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Office Milf [F36/M26] [Business Trip] [Cheating]
Author Summary
louisavampa is in cheating
Post Body

Roseline walked to her hotel room carrying her heels in hand. Her phone buzzed from a text. It was probably from her husband, but thankfully work trips gave an easy excuse to ignore him. She was hoping to make an earlyish night of it, two glasses of wine were plenty for her. The heavy drinking was better suited to the younger folks at the conference, not her. It wasn't that she was ancient, but being a wife and mother in her mid-thirties put her in a different phase of life compared with her subordinates at work. When she turned into the corridor which housed the hotel rooms her company rented, she saw Reese sitting on the ground in front of his door.

"Did you get locked out?" asked Roseline.

"Something like that, but it was my own fault." Answered Reese.

Reese was a popular young employee who seemed motivated to make something of himself. He was a big guy with a friendly personality, making him well liked by his peers. Of the twenty people who reported to Roseline, he always stood out to her as someone who could be relied on.

Roseline, an up-and-coming executive, was extremely sharp and cared dearly for the people who worked for her. Whether it was sending gifts for their birthday or telling her employees they could call it an early day after finishing a hard project, she always found ways to make her people feel acknowledged. Roseline was considered by many to be the office mom, and she was happy to take on the role.

Once she turned thirty, Roseline had gained a few pounds and no longer had the incredibly slender figure she enjoyed through her twenties. She comforted herself with the knowledge that she was at a different point in her life. She was aware that in her younger years, she was considered a knockout, but that kind of attention wasn't something she needed.

Roseline was a mother and married to a loving husband, and there was no reason to miss those years of being a young analyst who was constantly hit on at conferences like this. In reality, she was naive to the current effect she had on men, foolishly believing thicker thighs made her any less desirable. But the changes to her body were not the reason for the diminished attention she received from men. Roseline was still a stunner. The only real difference was her status. She was now considered an expert in her industry, and her position and reputation were the only reasons she was no longer approached in that way.

"So, what happened?" Roseline asked Reese.

"Well, my brother was invited to a wedding in town during the conference and, since I had the room, I told him he could crash with me." Replied Reese.

"So why does that leave you stuck in the hall?"

"Well, he reconnected with an ex at the rehearsal dinner and they're kind of in there now. But it's no big deal. I'm just going to hang out here."

It might be a big deal -- they couldn't have an employee getting kicked out of the hotel for sleeping in the hall. That would reflect poorly on the company at the conference and might be an issue for their invitations in future years.

"Look, you really shouldn't have shared your room without notifying the company, but let's not make a bigger deal about it than we have to. You can sleep on my couch until your room's available." Said Roseline.

"Thanks. That works for me."

It was the type of thing she did. She was the office mom and always wanted to be there for her people. Reese stood up, watching Roseline's hips as she unlocked the door to her room. He was happy for the invitation, but didn't see her as a mom. He saw her as something very different.

The room was nice sized, with a king bed and comfy looking couch. When the door closed, Roseline noticed the awkwardness that came from being alone in a hotel room with a man who wasn't her husband. It was something she hadn't considered in the hallway, and she worried slightly that she had gotten ahead of herself by inviting him in.

"I'm going to get ready first, and then you feel free to use the bathroom. You can sleep on the couch until they are done with... Whatever." Said Roseline.

Reese slid down onto the couch, causing it to creak beneath his large frame. Roseline gathered her pajamas, remembering the hotel robe at the last moment. She would need it for modesty. Once in the bathroom, she quickly changed into her pajamas which consisted of thin cotton shorts and a matching button-up top in blue.

She brushed her teeth and pulled her long dark hair back in a ponytail and picked up the robe. Before putting it on, she looked herself over. Her breasts stood out prominently against the cotton fabric and the shorts were probably a size smaller than she would have liked. It was something she expected her coworker to see when she chose it, but Roseline planned to wear the robe until turning off the lights. Reese wouldn't need to see anything. A couple minutes later, Roseline exited the bathroom wearing the robe.

"It's all yours Reese." She said, sitting on the edge of the bed and checking her email on her phone.

Reese went into the bathroom. In the quietness of the room Roseline could hear it. The unmistakable sound of two people having sex. Reese's brother was clearly giving the woman he was with a memorable time in the room next door. The sounds brought with them a sensual atmosphere, and Roseline started regretting inviting Reese into her room.

