The Bet She Happily Lost

Jules Sinclair is an extraordinary woman. She possesses striking natural beauty, looking decades younger than her actual age. She is smart, bold, and complex. She teaches guitar and is married to an accountant. They have a grown son who lives and works in France.

Jules has always enjoyed sex and has never felt any obligation to be conventional about it. There are many fascinating stories that could be told about her. Some of them appear elsewhere in Literotica. This particular tale chronicles one of the many sexual adventures in her life.

During the time period relevant to this story, Jules was in a relationship with an unmarried medical technician named Daniel. They met when he started taking guitar lessons from her. They connected right from the beginning and one thing, as they say, led to another. When she is in the right mood, she stops by his apartment for some steamy sex.

Although Jules enjoys the occasional physical intimacy with Daniel, she thinks of him as just a casual friend. However, Daniel adores and idolizes Jules, as have many other men. He is constantly telling her how sexy and attractive she is.

One occasion when Jules's husband was traveling out-of-town, Jules and Daniel were able to share two whole days together. During the afternoon of the first day, they were lying in bed enjoying a post-sex afterglow when Daniel once again started talking about her beauty and ability to attract men.

To prove his point, he offered to bet her a dollar that if she took a seat by herself at the bar of the Rowdy Room (a popular neighborhood tavern), that some guy would hit on her within five minutes.

Jules was amused and intrigued by his proposed wager. She said, "OK, Danny, I'll take that bet."

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~``

So on the evening of their second day together, Jules and Daniel entered the Rowdy Room. Jules was wearing a knee length skirt and a T-shirt advertising Gretsch guitars. As usual, she wore no makeup. But even without trying, she looked gorgeous.

They sat down on stools at opposite ends of the bar and pretended they didn't know each other. The bet was on.

But after only 30 seconds of sitting down, it was over. A good-looking fellow who appeared to be in his twenties stopped at Jules's barstool seat and started talking with her. From where he was sitting, Daniel couldn't hear the conversation. But he could see that the fellow had sat down on the barstool next to Jules's and that they were smiling and chatting amicably.

Jules immediately understood that Daniel had won their little bet. She unmistakably had been 'hit on.' But she was enjoying herself, and decided she was not yet ready to bring the evening to a close. In addition to being good looking, the fellow who had approached her had a warm smile and a friendly demeanor. Jules thought to herself, "Let's just take a little time and see where this might go."

The handsome stranger had introduced himself as 'Elliot'. As they exchanged introductory questions and small talk, Jules fabricated some of her answers in order to stay anonymous. She assumed he was doing the same thing. But they had made a connection, and their conversation grew increasingly flirtatious.

Daniel watched as the scene at the other end of the bar unfolded. He had won the bet and was expecting Jules to excuse herself from any further interaction with this fellow. But he could see from her body language that she seemed to be fully enjoying the young man's attention.

After about a half hour of playful conversation, Elliot leaned close to Jules and said, "It's so noisy and stuffy in here... could I interest you in a little walk in the night air?"

Jules liked the idea. The bar was loud and distracting, and she was enjoying being with her new friend. Her natural boldness also pushed her forward. She didn't think that Elliot seemed in any way dangerous. In any event, she felt she could handle any situation if he got too aggressive.

She replied, "A walk sounds nice! Let me hit the powder room for a minute and I'll be right back. "

Daniel watched as Jules got off her barstool and walked toward his end of the bar. As she approached where Daniel was seated, he expected her to stop and rejoin him. But she walked right past him without even a glance in his direction. He watched as she entered the ladies' room.

A few seconds later, Daniel's phone buzzed with a text message from Jules:

"His name is Elliot. He and I are going out for a walk and to get some fresh air."

Daniel was at first taken aback at this terse note. He wondered what "Elliot" might have in mind and, for that matter, what Jules might be thinking.

He texted back, "I may try to keep an eye on you from a distance. But I promise not to interrupt or interfere with your little liaison unless I see or hear trouble. Please be mindful of your safety."

