Jack and Molly Ch. 01: Intro Dares

As a frustrated, married man, I decided to express some fantisies that I though could actually occur in my life, considering I'm not a drinker, and don't really socialize much. Happy to hear your comments.

He saw her walk in the front door, and it somewhat surprised him. "Is it possible, on the first night? What are the odds?"

He had been sitting there for less than an hour wondering just how big a mistake he was making. He's not a drinker. He doesn't go out clubbing. He's over 50 - half a century - and almost certain there would be no one interested in him. After all, his wife treats him like a good friend, but can't confess that she has no desire. Yes, one of those sorry saps who has been stuck in the friend zone his whole life, including his marriage. Yes, there were some young women who had their eyes on him, but that was 30 years ago when he was a young engineer. Since he has been married, there have been a couple of older women who have expressed an interest in giving him a "happy ending" - he had to look that up - and more. But he remained a faithful husband...mostly. Ok, he'd been on Craig's List advertising for a platonic relationship, but kinda hoping for more. Turns out, very few understood the term "platonic". Those that did understand were repulsed by the topic of sex, with a single meeting for coffee, at the most. Those who did not understand the term were actually looking for more than he was willing to give.

He was a committed virgin until he married at age 33, falling in love with his wife before even meeting her or knew who she might be, and unwilling to compromise their intimate relationship before it had a chance to germinate. After their marriage, they grew in their relationship, though not too busy in bed. When they decided on a child, they did what was necessary, but it seemed more like a chore to him, in order for her to get pregnant. Since they decided another child for the family was necessary, they adopted. The activity of baby making was not of much interest to her, much to his frustration.

When he saw the woman at the door, there seemed to be something about her. She wasn't drop dead gorgeous. She wasn't trying to be a sexy slut. She wasn't trying to impress people into thinking she was an independent, self-made business woman. She had a simple appearance. She looks sweet, simple, and pleasant. She looked like she could be a mom. She looked pretty. She also looked out of place, as though she didn't belong there, and she knew it. She looked around, slowly, not really looking for anyone in particular, but just to get a feel for the place, and perhaps a place to sit. She also looked uncomfortable.

She found a table, removed her coat, and sat down, putting down her purse, but still looking around nervously. Her coat had done a great job of hiding everything below her chin. Before that moment, all he could see was her long chestnut hair. But when it came off, it revealed the pretty dress she wore underneath. As she moved, the dress outlined the almost hourglass figure hidden underneath. He could feel her uneasiness - it felt like his. Should he run over there and say hello, possibly scaring her away. Or should he wait, and let her get comfortable, risking that some other guy will beat him to introductions? Some women seem to like the suave, handsome stranger who can start slow and gentle, and expertly change his language to bring in sexy banter, eventually having her take his arm as they leave for a place a little more comfortable - knowing "talk" really isn't the objective.

"I expected to crash and burn before I got here, so why prolong the inevitable," he thought to himself. He stood up and walked over to her, his heart pounding.

"May I sit with you and pretend to save you from all the other guys who, without a doubt, would like to make a pass at you?" he said with a small smile, in his most un-intimidating voice he could think of.

"What?" she asked, with skepticism in both her voice and facial expression. But all he could see where her eyes. Those big, beautiful, brown eyes. They looked at him as though he was a teenager that just did something unthinkable, and he felt his pounding heart skip a beat.

"Er, sorry," he said, "I'm not sure what to say. I was hoping to get over here and meet you before anyone else, but maybe...I don't know...maybe I'm doing it all wrong. I'm not really into this bar scene. I saw you come in and you looked a little nervous. I thought if you let me sit here with you, you might eventually relax and enjoy your time. I can go away if you prefer."

"Ah, let me think about it," she said. Crash and burn.

"Ok, I'll just go back to where I came from," he said, and returned to his place at the bar.

He noticed the ring on her finger, but he didn't care. He had hoped she was here for the same reason he was, but wasn't surprised at his expected failure.

It didn't take long for another patron to walk over with a big smile and make his introductions. She smiled, he sat down, and he began to talk. Her smile disappeared. Her uneasiness, which had not gone far, returned. It was just a few moments later that she gradually stood up, picked up her purse and coat, looked around, and walked over to the bar next to her previous crash victim.

"I think I'll be better off talking to you," she said. Uh, oh. Now what.

"How about we pretend we are together to scare off the others," he said, hoping he didn't say the wrong thing. "Perhaps I could buy you a drink to make it more convincing?" he proposed. It didn't sound like a pick up line, did it?

She looked him in the eye with some nervous hesitancy. "Ah, I guess so," she said.

"What are you interested in? Beer, wine, ... water?"

"Ah, I guess wine - I don't know." She still seemed a bit overwhelmed.

