Mrs. Sandra Sheppard

            Mrs. Sandra Sheppard looked at her form in the full length mirror in her bed room and liked what she saw. For a 53 year old woman she was still smoking hot, she was only 5’3”, with a petit build, a firm pair of 36 D’s looked even bigger on her small frame, long red hair cascaded down her back. He husband of 30 year died 2 years ago and once she had grieved she began the process of re-building her life.

            The last 9 years she and her husband where together they had played around with BDSM. She had always been the submissive but for 1 time, and that 1 time has stuck in her head ever since. She loved to dominate and vowed to jump into the life style with full force.

            It took over a year for her to transform her new house. Sandy was fortunate that she was wealthy and could afford to do what ever she wanted to do. She had a full basement stocked full of BDSM toys and furniture. She had a closet full of fetish clothing and heels, so now all she needed was a few more slaves to play with.

            She had 1, an 15 year old male with a nice fat cock. He was actually he step grandson, his parents where killed in a car crash 6 months ago. So she took him in as long as he came in as her slave and play toy. He was all that was left of her family, but she wasn’t about to just put him in the will and not done anything to earn it, after all it would be close to a $77 million dollar inherence.

            His main duty was to be naked and do housework. She liked to hang weight from his balls while he did his chore, but she did have bigger plans for him in the future.

            “Put your driving clothes on toy, you’re driving me to dinner in 30 minutes.” Sandy said.

            “Yes Mistress.” He replied.

            They had 5 minutes to go when she inspected him. She had him in a short kilt, thigh high stockings with 6 inch heels, and a shirt and tie. She had him lift his kilt and she took hold of his balls and attached a leather and steel device to them. She called it her ball reigns, a needle was actually pushed into each ball and with a push of a button, electricity would travel through the appropriate needle and he would know to turn left or right. He hated the device, while she kept the settings low while he drove, she enjoyed turning it up and making him dance and cry at other times.

            She had him drive her to her country club where she was to meet with a new slave/employee.

            Sandy had reserved a privet room to eat and talk with the MILF that she had been in contact with. Sandy sat an ordered a glass of red wine and waited, she had come 15 minutes early so she could ensure that her demands had been followed. The waitress, Jamie was a friend of hers, informally of course, but they took care of each other.

            “Are you dining alone Mrs. Sheppard?” Jamie asked as she poured the wine.

            “Not today dear. I am interviewing a new slave. So needless to say I want this to remain quite.”  Sandy said as she slipped the girl 3 $100.oo dollar bills.

            “Oh course Mrs. Sheppard, I would never tell a soul.” She replied

            “This is a picture of the girl. Her name is Tina; please bring her back here when she arrives.” Sandy said, handing her the picture.

            “Wow she is beautiful Mrs. Sheppard. Be nice to play with her one day.” Jamie said.

            “You never know love, you just never know.”

            Jamie brought Tina back to the table, she was 3 minutes early, and Sandy liked that.

            So formal introductions where made and Lunch was ordered. Sandy wasted no time filling Tina in on what was expected of her. Sandy went over her hours and her pay and benefits. Sandy knew that Tina had a 13 year old daughter at home, but she would still be keeping long hours. Tina was originally looking to just be a slave, she experimented in collage and her and her ex played every once in a while. But when Sandy wrote to her on the BDSM personals site and offered her a job to boot, she just couldn’t resist.

            Sandy explained that while she would be her personal assistant, she would also be her slave and she told her that she loved to inflect pain and humiliation on her slaves, and her mouth, ass, tits and pussy where no longer hers. Tina was excited and agreed.

            Sandy pulled out a bunch of paperwork for Tina to fill out. First up was a 1 year slave contract, the rest was IRS and business shit.

            So with all of the mundane shit out of the way, Tina paid the bill and they left.

            Sandy had Tina follow in her car to the next destination.

            Sandy took her to the local fetish boutique and went shopping.

            “Hello Bridget, would you please set her up with the nicest sluttish clothes you have.” Sandy said.

            “Of course Mrs. Sheppard the sales girl replied

            And so it began, the girl measure Tina and then went to work. Within 10 minutes there was a pile of clothing and shoes laid out for Tina to try on.

            “We won’t need a dressing room Bridget, she can try on everything right out here.” Sandy said

            Tina was shocked but didn’t want to blow it on her first day so she stripped down and began trying on the clothes. An hour later, sandy paid for everything and had Tina dress on one of her new outfit before they left.

