A Second Chance At Love

"No, I would love it," Jim said, a little too eager. He felt his face flush again. Then his eyes grew wide as she watched Jenny turn and stretch to place her coffee cup on the coffee table behind her. As she reached back, her legs parted, giving Jim a perfect view directly up her dress. He almost let out a moan as he saw her smooth thighs above her thigh high nylons and the silky crotch of her pink panties. She seemed to take a long time placing the cup on the table before she turned back to Jim. It spite of himself, Jim felt himself getting hard as he saw her legs stay wider then was ladylike.

The two talked for a while longer before Jenny said, "Well, I guess I had better get back downstairs or my supervisor, 'Mildred the terrible', will have a cow."

"Oh, I hear she can be a shrew," Jim laughed. "Uh...uh...would you, that is if you don't have plans, like to...uh you know...go to..." Jim stuttered.

"Go to lunch? I'd love to," Jenny said finishing Jim's sentence for him.

"Oh great, I'll stop down at noon," Jim said excitedly.

"Wonderful, I look forward to it," Jenny said, her smile lighting up the room.

Jim and Jenny went to lunch that day and three more times before Jim got up the nerve to ask her out. He was very disappointed when she said that she would have to think about that. Then he chastised himself for ever thinking that a young beautiful girl like her would ever want to go out with a 38 year old man.

Jenny just needed a little time to think. She was growing to like Jim. However, there were a lot of reasons why she should say no. He was sweet and handsome but too old for her. Besides, it is rarely a good idea to start a relationship with someone that you work with. Then Jenny thought, what the heck, it is only a dinner, she could control things.

Jim was ecstatic when Jenny called the next day and accepted his offer. He was walking on clouds the rest of the week. As Friday neared, he became more nervous. However, the date went wonderfully. Jenny made him feel very comfortable and really acted like she was interested in what he had to say. When the date ended, Jim was not presumptuous enough to kiss her good night, no matter how much he longed to do it.

Jenny thought Jim was so sweet. He put no pressure on her to take the relationship further. That was a refreshing change from her normal dates. She decided that she liked him a lot.

On the third date, Jim stood outside Jenny's apartment saying good night. He was unusually nervous. Finally, he blurted out, "Do you mind if I...if I...uh, kiss you good night?" he asked with a red face.

"Of course you can kiss me, I thought you would never ask," Jenny said, her eyes sparkling.

Jim sighed in relief and took her into his arms. His head was spinning as he smelled her perfume and held her soft body close to him. He could feel her soft breasts pressing to his chest as his lips met hers. Jim was a little surprised when Jenny pressed her tongue into his mouth. He moaned quietly and began to suck. When Jim pushed his tongue into her mouth, Jenny opened wide and accepted it, sucking hard. Suddenly Jim was mortified when he felt his cock begin to harden in his pants. He thought about pulling his hips from her to hide his excitement. But he was relieved when Jenny pressed her body tightly to him, squeezing his now hard cock to her stomach.

Jenny moaned in spite of herself when she felt Jim getting hard. She was in an emotional turmoil. Normally she would pull her date into her room and fuck his brains out. She knew that Jim was different; she knew that he needed time to get used to a relationship with a woman again. Besides, she was not sure of her own emotions. They had already gone far beyond where she originally felt comfortable. However, there was something about Jim that drew her to him. In could be that he was such a gentleman and was so different from the pawing she typically got from her dates. Not that pawing was bad she thought. It was just nice not to have to be pressured to go to bed with someone.

When Jim pulled away, his breathing was a little heavier, his cock throbbing like some teenager on his first date. He hoped that Jenny didn't look down; she would surely see the wet spot on his pants.

The truth was, Jenny's panties were wet as well.

Over the next month, Jenny and Jim dated several more times, each time Jim kissed her at the front door. Jim wanted to go further but was afraid of the rejection.

Jenny was unsure where she wanted the relationship to go. She felt sexual excitement with Jim but she had her other lovers and she felt free to be as sluttish as she wanted with them. She wasn't sure how Jim would react if she knew the real wanton slut inside her. Jenny was not ready to give up those lovers under any circumstances.

Jenny didn't want to be cruel to Jim. She knew that he needed some relief, she just wasn't sure what that meant or how far to go. With her regular boyfriends there was never any question. Maybe a little petting would be okay with him she thought. But she wasn't sure when or how to initiate it without scaring Jim off. Then she got an opportunity that she was looking for when Katie, her roommate, suggested a double date.

