and asshole. Jane asked told her that this was what it is like when two guys double your cunt with cocks. She thrust them in and out quickly with an angry look on her face.
As the vibration continued a large orgasm welled up in Caseys little abused cum filled body. Jane could see Caseys face mouth falling open in pleasure and her hips twitching and starting to writh. With that Jane reached around and jammed the anal bead set all the way up in her asshole to the last one. The combination of stimulation made Casey scream out unhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhh and move her hips and ass furiously up and down. The ties on her wrists and ankles held her limbs in place and by now had started to cut through her skin.
Casey collapsed and passed out for twenty minutes. When she awoke she had been untied. The other people were gone. Casey was laying on a bed in a spare bedroom. Jane brought her some of her clothes and told her to get dressed and go home. On the pile of clothes was five hundred dollars. Casey got dressed and saw the bind marks on her wrists. What kind of story could she say caused that if anyone ever asked?
As she left the residence Jane told her she would call her again.
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I was in desperate need of a night out so I asked my husband if we could get a babysitter for the boys and go to dinner. He happily agreed and called the neighbors to see if their daughter, Susie, was available. Thankfully she was so we set it up for Saturday night. Saturday came around and I was more than ready to go out and look sexy for my hubby. I chose a short black fitted dress that hugged my hips and was low in the front to show off my C cup tits. I threw on some 4in black heels and let...
BisexualIntroduction: OK readers, here comes a LONG story that I have been working on for a while. I dont think this will become a series unless I get requests for it. Tina comes home early and finds a surprise in her bedroom, the babysitter masturbating on her bed. She could just fire the girl, but decides to punish her, while living out one of her fantasies. Paul and Tina have been married for about 6 years, and have a 3 year old daughter. Instead of taking their daughter to a daycare, they have a...
The new babysitterAt this time i want to tell you a story of when i got a new babysitter.one evening my parents chatting and came up with the idea of going out on a romantic dinner for two being they were married for about 11 years and didn’t get the chance to go out much for some alone time for a long time now,being i was sick often and hadand therapy and other activities and a baby sister my mom had her hands full.my dad brought up the idea of perhaps having dinner just the two of...
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...
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 explained as she looked at him with a face depicting the annoyance of telling a...
Oral SexI 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...
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...
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...
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...
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...
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,...