Chelsea's Twelve Days of Christmas

Story Info
A young woman learns to love again.
64.3k words
4.81
57.6k
82
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
xelliebabex
xelliebabex
5,501 Followers

Authors Note: This is my entry in the "Winter Holidays Contest". There are some elements of the BDSM category in this story so if that is not to your taste perhaps choose a different story. If, however, you read and enjoy it please vote and leave a comment. Thank you very much to my friend, Margaret who proofread for me. ~ellie

Chelsea's Twelve days of Christmas

Chapter 1. Innamorata

Chelsea Gillian walked slowly down the staircase into the magnificent ballroom. She was poised and beautiful. Of course, working for over two years to become the woman she was, at this moment, helped to give her the confident air that held her smile in place, despite her anxiousness. This was the life she had chosen, the life she wanted, free from the complications and pain of the life she had walked away from. Accepting a flute of champagne, she moved toward the easel that held the table plan, which would tell her where she would sit for the first of the six courses.

She posed looking over the plan, intentionally letting the figure-hugging sequined gown shimmer under the myriad of lights highlighting her curves. Having found her table she turned to survey the crowd. The event was littered with faces she knew, some more intimately than others. The world she had lived in over the past years had created pathways that crossed with many of the wealthy people in this room. She knew many on a first name basis, but only a select few knew of her membership to an elite sorority and what that meant tonight. Tonight was the pinnacle of what she had worked toward, her graduation, and she was about to reap the rewards.

"I was hoping you would be here tonight," a smooth male voice said making her turn to look at him.

"Harry," she practically purred his name. "Is your fiancé with you? She was always a keen supporter of this cause."

"Unfortunately the trial of our engagement seemed too much for her, it is a difficult role to fill, being betrothed to a man such as me," he smiled self-depreciatingly. "She received a less demanding offer, and I released her from her commitment to me."

"That's disappointing; I had been looking forward to seeing her," Chelsea touched his arm in an intimate gesture of sympathy and understanding. She made a mental note to seek out Eva, the gossipy matron of their sorority, in the next week or two and find out the true story.

"Don't be disappointed, I believe she will be here tonight, with her chosen one," he said easily.

"Ah, well that is good news," she said with a dazzling smile. "You seem unaffected by her loss."

"One cannot lose what one never truly had," he returned her smile. "I will speak with you again tonight but if you will excuse me I see someone I must see."

"Of course," she said withdrawing her hand from his arm.

He gave a slight bow and moved away. Chelsea never ceased to marvel at the man's formality and stiffness. She went in search of her patroness and the hostess of this gala event, to offer her assistance if it was needed. As always there was a group of people clustered around Isabella Ross, but she stopped talking and stepped forward to embrace Chelsea as she approached.

"You look wonderful, darling. There has already been a lot of interest just from your name being on the Innamorata graduation list," Isabella informed her. "I am so proud of you. You are the perfect ambassador for our little school." She linked her arm with Chelsea's and led her away from the small group of people. "I believe we will have much to discuss tomorrow if the early signs are anything to go by," she whispered. "Show no favour to any individual tonight, share yourself around liberally."

"Always," Chelsea said softly and dipped her head in respect to her patroness. "Will Riley be here tonight? I just spoke to Harry, and I am curious," she admitted.

"It was not a good match from the beginning. We brokered an agreement with the second choice," Isabella admitted. "She is beautiful but without the skills most of our graduates possess as you well know," Isabella pointed out.

Chelsea knew better than to argue, so she nodded as they continued to walk slowly. Riley had been one of her closest friends in the sorority, and although she had been there longer, they were often in the same classes, as the other girl struggled with many of the challenges they had been given. Many of the girls taken in by Isabella Ross and her finishing school had nowhere else to go and jumped at the chance the scholarship offered them. They embraced the sisterhood of like-minded women the sorority offered them, as well as the leadership Isabella and her tutors gave them. Many failed to graduate and were found jobs in the retail and service industries. Riley had been one of those that barely made it through to graduation.

