Frank and Cheryl Ch. 03: Something New

Story Info
Frank & Cheryl enjoy a new experience and make plans.
7k words
4.64
8.8k
8

Part 4 of the 7 part series

Updated 06/09/2023
Created 02/12/2019
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Author's note: If you haven't read "Frank & Cheryl 01" as well as "Frank & Cheryl 02" you might want to, just to know the background on this couple and how they arrived at this point in their building relationship.

Physical descriptions: Frank is a divorced 35 year old, 5'-11" tall, 185 pounds and fit; brown crew cut hair, clean shaven, brown eyes. Cheryl is a never married 32 year old, 5'-01" tall, 110 pounds and very small framed. A-cup close-to-but-not-quite- B-cup chest with highly sensitive nipples. Dirty blond hair that she keeps cut short. They are both into fitness, so Cheryl's body, while petite, is curved and firm.

*****

Cheryl was beyond delighted. At 32 years of age she had started to believe that she wouldn't find the right guy to spend her life with and she clearly remembered when she'd first met Frank some ten years earlier. He had been married then and hadn't really caught her attention. He had been polite enough and was good looking enough but the fact that he was married had pretty much closed her mind to any further thoughts. All these years later when she ran into him at the grocery store she felt like he had improved in looks, was definitely in better shape... and no longer married. When he had suggested dinner it secretly delighted her and the way things had progressed since then weren't disappointing in any way.

Some weeks back, as she thought across her memories of their time dating so far, she had confessed her past to him and he had taken it in stride as if it was perfectly common for her to have spent a year as a prostitute. In the weeks since then it had become abundantly clear that he was being completely honest and couldn't have cared less that she'd once been a paid escort. He'd proven himself competent and open in bed; creative and energetic... Yes, she was quite delighted at how things were going. There were experiences that they had yet to explore but she felt it was more because neither of them was unnecessarily pushing the particular activities rather than either of them being opposed to... well... any sexual activities. She remembered some particularly hot moments for her including their first play time together when he'd sunk his thumb into her backdoor while taking her doggy style. Since then, their sexual activities had touched on anal stimulation, as much for him as for her, but neither of them had pushed the issue of anal sex. She knew he'd get there; every man did eventually, and if he took his time about it, she knew she'd love to give that to him. She enjoyed it and looked forward to experiencing his response that first time she either let him take or asked him to take her backdoor.

As she prepared herself for the evening with him - dinner followed by their inevitable hours long sexual romp wherever it occurred - her only concern was their pending test of outlook. They had agreed, some weeks back, that they both wanted emotional monogamy but were enthusiastic about physical non-monogamy. They continued to agree about it any time the topic came up, but they'd yet to figure out how to test the outlook. Her thoughts were interrupted at the sound of her doorbell. She smiled at her reflection in the mirror, giving one last touch to her hair before going to answer it. She knew it was Frank and it was hard to contain her excitement. No man had ever made her this happy and done so with such ease... and she had an idea of how to test their voiced outlook about an openly physical relationship. She was interested to see and hear his response to her suggestion.

When she opened the door she found him looking as good as he usually did, dressed in his usual slacks and oxford, but seemingly never the same ones or combination. This evening was a pair of dark blue slacks under a black oxford with his matching black belt and black shoes. He had obviously shaved just before coming over to pick her up and he made it a point to wear her favorite cologne: Obsession. She was a naturally sexual and physically focused person, but smelling Obsession on him literally made her pussy wet and her mouth water. She didn't know what it was about that particular aroma, but the cologne mixed with his personal chemistry affected her strongly.

The look on his face said he was equally happy with her appearance. She typically wore a very sheer bra - her breasts were big enough to benefit from the bra and not need padding to look appropriate to her size - with a matching color thong (if she wore panties at all). The usually sex undergarments were covered by a dress that fit snuggly and exposed plenty of skin while suitably covering her to about mid-thigh.

