Second Chances

Pleasure before work

Jack's sister agrees to represent them in the law suit. She comes to stay with Jack during the procedure. Jack is excited about introducing Alanna to his sister. His sister had always been at his side, so he was hoping that she saw what he saw in Alanna.

Jack asks his sister Mary to go with him to the funeral home and meet Alanna. It was the weekend, but Alanna had two services, so she had to work. Jack arrived at the funeral home with Mary. They walked into the crowded lobby. Carol saw Jack making his way to the front desk. She walked to him and explained that Alanna was out picking up some more pastries because they had run out, but they were welcome to wait for her in her office. “I know she won't mind,” Carol said smiling, lifting her eyebrows.

Jack took Mary to Alanna’s office. He offers her a chair, but Mary prefers to roam around the office. She studies the decoration and the things Alanna had around her office. Alanna had pictures of her kids and her late husband. She had trinkets from the places she had visited and lots of books. Mary grabbed a trophy from a shelf. She was laughing, looking at Jack. Jack asked, “What is it?” His sister held the trophy in front of him and exclaimed, “first place amateur wet T-shirt contest.” Jack took the trophy away and placed it back where his sister found it. He looked at his sister seriously. His sister asked, “ Did you knew about that?” Jack sighed and walked away saying, “Her husband signed her up for it.” His sister replied, “I know you will never approve of such a thing, but at least she got the first price.” Jack looked at his sister and smiled, “They were incredibly open-minded. I thought that was going to be a problem for us, but she is different with me.” “I hope so.” His sister replied. Then she sat on Alanna’s chair. “ Comfy!” she said, reaching to open her drawer. Jack grabbed his sister's hand, preventing her from snooping in Alanna’s drawer. The commotion turned on Alanna’s computer. Jack froze. His eyes widen as he stares at the computer. Mary looks at what had her brother mesmerizes. Jack stares as the screen shows picture after picture of him. He places both hands on the desk to support his body. Jack is surprised to see that Alanna has a picture of him working out that he didn’t notice her taking, and another of her lying on his chest while he was sleeping.

Mary snaps him out of it saying, “I imagine her taller.” Jack looks at his sister. Mary was looking out the door. He looks up and sees Alanna entering with boxes in her hands. Alanna walked straight to Carol. Carol talks to Alanna and she looks towards her office. Alanna sees Jack standing behind her desk. Alanna lifted a finger asking for a minute and walked into the cafeteria. Mary then says, “She looks stuck up.” Jack frowns at her. Alanna walks out of the cafeteria and Jack stands up straight. Then Alanna looked at him one more time and lifted her finger again. Alanna went into one of the rooms holding an old lady. “Okay, she doesn’t look that bad and I love her shoes”, Mary said, smiling at Jack. Then Mary asked for a bathroom. Jack showed her to Alanna’s office bathroom. Entering the bathroom, Mary grabs a man's deodorant and shucks, “Is this yours?” Jack gets serious, takes the deodorant away from her and places it back where it was originally. “ Yes, leave it alone” Mary laughs and closes the door.

Alanna walked into the office and locked the door. “I’m sorry to leave you waiting”, she said, kissing Jack and sliding her hands inside his shirt, lifting it and taking it off and grabbing his bottom as she kissed his chest, neck, and…. Mary walks out of the bathroom. “I’m sorry.” Alanna pleads, nervously putting Jack’s T-shirt back on. Mary looked at Jack’s embracing face and laughed. Jack fixed his T-shirt and introduced Alanna to his sister. Mary slaps Jack on the head and tells him, “You could have told her I was here before she went all animalistic on you, but now I get it.” Alanna hugs Jack and shoves her face in his chest embarrassed. Alanna then turned to Mary, stretched her hand and said, “It is a pleasure to meet you.” Mary laughed, “no need for professionalism, I just saw you almost devouring my brother. Alanna went back into Jack’s chest. Jack held her laughing. Alanna asked them to sit. Mary sat on the sofa in the corner and Alanna pulled out her desk chair for Jack. Alanna leans against her desk. The computer turned on to the screen saver again. Alanna clicks the mouse immediately, trying to change the screen. Jack stood up and took the mouse away, “What are you trying to hide?” He said, kissing her. Alanna looked down and whispered, “You saw it already?” Mary interrupted. We both did, “I thought it was a little stalkery, but this guy was about to cry.”

