Cheryl Reconnects with Her Past

For those who read the Kingston Surprise series, this is another description of adventures Cheryl has enjoyed. Loosely based on actual events this series will be embellished to, hopefully, provide more enjoyment for the reader.

At the time of this story, Cheryl and Bill were a happily married couple in their late 20's. During their nearly 10 years together, after meeting as college freshmen, they had enjoyed a wonderful sex life together. Bill knew, virtually from the time he met Cheryl, that she was a sexual submissive who reveled in being on display and being available to serve the needs of others. Cheryl enjoyed the slutty feelings that rolled through her whenever she thought about their sexual play or heard Bill tell her about their next adventure.

From the beginning Cheryl and Bill had enjoyed a sexual relationship that involved others. It started with Bill sharing her with a roommate and his landlord then continued with exploring the swinging lifestyle. Multiple partners were almost an addiction for them and something that aroused Cheryl even more than it did Bill.

Cheryl offers condolences to an old boyfriend

Cheryl was doing her daily check of posts on Facebook one summer morning and noticed that Randy, an old high school boyfriend, had posted that his Mother had passed. Funeral details indicated that a memorial service would be held in 10 days in her former home town. Cheryl's Mom and Randy's Mother had been best friends. Since Randy had attended her Mom's funeral several years earlier Cheryl thought it only proper she return the gesture.

It didn't hurt that Randy had been an intense part of her teen years. It was he who first brought out Cheryl's sexual needs and their sexual relationship had been strong and, in one form or another, a daily experience. Randy was very dom and took Cheryl from being an inexperienced virgin to becoming an insatiable and submissive sexual being. Randy's problem was that he was always looking for the next hot piece of ass and was never faithful to Cheryl once he had her hooked. Finally, in the late summer before she left for university, he dumped her for his next conquest leaving her frustrated and confused.

With a mix of emotions she said to Bill. "You remember my old boyfriend, Randy. His Mother has died and I really think I should go to the funeral. She and Mum were best friends and he did come to Mum's funeral." Even as she spoke Cheryl felt little shivers go through her as she thought of seeing Randy again.

Ever the supportive spouse, Bill said, "Of course baby, that sounds thoughtful". Knowing of the intensity of Cheryl's relationship with Randy, Bill smiled. "You wouldn't be thinking of offering more than condolences would you?" Seeing her quickly blush, Bill got his answer.

"Oh honey, I don't think of stuff like that all of the time!". Cheryl couldn't help the little smile that came to her face as she turned to leave the room. Of course, Bill's comment only put more thoughts in her head and she knew he was actually encouraging her thinking.

Cheryl made arrangements to stay with an old girlfriend on the Friday and Saturday of the funeral weekend. She arrived Friday afternoon and the rest of the day was spent recalling the old high school days and laughing about the good times. After a lazy Saturday morning, Cheryl headed to the funeral home for the service. She couldn't believe how her heart beat at the idea of seeing Randy again. She told herself this was an opportunity to pay respects to a lovely lady and her family but couldn't help wondering how Randy would react to her coming.

She caught glimpses of him as she waited in line. Her stomach flipped seeing that he was as handsome as ever and had maintained his muscular build. Cheryl couldn't stop from blushing when he looked past several in the line to smile and wink at her. His hug and kiss on the cheek only made her heart race more. They had little time to talk in the line but he told her he wanted to see her at the reception.

At the reception Randy spent as much time as he could, between interruptions from guests, talking with Cheryl. "Cheryl, you look amazing! I swear your body has gotten more incredible with age and you are the most beautiful girl here!" Randy was pleased to see she was wearing a top that showed a generous amount of cleavage and a skirt that showed her endless legs. He smiled to himself, feeling certain she had worn such an outfit on purpose. Once a slut, always a slut he thought. Plans for the rest of the weekend began to formulate in his devious mind even as others offered their condolences throughout the reception.

Cheryl couldn't help herself. Randy's intense look and closeness built sexual energy and affection within her.

