Emma's Night Out

Jared ran to the bathroom and splashed his face with cold water. He'd almost given himself a heart attack from that fantasy.

No he needed to calm down. He needed something but none of his usual distractions worked. He couldn't even bring himself to start anything. The TV was turned off, his pc was turned off. The fridge was already filled and besides, he still wasn't hungry.

He was going mad alone in that apartment. What were they doing?? were they still at the sushi place? Where they going back to his place?

He grabbed his phone to text her but stopped himself, almost throwing it back down. No. he could not intervene! He had to keep distance and not distract her!

If it was going to happen then there had to be no chance of her regretting it, nothing to pull her back to him!

Because this is what he wanted..wasn't it? It was his idea after all, he couldn't back out now that she was already gone..

Emma was his girlfriend, he loved her. He saw a long future together. He saw them growing old together, maybe even starting a family, maybe not. But he saw a life with her.

And currently she at a date with his dad. She was currently attempting to sleep with his dad.

Jonas had been a good dad. He wasn't perfect sure, but who really was?

For his entire life Jonas had always been hugely confident, outgoing and nothing ever seemed to bother him. He even kept a cold head when he divorced his mom.

Jared mostly lived with him and he got to observe his dads many girlfriends growing up. All of them younger than him. Some still adults in their 30's, others still seemed to be in college. Jonas was a playboy. He was what most young men fantasied about being.

Even at his age he had no problem shagging some hot young babe.

Jared had never admitted it to anyone but he was jealous of him. He often lived in his dads shadow, wishing to be more like him. But he realized as soon as high school that wasn't going to happen.

When his close female friends, including one he crushed on, admitted in front of him how hot he was. Well that was it..

He listened for a entire lunch break about how they both wanted to all sorts of dirty stuff with him. Even wondering about his dick size.

Jared had never felt so humiliated before, and that event stuck with him. Burned into his mind forever.

He wondered if that's how it all started. That his secret daddy issues is what lead up to all this? He always though his dad as hotter and more manly than himself.

And now that he was going to have sex with his girlfriend of all people, Jared was once again proven right. That not even she was immune to his charms. That not even his relationships was sacred to him.

Jonas was getting all the girls. He could get his dick inside anyone he wanted, even Emma.

He bet Emma would enjoy sex with his dad more. He bet Jonas was bigger, lasted longer, knew all the tricks to get women to feel good.

After this Emma would forever remember that night when her boyfriends dad fucked her better than he could. She'd probably want to do it again. And Jared would let her. He would let Emma to fuck his dad as often as she could. To spend every night with him, to leave mid date to fuck him if she wanted to.

If Emma stayed with him he could be ok with that. If Emma preferred sex with dad over him he'd be fine with it. He was more scared about the relationship itself.

To him, the best outcome now was her staying with him. That they still do all the couple stuff together but she got sex from dad instead of him.

It wasn't guaranteed to happen though.. In fact the more he thought about it, the less that seemed likely.

7PM, two hours since she left. And still no word from either one, and why would they? Tonight was about them after all.

They were probably back in his place by now. In fact they were probably doing it right this minute.

He probably had her dressed pulled down along the top, exposing her breasts. The bottom pulled up and underwear tossed to the side.

As Jared paced in the apartment alone Jonas probably was inside his girlfriend. They were probably on the bed, naked, him thrusting inside her over and over and over again. She moaned loudly, feeling more pleasure than before. Feeling more excited and turned on than she dad with him. Jonas took her further heights than her boyfriend ever did and was felt so right.

The bed shook, its frame slamming into the wall. The pressure built inside and he fucked harder with each thrust, giving everything into her.

She came as he was still fucking, not remotely slowing down the entire time. Just going harder, faster, harder, faster and....

Jared's entire body shook and he had to sit down. He hadn't even touched himself yet it still happened. He had cum from the sheer fantasy of it. He had stained his underwear from his picturing it. His girlfriend and his dad. Just imagining it, just knowing that it was happening right now. It caused him to get thrown over the edge. Nothing like that had ever happened before.

It seemed Emma was right. They had found his kink. He wasn't as vanilla as he thought.

In reality he was the biggest freak of all.

What kind of man came to the reality of his partner fucking his own dad?

Him apparently..

But it did work out for the best. It had taken so much of him that he felt ready to pass out, like an entire city's worth of power had just gone out inside him. He brushed his teeth, feeling the cold sticky spot in his groin the whole time. He could just take them off but stopped himself, letting it stay. Even just as he was getting ready for bed he had a strange urge to keep them on

somehow that cold wet stain was a reminder of what was happening. It "marked" him somehow. Marked him as the ultimate cuckold, his own dads cuckold son.

