Making up for Lost Time Ch. 02

Simon sat there, twiddling his thumbs and bouncing his knee, not knowing what else to do with the nervous energy that was flowing through him. After all, it wasn't like there was an established code of behaviour for when your wife was on a date with another man--especially when that man was your son's friend.

It had been an hour or so since Anna, his wife, had left the house in a taxi, her clothes and makeup rendering her more beautiful than he could ever remember seeing her. His son's friend Jacob was a lucky guy, that was for sure. And if he played his cards right, he would be able to get a whole lot luckier.

Simon couldn't help but chuckle at the bizarreness of the situation. Had someone told him just a few weeks earlier that his wife would be out on a date without him, he would have laughed in their face. But here they were. He wondered which of the two of them was feeling more nervous at this moment.

All of a sudden, he had an idea. He brought up the maps app on his phone, remembering that he and his wife had once shared their location with each other on holiday. With any luck, it would still be active.

Bingo. A dot representing her location popped up in town. She had wisely chosen not to go somewhere local, where prying eyes might recognise her or her date and wonder what the two of them were doing together. Instead, she was currently inside an Irish pub he had never heard of on the other side of town.

Seeing where she was had the curious effect of calming him down, while also simultaneously setting his mind racing. He cursed himself for not having thought of tracking her earlier. At least from now on he'd be able to see where she was going and imagine what she was up to.

***

Across town, Anna had no need to imagine what was happening to her--she was living it, after all. She had arrived not long ago to find Jacob already inside, exactly as she had instructed him via text.

She was disappointed that he hadn't made much effort in his appearance. He was dressed casually, much the same as he always was. It made her look a little desperate in comparison, considering how glammed up she was. But then again, he was just a kid after all. He probably didn't even own a suit.

After an awkward, nervy hello, he had offered to get her a drink while she found them a table. Having found one, she fidgeted in her seat, tugging self-consciously at her dress. She was simultaneously flattered and somewhat perturbed to notice more than a couple of hungry eyes looking her way.

She asked herself yet again what the hell she was doing. Here she was, a hitherto perfectly respectable wife and mother, out on a date with another man.

For what seemed like the hundredth time, she considered her motivations for agreeing to the date. In some sense it was revenge against Simon for misleading her. But that seemed like pretty weak reasoning when this eventuality was seemingly exactly what he wanted.

Partly it was to placate Jacob, who she saw as a fairly innocent party in all this. Besides, she couldn't deny she was flattered by his interest in her.

Then there were her own reasons. It was true her life up to now had been relatively... unadventurous. The fact that their son would soon be off to university had already made it seem like the perfect opportunity to remedy that by embracing new things. And then, when her husband had dropped the bombshell that he didn't mind her being shown attention by other men, it felt natural to follow the interest up.

What she still couldn't fathom was why her husband had been orchestrating this in the first place. Their marriage had always been happy, at least as far as she was concerned. The only explanation that made sense in her mind was that he wanted an excuse to sleep around himself. If he'd been successful in surreptitiously pushing her into Jacob's arms, he could have manufactured a way of discovering them. Then he would be able to discover her cheating, meaning she wouldn't have a leg to stand on if he said he wanted an open marriage.

She was still pondering all this when Jacob reappeared at the table and placed her drink in front of her before taking a seat himself. For a second they both took long sips, pondering what to say. Anna took the initiative. To break the silence, she launched into some idle chit-chat about his hopes for university and what he planned to do afterwards. She'd always been good at that, as most women have to be.

As she expected, in the cold light of day, unguided by her duplicitous husband, Jacob really wasn't all that attractive to her. They were very different people, at very different stages of their lives, and as a result had very little in common. Inevitably, the conversation, such as it was, turned to the only thing that they did share. A place in Simon's fantasy.

"So," she said. "How... how did you get involved in all this?"

"Oh, um, well it started when I was fixing Simon's laptop and I found some stories."

"Stories?"

"Yeah, stories he was reading about... cuckolding and stuff."

Cuckolding? She had a vague memory of having heard the term before, but no idea what it meant. It sounded vaguely Shakespearean.

