Five thirty already. Jessica looked at the clock and sighed. Days working in the main corporate office were so jam-packed that time got away from her. But least she didn’t have to make the long drive home tonight. She’d be back in tomorrow morning, and there was a soft, king-size bed with extra pillows waiting for her a few short minutes away. A quiet evening to unwind sounded heavenly, though she’d miss having Eric there to share her bed.
Jess carefully packed up her laptop and loaded it into her bag. As she put on her coat, she glanced around the office. It looked like almost everyone had gone home for the night, doors closed and lights out. But near the exit, she noticed one light still on: Ben’s office.
Involuntarily, Jess reached up to tuck a stray lock of red hair behind her ear. She caught herself wondering if her lipstick had survived the afternoon, wetting her lips with her tongue.
“Oh, come on!” she chided herself as she walked toward the door. “High school was a long time ago, quit acting like a hormone-possessed teenager.” She fiddled with her car keys, trying to ignore the slight increase in her heart rate. Jessica did quite well suppressing inappropriate thoughts about Ben during the work day, but apparently her mental filter had clocked out for the night.
Jessica knew that Eric would find her current struggle for self-control hilarious. When she’d first confessed to having an office crush, she expected him to be jealous. She thought that telling him would help her put those thoughts out of her head. Instead, he’d been turned on at the thought of Jess seducing her colleague. That had added fuel to the fire rather than dampening it.
As she approached Ben’s doorway, Jess took a deep breath. She’d just stop to say a quick goodbye. After all, it would be rude to walk right by his door without acknowledging him. While they had never socialized outside the office, he was one of the rare co-workers she could always count on for support. She had also learned through the years that he had a wicked sense of humor, and could be trusted not to share things said in confidence.
“Hey,” she said, putting a great deal of effort into seeming nonchalant, “I’m heading out.” Jess smiled, in what she hoped was a friendly but not overly friendly way.
Ben looked up from his monitor at the sound of her voice, and smiled back. Despite being older than Jess by a decade or so, he had a boyish grin. “Hey, Jess. You going home tonight, or staying over?”
“Staying,” she replied. “Got a few more loose ends to tie up here tomorrow.”
“That’s probably for the best, traffic’s pretty bad right now.”
Jess knew this was the point in the conversation where she ought to say a final farewell and be on her way, but the warmth of Ben’s smile was so much more appealing than the freezing weather outside. Why not enjoy a little chat as a reward for a hard day’s work?
“That was a pretty crazy meeting this morning,” Jess remarked, stepping through the doorway to enter Ben’s office.
Ben shook his head. “I feel like I always end up being a dickhead when things get off track.”
“Not at all!” Jess sympathized, “You’ve got a lot of pressure managing this project.”
Jess and Ben made small talk, reviewing the day’s events and indulging in a little office gossip. Jess enjoyed the opportunity to make Ben laugh, he was usually so reserved during the work day. She couldn’t help wondering what he might be like outside the office, without those pesky work clothes on…
Jess felt her cheeks getting warm, and steered her wayward mind back to the topic at hand. “There’s just so much going on lately, I can barely keep my head above water,” Jess sighed. Then, before she could stop herself, she blurted out “I could really use a drink tonight!”
“That’s a good idea,” Ben replied. “There’s a nice bar at the hotel, isn’t there?”
Jess felt a little disappointed that he didn’t express any interest in joining her. And yet, he hadn’t said he wasn’t interested either. Something about the way he looked at her made Jess think that Ben might be as curious about her as she was about him. Maybe it was wishful thinking, but…
“Oh yeah,” she said, in a carefully casual tone. “I’d feel kind of pathetic drinking by myself though.”
“I get that,” said Ben, nodding. Then, a millisecond before Jess abandoned hope, he added “I’ve got a few things I need to wrap up, but I could meet you there in half an hour or so.”
“That would be cool,” Jess answered. “I’ll go check in and get settled.”
“I’ll text you when I get over there.”
“Great,” said Jess, “See you then.”
* * *
As she crossed the parking lot to her car, Jess barely noticed the cold. The drive to the hotel was a blur. Checking in, she fumbled with her wallet and dropped her credit card. Upon entering her room, Jess hastily opened her suitcase, grabbing her makeup bag and hair brush for a quick touch up.
