Heather's Pleasure Day

This is a 2018 Winter Holiday Contest entry. If you enjoy the story, please consider voting.

I'd like to give a very special thanks to Carlie for editing and improving the story. She was so great to work with. I truly appreciate her help.

And as always, I welcome your comments, feedback and emails. I love hearing from you.

Enjoy.

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Heather let out a huge yawn as she stretched in bed and rolled over expecting to find her husband peacefully sleeping. Instead she found a pile of rose pedals and a folded note with her name written in calligraphy on the cover.

Had it already been a year? Her body was absolutely giddy with excitement as she opened the card and read it aloud.

To my beautiful, amazing wife,

Enjoy your special day. I splurged a bit this year, but you deserve this and so much more.

I want you to savor every single second and live out your dreams. Just remember there's only one rule to follow.

You are my best friend, my partner, and my lover.

Enjoy!

Forever yours, Paul

Heather's heart fluttered. This was without a doubt her favorite day of the year. It started out years ago when they were first dating and working multiple jobs just to make rent. Exhausted and unable to take any real vacations, Paul coordinated a day just for Heather to relax. Since they didn't have much money, the first time he gave her a picnic in the park where they sipped cheap Champagne and he let her spend the afternoon peacefully reading her books in the comfort of their tiny apartment, which he had decorated temporarily as her private sanctuary.

That was years ago and much has changed since then. They both completed their MBAs, eventually rose to higher and higher positions in their companies and bought a nice condo in a downtown high rise. It was still a fairly modest place, but the master bedroom alone was bigger than their whole first apartment.

Even with all that changed, many things stayed the same. Like their work ethic. They lived their whole adult lives working around the clock and that would never change. It's one of the reasons they both rose to the ranks of SVPs in their companies. To them it was just doing what was necessary and didn't even feel like work.

They still didn't treat themselves to any fancy vacations, even though they could afford to travel the world without a thought. They chose to stay home so they wouldn't miss out on work. It was a bit foolish, but it was a part of who they were.

As a replacement for the sacrifices they made year-round, they continued with the tradition of having an annual special day just for Heather on the Friday before Christmas where Paul curated a day of extravagant and indulgent surprises. Paul dubbed it Heather's Pleasure Day years ago and the name stuck.

Each year Paul outdid himself planning something more and more elaborate than the last. After the first inaugural year with the picnic, Paul planned fancier dinners, entertainment and the best foods money could buy. But in the last few years, a new development started to take place. Slowly, as if seducing her one year at a time, Paul introduced more and more teasing, sexy activities for the indulgent day.

One year she was treated to a burlesque show with choreographed male dancers joining in. The kind of show didn't exist. He had to have had it specially created just for Heather. The year after that, he arranged for topless men to serve her grapes as she watched her favorite movie in a rented-out theatre. Each year, he pushed the envelope a little more getting her out of her comfort zone. Slowly she began realizing it was something she always wanted but never admitted to herself. A side of her she had buried deep down, covered up by work and responsibility and societal norms.

But not on this day. Her body practically quivered at what he might have in store for her. The words lingered in her mind, they only had one rule to follow. She knew the rule well: whatever happened during the day, you couldn't mention it to anyone. Ever. Not even Paul.

It was both tantalizing and frustrating at the same time. It was a way to remove the guilt of enjoying such extravagant luxury without having to worry about it. There were times she wanted nothing more than to tell all her girlfriends of the luxurious treats of the day and was frustrated she couldn't. And there were times she was grateful she couldn't share what happened. It was an awfully delightful catch 22. She squeezed her legs and held the letter to her chest, giggling playfully.

There was one final note on the letter.

P.s. If my timing is right, your first surprise should be just arriving now.

She was interrupted by a knock on the door. Her heart raced.

"Come in." She said anxiously as she pulled the sheets up and over her chest.

A handsome gentleman walked in with a tray. "Breakfast in bed for the lady of the day." He said with a smile. He looked to be in his mid-twenties, clean cut, muscular but not too much.

Mmm, where did Paul find this guy?