She tried to brush the thought away, he had to be ten years younger and was far too handsome to be interested in an older woman. Her consideration of his attractiveness did not help to calm her, and thanks to the rising moans of the woman next door, Roseline was on edge.

When Reese finally came out of the bathroom, Roseline was surprised to see he took off most of his clothes. He wore only a tight- fitting white undershirt and boxers. She didn't react but noticed his penis swinging freely beneath his underwear. She was slightly dumbfounded, watching his crotch. When he sat on the couch, she stood up and took off her robe, forgetting to first turn off the light. She stood there stupidly for a moment, as Reese surveyed her body. The pajamas were thin and thanks to the illicit sounds next door, her erect nipples poked conspicuously against the top. When she finally regained her senses, Roseline dashed for the light switch, unintentionally giving Reese more of a show as her breasts and ass jiggled appealingly with her rushed movements.

Once the room was dark, she shook her head in disappointment. Reese wasn't sure what to think about what he just witnessed. Not only did he get a good look at his boss's fantastic body, but for the first time ever, his boss seemed flustered. He considered the chances her actions were deliberate.

It took Roseline a while to fall asleep. The couple having sex next door were making a lot of sound, and it was very strange having Reese in her room. She had troubled sleep, with weird dreams that were atypical for her.

The toilet flushed -- startling Roseline awake. She was panting and covered in a light perspiration. Lying in her half stupor, she realized Reese must have woken up to use the bathroom. There were no longer sounds coming from the next room, and he was probably getting ready to leave. He opened the door to the bathroom, which partially lit the dark hotel room. Instead of leaving, Reese fell into bed next to Roseline, draping his arm over her. She was startled and should have spoken up but was half asleep. The blanket totally covered her, so they weren't really touching, and it was comforting having his big arm around her. He seemed to be trying to sleep anyway, so she allowed herself to drift off without a complaint.

A little later, she stirred and obliquely noticed that he was under the covers with her, but he was snoring lightly, and she quickly fell back asleep once more.

Later in the night she rolled over to get comfortable and found herself pressed against Reese's side. It felt nice touching his warm body, but she knew she needed to move away from him. As she was about to, he swiftly slid his arm beneath her and pulled her close to him. She was stunned, his arm encircled her shoulders, pressing her soft breasts into the side of his ribcage. It could have been the wine or the fatigue, but she felt nice. Instead of saying something or fighting it, she rested her head on his shoulder. There wasn't anything horrible about what they were doing, and it wasn't like he had that sort of interest in her.

Roseline was comfortable but found it difficult to fall back asleep. She contented herself by listening to him breathe. Her hand rested on his chest, rising and falling with each breath. After a while she moved her hips a little to adjust her legs. Seemingly in response, Reese reached down and grabbed her right leg, pulling it across his body. She gasped, surprised to feel him touch her bare flesh. Incredibly, after he finished repositioning her leg, she could feel that it rested directly against his crotch. His boxers were the only thing separating her from touching his penis. Whatever this was, she knew it had gone too far. Their situation now balanced at the edge of infidelity.

It was so subtle, Reese almost didn't notice, but in a miniscule, almost imperceptible way, Roseline moved her hips. The movement was so minimal that it just barely caused her shin to graze his crotch. He started to caress her hip with the tips of his fingers. By degrees, she was coaxed into action. She slowly stroked him with her leg, feeling his cock harden beneath the boxers. It seemed like some unreal game. This was nothing like her, but she kept going. The movements continued, increasing slowly, incrementally, until she found her leg curled tightly against his body and her calf muscle pressed firmly against his erection.

She considered stopping at this point, but Reese made the next move. He tossed the blanket aside, revealing their position in the dim light. Roseline's leg was essentially bare, her shorts were riding so high that most of her butt cheek was visible. She realized that she was pushing her crotch into his hip, dry humping him, and withdrew herself. The sight of her body lying against his made the situation all too real, and she thought to get up and hide in the bathroom. But before she could, he put his hand around the back of her neck and guided her down.

