Nickel Mann

Training Step Mom

My father dumped my mother after 20 years of marriage; a wife who had worked to support him during law school, a wife who had acted as his secretary and Para Legal after passing the bar exams, she who had born my sister Amy and me, Jack Jr. My mother had ran the household, been a good wife, cook, maid, and mother. It wasn’t just dumping my mother that made it so bad, he used his legal skills to leave her with as little as possible.

He had married a “Trophy Wife” as soon as the divorce was final. Sure, his new wife was younger and sleeker, in fact, she was a knockout. She was tall and sleek looking; long shapely legs, a set of slender hips with a tight round bottom, large breasted. Her long silky flowing hair was always styled to accent her large blue eyes and fair skin. I would have lusted after her if I had met her first, or at least until I learned she was self-centered and a genuine bitch.

I was 16 and Amy was 13 when my father married his “Trophy Wife.” Our mother insisted on that my sister and I attend my father’s wedding. Even after all he had done, my mother still loved him and wanted her children to keep a good relationship with their father. Tiffany, our new step mother didn’t want anything to do with her step children. She snubbed and tended to look down her nose at my sister and me. My sister Amy absolutely loathed her, my mother never said anything about Tiffany, but my sister and I knew she would gladly kill her if she had the chance and a way to get away with the crime.

My father died of a heart attack when I was 19. His will had left trust funds for Amy and me that covered college expenses, gave us an allowance while in college. And enough for a starter egg after college. Tiffany got everything else.

My sister and I heard my mother cry at night, even with all the rotten things Dad had done to her, she still would have taken him back. She still had their old wedding and vacation pictures scattered around our small home.

I heard thru friends how Tiffany referred to my mother as “big old lumpy cow.” I wanted to make her cry like my mother had cried, I wanted her to hurt and suffer. I waited till I was 21 and received the rest of my trust fund before I decided to take some revenge for all the pain she had caused my family.

I began to follow Tiffany around, I learned she worked out twice a week at a gym, she had her own personal trainer, went to the hair salon once a week, when her maid came by to clean, etc. I had a key to my father’s house, he had given one to my sister and me after they had bought their new home. He wanted us to drop by and spend time with him and Tiffany.

I entered her home while she was at the gym, she had never had the locks changed not had she had the alarm code reset after my father’s death. I searched her house and room very carefully, making sure anything I moved was set back in the exact location it was before. I went thru her lingerie, I found a small slender vibrator in her night stand, I found her birth control pills and went thru her medicine cabinet.

I shopped for the items I wanted and bagged them for later use. I told my mother and sister I would be going on vacation hiking out west, I wouldn’t have a cell phone signal where I would be camping.

I chose Tuesday as the best time to begin my project; her maid came in to clean that day and wouldn’t be back till the following Tuesday. I knew Tiffany would be getting a manicure and pedicure that day. I took my bag of goodies, a pizza and let myself in the house. I took care of internal chores first, disconnecting the phones, etc. I went the laundry room next to the garage and settled down to wait. I heard the garage door open, her car drive in, and the garage door closed.

I peak thru the laundry room door crack as she entered and punched in her alarm code. When she turned and started to walk into the kitchen, I sprang out of the laundry room and slipped a large heavy duffle bag over her head and drew it down over her arms. I wrapped duct tape tightly around her body, trapping her inside the bag. I picked her up over my shoulder, wen to her bedroom and threw her down on bed. I was glad I had inherited my size from my mother’s side of the family; my father had only been 5’ 9’ tall, while I was 6’2”.

I had tied ropes to the bed post earlier; I rolled her on her back, sat astraddle of her stomach facing her feet. I got a rope end from the foot of the bed and wrapped it around her ankle twice, then tied it in a knot. She was fighting me and trying to yell, but the duffle bag and duct tape had her arms secure, plus her yells were muffle by the thick heavy bag. I grabbed her free foot, pulled it over wide towards the other bed post and tied that foot down.

I got up, turned to face the head of the bed, sat back down over her stomach. I got the duct tape, lifted her head and began to wrap it around her neck, I only wrapped the bag tight enough to prevent it coming off until I was ready for that. I wanted her to be unable to see anything. This would help terrorize her and add to her fears. I took her left arm, it normally being the weaker arm. Bent it back to the top bed post, I used a slip knot to tie her left wrist. I rose up enough to use a knife to cut the duct tape around her body. I dropped the knife seized her right arm and forced it up to the corner of the bed. I tied this knot more securely. I untied her left wrist, drew that arm up and retied it.

She was crying and begging me not to hurt her, she offered me money and her jewelry if I would take it and leave. I had not spoken or uttered a sound. I took my knife and began to cut her clothes off.

I dragged the cut and ripped clothes off her lower body, she was a real babe for sure. I sort of understood why my father had to have her. She had a perfectly shaven pussy, I assume she had it waxed, it was totally void of any hair.

I put my hands on her knees and very slowly slid my hands up her legs. I turned my hands down inside her thighs as they rose higher. She was crying now, she knew money and jewelry wouldn’t save her from being raped. When my hands was right up almost touching her pussy, I began to knead my fingers on her thighs, I was forcing her to acknowledge her attacker was deliberately taunting and teasing her. I removed my hands from her thighs and waited till I felt her began to relax. I bent back my middle finger, held the tip back with my thumb, then thumped her as hard as I could right on her clit.

