I’ll Bet You a Latte

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Double Penetration

“Chris, you’re forty four years old. You’ve been divorced for ten years. I think maybe it’s time to be a little less particular when it comes to the guys you’ll date.”

Chris shrugged bashfully, a trait her new friends Denise and Carol were getting used to after spending three months with Chris attending weekly classes on dating for divorcees.

“I’m not particular,” Chris argued. “I’m…um…careful.”

“Well, if you keep it up you’ll be carefully looking for somebody when you’re eight four,” Denise said. “Have you looked in the mirror lately? You’re pretty, blonde, thin, and have a great ass. Want to trade?”

Carol giggled, but Chris only blushed, saying, “I notice you didn’t mention my non-existent boobs.”

Denise replied, “If you had boobs I wouldn’t be talking to you. No guy would ever notice me standing next to you. It’s bad enough as it is being seen next to Meg Ryan’s twin.”

Chris looked at Carol as if pleading for help, but Carol had to agree with Denise. Chris’ lack of male friends was NOT due to her looks and time was running short. The three had formed an unofficial club whose sole purpose was to find mates for each other…as quickly as possible. The entire concept went against Chris’ conservative nature.

“So, are you going to answer the email from this Jeffrey guy?” Denise asked Chris.

“I don’t know. He’s six foot two, you know,” Chris said.

“Damn it, Chris. Quit making excuses. You’re five ten, for God’s sake. I’m pretty sure sex will work just fine between you two.”

Chris frowned. “Why does everything come down to sex with you, Denise?”

“Alright, you have a choice,” Denise said with obvious irritation. “Either start dating Jeff…or any other guy…or wake up to find you are fifty, still single, and not the least bit horny.”

“Will you consider the first date a total failure if we don’t fuck all night?” Chris asked her.

Denise and Carol both had to suppress their laughter. If there was one thing Chris did really, really poorly, it was feign anger.

“I’d be happy if you told me you felt his hard-on one time when you kissed,” Denise admitted. “God knows we don’t want to rush you into anything.”

“Have you learned anything new about him?” Carol said, trying to act as peacemaker.

Chris grinned her normal timid grin. “Oh, just that he’s some type of vice president at his company and does something with computer networks. He likes sports, which, of course, I know nothing about. And his two kids are twelve and thirteen.”

“How certain are you that he’s divorced?” Denise said.

“Ninety five percent,” Chris replied. “A friend of mine in that county is checking the public records for me.”

“Yea!” Carol exclaimed. “You actually took the initiative on something. Next thing you know you’ll have your hands all over him.”

“Oh, stop it! You guys are awful,” Chris said amid their laughter.

The fact was, Jeff was indeed very divorced and very keen on meeting the woman behind the picture of Chris that Denise and Carol had sent him. Denise had only met him once, at a party, but was willing to hand him over to her friend Chris in keeping with the trio’s unsanctioned pact. He was actually quite good looking and athletic, and probably three or four years younger than Chris. But then, Chris didn’t look like she was forty four, so it might still work, Denise argued.

But any man who was serious about Chris would have to quickly learn to deal with her over-the-top conservatism. There was only one man on earth who knew how Chris could be transformed behind a closed bedroom door, and that man had thrown her away for a younger lover. Chris had hardened in the ten years since the dumping, but a flame still burned for the right man. Secretly, she was very interested in Denise’s tall friend. She just wouldn’t let Denise and Carol know it until the time was right.

Chris did in fact answer Jeff’s email and the two exchanged several messages over the next few days. As the second weekend of their ‘friendship’ approached, Jeff finally broached the subject of their meeting in person. Chris resigned herself to the inevitable and agreed to have dinner with him halfway between their two homes, which were about one hour apart.

She figured this safely allowed for a harmless getaway if the evening didn’t go well. And despite her best intentions, she didn’t expect the evening to go well. So little in her life had, why would this be any different?

Chris’ first clue that the date would be anything but what she expected came when Jeff appeared in the restaurant lobby. He took her breath away with his tall, stately manner and incredible smile when he recognized her. His business casual outfit underscored his unique position in life: not far removed from youth and not quite middle-aged. He was mature with a hint of youthful liveliness.

