Dildo for the Holidays

This is an entry into

Literotica Winter Holidays Story contest

. Your warning, this is long. But hopefully you find it delightful. And, in the spirit of the season, if the story is enjoyable for you, kindly take a moment to leave a tip (ie. a vote) at the end of the story.

And yes, the town actually exists.

December 20

Emma stared at her computer screen, willing it to tell her if she missed anything in her report when the Worst Human Being in Toronto swung by her cubicle.

It was 9:30 on a Friday night. She was still at work, which was pretty common for her. But surely he should be off dosing women's drinks or something by now.

"I don't know why you're wasting your time. You won't get it, y'know," Mark said.

From the outside, Emma's face remained impassive. It's how you responded to Mark, an emotional vampire who fed on any sign that he was provoking a reaction with you. Admiration and adulation were his preferred meals, but annoying a woman who resisted his 'charms' would also do in a pinch.

In her mind, the drop menu for "Mark Responses" clicked open. There was

- Ignore and hope he dies (goes away).

- Sigh.

- Exasperated Sigh.

- "Fuck off and die, you tiny dick nepo baby" (reserved for her last day at work).

And then, a new item flashed up on her drop menu. She shouldn't, but it was a few days until Christmas; why not treat herself?

Emma made a show of looking at the clock on the wall behind her cubicle and then looked at Mark impassively.

"Aren't you going to be late for your mandatory sexual harassment training?"

Mark's face scrunched up in a scowl, and it was as if Santa swung by the office and gave her an early Christmas gift.

Mark glanced around to see who might be within earshot. Emma recognized the gesture all too well. Unfortunately for Mark, even though it was late on a Friday evening, there were still too many people in the vast forest of office cubicles to let loose.

Instead, he scowled under his breath. "I'm really looking forward to having you work underneath me."

This. This is what played for clever banter with the man. She was already bored with him and resumed working on her computer. She had to finish this report before she left for the day. Hell, for the holidays, she reminded herself.

The problem with Mark Latner - and there were a sizable number of them - but the main problem with him was that his family was rich. He had

just

enough charm, looks, and connections to navigate life and work with minimum effort. If there was a picture in the dictionary next to the definition of Privileged Rich Asshole, Mark's face stood a good chance of being there. Smirking.

He also wasn't entirely wrong. Emma was a Senior Financial Analyst at a major bank. Three years after her MBA, so it was solid progress. But Mark had been here for four years. The fact management hadn't promoted him already showed how much he didn't work and coasted on his family name. However, the consensus was they had to promote him now. But she wanted the director gig because it was the next step. She wanted it so she could stop working 16 hours a day. But mostly, she wanted it so she wouldn't have to call this asshole her boss.

"They're called interviews for a reason, Mark. We'll see what happens after the holidays," she said, not looking up from her screen.

He knocked his fist on the top of her cubicle and laughed.

"You keep right on believing that's how the world works, Ems," he said. "I'm sure you'll spend the holidays studying up in futility. The family and I are off to St. Lucia. Try to stay warm."

Tragically, Mark did not explode on his way to the elevator. Nor did the cable snap, sending him 25 stories to his doom. Once again, Emma reflected on what an unjust world it was.

She sighed, stood up and stretched. She stared around the floor. It was as if the bank had hired Scrooge as a design consultant—row upon row of cubicles. There were a few hints of personality, which were not discouraged so much as viewed as a sign of weakness. After all, if you had time to have pictures of friends and family, that meant less time spent at work, crunching numbers and finding ways to make the bank money, and eventually bonuses for yourself.

There were some half-hearted decorations scattered throughout. Scrooge might humbug it, but they somehow made things worse. A reminder to everyone on the floor that they were all missing holiday cheer by being at work. And in the corner, by the exit, was the world's saddest fake tree. If there was a tree designed to remove the Christmas spirit, it would be this one.

Depressed, she flopped back into her chair and spent another hour staring at the report. She was just being stupid now. She would delete a comma and then add it again. It was idiocy. No, worse, it was a denial of reality. She hoped she would fall asleep on the keyboard if she did this long enough. It had happened before. She woke up at 3 a.m. with keyboard imprints on her face. She staggered home, showered, passed out for a couple of hours and then returned to work the following day at 7:30.

