A Second Chance at Love Pt. 2

Jim felt like he was unleashing his soul into his lover's ass. His cock pulsed and squirted more times then he could ever remember. Each time his cock pulsed, Jenny's ass responded, squeezing him and forcing another pulse. Jim no longer knew if the intensity was from the situation or the fact that he was fucking his lover's ass. He no longer cared.

"Wow," Jenny whispered as she felt Jim's cock continue to throb and squirt. She brought her lips to Jim's and kissed him passionately.

When their lips parted, Jim looked over to where Katie had been. He saw that she wasn't sitting on the porch any more. She was gone. Jim shook his still spinning head. Had Katie even been there he thought? It seemed like it could have been a dream, a very pleasurable dream.

Chapter 3

When Darlene got into work at 8:15 on Monday morning there was a message on her desk to come directly into Jim's office. She put her pocketbook down and went to Jim's door immediately and tapped lightly.

"Come in," Jim said.

When Darlene walked into Jim's office, she stopped abruptly. She saw that Jenny was sitting on the sofa. Darlene immediately became very nervous. She knew that something was wrong, and deep inside she knew what it was.

"Sit down Darlene," Jim said sternly and pointed to the chair.

Darlene took her seat and looked briefly at Jenny who was sitting there with a frown on her face.

"Darlene, I am disappointed in you to say the least. How long have you worked for me?"

"Nine years this month."

"You have always done a wonderful job and been a very loyal assistant. Sometimes I wonder how I would have ever gotten things done around her without you. Unfortunately, I am going to have to let you go."

"Oh God, no!" Darlene said and immediately began to cry.

"Do you know why I am letting you go?" Jim asked.

"No...sob...sob..." Darlene lied as her tears fell.

Jim reached over the desk and handed Darlene a box of Kleenex. "I believe that you do Darlene. What happened to the letter that I gave to you to deliver to Jenny?"

"Oh God Mr. Lewis, I'm so sorry. Please don't fire me. I live alone and this job is my only source of income."

"I'm sorry Darlene but I can't trust you. Do you know that by destroying that letter that you almost ruined my relationship with Jenny?"

Darlene looked over at Jenny then back at Jim, her eyes red and tears were streaming down her cheeks. "I...I...I was only trying to protect you. I never wanted to hurt you, you have to believe me," Darlene sobbed.

"Protect me from what? Protect me from Jenny? Who made you my protector?" Jim said angrily.

"I just thought she...she...wasn't right for you," Darlene said, wiping her eyes and nose. "I'm so sorry."

"Well, it's a little too late for apologizes. You can clean out your desk and..."

"Wait Jim," Jenny spoke for the first time. "Can I see you outside for just a minute."

Jim looked over at Jenny in surprise. "Okay," he said and got up and led Jenny out of the office.

"What's going on?" Jim asked.

"Do you know why she did what she did to us?" Jenny asked.

"She is obviously jealous of you and can't keep her nose out of other people's business," Jim stated with a sneer.

"Yes she is jealous, but jealous because she loves you."

"Loves me! That's ridiculous!"

"It's true. I bet she has loved you since the day she came to work for you. She was just a kid and you were the big important attorney. I can see how she could fall in love with you-I did. Jim, the truth is that I feel sorry for her."

"Sorry for her? Jesus Jenny, she almost destroyed our relationship."

"Well, I'm not so sure about that. If she hadn't done what she did, you may not have faced your own demons and I certainly would not have spent the weekend with you. Darlene's motives were more for herself but they came from her heart," Jenny said and paused. Then she took Jim's hand and said, "I think you should give her another chance."

"Another chance? I can't believe that you, of all people, are saying that."

"Jim, think with your heart not with your lawyers mind. Darlene is a lonely woman. I think there is something in her past that has made her go into a shell, much like you did. I don't know what it is but who knows, maybe she lost someone she loved too."

"Come on, you don't know that."

"You don't know and neither do I. All I am saying is that we all need a second chance. You finally have your second chance, why not let her?"

Jim was silent as he turned and walked across the room to the window. "That's different," Jim said as he looked absently out the window. "I was emotionally scarred," Jim said then realized how stupid that sounded. He didn't need this right now he thought. He stood there for a few moments in silence then said, "What if I did give her a second chance, how could I trust her again?"