She screamed and bucked her hips up, trying to break free. I thumped her hard several more times till her clit was turning a dark red. I left her, went to get some water and left her waiting all tied up and helpless, unable to see anything.

Tiffany still had on her blouse and bra, plus the duffle bag had her upper half covered. I retrieved my bag of goodies and spread them on the bed near her waist. I crawled over her to reach for the night stand, I opened the sliding drawer and removed her small Slim line vibrator. I turned it on so she could hear the buzzing sound. I pressed it to her head hard enough she could feel the vibrations and drew it down her body and left it lying on her mound.

I left it there for a second, picked up a big 10” vibrator that had a 2” diameter. I dangled and teased her pussy and clit with her Slimline model. I used my fingers to open her slit and rubbed the Slimline up and down her slit a few times. I lay the Slimline down and picked up the big vibrator, turned it on slow where it wasn’t as loud as the Slim line. I held her pussy lips apart, aimed and lined up the big vibrator tip to her pussy.

Tiffany was expecting her small slender vibrator to enter her pussy, she wasn’t wet, but she was used to the small one. Jack pressed the big model in her pussy lips and kept pushing. At first, she thought maybe she was dry or the tip wasn’t lined up right, then it dawned on her, this was a different vibrator.

Tiffany felt her pussy lips being pulled apart, her entrance was being forced to open wide to accept the invasion of the big rumbling monster. She began to moan and scream as it began to split her pussy; opening and stretching her hole till she thought she would be torn down there. She felt the vibrator going in deeper and deeper, pushing her cervix up when it reached the end of her sheath. It went in deeper till she felt like she was bursting.

The vibrator stopped when it was buried all the way inside her. Jack left it buzzing and vibrating inside her overfilled pussy. Jack left the big vibrator in Tiffany for maybe 10 minute while he had gone down stairs. Jack hid her cell phone, purse, and car keys.

Jack returned to the bed room, picked up the Slim line vibrator. Jack greased and lubed it with some KY jelly. Jack lifted Tiffany’s hips and began to press the small slender vibrator in her ass. Tiffany screamed and begged him not to do that, please don’t do that. Jack pressed and felt her sphincter open, once the tapered vibrator head slipped inside her anal ring, it glided right in her ass. Tiffany’s hips had lifted from the bed, she had tried to clench her butt to prevent the vibrator from entering her, the tighter she squeezed her butt, the more it hurt, she relaxed as much as she could and felt the burning searing pain recede somewhat.

Tiffany’s pussy had gotten used to the big vibrator by, her body had begun to respond to the intrusion and had started to get moist. She felt even fuller with the other vibrator in her ass. Her ass wasn’t hurting near as bad as when the vibrator had been forced in at first. She had heard some of her friends talking about anal sex, how it could hurt and yet feel good. She was beginning to understand the “Feel Good” part.

Jack took the knife and slit the duffle bag open up to where he had tape wrapped around her neck. He cut her blouse open, lifted her bra in the center between her breast. He cut her bra apart there and cut the straps going over her shoulders. Jack pulled the blouse and bra out from under her body.

Jack leaned over and began to very gently lick around her big breast. He didn’t touch her nipples or the pink flesh around her nipples. He did stop to blow very gently over the nipples, he saw little goose bumps build on her flesh and her nipples began to pucker. Jack had one hand laying over her mound, he slipped a finger down into her slit, located her clit and began to stroke his finger tip over her clit.

Jack looked between her legs, she was beginning to ooze a little moisture out around the big vibrator. Jack began to lick around her areolas. He felt small tremors as she was responding to all the forced stimulations. Jacked rubbed a little bit faster, still not pressing down on her clit at this time. He blew over her nipple and barely touched it with his tongue.

Jack made small circles over the tip of her swelling nipple, both nipples were becoming erect and standing up. Jack had to admit to himself, she had a fantastic body.

Jack finally lowered his head and sucked on her nipple, he didn’t bite or tug on it, he just sucked easy on the hard nub, he ran his tongue around the protruding tip.

Jack moved and shifted his body till he was lying between her legs. he began to suck and lick on her clit. Jack started to move the big vibrator out and back in. Tiffany was beginning to move her hips, tilting her pelvis up to lift and open her pussy.

Jack sucked harder and faster on her clit, he began to tug it with his lips and lashed it with his tongue. His hand was working the vibrator faster now, almost pulling it free, and then driving it back in deep.

Tiffany had moaned lightly at first, now she was beginning to pant and gasp, she felt a gathering of muscles deep inside vagina tighten up, heat was building rapidly inside her blood. Her clit had swollen from the thumping earlier and seemed more sensitive to the tongue and lips that was licking and sucking on it.

Jack managed to get his other hand down under ass, he gripped the Slim line and began to pump it in and out of her ass in tempo with the vibrator in her pussy. Tiffany moaned loudly now, she was getting so close, her pulse was pounding, her breathing was more huffing and puffing as she tried to suck air in.

Jack pulled both vibrators out and turned them off. He got off the bed and backed away from Tiffany. Jack stood still and watched her; he was also highly excited but he had to force himself to maintain control right now.