Twenty-seven minutes after leaving the office, Jess paced around her hotel room, anxiously awaiting Ben’s text. She kept telling herself it was just a friendly meet up for drinks, that there was no reason her stomach should feel as though it contained a swarm of hyperactive butterflies. But logic did absolutely no good, her mind kept leaping back to the possible results of mixing alcohol, an attractive co-worker and a convenient hotel room.
Jess eyed her bag of sex toys, debating whether she could squeeze in a quick orgasm without undoing her hair and makeup efforts when her phone buzzed.
“I’m in the bar, come on down when you’re ready,” the text read.
After waiting a minute to avoid seeming too enthusiastic, Jess texted back that she was on her way. Leaving the room, she stopped for a last glance at the mirror. Looking herself in the eye, she gave herself a few words of advice.
“Settle down. You are not going to go down there and fall all over yourself flirting with this guy. The secret fantasy is fine, but it would be a horribly awkward day at the office tomorrow if you get carried away. Go, enjoy his company, and your toys will be waiting for you when you get back.”
* * *
Walking into the bar, Jess looked around for Ben. She spotted him quickly: a tall, dark haired man sitting at a table by himself, sipping what Jess guessed was a vodka gimlet. Ben caught sight of her a second later and waved. After a quick visit to the bartender for a glass of wine, she sat down across from him.
“Thanks for coming out to meet me,” she said.
“My pleasure,” he replied. “What are you drinking?”
“Cabernet, my usual,” she answered.
“I thought you might be in the mood for something stronger after such a long day.”
“The thought did cross my mind,” she admitted. “But that could be dangerous.”
“Aw, come on,” he teased. “Living dangerously can be fun.”
“I’ll start slow… plenty of time to overdo it later,” she answered playfully.
“Alright then, we’ll see what happens after your warm up drink.”
And what, exactly, are you hoping to see? Jess studied Ben for a moment over the rim of her wine glass, trying to decide if he was being flirtatious or just friendly. But before she could ponder for too long, he struck up a completely ordinary discussion about work. Must have been my imagination, she decided.
As usual, the conversation between Jess and Ben flowed easily. Before she knew it, half an hour had passed and her glass was empty. Ben promptly brought her a second glass of cabernet. Jess felt happy and relaxed, and let herself lapse into imitations of certain irritating coworkers as they chatted. Ben laughed and egged her on. Despite her best intentions not to be a flirt, Jess found herself involuntarily leaning toward Ben and “accidentally” brushing her knee against his under the table. Ben didn’t seem to be bothered by any of this, though she couldn’t tell if he was enjoying it or simply hadn’t noticed. Either way, Jess figured, it was harmless fun.
“Your glass is empty again.” Ben remarked.
“An astute observation, sir.”
“Are you ready to move on to something else?”
Something about Ben’s tone made Jess doubt that he was talking about a stronger drink. “I think I might be,” Jess responded, leaving her answer as tantalizingly vague as his question.
Ben seemed to find this amusing. “And what would you like?”
You, naked in my hotel room, Jess thought. But what she said was “How about one of those?” while pointing at his glass. She wasn’t sure if she was proud of her self-control or annoyed by it.
“As you wish,” he answered, heading off to the bar again.
Ben returned to the table, this time with two gimlets. Jess was already feeling giddy from the wine, and she knew that vodka was probably a bad idea. But at that moment, bad ideas were sounding like a lot of fun. He set the drink in front of her.
“Why, thank you!” she said with a grin. She took a generous sip.
“I take it you’re all warmed up now?” Ben asked, a glint of mischief in his eyes.
“Most definitely!” Jess giggled.
The conversation now moved completely away from work, the humor crossing lines that neither of them would have gone near at the office. About halfway through the third drink, Jess stopped analyzing Ben’s expressions and comments. She was having fun, a rare moment of complete relaxation without a care in the world. At least until her glass turned up empty again. She looked over and saw that Ben had just finished his drink as well.
“What would you like now?” he asked. His voice was quiet and serious. This time, Jess was certain that he wasn’t referring to drinks.
“I think I’d like to head up to my room,” she said, smiling and meeting his inquisitive gaze. But she made no move to leave the table.
Ben studied her expression for moment. Jess realized that he was trying to decode her signals, apparently she hadn’t been clear enough. “Will you walk with me?” she asked, very intentionally rubbing her leg against his under the table.
That seemed to do the trick. Ben’s impish grin returned as he answered “Of course, if that’s what you want.” Together, they rose from the table and left the bar.