"What the hell's a cuckold?"

"Oh, you don't know?"

She shook her head.

"Well I mean I don't know too much about it myself, but it's basically a man whose wife sleeps with other guys."

He read stories about it? That's why her husband had set this whole thing up? This was too much for her to deal with right now.

"Actually, you know what? Let's stop talking about Simon."

They returned to their drinks. It was up to her to break the silence a second time. "I really hope you don't currently have a girlfriend, by the way."

"Oh, haha, no I don't. Not now or ever."

"So you're a virgin, then?" It was an awkward question to ask, but she had to admit she was interested in the answer.

He simply nodded, turning slightly pink in the face. To both of them, this was beginning to feel a bit like a job interview, or perhaps an inquisition. Anna knew Dutch courage was the order of the day. She wasn't that much of a drinker on normal occasions. But this was anything but normal. And it would help both of them loosen up. She sent Jacob to get them another.

***

A few more drinks in and, as she had hoped, their mutual tipsiness was improving things. Despite earlier declaring the topic of her husband off limits, her curiosity was getting the better of her.

"One thing I don't get. So you discover my husband is a cockle, or whatever you called it."

"Cuckold."

"Yeah, that. How the hell does that lead to the two of you coming up with your idiotic plan?"

"I suppose when I saw that story, it felt like an opportunity, you know? One that I couldn't pass up. So I told Simon I'd be willing to help make it happen in real life."

She felt slightly better knowing that Jacob was an all too willing participant in their game, rather than just a puppet of her husband.

"What do you mean 'an opportunity you couldn't pass up'? I'm sure there are far easier ways to have sex with someone."

"Sure, but not sex with you. I've kind of... well... had a crush on you. For as long as I've been able to have crushes."

"Oh my God, you're just flattering me now."

"It's true!"

"I mean, I'm not even in the top three sexiest mums in your little friendship group..."

"Well that's part of what's hot about you. You could easily be the sexiest. But it's like you choose not to. I mean, If you dressed like you are right now every day, everyone would think of you as a MILF, no doubt."

She couldn't help but laugh at that. It was true she didn't think she looked bad for a woman of her age. But the notion of herself as a MILF...

"Anyway, so you're saying you didn't have a crush on me back?" Jacob added cheekily.

"No, of course not! First off, I had no idea you felt like that. And besides, you were just another one of my son's friends..." She took a sip before adding, conspiratorially: "Of course maybe it would have been different if I knew what you were allegedly packing."

"Allegedly?"

"Yep. What is it the kids call it? Catfishing? It could be anyone's penis that you sent me."

"I don't mind giving you a live demonstration if you want."

"Hmm," she laughed. "I'll bear that in mind."

***

While all this was happening, Simon was driving himself to distraction, picking up and putting down his phone, only to see his wife remained in the same spot.

What were they talking about? Was it going well? Were they hitting it off? Even now he knew where they were, the lack of details was agonising, albeit not entirely unpleasant.

His mind left to wander, he entertained fantasies of them having already done the deed in the toilets, his wife playing the role of the insatiable slut he had read about in so many of the stories he consumed.

Of course he was worried, too. The transition of his fantasy into reality brought up plenty of anxieties around whether he was destroying his marriage. His simultaneous fear and excitement fed into each other, heightening the sensation of both.

He looked down at his phone again, and his eyes widened in sudden surprise. They were on the move.

***

After the imbibing of plenty more alcoholic beverages, and more flirtatious conversation, they decided to vacate the premises of the pub they were in and venture off in search of somewhere else. It wasn't long before they stumbled upon the entrance to a club. Now neither of them were club people, in any sense of the word, being a nerd and a mother respectively. But Anna figured this was a night for trying new experiences, and duly dragged Jacob inside.

Inside was dark, noisy and packed with people, as any club would be. She had to shout in Jacob's ear to get him to come with her towards the place where people were dancing.

As they made their way through the throng of people, she couldn't help but notice the general youth of the clientele, with many girls both much younger and much more sluttily dressed than her. Still, she didn't feel as out of place as she expected.