Randy took Cheryl aside as the reception came to an end and apologized that he hadn't spent much time with her. "So sorry we didn't have more time to talk Cheryl. This has been a busy day. We are having a family dinner tonight but Mom left some things she wanted you to have. Is it possible you could come over to my place tomorrow before you head home so I can give them to you? Besides it will give us a little time to catch up." Of course, there was nothing Randy's Mom had left for Cheryl but he had every intention of seeing if Cheryl was as hot a fuck as she had been when they were together.

Cheryl couldn't believe how quickly she said yes, realizing she was looking forward to catching up too. "Of course Randy. I am not in a rush to get back. Thanks for asking."

With a quick kiss on the cheek, Randy said thanks. He gave her a piece of paper with his address and phone number then turned to say good bye to other guests. Cheryl left with a smile that would not go away.

Cheryl could barely concentrate Saturday evening as her girlfriend continued her recall of incidents and people from their school years. She finally said that she was tired after a long day and went to bed. In truth, she could hardly wait for sleep to come and her visit to Randy's occur. He had been a prick, dropping her for that blonde fuck doll that summer but, with Bill's help and love, Cheryl had moved on. What she couldn't forget were the things Randy had taught her to do and how she had reveled in his control of her body and thinking. Cheryl wondered if Randy had moved on too or if he wanted more than a chance to chat. Her smile couldn't be suppressed as drifted off to sleep.

Morning came and Cheryl leapt out of bed and had a quick breakfast with her girlfriend before telling her she was going to clean up and head back home. Cheryl smiled throughout her preparations. In the shower she made sure to clean every part thoroughly and shaved her pussy to its smooth best. She put on enough make up to just a hint of sex and chose a button front blouse to go with a mini skirt and high heeled sandals. Underneath she wore a sexy sheer bra and thong. Looking in the mirror she blushed knowing she had packed these clothes specifically in case the opportunity came to see Ricky alone. Whether she realized it or not Randy's control over her was still very real. That fact would become so clear in a very short time.

After hugs goodbye, Cheryl pulled out of her friends' driveway and headed to Randy's place. She giggled when, at a red light, she casually undid one more button on her blouse which showed more cleavage and allowed a tantalizing view of her bra.

Cheryl's heart was racing as she pulled into a rural, executive subdivision. The homes were all massive and on huge lots of at least 10 acres. Randy had clearly done well for himself in the last 10 yrs. Taking a circular drive she stopped at the front of a gorgeous tudor style home surrounded by immaculately landscaped grounds.

She only begun walking up the steps when Randy opened the door wide. "Cheryl, I am so glad you were able to come by this early. This will give us lots of time to reconnect. I hope you are able to stay for a while!"

Cheryl couldn't help but smile broadly as she blushed. "Randy, you certainly haven't lost your charm. I didn't want our visit to be rushed so came early. I hope you don't mind. I am not in a rush so we do have time to get reacquainted." As she spoke she could feel her stomach flipping as she tried to walk the last steps without tripping.

Randy reached out his hand to Cheryl, helping her up the stairs. As she came to the one he was standing on, he drew her to him for a long, full body hug and then a kiss on the cheek. "You look even better than yesterday and you looked amazing then!! You truly have become even more beautiful and alluring, I was a fool to have let you go back in the day. I hope we can move past that and be friends again." Randy was smiling inwardly. It was obvious from Cheryl's choice of clothes that she wanted to impress him and was not here for a quick visit. Her flushed face and partially unbuttoned blouse were dead give-aways that she was aroused. Randy was convinced he would be able to put into place his plan for the day with positive results. He'd had many women in his time, was just off his second divorce, but Cheryl had always been a hot memory. Maybe it was because they had been teens when life is fresh and exciting or because she had so easily become hooked on exhibitionism and submissive sexual behaviour but his mind had been working overtime since her email saying she would be attending the funeral. Randy had never lost his need for sex in many forms nor his need to be dom in that sex play. He had used women, including his second wife (which led to the divorce), as sexual toys to entice clients and close deals. He was in real need of a new whore that could serve his business well. Randy wanted to fuck Cheryl again but if she could be of use in his business then that would be a bonus.