What she was trying to do tonight was different. She was trying to avoid reality by working herself unconscious. Then she'd miss the flight she dreaded having to take tomorrow morning.

What she should do is go home, pack, and try to get some sleep. But that wouldn't work. She needed something else to distract her. She had two potential candidates for distraction. One was driving her to the airport tomorrow morning and wouldn't take kindly to her calling and whining that she needed sex. Fortunately, the second option would be thrilled to serve as a distraction. She took out her phone.

"Where are you?" she texted.

The response was quick. Emma hit save on the document and sent her boss a link to it on the server with a brief message wishing him a happy holiday. It was a sincere wish and a reminder that she would be off until early January. She didn't think he would forget, but it was also entirely possible he would wander around the office on Monday looking for her.

She threw on a coat and headed off in search of Terrell Lynch.

***

The George looked like any one of the hundreds, probably thousands, of Irish-style pubs that populated metro Toronto. Irish beer on tap, dark corner booths mixed with an assortment of tables, sports on the TV, and different soccer banners hung behind the bar. The first clue that something might be gay about the place, aside from having to walk down Church Street in the heart of the city's gay district, was the Pride Flag hanging behind the bar. The fact that the clientele were almost all men wouldn't necessarily be a tip-off. But that they were generally better dressed than the crowd you might find at a standard pub would be suspicious.

A couple of guys making out in the corner booth sealed the deal.

It had been a couple of months since she wandered into The George. Their current decorating consisted of lobbying a grenade full of tinsel into the middle of the pub and then standing back as it exploded. There was also a Christmas tree about twice the size as the one in her office and about a tenth as depressing. It was night and day from where she had been 30 minutes ago.

She could never get a straight answer out of Terrell on why, of all the gay bars in the area, he settled on an Irish one.

"Guess it must be my Irish blood," he said, flashing the smile that got him his latest TV acting gig.

It was also the smile that got him into the pants of any number of men and women. During her more cynical moments, Emma suspected that being black in a predominantly white bar made him stand out. And Terrell never liked blending into a crowd. Not that he needed to worry. He was a little over 6 feet tall, slim, and well-dressed in clothing that showed that he worked out. Oh, and he was drop-dead gorgeous.

They met a little over a year ago. One of Emma's few female co-workers pleaded with her to leave early on a Friday night. She'd been invited to a party promoting a new TV show and her friend had bailed. Emma went, mainly for the free food and booze. She had just broken up with her girlfriend because Emma was 'never around for her.' She was not in the mood for another clingy partner.

As was usually the case, Terrell was the centre of attention, all gorgeousness and charm. Emma didn't spend one second trying to catch his attention. She was never one to try to snare guys. She knew she was good-looking. Whatever genetics her family brought with them from Ireland to Canada had been kind to her.

But she wasn't looking to do damage that night. Food and booze. That was it. She had to get back into the office in the morning, and crunching numbers with a raging hangover sucked. So when she turned around, she was surprised to see him there, flashing a panty-soaking smile at her.

They chatted, and at first, it was so she could enjoy the 'who the fuck is she?' looks from the other people at the party. To her surprise, she caught herself flirting back at him. To her bigger surprise, she was energetically fucking him at her condo a few hours later. To her utter astonishment, he texted a couple of days after that. They'd been a thing ever since. Maybe it was that she wasn't out to tie him down. Perhaps it was because, in private, he could get overwhelmed with the business side of being an actor. She had a pretty good head for those sorts of things.

Or maybe she just appealed to the Irish in him.

She walked towards Terrell's table, drawing a few looks. She'd like to think it was because she was cute and managed to find a way to make her work outfit for the day - a blazer, white top and black pants - into something a little sexier by undoing a few buttons on her top, and slipping on some four-inch heels. But by her count, three other women were in the bar, so she knew why they were looking.

