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Tiffani's Struggle Chapters 3 and 4

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

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3.

Tiffani had been brought to the edge of coming for the past forty-five minutes as Dean sat in his chair with her kneeling by his side on the floor. The only time she moved was if he needed something. Dean sat there running his hands through her hair while they waited for dinner to arrive.

Tiffani had already been made to strip out of her cotton PJs and put on her spiked heels, so as she knelt there he could look down and see the growing puddle of delicious cum building under her legs and the spikes on her heels pressing into her ass.

When the doorbell rang Dean looked at her and said, “answer the door Tiffani, make sure you tip the delivery boy generously,” and with a wink, he smacked her ass as she stood up. She was thrilled and nervous about what she had just been instructed to do. She loved showing off for everyone but was also very aware of her current state.

Tiffani walked over to the door. Dean had already turned off the triple tickler so she would be able to concentrate on what she was doing, and she opened the door. Standing there before her was a kid in his mid-twenties. He was of average height, tanned from a summer of beaches, and well-built from what was probably some backyard gym.

Dean was impressed with this one, he was new and not their typical delivery man. Hopefully, they were going some fun. The look on the young man’s face was well composed, even with the surprise of a gorgeous mostly nude woman standing in front of him playing across his eyes. Dean could tell by how well he was controlling himself, this was not the first time he had been greeted in such a way, but he was sure this was the first time a tip like this had ever come his way.

Tiffani looked at the delivery boy as he handed her the bags, his eyes roaming all over her like hungry hands reaching out. He paused and leered every time his eyes reached her warm pink center, which glistened with the sex she had been dripping for over an hour.

“Ummm, it comes to $78.42, ma’am,” was all he could manage.

“I don’t have my purse on me,” she answered with a sly smile on her face, “would you please come in while I get your money?”

He followed her into the house as she turned and walked to the kitchen with the food,.When he noticed Dean for the first time he jumped, he was well built but sitting before him was a very large well-built man, who was obviously the husband.

“It’s ok, Chad, just relax and enjoy, I hope you don’t have any more deliveries in your car.”

He was wearing his work shirt with a gold name tag. Dean loved watching this, he would set this up maybe once every five to six months and every time, he hoped for the best.

Tiffani placed the food on the counter and reached for her purse, she pulled out her wallet and began counting out money for the food. She counted out $80.00 and then looked at Chad and said, “I don’t seem to have enough for the tip, I’m so sorry.”

“That’s okay Miss …”

“Tiffani, please call me Tiffani.”

“That’s okay Tiffani, I think I will be just fine,” and with a timid, but knowing smile he began to walk towards the door.

Tiffani reached out and touched his arm, “I’m sure there is something else I can give you for your trouble.”

Chad turned around as she reached down and undid his belt, she expertly unbuttoned his pants and slowly pulled the flaps apart while the zipper gave away. As his manhood was becoming hard and ever closer to freedom she licked her lips, and without even looking down she reached into his boxers and wrapped her hand around his endowment.

Her eyes lit up with what she found down there, his cock was thick and growing longer by the second, she knew she could handle it and couldn’t wait to release the sperm built up in the thick vein running along its underside.

Chad looked at Dean again, with nervousness in his eyes, and he was given a wink putting him at ease. Chad seemed to accept this gesture and turned towards Tiffani, looking in her beautiful eyes. She had already moved to her knees and was caressing his beautiful member. She looked up at him one last time and licked the tip of his fully erect penis, then without warning and with the grace of a woman who loved her craft she took the whole thing in her mouth.

She began taking him deeper and deeper in her mouth, drool beginning to drip from his shaft as she worked up and down his cock, Dean knew this was not what she wanted, she liked to be fucked in her mouth. So he walked over to Chad, put a hand on his shoulder and whispered in his ear, “Treat her mouth just like you would any one of those Sorority sluts’ pussies you’ve pounded out.”