"Oh Randy, that was so long ago. We are grown up adults now. I am in a wonderful marriage with Bill that meets our needs and has helped us both grow. I am sure we can be friends again. There are two many good memories to focus on the break up. How about you Randy, where is you wife?"

Clearing his throat Randy said, "Well, truth is I have been divorced for almost 6 months now. We weren't married too long before we had disagreements and we decided to call it quits. This big old house can get lonely at times but I am managing. Work has been going great and that has really kept my time occupied. Enough of that, let's go in and enjoy catching up."

With that Randy put his arm around Cheryl's shoulder, held her to him and walked her through the door. There followed a quick tour of the house which left Cheryl impressed. There was a central and massive great room that included a two story cathedral ceiling and windows that over looked a beautiful patio, pool and party area and then a groomed field. Off one side of the great room was a large games and theater room with bar while on the other side of the great room was the largest master bedroom Cheryl had ever seen. She was taken by the super king-size bed and the many mirrors in the room. Cheryl giggled and wondered what secrets this room held.

Randy picked up on her response. "Penny for your thoughts!" he said as he gave her a squeeze.

Cheryl blushed furiously at been caught. "Oh, you know, this just looks like a bedroom built for more than sleeping!"

"You haven't changed a bit and you know me so well Cheryl! Let's just say what happens in the bedroom stays in the bedroom!" Randy couldn't help but congratulate himself on accurately gauging Cheryl's sexuality still being very close to the surface. She would find out later that there were audio and video recording devices in every room!

The tour was finished with viewing four en-suite bedrooms all with views down to the extensive great room.

"Why not have a seat here at the breakfast bar. I have a surprise to show you. I know it isn't noon yet but can I get you a glass of wine? I am going to have some and, like you said, we are grown ups now."

Cheryl didn't normally drink at this hour but reasoned that a glass of wine might calm her down a bit. "Sure Randy. As long as we watch our limits that should be fine."

Randy helped her onto one of the bar stools at the breakfast bar which overlooked the kitchen and also had a large window view out to the back yard. He smiled as Cheryl struggled to get up on the seat and settle herself. Her mini skirt rose past mid-thigh and her breasts moved provocatively as she moved onto the seat. Damn, he thought, this girl is even sexier than when I had her! Randy was more determined than ever that he would have Cheryl naked in his bed before the day was done.

Randy poured two glasses of wine, gave Cheryl a quick peck on the cheek, then excused himself as he went to the games room.

He picked up two photo albums he had been saving for this occasion. The first album contained many pages of photographs of Cheryl, he and Cheryl and the two of them with friends from back in the day. In all cases, Cheryl was wearing revealing clothes and bathing suits he had insisted she wear for him. Back in the day, he so enjoyed showing her off to others and her love of being on display became a big part of their relationship. The second album again contained many pages of photographs both polaroid and digital. These pictures though, were far more revealing. From the beginning of their relationship he had convinced Cheryl to pose in very revealing clothes and naked for him. She had taken to that part of their relationship with excitement. There were many pictures of her naked or nearly so indoors and out and in provocative and pornographic poses. Included were pictures of her during and after sex. Shots of her sucking his cock, with his cock inside her and with cum all over her were the climax towards the end of the album. Randy had albums like this of all of the women he enjoyed over the years, but planned to give Cheryl the impression this was a keepsake because of their great relationship. He hoped the albums would have Cheryl in the mood for hot sex in short order.

Randy returned to find Cheryl sipping are wine and smiled when he noticed it was already half gone. "This is going to work our just fine!", he thought to himself.

Randy put the albums on the breakfast bar, refilled Cheryl's glass then picked up his own for a toast. "Here's to being friends and to great memories."

Cheryl returned to toast with a broad smile. "What have you got there?" she said as she motioned towards the albums.

With a flourish, Randy motioned to the albums, "These are my special keepsakes of our time together. Even though it ended badly, and all my fault there, we did have some wonderful times. I have kept these albums to remind me of how amazing you were. When I feel down all I need to do is pick them up and I will smile for days after."

"Let me put this first one in front of you and we can take a trip down memory lane together."