A small gathering of friends and other men hung around as he held court and ate chicken wings. Several of them noticed her and looked annoyed. Emma could understand. Most of the men in the bar wanted to know how she ended up with him.

She walked up behind him and tapped him on the shoulder. He turned and smiled at her, which would have gotten her wet in almost any circumstance, but he had sauce on his lips from the wings he was eating. She leaned in and kissed him, as much for the affection as to get a taste of the sauce.

She caught a few disdainful looks out of the corner of her eye, but whether it was for the PDA or kissing someone with sauce on his lips, she couldn't say.

"Hey, baby," he said. "You're off work early."

"It was that or commit murder, so I felt leaving would be best," Emma said, sliding into a chair across from him. She looked covetously at his wings, as she hadn't eaten anything since a salad around 12:30. He shook his head in mock disappointment, then waved a hand at the stack of wings before him. Her bad habit of forgetting to eat was well known, so she wasn't surprised he ordered food for her.

"I can imagine, he said. "Although I figured you might take the opportunity to go home and pack or something. You're flying out early tomorrow," he said.

"Mmmf, don't remind me," she said, making quick work of a wing. She was so hungry she didn't even try to make a sexual show with it.

"I've never understood why you're so reluctant to go home and see your family. I'd think Christmas back in Newfoundland would be lovely. Green's Harbour, right?" he said.

She almost choked on one of the wings, which he fortunately misinterpreted as her inhaling too much food at once. Once she regained her breath, she muttered, "It's family. It's complicated."

"Mmm," he said, not entirely believing her. He was about to say more when one of the guys around the table spoke up.

"So if you have an early flight tomorrow, I guess you'll have to go home and pack soon. We were all going dancing shortly," he said. He looked about 21 and was very pretty. Suspiciously well-tanned for Toronto in December, he'd created something magnificently complicated with his hair so that it stood about 6 inches off the top of his scalp. And a shirt that showed off a healthy amount of chest.

Emma smiled at him, and she could see Terrell silently willing her not to destroy him.

"Well, I don't really sleep."

"Really?" he said.

"Yes, I just bathe in the blood of virgins every Friday night and it keeps me revitalized," Emma said, leaning across the table. She grinned predatorily at him and did something with a chicken wing that made him flinch. He was about to protest when Terrell stepped in.

"Did you want to join us?"

One of the things about Terrell was that he was consistently nice. Looking the way he did and being able to pour on the charm the way he could, there was a high risk of him being a massive asshole. But thanks to years of business school and working a high-pressure job at a bank, Emma had an asshole detector second to none. There was no shortage of alarm bells going off as she looked around the table. But there sat Terrell, smiling, calm and not an asshole, right in the middle of the storm.

What she was about to do was asshole behaviour, if she was being honest with herself. They had all made plans and she was swooping in to shatter them because she was in a pissy mood because of work and having to fly tomorrow. Then again, when she was helping Terrell with some of his budgeting a few months ago, she noticed a couple of the men at the table had fleeced him for expensive wardrobe upgrades. He didn't see it that way, of course. He was doing ok with his TV show, so why shouldn't he help out a few friends in need?

She suggested that if they needed new clothes, they might not need TOF Paris apparel. They could try Old Navy next time. He shrugged his shoulders but said he'd try not to buy so many gifts for friends.

Anyway, she and guilt were old friends. You don't go as long as she did without going back to Newfoundland or seeing her mother without having ways to process massive amounts of guilt.

"I mean, yes, I could join you dancing. Or," Emma said, finishing off a wing and pausing for dramatic effect, "my boyfriend could come back with me to my condo for sex, seeing as how he won't be seeing his girlfriend until New Year's Eve."

She threw in the "big eyes" to seal the deal, which was a bit like using a nuke on an ant hill, but why take chances?

There was a collective groan from the men around the table as they knew they had lost. Terrell looked at her and shook his head.

"You don't play fair," he said, standing up and taking his coat from the back of his chair.

"I'm a banker bitch," she said, reusing one of the phrases one of the men at the table had used to describe her when he thought she wasn't listening. "And I'm horny. What's fair got to do with it?"

