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Tiffani's Struggle Chapters 1 and 2

Tiffani's life is complicated, and filled with lust as she struggles with the choices she makes.

1.

Tiffani and Dean had been together for three years now, one year as a “vanilla” couple spending much of our time trying to figure out what we really wanted with each other, one year living a more experimental lifestyle while away from each other with work obligations, and the last year married with her being his complete submissive. Dean had spent a lot of time guiding Tiffani through her sexual exploits, opening doors she never knew she had, and he was so proud of how far she had come.

When he retired from his company, they made the decision that she keep going in her career, she did just get promoted to a high position in her company and was six years younger than him. So Dean became the stay at home husband while he looked for other career opportunities, but it didn’t change their relationship in anyway. Whenever she was on his arm she knew whose property she was, and she obeyed completely after the last year of training. When she came in the door from work she would immediately go to the bedroom and remove her work clothes replacing them with the clothes Dean laid out for her, and generally there was one of their many toys for her to use as well.

Tonight was the eve of a special occasion, he had laid out a cup-less black lace bra, matching crotch-less panties, some thigh high fishnet hose, and a grey cotton pajama set to wear over it. She was allowed to wear the PJs from time to time until they started play time, and then she could only wear the undergarments as instructed. As for her toy, he had picked out a remote controlled number this time, it was a unique one, there was a nice large vibrating G-spot stimulator, with a piece that laid on top of the clitoris, and a rubber cord attached to a medium sized vibrating anal plug. He had spent forever trying to find this particular toy to stimulate all of her at once, and there were a multitude of settings allowing him to vary the pleasure she received immensely.

Tiffani came walking out of the bedroom just like every night, and Dean looked at her with a little smile, she had been such a good girl and he was so proud of her. She walked over to him kneeled down next to where he was standing and simply said, “would you like for me to start dinner now Master?” He looked down at her and felt such pride when he noticed she was even wearing her red collar with the black tag which read “SLUT” just like she had been trained for the past year.

“Yes Tiffani, dinner needs to be done in one hour, and you will need your sleep tonight, we have big plans tomorrow.” Dean was sure she had been paying attention to the calendar he had put in the play room two weeks ago, he had put up a nice little calendar with one date circled and one thing written, “Graduation.” This isn’t your typical graduation, she was graduating from her training position to her full time position as his submissive, things would change from here. Tiffani handed Dean the remote, and gave him a kiss, their lips grazed each other, tongues darting out and into each other’s mouth. Her lipstick smearing on both their mouths, and sparks of unadulterated love shooting through their bodies.

Dean lost his train of thought for a brief moment, and when he focused again he saw the smile on her face, she knew she still made him week in the knees and lose all control. Dean enjoyed the power she held over him, but he couldn’t have her getting any crazy ideas this close to the end, “Did you enjoy that?” he asked. Tiffani looked at Dean, and with a smile on her face as she began to bow her head simply stated, “Yes Sir.” He clicked the button on the remote just as she was speaking so that it turned from a word to a small moan, and he watched her knees buckle slightly. With a smile he told her, “Now cook my dinner, slut.”

Dean watched as she walked over to the stove on uneasy legs, the vibrations rumbling through her body, intense sensations rocking her clit, inside her cunt, and through her tight little asshole at the same time. She was almost to the stove when he turned it off, the look of disappointment and relief on her face made him laugh a little bit. Dean had been planning these two days for as long as they had been in the contract, what she didn’t know was dinner was being delivered and her fun was going to start a little early.

He watched as Tiffani began to pull out pots and pans and when the doorbell rang he told her to get the door, as she opened the door and saw their friend standing there she said hello and then looked at Dean confused.

“Come on in Scarlette, it’s always a pleasure to see you,” Dean said.

“I just wanted to see if you two had dinner plans, Ethan and I are going to head into the city later on and we thought we would invite you,” Scarlette said as she moved into the foyer and stood with her head bowed like she always did in Dean’s presence. Scarlette and her husband Ethan enjoyed the same lifestyle as they did, and they played a lot of scenes together. Ethan happened to be Tiffani’s second favorite fuck, his cock was slightly bigger than Dean’s and he was a little crueler, but he still never did anything without Dean’s permission or supervision.

“No, thank you Scarlette, I have already taken the liberty of ordering a light dinner for the evening,” Dean said. He could see the look of disappointment and excitement on Tiffani’s face, she loved the company of Ethan and Scarlette, but whatever Dean had planned for her would undoubtedly be great. Dean told Tiffani that she and Scarlette could speak freely with each other if they would like while he went to check on a few things in the other room.