It seemed to be becoming a habit as they took a moment to look at each other, taking in the sights and enjoying it. Neither of them was offended that the other sometimes looked at them purely to appreciate their physicality; in fact, they both took the compliment. Both worked hard to maintain their fitness levels and both had attractive bodies. They took it as a compliment when someone else - of the opposite sex or not - looked at them with an obvious appreciation for the discipline and investment in their fitness. When it was just the two of them, they enjoyed seeing the looks of appreciation because they knew that the look wasn't just in reaction to the appearance but also due to the recent memories of how they'd enjoyed sharing their bodies and the pleasures they'd given to or taken from each other.

The moment was broken when their eyes met and Frank asked, "Ready?"

"Yep!" Cheryl answered enthusiastically. She had already grabbed her small purse and stepped out, turning to lock her apartment door and then taking his hand as they headed down the stairs. During the brief time it took them to get down the flight of stairs and over to where he'd parked his car, Frank thought about the fact that Cheryl seemed perpetually happy. He knew she liked her work and was good at it. He knew she was healthy and generally happy with her current circumstances in life. He silently hoped that he was helping to raise that enthusiastic happiness she seemed to enjoy almost every time they spent time together.

He held the car door open for her as she got in and got a quick flash of her sexy thighs as she sat and turned into the car. Once they were both in and buckled Frank pulled out of the parking lot, turning toward the destination he had planned. Cheryl had no clue where they were going. She had made it clear on their very first dinner date that she left the planning to him. He had taken that in stride and planned every date since. Sometimes the "date" was simply an evening at his or her place for hours of sexual play but that was the rarity amongst the dinner, movie, picnic, shopping, etc. dates. Frank had planned a relatively unique evening for this date and he wondered how Cheryl would react to part of his plan. Based on his experiences and conversations with her so far, he didn't think she'd balk even the least bit and she'd probably have a lot of fun.

Their conversation was about work and relatively mundane topics as Frank drove, Cheryl just along for the ride and eager to see where he took them. They both lived about a half hour outside of the nearest "big city," and had avoided going into it for their dates so far. This evening Frank drove them straight in and toward the northwest quadrant. He knew right where he was going and found parking without any trouble. Cheryl didn't remark on the area or any possible destination and Frank liked the fact that she just took in stride whatever he planned, apparently sure she'd have a good time no matter what it was.

Frank had learned early on that Cheryl enjoyed a good piece of meat... and by that they meant beef steak... and he had made reservations for them at one of the higher-end steak houses in the city. Cheryl voiced her delight with his choice as they were seated and ordered drinks. Both ordered a six ounce steak - his a center cut, hers a filet minion; his medium well and hers medium rare. They both had salads to start and when Cheryl ended up with a few drops of Ranch dressing on her lips, Frank joked about her having white creamy stuff on her face in public. He was teasing but her response surprised him. "It wouldn't be the first time," she said with a devilish grin, and then she continued, "and I certainly hope it isn't the last." She finished the statement as she used a finger to wipe the dressing up and then sucking it from her finger. It only added to the eroticism of the moment that she had made no secret of how much she enjoyed giving head and tasting/swallowing his cum. He had seen her perform that exact same motion with his cum on her lips and chin and seeing her do it, even with the Ranch dressing, made his cock throb in his pants. He couldn't help but think how much he'd enjoy it, and how erotic he'd find it, if she'd just slide down under the table and give him head right there. He didn't say anything about it though; honestly, from what he knew of her so far, she might just do it.

They enjoyed their meal and conversation full of sexual innuendos, both knowing that any sexual tension they created was going to be relieved later in the evening. As a general rule they skip desert and after the bill is paid, Cheryl waits to see what Frank has in mind next. The evening weather is delightful and Frank takes her by the hand, leading her down the sidewalk and letting her know his plan was to walk and window shop - unless she found something she liked - through this few blocks of the city. He had a specific shop in mind as their destination, but he didn't mention that to her. He wanted to see what her reaction was when they got to it.

They stopped into several shops with products varying from shoes to clothing and even a kitchen supplies place as they walked. After almost an hour of walking and browsing, they reached the store that was Frank's ultimate goal: a place called the Pleasure Chest. It was an adult accessories store with shelves and wall racks filled with toys and clothing racks displaying a wide variety of sexy clothing.