The smile on Chad’s face grew as he put his hands on the back of her head and wrapped his fingers in her hair. She knew the drill and she let her arms fall from his penis and reached back to grab the heels of her spiked shoes. Chad started out slow at first, pressing his dick in as far as he could and holding it there until she began to gag. To Dean’s surprise he told her, “Choke on my dick you dirty whore, you know you want to.”

Chad began thrusting harder and harder pumping his meat in and out of Tiffani’s sexy mouth, her gags were coming closer and closer together, her eyes watering, and she was loving every minute of it. Dean decided it was time to let her cum just once, so he pushed the button on the tickler again and set it to the highest setting. Yes, this was going to be amazing. Tiffani started twitching with growing orgasm, all the while Chad thrust his massive member into her mouth with fury.

As he slammed his dick deep into her throat, the pool of drool on the floor that dripped from his cock started mixing with the cum squirting out of her cunt as she was racked with orgasm after orgasm. With one final push, Chad threw his head back and his muscles stiffened, while his hot white jizz shot into her throat filling up her mouth. There was so much, Tiffani couldn’t swallow all of it and it began to leak out around his shaft and fall to the floor.

Dean walked over to Chad and thanked him for the delivery, told him to pull up his pants and never forget this house.

“Oh, I will be sure to bring you all of your food from now on,” Chad said.

Dean shut the door behind him and turned to see Tiffani still convulsing from her orgasms. He had already turned off the tickler so she could relax a little bit. She still had some of Chad running down her chin so he walked over to her, knelt down, and pulled her head into his chest. With his other hand, he gathered Chad’s remaining sperm off her face and held it out like a lollipop for her to suck on.

“Aren’t you going to finish your dessert Tiffani?” he said as she took his finger in her mouth and cleaned off the remaining white goo with her tongue.

 

4.

Dean decided that tonight while they ate, Tiffani could relax and have a free talk, so she put on a robe while he began making their plates. When they sat down to eat she looked at him and said, “I love you, baby, will you tell me what the plans are for this weekend?”

“Well tomorrow is your Graduation ceremony, I have a very nice plan where you will get your permanent collar, other than that, no, I will not tell you that.” He couldn’t let her know the plans he had made. All of their friends were going to be there, and by the time the night was over Tiffani was going to be pleased and fulfilled.

Tiffani was not satisfied with the answer she received, but she knew better than to push the issue. Dean would never hurt her and she trusted him completely to bring her the most intense pleasure, and safety she had ever experienced. They sat there and finished dinner and shared a bottle of wine while laughing about the look on Chad’s face earlier. When she stood to clear the table he told her not to worry about it, he would take care of everything tonight, but her free time was up.

“Go get ready and wait for me in the playroom, I will be there shortly,” Dean instructed.

“Yes, Sir,” was her only reply when given an order, and as she bowed her head she walked to the room to prepare, and wait for him. Dean tidied up the kitchen, and the living room and stepped outside to enjoy a cigarette. Tiffani was waiting on him, but she knew he liked to make her wait, and as she sat there her excitement grew more and more. She was used to doing what she wanted when she wanted, so since they started their relationship he had worked on making her wait a little longer each time for her reward.

Dean sat on the porch enjoying the quiet of their little neighborhood and thinking about how Tiffani was patiently waiting for him. Tiffani was kneeling by the door when he entered the room in her red lace thong with her hair down, her patience starting to falter. She had her hands resting on her muscular, thick thighs and her head was bowed making her stare at the floor.

“I am yours to use as you wish, Sir. My body is yours to play with, my mind is yours to mold, and my soul is but one half of ours together,” she said to him.

“I will use your body, and your mind will be formed by my hands, and our souls are together in this place and all others, forever,” Dean responded. A little corny for what they were about to do, but it’s the way they had started out every time and it just stuck.

Dean walked over to Tiffani and placed his hand on top of her head, feeling his touch she let out a slight moan, and he tangled his fingers in her hair, grabbing a fistful of it and pulling her head back. When she looked at him, he told her we would start tonight with a shower.