Roseline knew she could stop Reese. Any single word from her and this all would have ended, but she stayed quiet and let him take control. He pushed her face down until it pressed against the bulge in his shorts. She inhaled him deeply, his heavy odor sending a shudder through her body. Reese pulled down his boxers. The head of his large penis was right in front of her slightly parted lips, her hot breaths pouring down his length. She didn't think she had the will to go through with it, to cheat, but she badly wanted to. He pushed her head lower and Roseline felt gratitude for his decisiveness as she opened her mouth to accept his erection.

Her tongue lapped along the underside of his penis, as she ravenously tasted him. Roseline couldn't fit it all within her mouth and compensated by massaging the bottom of his shaft with her eager hands. Saliva dripped down his dick, lubricating her fingers as she polished it.

"Shit! That feels amazing." Said Reese loudly.

"No, no, no." Whispered Roseline, temporarily broken from her enthrallment. "You need to keep it down. Linda is next door."

The adjacent room not occupied by Reese's brother was taken by Linda. She was another employee of the same company and had worked with Roseline for years. The activities of Reese's brother in the next room made it clear that the walls were not thick enough to grant much privacy as far as sound was concerned. Unfortunately for Roseline, Linda was one of the worst neighbors to have in this situation. Not only was Linda well aware that Roseline was next door, but she was casually acquainted with Roseline's husband.

"I'm happy to finish you off, but you need to keep quiet." Said Roseline in a breathy, intimate voice.

Reese nodded in agreement. Roseline changed her position, getting on her knees, and planted wet kisses on the tip of his dick before beginning to suck him again. She was getting very turned on. Before being jolted back to reality with the reminder of Linda's proximity, Roseline considered that things with Reese might have progressed to something which they could mutually enjoy. But now that the risks of their entanglement were reinforced, Roseline decided the fantasy of them having sex was foolishness. Still, it seemed unfair to kick Reese out of bed. It wasn't a total loss though, giving her subordinate a blow job would still be the wildest thing she'd done in her life.

Roseline bobbed her head up and down on his dick and rubbed it vigorously with her hands. Her soft pale cheeks puckered in as she tried her hardest to please him. She knelt on the bed perpendicularly to Reese. He watched the movement of her breasts as they hung beneath her, reaching out to cup one, but when he touched it, she instantly recoiled away.

"What?" she asked in a quiet voice.

She was genuinely confused why he touched her. In Roseline's mind, she could rationalize why he would want a blow job. They were in bed together and a mouth was a mouth, and she could certainly use hers to make him feel good. But she was still incredulous to the idea that he might be physically attracted to her.

"I want to touch your tits. And see them." He replied, remembering to keep his voice down.

Roseline still couldn't totally believe it, and she was embarrassed to take off her top, but thought he might want to see a pair of breasts to help him finish, and hers would have to do. Apprehensively, she started to unbutton her shirt. While she did this Reese quickly pulled off his t-shirt and boxers. He was in great shape and Roseline felt idiotic, looking at his gorgeous body, as she continued to undo her top.

She popped the last button and hesitated a moment before opening her shirt. Reese couldn't believe how amazing she looked. Roseline was self-conscious that her breasts didn't sit quite as high as they did in her twenties, completely failing to realize what a beauty she was. She tossed the shirt aside, expecting to get back to Reese's blow job, but then he did something else which surprised her.

He pulled her up to him and gave her a lustful kiss. She leaned into the kiss wrapping her arms around him. Roseline could previously never admit it to herself, but she had always found Reese to be very sexy. Even when her lips were wrapped around his cock, she didn't want to get her hopes up about what he might do to her. But now, the direction of things seemed inevitable. He excitedly kissed along her fine neck while teasing her nipples with a free hand. She reached for his penis and held it in her smooth little hand, finally allowing herself to hope she might soon feel it inside of her.

The kisses continued, but now he was trailing down her body kissing her breasts and along her ribcage. When he arrived at her waistband, he stopped.

"Can I take these off?" He asked.

She gave him an uncomfortable look for a moment but relented and nodded her head. It made her nervous because she hadn't trimmed down there in forever and she couldn't imagine him liking what he found. Reese slid her shorts off revealing the full bush.

"That's what you get when you go after a middle-aged woman." she said.

"You are undoubtably the sexiest woman I have ever been with." He responded.