He fell asleep in the stained underwear, letting his cum rub against his groin all night, to dry and harden for hours.

When morning came he felt like a mess. Yet not in the bad way but in the tired, recovering phase after a wild night.

In a manner of speaking he had a wild night. His head felt like, body felt heavy. It really happened last night, didn't it?

Opening his eyes and seen the bed empty next to him was confirmation. It really did happen. His girlfriend was still with his dad. She really went out on that date and spent the night.

If all was going according to plan she'd be back today. They never agreed on a time so it could be anything.

The phone showed 7AM. He had slept for an unusually long time. As he slowly got up he felt it when stretching his muscles. The underwear clung to him uncomfortably.

Yet he still wanted to keep it on. It was gross and unsanitary but something in his mind told him to keep it on. That this is what he deserved to wear. That it was somehow his "real" self.

He made his morning coffee and watched the morning news, all the while wearing nothing but that. A ever so slight hint of excitement remained with him the whole time. Like it kept him closer to last night. It wasn't until as far as 9:30 when he finally changed pair. It clung directly to his ball sack and the tip of his penis, he had to pull it off.

As uncomfortable as it was he felt..strangely happy. Or maybe light was more accurate. He felt as if something heavy had been lifted off him last night.

The jealousy of his dad was still there but it didn't seem a bad thing to him. Unlike high school when it killed him on the inside, now he was happy to be in dads shadow. He was happy to give his girlfriend to him. To offer up his most beloved relationship, the love of his life on a silver platter. All for his dad to enjoy.

It felt right, like this was how it was supposed to be.

Emma got back home at 10. She still wore the dress but she wasn't nearly as well put together as last night.

Her hair was sticking out more, makeup gone and her every movement was slow and hanging. She was deadbeat tired. 'Hi.' was all she said when she saw him.

'Hi.' he replied.

As soon as she took off her heels, sighting in relief, she walked up and kissed him lovingly. 'So how was it?' he asked her.

'Intense. But amazing..thanks for letting me do this.'

'You're welcome..I love you.'

'I love you to.' they kissed again. After she finally changed out of her dress and into a oversized hoodie and sweatpants she regaled to him what happened last night.

After he picked her up they went to the sushi place just as planned. Their conversation started off as pretty normal. Just their usual banter. After she took off her coat she noticed how everyone in the restaurant was staring at them. Or more accurately, staring at her. She felt so exposed and she liked it. Everyone's gazes tingled all over her body.

Then there also was the questioning, maybe some judgement in their eyes. They saw this much older man on a date with a young barely 30 year old scantily clad woman. Some of them probably thought him sleazy, which carried some truth to it but clearly he didn't care. In fact Jonas didn't even seem to notice the others. He clearly had experienced it before, he didn't care.

They spent nearly two hours there. Talking well past after finishing their meal. After that they went for a walk around town, just window shopping, or more looking as they didn't buy anything. Their conversation gradually turned more personal. They talked about their past relationships and their ups and downs. Overall it was a pretty nice walk, nothing special happening.

Then around 19 they finally got to his place. She was so nervous by then her entire body was trembling. He must have noticed for when they entered he offered her wine to which she agreed.

They sat in his living room sipping their glasses. She described him as very gentle and didn't pressure her at all. She gradually calmed down and felt safe there. She lost track of time but it must have been hours, possibly until 9PM.

With the mix of wine and his charisma she softened up, and began to feel warm. She moved a little closer to him as the night went on. The talking slowed to crawl as she placed her hand on his thigh, and he did the same in turn. Both moved upwards gradually, slowly until her hand reached his bulge. She rubbed and gently squeezed it.

His hand went under her dress, rubbing her along the thong panties. After touching each other, erecting his penis and making her pussy wetter he leaned in, and they began to kiss. To her surprise he slowly pulled back and asked her if she really was sure. To which she said yes and straddled him. And they began to make out. Things gradually got more and more heated between, the kissing growing more intense and his hands rubbed all over her back.

Then she swiftly got off him, getting on her knees and grabbing his crotch, squeezing and rubbing it in. Then eagerly undid his belt and pulled his sipper. He helped by lifting himself off the couch slightly as she pulled down his pants and then his underwear, his dick springing out freely, pointing straight up fully erected. She stroked it before leaning forward, kissing it along the side before moving her head above it and did something she never did with Jared.

She moved her head down, putting it in her mouth. She gave his dad her very first blowjob.

He never told her, never even hinted at it. She just did it completely by her own will.