Tiffany was in a quandary, she had been so close to having an orgasm, now she felt empty and was wondering what would happen next. She hadn’t wanted him to stop at this point, she was too close and she was so horny. If he touched her a little more, she knew she would cum. She hated getting this excited and so close to cumming; even though it had been forced on her, only to have the orgasm delayed.

“Tiffany, how does it feel now?”

Tiffany tried to analyze the question and the voice. She wasn’t sure how to figure out the question, but she thought she recognized the voice. He had sounded familiar, someone from her past? She wanted him to say something else, she couldn’t comprehend the question. She hoped she could identify the person by his voice if he spoke some more.

“Who are you? What do you mean, “How does it feel now? Talk to me, explain the question.”

“How does it feel to almost cum, to be feeling so close to orgasm; only to have the stimulation and good feelings taken away so sudden?”

Tiffany searched her mind; she knew that voice from somewhere. Hopefully a name or face would come to her. “It isn’t nice to get someone this close and just stop. That is a form of torture. I assume you realize that and are doing this on purpose.”

Jack turned on the vibrators again and reinserted both. He had no problem getting them both in this time, she was still very wet; her pussy was open and her ass had learned to accept the vibrator. Jack worked both vibrators in and out and began to suck her clit again.

Tiffany knew what to expect this time. She tried to fight off the orgasm that was building inside her. Jack was working them harder and faster than he had before, he was forcing her to respond to the toys. She had no choice in accepting or rejecting what her body was feeling. Tiffany was getting more aroused regardless how much she tried to fight off her responsive feelings.

Jack pulled out the slim line form her ass and sank his middle finger in deep. He massaged her ass deep inside with his finger tip. Tiffany’s hips began to buck, this was far more stimulating than the little vibrator. Fire was beginning to race thru her, she hoped she came before he stopped this time.

Jack had felt her sphincter clamp and squeeze on his finger, he knew how close she was. He pulled his finger out and withdrew the big vibrator at the same time.

Tiffany wanted to scream, it just wasn’t fair, she was hurting a little bit now from this form of torture. “How does it feel now Tiffany?”

Tiffany was mad at herself, she knew that voice but still couldn’t place and name or face to the voice. “It hurts, is that what you want to hear me say? It hurts to get so close then have you stop all of a sudden like you are doing. Does that make you happy?”

Jack repeated the sequence 2 more times, building her up to almost having an orgasm, then stopping and to repeat his question. Tiffany had started to cry now. She was in pain from being brought so close to release only to have her orgasm stolen away.

“This time, I will allow you to cum. I won’t stop till you beg me to stop.” Jack inserted the big vibrator and his finger. Her ass was much more accepting caresses from his probing middle finger than the small plastic vibrator. Jack was true to his words, he let Tiffany cum this time. Her juices were running out of her pussy with every stroke of the big vibrator. Her ass was going crazy squeezing and trying to milk his buried finger. Jack continued to suck and pull on her clit, he kept on pumping the big vibrator in and out, his middle finger was crooking and massaging her ass as deep ass as his finger could reach.

Tiffany had multiple orgasms; she came over and over for 4 or 5 minutes with only ripples of rest between them. Her pussy and ass was beginning to burn now, her mouth was very dry from all the huffing and puffing she had done. “You can stop now.” Jack kept on pumping, licking, sucking, and fingering her ass. Tiffany had another orgasm, this time it hurt, her inner muscles felt sprained from all the contractions and quivering, her pussy and ass was beginning to feel raw. “Please stop, I am begging ok, please stop, please.”

Jack stopped and pulled out the big vibrator and turned it off. “How does it feel now Tiffany?”

Tiffany was crying again, “It felt great at first; I never came so much or came so hard in my entire life. Then I began to hurt from cumming over and over. I feel sore, my pussy and ass feels raw, I am burning all over down there. Why are you, why are you doing this to me?”

“I am your new master Jack.” Jack cut the tape holding her hood in place and removed the duffle bag. Tiffany lay there staring at Jack, was this some kind of horrible joke? What was he thinking, had he gone crazy?

Jack sat down where Tiffany could see his face. “I am doing this for several reasons Tiffany. You stole my father from my mother and sister. You hurt my family and me, I am hurting you in return.”

Tiffany looked at Jack, he looked sane, didn’t appear to be on drunk or on drugs. “Why are you doing this to me, why have you stripped me and molested me? This is rape, even if you haven’t fucked me.”

“Tiffany, you used your looks and your body to steal my father. You have used your beauty and your sex to get what you want. I am claiming you because you need to learn how to serve rather than to be served. As to what you just said a moment ago, I haven’t fucked you, but now I will. You will learn how to serve me, to do whatever I tell you to do. You will learn how to suck my cock, how to fuck me with your tits, pussy and ass. You will call me Master from now on.”

“Oh my God, you are crazy Jack, you have lost your fucking mind,” Tiffany was scared, he was crazy.

Jack slapped Tiffany across her breast until they turned red, “I told you to call me Master.” Jack stood and took off all his clothes, then climbed between Tiffany’s legs, took his cock and pushed it in her pussy. He began to fuck her, he was taking his pleasure on her, not trying to please her or let her enjoy the act. Her pussy was still sore and burning from the big vibrator and repeatedly having it forced in her. Jack groaned and swelled, then jammed himself in her as deep as he could and came. His cum did feel soothing to her sore pussy.