She grabbed a wing as she stood up from the table and grabbed Terrell's hand as they walked out of the bar. She didn't need to look behind to see the death glares.

***

"You're being a tease," Terrell groaned.

"You like that though, baby," Emma said, grinning as she slowly rode his cock and ran her nails down the muscles of his chest. Terrell had, in her experience, one of the best cocks she'd ever had the pleasure of fucking. It was seven inches of very nice, thick cock. She remembered before she saw him naked for the first time that he was so perfect that she fully expected his cock to be a disappointment. But once he dropped his pants, there it was, a perfectly lovely hard cock. One that hit all the right spots when inside her.

She told him once that it was a Goldilocks cock, and he never knew how to respond to that. Which is fair enough.

And right now, she was determined to find every single one of those magic spots in her pussy. So she ground on Terrell for a while, then bounced energetically on his cock for a few minutes until she got tired. Then she would lean over him, draping her tits over his mouth for him to suck. Then, once she got her second wind, she'd begin bouncing on him again, starting the whole process over again.

So far, it had been good for three excellent orgasms, and judging by the amount of sweat collected on both of them, a couple of hundred calories worth of cardio.

He was right though; she was being a tease. Because she liked teasing Terrell. Because she also knew his secret. He could only cum when she was sucking his cock or when he was fucking her from behind.

It didn't require a degree in psychiatry to figure out why that might be the case. Some women might take offence. That he might be fantasizing about someone else while they had sex. And yeah, when the thought occurred to her, she was briefly annoyed by the fact. Then she considered how many boyfriends she had in the past with a quick trigger and turned it into her advantage.

He was also reluctant to go down on her. Again, a bit of a tell. But that's okay, she had someone else to take care of that. And in any case, he felt so guilty that he had no problem being teased like this for a solid half hour or more before he started to whine about it.

"Poor baby," she said and reached behind her. She felt his balls and he groaned again. Judging by how they felt, Emma would have quite a mess to clean up afterwards. Ah well, he'd been a good boy so far. She was feeling much less stressed. She tried standing up only to discover her legs were not working right. Grinning, she pushed up from his chest, and flopped over onto the side of the bed. She then placed her head down on a pillow and lifted her ass in the air.

It was inelegant, but got the point across. And given that Emma had spent the last half hour teasing him, she knew what she was in for. Terrell didn't disappoint, getting behind her, lining up his cock with her pussy, and pushing in with one, elegant, forceful stroke.

"Oh Fuck!" she cried out.

The next few moments consisted of him grunting behind her as she cried out. His hips slapping into her ass. Emma loved that slapping sound, but she was a little more focused on what was inside her now, than auditory stimulation.

"Bet you regret teasing me now," he said, and a particularly aggressive bit of thrusting that made her cry out. She could feel another orgasm building, and it was probably going to be the evening's finale. She looked back at him, flicked some sweat-soaked hair out of the way, and grinned at him.

"Why, baby? I tease you and then get pounded. Sounds like win-win to me," she said, and wiggled her ass at him. "Why don't you

really

punish me if you're mad."

That's all it took. Terrell slapped her ass, about as aggressive as he ever got, and she yelped. Then he grabbed her hips and began pounding her. Her hips bounced into the bed. Any idea of fucking him back was gone. She was just along for the ride.

Emma was almost always in control when they fucked. Even his losing control like this was partly by her design. But finally, her brain shut down completely. No more thoughts of idiot coworkers, stressful trips, or if she was too manipulative. Suddenly, it was just a blissful, shattering orgasm.

"Oh God!" she cried out into the pillow where she buried her face. Dimly she heard Terrell grunt out, "Fuck!" and then felt a flood of his cum enter her pussy.

Nothing much happened for the next few minutes. Terrell was considerate enough not to collapse on top of her at first, but through her haze she could see his arms start to shake until he eventually slid out and collapsed on the bed next to her. Emma smiled and felt like she was about to pass out when Terrell gave her ass a slap.

It wasn't a hard slap, but it was unusual enough that it snapped her back out of her daze. She flipped her head around to look at him.