They had walked almost a full circuit of the room politely smiling and nodding at the guests. When Riley appeared in front of her looking radiant, Chelsea almost squealed with delight and embraced her.

"It's so good to see you!" Chelsea grinned girlishly dropping her calm, sexy veneer for a moment.

"I've missed you so much. I have so much to tell you," Riley exploded in her usual excitable babble.

"Perhaps later," Isabella intervened. "I believe it is time to take our seats."

"Yes Madame," the younger women said in unison and separated from each other. Chelsea let Isabella steer her away from Riley toward the tables of the ballroom. She had found herself sitting beside Harry at the first table, and he engaged her in conversation almost to the exclusion of the other guests at their table during the first course.

"You're a little older than most of the girls who graduate from Innamorata," he commented.

"Oh? Perhaps I just look older than my years," she laughed lightly.

"Honestly, you look much younger than your years, which is why it surprised me when I discovered your age in the graduation package," he bent his head and spoke in a soft voice.

"My story is a little different to most of the girls Isabella sponsors," she smiled feeling unnerved by the intensity of his gaze.

"Continue," he said in the same soft voice, but she knew it was a command.

"I was flunking out of my third year of university when I met Isabella. I had been recovering from family tragedy and trying to get my life back together when she came in as a guest lecturer," Chelsea remembered her first meeting with Isabella well. "She spoke to me in a way that made sense, and she offered me help in the form of a scholarship to finish my degree. I joined Innamorata once I'd completed that degree. That was two years ago." She hoped she gave enough information to forestall any further questions in their present company.

Harry said nothing as he continued to look at her. He had come with the sole purpose of meeting this woman. He had been considering offering a short-term contract, thinking her to be a beautiful but ultimately brainless woman, like her friend Riley who in admitting she could never be the woman he wanted or needed, had spoken of her friend who was all those things and more. Riley had been a ditzy blonde who covered it well by learning key facts about the people she met. She was beautiful in the Marilyn Munroe blonde bombshell way that attracted him, and he had let his attraction to her overrule his better judgement.

He smiled thinking of Riley. She had been like an excitable puppy, whose decorum often slipped at public events, earning his wrath. Her interests were shallow and once the fun facts she had learned on a subject were dispensed with she giggled and flirted to hide the fact that she knew very little about current affairs or the people with whom they often socialised. When he and Riley had finally had their heart to heart talk, she had explained that without Chelsea's constant assistance she never would have made it to graduation. She knew that even at her best she couldn't be the perfect Innamorata girl he wanted and suggested he would be much happier with a girl like Chelsea, while she would be happier with a man who had a different expectation of her.

Over the following six months, as he frequented Isabella's social events, he had realised that Chelsea was an enigma and he was glad to have been seated beside her for this first course. His initial expectation that she would be as ditzy as her friend had been squashed long ago and he found himself intrigued by the woman. He realised he had been staring when she suddenly looked away and began to speak to another person at their table.

"I'm sorry," she apologised to the man sitting nearby who has asked her a question. "I didn't mean to be rude, I'm not usually so easily distracted," she laughed lightly, feeling unsettled by the look Harry had given her. "Yes, I am one of the graduating class," she answered his question.

"Do you have plans for what you will do next?" The lady sitting beside him asked. They were quite obviously a couple and seemed genuinely interested in the story of one of the graduates, who had enjoyed the benefits of a scholarship provided by the foundation they supported.

"I am taking a small break over the holiday season to look at my options and decide what to do next," Chelsea answered noncommittally. "I feel like I have had the best education possible and some of the offers I've received are very tempting."

"What is it you seek? What would make one offer stand above the others?" Brock, another gentleman she recognised who sat at their table asked.

"I asked myself the same question coming up to graduation," she admitted. "I would be lying if I didn't say all of the clichés like fame and fortune but I believe what I am looking for is a challenge. I am looking for something that will challenge me both physically and mentally. I think we need to be challenged, to feel that sense of achievement or satisfaction when a task is accomplished. Don't you?"

