Practice Dates – Erotic Couplings – Free Sex Story

1 Star2 Stars3 Stars4 Stars5 Stars
Loading...


*Author’s note; longtime visitors to Literotica may recognise this story. I posted an earlier version of it on here years ago and later took it down. I thought it was lost, but I found the document on my hard drive and thought I’d upload it again. I couldn’t remember my old login details, hence why it’s on a new account. It’s been edited slightly but the base story is still the same.

It deals with themes of adultery and manipulation. If that isn’t your thing I would suggest looking elsewhere. These aren’t real people though, none of this happened in real life; it’s just a story. Don’t take it too seriously.*

Cat had never set out to cheat on her husband. Her wedding day had been one of the greatest experiences of her life and when she said her vows she meant them completely. She never intended to be anything less than a loving and faithful Wife and she truly loved Graham more than anyone else in the world. She’d welcomed the feel of the white gold ring as he slid it onto her finger and committed herself to him forever, but now the sight of that same metal band seemed to mock her. It represented all of her broken promises and made her feel flushed with guilt. Even as she thought back over recent events, she couldn’t figure out exactly how she reached this point. The seduction had been so gradual that it was difficult to pinpoint when it changed from a bit of playful flirting into something sordid and she felt utterly, terribly ashamed at herself.

But strangely, those same feelings had a flipside. They intensified every minor detail and magnified each aspect of these sensations that were supposed to be forbidden to her. So as she lay there on the most comfortable bed she’d ever felt in her life, drenched in sweat, naked as the day she was born and with another man’s cock thrusting into her, her emotions were a heady mixture of lust and guilt that made the Orgasm rising within her increasingly hard to resist.

****

It all started a few months earlier. She and Graham had been married for just over eighteen months and put a deposit down on their first house. The mortgage payments were noticeably higher than their rent though, so while she had been quite content working in a café up until that point, she’d been forced to bite the bullet and get an admin job at a legal firm to help balance their bills.

The office she found herself in was only one floor and wasn’t very large, but there were a lot of people working there and they seemed forever stretched for room. She was surprised therefore when the training was over and she was shown her work space, a desk in a separate office away from everybody else. Her supervisor Alison apologised for sticking her in there, but there simply wasn’t enough room for another person in the main area.

“That’s all right,” she had replied, “But don’t you think someone else should have this?”

“What do you mean?” the middle aged lady had said.

“Well, I Love having my own office and all, but I’m only admin, this looks like it should be reserved for one of the bosses or team leaders?”

“Oh right,” Alison smiled, “It’s not just for you. You’ll be sharing this room with the area manager. I don’t think you’ve met him yet, he’s been away on leave since you first joined us.

“Ah that makes sense,” Cat said, trying not to feel embarrassed at her mistake, “I guess that won’t be too bad. When is he getting back?”

Not for another week yet,” said Alison, “But not to worry, I’m only at the other end of the corridor and you can always come and join the rest of us for coffee whenever you like. We certainly didn’t intend to isolate you like this, there’s just not enough room.”

“No, no it’s fine, I’m sure I’ll be all right.”

“Well then,” said Alison, “I’ll leave you to get settled in. You know where I am if you need me.”

“Thanks,” said Cat, taking in her surroundings as Alison walked off. She should have realised, they wouldn’t have put two desks in here after all if she was meant to be on her own and there’s no way they would give someone in admin their own room. She started to unpack her few belongings — a framed picture of her and Graham on their wedding day, a coffee mug and some home stationery — and decided to settle in.

in.

****

The following week was one of the most boring she’d ever had to endure. She had no doubt that Alison meant well, but separated from the rest of the workforce like she was, it was difficult to ingratiate herself with her co-workers. She didn’t tend to drink more than two or three cups of coffee a day and the work she was completing was relatively straightforward so there were hardly any queries to bring up. All of which meant she had no reason other than boredom to leave the room and she didn’t want to make herself look work shy on her first week.

Consequently, each day crawled past at a snail’s pace and became increasingly tedious as the hours ticked by. When Friday finally came around, she felt as though she was losing brain cells with each second that went past and had seriously considered throwing in the towel, but when she vented her frustrations at Graham that night, he talked her out of it.

“Come on,” he said, “It’s only been a week. You can’t give up this early.”