Jules responded: "You're such a worrier! I know how to fight back, or I can scream and run if I need to. But I really don't foresee anything like that happening. He seems like a genuinely sweet guy."

A minute later, Jules came out of the restroom and headed back to the waiting Elliot, who was smiling broadly. The two of them walked out onto the tavern's parking lot. At that particular moment, the lot was noiseless, except for the low hum of traffic speeding along a nearby highway. The lot was poorly lit, and the darkness added to a feeling of privacy as they strolled and conversed.

Meanwhile, Daniel followed them as they exited the tavern. He maintained a wide separation from them. The darkness helped him to stay well hidden. He watched them as they slowly strolled through the quiet lot.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Jules was enjoying the walking and talking in the darkness. The cool night air felt refreshing and Elliot proved to be funny, smart, and a good listener.

Their walk was suddenly interrupted by a soft electronic sound. Elliot grabbed his phone from his hip pocket. "Oh darn!" he said. "My phone is telling me it's almost completely discharged. Do you mind walking over to where my car is parked so I can hook up to a charger? My car is just a few rows over from where we are right now."

Jules replied, "Of course, that's fine." And in a humorous authoritative voice she added, "We must obey the commands of our overlord phones!" They both laughed.

In less than a minute they stopped beside his Honda CRV. He connected his phone to the car's charger, and closed the car door.

As he turned around, he found himself face-to-face with Jules. He looked into her beautiful green eyes. They smiled at each other and Elliot said, "I just have to ask this -- would you be offended or stop me if I tried to give you a kiss? I mean... you're so beautiful and you seem like someone who would be a fantastic kisser. The truth is, I've been wanting to kiss you ever since we met."

Jules looked thoughtful for a moment. She smiled and replied, "Hmmmm... I don't know what would happen if you did that... why don't you try to kiss me and we'll see?"

They slowly brought their mouths closer and closer together until their lips met. They held the kiss for a while, both savoring the moment. After that first kiss, they just kept going. Their kisses were gentle at first, but deepened in intensity as they continued.

Jules whispered in his ear, "Well, I guess we found out -- I won't be offended or try to stop you from kissing me." Their kissing became even more passionate.

A few car rows away, Daniel had found a place where he could crouch down and remain hidden. His view of the couple was not complete. But as his eyes adjusted to the dark, he could detect some of what was going on. He could see they had started kissing each other. As he watched, he was feeling increasingly jealous and also increasingly turned on.

Jules has always been open to various kinds of sexual pleasure. And in her experience, the intensity of sex is amplified when it is forbidden. Although he had just met her, Elliot sensed these characteristics in Jules. The passion of her kisses also suggested her openness to greater intimacy. He decided to act daringly, judging that his new friend would be receptive to his advances.

Moving deliberatively, Elliot slowly lifted her T-shirt up. When she offered no resistance he continued, and pulled it off over her head. As he had noticed earlier, she was braless.

Elliot started gently massaging her beautifully shaped breasts. He was especially turned on by her nipples, which were protruding and firm. They tilted slightly up, inviting his touch and attentiveness. He bent over so he could kiss, lick, and suck on her fearlessly displayed breasts.

Jules basked in her own lack of inhibition. "Here I am," she thought, "Topless in a bar parking lot, making out with a young stranger." This thought made her sexual juices begin to flow.

She whispered, "Bite my nipples... not real hard... but firmly." Elliot happily complied with this erotic request, and Jules's knees weakened as she enjoyed the mixture of pleasure and gentle pain.

It was apparent to both of them that if this parking lot intimacy was going any further, they would need more room. Elliot said, "Give me just a minute." He walked to the back of his car and raised the hatchback, opening up the cargo area.

He said, "How about hopping up here and dangling your lovely legs out of the back of the car?" Jules kissed him hard, smiled, and complied with his request.

After she was situated as he suggested, Daniel grabbed hold of the tops of her skirt and panties with both hands. Jules could see immediately where this was going. So she lifted and arched her hips up off the floor of the cargo area, allowing Elliot to smoothly pull her skirt and panties down and off.