"As long as it is the task that is challenging and not the person," Brock agreed reluctantly.

The conversation around the table continued, as people took up the idea of what constituted a challenge, and that people themselves could be challenging. During the thirty minutes Chelsea spent at the first table, Harry continued to study her making her feel mildly uncomfortable. He was silent for the most part as if considering everyone's point of view.

"I find this time of year a challenge," he finally added to the conversation. "So many social events over the holiday season. I am happier at smaller more intimate occasions than large events like this. T'is the season as they say and there will be no respite until weeks into the new year."

"Ladies and gentlemen," Isabella's voice sounded through the ballroom making the talk at the tables cease. "While the graduates are moving to the next table can I direct you to the envelopes on your tables. These hold the raffle tickets for the end of night prizes and the silent auction bidding cards that you can give to runners, who warn you when one of the items you are interested in is closing."

Chelsea moved to the next table as Isabella spoke, she knew which table numbers she was required to sit at and dutifully went to the next one on her memorised list. Picking up on what Harry had said before she left his table, she started a conversation with the couple near her at the next table about the holidays, being a particularly social time of year for philanthropists like themselves.

"We have cut back on the organisations we support publicly this year," an elderly lady said sadly. "It can become very overwhelming. We are getting on now and have grandchildren to spoil, so we decided to be silent donors to more than a few of the foundations."

"I am sure your presence will be missed greatly, dear lady," Graham, a man she recognised, said with genuine warmth. "I am sure Isabella is grateful that you continue to support her work with the young women who so desperately need these scholarships."

"We enjoy this one immensely, in this day and age, at least one small corner of the education system is still pushing etiquette and breeding. Too many young women sell themselves too cheaply, take Chelsea for example, her gown is beautiful and classical, she doesn't have to cheapen herself by wearing something revealing or see-through to attract attention. All eyes are on her because she has poise and grace which makes her beauty shine even more radiantly."

"I could not have said it better myself," the elderly gentleman beside her said with a wink. "In fact, we were so taken with one of the school's graduates a few years ago we adopted her. She's the sweetest girl you would ever meet," he smiled slyly. "Perhaps she could use a sister," he chuckled.

"I'm sure any girl would enjoy being adopted into such a warm and loving family," Chelsea said, not missing a beat. Realising that the girl was not looked on in the traditional sense of a daughter. The arrangement was not one she had thought about, but she would consider it depending on the offer. Adoption was perhaps even more legally binding than marriage and held similar benefits for a girl looking for safety and security in her future. The arrangement certainly had more to offer than becoming a mistress to one of the wealthy power couples in the room. "The holiday season is a good time to be with family both new and old," she said with an odd catch in her voice.

The sponsors and patrons of Innamorata seemed to have been clustered around the tables Chelsea visited during the evening, and they didn't appear shy about admitting their patronage of the sorority. Several of the men she had met during their infrequent visits to Isabella at the school for social events.

Chelsea had enjoyed the evening immensely and had been attentive and flirtatious with each of the people at the tables she sat with to enjoy one of the six courses. Several of the men had intrigued and attracted her and as the legitimate portion of the evening ended with the final auction piece; a DJ began to play music, and the dance floor was cleared of the tables that had held the auction items. This more relaxed time of the night enabled the prospective bidders to meet the graduating women and signal their intention to make an offer. It was also an opportunity for the women to show their interest and make a lasting impression on those they might favour.

Having been told to show no favour, Chelsea sought out Riley, hoping to find out what had happened between her and the great Mr Harrison Drake, or Harry as they knew him. She had felt that intense gaze on her throughout the night. Tall, dark and brooding, he was stiffly formal and extremely hard to read.

"You seem in a hurry to get away, Miss Gillian," Harry moved into her path before she could reach her target.

"It's been a long night, and I find myself needing to powder my nose," she said smoothly.

"Then I will not detain you. I hope you can find a spot for me on your dance card when you return?" he asked.