Still holding Frank's hand, Cheryl stopped briefly at the door and looked at Frank. "Really?" she asked, for some reason sounding mildly surprised.

"Yes, really," Frank replied with a smile, meeting her gaze. "I thought we might find something fun to play with."

"I'm not enough fun to play with?" Cheryl asked, but Frank could hear the playful tease in her voice.

"You're more than enough fun," replied Frank, "but I don't want you to ever get close to bored with me... with our play..." He paused to consider his words and decided that she wouldn't be offended. They were both realists. "And given you background of sexual experience, I kinda feel like I need to keep things new and fresh as much as I can."

Cheryl took in his statement and looked at him carefully. She had confessed her past as a prostitute some weeks back and he had taken it in stride as if it mattered not the least bit to him. He obviously hadn't forgotten about it and was aware of how that year she spent having sex for money might have impacted her appreciation for "vanilla" sex. He was making an effort to make sure the sex life they shared didn't become hum-drum for her. Who was this man? With a smile she finally gave him a reply before pulling him into the shop. "Let's go find something fun!"

There was more to look at in the shop than Frank had thought possible and Cheryl seemed equally entertained by the wide variety of... well... everything. Frank focused on the clothing racks at first, finding and suggesting several sexy items that he thought Cheryl would look good in - and coming out of. Cheryl took his suggestions in stride and gave feedback on each item he suggested, positive or negative, and then pointed out several items made for men, one or two of which made Frank blush. He wasn't even aware he could but he certainly did and Cheryl pointed it out pretty quickly with a devilish giggle.

After they'd gone over just about every clothing rack, Cheryl led Frank over to a wall full of hooks, each holding some type of toy or pack of toys. The available varieties from size to color to electric or none truly amazed Frank. He was no stranger to adult toys but he felt like a total novice when he saw so many toys that he never had any idea existed. Cheryl didn't seem like she was as surprised at the sheer volume available but she didn't seem like she knew the details of all of them either. Pretty soon Frank noticed that Cheryl seemed to be focusing on packs of toys rather than individual toys. After another few moments of her pointing out different packages to him, he further realized she was focusing on anal toys. Not put off at all, Frank gave honest answers to Cheryl's questions and made observations to match hers as best he could. In the end, he encouraged her to pick out the one she was most interested in and he took it up to the register to purchase.

Cheryl seemed mildly surprised at his willingness, maybe due to what she'd chosen. She'd picked the particular package more to see his response than as a serious desire to take it home and experiment with. It was labeled as a "complete anal training and play set." It had three different sizes of butt plug, a half dozen different dildos, all different lengths and thicknesses, and a strap on set that allowed for wearing any one of the dildos included. Idly she wondered what Frank's reaction would be if she pointed out that the strap-on harness was adjustable and she could wear it as well as he could... and then she realized that he had no need of anything strapped on (his 7.5" nicely thick equipment freed him from ever needing to strap anything on to please a woman) and she wondered if he had so readily accepted this package because he was open to her wearing the strap on to use on him.

With Frank carrying the bag, they exited the store, once again hand in hand, and Cheryl walked close to him, bumping her head on his shoulder with a big smile on her face. "Thank you," she said as they walked along.

"For?" he asked in reply.

Cheryl had to think about that for a moment before she could give an honest answer; and the reality was that she was thanking him for an awful lot. How to express all that? "For so much," she finally said. He was quiet waiting for her to expand on that. Finally she took a deep breath and continued. "Thank you for not being judgmental and being so accepting of my past. Too many people would have tried to shame me with it or been critical of me for it." Frank remained quiet because he felt like she wasn't finished. "Thank you for being so in tune with me and enjoying so many things with me, both sexual and non." Another pause... but not done yet thought Frank. "And thank you," Cheryl finished, "for generally making me so happy for the past couple months. I honestly didn't think I'd find this much happiness in a relationship." Frank chuckled after a moment of thought and the sound made Cheryl nervously curious. "What is funny at all," she emphasized, "about my thanking you?"

"There's nothing funny about it," Frank replied, sensing her reaction. "But let me thank you in return."