“I know,” she said, “But it’s just so boring! I do nothing but file things all day and there’s no-one to talk to! I feel like I’m going to go mad.”

“It can’t be that bad,” he replied, looking at her with that sympathetic glimmer in his eyes that had first made her fall in Love with him, “Besides, aren’t you getting a roommate next week?”

“Yes, the area manager,” she sighed, “The boss himself, I’m sure that’ll be loads of fun!”

“You never know,” he said, “they might be perfectly decent. Besides, even if they’re the most bookish, pedantic jobsworth in the world, it’ll be better than being on your own.”

“I guess you’re right,” she said considering his words, they did have bills to pay after all, “And if I don’t like him at least I’ll still be taking home a wage until I can find something better.

She lay against his chest and listened to his heartbeat, how bad could it be?

****

When Monday came around she had dreaded going back into that cramped little room and squeezing herself behind that desk for five whole days. She was not looking forward to having to share the room with her new boss either and had mental images of a flashy, arrogant asshole to put up with, so when he stepped in to the room about ten minutes after her, she had to do a double take.

He was a huge man, standing at over six feet tall with broad shoulders and a barrel chest. Not only that, but she knew him, it was her friend Gemma’s father. And he recognised her too.

“My goodness,” he said, a smile coming easily to his face, “Is that you Catherine?”

“Hello Mr. Hembry,” she replied shyly.

“Please Catherine, we’re going to be working together, call me CJ,” he said effortlessly and suddenly, she was a sixteen year old again. She’d had a crush on Gemma’s dad as a schoolgirl, but hadn’t seen him since he drove both girls home from their graduation dance. She’d got herself doled up as glamorously as possible that night but he’d barely looked at her twice and now here he was, standing right in front of her. He had a few more grey hairs, but otherwise looked the same.

“Okay CJ, nice to see you again.”

“You too,” he replied, still smiling at her warmly.

Once they’d got over the initial pleasantries, Cat was pleased to find that she and CJ got on remarkably and they didn’t stop chatting for the entire day. She told him about her life since she’d last seen him, how she’d spent a year trekking through South America after she’d graduated from school and then gone to University when she returned home. She also told him about how she’d met Graham right at the end of her course, fallen in Love and eventually married him, then pretty much everything that led to her putting in a job application. She found that he was easy to talk to, he listened attentively and seemed to value every word she said.

She was sad to hear about how his marriage had collapsed a few years ago. She knew about the divorce of course, Gemma had told her about it, but to hear first-hand how it unfolded and seeing the lingering traces of regret in him as he discussed it was tough. He still had a healthy relationship with his daughter though and also seemed very proud of the company he was in charge of.

He told her how he was one of the three senior partners, but had drawn the short straw when deciding which building they’d all be working out of and wound up here, although he did say that seeing her sat opposite him made it seem less like a bad position now. She’d laughed at that and called him an “old smoothie” which he seemed to like. They chatted so effortlessly that the hours flew by and for the first time, Cat left the office genuinely looking forward to work the next day.

The next couple of weeks followed just as easily. Graham couldn’t help but comment on how she seemed to be enjoying her new job and even teased her a little bit about the “lecherous old man perving over her,” which made them both laugh. What she didn’t tell him though was that their conversation had started getting a bit racy recently. She would never do anything of course, but as their friendship developed more innuendos and cheeky jokes worked their way into their everyday chats. It gave her a bit of a thrill actually, she’d fantasised about him more than once as a teenager, so to suddenly reconnect with him as an Adult and flirt every day made her feel rather naughty. Sometimes she wondered if exchanging double-entendres with her friend’s dad was a bad idea but on the rare occasions she gave it a second thought, she brushed her doubts away. It was just harmless flirting after all, it was only fun to pass the time and no-one would ever know, what harm could it possibly do?

****

A month after CJ had first walked back into her life though, they had an interesting conversation. It was a typical Thursday afternoon, the majority of the week’s work was done and they were both filling their time with odd little jobs that needed doing, rather than fighting deadlines and battling the clock. The pace was relaxed and easy and it was then that CJ mentioned he was considering dating again.

“Oh exciting,” said Cat, “What’s brought this on?”

“I’ve been considering it for a few weeks,” CJ answered, “I think it’s about time that I put myself out there again.”