The introductions were short and nervous, as expected. But five minutes after being seated most of the tension had evolved into true interest in learning more about the other. Chris studied xvideos porno Jeff’s features while listening to him speak and Jeff inspected every inch of Chris’ body visible above the table. Her hair was a perfect combination of blonde tousle and carefully controlled curl. Her eyes were like blue gems. If only the opening in her blouse had displayed even a hint of cleavage, she would have been a goddess.

But he put aside this ostensible imperfection for the moment and set his goal on making her laugh at least once during the meal. The objective was met over and over again until it would have been difficult to ascertain which of the two was more surprised at how well the dinner went.

They walked out of the restaurant nearly two hours later fighting the urge to hold hands. They just weren’t that comfortable yet. But when they got to their cars and Jeff touched Chris on the arm, she felt her pulse quicken.

“Can I text you?” Jeff asked.

“You better. But not while you’re driving.”

He smiled. “It can wait that long. And if I ask if I can see you again…?”

Chris flashed her normal reserved grin. “Try it and find out.”

Jeff slid his hand down her arm until their hands came together. “OK. I will. Good night, Chris.”

“Good night, Jeff. Thanks for everything.”

The next day, at their favorite Starbucks, Denise summed up her and Carol’s joint reaction to Chris’ account of the date: “And that’s it? You just said ‘Thanks’ and drove off in separate directions?”

“Yep,” Chris said with pride. “It was a really nice dinner.”

“But what about dessert?” Carol inquired.

“No dessert last night,” Chris replied. “But he texted me right away and, well, I think I’ll see him again soon.”

“When?” Denise said impatiently.

“Oh, maybe this weekend.”

Denise and Carol exchanged a high-five. “Now we’re getting somewhere. Where are you going to meet?”

Chris said, “My place.”

“Yes!” Carol said with restrained glee. “We expect videos of the whole thing.”

“And you won’t get them,” Chris said. “He actually strikes me as a gentleman, not the type of guy you seem to want me to meet. In fact, I’ll make this offer.”

Denise and Carol looked at her with renewed interest.

“I’ll pay for all the lattes the next time if Jeff and I have sex on Saturday.”

Denise scowled. “Damn. Now you have incentive NOT to fuck him. And by the way: it doesn’t have to be intercourse. ANY sex counts.”

The three friends agreed to the arrangement, each of them quickly forming their own opinion as to the outcome.

Saturday’s ‘date’ was set up as nothing more than an opportunity for Chris and Jeff to continue their conversation and spend another few hours together. Chris was allowed to choose the destination if they went out, but she made it clear she wanted to grill some food for them back at her place. Jeff eagerly accepted.

Chris paced the great room of her condo in the minutes before Jeff arrived, deciding twice not to change into another outfit. She would go with her jeans and t-shirt, hoping Jeff followed her orders to make it very casual.

Her fears were unfounded. Upon the knock on the door, she opened it to find him equally informal.

“Hey. Come on in,” she said with a smile. “Any problems finding it?”

“Just one wrong turn,” he admitted. “That’s not bad for me.”

He scanned the immaculate, bright condo while Chris led them to a nearby couch. She offered a drink, he ordered a Coke, and they talked as she prepared snacks in the adjoining kitchen. When she returned, Chris sat on the couch next to Jeff, but at a relaxed distance. The conversation came much easier than either of them had expected and soon even their body language showed the comfort level.

More than half an hour passed before Chris felt the need to ask if Jeff wanted to go anywhere in particular.

“You know far more about this area than I do,” he said. “I’ll leave it up to you.”

“Well, I did have something in mind, but you have to promise you’ll tell me if it sounds dreadful to you.”

Jeff laughed. “What is it?”

“There’s a new bookstore that just opened that specializes in old and rare books,” Chris said, looking over at him with guarded optimism. “Do you mind if we go check it out?”

It certainly wasn’t what Jeff would have guessed, but he wasn’t about to decline. “Let’s go,” he answered quickly.

Chris drove, as she knew the way. The short trip was filled by Chris divulging her wish to explore the bookstore’s collection of mysteries.

“Any author in particular?” Jeff asked, hoping he wasn’t expected to add greatly to the discussion.

“Anybody from the golden age of British detective mysteries,” she said with apparent excitement.

Jeff glanced over at her. “When, exactly, was that and who were the authors?”

“Primarily between World War One and Two. The most famous authors, of course, were Agatha Christie and Dorothy Sayers, and others. But I’m hoping they have some originals yerli porno by people like J. S. Fletcher and E. C. Bentley.”