            They then went back to Sandy estate so Tina would know where to go.

            When they pulled into the drive and toy got out and opened Sandy’s door, Sandy turned up the device and pushed both buttons. He screamed and went to his knees. When he got up his cock was hard and making a tent in front of his kilt.

            Tina smiled when she saw it and giggled a little too.

            Once inside Sandy had both slaves strip naked and then sent toy to fetch drinks and took Tina into her office and showed her where everything was. She also informed her that toy was at her beck and call.

            “Stand straight up and put your hands behind your back slave.” Sandy ordered

            Sandy then took her time to check Tina out thoroughly.

            Tina was model beautiful. 5’9” with a toned body and long blond hair, a pair of 36 D’s stood out proudly form her chest and her pussy was completely shaved. Sandy took a few pictures and had Tina do various poses for her.

            “Well we are running out of day light, so you first assignment is to teach toy how to properly kiss. Begin.”

            The next hour Tina taught toy how to kiss and then they practiced. By the time Sandy called a halt, Tina was wet and horny and toy had a raging hard on.

            “OK slut it’s almost time for you to return home. But before you leave I want to watch you masturbate and get your self off. Come here boy.” Sandy said.

            So he crawled over to her and she secured his hands behind his back and watched as his cock throbbed with the beating of his heart.

            Tina was slightly embarrassed but her fingers went to her pussy and she began playing with herself.

            Tina was released after she came and was told to report back at 8 AM the next morning.

Chapter 2

 

            Tina arrived at 8 AM, stripped naked in the garage and crawled inside. The sight she witness was awesome and scary at the same time. She began to wonder if she had made the wrong decision about serving this woman.

            Sandy was sitting in her chair, looking very relaxed and watching a DVD.

 Toy was leaned over a horse and chained down. His balls where confined in “the humbler” and his cock was pulled straight down and tied off; Sandy was using syringes and needles and was basically throwing darts. He had 4 in his balls, 1 in his cock and 5 in his thighs.

            Tina crawled over to her Mistress and kissed her feet.

“Worship my feet slut while I entertain my self some more.” Sandy said and turned her attention back to the TV.

            Tina began kissing her feet and sucking her toes.

            “Watch the screen slut.” Sandy ordered Tina turned to watch the boy’s torture and derogation.

            The movie lasted another 20 minutes, Tina soon discovered that her pussy was wet just from viewing it, that and her Mistress running her heels over and into her tits.

            “I do love making movies slut. And I do have several staring roles for you too. But for now there is other thing’s that must be done. Come with me.” Sandy ordered. Tina crawled behind her down into the dungeon. Tina was again awe struck; this was the largest dungeon she had ever seen.

            Tina was first put over a horse and a large butt plug was put into her ass. Sandy put a binder clamp onto her clit and pulled her over to a St. Andrews cross and secured there. Tina almost passed out when her most sensitive organ had been clamped, and moving was almost impossible. Sandy removes the binder clamp once she was where she wanted her.

            “I did tell you that I enjoy inflecting pain and humiliation on my slaves so get ready.”  Sandy said with a laugh.

            Tina took a deep breath and exhaled just as the whip made contact with her left tit.

            Sandy concentrated on her tits for a good 20 minutes, they where bright red and welted.

            Tina liked it a lot; no one had ever beaten her like this even though she had begged for it.

            Sandy put a pair of nipple clamps on her next and whipped her tits a few more times.

            Sandy took a break and went upstairs with out saying a word. She wanted the clamps to work their magic while she was gone.

            Sandy smiled when she returned. She was caring a large cock in her hand, Tina saw a straw coming out of the tip when sandy came in closer.

            “Thirsty slut? Would you like a drink of water from this cock?” Sandy asked

            “Yes please Mistress.” Tina replied.

            Sandy held the straw to the woman’s lips and Tina drank heavily.

            “Are you ready to be marked as my property slut?” Sandy asked as she sat the cock down.

            Tina had no idea how she would be marked but she was open to anything so she answered yes.

            Sandy smiled as she walked over to a rolling tray and pulled it over to Tina.

            On the tray was a long needle, a cork, forceps and alcohol.

            Sandy smiled as she reached out for the chain that connected the 2 nipple clamps and began to push down.

            Tina closed her mouth hard as she realized what her Mistress planned to do. The nipple clamps would not be opened to be removed, but pulled off with force. Tina’s tits where stretched to their limit and then the clamps began to slid off; pain exploded when they came off all the way.