“Good, you deserve somebody.”

“To be quite honest Catherine,” he said, “I’m more than a little nervous.”

“Nervous? Why?”

“I don’t know, I just…” he stammered, took a moment then continued, “Sometimes I think I’m too old to try my hand at this again.”

“Too old? No come off it CJ,” she said, “You’re…what? Fifty five? Fifty six?”

“Sixty one.”

“No way,” she said, “I never figured you for being in your sixties, I’m impressed.”

“Thank you my dear, but yes I’m what the more generous call the vintage type and what the less generous call an old fart,” he smiled sadly.

“Well I’m sure whoever you go out with will find you quite charming and be swept off their feet regardless of their age.”

“But everything’s so different now. I haven’t dated a woman, when my Wife and I first met it was called ‘courting.'”

“You just need a confidence boost,” she said, “Come on CJ, I’ve seen you in meetings and working round here. You’re always in charge, try thinking like that when you meet someone.”

“Try acting like the bigshot boss?” he chuckled.

“Yeah, why not? Some women like that sort of thing.”

“Is that how Graham won you over?”

“Yes, sort of…well, he made me laugh and looked good in a suit,” she laughed.

“I’ve got plenty of suits,” he said.

And I’m sure you’ll look incredibly dashing in them,” she said, “Why don’t I help you sign up to a dating website?”

“Uh…is that how people meet nowadays?” he said, a look of terrified uncertainty crossed his face.

Advertisements

“Yeah, Internet dating is the thing. All the singles do it.”

“Oh heavens, Internet dating? I have a hard enough time getting Youtube to work.”

“Don’t worry, I’ll help you set something up,” she laughed again, “Come on it’ll be fun. Besides, I want to help.”

“Really?” he said, his eyes flicking up at her.

“Yeah, let me give you a hand.”

“Well…if you really want to help, can I ask you a favour?”

“Sure.”

“How would you feel about a dry run?” he said, shifting awkwardly.

“What do you mean?”

“You know, I was thinking maybe you could help with a…fake night out with me? So I can get some tips.”

“You mean like some sort of practice date?” she asked, starting to feel as awkward.

“Yeah…just to get myself back up to speed.”

A heavy silence filled the room.

“What…what would that entail?” she said.

“I don’t know, I only just thought of it,” he replied, “Maybe before I arrange a date with anyone I could go on a…a practice date with you? I’d take you out to a restaurant, get used to spending an evening with a woman again.”

“You…don’t mean…”

“Mean what? Oh Christ, good God Catherine, no,” he spluttered, “No funny stuff at all. Just a safe night out where I’d show you how I’d behave, what I’d dress in, how I’d talk…that sort of thing.”

“Right…”

“And at the end, you could give me some tips and I’d take you home. That’s all.”

“That’s all?”

“Yes, just a practice run before the real thing.”

They both went quiet. CJ looked unbelievably embarrassed and started playing with a pen, unable to look at her. Cat’s mind raced as she wondered what to do. He was a lovely guy and it all sounded innocent enough, but it was a bit unusual to say the least. She wouldn’t want Graham doing it with one of his co-workers and if anyone they knew saw them out…

“I’m sorry CJ,” she said, “I can’t.”

“No?”

“No, I’m sorry. I really am. But it’s a bit…odd.”

“Okay,” he said sadly.

“Look, don’t worry,” she said, smiling and reaching across the desk to take his hand sympathetically, “You don’t need a practice run, you’ll be fine.”

“I’m a foolish old man, I…I’m so sorry, I shouldn’t have asked.”

“No, no, it’s fine,” she replied, “It’s actually quite flattering.”

“Yeah?”

“Yeah, I’m glad that you feel you can trust me and if things were different I’d consider it. But I’m married and even if it is completely innocent, it’s…you know…”

“Okay, I suppose you’re right. Shall we forget we had this conversation?”

“If you wish.”

“Yes, now get back to work you. That’s enough slacking on the job.”

She laughed easily and went back to the spreadsheet she was updating.

****

The rest of the afternoon went by without a hitch and the following day, everything seemed back to normal. They spent the day sorting out the last few jobs before the weekend, chatting casually and engaging in some light banter, just like any other Friday on the job. But the following Monday, things changed.