"Well I think it depends on how you feel, and wine is probably a good choice for calming the nerves," he said. I don't really know anything about wine. Do you have a favorite?" he asked.

"I don't know. White, maybe?"

"Excuse me," he said to the bartender, "could you get her a glass of white wine, please? Thanks."

When she walked into the bar, she wasn't exactly sure WHAT to expect. She was frustrated with her marriage and didn't really know what to do about it. Yes, Frank was a good guy, but his interest in the bedroom seemed, well, non-existent. She wanted a little romance, a little excitement, a little, she didn't know, "something". She fantasized about a couple of things, but was afraid Frank would get upset, and she didn't like him to be upset. Frank was a guy who liked to hang out with the guys, sports, and beer. They had a good family and a good home, but that little extra something, that little bit of excitement...well, it just wasn't there. And she was tired of waiting for something to happen. So while Frank was busy with his buddies, and the kids were in bed, she left the house to go "shopping". She had left before, driving around, not exactly sure what to do. But this time, she decided to venture into a bar and see what happened. Maybe she'd walk in and find Magic Mike, who would take her into his big, strong arms, kiss her, rip off her clothes, and make passionate love to her on one of the tables. Hey, a girl can dream, can't she? Or maybe... she had other fantasies.

But the guy sitting next to her was not Magic Mike. He seemed like an older married guy, probably in his 50's or 60's - with his salt and pepper hair (heavy on the salt), it was tough to be sure. But he was nice for the moment. She wasn't sure if he was just a nice guy, or a pervert with good acting skills. But he seemed safer than the guy who sat down at her table without asking, and was clearly looking for something quick and superficial. She might be looking for something superficial herself, but coming from a guy like that, in the first 15 seconds, does not make a girl feel comfortable. She'd see if this nice guy, this guy who wasn't trying to pressure her with a bunch of questions, was, well, nice, but not too nice.

This guy...what is his name anyway?

"My name is Molly. What's yours?" she asked.

"I'm Jack," he said, extending his hand. She shook his hand, and he said, "pleased to meet you." Hmm, he might have some manners.

After a couple of awkward moments, Jack asked, "So what made you decide to come sit with me? That guy is much better looking than I ever will be...or ever was."

"Looks aren't everything," she said, with a half smile. Her smile. It changed her face. Her eyes had a little twinkle. And her smile began melting his heart.

Feigning shock, Jack said, "What? You prefer old, ugly guys like me over that?" he said with a scoff, pointing his thumb toward the unsuccessful suitor.

Molly smiled, then said, "well, maybe I'm looking for something different." That smile! OMG. He could feel it first in his bones. Then felt it elsewhere.

"Like what, if I may be nosy?" asked Jack with a softer voice. "What are you looking for?"

She paused, unsure if she was ready to tell anyone anything. "I don't know. I'm still figuring it out."

"Well, if you are looking for chocolate cake, I'm not sure if they have any here. But then, I haven't asked yet."

She smiled, and could feel herself relaxing. Jack couldn't resist returning his own smile.

"I don't know," she said. "I guess I'm just looking for someone to talk to."

"Well, it turns out, I've done lots of practicing when it comes to listening. Anything special on your mind?"

They talked for a while, relaxing, and getting more comfortable with each other.

"To be honest, I kinda wish I had a woman that was interested in me for more than a friendship. I feel like I've been stuck in the friend zone my whole life," Jack told her.

"Well, it can't be your WHOLE life," Molly responded. "You got married and had kids."

"In a way, I suppose. But I felt like I was performing a job. We were trying to get pregnant, so we went through the paces. I did my job, so that was that. Now my job is to bring home the bacon, mow the lawn, pay the bills, and a few other chores around the house. My reward is some great cooking and a faithful friend. But I was hoping for more female attention. And I don't mean my daughters telling me about their boyfriends, or when they are on their period. I mean some physical intimacy...with an adult"

"Your daughters tell you about their boyfriends, and their period?" Molly asked in surprise. "Teenage daughters don't normally tell their dad those kinds of stuff."

"Did I mention I'm stuck in the friend zone? Even with my kids," said Jack.

"So why don't you grab your wife by the hair, bend her over the kitchen table, and have your way with her," asked Molly, with a surprise that she dared say that to this almost perfect stranger.

"Because I'm not one who forces himself on someone who doesn't want him," said Jack. "I guess I've been indoctrinated with this sexual assault scare and 'Me Too' movement. I see it as respect for her. Besides, I don't see myself enjoying it if she's not. I like to give pleasure. I've tried to encourage her more than once to touch or let me touch. She makes fun of me, or complains about being tired, or she has a headache. It has been ten years now with nothing. I'm done trying. She won't even discuss it with me," said Jack, with the sound of frustrated defeat in his voice.

