Jack and Molly Ch. 02: Nervous Step

Molly saw him first. He wasn't like any famously handsome movie star, but he wasn't ugly either. He seemed a little better looking than an average guy his age. His salt and pepper hair gave a distinguished look; and she liked his mustache. He had a tummy, but not so big to get in the way. The last time she saw him, she noticed his hazel green eyes - nothing to write home about, but she liked the way he looked at her. He gave her the once over from head to toe, but only to make a point about how beautiful he thought she looked. Otherwise, he kept his eyes on her face, and listened with great interest to her every word. She enjoyed the emails they exchanged. He didn't write dirty, but with respect, and a little mystery.

Jack was looking forward to tonight. They didn't get to meet sooner because of family events in each of their lives. But finally tonight, he hoped she was warming up to him and wanted to play. He had been working on ideas for the evening, but they might need to wait for another time. They only had a couple of hours since they were both expected home later. He hoped she had similar expectations as he did. The very few women he had talked to online wanted more than he was willing to give.

She waited until he noticed her, and he walked over to her.

"Is this seat taken?" he asked with a smile.

"You can have it," she said. "I was waiting for ...". She didn't know how to flirt, so was at a loss for words.

"Well, whoever it was, I hope he never shows and steals you away," said Jack. They both laughed nervously.

"I feel so stupid," said Molly.

"Why? Don't feel that way. Just feel beautiful," said Jack.

"Thanks," she said.

"Do you want to stay here and get a drink, or go find someplace a bit more private?" asked Jack. "That just sounded liked a cliché pick up line," he said, and they both laughed again.

"Let's get out of here. I'm afraid someone will recognize me," she said.

"I agree. Let's go," said Jack.

They headed for his car, got in, and started driving.

"Let's find some quiet place where we can talk", said Jack. Both were hoping for something more than talk. They engaged in a little chit chat on the drive, both still somewhat nervous. The last time they saw each other, he had playfully dared her to video record herself stripping in the bathroom on her phone. Surprisingly to the both of them, she did it! Since then, they emailed a little back and forth, but not too much. He said he had some ideas to make things fun, and only gave hints. Tying her up and giving her orders seemed to be a strong interest of his. She challenged him on this, but when he asked her what her ideas were, she drew a blank. Frankly, she found it easier to let him use his imagination. But the idea of being dominated did have some appeal.

They found a spot in a large parking lot away from the stores. It was dark outside, and this area was not as lit than the rest of the lot. It seemed like a decent place for some discrete fun, should they decide to try something. And both were hoping for, "something".

Molly was reluctant to ask, but dared say it. "Are you going to tie me up here?"

"Do you want me to?" Asked Jack.

Molly didn't know what to say and got very nervous.

After a long pause, Jack broke the tension and said, "I didn't bring my handcuffs. Are you disappointed?"

"I guess," said Molly, half relieved, and half disappointed, and a nervous smile.

"But you like me to be a little bossy, though. Right?" he asked.

"I guess," said Molly, recognizing she wasn't being much of a conversationalist at the moment.

"Then how would you feel if I put my hand on your leg. Would that be ok?"

After a long pause, she said, "I guess so," slightly expanding her vocabulary.

He put his right hand on her leg and lightly caressed it. Molly stiffened nervously and found herself taking shorter breaths.

"Well that was fun," said Jack. "Shall we go home now?" Molly looked at him with surprise, relief, and ever so faint disapproval.

"Just kidding," said Jack, as he turned his body toward her, put his right hand on the headrest behind her head, and placed his left hand where his right hand was, then moving it faster on her leg, and further up her thigh. She turned away, partly in reflex of her modest upbringing. He recognized she was excessively nervous. Not the fun kind with anticipation. He had not yet built up enough trust, so this was the bad kind of nervous. The kind of nervous that might make her bolt. He needed to calm her down.

"Let's get out and walk," said Jack. He figured this would give her some personal space that she would appreciate, as well as a better way of seducing her more calmly.

They got out of the car and walked side by side along the edge of the lot. There was a walkway with some trees that made things look aesthetically pleasing.

"Are you nervous," asked Jack.

"Yeah, I think I am," answered Molly.

"That's ok," he said. "I understand. I feel some weird feelings myself. This isn't something I do on a regular basis. It is one thing to fantasize about being with a beautiful woman. It is a whole different ballgame when she's actually in your presence."

That made her smile. He was trying to be respectful, encouraging, and complimentary. "Gotta give him credit for trying," she thought.

After a few minutes, he figured she was calmer. "May I give you a hug?" he asked. She stopped and said, "sure." He held her close and didn't rush it. They both just enjoyed the simple act of affection. "That felt good," he said. "Yes it did," she agreed. Then started walking side by side again.

"Do you still have that video," he asked. She looked and him, smiled, and answered playfully, "maybe."

"Let's see it," he said with a smile.

"Noooo," she said, like a whining child. "It's embarrassing."

"I know, but it's just between the two of us. You can show me," he urged.

"I'm not going to show you!" she said with a smile. "I don't want you seeing my boobies."

"What?" he exclaimed. Would you rather I just help myself," he said, turning toward her and reaching out with both hands toward her breasts. She turned away and giggled. "Stop it!" she laughed. "Those are mine."

"Aw. I thought you were the sharing type. Didn't you learn that in kindergarten, to share?"

"I don't share Everything," she said.

"Come on," he taunted. "Don't you want to feel my hands on your body?"

She wasn't sure how to answer that. "You're just like all the other boys."

"Ouch", Jack said, as he playfully clutched his heart and started to swoon. Again, they both laughed.

As they walked behind a tree, He stepped behind her and grabber her from behind, hugging her around the stomach. "Come on, pretty lady. Share with this boy."