Reese's words shut her up and caused her to blush. He had such an easy sexiness about him. The two of them began to kiss again, his erect penis now grinded against her pubes. She massaged its head with her hand.

"Do you want it in my mouth again?" She asked, momentarily breaking from their kiss.

"No." he said.

Roseline knew what was next but was a little reluctant. Her chest heaved and she explored his hard body with her hands.

"Alright, I'm ready." she said.

Reese directed Roseline onto her back and slid on top of her. They kissed again, circling their tongues passionately in one another's mouths. He rubbed the shaft of his penis against the outside of her vagina, stimulating her considerably. Roseline had to pull her lips from his and bite down to stifle a moan.

Propping himself up on one arm, Reese took his penis in hand and positioned it in front of her vagina. As he entered her, Roseline was forced to clap a hand over her mouth to muffle her whimpers. She knew he was significantly bigger than she'd ever experienced, but it still surprised her to be so overwhelmed by his penetration.

"God, it feels good in you. I hope I can hold out long enough for you to come." Said Reese.

She could already tell that wouldn't be a problem. As he found his rhythm, pushing in and out of her, Roseline felt her chest blazing with arousal. When she had sex with her husband, she was always careful to angle herself, so he had a chance to stimulate the most sensitive spots within her. But with Reese, she had the opposite issue. It felt like he was everywhere within, exciting every part of her all at once. He leaned down and started to kiss her neck, not slowing his hips which drove him into her drenched vagina. Her breathing began to quicken.

"Baby! I'm already getting close, but I don't think I can keep quiet." Said Roseline in a defeated voice.

She felt childish, admitting her desperation to this man who now had complete control over her. When her husband was able to make her come, she could easily keep quiet. But when she and her husband had sex, it felt nothing like this. Now, Reese was causing something substantial to build within her, and she knew it was growing beyond her grasp.

"What do you want me to do?" asked Reese, slowing his pace somewhat.

She stared at him with her big brown eyes as she searched for an answer, knowing there was only one.

"Just keep fucking me." she said.

Maybe Linda wouldn't notice, but at this point, Roseline didn't care if she did. Reese continued thrusting, and lowered his head so he could kiss her breasts. She mewed loudly and ran her nails across his strong back. It felt as though this man knew things about her body which were previously secret even to her. Reese was fucking her into oblivion. His large frame and bucking hips pushed her up the bed until she found herself pinned against the headboard. Roseline's body stiffened and her breathing slowed to short trembling gasps. He could tell she was at the absolute edge and kept thrusting as she clamped down firmly around him.

"Oh Reese, fuck!" She screamed remorselessly.

The orgasm submerged Roseline in a turbulent quivering rapture. A life of shallow half-climaxes had not prepared her for the devastating finale she was experiencing. She shuddered violently and strained her face as Reese continued to drive into her. Roseline's orgasming vagina beared down upon his surging dick, and each time he thrust, she moaned vulgarly.

This was her secret dream, the thing she missed out on by compromising and settling down so young. There were dozens, maybe hundreds of men who wanted her, who flirted or propositioned her. She always denied them, but sometimes, many times she wished she hadn't. This time, finally, she relented, giving herself fully to someone outside of her marriage.

Roseline embraced him close to her and rolled her hips enthusiastically, hoping to drink in every drop of enjoyment from the moment. It was the greatest pleasure she had ever felt. It flashed in her mind that she never wanted to have sex with her husband again, but she needed to put that feeble man out of her thoughts. Reese deserved her full attention. Roseline's desire to thank him for this moment was immense and she undulated herself emphatically upon him, hoping to return a portion of the enjoyment she had received. Her orgasm had faded, but she already felt her body mounting towards another.

"I'm about to come." he said.

"Good, I want you to. I'm all yours." she said in a low seductive voice.

"Oh, Fuck!"

He made the choice she'd hoped for, keeping himself fully inside of her as he came. It was the first time in her life that Roseline could feel a rush of semen as it filled her. She clamped down on him again and orgasmed hard for the second time. Roseline kissed and nibbled Reese along the neck and ear as she shivered in satisfaction. He stayed inside her for a long time after.

She lay next to him, fully exposed, as he idly grazed the tips of his fingers along her breasts. In a way that was wholly new to her, Roseline felt satisfied.

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