As they crossed the lobby, Jess felt her heart pounding. Neither of them spoke on the elevator ride, anticipation left Jess completely tongue-tied. Then the elevator stopped at the third floor. Ben walked just behind Jessica until they reached her room. She unlocked the door, opened it, then looked back at him.
“How far do you want me to go?” Ben asked. He was giving her one last chance to keep pretending that the looks and comments meant nothing, to draw the line, to call it all off before things went too far. She knew, instinctively, that if she said good night to him here, he would understand. Things would go on as they always had.
“All the way,” Jess replied, with a devilish grin of her own. Then she stepped inside the room, holding the door for Ben to enter.
The click of the door closing behind them dispelled the last of the restraint between them. Just a few steps into the room, Ben pulled Jess into his arms. This time, when their eyes met, she had no doubt in her mind what he wanted. She leaned in to kiss him and felt shiver run down her spine as their lips met. She’d forgotten how exciting it could be to kiss someone for the first time, to get the first taste of a new lover. He was a good kisser too, passionate but not rough. The way he lightly, teasingly used his tongue and gently nibbled at her lower lip made Jess gasp and pull him closer. When they finally broke the embrace, Jess whispered “Do you know how long I’ve wanted to do that?”
“Do you know how long I’ve wished you would?” he answered, smiling. “Never thought you’d go for an old geezer like me.”
Jess chuckled at Ben’s self-deprecation. Older he might be, but Ben was far from geezer territory. With his strong arms and broad shoulders, Jess thought he put quite a few younger men to shame.
“I don’t mind your age. After all, everything seems to be in working order…” As she spoke, she gently pressed her hip against the bulge that had appeared at the front of his khakis.
Ben cut her off with another kiss. Now his hands slid down to her hips, pulling her close against him. Jess slowly rocked her hips, teasing him and feeling her own desire build. Then his grip loosened as his hands slid to her back to unzip her skirt. It dropped to the floor, Jess stepped back to avoid getting her feet tangled in it. While temporarily disentangled from Ben, she took a moment to lift her silky purple blouse over her head and toss it over the nearby desk chair.
Jess now stood before Ben wearing black lace bra and panties, thigh high stockings and high heels. “Keep going…” said Ben, his voice a low, lustful growl.
“Not yet,” Jess shook her head. “Your turn first…” She walked back to Ben, kissing him as she unbuttoned his shirt. Once that was out of the way, she set to work on his belt. She was somewhat distracted by Ben’s hands wandering over her body, squeezing a breast, caressing her back…
“Hey!” she cried, as she felt the clasp of her bra come undone.
“Oops, my hand must have slipped.” He almost managed not to laugh.
Jess slipped her bra off and placed it on the desk chair with her blouse. “I said it was your turn…” she sighed, approaching him to finish what she had started. To her surprise, he put his hands on her shoulders and gently but firmly pushed her back onto the bed. The unexpected move, combined with alcohol and high heels, toppled her easily. She landed soundly on her ass, breasts bouncing with the impact. Ben, normally so reserved, smugly took in the view. She hadn’t expected this kind of play from him. Jess was astonished… and very turned on.
“I’m just going to get right up and get back to taking those pants off,” she taunted, testing him.
The second she had planted her feet to rise, he pounced, pinning her flat on her back on the bed. His hands on her shoulders, his lips brushing her ear, he whispered “No, you’re going to be a good girl and stay right here.” He kissed his way along her neck, down her chest, pausing when his lips and tongue found her nipple. Jess writhed beneath him and pulled him closer.
Ben released her shoulders. Physical restraint was no longer needed to keep her where he wanted her. It also freed his hands to massage her breasts as he nibbled, licked and sucked. Jess was too blissfully lost in those sensations to attempt an escape.
“Now,” he said, “let’s see about getting the rest of those clothes off. Stay right there.”
This time she obeyed, keeping her eyes locked with his as he stood up and stepped back. He reached between her open legs, rubbing her pussy through the thin fabric of her panties.
“These are soaked through,” he observed. “Definitely time to take them off.”
Jess slipped out of her shoes and pulled her feet up onto the bed, lifting her backside so Ben could remove her underwear. Next, Ben slowly peeled away her stockings, leaving her completely naked. He bent down to kiss her neck again, gently stroking her inner thigh as he did. Each time, he stopped just shy of touching her pussy. He seemed to take pleasure in her attempts at wriggling and shifting to remedy that.