That weekend had been Gemma’s Hen Party and as usual with her, things got messy. They started by doing shots at 5pm, were out until the early hours and when Cat woke the next morning, she had the worst hangover since her student days and no memory of anything after about 9pm. After spending all of Saturday and most of Sunday feeling rotten, she returned to work and found CJ already sat at his desk. But there was something different about him, he seemed very serious that morning which wasn’t like CJ at all.

“Morning Catherine,” he said.

“Morning,” she said with some trepidation, “Uh…is everything all right?”

“Sit down,” he said, “Do you mind if we talk?”

“No that’s fine,” she replied as she seated herself, “What’s up?”

“Cat, I know you went out with Gemma and the girls this weekend, but I need to ask you something…are you and Graham having trouble at home?”

“No,” she said with some worry, “Why? Has Gemma told you something? Graham and me are fine.”

“No, she hasn’t said a word. It’s just…well, she had some computer trouble at the weekend and asked me round to help her out. I had to go through her hard drive quite thoroughly,” he suddenly reached into his pocket, “And I found this.”

And with that he pulled out a paper print out of a photo from the Hen Party. It was a shot of a male stripper with his hand on the back of a woman’s head, his fingers wrapped in her hair as his dick went into her mouth.

Cat’s mouth.

“Oh my God,” she practically jumped out of her chair, panic welling up inside her, “CJ…what…what the fuck is this?”

“Catherine please, calm down,” he said gently.

“But…oh god CJ, I don’t even remember doing this?” Her mind was racing, this was the kind of thing that could end her marriage.

“Well you had a lot to drink didn’t you?”

“Gallons,” she said, “But…that’s…oh fuck CJ, oh fuck.” She held her head in her hands and tried not to cry.

“Look, don’t worry too much,” he said trying to soothe her, “Everyone does stupid things while drunk and besides, I don’t think you’re the only one who can’t remember this.”

“What do you mean?” she said, the first tears slipping from her eyes.

“Well Gemma was in a rough state all weekend and she told me she’d added these to her computer on the night itself. I think she was blind drunk when she did it and she didn’t even use it once while I was there. I’ve taken all the incriminating photos off her hard drive and put them on a USB stick. If you want them you can have them and confess all to Graham, but do you want to know what I think?”

What?”

“I think this was just a silly drunken mistake. You had no idea what you were doing and I think admitting to it would do more harm than good in the long run.”

She mulled that over for a few seconds, he may have a point. She didn’t want to end her marriage but at the same time, she felt terrible and wondered if confessing was the right thing to do.

“Now, I’m going to have to leave you for an hour,” he said, “I’ve got a meeting and I’m already late for it. But think it over and if you want to talk when I get back, I’m all yours.”

“Thanks CJ,” she smiled weakly as he stepped out.

“My pleasure.”

For the next hour she got nothing done. She weighed up all her options again and again and for a while, was totally lost. But when CJ got back slightly later than he’d said, she knew what she was going to do.

“Nobody else knows do they?” she said seriously.

“No, I really don’t think they do.”

“Okay,” she took a deep breath, “I’m not going to tell him. And don’t give me the USB stick, if I have it there’s every chance he’ll find it. It’s better if you take it and just delete them.”

“No problem,” he said, “I won’t tell a soul.”

She breathed an immense sigh of relief. She wasn’t sure if this was the right decision but she’d made it and she was going to stick to it.

“Right,” she said gathering herself, “Let’s get back to work. These files aren’t going to sort themselves.”

“Of course,” he said and just for a second, she thought she saw the ghost of a smile cross his face.

****

After that, things got back to normal pretty quickly. Cat felt pretty guilty for a short while, but she soon put it behind her and tried not to think about it. She’d been encouraged when Graham didn’t seem to pick up on anything different in her behaviour. Slipping back into his hugs had been easy and she still felt an overwhelming Love from him at all times. Nothing ever happened really, just a silly mistake, so she put it in her past and never said a word. Besides, it was difficult to think of herself as a cheater when she had literally no recollection of the event.

She also found a chance to concentrate on something else. One morning CJ let slip that he’d met someone online through the dating profile she’d helped him set up. They were due to go out together the following Thursday and she did her best to encourage him. For one thing it took her mind off things, but for another he seemed genuinely lonely sometimes and she thought he deserved more.

error: Content is protected due to Copyright law !