Jeff made an acknowledging sound that caused Chris to look over at him and giggle. “You could care less. Right?”

He began to claim total curiosity, but had to confess otherwise the more Chris smiled. “I’ll be in sports,” he finally stated, which allowed Chris to laugh.

They walked into the surprisingly large bookstore together and spent the first ten minutes or so just browsing. Finally, Chris found the mystery section in a secluded corner and they separated. Her attention was equally split between the unique collection of books and her view of Jeff. She was able to clandestinely watch him from afar. The result was a new opinion of him: Jeff was actually very striking. With each gaze, she found him more attractive.

Chris nearly missed entirely what appeared to be a first issue of Sayers’ ‘The Nine Tailors’, but she managed to pull it off the rack amid battling emotions raging inside her body—the thrill of the find and her newfound lust for Jeff. Several times she caught him looking across the store at her, wondering if he felt the same.

Soon, he had meandered his way around and they met in her quiet corner.

“Any luck?” he asked.

Chris held up her prize. “I’m so excited. And the price is fantastic. I still can’t believe it.”

Jeff put his arm around her and expressed his happiness for her, but nothing he said could have matched what Chris felt from his mere touch. She was practically shaking by the time he let go. They had come close to kissing in that instant, and Jeff sensed it.

In all the time they had been in the store, Jeff had only seen one other customer and the person behind the counter. Now he and Chris stood just a couple feet away from a short hallway leading back to either offices or storage space. He took Chris by the arm and moved her into the hallway, much to her bewilderment.

“What are you…,” she began to say.

Her sentence was cut short when Jeff leaned against her and placed his mouth on hers in a forceful kiss. Chris let the wall hold her up while the kiss grew more passionate. She wanted to put her arms around him but the book prevented it. Instead, their bodies came together from the mere intensity of the kiss.

She could feel him. She wanted to touch him.

But he pulled back and Chris sighed, “Whoa. I didn’t expect you to be THAT happy I found an original Sayers.”

Jeff smiled and said, “I’m happy if you’re happy.”

“We better go,” Chris said, not sure she could trust herself any more.

The ride home was quieter than the one to the store and the apprehension between the two could be felt. Neither knew how the other would react. Neither knew that each of them were disappointed it had to end.

Once back inside Chris’ condo, she was quick to start a task that kept her off the couch for a while.

“Are you ready to eat?” she asked him.

“Whenever you are.”

“Let me get it ready,” she said.

“What can I do?” he asked.

“Start the grill, please.”

That bought her enough time to settle her nerves, take a few deep breaths, and convince herself nothing had to happen right away. She moved from the refrigerator to the sink to the cupboards in a faster than normal pace until she heard Jeff coming back in from the porch.

“Done,” he announced.

“Great. Thanks.”

Then Chris sensed him directly behind her as she stood by the counter. She looked over her shoulder. He moved closer.

“You aren’t mad about the bookstore?” he said.

“Of course not,” she replied with a forced smile.

“I watched you go through the books and could tell you were enjoying yourself. You looked pretty, even from across the room.”

She barely had an embarrassed ‘Thanks’ out of her mouth when his arms wrapped around her waist. She put down the food she was holding.

“Can I ask for one more kiss, in private?” he said.

But his lips were already on her neck and seeking out her ear behind the thick, blonde hair. Chris answered by turning her head just enough for their lips to meet. He didn’t force her to turn. She volunteered by twisting around and allowing him to kiss her a little harder.

It didn’t take long for Chris’ hands to be going through Jeff’s thick hair and his hands to be sliding up and down the back of her t-shirt in the middle of an ever-increasingly zealous kiss. She was leaning back against the edge of the counter until Jeff’s hands sought out her ass and she eagerly let him find it.

He pulled her even closer and Chris moaned her approval.

“You’re making it hard to cook,” Chris said during one brief lull in the kiss.

“You’re making it hard,” Jeff said.

His mouth muted Chris’ giggle but she could feel the evidence between his legs. Unsure of just how far he wanted to take it, she let a hand travel down to his leg, and then onto the front of his jeans. Jeff moved back the couple of inches it took youjizz porno for Chris to put her hand between their bodies and search out the bulge under his zipper.

“I guess the burgers can wait,” she managed to say.