Jess decided to try a different tactic. “It seems a little unfair, me like this and you still mostly dressed. Am I allowed to do something about that?”
Ben traced a lazy spiral along her leg with one finger as he rose. Jess sat up and reached for his belt buckle, but he took a step backward and shook his head. “On your knees,” he said.
Jess didn’t hesitate to comply. Kneeling in front of Ben, she quickly unbuckled his belt. She rubbed his cock through the fabric of his pants, heard him gasp and felt his hands entwine themselves in her hair. His button and zipper were undone in a heartbeat, allowing his pants to fall to the floor. She ran a finger teasingly along the waistband of his boxers before sliding them down as well.
Jessica leaned forward and kissed her way up his shaft. She flicked her tongue lightly over the head of his cock before licking her lips and taking him in her mouth. She lowered her head, taking him as deeply as she could. Ben let out a low moan. She slid her wet lips up and down his cock, then stopped to lick and tease before starting to suck again. She felt Ben’s grip on her hair tighten, heard his breathing getting faster.
“Stop,” he gasped. Jess raised her head and looked at him, awaiting his next request.
Ben helped her to her feet. “Turn around and lean over on the bed” he said, guiding her into position.
Jess bent down, resting her chest and elbows on the bed, ass in the air. She could hear Ben tossing aside the remainder of his clothing, and she waited breathlessly for his touch. Though she could easily have turned to see what he planned to do, she preferred the element of surprise. She felt one hand come to rest on her backside while the other slipped between her legs. Jess moaned when his fingers found her clit. At first, he barely brushed it with the softest of touches. As he felt her getting wetter, he stroked more intensely, rhythmically. Within a few short minutes, her body tensed, her legs trembled as she teetered on the edge of an orgasm.
Ben slowed down, easing the pressure on her clit ever so slightly. “What do you want now?” he asked.
“I want you to fuck me.” No playing more games, only the raw, honest truth.
Ben’s hand pulled away, and in its place she felt the heat of his cock against her. “Tell me again,” he said.
“Fuck me now!” Jess exclaimed.
His first thrust was gentle but deep. Jess leaned back, swiveling her hips and grinding against him.
“Is this what you wanted?” he asked.
“Oh yes…” Jess whispered.
Ben gripped her shoulders as he pumped in and out of her dripping wet pussy. Jess arched her back and spread her legs to take as much of his cock as possible. She wanted him deeper, harder, she couldn’t get enough. Jess could feel the bed shake beneath her each time their bodies came together and still she wanted more.
“Ahh…give it to me!” Jess barely recognized her own voice as she urged Ben on. His hands moved from her shoulders to her hips, pulling her to meet each thrust. Jess reached down to massage her clit. Caught in a relentless current of pleasure, Jess felt her mind go hazy. Her breath quickened to short gasps. As the tidal wave of ecstasy crashed over her, Jess let out a primal cry. Ben held her tight, burying his cock inside her as she came. She felt her body shudder, her muscles pulsing, a release of the tension that had been building for so long.
When her tremors subsided, Jess’s legs felt weak and wobbly. Sensing her unsteadiness, Ben guided her to the bed. Jess sat down, then reclined onto the fluffy pillows with her legs parted.
“Aren’t you coming too?” she asked, with a lustful look in her green eyes.
Ben smirked at the double entendre. “Didn’t want to do it too soon,” he replied as he joined her on the bed.
He positioned himself over her, rubbing his cock against the slick lips of her pussy before entering her again. Jess wrapped her arms around Ben, rocking her hips in rhythm with his thrusts. She loved being able to see his face, watching his reactions to her movements.
Jess could tell he was getting close to the edge but holding himself back, she could feel her own pleasure building again too. She opened her legs further and bent her knees to take him deeper. “Come on,” she purred, “I want it all, Ben…fuck me like you mean it.”
Her words had the intended effect. Ben drove his cock into her without restraint now, their bodies colliding hard and fast. Jess dug her nails into Ben’s back as she came, then felt him tighten and throb as he exploded inside her.
When the world came back into focus, Ben and Jess lay together, tangled, sweaty and satisfied. Jess couldn’t quite believe that this crazy night had actually happened. She looked over at Ben lying next to her and smiled.
“Tonight was amazing,” she said. “I think I need to come by the office more often…”
“Seeing more of you would be nice,” Ben agreed. “But who said tonight is over?”