Jack pulled his cock out and told Tiffany, “Go to sleep and rest, you have a long hard week ahead of you. Your training has just begun.” Jack reached down and got a set of ankle cuffs, he fastened one to her ankle and was preparing to snap the other cuff to the bed post knob.

“Jack, wait a minute please, I need to use the bathroom.” Jack slapped her breast harder and pinched her nipples. Tiffany screamed and begged him to stop hurting her.

“You just called me Jack. You will learn to listen to me and to obey any commands I give you.” Jack was slapping her breast, turning them a bright red.

“Master please stop hitting my breast, please stop hurting me. Please let me use the bathroom.”

Jack escorted Tiffany to the bathroom, he led her to the commode and told her to piss.

Tiffany was stunned, he expected to pee while he stood next to her and watched, he really was crazy. Tiffany sat on the commode; it was hard to get her urine to start flowing, knowing he would hear her piss splashing in the bowl She finally peed, wiped herself and flushed the commode.

Jack said he needed to pee too, he told her to hold his cock and aim his stream at the bowl. Tiffany refused to do this, he could hold his own damned cock if he had to piss. Jack grabbed her nipple between his thumb and index finger, he squeezed and dug his thumb nail into her nipple. Tiffany screamed and tried to twist free.

“Tiffany, take my cock, aim my piss in the commode. If I have to tell you again, you will be punished severely. I am your master and expect to be obeyed, you will learn to any and all my commands.” He squeezed harder, her nipple was about to burst open. She held his cock until he was done pissing. “Shake the end to make all the drops come out.” Jack released her nipple.

“Come with me to the kitchen, I brought in a large pizza.” They ate half of the pizza, he allowed her to have a glass of water. Jack took her back upstairs and told her to lie on the bed spread eagle on her stomach. Jack tied her ankles and wrist to the bedpost.

Jack pushed her pillows under her lower stomach pushing her hips up. “Tiffany, as I fucked you earlier, you just laid under me, you didn’t move and try to please me. You have to learn your only function is to please and serve me.”

Jack lay between Tiffany’s legs and pushed his cock into her pussy. “I am going to hold my cock in you, you are to fuck your hips up and back, you will move and fuck me with your pussy or you will be punished.”

Tiffany began to push and rock her hips back, she felt Jack’s cock going in and out only when she moved. He was supporting his weight on his knees and elbows, she was having to do all the work. Jack pulled his cock out of Tiffany’s pussy. “You aren’t trying to please me Tiffany, you are only doing the bare minimum to move your hips. You aren’t moving to make my cock slide in and out in long strokes, you have to concentrate on giving me maximum pleasure. Try again, make me cum hard in you.”

Jack put his cock head over her asshole and began to push. Tiffany screamed as his thick head forced her ass to open wide, she felt her anal ring stretch as he pressed in and in. He was splitting her ass open, she was being ripped apart. Her ass was on fire and burning terribly as Jack went deeper and deeper into her bowels.

Jack was still supporting himself on his knees and elbows, he was giving her room to move under him. “Relax your ass Tiffany, stop clenching your asshole so tight. You will find it easier on you if you quit squeezing me and push your ass up.” Tiffany had nothing to lose, she was hurting so bad, maybe if she tried what he said, the pain wouldn’t be so bad.

Tiffany stopped trying to push her hips down on the bed, as she lifted her bottom up, she felt her asshole relax and stop squeezing down so hard on his cock. While her pain was greater reduced, she was still hurting bad. She knew he wouldn’t remove his cock until he had cum in her, the faster he came, the sooner he would remove his large cock from her poor ass.

Tiffany pushed up and moved her hips back down. She learned it didn’t hurt as much if she moved her ass in small circles when pushing up onto his cock or dragging his cock out on her downward movements. Her ass was still burning, but she felt another heat building in her pussy. She wished he would reach under her and rub her clit, she thought she could cum and ignore the pain in her ass.

“That is better Tiffany, you are learning to please me. Move your hips faster, try to take me deeper on when your hips are pushing up.” Jack’s cock was longer and bigger than his finger, it was rubbing her deeper, filling her and allowing her to feel more pleasure now than his finger had given her.

Jack felt her change the way she was fucking his cock, she was arching back hard, slamming his cock hard and deep up her ass. His balls were drawing up tight, he was going to cum. Jack squeezed down on his cock, trying to hold back and delay his shooting off in her ass. The longer he could wait, the more intense his feelings would be. Tiffany felt drops of sweat falling on her back, she knew Jack was ready to cum, so was she.

Jack pushed down hard into Tiffany, he drove her ass down till she was lying on the pillows under him. Jack felt his balls pulse and contract as they spurted cum deep inn her ass. His hot cum flooded her bowels, she felt his heat filling her. She squeezed her ass, trying to milk him of every drop when Jack pulled his cock out of her ass.

Tiffany was so close, her asshole was still gaped open, she knew her hole was still spread. “Oh Master, please, I am so close to cumming. Put it back in and let me cum.” Jack was pleased, she had done better pleasing him this time. He liked how she called him Master, how she had begged him to put his cock back in her ass and allow her to cum. Jack slid his cock back in he ass, his cum and her open ass easily allowed him to sink in. Jack began to pump his cock in her, Tiffany screamed when she came.