Their playroom was very extensive, Tiffani loved how Dean had put it all together and it made their evenings very full. There was a bed along the back wall, a small glass shower, a couple thick armchairs for watching, quite a few bondage racks, and every wall had glass shelves for their toys and drawers for costumes and other clothing. She bowed her head in acknowledgment and began to rise and walk over to the shower, he followed stopping briefly at one of the shelves and picking out a twelve-inch long, thick suction cup dildo.

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When they got to the shower, Tiffani removed the rest of her clothes and started the water, while Dean attached the dildo to the glass wall facing into the shower. He sat down in the leather armchair right in front of the shower, and when Tiffani had the water set to the right temperature she turned around and noticed for the first time the toy he had selected for this activity. The look of surprise on her face was priceless, she had taken this toy before but only when she was strapped down and Dean was pushing it in. This time, she would have to work it in all by herself.

Tiffani soaked her body under the shower head and then knelt in front of the massive rubber cock. She looked through the glass at Dean as she stuck out her tongue and proceeded to work the huge toy into her mouth and down her throat. She began gagging almost immediately as the tip of it pressed against her throat, but she stuck with it and started to slide her tongue and mouth up and down the perfectly sculpted shaft attached to the wall.

His own cock sprang to life and he unzipped his pants to let the large meat stick out. He pulled it out through his pants and held it tight in his hand. When Tiffani looked over at Dean, she was instantly thrilled to see what he had in his hand. She enjoyed her toys and all the people they invited into our bed, but there was nothing she loved more than his homegrown snake.

“Tiffani that is enough sucking, stand up and turn around so you can back up on it,” Dean instructed her.

“Yes, Sir,” was all she said as she stood up and turned around in the small shower. There was just enough room for her to put her hands on the opposite wall and back her ass up so the tip of the dildo pressed against her dripping wet lips. Dean had put a mirror against the wall so whoever was in the shower could use it to watch the fun outside.

Tiffani looked at him through the mirror and he gave her a nod to go ahead, and with that one simple gesture she started to push against the wall and grimaced slightly as the massive rubber toy began to spread apart her lips and enter her moist cunt.

She pressed against the wall more and more, allowing the dildo to fill her up and go as deep as it could. Once she had taken ten inches of it, she began pulling off of it, and then when she could feel the head of her toy at the edge of her pussy she pushed back against it hard. She was ready for this. She started to rock back and forth against the soft rubber, over and over again as her pussy grew wetter and wetter with her sweet juices.

She worked the dildo with all she had in her, ramming her pussy hard, so hard she had tears forming in her eyes. She was coming close to climax and she looked at Dean for approval. Tiffani never came without his permission. He nodded to her and told her it wouldn’t be the only time tonight.

Tiffani was pleased and began slamming her ass against the glass forcing the entire length of the dildo into her pussy now. The pain was becoming unbearable and just when she was about to stop her hot sticky cum shot out against the glass and her body was filled with the magical feeling of her orgasm.

With her legs shaking, she pulled herself off the dildo and shut off the water, and when she opened the door he was there to greet her with a towel. Dean dried her off from top to bottom, stopping while he was drying her legs to take in the sweet aroma of her perfect vagina and let his tongue lap up the rest of her cum. He finished drying her off and told her to go lay on the bed face down, where he strapped her to the four corners with the nylon bondage straps running under the bed.

With Tiffani strapped down to the bed, Dean walked over to the belts he had hanging on the walls and grabbed the worn out brown leather one they used for the first time in Crete. The belt was nothing special, just one of his old leather belts, but she loved it because of all the memories attached to the cracked cowhide he held in his hands. He returned and put a wooden gag in her mouth, it was a simple piece of wood dowel attached to a wire which wrapped around the back of her neck.

She knew when he used this one the spanking would be painful, and it excited her. With her gag secured in place, he started tapping her ass with the tip of the belt. With every tap, she would tense a little so he continued until she stopped tensing and then he brought the belt over his head and back down hard on her cheeks.

Tiffani let out a little squeal. She threw her head back and tried to move away from the pain, but there was nowhere to go. She didn’t want to get away from it anyway, she welcomed the pain, even loved it.