            Sandy simply laughed. “Very good slave, I’m impressed. The last girl I did that too cried and begged for me to stop. She left me shortly there after.”

            Tina tried to smile. Her tits had never hurt that badly before but it still made her pussy wet, she always thought that she was a true masochist.

            Sandy then picks up the forceps and clamped it to Tina’s right nipple. She then got the needle and slowly pushed it through Tina’s nipple and into the cork; Sandy puts a large golden ring into the hollow end of the needle and pushes it on through. When Sandy connects the ring, she moves to the other nipple and repeats the process. Tina is wet and in serious, erotic, pain, her nipples feel swollen to twice their normal size, which is exactly what Sandy wanted.

            “Stick out your tongue slut.” Mistress Sandy ordered.

            Tina stuck out her tongue and Mistress Sandy promptly pierced it and inserted a barbell stud.

            “There we go slut. I love a pierced tongue on my clit.” Sandy said.

            “Thank you Mistress.” Tina said.

            Sandy felt up Tina’s abused tits and ran her hand down the woman’s belly to her pussy.

            “Your wet slut, I take it you’re enjoying yourself?” sandy said with a laugh

            “Yes I am Mistress.” Tina replied.

            Sandy was please with this response. It was looking ore and more like Tina would turn out to be the perfect slave that she had been searching for.

            Sandy released Tina and they went upstairs. Tina sat down in her chair and Tina knelt before her.

            Sandy lifted her short skirt and merely blinked at Tina. Tina’s face went right in and began to eat out her Mistress.

            Tina ate pussy for over an hour, she was loving it but she wanted to cum herself.

            “Your very talented slut.” Sandy said as she gasps for breath. She had just finished her 7^th orgasm in a row.

            “Go get your water and bring me a bottle from the fridge.” Sandy said as she straightened herself up.

            They both drank deeply and then Sandy sent Tina into the office to get some work done.

            Sandy smiled when toy came crawling in and kissed her feet.

            “And how was your day toy?” Sandy asked ass she stroked his hair.

            “It was good Mistress. I aced all of my tests, including gym.” He replied

            “Very good toy, so this will be the last week of school then?” sandy asked

            “Yes Mistress, this Thursday.” He replied

            “Very good, I will keep my promise and give you 1 week to do whatever you want with in reason then your training will really begin.” Sandy said

            “Thank You Mistress. Permission to do my chores?”

            “Of course toy.”

            Sandy went into the office to check on Tina’s progress.

            Tina went to her knees the second she saw Mistress Sandy.

            Sandy looked over everything and was once again impressed with Tina’s abilities.

            “I’m almost done balancing your check book Mistress.” Tina offered.

            “Damn slut you do know your shit don’t you?” Sandy said.

            Tina simply smiled at the praise.

            “Finish up what you’re doing and call it a day slut.” Sandy said and then left the room.

            Sandy returned a few minutes later and sat a strap on dildo on the desk next to Tina and walked back out with out saying a word.

            Tina finished up 25 minutes later, stretched and the put on the strap-on and went to find her Mistress.

            Sandy heard Tina moving around and ended up meeting her in the hall way.

            “I am going to run a test before you leave for the day. I am going out back. You watch for toy to come up and then you walk out 20 seconds later, understood?” Sandy said as she headed for the4 back door.

            “Yes mistress.” Tina replied

            Sandy sat down on the rear deck and toy came up to her immediately and fell to his knees.

            Tina counted out and stepped outside.

            Toy turned and looked at Tina and was once again awe struck by her beauty. The he saw the cock sticking out and crawled over to it and took it in his mouth, his face burned bright red with embarrassment.

            Tina smiled down at him and sandy clapped her hands in approval.

            “Very good toy you have passed this test. The next cock you suck with be very real so preparing yourself.”

            ‘Thank you slut, you’re dismissed for the day.” Sandy said

            The next day Tina arrived and promptly stripped, she had inserted the butt plug before she left her place.

            A note with instructions had been left on the door, Sandy had a business appointment first thing and Tina was to continue her office work.

            Sandy called Tina and told her that she would be out all day and to take off at 4 pm.

            Tina was disappointed, but went about her work anyway and left at 4 Pm. little did she know that Mistress sandy had been keeping an eye on her most of the day, her house had been wired from top to bottom.