Dean and Tiffani met Ethan in Crete, Greece while they were both working out there, he had been the first person to join in on their fun. After they left Ethan kept messaging Tiffani, with Dean’s permission of course, by the time Dean was retiring his business had brought him to their location. When he got there and they rekindled their connection Tiffani and Dean had already found their first girlfriend, Scarlette. She lived with them, just like one of the family, and Tiffani had wanted her to be his submissive too. Dean always wanted another submissive but he was trying to wait until Tiffani was fully trained, she promised him she would be a good girl if he would do it. So after a while Dean agreed and they began an exciting life of the three of them. They would swap in and out all the time, sometimes he would allow Tiffani and Scarlette to play with each other while he watched and sometimes Dean would fuck Tiffani while Scarlette watched, and vice versa.

When Ethan came over to visit, Dean introduced him to Scarlette not thinking they would actually hit it off, but just to let him get to know their newest member of the club. Ethan wasn’t around when Tiffani and Dean started their Dominant/submissive relationship, the last time he was with them they were just into crazy sex. Everything was a lot more structured now, but still crazy as shit.

Ethan was there the last night they were in Crete, Tiffani and Dean had gone to the strip club and met up with Ana, her favorite stripper, and went up to the VIP room. When they got up there they were both completely drunk, Dean sat down on one couch while Tiffani sat on another. Ana got on her knees in front of Tiffani and they began to kiss, soft at first but as they went on their tongues started to dance with each other, hair started being grabbed, and Tiffani’s breasts where pulled from her shirt. Ana sucked on her nipples and pinched each one until they were red and perky, little moans escaping Tiffani’s mouth with each pinch. Ana had undone her pants and was reaching into her already wet panties, Tiffani was pretty drunk and nervous about their location but she was trying to enjoy it as best she could. Ana was slipping her finger in and out of Tiffani’s tight pussy over and over while kissing her and looking in her eyes until she threw back her head in orgasm.

It wasn’t her best orgasm, that title still lied with Dean, and he doubted it would ever change. Dean was not a complete jerk he just knew his shit was that good. He told them to switch and in a flash Tiffani had pushed Ana back on the couch and began finger banging her used cunt, he could tell Tiffani was not enjoying herself to the fullest and since it was their last night he decided to call it and head back home. Dean wanted to make up for what happened so he called Ethan while they were walking and told him to meet them at their room.

When they got there Tiffani was a little tired and very drunk, she wanted to go to bed, but he had learned early on in their relationship that her body belonged to him and if he said they were fucking then that is what they did. Dean went to the bathroom, where Ethan was hiding and waiting, but when the two men came out Tiffani had slipped out of her clothes and was drifting off to sleep, he looked at Ethan and said “She’s all yours man.” With a smile on his face, not a pleasant one, at least not pleasant for the person on the receiving end, he stepped forward and pulled out his impressive cock. Dean’s cock is larger than most, but Ethan’s is thicker and longer, his dick is so large sometimes he has a hard time being fully erect but no one has complained yet. He walked over to Tiffani who was laying on her stomach with her feet hanging off the edge of the bed, he took some of the KY Dean always had on hand, and he poured a healthy amount on the tip of his prick and began to rub it up and down his shaft.

Ethan looked at him one last time and asked “Are you sure you’re good with this bro, I’ve never done this while she was sleeping?”

“Don’t worry, once you slide that meat stick of yours into her she won’t be a sleep anymore,” Dean replied.

Ethan reached down and grabbed Tiffani by the ankles, pulling her to the edge of the bed, she woke up and looked behind her and smiled. He looked at Dean and was given a nod to go ahead, so he rolled her over and she opened her mouth and moaned, “daddy”, she didn’teven notice it was Ethan and not Dean. She arched her back while allowing her legs to be lifted up, Ethan spread her legs apart and let out a little groan at the sight of her gorgeous slit. He leaned over Tiffani, putting her legs his shoulders, and whispered just loud enough for Dean to hear, “I’m about to punish that pussy until you come all over my dick, bitch.”