Alanna embraces Jack and kisses him. Jack looked at her eyes, holding on to her and whispered, “why did you change it?” Alanna kissed him and whispered back, “because I love you and want to see your face all day”. Jack’s eyes filled with tears. Alanna kissed him and got teary eyes too. “Okay, we get it, you are in love. Can we talk strategy now?” Mary said, lying back on the sofa. Jack and Alanna laughed and turned to Mary. Jack lay against the desk and pulled Alanna in front of him.

Mary talks about the case and how she will deal with it. She then asked Jack if he thought that that was the best way to do it. Alanna wondered why she was asking him. Mary noticed Alanna looking confused and shouted, “You haven’t told her?” Alanna moved off Jack and turned towards him asking “What haven’t you told me, Jack?” Jack gave his sister an evil look and moved away to the other side of the desk. Jack looked at Alanna with a worried face. Alanna crossed her arms waiting for an answer. Jack rubbed his chin and began to talk, “before I became a police officer, I was a lawyer. Mary interrupted, “A very good lawyer.” Jack looked down and continued, “I became tired of criminals walking away due to technicalities so I decided to become an officer and ensure that the cases are properly prepared so no more criminals walk away” Alana relaxed her hands and rushed to him she wraps her arms around his neck and said, “That is awesome, but I thought you were born in your uniform because you make it look so good.” Alanna kisses him. Mary opened her eyes wide. That wasn’t the reaction she expected. Most of the women Jack tells the truth to will start questioning why he would do something like that. That is why Jack stopped telling people. It seems like everybody thought it was a step-down. Alanna surprised Jack as well as Mary by telling him that she was so proud of him. Choosing to serve instead of money and prestige is not easy for most people. Jack held Alanna tight and kissed her neck. Mary placed a hand on Jack’s back and said, “I get it now.”

The three of them go to Jack's house later. They had dinner. Then they strategized for the rest of the night. Alanna didn’t understand what they were talking about most of the time. She sat on the sofa and Jack sat on the floor resting his head on her. Alanna played with his hair and caressed his beard. Occasionally Jack looked up and kissed her. Jack rubbed Alanna’s legs up and down and occasionally picked them up and kissed them. After a while, Alanna asked him to sit on the sofa. Jack sat behind Alanna and massaged her back. Alanna moaned as his strong hands cracked her back. Mary looked at her phone, “Look at the time, it is so late, I should go to bed.” She picked up the papers from all over the living room and headed to the guest bedroom, which was across from Jack's room. Alanna and Jack cleaned the kitchen. After they finished cleaning the kitchen, Alanna ran off, took her clothes off and jumped in the pool in her lingerie. Mary heard the splash, so she went out to check what was happening. Jack laughed loudly, “Are you crazy, it must be cold.” Alanna nodded, “freezing come on in, keep me warm.” Jack looked around but he did not see Mary. He took his shirt and jeans off and jumped into the pool. Alanna swam away having Jack chase her. Jack swam after her, laughing. He was so much faster than her. He had her in his arms in no time. Alanna laughed and splashed water on his face. Mary laughed. She could not believe she was watching her shy older brother act like a teenager in love. Alanna began to shake. The water was cold. Jack held her closer to his body. She wrapped her legs around his waist, and he rubs her body trying to warm her up. Mary retired back to her room. Alanna thought she heard something, but Jack convinced her that there was nothing there. Alanna decided to go out of the pool, but Jack took his underwear off and told her, “I’m going to keep you warm, take your clothes off.” Alanna did as she was told. Jack picked her up and wrapped her legs around him again. Alanna hugged him shaking. Jack kissed her. Their bodies together began to produce heat. Alanna stops shaking. Her n*****s were hard poking Jack on the chest. He lifted Alanna out of the water until her n*****s were out of the water. He blew warm air at them. Alanna's arousal makes her warm. Jacked slid her down his body. He felt the warmth between her legs heating all his body. He rubs himself against her warmth and places himself in her opening. Jack kissed Alanna passionately. Alanna rubs herself against him. Jack grew inside of her. Alanna tightened her legs stronger to prevent him from sleeping off. It was hard to keep their balance. Jack told her to take a deep breath and he let himself sink to the bottom of the pool with Alanna wrapped around him. They kissed, holding their breath. Jack rotated her on top of him as she held on tight. When they felt like they were going to pass out. They both swam fast to the surface gasping for air. They stood in the freezing water kissing and laughing. Jack grabbed Alanna and took her to the hot tub. He sat and asked her to sit on him. Alanna held on to his shoulders as she pushed through the bubbles. Jack grabbed her bottom and pulled her hard on him. He places a hand over his mouth to keep her from screaming. Alanna mutter. She lay back on the water. Jack held her back up and pressed her against him at the same time. Alanna holds on to his forearms. Her breast bounced in and out of the water with the force Jack was using to pull and push Alanna on him. Jack grunted as he used more of his upper body strength. His muscles flexed. Alanna was losing her grip, so she lay over him and bounced on him, smacking his chest with her breast. Then Jack asked her, “are you there?” Alanna answered, “Almost.” They grunted, they moaned and then they sighed loudly. Jack kisses Alana’s chest. He holds her tighter and then releases her a little bit. They embrace and enjoy the water pressure massage.