Randy put the first album in front of Cheryl then moved close to her side and put an arm around her shoulder. He intended to not only offer suggestive commentary as they looked at the pictures but also subtle physical contact that would help get Cheryl in the mood.

When she saw the pictures on the first page, Cheryl exclaimed, "Randy! You didn't! You saved all of these pictures from when we were dating!? I can't believe you kept these all this time."

For many minutes there were lots of laughs and comments about outfits and some of the friends in the pictures. Randy made sure to point out the sexiest of the outfits and made comments about Cheryl's physical development over the nearly three years they had been together.

As he did, he made sure to lean in for more physical contact as he pointed out different pictures and poses. The hand on her shoulder moved gently up and down her arm and along her shoulder to caress her neck. He was pleased to note that Cheryl readily accepted his touches, even leaning into him when they both remarked about different pictures.

While Cheryl was lost in looking at the pictures Randy made sure to keep topping up Cheryl's wine glass. As they neared the end of the first album, he chuckled to himself as he drained the first bottle into her glass. He had yet to finish his first glass. Cheryl had always succumbed easily to his words and touch. The wine was going to make things even easier. He thought, "I am going to have this slut in bed before we get through the second album!"

As Cheryl came to the last page of the first album, they both laughed. Randy pivoted the bar stool and moved in for a hug, He was pleased to feel her lean into the hug and matched his enthusiasm.

"We did have some good times didn't we Cheryl? And, weren't we the fashionists!! I can't believe some of the styles that were popular in the day!"

"Yes we did Randy. I am so flattered that you kept those pictures all this time!"

"You were a huge part of my life back then. I have always kept those pictures to remind me of our fun and to remind me what an incredibly beautiful and sexy young woman you were! What makes looking at them today so special is that you are even more beautiful now and have a body that would make any woman envious!"

That remark prompted a second hug, then Randy subtly grabbed the empty wine bottle and replaced it with another from the fridge.

Cheryl, feeling a little light headed, watched Randy move and her heart raced. Seeing the pictures brought back so many memories of laughs and exciting times. That Randy had saved the album just for her made her smile. She thought, "I guess there were good times. We really were a good pair back then."

Randy quickly returned with the wine and filled Cheryl's glass. He said, "I could use another hug!" and leaned into Cheryl who enthusiastically responded. As they broke, he tested the waters by giving her a quick kiss on the lips. Cheryl's eyes looked into his and she returned a light kiss then turned back to the bar.

Cheryl leaned to grab the second album. "I want to see more pictures."

Randy quickly resumed his position beside her and waited for Cheryl's response to the more graphic nature of this album. Cheryl became quiet as she looked at the first few pages. She was slower moving from page to page. As she did Randy would reach his hand to point out a certain picture, pose or location. Each time he pointed he made sure to lightly brush his arm against the side of her breast all the while whispering graphic descriptions of the pictures.

"Look at how firm your breasts were in those days.", "Do you remember how exciting it was to get naked in the woods and take those pictures?", "You were such an enthusiastic cocksucker back in those days.", "Do you remember the day we shaved your pussy?", "We couldn't get enough of each other back then could we?"

It was a sensory overload for Cheryl. The pictures brought back such exciting memories, Randy's subtle brushing against her breast made her stomach flip, his whispers describing various pictures brought them to life and the wine she was consuming all had her squirming on the bar stool. Several times she had to close her eyes and bite her lip as little shivers went through her.

As Cheryl got to the last couple of pages, Randy leaned down to gently kiss along her shoulder and neck. As he did, he softly cupped her breast. He was rewarded as a soft moan left Cheryl's mouth and she leaned back into him.

Randy slowly turned to bar stool until Cheryl was facing him. He leaned down and took her head in his hands. Cheryl looked at him with lust in her eyes and then they were kissing with such intensity. Both mouths opened to welcome the tongue of the other. Once again, Randy smiled to himself when he heard Cheryl moan with such need.

Randy broke the kiss and said, "I think we need to move to bedroom."

Cheryl was so lost in the moment that all she could do was nod and let Randy take her hand and lead her to the bedroom.