"Thank you." She smiled and held the sheets tightly to her chest. The fact she only had on a thin nightgown that covered very little of her was not lost on her. It was a bit nerve wracking having a complete stranger in the confines of her own private bedroom where only a few thin pieces of fabric separated her naked body from him, but it also gave her butterflies for what was to come.

The young gentleman set the tray over her lap and lifted the cover off the plate. "Eggs Benedict, toast and Champagne. Just as you like." He said softly. "Is there anything else I can get for you at this time?"

She smiled and shook her head. "I'm fine, thanks."

"Very well. Here is some reading material for you. I will be back to check on you in a bit."

He placed a stack of magazines next to her. She flipped through and saw everything from Popular Science, to US Weekly, to Playgirl. She blushed at the thought of knowing that strange man was aware she had a magazine filled with naked men for her viewing pleasure. Paul knew she care for watching much porn, and figured his main intention was just to make her blush.

She slowly ate her breakfast and sipped Champagne while she flipped through the magazines. By the time she was finished eating, she had skimmed through all of the magazines. Almost all of them.

She saw the Playgirl sitting next to her and shrugged her shoulders. What the hell...why not? She thought to herself as she picked it up and again giggled like a school girl.

She didn't really know what to expect, but it was not quite like she imagined. It mostly had photos of gorgeous men half clothed. Heather was both relieved and disappointed. Just seeing random penises was not really a huge turn on for her, but now that she got this far, she was hoping to see something gratuitous.

She turned the page and the centerfold dropped down. She had to set her Champagne down as she unfolded the extra pages. "My god!" She said aloud as she saw a lean, muscular guy sitting in a chair. He was all abs, save for his erection that rested against his chiseled stomach.

Her eyes were practically popping out of her face as she took in the sight.

"Everything to your liking, ma'am?" The young gentleman asked.

"Gah!" She screamed as she had no idea he had returned. Heather rested the magazine on her lap, with the photo sticking up. "You gave me a start."

"My apologies." The young gentleman smiled and took notice of the centerfold image on her lap. "Was everything to your liking?"

Heather glanced down and realized the giant dick she was just staring at was still on display. Her normal defenses were about to kick in, denying she was looking at anything remotely dirty. "Yes, everything was very much to my liking." She said instead and picked up the magazine, openly thumbing through the rest of the pages.

"Very good, then." He walked over and took her tray, and saw Heather take in the sight of more naked men. After he cleared the food away, he brought her robe from the closet and held it out for her.

"What's this?" She asked wondering where the morning would take her.

"It's time for you to get ready. You can shower now, and your ride will be waiting for you in front of the building whenever you're ready."

She set the magazine down and stood up. Her thin nightgown barely covered her erect nipples that were practically poking through the silky fabric. It gave her a whole new tingle knowing he was looking. "Everything to your liking?" She asked him in the same tone he had asked her a moment ago.

He blushed and returned his gaze to her face. "My apologies, ma'am. That was rude of me." He said and turned away while she finished slipping her robe on over her shoulders.

"You didn't answer my question." She said daringly and held the front of her robe open and asked again. "Everything to your liking?"

He understood the game now and glanced at her barely covered body, staring noticeably at her hardened nipples through the thin nightgown. "Very much, ma'am. Very much."

She blushed and cinched her robe. "I thought so." Where did this attitude come from? She wondered. "I'm going to shower now. I will be out in a little while."

He nodded. "If you need anything at all, please don't hesitate to holler for me." And he left the room, shutting the door behind him.

Did he really just offer to help her shower? She giggled to herself realizing she was probably reading too much into his innocent comment. This day had barely started, and she was already swelling with anticipation and butterflies. She never would have been comfortable with a strange man in her bedroom even just a year ago, let alone say those things to him. Yes, this special holiday had slowly started to change her over the years and it was making her giddy knowing she was getting more confident and daring little by little.