“One.”

Tiffani knew she would count each strike out loud and if asked whether she liked it or not she would say, ‘yes, Sir, please give me another.’

Dean raised the belt above his head again, and again he brought it back down hard.

“Two,” she cried out.

The tears were flowing freely from her eyes at this point, the pain made her feel good but the tears released all of her stress and that’s what she really craved. “Three,” she screamed through the gag. If this kept up much longer she would bite through the wood so he decided he would give her one more and be done with it.

“Four.”

This one came out between sobs of pain and pleasure, and Dean reveled in it while he walked across the room to hang the belt back in its place.

He returned to Tiffani and sat next to her, reaching over to the nightstand and grabbing a bottle of oil he asked her, “Tiffani, are you feeling okay?”

“Yes, Sir, please give me another,” she sobbed out. Dean knew she didn’t need any more so he just started rubbing the oil into her marks and soothed her pain. She lay there under his hands and began to moan and relax with the soothing oil and rhythmic massaging.

Dean loved this woman so much, and he would do anything for her, she had never felt such a feeling of safety from anyone before. Even growing up, Tiffani’s parents never showed her the amount of love, compassion, or sense of safety Dean showed her every day.

With Tiffani completely relaxed, he decided to continue on with tonight’s festivities. With his pants already off, he straddled over her and positioned himself so the tip of his cock was resting at the base of her ass. Dean moved up to her back and continued to massage her with the oil, working out all of her worries and frustrations. As he did this, he began scooting forward just a little bit each time he worked her shoulders. With each move, she could feel him bringing his raging hard dick closer and closer to her anus.

Ready, and in position to thrust, he leaned forward and whispered to her, “Tomorrow you become my slutty submissive, but tonight you’re still my whore,” and with that, he drove deep into her ass with all his force. Her body jerked and she instinctively raised her ass to allow him to penetrate her even deeper, and when she moaned out in cries of pleasure she said, “Sir, please fuck my dirty little hole as hard as you can.”

Dean fucked her like he had never fucked her before, his cock sliding in and out of her tight little asshole, his balls slapping against her soaking wet pussy, and his hand grabbing her beautiful blonde hair so he could pull back on her head.

“Would you like to play with your throbbing cunt, you little whore?” he asked her.

“Yes please, Sir,” she responded.

He freed one of her hands from its bond and she reached straight down between her legs to find he swollen pink clit, rubbing furiously back and forth on her little pleasure button trying to keep pace with the thrusts abusing her anus. As Dean felt himself close to climaxing, and she already having drenched the bed and his balls in her own juices, he undid the rest of her bindings. Dean wanted her to swallow what he had to offer tonight, he wanted to see his hot, white cum dripping off her chin just like Chad’s had earlier.

Dean grabbed a hand full of Tiffani’s hair and pulled her off the bed, he forced her down on her knees and told her to grab onto her ankles. When she was in position he tilted her head back and looked in her eyes as he stroked his throbbing member, “You are going to swallow everything, and whatever falls from your mouth you will clean with your tongue.”

She licked her lips in preparation and he stepped forward pushing his cock deep in her eager mouth, he was already so close he only had the chance to thrust a few times before he grabbed the back of her head and forced her down the entire length of his shaft. She began choking on it, but Dean held her there as he felt his juices filling her throat, she began swallowing as fast as she could but she couldn’t keep up. After only a moment his cum began to leak out all around his dick and drip to the floor, and when he pulled his cock from her mouth there was a string of his semen stretched out between them which she sucked into her mouth with pride.

After Tiffani had cleaned up like Dean told her, he lifted her and carried her into the bathroom and placed her into the already filled claw foot tub. He climbed in behind her and began to bath her with sensual lotions and oils until they just lay back, Dean against the tub and Tiffani against his chest and soaked in each other’s love and presence until the water began to cool. When they got out they both put on their thick white bathrobes they got from another party they had a while back, and went to the bedroom to fall asleep in each other’s arms.

Published 
Written by JakeLong
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