She stopped, still smiling. She didn't answer, but didn't pull away either. It was dark, and they were mostly hidden, and feeling his hands on her breasts had been on her mind. So as he slowly raised his hand to cup her breast, she didn't protest. Instead, she instinctively put her hands on top of his and tilted her head back and rested it on his shoulder behind her. His hands felt good. She eventually lowered her hands as he continued to gently knead her mounds.

"You feel good, but there is something in the way," said Jack. She said nothing, so he lowered his hands and slid them under her untucked blouse, exploring her stomach for a minute before bringing them behind her to unhook her bra. He got lucky, he didn't have to fumble, and it unhooked quickly. He slid his hands around to the front and again raised them up and over her nipples. After a moment he said, "you feel very nice." She answered with a moan of pleasant approval.

After a couple of minutes of mutual pleasure, Jack said, "too bad I don't have a rope or maybe I'd tie you to that tree and have my way with you."

"You'd like that, wouldn't you," she said.

"And you wouldn't?" he retorted. "Maybe one of these days, I'll do just that and see how you respond." The idea sounded exciting, but she wasn't sure she would be comfortable enough to go along with it.

"You wouldn't dare," she said.

"Is that a challenge?" he asked.

She wasn't sure how to respond, and was afraid if she said the wrong thing, he might take his hands away. All she could do was softly grunt.

After another couple of minutes of massaging her breasts and tugging at her nipples, he slid his hands down and slid them under the back of her skirt and cupped her ass, along with little squeezes, before moving them to the front and exploring the area covered by her panties.

"When's the last time you had an orgasm?" asked Jack softly into her ear.

After a pause, Molly answered, "the night I met you at the bar."

"Ok," said Jack, "when was the last time a Man gave you an orgasm?"

"It has been a long time," Molly reminisced. "A Very long time."

"How do you feel about my helping you with one tonight?" Jack asked.

"What do you mean?"

"I mean we go back to the car, you get rid of this little thing in the way," said Jack patting the front of her panties, "and we'll see if my fingers have any magic."

Molly didn't want to appear to be too anxious, so she delayed her answer, but finally said, "I suppose."

Jack removed his hands from beneath her clothes, and grabbed one of her hands as they walked back to the car, perhaps a little faster than the stroll they just took.

Jack opened the door and Molly got in. Jack got in on the driver's side and once again had his left hand on her right thigh. "You need to get rid of that bra. It's in the way."

Molly reached under her blouse and pulled out her bra, putting it in her purse.

"Same with your panties," said Jack.

After a slight pause, and feeling a quite a bit bolder, she said, "maybe you'd like to help with that?"

Jack smiled, feeling the blood rush to his face, then reached under her skirt and started probing with his fingers, looking for the waistband of her panties. Upon finding it, Molly moved her hips up to allow him better access and getting it off her waist and down her legs. Jack put it up to his nose and sniffed.

"Give me that," snapped Molly with a smile as she snatched them from his hand and stuffed them into her purse.

Jack laughed and said, "you smell good." Molly blushed. Jack reached back under her skirt and began exploring. They fixed their eyes, staring at each other, watching to see how each responded to whatever Jack discovered. Jack's fingers slowly made their way closer to their target as he continued caressing her legs and pelvis. Then, a finger momentarily found its outer target, and Molly raised her eyebrows, and the corners of her lips. He continued his general area exploration before returning another pair of fingers to the outer target, resulting in another raised eyebrow from Molly. Jack narrowed the range of exploration and began to slowly caress her outer lips for a minute. Further slowing his pace, he allowed his fingers to rest on her outer lips, before he began to spread them and insert his fingers into the moist opening. Molly closed her eyes. In a small circular motion, Jack continued his massage and Molly leaned back and relaxed in her seat.

When his fingers touched their next target point, Molly took a short breath with a slight tightening of her muscles. His fingers continued to sink a little deeper, circling the edges of the passageway. With his middle and ring finger submerged, his thumb was able to find the nub that invoked a slight irregularity to her breathing. Jack continued exploring, massaging, gently pinching and pressing, with some rhythmic motion, causing her to flood his fingers with her juices. Both the motion of his fingers, and her rate of breathing, became increasingly faster and more energetic. Her heavy breathing morphed into groans and gentle whimpers. "Oh God," she moaned, and continued getting louder. Her hips began moving more and faster, as her breathing continued an irregular pattern, indicating strong feelings and uncontrolled spasms were invading her being. Moments later, she clutched his hand and pressed it against her bounding hips, gasping, and let out a guttural groan to signify her orgasm had reached its climax and eventually began receding.

Jack removed his hand, wiped it on a nearby towel, put it on her far shoulder, and held her still while he leaned over and gently kissed her. "That was fantastic," Molly said. "It has been a long time."

"Promise me two things," Jack said. "That this won't be the last time you let me do that to you..."

"Oh that's easy," she said.

"...and that you will teach me what I can do to make it better next time."

Molly wasn't so quick to agree to that, since talking about those things were a little outside her comfort zone.

"Please promise me?" pleaded Jack.

"Ok, we'll see," said Molly, but submitting to the idea that she might need and want to talk to him more about these things.

"I still want to hear what you might like me to do to you," said Jack. "I told you what I what I like."

"I like it when you take charge," she confided in him.

"I see. Then I guess I'll have to think of something," he said with a devilish smile.

After a little more talk, she got dressed, and he drove her back to her car. They kissed each other good night, and they drove away, nervous, yet excited to see what their next meeting would bring next time. Actually, Jack already knew. He hoped she liked it.

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Again, feedback welcome and appreciated, both the encouragement, as well as the recommendations for improvement. I especially value the ladies' comments about realism and how much you would enjoy such an encounter.