[F] [Cheating] [1st Post, Be Gentle!] Encounters

“ What the FUCK am I doing?”, Lily thought, as she lathered up in the shower before work.

For the past several months, Lily found herself in a situation that she never thought she would allow herself to be in, cheating on her husband with a married coworker. Her marriage to Peter had devolved into more of a business relationship, and had been pretty dead sexually for quite a while now. Even so, she NEVER thought that she would do something like this, let alone for this long. She was pretty, with long dark hair and a naturally slim figure that she worked hard to keep that way. She didn’t have a huge chest, but the size of her C/D cup breasts was in perfect proportion with her small waist and wider hips. She attracted a lot of attention from men, but truly never felt the desire to act on it.

Lily worked as an office manager, in a building that was undergoing a lot of construction and renovations. She had her own office with quite a bit of privacy, so she pretty much kept to herself. She was an introvert by nature. Bill was the owner of the company doing construction on the building. He was surprisingly young to have his own company, having just turned 30. They interacted frequently, as most of the work being done was in Lily’s section of the office.

In the beginning , Lily barely noticed Bill’s presence. He was cute enough, sure. He was about 6 feet tall, with a sturdy figure, neither skinny or super muscular, but solid and strong. He was a big boy, with wide shoulders, a broad chest, and thick forearms and calves. He was just big, everywhere. Lily was 36, which was close to seven years older than Bill. Because of the age difference, despite his large build, she viewed him as more cute and boyish rather than sexy.

Over the last several months, Lily and Bill developed an unexpected, close friendship. Bill made surprisingly good conversation and talked very openly about his life and marriage, and the problems in both. He seemed to naturally be one of those people that is easy to talk to, and as time went on, Lily began to open up about her own life and marriage. It all started out so innocently, she thought, remembering back to that phase in the beginning when they WERE just friends.

He was no angel, of course, and there were certainly moments where he made little jokes or comments that made it clear to her that he found her attractive. She’d learned he had a “thing” for women in office attire on the sexier side, like tight pencil skirts, heels, etc. While she didn’t dress like this every day, when she did, she could see him checking her out. and he wasn’t exactly trying to hide it. In fact, he’d give her little wide-eyed looks, like a teenaged boy in awe which she found kind of adorable, but also, a surprisingly huge turn on. She hadn’t realized how much she missed that kind of attention.

Long story short, work conversations led to texts, which led to sexts, which led to pictures, which eventually led to this affair that she currently found herself in. She had cried after the first time, overcome with guilt, and not believing that she had allowed things to progress so far. She kept telling herself that she was going to end it, but at the same time, she also found herself wearing outfits she knew were going to drive him wild and loving the reaction when they did. They didn’t have the opportunity to actually fuck very often, but there were frequent” encounters” at the office over the last several months . She frequently revisited these encounters in her mind when she made herself cum.

Before Lily had gone on vacation to Mexico with her husband Peter this past week, she had promised herself that when she returned , she would end it. Well, today was the day, the first day back to work- and while she knew she was doing the right thing, she wasn’t looking forward to it.

“ I’ll wear jeans”, Lily thought, knowing how dresses and skirts not only ramped up his sex drive, but created an “easy-access “situation. She needed SOME way to ramp up her will power, no matter how weak the deterrent.

When she got to her office, she sat at her desk and powered on the computer, and noticed several sticky notes on her desk. As she looked more closely, she realized that each one was a note from Bill telling her how much he missed her every day that she was gone. “That cute little bastard”, she thought, both pleasantly surprised at the gesture and sad about the prospect of ending things, but she knew she had to do it. Just then, her phone dinged and she picked it up to see a message from Bill saying “ I’m downstairs, come here, I’m dying to see you.” A smile spread across Lily’s face. She was just as eager to see him, but she took a moment to mentally recommit to her plan , this couldn’t go on forever.

When she stepped into the basement storage room, Bill was there in usual work attire, a baseball hat and hoodie with his company logo, jeans, and work boots. He unleashed a huge boyish grin when he saw her, and opened his arms to her and she went to him. His hoodie had the familiar smell of the detergent he used and she breathed it in, missing it. He immediately started kissing her urgently, sliding his tongue into her mouth, sucking hers into his. She put both hands on his chest and gently pushed him back, and said , “Wait, can we talk for a minute?”