Jack pulled his wet slimy dick from her ass. He hole was open, he could see his white sperm bubble and ooze from her ass. He reached down into her ass and dipped his fingers in her hole. Jack pulled out some cum from her ass and massaged it around her open hole. “You have a lot to learn Tiffany, that was much better. I allowed you to cum because you pleased me. I am in control, I will tell you when you can cum, I will allow when you please me, I will deny you pleasure when it please me.”

Jack got up and left the bedroom. He went down to the basement and screwed in some large hooks into the floor joist beams. The was a large heavy table along one wall, his father had used it for some of his wood working projects. Jack screwed hooks on the legs near the floor, he screwed more hooks into the wall over the table. He was preparing for the next step in training Tiffany.

Jack went back upstairs to where Tiffany was still tied down. She asked him to let her use the bathroom again. His cum had lubricated her bowels, she needed use the commode. Jack untied her followed her to the bathroom. She sat down and felt a rush of liquid shit gush from her ass. Her face turned red, she knew Jack could her bowels empty. She wiped herself clean and flushed the coomode.

Jack told Tiffany they needed to shower, they both stank and her pussy smelled funky from his spent cum. He adjusted the shower and made her stand in front of him. He played with her tits and fingered her pussy from behind. Jack told Tiffany to turn facing him and to kneel at his feet. Jack placed his cock to her lips, “Suck it, make me cum and don’t spill a drop of my cum, swallow all of it.”

Tiffany had no choice, she thought of biting him, then thought of what he would do to her if she did that. She opened her mouth and took his head in her mouth. Tiffany kept her mouth opened and bob her head back and forth on his cock, this had been the way she had done this before when she had to. Jack told Tiffany she had to do better, her blow job skills were terrible. He made her licked his head and shaft, he had her curl her tongue and lick the little hole in the end of his dick. When he felt ready to cum, he had her take him in her mouth and rub his balls. Jack wrapped his hands around the back of her head and pushed his cock as far as it would go, he felt his cock slip over her tongue and slide down her throat, He came in her throat, spurting his cum directly to her stomach. Jack pulled his cock out, she was choking and gasping, she hadn’t been able to breath with him blocking her throat.

Jack took Tiffany back and tied her to the bed again. He lay beside her and the both slept. The next morning he took her to the bathroom. He didn’t allow her to piss but had her get in the tub on her hands and knees. Jack had the shower temp adjusted to his liking. He got in the tub behind her and showed his cock in her pussy. Jack fucked Tiffany hard and came in her. He stayed on his knees behind her with his cock still buried in her pussy. Jack waited till his cock softened up, then began to piss in her pussy. His hot stream of piss washed her pussy aand made her begin to piss. Tiffany was amazed how good it felt, it was filthy and disgusting, but it did feel good. Jack pulled out before she could cum. They stood and he made her wash, then soap and wash him.

Jack led Tiffany downstairs and had her cook breakfast while standing naked. He admired her figure, she was so sexy standing in front of the stove with her womanly hips and ass showing. Jack ate and made her clean the table off. He told her to lie on her back on the table.

“I am going to eat your pussy and suck your juices. I may finger your ass and pussy, but you will not cum unless I give you permission.” Jack sat down in the chair, raised her legs up and placed them over his shoulders. Jack pulled her to the edge of the table and began to lick her and tease her.

Tiffany felt Jack’s tongue roll and stab in her pussy, he began to fuck her with his tongue. He used a finger to tease her between her pussy and her ass, then began to rub her juices around and over her asshole. Tiffany was feeling so good, Jack was pushing her into an orgasm, she knew she wasn’t supposed to cum, but the feeling was just too strong. She came and came.

Jack stood and pulled Tiffany off the table, dropping her to the floor. “I told you not to cum unless I gave you permission. You didn’t even ask me to allow you to come.” Jack reach down, grabbed Tiffany by hr arms and lifted her to her feet.

Jack pushed Tiffany in front of him toward the basement door. He made her walk down the steps to face the large work table. Jack pushed Tiffany into the table and reached for one of the ropes he had tied to the wall screws over the table. Jack drew her arms up high until she was standing on her toes and tied her hands to the wall.

Jack spread her feet out and wider than her shoulders and tied them to the table legs. Jacks father had some wooden dowel rods he had used on one of his projects. Jack chose one of the smaller dowels and slapped Tiffany across her ass cheeks. Tiffany screamed, the dowel rod had left a red streak across her bottom, but it had broken on the first lick.

Jack went upstairs to her room, het removed the leather belt from his pants. Jack walked back to the basement. Tiffany was crying, she was hurt, but she knew she would be whipped and hurting before she left this room. Jack stood behind Tiffany and chose where he wanted to mark her ass. He swung the belt, it’s smack was followed by a scream from Tiffany, the belt hurt much worse than the dowel rod did. Jack aimed and made the next lick land at an angle from the first lash of the belt. Tiffany’s ass a red X across her cheeks.

Tiffany screamed, the belt was leaving red raised welt on her ass. Tiffany heard Jack talking to her, “Repeat that after each blow; I can only cum if my Master allows it. I will not cum without my Master’s permission.”