Alanna falls to sleep on Jack. He holds her, trying to keep her from going under the water. She took a little nap and Jack held on to her. When Alanna woke up, Jack ran out and grabbed towels for them. He held a towel up for Alanna. As Alanna emerges from the hot tub, Jack wraps her in a towel and his arms to keep her warm. Alanna trembles all the way to Jack's room. They jumped in the shower and turned the water very hot. The bathroom was so steamy that they couldn’t see outside the shower. Jack scrubbed Alanna’s back and then washed her hair. Alanna walks from the shower straight to the bed. She jumped into bed without drying herself. Jack did the same right behind her. They crawled under the blankets. Jack laid behind Alanna spooning her. Alanna slept in the safety of his arms.

The next day, Mary woke up early and made breakfast. She waited for them to wake up, but Alanna and Jack slept late. The doorbell rang and Mary answered. It was John and Jack's mother, Hannah. This time they didn’t use the key to walk in due to fear of finding Jack having s*x again. “Is everybody decent”, John asks, covering his eyes before entering the house. John and Mary laughed. Their mother didn’t find it funny. She walked into the house, looking around. Mary noticed her mom searching for something, so she told her that Jack was still in bed. Jack’s mother proclaimed upset, “He still sleeping on a Church day?” Mary then lets them know that Alanna is there with him. Jack’s mother sighed, “That woman is still around?” Mary smiled, “I don’t know but they seem happy.” John placed his finger over his mouth gesturing to Mary to stop talking, but he was too late. Their mother starts talking about how Alanna is the devil and she is using her body to seduce Jack. She claims that Alanna is a temptress that is guiding Jack to a path of destruction. John tries to change the subject, but she goes on and on about how she is using her s****l tricks to keep him under control. John passes behind Mary and whispers, “for what I have seen, big bro has tricks of his own.” Mary laughs and their mom frowns at them. Mary then offers them some food. Jack’s mother accepts the offer. She sat at the table to eat. John sits right next to her. They sit at the side facing the glass doors that lead to the pool.

Jack and Alanna wake up and head to the pool area to exercise. They used the side door, so they didn’t notice that Jack’s family was sitting at the dining room table watching them. Alanna starts by stretching. Jack interrupts her by rubbing against her every time she bends. Alanna laughs and pushes him away. Then Alanna is squatting, and Jack started lifting right behind her. His lust for her was obvious. He looked at her like pray. Alanna turned around and saw how he was looking at her. She smiled, and he threw the weight down. He rushed to her and began kissing her. She slides her hands inside his shirt, caressing his back, and he slides his hands into her pants, grabbing her bottom. Jack’s mother sights. Mary realized that she needed to put a stop to them before things got too steamy. Mary knocked on the glass. Alanna and Jack jumped and looked towards the window. They were petrified to learn that Jack’s mother, John, and Mary were there watching them.