"For?" she asked, just as he had a few minutes earlier. He thought for a moment to structure his response.

"Thank you for not judging me on my lack of comparative experience and being so willing to help me open myself to new experiences." He breathed and she remained quiet, just as he had. He continued. "Thank you for all of the fun we've had, both sexual and not, but mostly for how motivated you've been about enjoying our physical relationship as much as I want." And then with a final breath he finished, "and thank you for having made me so happy the past few months."

"Wow," Cheryl said with a grin, "that sounded familiar."

"Ya' think?" Frank chuckled. "But I left one thank you out." Cheryl raised her eyebrows in response, displaying her curiosity as to what he had left out. Looking at her to meet her eyes Frank said, "Thank you in advance for the future I'm looking forward to with you." That shocked Cheryl. She hadn't dared to think much about their possible future together but hearing him vocalize his appreciation for what might come... and then her dirty mind twisted that thought and she giggled. It sounded naughty to Frank and he had to ask what had brought that on.

"I was just thinking about what the near future is going to bring," Cheryl said, indicating the bag he was carrying. "Just how much there might be... to cum." Her face lit up with humor and excitement as she finished the statement and Frank matched the look with one of his own. By the time they got back to his car they were definitely ready to get home - her place for the night - to see what the night held.

As Frank drove out of the parking structure, Cheryl let out a big sigh and said, "Damn... I'm so horny."

"So take care of that," Frank said casually. Cheryl looked over at him but didn't do or say anything. Looking at her briefly to see the questioning look on her face he smiled. "We've got about a forty-five minute drive. Get a few orgasms as we go. It's not like your fingers don't work."

"Yeah?" Cheryl asked with a smile.

"Yeah," said Frank. "I'll keep my eyes on the road and my hands to myself," he added.

"Hmm..." Cheryl hummed as she thought. "Well, then..." Without saying anything else, she reached into her small purse and pulled out what looked like a lipstick tube but proved to be a small vibrator. She was petite enough that getting comfortable in the seat of the car took little effort. She leaned the seat back a little bit, pulled her thong off, dropping it on the floor at her feet, and then putting her feet up on the dashboard. Frank heard the vibrator click on as she twisted it and caught glimpses of her reaching between her mildly spread thighs.

Frank had to force himself to focus on driving as the smell of Cheryl's sex began to fill the car. The buzz of the vibrator was audible and he could hear it growing louder and softer depending on how hard Cheryl was rubbing it on her sex, around her clit or up and down her slit. He hadn't even gotten to the state highway before she had her first orgasm and, since she was multi-orgasmic, she had several more by the time they were half way to her place. After the fourth or fifth, he had lost track, she pulled the vibrator away from her pussy and breathed a deep sigh. "You're not done are you?" Frank asked her with a devilish glint in his eyes.

"Not nearly," Cheryl replied, matching his look and smile. "But I'm saving the rest up to enjoy with you when we get home."

At Cheryl's apartment Frank grabbed his overnight bag out of the backseat and followed her up the walk as she carried the bag with their erotic purchase from the Pleasure Chest. Frank knew that as soon as they got into her apartment she'd be in her "game on" mode and he was looking forward to it. She was the only woman he'd ever been with who was so open; had so few rules. He had actually laughed when she did share her two rules. "No bodily waste products and don't cum in my eyes," she'd said. He had laughed and she'd seen the questioning look on his face. "Well don't," she added on. "It stings!"

Once inside Frank locked the door behind them and followed Cheryl down toward her bedroom. She dropped her purse on the hall table as she went and kicked off her shoes just inside her bedroom door. She kept her dress on as she opened the bag and asked Frank to find some scissors in the kitchen's "junk" drawer so they could open the package. Frank delivered and she very carefully cut the plastic, making sure she didn't get close to any of the contents. With it open, she carefully picked out the battery driven toys but dumped everything else in her bathroom sink, turning on the hot water and then leaving it for a moment. Frank just stood and watched as she walked down to the kitchen to the junk drawer and pulled out two ziplock bags that held batteries. When she got back to the bedroom Frank realized one bag had C cell batteries and the other had a mix of AA and AAA batteries.

12