Katie was a pretty brunette who had been Jenny's sorority sister and roommate through college. When they graduated they decided to rent a house together and share the expenses. Katie was dating an older man and seemed to prefer them. She and her boyfriend Jerry were sexually active and would often go to her room and make love through the night.

Jenny didn't think that she liked Jerry. He had been married when Katie and he met. Jenny didn't want to be judgmental but she wasn't sure what Jerry's intentions were. There was just something about him that didn't sit right with her.

Jim readily agreed to go out with Katie and Jerry. He wanted to get to know Jenny's friends.

They went to a movie and then had a quiet dinner at a nice Italian restaurant. They all laughed and joked, the conversation flowing easily. Everyone seemed to get along well, even if Jerry and Katie had drunk a little too much. That was okay since Jim had driven.

On the way home, Katie and Jerry sat in the back seat as Jim drove with Jenny snuggled close to him. The restaurant was in another town and they had a bit of a ride home. Jenny and Jim talked quietly in the front seat as Jerry and Katie whispered in the back. Suddenly Jenny heard a moan and looked back to see Katie and Jerry kissing with Jerry's hand inside her blouse playing with her tit. She suppressed a little moan as she watched the lover's kiss and Jerry's hand move freely under her blouse.

Jenny turned quickly back to face the front and giggled. Jim looked over at her with raised eyebrows. She snuggled closer to him, her hand dropping to his thigh. As they drove, the moans in the back got louder and louder until the two in front could no longer deny what was going on in the back seat. Jenny looked back again and gasped when she saw that Katie had Jerry's cock out of his pants and was about to suck it. She turned back, her heart thumping in her chest. When she looked down, she saw that Jim's cock was tenting his pants.

Jim was shocked by what was going on in the back seat of his car, even if he couldn't see it. He looked in the rear view mirror but could only see Jerry's head thrown back on the back of the seat. Suddenly he jumped when he felt Jenny's hand moving slowly up his thigh. His heart was beating wildly. When he looked at the speedometer, Jim realized that he was going well over the speed limit. He had to slow down or risk getting a ticket.

Jenny looked back again then turned and kissed Jim's neck as her hand covered his cloth-covered cock. She felt Jim tense and a shiver run through his body. Then Jenny shocked Jim even more by reaching over and slowly pulling his zipper down.

"Jenny, what are you doing?" Jim whispered, his voice shaking.

"Shhhh!" Jenny said as she reached into Jim's pants and fished his cock out. "Oh my," she said as she looked at Jim's pulsing cock. It was a nice cock she thought, not to long or too big around. It would fit in her pussy very nicely if that time ever came. She heard Jim moan as she squeezed his cock, bringing a large drop of clear juice to the head. She used her finger to rub the juice across his swollen cock head. Her other hand began to move up and down.

Jim couldn't believe that he was driving on the freeway with his cock out of his pants and in the hand of his young date. He also couldn't believe what was going on in the back of his car. From the loud sucking sounds, Katie must be giving Jerry a blowjob. He was trying desperately to concentrate on driving as Jenny began to move her hand up and down on his very excited cock. "Jenny, God," Jim said, almost in desperation. His heart was pounding in his chest as Jenny used one hand to wrap her fingers around the swollen head and used the other to jerk his cock. He was surprised to see Jenny looking into the back seat.

Jenny watched her friend suck on her lover as she masturbated Jim. Her own pussy was pouring juice into her panties. She couldn't believe her friend was giving her date a blowjob right in the back seat. She and Katie had done a lot of wild things but never anything this bold. Suddenly she heard Jim moan, almost a whine. She looked down and saw that his cock head had grown even larger and was pulsing. She quickly put one hand over the head, just in time to stop Jim's cum from shooting all over his shirt. She used her other hand to jerk on the shaft, her breathing as labored as if she were climaxing herself. In fact she felt a little shiver in her pussy and a climax run through her as Jim's cock continued to pump his cum into her hand before it ran down his shaft.

At the same time in the back seat, Jenny saw Jerry push his hips up, forcing his cock deep into Katie's mouth then groan. She saw her friend sucking and swallowing her lover's cum.

Jenny cleaned up Jim's cock as best she could and put it back into his pants. She smiled at her startled date and put her head on his shoulder. The four of them were quiet as they finished their ride home.