Jenny walked over to Jim and put her arm around his waist and put her head on his shoulder. "I think you can trust her. She loves you and she knows that she has hurt you deeply," Jenny said. "Listen, I have an idea. Let me work with her for a week and find out more about her. At the end of the week I will be able to tell you if she is trustworthy or not. I think Darlene just needs to come out of her shell and I think I can bring her out. If I am wrong, you can always fire her. What have you got to lose? If I am right, you keep the best assistant you ever had."

Jim couldn't argue with Jenny's logic. He really would miss her. "Alright Jenny, but just a week. I don't know why I am letting you talk me into this," Jim said with a little smile.

Jenny hugged Jim. "Because you love me. Thank you. I knew you had a big heart under that stiff lawyer shirt and tie," Jenny said with a smile.

Darlene looked over her shoulder as Jim and Jenny walked back into the room. Her eyes were just as red as before they left and she was still sobbing.

"Darlene, Jenny has convinced me to give you another chance."

Darlene turned to Jenny with a shocked look on her face. "Really," she said.

"Yes, but you are on trial. I don't expect to see any more devious acts of sabotage or any resentment toward Jenny. If I do, I will fire you immediately."

"Oh God, thank you."

"Don't thank me, thank Jenny."

Darlene turned to Jenny then put her head down and looked at the floor and whispered "thank you".

"Alright, now I've got to get some work done," Jim said.

Darlene jumped up and hurried out the door almost as if she were afraid that Jim would change his mind.

"Thank you sweety," Jenny said and walked over to Jim and kissed him on the lips.

"I hope you are right about this," he said.

"I know I am," Jenny answered.

Chapter 4

It didn't take Jenny long to get Darlene to open up to her. They went to lunch twice and went out one evening for drinks. It was obvious to Jenny that Darlene had needed someone to talk to for a very long time.

Darlene had been raised in a very strict and religious family. She knew nothing of boys or relationships. She wasn't ready to be in the outside world by the time she went off to college. In her second year Darlene was raped. She had been out on a date with a football jock when she agreed to go to the lake and watch the moon on the water. She thought it was just innocent fun. However, the boy thought it as an invitation. While she struggled and fought, he was much stronger.

The rape devastated Darlene. She knew that she couldn't tell her family and going to the police was out of the question. Even if they believed her she would be humiliated beyond belief. The school certainly wasn't going to punish one of their star players. Instead she took her pain in silence.

Darlene ended up leaving college a few weeks later. Her parents were very angry with her and practically disowned her. It didn't take long for Darlene to give up trying to live at home. She left and moved to the city and got her first job with the law firm. While she was suspicious and afraid of men, she eventually warmed to Jim. She wasn't sure when it happened but at some point she fell in love with him. She knew he would never look at her because he was already happily married. Then when Jim's wife died, she tried to be there for him but he never seemed to notice her. She knew that wasn't all his fault. She dressed in drab clothes and wore her hair in an old fashion way. Consciously or unconsciously, she was trying to discourage men. It worked very well for years. Not even Jim noticed her as a desirable woman.

Jenny listened carefully to Darlene. She was pretty sure that she knew what Darlene needed but she wanted to be careful. She wasn't psychologist but she knew people. It was obvious that Darlene was a very fragile person that had put a shell around her for security. It was also apparent that she didn't hate men; she was just afraid of them.

They were sitting in the bar with a couple of drinks between them when Jenny began to lay out her plan for Darlene.

"Darlene, do you trust me?" Jenny asked.

"Yes, I believe I do," Darlene answered.

"Are you ready to do what Jim has done and put your demons behind you?"

"I would love to but I don't know how."

"I do and I can show you if you are willing to do everything I say. Are you interested?"

"Yes?" Darlene answered without hesitation.

"Okay, we start tomorrow. Here's my plan," Jenny said and told Darlene what she thought she needed to do to change her life for the better.

Darlene was shocked to say the least. What Jenny was suggesting was so foreign to her that at first she couldn't believe that she had heard her correctly. She couldn't possibly do what Jenny was telling her that she needed to do. Yet she felt a little thrill run through her. The fact was that she was tired of always being afraid of men. She was tired of her boring life. She was tired of being Miss nobody. After a lot of discussion and soul searching, Darlene agreed to do as Jenny asked.

Jenny stopped into Jim's office the next day. "Jim, can Darlene have a couple of hours off this afternoon?"

"Why? I have lots of work for her."

"I want to take her shopping. Trust me on this sweety," Jenny said with her beautiful eyes sparkling.

"Alright but not all afternoon."

"Great, bye," Jenny said and kissed Jim quickly and ran out to get Darlene.