Jack drew back the belt and gave her a whack on her upper legs just under her ass checks. Tiffany screamed and sobbed out ”I can only cum if my Master allows it. I will not cum without my Master’s permission.” Jack reached in between her ass cheeks and drew a finger up her slit. Jack’s next lick was just lower than the last, Tiffany was crying and trying to speak as commanded by her master. After each lick, Jack would listen to her repeating his command and stick his finger in her pussy. By the 8 ^ th lick, Tiffany was getting wet, by her 10 ^ th lick, she was dripping.

Jack began to finger her pussy and rub her clit, “Would you like to cum Tiffany?”

“Please Master, allow me to cum, give me permission to cum.” Jack rubbed her pussy, he loved how her juices was now dripping on his hand. Jack pulled his fingers out and moved them to her lips, “Suck your pussy juices from my fingers. Taste your leaking cunt.” Tiffany was a bit hesitant, then remembered hw the belt had burned on her ass and legs. She sucked her pussy juice from his fingers. Jack pumped her a few more times and offered her his fingers, she sucked them clean with no hesitation.

“You are learning to obey and that pleases me. I will allow you to cum on my cock.” Jack stepped in closer to Tiffany; she arched her back and thrust her hips back. Jack pushed into her wet pussy and allowed her to fuck him till she came. He warned her not to stop, he hadn’t cum yet. Tiffany kept fucking back hard, waiting for Jack to cum. She had other orgasms, the pain and the fucking was overloading her brain. Jack pulled his cock from her ass, shoved it in Tiffany’ ass and came.

Jack untied Tiffany and took her to the bedroom. Jack re-tied her on her back spread eagled. Jack left her and went down to get her cell phone. He scrolled her contact’s list and found the number to the gym. Jack called the gym and told them Tiffany needed to cancel her appointment with her PT, she had been called out of town on an emergency. She would contact them when she got back next week.

Jack spent Thursday and Friday training Tiffany, he rewarded her with an orgasm when she pleased him and punished her when she hesitated to follow his commands. Her biggest whipping had come when he ordered her to lick his asshole. She refused to do this; Jack whipped her on her bare pussy while she was spread eagled on her back. After a few lashes with his belt on her clit, she licked his ass.

Jack soon learned Tiffany would deliberately break a minor rule to get a spanking. He would have her lie over his lap and use his hand to paddle her bare bottom, most of the time he teased and played with her pussy, she was always wet after the spankings. She would then call him Master and offer to please him. She had figured out that pleasing him allowed her to cum

Jack was only handcuffing her ankle to the bed post now, she lay however he ordered her to do, if he told her to spread eagle on her back, she would drop down in the center of the bed with her arms and legs spread wide.

Jack fucked her Saturday morning before allowing her to go to go pee. He made her cup her hand over her pussy and catch all her juice and cum in her hand. Tiffany licked her hand clean when he told her too. He allowed her to pee, she wouldn’t hesitate to hold his dick when he pissed. She even licked and suck the few drops of piss from his cock when ordered too.

Jack had Tiffany fix a big breakfast for both of them. After eating, Jack had Tiffany lie over his lap with her legs spread. He used both vibrators from behind, switching and swapping them until she had soaked his lap. Jack told her she could cum, Tiffany thanked her Master for giving her permission to cum.

Jack had Tiffany lie spread eagled on her stomach. He tied her all stretched out and turned on the big vibrator. Jack placed the vibrator under her, trapping it between the bed and her mound. He knew if she pressed down with her pelvis, she would be feeling the vibrator mashing her clit. Jack told Tiffany he had to go run some errands, he would return in a couple of hours. Jack told Tiffany she could cum as often as she wanted, she had his permission.

Jack left the house driving her car. He called his sister Amy to be quiet and listen, don’t speak till he told her something, do not let her mother know he was on the phone. Jack asked Amy if she could meet him at Starbucks, near the mall?

Amy was curious to find out what was going on, she had assumed Jack was out west hiking. She said she would be there in 25 to 30 minutes. Jack had ordered a regular coffee for him and a French Vanilla Latte for Amy. Amy came in while he was getting the cups over the counter.

They sat in a corner, she knew Jack had something he wanted to share in private. As soon as they had sat down, Amy asked Jack what was going on? She was dying of curiosity.

Jack smiled at Amy, “I have a slave.” Amy’s face twisted in confusion, was this a joke? Was her brother a pervert or a sex fiend?

Amy pushed back from the, she was about to walk out. “Jack, I don’t want to know any details about your kinky sex life. I am not into freaky far out sex.” She rose and turned to walk out the door.

“Amy, wait a second please. I forgot to tell you my slave’s name is Tiffany.” Amy froze, turned and sat down facing Jack. She leaned and looked into his eyes. She saw the smug grin on his face. She did not have to ask “Tiffany who?”

Amy did want details, she learned about Tiffany calling their mother a big lumpy cow. She learned how Jack had watched Tiffany and planned his “Project”. Amy was leaning over the table closer to Jack as he spoke, she was very interested in everything he was speaking of now. Starbucks was getting to crowded to talk about such a sensitive subject. Jack suggested they drive to Tiffany’s house and he would give her all the details.