Heather went into her en-suite bathroom and disrobed. She stared at her nude form in the mirror after she lifted her nightgown over her head. Staying fit had always been a priority, even with her busy work schedule. She was proud of how she managed to keep a flat stomach while most of her contemporaries had not. Her full breasts hung freely, plump D cups with soft, dark pink nipples that stared back at her in the mirror. She always thought her chest was her best feature, but Paul insisted it was her ass, which she had to admit wasn't half bad either.

Finally, she looked lower, focusing on her hips and contours that led inward to her soft slit. She was a bit amazed she had neglected it for so long, it was covered in a fuzzy patch of hair. In fact, it had grown so full, her slit was barely visible under the soft, thick curls. She debated shaving for the day but was too eager to see the next surprise to spend the time on it. Besides, no one's going to see that anyway, she thought to herself.

Even her shower seemed to be extra sensual as she cleansed her body thoroughly. She must have washed her soapy breasts for several minutes before even realizing it. Her sex between her legs was almost too sensitive to touch as she'd softly run her fingers over it and return to her breasts, teasing her nipples and then back down to her slit.

Enough! She laughed to herself and shut off the water. Why pamper yourself when you have a day full of surprises ahead of you?

When she stepped out of the shower, she saw there was a new dress laid out for her on the bed. It was a strong crimson red, that had an almost intoxicating quality to the touch. Right next to it on the bed was her favorite pair of lacy, green panties.

A few thoughts ran through her head. She was in love with the dress, but she got an even bigger kick knowing that gentleman was in here picking out her dress while she was naked and in the shower a moment ago. Plus, he had to have gone through her underwear drawer to pick out these panties. It was such a silly thought, but she loved it all the same.

Quickly she slipped on the panties and started to slide into the tight dress. It wasn't until it was halfway up her torso when she realized there was no bra set out for her. Heather was not normally one to go sans bra and was a little concerned her headlights would be shining, as she liked to say, but pulled up the dress over her shoulders and gave it a try anyway.

She was right. Her headlights were indeed shining through the thin fabric. It felt like something Sofia Vergara would wear on a red-carpet event. She looked in the mirror and took note of the unfamiliar woman staring back at her. Who is this debonair debutante? She thought and giggled, doing her best to keep her calm, sophisticated demeanor.

"Oh Gaston? Gaston? Could you come in here?" She called.

After a moment the young gentleman returned. "Were you calling for me?"

"Gaston! Of course, I called for you. I was practically screaming your name."

"My name's Jim..."

"Gaston, what do you think of this dress?" She said paying him no mind and added a little smile to let him know she meant no offense.

"It's quite becoming, ma'am. You'll be the envy of all the ladies wherever your day takes you." He said.

She feigned light blushing, "Oh stop it, Gaston." She adjusted her chest in the dress. "What about these?" She asked.

"Oh, um they are quite nice." That caught him off guard and he wasn't sure how to answer.

"Gaston, of course they are. I was asking can you see anything...like my nipples?"

"Oh. If I'm being honest, yes, they're quite noticeable." He said uneasily.

"Perfect." She said and threw on her long overcoat, leaving it open to only half cover her chest.

"This way, ma'am." He took her arm and escorted her to the elevator and down to the lobby. "Your chariot awaits." He gestured to the stretch limo just outside the building.

Her heels echoed along the tiled floor of the lobby as she walked toward her limo with a growing confidence.

"Good morning, madam." The chauffeur said as he tipped his cap and opened the door for her.

Heather climbed into the limo and laughed at the unnecessarily long cabin. You could probably fit 12 people in here, and yet it was just her. She helped herself to the glass of Champagne already poured for her.

"Driver, where are we going?" She asked curiously.

"You'll see, madam." He said through the intercom system.

Truthfully, she wondered if he even knew. Her guess was he was receiving GPS directions and wasn't aware of the destination. That was just like her husband. Keep everyone guessing so no one could accidentally spill the secrets.

Eventually they pulled up to a shopping mall. It was hard for her to hide a little bit of disappointment. She was hoping for something a little more impressive. A little more extravagant.

Heather stepped out and found a new gentleman ready to take her arm and escort her into the building. "This way, ma'am."