Tiffani’s eyes opened with shock and pleasure at the same time his massive member slipped into her tight cunt. She reached up and grabbed onto his neck while turning her head to find Dean, their eyes met and he winked at her to let her know it was okay. She threw her head back and began to cry out in loud moans of pleasure as Ethan rammed his cock in and out of her soaking wet pussy. Dean was about to tell them to keep it down when Ethan and Tiffani threw their heads back in an explosive orgasm, they were both spent and as Ethan pulled out his dick his come began dripping out of Tiffani’s pussy, mixed with her own sweet juices. He looked at Ethan and as he was pulling up his pants Dean said, “Thanks for stopping by, an impressive show as always, unfortunately we are leaving tomorrow but stay in touch.”

“You know I will, I don’t want this to be the last time I get to have that sweet cunt you own.” He replied with a small smile on his face.

Dean wasn’t done with Tiffani, even though she was laying there running her hands over her breast, and sliding her finger up and down her beat up pussy, gathering Ethan’s come on her finger and pulling it up to her mouth to lick off. Her eyes were closed and when he shut the door behind Ethan he crossed the room to the bed and rolled her over on her stomach. Tiffani rolled with Dean’s direction, she thought he was going to lay down behind her and cuddle up, but he had a much more sinister plan. Dean pulled out his rigid cock, spit on the tip of it, leaned down over her already pleasured body, grabbed a handful of hair pulling her head back just to get her attention, and said “It’s my turn, whore.”

She smiled up at him, and then began to pull away from his dick as he entered her tight unsuspecting asshole. She tried to move away from the pain, but Dean held her down and pushed deeper into her little bum until his balls were pushing against her still dripping twat. She looked back at him with a little tear in her eye and a moan in her voice and said, “Baby fuck my ass hard, I deserve it, I want it, I need it.” So he pumped in and out of her ass until it was filled with his come, Dean only wished there had been someone else there to fill her mouth.

2.

The next day they were on a plane headed to their future, and two years later here she was talking to her friend while her body awaited more pleasure from her toy.

“I don’t know, tomorrow is my graduation day, but Dean hasn’t told be anything yet.” Tiffani replied just before her body shook and her knees began to buckle again.

Scarlette asked, “What’s going on, are you okay?”

“I’m fine, Dean made me put in the triple tickler tonight when I got home and he just turned it back on, with the exception of the slight bit of pain in my ass I had forgotten it was there.” The statement had come out in more of a slight moan than normal speech.

Scarlette, Tiffani, and Dean played with each other on occasion, so when Tiffani had told her what was going on she immediately looked at point between Tiffani’s legs, licking her lips and feeling her pussy growing wet. She stared there, watching as Tiffani’s pants became darker in the center, while her pussy juices started seeping through the grey cotton.

Dean had no intentions of turning it off this time, Scarlette knew what the life was about, hell she lived it with them for a few months before Ethan asked one night if Dean would give her to him. He had let Ethan come over a few times at first to watch what they did, he became really interested and asked Dean to be his mentor on the path to Domination, so when he asked him for Scarlette, he knew Ethan would take care of her the right way and had no problem with it, but it was completely up to Scarlette in the end.

One night, after dinner, Dean told Tiffani and Scarlette to be in the play room and he would join them in five minutes. Like good      submissives they both went to the room, stripped down into their thongs, put their hair in ponytails, sat down on their knees with their hands on their thighs and bowed their heads. This was the position they were instructed to be in whenever they were waiting for him to enter the room, they had perfected it thus far. When Dean entered the room he was wearing a pair of tight fitting dark jeans and a worn brown leather belt, this was his uniform when he wanted to play. Dean walked over to them and asked, “Scarlette why didn’t you finish your chores today?”

“I am sorry Sir, I lost track of time,” was her only reply.

“Tiffani, I see that you finished all of your chores like usual, but I found a pair of your panties in the bathroom with some come in them. Did you masturbate today?” Normally he did not mind her masturbating if she finished her chores on time, but today he was going to punish both of them for something.

“Sir, I had finished my chores and was watching Scarlette scoot around still in her nighty and felt myself growing wet, I didn’tthink it would be a problem since I was already done,” she replied.

Dean stood still for a few minutes thinking about how much fun this was going to be, and then he said, “Scarlette go stand by the horse and wait for me, Tiffani you will be on the table tonight.” They both kept their gaze to the floor as they began to move, but he could still see the look of excitement on their faces. The “horse” is just a reinforced saw-horse and the “table” was a design of his that resembled an inverted table with a hinge halfway up.

He went to the table first, Tiffani was waiting for him ready for the fun and punishment which was about to ensue. Dean strapped her ankles to the bottom corners first, the table is wide so it really spreads her out and then with her face buried in the table he secured her wrists to the upper corners making her a nice little X. Dean decided to leave her like that while he took care of Scarlette, the horse was in a position which allowed Tiffani to turn her head and watch as he conducted business with Scarlette.