“Sure” , he said, but continued kissing her while he ran his hands all over her body.

He had HUGE hands. Bear paws, she called them. And she fucking loved the way it felt when he groped and grabbed her like this, as if it he could not physically resist. She couldn’t help but think about how her husband never reacted to her this way anymore. She’d forgotten this feeling. And how intensely good it was.

He had both hands on her ass, grabbing and lifting her ass cheeks up and apart, really squeezing , and slapping it hard as he let go. He groaned in her ear, and she could instantly feel a rush of warmth and wetness building between her legs.

“ No, no, no, this is NOT the plan!”, Lily thought, but did not say. This is what always happened Sometimes, even just the sight of him made her pussy start to throb. It’s like her brain just associated him with sex now, and reacted involuntarily. She didn’t like how out of control this made her feel. A year ago, she would never have believed it if someone told her this is what she’d be doing. Never. Where did her conscience go? Her morals, her willpower? Why was it so difficult to be“ good” now?

She’d been cheated on, she had so many friends who had been too, and knew the destruction that it could wreak on people’s lives. She never understood how people could do such a thing, to someone they loved unless they were just completely selfish assholes, that didn’t care who they hurt. But, she’d truly never intended for this to happen. She never thought they’d be anything more than friends. She hadn’t realized how powerful lust could be, after so long without it. How hard to go back to the life before it.

She closed her eyes while he kissed her neck, and slid his rough, warm, hands down the back of her jeans, and up the front of her shirt, roughly pulling down the front her bra to feel her breasts and play with her nipples. Every now and then he’d bend his hand down to suck one of them into his mouth, rolling his tongue all over it until it was hard, and then giving her erect nipples gentle little bites and kisses. It was almost unbearable. He then unzipped her jeans, and slid one giant hand down the front, easily slipping his fingers between her warm, now soaked, pussy lips, and sliding one, then another inside of her. Now it was her turn to moan in his ear.

“Fuccccckkk”, Bill whispered, “You are SO fucking wet.” And she was. She was almost embarrassed by how wet she always got with him, because no matter what she said, or what her intentions were, her body always gave her away.

She was standing in between his legs in front him, where he sat on the desk and she could feel his dick was now rock hard against her. She looked down at the outline of it in his jeans, and rubbed and squeezed it with her hand over them while he worked his fingers inside her, stretching her, and feeling for that soft spot that he knew always made her cum.

She unzipped his jeans , and gripped him in her warm hand, feeling how big he was, how hard, and she rubbed the little drop of precum she felt on the tip around the large , bulging head of it, aching to feel it inside of her. At this point, he had wriggled her jeans down around her thighs and was roughly fingering her, while she played with his cock. You could HEAR how drenched she was, as his fingers furiously pumped in and out of her, making audible squishing sounds with her juiciness. She moaned and leaned against him, overcome with how fucking good his fingers felt stretching her inside, and pumping against that sensitive spot inside, that he always found so easily. Eventually, he slid them out of her, and looked right into her eyes, as he put them into his mouth and sucked her taste off of them.

“Holy shit”, Lily thought, as she felt the last of her will power slipping away.

Neither of them felt very comfortable fucking at work, given their situations, and the risks involved. But that didn’t mean she couldn’t play a little more, so she could finally cum and think clearly again. She grabbed Bill by the hand, and led him around the desk to the old desk chair, and sat him down, with his rock hard cock exposed. She turned around facing her back to him and shimmied her jeans and panties down a little more to give her room to move, as she straddled him. She wanted to use his cock, not to fuck, but to rub against her clit, until she came. She was already so close, so this wouldn’t take long.

She lowered herself onto the shaft of his dick, with her lips spread, and started to slowly glide her soaked pussy up and down the length of it. Bill groaned and wrapped his large hands around waist, feeling her movements. “ Are you rubbing your clit?”, he asked innocently, seemingly surprised at what Lily was doing.

“ Mmm, hmm…” Lily answered as she bore down a little harder on his throbbing cock, as reached the large shiny head of it, so he could feel the entrance of her drenched pussy. “ Gooddd, that’s good” , he groaned sliding his hands up and playing with her nipples while she grinded on him. Lily was getting close to cumming herself.. loving the friction of his rock hard dick against her. She grinded her soaked pussy up and down his cock, gyrating her hips in a rhythm now , as she got closer and closer to cumming.