Jack took his hand out of Alanna’s pants and waved to him. Alanna holds on to his waist and smiles. John was cracking up, pointing at them. They walk into the dining room and John screams, “Dude!” laughing loudly. Jack’s mother looks at Alanna from head to toe and grunts. Mary said good morning to them and offered them food. Alanna goes to the kitchen and takes some fruit out of the freezer and starts to make a shake. She offers everyone. No one wanted a milkshake, so Alanna made enough for herself and only Jack. Jack went into the kitchen, kissed Alanna and served two plates of food. They move to the table. Jack pulls Alanna’s chair and Alanna blows him a kiss. Jack served two full plates. Mary was surprised to see how much food Alanna had on her plate. Mary said to Jack, “you served Alanna as you served yourself.” Alanna laughed, “I ate a big breakfast. Jack knows exactly what I like.” Alanna rubs his arm. Jack’s mother cleared her throat. For a minute Alanna forgot that Jack's mother was there and acted normal. Jack fed Alanna from his plate. Alanna caressed his face. Jack’s mother watched them quietly disapproving of everything they did.

After breakfast, Alanna and Jack excuse themselves. They went to Jack’s room to get ready. Alanna had to go to work for the rest of the day. Jack didn’t want her to go, so he offered her a massage. Alanna didn’t want to stay any longer with Jack’s family in the house.

Jack grabbed Alanna. She tried to break loose, but his grip was too strong. This time he made sure to lock the door. Jack kissed Alanna’s neck and whispered in her ear, “You look tense, please let me help you relax.” He laid Alanna naked in his bed. He pulls from under the bed a box of oils that he bought for Alanna. Alanna was intrigued, “When did you come up with this?” “I bought them a few days ago but I haven’t had the chance to use them,” Jack told her, pouring some oil on her back. He rubbed the oil around her back. Then he moved to her legs. He left her bottom for the end to avoid getting too excited. He rubbed her bottom around, then he poured more oil on her bottom and he massaged the middle of her bottom. He rubbed her from top to deep in between her legs. Alanna enjoys the sensation. She moans. Jack asked her to turn around and he repeated the process. He started at the top. He took his sweet old time on her breast. He pours a lot of oil on Alanna's breast and rubs them until the oil disintegrates.

Alanna started to moan too loudly, so he grabbed a tie and tied it around her mouth. Then he tied a tie to each of her wrists and her legs, he secured them to the sides of his bed. Then he continued his massage. Jack massages her legs, then he moves to her chest, he pours almost the whole bottle of oil on her breast. He massages her breasts, flicking the n*****s instead of rubbing. Alanna moan. Then he began to massage her belly, moving down until he met with her legs. He spread her legs, climbed on the bed between her legs and added more oil to his hands. He started massaging with each hand at the outer edge of her thighs, little by little bringing his hands closer to the middle. He rubbed her until his hands met. Then he used one hand to outline her opening and tickle her sensitive spots. He then moved his hands to her breast, and he squeezed them as he lowered his head and blew on her sensitive area pulsing in expectation. He licked her slowly from side to side, stiffening his tongue to apply pressure. Alanna twisted and moaned. Jack then bit softly and placed his whole mouth over. He latched like a leech sucking and biting her. Alanna tears up. She was screaming and twisting as he ate her up. Jack licked, sucked, and bites until his tongue hurt. Then he took off his pants and introduced himself inside her. He pinched her n*****s and squeezed her breast as he slowly moved in and out of her. Jack asked Alanna to tell him if she wanted it faster or harder. Alanna tried to tell him, but the tie didn’t let her speak, so he continued slowly. Jack tortured her until she was soaked. Then he knew she was ready. He began to push himself into her harder and faster. Jack let Alanna's hands and legs go. Alanna dug her nails into his back so hard that she drew blood. Alanna shook her head from side to side and then she became stiff. At the same time, Jack exploded inside of her. Jack falls on her gasping for air and he finally pulls the tie out of her mouth. Alanna, gasping for air, whispered, “how am I going to work now?” Jack laughed. He whispered into her ear, “ Don’t worry, I’m going to help you.”