Several hours later Jim was sitting behind his desk wondering what had happened to the two women when he looked up to see a beautiful woman standing in the doorway. She was wearing a tight white sweater that buttoned down the front, with the first couple of buttons undone, a tight, short black skirt and four-inch high heels. Her hair was short and brown and professionally styled.

"Yes, may I help you?" Jim asked. When the woman didn't answer, Jim stood up. Then he saw Jenny peek around the corner of the doorway. Suddenly it dawned on him. No, he thought, it couldn't be.

"Hi Mr. Lewis," the woman said. "Do you like?" she said and turned around is a circle.

"Darlene?" Jim said, his eyes as wide as saucers.

"Close your mouth Jim," Jenny said as she pushed Darlene into the office and closed the door. Jim didn't see her turn the lock.

"My God, I...I don't know what to say Darlene. You look gorgeous."

"Thank you," Darlene said, her face turning red.

"She is gorgeous isn't she?" Jenny said. "Jim, Darlene has shared a lot of very personal things with me. Most of it, you don't need to know. However, Darlene is very sorry about what she did and she wants to make it up to you. Don't you Darlene?"

"Uh...yes," Darlene said shyly.

Jenny walked around Jim's desk and pushed him into his chair. "Come here Darlene," Jenny ordered.

Darlene walked hesitantly around Jim's desk and stood in front of the seated man.

"Come on Darlene, I'll help you," Jenny said.

Jim watched in wide-eyed amazement as Darlene slipped to her knees at his feet. He looked up at Jenny's smiling face and said, "What the heck is...?"

"Shhhhh," Jenny said. "Go ahead Darlene."

Again Jim watched as Darlene reached up, her hands shaking, and began to open his pants. "My God Jenny," Jim said.

"That's it Darlene, don't be afraid, take his cock out."

It was Jim that was beginning to shake as he watched the beautiful woman between his legs open his pants then reach her hand into his shorts. Both he and Darlene jumped when her cold hand touched his hot cock. As she pulled it from his pants it began to harden.

Darlene couldn't believe that she was doing this. Yes she had fantasized a million times about holding Jim's cock in her hand but she never thought it would happen. She could feel her heart pounding in her chest as she watched his cock grow in her fist. She began to move her hand up and down as Jenny had told her to do. When she heard Jim moan, she knew that she was doing something right. Jim's cock was everything Darlene had thought it would be. It was only the second cock she had ever seen. The shaft was longer then she had pictured and the head was a deeper purple. When she squeezed and moved her hand up, a large drop of clear liquid appeared on the slit. She looked up at Jenny and saw her nod her head. With a little moan, Darlene leaned forward and used her tongue to lick the drop of juice from the head of his cock.

"God Jenny," Jim moaned as he watched his assistant of nine years lick his cock.

"Suck it Darlene," Jenny ordered.

Darlene hesitated for just a moment, gathering courage. She opened her mouth and covered the head of Jim's cock. She heard Jim moan again as she held it in her mouth. Darlene was so excited that she could hardly breath. She tightened her lips around the head and began to suck, her cheeks pulling in.

Jim thought that Darlene wasn't very good at this yet but the fact that she was obviously new to this made it incredible exciting. Jim tried not to buck his hips up as he felt Darlene's tongue begin to work on the little slit in the head. "Ohhhh," Jim moaned as he watched her suck him.

"Lick it," Jenny said.

Darlene released Jim's cock from her mouth and held it up in front of her face. Her eyes were glazed over with lust as her tongue came out and began to lick his cock from bottom to top. She held his cock tight and licked it like an ice cream cone.

Jim was delirious with pleasure by this time. He watched her wet his cock with her tongue until it was dripping with her saliva.

"Open your sweater Darlene," Jenny said.

Darlene sat back and slowly began to open her sweater. Her hands were shaking as she fumbled with the buttons.

Jim hadn't even noticed how large Darlene's breasts were. Now he saw that they were positively huge. He sat there and watched as she opened one button at a time.

Darlene held her head down, not daring to look up for fear they would see her red face. She opened each button until her sweater was open, exposing the area between her breasts, all the way to her navel.

When Darlene didn't move to pull the sweater back from her breasts, Jenny walked around behind her. She felt Darlene tense as her hands touched her shoulders. Slowly Jenny slid her hands down and over her breasts, lightly touching each one. Jenny was surprised when she felt Darlene's nipples harden and her body shiver. She grasped the sweater and pulled it back, freeing Darlene's large breasts.