Amy followed Jack back to their father’s house. She followed Jack to the kitchen, he had done some minor food shopping on the way to Starbucks. Amy made Jack tell her everything, how he had covered Tiffany with the duffle bag, how he stripped an broke her, the toys, pissing on her, making her tongue his ass, whipping her on the pussy, everything. Amy asked where Tiffany was now.

Jack told Amy to follow him upstairs, but not to make any noise. Jack opened the bedroom door, Amy saw Tiffany tied face down, she was moaning and wiggling her hips over the big vibrator, she had 2 orgasms while Jack was gone and close to having another one.

Amy walked to the foot of the bed and looked at Tiffany’s ass and pussy. Amy saw the wet sheets under Tiffany’s hips, she knew Tiffany had been having an orgasm. Amy motioned for Jack to follow her to the hall, she closed the door softly. “Will Tiffany do anything you tell her to do?”

Jack laughed, “When Tiffany gets hot, she will do anything and everything. She knows she will be rewarded with an orgasm if she pleases me.”

Amy looked at Jack, “Can you force her to lick my pussy and drink my juices if I cum in her mouth?”

Jack laughed, he knew Amy to humiliate Tiffany, thinking of that was making Amy horny. Jack had started to fuck his sister when she was younger. He had been her first, the one who took her cherry, the first to go down on her, the first to fuck her in the ass, and the first person she had given a blow job too. “She will eat your pussy, she will do anything you want her to do. Come on in and see if she doesn’t follow all our orders.”

Jack and Amy went in the room, “Tiffany honey, you have company.” Tiffany turned her head to see Amy and Jack standing watching her. Jack untied Tiffany’s hands and feet. “Come to the bathroom, you need to pee.” Amy watched as Tiffany rose and walked into the bathroom. Jack raised the lid and the seat. He told Tiffany to stand and squat on the rim, they wanted to watch her piss.

Tiffany was squatting on the rim with her knees spread, Amy was standing and watching, waiting to see what would happen next. “Tiffany, I want you to piss now, Amy wants to see you piss.” Tiffany strained a bit and her stream began to spurt out to fall in the bowl. Jack turned to Amy, go get ready, we will be in there in a minute. Jack allowed tiffany to wipe her pussy and flushed the toilet. He told Tiffany to bend over, he probed her pussy with his fingers and teased her ass.

Tiffany and Jack left the bathroom; Amy was lying in bed with pillows under her hips, her legs open. Her pussy was already wet, she was excited by having Tiffany forced to eat her pussy. Jack told Tiffany to get on the bed between Amy’s thighs and to raise her ass up higher, and to spread her knees on the bed. Jack stripped off his clothes and got on the bed behind Tiffany, he eased his cock head barely into her pussy.

“ Tiffany, licked Amy’s pussy, she has a horny pussy that needs to cum on your tongue. Make her cum and swallow every drop of juice that runs out her pussy.

Tiffany had never eaten a pussy before or had a woman eat her pussy, but she knew what she like when a man ate her. She licked, sucked, fingered and teased till Amy was screaming and crying in a wild orgasm. Jack had begun to fuck Tiffany, watching his sister getting eaten by Tiffany was making him horny. Jack stopped fucking Tiffany and pushed her over to the side of the bed.

“ Tiffany, watch your Master fuck his sister.” Jack dropped down and into Amy. He fucked her and came in her pussy. Jack stayed in Amy till his balls had quit spurting. Jack pulled his dick out from Amy’s cum filled pussy and told Tiffany to lick her clean. Amy came several times as Tiffany sucked all of Jack’s cum and her pussy juices from Amy’s pussy. Jack had Tiffany lick his cock and balls clean.

“Tiffany, come lay across my lap.” Tiffany laid down over Jack’s lap, she knew she might receive a spanking or he might just tease her. Jack told Amy to sit and watch. Jack showed Amy the 2 vibrators, “Which one do you think Tiffany needs.”

Amy pointed to the big 10” model, “Give her that one up her ass Jack. I want to see her ass that that monster.” Amy didn’t know that Tiffany had taken the big one and the other one at the same time. Tiffany barely moaned as the big vibrator went into her ass. Jack slid it in deep and began to fuck Tiffany who was moaning and hoping Jack would allow her to cum.

Amy was rubbing her pussy as she watched Tiffany get fucked in her ass with the big vibrator. She was beginning to feel a little jealous, she wasn’t sure she could take something that big up her ass, but she was willing to try. Jack surprised Amy when he took the smaller model and began to fuck Tiffany in her pussy.

Amy crawled around on the other side of Tiffany and grabbed her hair. She pulled Tiffany’s head up and pushed her pussy to Tiffany’s face. “I am going to cum, eat me. “

Amy came back Tiffany’s ass after Jack told her to come back and watch. Jack put Amy’s hands on the bases of the 2 vibrator and told her to fuck Tiffany. “Tiffany, you will be allowed to cum soon, do not cum until I give you permission.”

Amy was getting exited again. Hearing her brother commanding Tiffany to wait and not cum was so fucking hot. Amy was jabbing the vibrators in as far as they would go and as fast as she could work them. Tiffany was crying and begging for permission to cum, Jack winked at Amy and smirked, “I told you she will do anything and everything. Tiffany, I will count to 10, when I say 10, you may cum, you may even have a multiple orgasm. 1 2 33 4 5 6 7 8 9 10.”