Dean walked over to wear Scarlette waited patiently, he handcuffed her wrists together and then hooked them to a cable above the horse so that her arms were over her head. He made her straddle the horse, cuffed her ankles together in irons, and began raising the horse. The cables running from the ceiling where on a pulley system and attached to the ends of the horse. Dean raised it and reached down to Scarlette’s slippery cunt to spread her lips apart, making sure her clit rested firmly on the wood. He continued to raise it until she was on her tiptoes and felt the sharp pain of the wood pressing into her pussy.

Tiffani, who had been watching everything, let out a little moan; a groan of excitement at the position Scarlette was put in, so he decided to turn his attention to her. Dean walked over and released the locks on the table allowing him to then pulled the top half down bending Tiffani over in half. In this position everything was open for use, her cheeks spread apart to show her little anus and her lips spread to allow all of her juices to drip directly on the floor. He went over to the shelf and chose a medium sized butt plug for his little slut tonight; Dean put the plug in her mouth and told her the only lube she was getting was whatever saliva she came up with. While Tiffani desperately worked to make the plug wet Dean put an extra-large vibrator in her wet slit and turned it on, leaving her there to be overcome with pleasure Dean turned his attention back to Scarlette.

Scarlette was soaking the wood with her sweet juices and her eyes were watering from the pain, which was sending shockwaves of pleasure through her body. Dean looked at her and asked what she thought of the games they played with Ethan, to which she replied that she enjoyed playing with Ethan and asked if he was coming over tonight. He slapped her hard on her bum, “you don’t ask questions whore, not in this room, not unless I tell you to. Do you understand me?”

“Yes Sir, thank you for the correction,” she replied. I rubbed my hands along the raised skin that began to redden, and she let out a little sigh.

“How would you like to finish your training under Ethan?” he asked.

“Sir, if it would please you, I would leave and continue to learn from Master Ethan, but I will miss you both so much. If I go will you still love me?” Scarlette asked.

“You will always have a place here, and if you ever need me I will be there for you,”Dean told her.

He lowered the horse and let Scarlette down, telling her to go stand by Tiffani, who had started squirting all over the ground from the vibrator. Dean walked over and pulled the vibrator out of Tiffani’s gaping hole, while telling Scarlette to put on the 7-inch strap-on. He pulled the plug out of Tiffani’s mouth, a stream of saliva stretched between her mouth and the plug. He walked behind her, placed one hand on her ass and put the tip of the plug against her tight hole. Her pussy still quivered from the multiple orgasms she had while the vibrator pulsed through her vagina and her ass tightened briefly when she felt the warm steel of the plug. Dean pushed the tip in, and continued to apply pressure until her ass opened up and allowed the plug to slip inside of her up to the neck.

Scarlette had returned wearing the strap-on and as he picked up the paddle he told her to let Tiffani suck on the rubber cock. Tiffani’s eyes went wide with excitement as she took the whole 7-inches in her mouth, she was amazing oral sex even if it was a dildo. As Scarlette began to thrust in and out of Tiffani’s mouth Dean raised the paddle and brought it down hard across her bottom at just the right point to push the plug in deeper. She let out a muffled scream around the rubber cock still being thrust deep into her throat, and again he struck her with the paddle, over and over, until she shuddered with another orgasm, splashing his bare feet with her warm come. It was a magical night, and one of her fonder memories.

Tiffani was twitching when Dean came back from the den, he was talking to someone about tomorrow night in a hushed tone. Tiffani was in a state of pure ecstasy, her pants getting darker and darker as her sex soaked through them. He pressed the off button right as he came down the hall, her body immediately relaxed as she looked at him in disappointment, she had been so close to coming but he wasn’t ready to let her release yet.

“Well, Ethan will be waiting for me back at the house, I should get going. I can’t wait to come play with you two again, and I know my Master would love it as well,”Scarlette said as she hugged Tiffani and Dean.

“Tell Ethan I will call him later to set something up, as soon as I can find the time that it,”Dean replied as he released her from their hug.

Scarlette looked back at them as she walked towards her car, and gave a smile and a wink. Tiffani and Dean waved goodbye to her, and he pressed the on button to her remote vibrator as the door was closing, Tiffani reached out to steady herself and he told her, “I’m thirsty.” With a wink and a smile.

 

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