When they reached home Katie and Jerry went into the house leaving Jenny and Jim outside the door.

Jim was quiet for a while. He took Jenny into his arms and kissed her passionately. "Thanks," he said, totally at a loss as to what to say to a woman that had just jerked him off.

"My pleasure," Jenny whispered as she snuggled into Jim's chest. They kissed one last time and said good night. Jenny went into her bedroom and masturbated several times as she listened to Jenny and Jerry moan in pleasure long into the night.

Chapter 5

Jim was in seventh heaven the following morning. He felt like a kid again. He couldn't believe that he had let Jenny jerk him off in the car, like some horny teenager. Yet that was almost how he felt. Still, somewhere deep inside there was this little nagging issue concerning their age difference. Jim was becoming infatuated with Jenny but he wasn't sure how far it could go.

Jenny sat at her desk with the same thought in her mind. She was beginning to like Jim too much. Yet, he wasn't really her type, he was so na‹ve. But then again, she thought it was kind of cute. However, she had never dated anyone as old as him and she wasn't sure she wanted to become attached to an older man. Or, any man for that matter. She liked that she was a free spirit and that she took sex wherever she found it. Jim wasn't very adventuresome. She was sure that he was mortified this morning about the hand job. Still, she giggled to herself as she thought about what she had done. It had been great fun. She felt a little thrill shoot through her when she remembered watching Katie sucking on Jerry's cock as she jerked Jim off. It was almost too much for her to watch her friend drink her lover's sperm as her date came in her hand.

On her way to the bathroom, Jenny had a naughty thought. At first she dismissed it as crazy but the more she thought about it the more excited it made her. She decided to have some fun with Jim. She went into the bathroom to take her panties off. When she started to pull them down she stopped as another naughty thought occurred to her. Instead of taking them off, she pulled them up tight to her crotch. She looked down to see the material plastered to her pussy lips. The silky blue panties were so tight that they outlined her pussy lips like a second skin. As she walked to Jim's office, she could feel her pussy juice begin to wet the crotch.

Jim looked up when he heard a light tap on his opened door. He smiled when he saw Jenny. "Come on in," he said. Suddenly a flush came to his face as her remembered last night.

As usual, Jenny looked great. She had on a short summer dress that left her arms and shoulders bare, with thin straps holding up the wispy material.

"I'm not interrupting you am I?" Jenny asked as she sat down across the desk from Jim.

"No, not at all, I was just going to call you and thank you for last night," Jim said then felt his face turn red as he realized that it sounded like he was thanking her for a hand job. "I mean...uh...for the uh, date, it was fun," he stuttered.

"I had a good time also," Jenny answered with a knowing smile. "I do think Kate and Jerry got a little carried away," she added, "but it was really hot watching them.

"Yea, I guess," Jim said, not really knowing what else to say. "Would you like something to drink?" Jim asked, trying to change the subject.

"Yes, thank you, a Coke would be great."

Jim went over to his bar and got her a Coke and a glass of ice and handed it to her.

"Do you mind if I ask you some legal questions?"

"Not at all, fire away."

Jenny asked Jim several questions about the law. They were questions she already knew the answers to. She was just making conversation; the legal process was not what was on her mind. As Jenny relaxed, she sat back in the chair. Slowly, almost absent-mindedly she opened her legs slightly.

Jim immediately saw her legs begin to open. His eyes grew big when he realized that he could almost see all the way to her crotch again.

Jenny turned and looked over her shoulder to make sure Jim's secretary, Darlene, was at her desk, facing the other way. Before she even turned her head back, her legs opened as wide as her skirt would allow, exposing her entire crotch to Jim. She could feel the cool air on her now very wet panties.

"Oh God," Jim said under his breath as he looked at Jenny's exposed panties. He could see the entire shape of her pussy, every fold of flesh. There was a very dark stain in the center of her pussy lips.

"So do you have a busy day today?" Jenny asked like nothing unusual was happening.

Jim swallowed hard, his mouth becoming very dry all of a sudden. "Uh...it...uh I guess it will be busy," he managed to choke out, his eyes never leaving Jenny's pussy. He watched in amazement as one of her hands slid slowly up her thigh, over her thigh high nylons, to play with the soft skin between the nylon top and her pussy. Her fingers casually rubbed the soft skin, inching closer to her panty-covered slit.