Once inside she couldn't hold back her curiosity. "What's the catch? There has to be something more than shopping."

"No catch, ma'am. It's just shopping I'm afraid." He said plainly, and they started to walk toward the stores.

She had to mentally take a step back. Shopping was still fun. Maybe she was just expecting too much. As they started to walk the halls, something didn't seem right. "Where is everyone? This mall is usually a madhouse at this time."

"It usually is. But it's been arranged to be closed while you're here." The gentleman offered.

"Closed?"

"Yes, the whole mall has been shut down until you complete your shopping."

Holy cow! She knew there would be some little twist, but this was far bigger than she imagined. How do you even go about making that happen? She giggled as they made their way to the fanciest store.

The staff stood at full attention as she walked through the doors. "Good day, ma'am. I'm the store manager. Please don't hesitate to call on my staff if you need anything at all."

As he was greeting her, another gentleman walked up holding a tray with a glass of Champagne. Heather took the glass and nodded to both of them before perusing the store. She felt like royalty, she could hardly believe this level of treatment she was receiving.

After picking out several outfits and dresses, she made her way to the changing room. A gentleman attendant stood outside the room as she undressed and tried on the many different options. Each time she'd open the door and request his opinion, and each time he'd tell her she looked exquisite. It was a bit nice to hear, but not particularly useful for determining which outfits really looked flattering on her. So, she decided to try out a new idea.

"Would you be a dear and come in here for a sec?" She said to the young gentleman as she stood inside the changing room.

"Of course, ma'am. How may I be of service?" He offered politely.

"Close the door." She said plainly, and he complied. "Would you mind unzipping my dress?" Heather said as she turned, presenting her backside to him.

The young man obliged and gently placed a hand on her shoulder, pulling the zipper down exposing more and more of her bare back until it stopped just above her butt.

"Thank you." She said, slipping the dress over her shoulders, down her body and over her hips until she was standing there in only her lacy, green panties. She knew her breasts were mostly hidden from his direct view, but he need only move an inch in either direction to catch their reflection in the mirror. He was beyond polite and looked downward and to the side giving her some privacy.

A sly grin came over her face, and she covered her breasts with her forearms and turned to him. "Would you please hand me that emerald green dress?" She said, shifting her hands so one arm covered her nipples and the other pointed to the dress hanging on the back of the door.

This time he couldn't help but glance at the generous and teasing view she offered before retrieving the dress for her.

"Thank you." She said softly, giving him another playful grin. This was as much a tease for her as it was for him.

She turned her back to him and began to slip on the new dress. As she bent over, her full breasts hung freely with her nipples pointing toward the ground. Even without the reflection, she knew this was slightly visible to him. Not to mention her round cheeks poked out of her now slightly damp panties; it almost felt as if she was mooning him.

Finally, she pulled the dress up, lifted her hair with both arms in the back of her head. "Would you mind?"

He nodded and stepped closer. The zipper on this one fell even lower, and he had to rest his hands on her hips and down to the top of her butt just to get it started. They both acknowledged the touch in different ways. He apologized, and she blushed as he finished pulling up the zipper to her neck.

When he was finished, she let her hair fall and she turned toward him, adjusting her breasts in the fabric. "What do you think?" She asked, realizing her nipples were now even harder and very noticeable through the dress.

"I...I..." he gulped and added "think you look amazing."

It was a different tone than all his previous comments, and she believed his sincerity. "Be honest, do you think I need to wear a bra with this?" She asked, slightly sticking out her chest, giving him permission to look.

"Uhh." He laughed. "I'm not sure what you want me to say."

She smiled and started again, "Let me ask you this. If your wife wore this dress without a bra, how would you feel?"

He blushed. "I'm not married, ma'am, but truthfully I'd be jealous of all the attention she'd get in it. Every guy would be staring all night long."

She giggled and almost gave up her calm demeanor. "Perfect. I'll take it."

"Excellent choice. I'll have it wrapped and waiting for you. What about the other items?"