“ Fuck” Lily thought.. She knew she could cum right now, if she wanted to, but she was dying to really feel him inside of her, to cum with him inside of her. She slowly slid her pussy down to the head of his cock once more, but this time, she shifted her hips in just the right way to position his cock to enter her. Then she slowly, slid herself down the length of his huge cock, savoring the feeling him stretching her out and filling her up, hurting her a little when he was all the way inside of her. Lily whimpered a little at that little achey pain she always felt with him when they started to fuck, and started to pull up so he wasn’t so deep. But Bill did not let her, holding her hips firmly down against him , while grinding his hips up hard into her, forcing his cock into her even deeper and making her ride out any aches and pains while he stretched her open to fit him.

“ Mmmm, my big boy”, Lily said softly as the pain faded to pleasure and she was able to ride him more comfortably. She alternated between opening her legs wide and fucking and grinding down hard and deep on his cock, to bringing her knees together and leaning forward, sitting on his cock and bouncing at a quicker pace, leaning forward so he could enjoy the view.

“ Jesusssssssssss”, Bill gasped, caught off guard. He knew how hesitant she usually was to take things this far, especially at work, so he was not expecting this. But he fucking loved it. He closed his eyes and leaned his back in pleasure, while she rode his cock, feeling her wetness dripping all over his cock and thighs. He opened his eyes every now and again to catch glimpses of her gorgeous ass bouncing all over his cock. He could see how shiny and wet it was when she bounced upwards , and he loved watching it sliding into her wet pussy over and over. He had to close his eyes from time to time, or he would cum too soon.

Lily moaned and gasped, as she bore her weight down on the huge head of his cock as it pounded deeply inside of her. She was fucking him hard, but every so often, he would grab and hold her hips and thrust up into her from underneath. She couldn’t take much more, she was going to cum. She leaned back and whispered in his ear between gasps, “ I’m going to cum, but you can’t cum inside of me, ok?”

Bill nodded, and Lily leaned upright, and slowed her riding pace on his cock , sliding herself all the way up and squeezing the big throbbing head of his dick with her pussy, feeling the edges of it. “ *I’m gonna cum, I’m gonna cum, I’m cum..”* Lily repeated in a small voice as she felt her orgasm starting to swell inside of her.. Bill slipped his arms around her and up the front of her , placing his hands on her shoulders, and holding firmly like that. He began thrusting his rock hard cock so deeply, brutally into her that she couldn’t help but cry out in a delicious mix of pain and pleasure. Lily came HARD all over his cock, her pussy clenching and releasing on it tightly over and over , dripping like crazy now all over his thighs and belly.

“Oh my god, oh my god, oh my god!, she said, catching her breath. She was shocked at how intense that was.

She slowly stood up, pulling herself off of him and started to say “ I can’t believe we jus-“ , but Bill clapped his hand over mouth, turned her around, bent her over the desk, and began fucking her fiercely from behind. The sound of his whole body slapping hard against her ass while he fucked her was loud, but neither of them cared at this point. When he lowered his hand, she quickly him not to cum inside of her. “ I won’t”, he said , but she could feel his cock getting harder and his thrusting becoming more urgent and she knew he would cum any moment.

“ Bill.. plea.. “, she started to warn him again, but at that exact moment, Bill grabbed her shoulder and turned her around quickly. He put both hands on her shoulders, pushing her to her knees. “ Open your mouth”, Bill said. And she did. Bill instantly began cumming into Lily’s open mouth, splashing his warm cum all over her tongue. She quickly wrapped her soft, wet mouth around his cock and gently sucked every last splash and drop of cum out him and swallowed.

“ Wow”, Bill said, collapsing back into the old desk chair, “that was fucking intense.”

“ Agreed” , Lily said as they both caught their breath and adjusted their clothing.

As they finished getting dressed Bill asked, “ What was it that you wanted to talk to me about?”

“Nevermind”, Lily replied. “Nothing important.”

Source: reddit.com/r/sexystories/comments/rsplnl/f_cheating_1st_post_be_gentle_encounters