Tiffany screamed and screamed as she came, Amy had never seen so much juice in her life. She touched Tiffany’s pussy and coated her finger, tasted it, hmmm not bad.

Amy and Jack fucked and teased and used Tiffany until Amy had to go home. Tiffany could barely walk, she was fucked out. Amy wasn’t much better off that Tiffany, she had been able to take the big vibrator in her ass and both of them at the same time just as Tiffany had done. Jack asked Amy when she could come back, she said tomorrow morning. She was smiling when she said that, Jack laughed with her.

Jack left Tiffany tied spread eagled on her back when Amy got there, he needed to run out for a small chore, would Amy mind babysitting Tiffany. Amy laughed, she would love to be alone with Tiffany for a few hours. Jack said he would only be gone an hour.

When Jack returned, he found Amy on top of Tiffany, they were doing a 69. Amy had untied Tiffany’s hands, the girls were eating each other’s pussy and fucking the vibrators in each other’s ass. Looking at their shiny wet faces, Jack knew Amy had given Tiffany permission to cum. As wet as their faces were, Jack knew they had both cum several times each. Amy rolled off Tiffany, they both sat up side by side.

Jack laughed to see such a sight. “I went shopping and ought you a present.” Jacked opened a bag and withdrew a strap on harness with several rubber penises of different sizes, it even had a double dong dildo, one for the ass and one the pussy.

Jack told Tiffany he was proud of her, she had pleasured them both so well he would let her chose what she wanted, she could chose who fucked her in her pussy and who fucked her in the ass, she could even chose which rubber dick went in the strap on. Tiffany was surprised; Jack had never allowed her to make choices before. She chose Jack to fuck her pussy and Amy to fuck her in the ass. She chose the next to largest rubber dick for her ass, it was almost identical to the big vibrator.

Jack lay on his back and Tiffany moved over him, reached down and guided his cock into her pussy, Amy kneeled behind Tiffany and aimed the rubbed dildo up with Tiffany’s ass. “Master, will I be allowed to cum this time? Please Master, you and Amy make me so excited, please,?”

Jack gave permission for Tiffany to cum as many times as she could. Amy pressed the rubber dick inside Tiffany’s ass. Tiffany shuddered and squirmed, She hadn’t ever felt like this before, it was better than Jack’s cock and the big vibrator. Jack didn’t move, he just tried to lie still and let Amy do all the work. Jack could feel every movement of the dildo thru the thin tissue walls that separated Tiffany’s ass and her pussy. Jack felt Tiffany’s pussy squeeze him several times as Amy plowed her ass with the dildo. Tiffany had so many orgasms she could barely ask Amy to stop.

Amy pulled out the dildo and quickly unsnapped the harness, she wanted the same fucking Tiffany had gotten. Jack went in Amy’s pussy and felt Tiffany ease the dildo into Amy’s ass. Amy came much f=faster than Tiffany had, She had to stop after only a few minutes. Jack had Tiffany remove the harness. The three of the took a shower, Tiffany was kneeling sucking and cleaning Jack’s cock, then licked Amy to another orgasm.

They went downstairs and ate a late lunch. Jack sent Tiffany upstairs to bring down the harness and the largest dildo. The girls were slightly nervosa, this was a huge dildo, they were afraid they couldn’t take it and Jack’s cock too.

Jack told Amy to lie on the couch with a cushion under her hips, he pulled her ass to the end of the couch and wedged the cushion between her ass and the couch arm. Tiffany put on the harness with the biggest dildo in place. Jack told tiffany to fuck Amy in her pussy. The girls sighed with relief, they weren’t going to take on Jack and the huge dildo.

Tiffany worked the dildo in Amy’s pussy and fucked her slowly. She was surprised when Jack moved in behind Tiffany and slid his cock up her ass. Jack put his hands around Tiffany and began to play with her nipples. He whispered in her ear it was ok if she came, she had his permission. He told Tiffany to play with Amy’s nipples as h they shared a three way fuck. Amy came first, the biggest dildo had hurt at first, but she knew she just had to take the monster in her pussy. Tiffany came when she heard Amy cum. Jack came because he was excited seeing his little sister take the big rubber dick, plus Tiffany’s ass was as milking his balls. The girls swapped positions.

Tiffany asked her Master is she would be allowed to come again when Amy fucked her. Jack laughed; Tiffany was making a damned good slave. He gave her permission to cum.

Amy’s ass was rounder and fuller than Tiffany’s ass, Jack had only fucked her a few times, but the vibrators and all the exciting fucking had her easier to get into. Jack finally came in Amy’s ass. Tiffany licked and sucked Jack’s cock and balls clean and licked his cum from Amy’s ass.

They were sitting on the floor resting, Amy had to go home soon. “Amy, what do you think of my new slave now?”

“Amy smiled at Jack and Tiffany, “I think she is a keeper Jack. You are a lucky man.” Amy dressed to go home.

Tiffany crawled across the floor to Jack and began to lick and suck his cock. “Master, it is permitted for this slave to kiss you and thank you?”

Content

Nickel Mann
Training Step Mom