Except for the flip-flops that graced her lovely feet, Jules was naked, her beautiful body on full display for him.

She closed her eyes and embraced the excitement of the moment, spreading her luxuriously long, shapely legs for him. The scent of her pussy pervaded the night air. Jules murmured, "Go down on me and make me cum."

A quiver went through Elliot's body as he heard these words. He'd never heard a woman be so direct about her sexual desires. He got to his knees and leaned forward. Jules scooted toward him, spreading her legs even wider, making it easier for him to reach her pussy with his mouth.

He started kissing all around her upper thighs and her soft, tan-colored pubic hair. He could not help but notice that her clitoris was large enough to visibly hang down slightly between her legs. "What a beautiful turn-on!" he thought. His kisses kept getting closer to her vagina.

After several minutes of kissing and licking all around her vaginal area, Elliot finally put his tongue on her clitoris. He licked up and down the moist, swollen labia lips of her glorious pussy.

He thrusted his tongue into her hungry vagina. As he tongue-fucked her, she became more and more turned on. She again arched her hips off the floorboard of the cargo space, this time to allow his tongue to get even deeper inside her.

As he was licking and penetrating her pussy with his tongue, he felt the muscles of her pussy contract. Jules was beginning to cum. The forbidden and public nature of their encounter had enhanced her excitement and expedited an orgasm.

As she came, she moaned loudly. So loudly that even Daniel, perched a couple of car rows away, could hear her. He knew what that sound meant, and his jealousy and arousal spiked even higher.

Jules wasted no time in keeping the sexual energy high. "Make me cum again," she said with some degree of urgency. Elliot was very willing to comply, and kept up with the intense oral stroking and penetration as Jules continued to respond.

He was intrigued and drawn to the prominence and beauty of her clitoris. He discovered that he could draw her swollen labia into his mouth and suck on it. Jules responded excitedly to his stimulation. As Elliot sucked on her clitoris, he also began fingered her, plunging two fingers deep into her wet vagina. Jules responded even more enthusiastically, her body slightly twisting left and right.

It wasn't long before Daniel heard another of Jules's moans of ecstasy. She had cum again. He mentally pictured what was going on just a few rows of cars away and his heart raced.

After she came in his mouth the second time, Elliot got up beside her in the cargo area. He pulled her naked body close, hugging and kissing her passionately. Jules could taste her own cum on his tongue and a tingle went through her body.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Each passing minute increased the likelihood of the two adventurous pleasure seekers being discovered by a passer-by. However, while not a "scorekeeper", Jules has always tried to be fair-minded about both partners in intimacy receiving similar degrees of sexual gratification.

It seemed to Jules that a backseat blowjob was in order, and she was eager to see, feel, stroke and ultimately suck Elliot's young cock.

Jules has always enjoyed giving men oral sex. When guys come in her mouth, her nipples always stiffen in response. She delights in experiencing the sensation of a man losing control of his body and mind at the moment he cums.

Jules quickly got dressed and Elliot closed the hatchback on his car. She remained in control of the situation, stating, "Meet me in the backseat." They both slid into the backseat of the vehicle and started aggressively kissing each other again. Elliot wasn't sure what was going to happen, but he knew what he was wishing for. And his wish was about to be granted.

Jules wasted no time, and immediately started groping him on the outside of his pants as they kissed. She could feel he was getting aroused. She told him, "Pull your trousers and underpants all the way down so I can play with your cock."

Elliot gulped, again surprised at her directness. She watched him swiftly unbuckle his belt, undo his trouser button, unzip his fly, lift his hips off the seat, and push his pants and underpants down to his ankles.

Jules enjoyed watching him undress. His naked manhood stood at rock hard attention. At first, she just ran her right index finger up and down the underside of his erection, barely making contact. She kept teasing him like that for a while, then started stroking the shaft with her whole hand, but again just lightly. A small amount of pre-cum oozed out of his throbbing member.