            The next day when Tina arrived, Sandy was sting down to breakfast, toy was cooking it. Mistress Sandy ate at the table, while toy and Tina ate from dog bowls on either side of her.

            Nothing was said at all, they all ate in silence. Toy cleared away the dishes and Sandy attached a leash to Tina’s collar and led her out of the kitchen.

            “I have a series of tests for you today slave. So far you have impressed me to the point that I am making future plans for us, however I was to be absolutely sure that you the slave that I want.” Sandy said.

            Tina felt her excitement build and her pussy got wet.

            “I try to be the best slave I can be Mistress. I am sure I will pass your tests.”

            “We shale see slut. Your first test will happen this morning. You will drive toy to school, once your there you WILL lure a boy away from school grounds and suck his cock to competition.” Sandy said

            Tina soaked in the order.

            “Yes Mistress.” Was all she said.

            “You will take this purse; inside it is a video camera for you to record everything.”

            Tina nodded and took the purse. She dressed in a black see-through top and a long mesh skirt and her heels.

            Toy showed her how to operate the camera on the way to school. Once they got there and she dropped off toy, Tina drove down the street. She saw a boy 3 blocks away and made a turn at the street before.

            He stepped into the street and Tina screwed up her courage.

            “Hay cutie come here.” Tina yelled out her window. He snapped his head up and walked over to her.

            “What’s up?” the kid asked.

            “Well I’m in the mood to suck a cock. Interested?” Tina said quickly.

            “Um, ah.” He stuttered

            “Oh just get in.” Tina said.

            He quickly got into the car and Tina turned and quickly found an ally.

            She made sure to place the purse in the right position and knelt down and pulled his cock form his pants. Tina was able to get him off in less then 3 minutes’

            “Oh yeah, that was nice. How old are you anyway.” Tina said as she swallowed his cum.

            “13” he replied.

            “I see, well thanks for the cum. See you later.” Tina said and got into the car and headed home.

            Tina rolled into the estate and into the garage. She quickly stripped off her clothes and went in to find her Mistress.

            Sandy was at her computer when Tina crawled in.

            “Back so soon slut?” Sandy said in surprise.

            “Yes Mistress, I did what you asked. It wasn’t hard to find a willing participant.” Tina replied.

            “Really, well lets view the tape shale we.” Sandy said.

            Tina handed over the bag and knelt by her mistress’ side.

            It was a digital recorder, so all Sandy had to do was plug it into her computer and download it.

            Sandy watched with fascination. Tina had indeed followed her orders to the letter and didn’t dally around either. That impressed Sandy even more.

            “Very good slut, I’m impressed. Now if you can follow the rest of what I have in mind then your life will be very fulfilling.”  Sandy said.

            “Thank you Mistress.”

            Sandy turned her chair so she was facing Tina. She reached out and began feeling Tina’s tits and playing with the nipple rings.

            “So how are my tits today slut?” Sandy asked

            “There sore Mistress.” Tina replied

            “I see, well that’s too bad because your next test will happen in 3 hours. We need to clean you out and get ready to go, so off to the dungeon with you.” Sandy ordered.

            Tina crawled behind Sandy down into the dungeon.

            Tina was secured face down on a table. Sandy readied the enema bag and went over to the table. This table was special, sandy could rotate it 180 degrees so a slaves head was facing the floor. Sandy inserted the tube into Tina’s asshole and then pumped it up so it couldn’t be removed, then attached the enema bag to the tube and opened it up and let the water flow.

            Sandy sat down and admired her slave. Tina was truly beautiful; her facial features where stunning, her athletic body was in perfect perorations and her long blond hair cascaded down her back to end just inches below her bra line. Sandy watched with amusement as her belly grew as the water filled up her bowels. Having experienced this before Sandy knew that the next hour would seem like an eternity.

            Tina was already measurable this was the one thing that she had always hated.

            When the first bag was empty, Sandy refilled it and let it flow in also. When it emptied, Tina looked 9 months pregnant.

            Sandy capped off the end of the plug that was inserted into Tina’s ass and removed the rubber line.

            Sandy then picked up a special contraption she had made. It was a pair of clover-leaf nipple clamps, but the chain was longer and ran out to a stainless steel “O” another chain ran from it to another clamp, which went on Tina’s clit.

            Sandy put the table back up right and removed Tina from it. Sandy put a leash onto the chains and pulled Tina back upstairs and straight out the back door.