"You are the first to ask so that the honour will be mine. Thank you, kind Sir," she slipped into the formal speech he always seemed to use. He gave one of his half bows and moved out of her path, allowing her to continue on her way.

Chelsea gave Riley a meaningful look as she walked past her on her way to the bathrooms and hoped she would follow. When she came out of the stall, she had been using, Riley was standing at the mirror fixing her lipstick.

"Oh my God, it's so good to see you! I have missed you so much," Riley exclaimed tossing her long blonde hair as she turned to face her friend.

"Tell me everything! Just do it super quick because at least one person is watching for my return," Chelsea grinned. "Start with what happened with Harry."

"Absolutely nothing," Riley sighed, "I was not what he wanted, well outside of the bedroom anyway," she said with a giggle. "He works long hours and reads a lot and asks so many questions about stuff I had no idea about. The sex was phenomenal, but we had nothing else in common. I think he was as bored with me as I was with him. We agreed it wasn't a good match, not for marriage anyway, and neither of us wanted the alternative. You are more what he's looking for than I could have ever hoped to be."

Chelsea nodded. Being a mistress to a man of wealth and power was a viable opportunity and one she still considered a good option. She didn't want the emotional entanglements that came with a true marriage. She wanted a marriage of convenience that she could treat as a business deal. She wanted the name and status that came with marriage, to one of the men in his room and she was prepared for what she would have to do to earn it and keep it until death do us part. Love did not factor into the equation for her, and if boredom was the worst that Riley had to say about Harry, then perhaps the stiffly formal man could offer her the type of agreement she wanted.

"You seem happy now," Chelsea said as she finished washing her hands and took her lipstick from the small purse she carried.

"Oh yes, beyond happy. It's everything we ever talked about and more," Riley confided. "I think I might even love him." She blushed as Chelsea raised an eyebrow.

"I'm not surprised, your emotions always overrode your brain," Chelsea teased and hugged her friend. "I'm so happy for you, I have to go, I hope we can catch up properly soon, though."

"You'll get an invitation to the wedding in February, but I am hoping you will be in a situation that allows to you be my bridesmaid," she grinned.

"I'd love that. Let's keep our fingers crossed," Chelsea laughed and left the bathroom with a wide smile. Perhaps she could have that written into any arrangement she made. She had two people she cared about in this world, and Riley was one of them.

The crowd had thinned considerably as the clock approached midnight and most of the supporters of the legitimate arm of Isabella's foundation left the venue, leaving those who were interested in the Inamorata's true purpose to continue negotiations. The real prizes of the evening were available only to the few who were privy to the operations of Innamorata and what they offered the exclusive bidders.

She could see Harry speaking with Isabella as she made her way back into the ballroom. Chelsea hesitated momentarily unsure of whether to interrupt them or not. He had asked her to dance signalling his interest, and it would have been rude of her to ignore the request and take another, but she didn't wish to interrupt, what could have been a sensitive negotiation. She was saved from having to make the decision when Isabella looked up and saw her, then indicated with a slight wave of her hand that she should join them.

"It's been a lovely evening," Chelsea said as she approached Isabella.

"It has and a very successful one for all concerned," Isabella replied with a small smile. "If you will excuse us please, Mr Drake, just for a few minutes," she inclined her head toward Harry.

"Of course," he gave his stiff half-bow and moved away from the women toward the lounging area where he engaged in conversation with another couple.

"Madame is there a problem?" Chelsea asked quietly.

"Quite the opposite, sweet girl," Isabella smiled graciously. "Let's get some fresh air shall we?" She linked her arm with Chelsea's, and they walked toward the outdoor area of the riverside ballroom. "There are several proposals for you to consider. However, there is an offer for a very lucrative two-week engagement during the holidays," she paused to consider her words. "Perhaps the wrong wording there, there would be no official proposal or immediate offer of a future beyond the two weeks, you would be a live-in girlfriend as such with all of the perks that might entail. It will give you the time to consider the proposals offered tonight for a more permanent arrangement."

xelliebabex
xelliebabex
5,501 Followers