She was definitely drunk now, drunker than she had been for a very long time. Rare as it was, she didn't know her drunk self very well. One thing was becoming increasingly evident and increasingly hard to deny, however. She was horny.

They found a space and started dancing together, albeit at arm's length. Anna was frustrated at Jacob's lack of confidence. She wanted him to reach across, wrap his arms around her, and snog her silly. But here she was, sending every signal known to man, and not getting anything back.

But maybe that was the problem. He wasn't a man, not really. It seemed she would have to up the ante to get what she wanted.

Before she could put that into action, however, it became apparent that her signals were attracting the attention of some of the other men around her on the dance floor. Looking around, she made eye contact with one man in particular. He was far from her usual type, muscled and slightly seedy looking in his skinny jeans and shirt. A wicked thought came over her.

"I'm thirsty," she told Jacob. "Could you get me a drink?"

He dutifully obeyed her request. As he retreated, the man made his move, sidling on up to her. She turned away from him, and he was briefly disappointed. But then she ground her pert arse into the stranger's crotch, a gratifyingly hard lump pushing back into her. His hands were on her hips. She felt small all of a sudden, a puppet being directed by another. It wasn't a bad feeling.

After dancing close for a while, he spun her round to face him. Before she could even consider what was occurring, their lips met. This was no chaste peck, more a battle to see who could stick their tongue further down each other's throat. The overwhelming taste was of alcohol.

Mouths disengaging, she couldn't help but glance down to survey the effect she had had on him. Even through the tightness of his jeans the outline of his hardness was obvious. It didn't seem as big as Jacob's, but it was certainly bigger than her husbands.

Her husband. This was going too far. She was here to punish Simon for his machinations, not to hook up with random men. She was a wife and mother, for goodness sake. With a soft but insistent pressure, she disentangled herself from the kiss before deploying the same trick she had just used to get rid of Jacob.

***

Back at home, Simon was in disbelief. It was quite incredible to imagine his wife in such a setting. Clubbing was not something that she had ever expressed an interest in, but he couldn't believe someone like Jacob would have suggested it as an activity. Which meant the impetus must have come from Anna.

For once, Simon's fantasies were paling in comparison to the truth of the situation. He couldn't begin to imagine, as he looked at the blinking dot revealing her location, that his up-to-that-moment faithful wife was kissing another man--and not even the other man that she had started the night with.

***

Just as the stranger disappeared from sight headed to the bar, Jacob appeared once more, Anna's drink in his hand.

"Quick," she giggled, "we have to get out of here."

"We do? What about your drink?"

In response, she grabbed it from his hand and, much to his apparent surprise, downed the whole lot.

"Come on," she said, dragging him off the dancefloor. "Before he comes back."

"Before who comes back?"

"I don't know. Some guy. He came on to me once you'd gone. And I... I may have kissed him."

"Y-you did?" The poor kid looked crestfallen. She almost felt like apologising. But then she thought of something he'd much prefer.

"I'll be honest, I wasn't expecting my first kiss outside my marriage to be some random guy on the dancefloor."

"You weren't?"

"Well, all signs were pointing to you..." she said, the implication perking him up. "Oh don't look so disappointed. Here."

She leaned forwards and planted her mouth on his. Within a microsecond they were hungrily kissing one another, tongues duelling for advantage. That was one way to break the ice.

She noted with approval that Jacob was a better kisser than the stranger, more tender and less forceful. There she was, kissing her second man in as many minutes. The longer the kiss went on, the more her pussy tingled. But they couldn't stay there forever, not with the stranger on the prowl. She broke off the kiss and dragged Jacob outside.

***

Now that they were more comfortable in each other's presence, Anna wanted to go somewhere quieter, so they departed the club and headed to a bar, where they ordered a drink before finding a secluded booth.

Anna found herself very much in the mood to continue with her flirtation. She decided to probe a bit more regarding her husband's behaviour.

"So... Who's idea was it to cum in my bikini bottoms?"

"Both of us I guess. I told him I'd done it before, and he saw the opportunity for me to do it again.

"Wait, 'done it before'? That wasn't the first time you'd done it?"