"I know what you mean," said Molly. "Frank doesn't look at me anymore. As long as I bring him his dinner and his beer, feed his friends, and clean up afterward, I have a purpose. I feel like I'm more the maid than any wife."

"So he doesn't grab you by the hair, bend you over the table, and have his way with you?" asked Jack.

"No," said Molly. "Never happened."

"So, if you have your wish, where else do you see yourself getting attention? Or what do you wish he'd do? Or does it have to be Frank?" He hoped he hid his ulterior motive.

She looked at him with surprise, not sure how she should respond to his boldness. But, they were just talking. "I'm not sure I should tell you," she said with a smirk. "I barely know you."

"That's OK. You'll probably go home later and we'll never see each other again. You can tell me. Who am I gonna tell?" said Jack.

After a moment, Molly asked, "Why don't you tell me what YOU would do? Or what do you want a woman to do to YOU?"

"Well, I'm afraid to tell you cuz you'll probably think I'm a pervert, and leave me, and it would ruin this great evening," said Jack.

"Ah, come on. You won't offend me, I promise. I dare you," she said with a gleam in her eye.

Jack hesitated, then began. "Well, it depends on what she likes. If she likes to be tied up, I have some ideas. If she likes the thrill of possibly being caught, I have other ideas. If she wants to be dominated, then I might have a couple more thoughts."

Molly was intrigued. Those sounded a lot like what she liked. "You like to be in charge, don't you?"

"Yeah, I guess so. What do you like?"

Molly didn't answer. Instead she said, "Give me an example."

"An example of what?"

"Of what you would do to her."`

"What do you mean?" Jack smiled.

Molly returned the smile and said, "If you were in charge, what would you make her do?"

"Like I said, it depends on what SHE is interested in."

Molly grunted.

Jack said, "OK, for example, let's say you were interested in submitting, I would tell you to go to the rest room, take off your panties, and bring them back to me."

Molly looked at him, paused, grabbed her purse, then got up and walked to the bath room.

Jack was in shock. He was also a bit excited. He couldn't believe it. What just happened?

A moment later, Molly returned and sat down and looked at him. After a pause, she opened her purse and showed him the contents. Jack looked inside and saw a pair of panties.

"That could be anyone's. Or your spare panties. Let me see if you are wearing anything."

Molly opened her mouth in surprise, but with a smile. "Here? Are you kidding? No way!"

Jack thought about it, then said, "OK, then. Go back to the rest room and put them back on. Then turn on the video camera on your phone and record yourself removing your clothes, maybe a little strip tease, then make sure the camera gets a good look at all of you, then get dressed, and come back here."

Molly hesitated. Jack said, "I dare you."

Molly couldn't resist. She got up again and headed back to the bathroom. She put on her panties, then set her phone on the sink, propping it up, and started recording. She slowly removed her dress and hung it on the bathroom door hook. The dress made her feel pretty and thought it might get the attention of some man. Now here she was taking it off for some man. Some stranger. He wasn't standing in front of her, exactly, which made it easier. She did a little dance as she removed her bra, unfastening it from the back, holding it close to her chest, then slowly revealing more and more of her breasts, then her nipples, then completely off, and on the hook on the door. Then a couple of slow rotations as she did a slow little dance before she reached into the waistband of her panties. She slowly lowered then as her hips swayed slowly back and forth. She was finally naked in some strange bathroom, It felt weird, but exciting. She pinched her nipples, partly for the camera, and partly for her own thrill. And thrilling it did feel. She rubbed a little between her legs, felt a little embarrassed, then quickly dressed. She grabbed the camera, checked herself in the mirror, and left through the door. She saw the smile on Jack's face. She was getting a man excited to see her.

When she sat down, Jack said, "let me see it."

"Noooo," said Molly and kept the camera in her hand at a distance from Jack.

"How do I know you did it?" asked Jack.

"Trust me,' said Molly.

"OK, let's try this. Just hold the phone in my direction, and use that bar at the bottom to quickly go through it. I won't be able to see anything, but it will show that you did something. What do you say?"

Molly thought about it and did what he said. She couldn't believe she did that, and was now showing this guy she just met.

"You're pretty cool," said Jack. "I'm impressed. Unfortunately, it is late and I need to get home. What are the chances I'll be able to see you again?"

"I'd like that. What do you have in mind?"

"Well, how about we meet here next Friday at 8pm.? We can pick up where we left off," said Jack. "Only next time, you tell me. I told you what I would do to a woman. Next time you tell what what you want a man to do to you."

Jack walked her to her car, gave her a kiss on the cheek, and wished her a good night before heading to his car. On the drive home, he wondered how many of his fantasies might actually come true.

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This story was written primarily with a shy, married, female audience in mind. I would be most interested in hearing your thoughts. This might be a boring story, by comparison. I was shooting for some realism - how did I do? Your feedback is welcome.