Jim gasped as he looked down at the prettiest pair of tits he had ever seen. They were creamy white, obviously never seeing the sun. The nipples were positively huge, covering much of the front of her tits. Jim felt his cock throb as he stared at her.

"Aren't they beautiful," Jenny said. "I saw them in the dressing room. I couldn't believe what she has been hiding behind those baggy clothes." Jenny pulled on the sweater, then pushed it down Darlene's arms and dropped it to the floor.

Darlene had yet to look up, her face beet red. Her chest was heaving with excitement from the pair of eyes looking at her bare breasts. She had never been so excited in her life. She felt a little shiver of pride go through her as she saw Jim's cock twitch from looking at her breasts.

"Rub your tits on his cock," Jenny said.

Darlene jumped from the sound of Jenny's voice. Without looking up, Darlene moved up onto her knees and leaned forward. She gasped as she felt her tits touch Jim's hot cock. She saw Jim scoot down in the chair, giving her a better angle. Darlene used her hands to lift her heavy breasts and begin to rub them across Jim's cock.

Jim still couldn't believe he was watching his demure assistant rubbing her breasts on his cock. He would have never believed this in a million years. The pleasure of her smooth skin on his cock made him want to close his eyes, yet he didn't want to miss anything so he watched. He watched Darlene take one tit and rub the hard nipple across the head of his cock, smearing his juice around. Then he had to moan when she squeezed both breasts around his cock, encasing it in her warm soft tit flesh.

"Does that feel good darling?" Jenny asked.

"Oh God Jenny...oh God it's wonderful," Jim said as he watched Darlene begin to move her tits up and down.

"Suck his cock Darlene. Suck it as you squeeze your tits on it," Jenny said as she watched from over Darlene's shoulder.

"Mmmmm," Darlene moaned as she opened her mouth to take Jim's pulsing head inside. She continued to move her tits up and down as she began to suck the head hard, using her tongue to cover the soft skin with butterfly licks.

"Oh my God, Darlene, oh God, wait...uh...please...I'm getting so close," Jim moaned in warning.

"It's okay sweety, you can cum. Darlene wants to drink you juice, don't you?" Jenny said.

"Mmmmm," Darlene moaned again, her mouth full of cock. She felt her heart beating wildly at the thought of Jim cumming in her mouth. She had fantasized so many times about him cumming in her mouth and now it was going to happen. Pressing her tits tighter around his cock, Darlene began to suck hard.

"Oh yes, ohhhh...I'm going to...oh here it cummmmssss!!!" Jim moaned as his cock began to throb. He could feel his cum leave his balls and begin to rush up the shaft. It felt like his cock head was going to explode as it throbbed and began to squirt his juice into Darlene's willing mouth.

Darlene felt the first pulse and prepared herself like Jenny had told her too. She closed her throat so she wouldn't choke. Her mouth filled quickly and she swallowed the first taste of cum she had ever had. Suddenly she felt her pussy throb. She snapped her knees shut as her body began to shiver. By the time the second shot of cum hit her mouth she was climaxing herself. She had never been that quick to cum, even with her experience hand.

Suddenly the only thing in the room was Jim's squirting cock and her throbbing pussy. It felt like his cum was running into her stomach and right to her pussy. Her own cum juice was running down her legs. She kept on sucking and swallowing until she heard Jim moan and begin to push her mouth from his wilted cock. When she pulled back, she saw Jim's cock between her tits, dripping his cum. She licked the last drop off his cock and swallowed one final time. Her mouth tasted like Jim. She loved the taste.

"Wow," was all Jim could muster. He looked down and saw Darlene look up at him for the first time since she had began to suck him. She used the back of her hand to wipe her mouth then she smiled shyly.

"Come on Darlene, we have a hot date for you tonight and we don't want to be late," Jenny said as she helped Darlene get up and put her sweater back on. Jenny blew a kiss to Jim and winked. "I'll call you later tonight," she said quietly as she went out the door.

Chapter 5

Jenny sat in Darlene's bedroom waiting for her to come out of the bathroom with her new outfit on. She had arranged for her friend Jay to pay them a visit. Jay was one of Jenny's lovers. He was a physical fitness instructor at a local athletic club. Jay was also gorgeous. He could have been a model but he didn't like the pretentiousness of the modeling business. Jenny had never had a more gentle or skilled lover. He knew all the parts of a woman's body and what made them tick. She knew he would be perfect for Darlene.