            Tina couldn’t believe what Sandy was doing to her. Didn’t she know that the only thing she wanted to do was shit? Why was she prolonging it?

            Sandy took Tina on a tour of the property. The first stop was the horse barn. Sandy had several business ventures and one of them was Arabian horse breeding. Sandy currently had 5 mares and 1 stallion, which sandy introduced Tina too. Sandy had Tina get down on all fours next to the big stallion, making sure that Tina’s head was inches away from his massive cock. Sandy got up on her back and began to brush the big beast.

            When Sandy finished with his back, she took Tina out back behind the barn where the exercise ring was. Sandy and Tina hooked up 3 of the mares and set them to walking in circles

            Sandy smiled as she watched Tina who was about at the limit of what she could take. Her almost freshly pierced nipples throbbed and her clit had never hurt so badly. She also felt like she was about to explode from all the water that was sloshing around inside.

            Sandy had been making idle chit-chat the whole time, but Tina was no longer able to respond so Sandy took the clamps off.

            “Go over to that post and you may remove the plug from your ass slut.” Sandy said pointing to where Tina was to go.

            Tina waddled over and squatted down; she reached between her legs and found the valve and released all of the air that was in the bulb, pulling it from her ass was easy and all of the water came rushing out.

            Sandy used a water hose to clean her up and then told her to go shower because they had an appointment to be at in 1 hour.

            Sandy explained the meeting and what was expected of her to Tina while they drove. Sandy took pity on Tina this time and drove, but it would be the last.

            Tina was wearing a totally see-thru summer dress with 6-inch stilettos on, she was serving drinks and finger food Sandy and the 5 men that where there. Sandy had told Tina that the meeting was being recorded and she would be studying it in detail at a later date. Tina heard most of what was said, and soon found out that these where all movie producers, with free hands. At the end of the meeting Sandy announced a free for all with Tina in the middle. Sandy sat back and watched as all 5 took turns with her. Two hours later Tina drove them home. She was simply covered in cum, in her hair on her face and tits and leaking out of her ass. She didn’t hold back, not wanting to disappoint her Mistress, Tina had cum 9 times during the fuck session.

            “I don’t want you to shower until 9 tonight slut.” Sandy said.

            Tina just nodded as she paid attention to the road, the idiots where all out today. Sandy knew that Tina had to help her daughter with her math homework tonight. Would questions be asked?

            When they arrive back at the house they went into the office and discussed what was going to be happening with the producers. For 1, they had all pissed Sandy off with most of their ideas for new movies, and the fuck session was their undoing, blackmail still worked wonders. Sandy showed Tina her computer program that she had created; it was mostly ideas for movies that she would enjoy seeing. They ranged from G to XXX, Tina looked at the synopsis for most of them she was surprised to see that Sandy had an interest in K-9 and equestrian films. Tina wondered who would star in those. Most of the film she agreed that she herself would enjoy watching.

            Once they had exhausted the business topics Sandy told Tina what she wanted from her for the rest of the day. To teach toy how to properly eat pussy; she was also told that every time she saw him she was to kiss and cock tease him.

            So when toy got home from school Tina went to work. Tina had yet to speak to the boy, this was a first, and even then it was more like a teacher then a lover. Sandy did a lot of talking though. She made damn sure that he knew that the pussy that he was eating had just had 5 cocks in it and a few other humiliating things to go along with it. Tina was again surprised, this was her grandson after all so he never spoke in a harsh or mean voice, she was out to humiliate and cause pain period.

            Sandy had Tina eat her to several orgasms while toy watched; his hands had been secured behind his back so he could jack off.

            Before Tina left for the day, Sandy handed her first paycheck

Chapter 3

 

            Sandy was please that toy now knew how to eat pussy and she was determined to use the hell out of his tongue. Once Tina had left the first thing Sandy did was pierce toys tongue, it truly felt delightful. Seeing as school was winding down, Sandy decided that it was now time to fit him with a chastity device and keep 100% control of that huge cock of his. She had though about riding it once herself but that fact is she hates penetration, she never did like it.

            She had him get hard (which wasn’t difficult) and measured him; 10 and a quarter inches long and over 2 inches around. She then pulled out 2 ice cubes from her drink and ran them over his cock and balls to cool him down. Sandy then went into CBT mode and began squeezing his balls as hard as she could. She held his balls tight and used her other hand to slap around his cock. She rarely held back when it came to torture; she was truly a sadist and the fact that he was semi-related to her made no difference what so ever.