She felt his balls, then continued slowly stroking him from the base of his shaft to the head. Now it was Elliot who could be heard moaning. Jules scooted into a position where she could take him into her mouth.

She leaned over toward him, and began licking the head of his erection with her tongue. Then she kissed and licked up and down the shaft. Elliot gently pushed her head down, physically urging her to take his cock fully into her mouth. But Jules resisted and whispered to him, "Not yet."

As she continued to pleasure him, a few cars were driving through the parking lot. The lovers could also softly hear the voices of people entering and exiting the bar. Jules decided it was time to bring things to a climax. She took his cock fully into her mouth and brought her lips and mouth rapidly up and down, up and down, while her tongue swirled around the head of his swollen cock.

Jules could feel him tense up as he prepared to cum. With a loud groan, he exploded into her mouth. He had a significant load for her to take. But Jules took it all in and swallowed it in three gulps. As Elliot panted and gasped for air, Jules licked his cock clean, too.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

When he got his breath back, he stuttered, "That was the best... the best... the best..." Jules interrupted him, saying, "I think the word you are looking for is 'blowjob'."

Elliot smiled and replied, "I didn't want to sound crude after such a beautiful experience." She said, "It's okay. I appreciate your attempt to find a more elegant word!" They both laughed.

Jules continued, "I hate to break up the party, but this parking lot seems to be getting more active. And in any event, I have plans to meet a friend and I need to text him. So I'm afraid this is going to have to be a 'kiss and run' experience."

Elliot pulled up his pants and underpants, but not before Jules gave the head of his cock a final kiss and lick. They got out of the car and hugged. Elliot said, "Should I wait with you until your friend shows up?" Jules replied, "No, go on back to the tavern and enjoy the rest of your evening. You can brag to all your friends about your great conquest tonight!"

Elliot laughed, "Well, I think I will cherish this get-together as our secret. It was special and I genuinely enjoyed it on many levels, and not just sexually."

Jules said, "I feel the same way." They kissed and hugged one more time.

Elliot pulled out his wallet and extracted a business card from it. He handed the card to Jules, saying, "Here are my cell numbers at work and home. Feel free to discretely reach out if you are ever in the mood."

Jules glanced at the card for a moment, noting that he was a portfolio manager for an investment firm, just as he had said when they first met in the bar. She tucked the card into her hip pocket and said, "I might surprise you with a call one of these days. I think we have some unfinished business." He replied, "Go ahead, please surprise me." They both smiled.

Elliot waved good bye as he turned and walked away, disappearing into the entrance to the bar.

Jules got out her phone and texted Daniel, "I'm in the parking lot and ready to leave. Come find me. I will be on the lookout for you."

He texted back, "Turn around... I'm right behind you."

She turned and saw him walking up behind her, smiling. They laughed and hugged each other. She said, "Have you been out here hiding in the parking lot this whole time?"

He replied, "Yes, and I was cramped and suffering while you were having the time of your life with this Elliot guy."

Jules laughed. "Why Danny, you poor boy, I believe you are jealous."

Daniel chuckled in spite of himself. "I admit I am. It's exciting for me when you tell me about some of your bad girl experiences, or even if I just think about you being naughty with other guys. I am jealous and turned on! So let's please get to my apartment as soon as possible. And hopefully, you'll find my bed a little more comfortable than the back seat of his car."

Jules felt energized from her experience with Elliot, and it had been a while since she engaged in sex with two different men on the same night. She proclaimed, "Okay, big boy. Take me to your boudoir so I can be a naughty girl with you, too!"

She softened her voice and added, "And I'll describe every sexy detail of my time with Elliot for you..." Daniel squeezed her hand in anticipation and heaved a sigh. "Oh Jules, you amaze and thrill me. I can't wait!"

When they got to his car, she reached into her purse and pulled out a dollar bill. Handing it to Daniel, she said, "And here's the dollar I owe you... this turned out to be a bet that I happily lost!"

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~