"Oh right, you don't know. Yeah. I did. That's kinda how my crush began actually. We were all round your house and someone dared me to steal them. I forgot all about them until I was back home. Once I rediscovered them in my pocket, I couldn't resist using them to wank with."

"Jacob! That's outrageous," she laughed.

"He said he vaguely remembered them going missing, I guess you don't."

"No I don't. I mean I probably would remember if I had found out what ended up happening to them..."

"How would you have reacted if you had found out?"

"Are you asking if I'd have spanked you?" she giggled, then shrugged. "I think you'd have gotten off lightly. It's an inconvenience. But it's flattering too, I guess."

Jacob looked thoughtful for a moment. "What if I stole them right now?"

"Well I have to admit I'd be very impressed. There's not much access, after all."

"Oh I don't think I'll need to take them myself. I think you'll give them to me right now."

Something about his sudden burst of confidence was a real turn on for her. They locked eyes for a while, a silent battle of wills occurring. And then he won. She went to stand.

"Where are you going?" said Jacob.

"The bathroom. I thought you wanted me to take off my knickers?"

"You can do that right here."

He was really pushing his luck. But she couldn't deny there was something thrilling about the thought of taking them off in public. And sober, boring Anna was nowhere to be found right now. She sat back down in her chair, carefully hiking up her dress slightly as she did so. Nothing was on display, but it gave her just enough wiggle room to grasp the sidebands of her underwear. A few seconds of discreet wriggling and glances over her shoulder later, and they were around her ankles.

Jacob had watched the whole affair with a great deal of intrigue. Seeing his friend's mother, the object of all his fantasies, behave so lewdly was a dream come true--as the bulge in his trousers could attest.

"Care to pick them up then?" she asked coyly.

He bent down underneath the table as if he had dropped something, but instead worked quickly to unhook Anna's silky black lingerie from her heels. He couldn't resist sneaking a peek up her skirt while he was down there. It was too dark to make anything out, but the thought of her pussy being utterly exposed was intoxicating.

"Thank you Anna," he said smugly, sitting back up while she returned her dress to its default position. He pocketed his haul and the conversation turned to other matters.

***

A few drinks later, Anna indicated she was ready to leave. Jacob headed to the toilets, leaving the bottomless Anna squirming slightly in her seat. She could feel the wetness of her exposed pussy thanks to the occasional breeze blowing against it. Sitting there like that, with everyone but Jacob none the wiser about her behaviour, had definitely upped her horniness ante.

Eventually, Jacob returned.

"I need to use the bathroom myself," she said. "And I hope you're not expecting me to leave without any panties?"

Anna held out her handbag expectantly and, to her surprise, he put the knickers inside, albeit while giving her a strange look. She was half expecting him to refuse to give them back. A part of her even wanted him to do that. But apparently he had decided to behave.

"Thank you."

In the toilets, she found a stall and locked the door behind her. Her first surprise after pulling her knickers out of her bag was that they were neatly folded. Having a teenage son herself, she didn't think that was a skill in their repertoire.

It was the next surprise that elicited an actual gasp, however. Unfolding them had revealed her thong wasn't the only thing she was holding in her hands. The bastard had cum in them, presumably just now when he had gone to the bathroom herself.

For a few seconds she just stared at the sticky white mess pooling in the gusset. Jacob's propensity for cumming in her underwear seemed just as strong as her husband's desire to share her. Men and their fetishes...

What was Jacob expecting her to do? She couldn't put them back in her bag for fear of them leaking over everything. And she wasn't going to just abandon her cum-stained underwear in a public toilet. Which left just one course of action.

She delicately manoeuvred them around each of her heels, trying desperately not to spill any cum on herself, before gingerly pulling them up her legs. Then, with an audible splat, his mess made contact with her freshly shaved cunt.

Unfortunately, it was then she noticed she hadn't been entirely successful at containing Jacob's voluminous load. A long smear of cum snaked up her thigh, finishing well below the hem of her dress. She couldn't leave it. Before her conscious brain could even rationalise against it, she reached out a finger, scooped it up and deposited it in her mouth.