Jeff didn’t reply. His hands were moving across the front of her shirt, tentatively contacting the outer edges of her bra-covered tits. He, also, was unsure of her intentions. But when she tightened her grip on his erection the more he touched her, he became emboldened.

Jeff lifted Chris’ t-shirt enough to find the soft flesh of her stomach and waist. He let his fingers drop inside the waistline of her jeans and she gave no hint of rejecting him. He looked into her eyes and flicked over the button to the jeans. She looked back with renewed lust and he very slowly lowered the zipper.

The moment his hand touched the front of her panties Chris muttered a barely audible ‘Yes.’ She rubbed his cock harder. Jeff pushed his hand lower and found the already damp spot surrounding her pussy. He pressed with more force and Chris slightly backed away. But when Jeff began massaging the spot, she came back to him and even arched her back to meet his fingers.

“Tell me if you don’t want to…”

“Don’t stop. Please,” she interrupted him.

Jeff shifted his hand so that it was inside her panties, seeking out the swollen clit he knew was there. He used her own juices to wet his fingers and began a soft rubbing.

“Oh God, Jeff. That feels so good.”

Chris had lessened her assault on his cock and Jeff was fine with that…for now. He always enjoyed giving almost as much as receiving and he especially enjoyed finding out for the first time what excited a woman. Chris’ near constant moaning assured him he was on the right track.

The tightness of her jeans made it difficult for Jeff to get real creative. Chris must have sensed that because she was soon pushing her jeans down so that her panties was the only thing covering his hand. Jeff kissed her as a reward and got up the courage to slide a finger down to the opening of her pussy.

“Wait,” Chris said quietly, and Jeff was afraid he went too far. Instead, with his hand still in place, she kicked off the jeans and pushed them aside with her foot. She spread her legs and Jeff had free access to her pussy.

His finger was quickly inserted and Chris sighed loudly. Her hand once again clutched at his cock, which was now straining mightily against his pants. Jeff finger fucked her for only a moment before returning to her clit. He stayed there while listening to her breathing grow more uneven.

Then he was kneeling in front of her, pulling down her panties to reveal the wet, throbbing pussy. Jeff removed the panties from around her ankles and moved his face into place between her legs. Chris spread them even farther and put her hand gently on the back of his head.

Jeff kissed all around it before finally letting his lips touch the skin protecting her hole. With long swipes of his tongue, he worked his way up to her clit. The first time he touched it Chris let out a little cry of delight. When he put his mouth entirely around it and began to suck it in earnest, Chris said, “Yessss, Jeff. Oh my God, yes!”

If this was how she was going to lose her bet, she could live with it.

His mouth and tongue were everywhere. He drove his tongue inside her pussy for long periods and licked her clit until Chris thought it would burst. He pulled on it with his lips. He rubbed it with a finger while going back to probe her pussy with his tongue, and then swapped places with his hand and mouth.

Chris knew there was no holding back her orgasm and Jeff was intent on making her cum. She got as comfortable as possible against the counter and warned him, “Jeff! I’m almost there. Of fuck. I’m…gonna…cum.”

He never slowed down. One last series of licks and Chris started her orgasm. She pulled his head closer and drove her pussy into his face with a series of thrusts. Each thrust was accompanied by a forceful groan. Jeff felt her entire body quiver for over a minute of what must have been multiple climaxes.

He licked up the juices as they collected around her pussy, tasting her sweetness and spreading it back up to her clit. Each new contact with that erect nub caused her to shriek and shudder once more.

Finally, she begged him to stop.

“Get up here,” she ordered, pulling up on his face.

They kissed and she tasted her own body on his lips and tongue. When they finished, he said, “Can we eat now?”

Chris laughed. “I thought you just did.”

Then her hand was on him again. “What about this?” she asked with a grin.

“Next time,” he told her and continued the kiss.


“Thanks for buying, Chris,” Carol said a few nights later at Starbucks.

“Yeah. Now give us the details. Don’t leave anything out,” Denise said.

Chris blushed. “There’s not much to tell.”

“The hell there isn’t. Now out with it,” Carol demanded.

The locale did not allow for a full recounting of the event and, in the end, Denise and Carol were convinced Chris was holding out on them. They didn’t believe that ‘hors d’oeuvres in the kitchen’ fully detailed what took place, but they didn’t press her too hard considering a nearby table was occupied.

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