Jim's cock began to harden as he watched the wanton display before him. He couldn't believe the boldness of this woman. His cock was pulsing in his pants as Jenny's finger reached her slit.

Jenny's face was flushed as her finger pressed the crotch of her panties deep between her lips. She slid down in the chair slightly, causing her skirt to ride up higher allowing her legs to spread further.

"Mr. Lewis," Jim secretary said, standing in the doorway.

Jenny snapped her legs closed and sat up quickly.

Jim looked up, his face turning beet red.

"Uh yes, Darlene," Jim said trying to recover from his shock.

"Mr. Wilson is on the line, he says he needs to speak to you right away."

"Well, I was just leaving," Jenny said with a sweet smile. She stood and walked past a frowning Darlene.

Chapter 6

Jim had a very hard time concentrating the rest of the morning. It was almost eleven thirty when Darlene brought a large expandable folder into his office. It had confidential written in large red letters across the front flap. Jim thanked Darlene and took the envelope. He untied the string holding the flap down and opened it. Fortunately, Darlene had left before he opened it or she would have heard him gasp.

Inside the envelope, Jim saw a pair of blue panties. He quickly got up and went to the door and told Darlene that he did not want to be disturbed for a while. He closed the door and sat down at the desk and opened the envelope again. His hands were shaking as he pulled the silky material from the folder. He opened the panties and saw that the crotch was still wet and sticky. A little note dropped to the floor. He reached down and picked it up, his heart pounding in his chest.

"Hi sweety, I know you like my panties, I saw you looking. I thought I might give you a pair. Unfortunately, I don't have a clean pair but I didn't think you would mind. Love and Kisses J"

Jim groaned and brought the panties to his nose and inhaled deeply. His cock throbbed as he drew in the musky woman smell. Almost without his control, Jim opened his pants and freed his hard cock. He carefully wrapped Jenny's thong panties around his cock, the wet crotch covering his dripping cock head. Jim began to move the panties up and down as he slumped in his chair. His thoughts went back to the drive home last night. He could still hear the sucking sounds and the moans from the back seat. He could feel Jenny's soft had on his cock.

Suddenly, Jim's balls tightened and his cock began to spit his cum into the already wet crotch of her panties. He closed his eyes and moaned as his juice filled the small crotch of the silky panties he held tightly around his cock.

Jim sat there for several minutes breathing heavily. Here he was, a big corporate attorney, jerking off like some adolescent. While he felt ashamed at what he had just done, he couldn't deny that it was very pleasurable. A little tremor ran through him when he remembered Jenny sitting in front of him with her legs spread and her fingers in her crotch.

Jim removed the now saturated panties, wondering what he was going to do with them. Then a naughty thought came to him; two could play this game. He wrote a little note and placed the panties back inside the folder. He sealed it and addressed it to Jenny. Then he took it out to Darlene and asked her to personally deliver it to Jenny downstairs.

As she walked away, Jim thought if she only knew what was inside?

"Mr. Lewis asked me to deliver this to you Miss. Bradford," Darlene almost snarled.

Jenny saw the package and her heart sank. "Uh, thank you," she said and took the envelope. As soon as Darlene left, she opened the envelope to see her panties. She thought that she had gone too far and that Jim had rejected her little gift. Then she saw the note on Jim's notepaper. She opened the note.

"Jenny, Thanks for the gift; it was very thoughtfully of you. However, I thought that you might need them back. Sorry that I couldn't clean them. Thanks again. Jim"

Jenny looked in the envelope in confusion. She reached in and pulled the panties out. This time it was her turn to gasp. Immediately she could see the cum dripping from the crotch. A large drop landed on her desk. She jumped up and rushed to the bathroom, her pussy throbbing as she walked. Inside the stall, she sat down to catch her breath. God maybe Jim wasn't so niave after all she thought.

She opened the panties she held in her hand and confirmed that Jim had indeed cum all over the crotch. Jenny was so hot that she was shaking. Without a second thought, she stood up and stepped into the panties then pulled them up her legs, pressing them tight to her dripping pussy lips. She could feel Jim's cum covering her swollen pussy. She sat back down and used her finger to rub the cum all over her pussy. When her finger reached her clit, she had to suppress a moan as her body convulsed and a strong climax hit her. Her legs tightened and she bit down on her lip to keep from screaming out as her body spasmed with pleasure. She had never cum that quickly in her life.