He was hard, warm and had this salty, musky taste about him. But she wasn't bothered by it. She was turned on that she didn't think about it, she just did.

Bobbing her head up and down, covering his entire member.

He clearly loved what she was doing, for when she paused and looked up his face was turned red and he was breathing heavily. He then pulled her off him before he came, and took his pants and boxers completely.

Eagerly he took her hand and led her to the bedroom where she laid on her back. He reached inside her dress and pulled off her panties along with the stockings.

He then got on his own knees and repaid her in kind. Locking his mouth onto her pussy and began eating her out. He clearly had a ton of experience. Her pleasure was building up at a ravenous pace. Her legs began bending and kicking out of her control, her arms flayed and grabbed the covers and breathing switching between quick and short to long and slow and everything in between. She came from him. And when she did so she got up and removed the rest of his clothes, standing then there before her naked.

She described him looking much hotter in the nude. Having just the right amount of muscle for her. He pulled off her dress as well and she laid naked underneath him.

She spread her legs as he got on top and pushed inside her.

Their lovemaking was kinda slow at first. He took long and slow movements in and out but as seconds passed he got faster. Faster and faster. Pretty much by the fourth one he held her legs up on shoulders and went in as hard as he could. Slamming down on her over and over again.

The bed creaked, covers flew as the springs bounced. Her entire body shaking back and forth, up and down. He fucked her harder than she'd ever been taken before, seemingly loosing himself to it.

..'And then?'

She stopped, her face was as red as her hair. She pulled some strands behind her ear. 'He well...don't get mad.'

He stared at her in stunned silence. Wanting to take in every single word of what she was about to say.

'He came... A lot in fact.'

'As in?.'

'...As in inside. He came inside me..'

It was as if a invisible lighting bolt struck down on him. An explosion of just pure silence. The shock washed away all other thoughts and feeling he might have had.

Every single time they had sex he always wore a condom.

And now, not only had his own dad gotten his girlfriends first ever blowjob. He came inside of her long before he ever did.

'Wow..'

'Ya...'

'So are you?'

'Dunno..but I don't think I am. Its not really that time of the month so..'

'I see..good. That's..good.'

'So..are you mad?'

He paused as if to double check himself. He had a lot of strong emotions then. Jealousy was first. The fact that not only had his own dad just had sex with his girlfriend he even got further with her on their first night than he did after a full year.

He also felt shame, embarrassment. Once again thrown into dads shadow.

He felt emasculated. Reminded of how dad was the better man. He certainly was better with women.

But mad? 'No..I'm not mad.' and he meant it. Out of all the intense feelings, anger was nowhere close. 'But please, answer me this.' she perked up, listening carefully. 'I uh..Look. My dad..was he..you know.'

'Like..are you asking me if he was bigger or?'

'Well kinda. But..lets put it like this. Which of us are better at sex overall?'

'Oh honey I'm not sure..'

'Babe..please..'

She sighted heavily. She didn't understand why it was so important to him but clearly it was. 'Its hard to tell from just one night..usually. But he was...well. He knew what he was doing. So if I'm completely honest, and this does NOT mean you're a bad boyfriend remember that!

Honest to god, if it just came to sex and nothing else..I would pick your dad.'

'You sure?' his voice jumped up several decimals. Sounding almost high pitched.

'Yes. Like when we do it, its like making love. But he though. Like he fucked me. Compared to you he fucked me harder. Lasted longer than you. And..I can't believe I'm saying this. He is bigger than you as well. Like I had other partners before you who were also bigger but they weren't necessarily better you know? Its like your dad had both the tools AND knew how to use it. Know what I mean?'

His entire body was trembling. His excitement was like Christmas in early childhood 10X. Everything she just aid proved him right. He was so humiliated and something in him loved it. The thrill of being second to him was something that could never be bought.

'Are you sure you're ok with this?'

He kissed her in response. 'I'm more than ok. You're really amazing.' her eyes almost started to glitter upon hearing that.

'Good. I was so worried we did a horrible mistake.'

'You just did the greatest thing ever. You were right before.'

'About what?'

'We found it, my kink. I have never been this turned on before. You know..last night as I imagined it. I..well. I even came..without touching myself.'

Her hand shot up to cover her mouth. 'Ya..I'm serious here. You just had that effect on me.'

'Wow..Like bro..'

'So..what now?'

'I dunno..but I'm exhausted and wanna be a couch potato all day now.'

'Of course. I'll order some pizza.'

'Thanks babe.'

They spent the entire day being completely lazy. Videogames and trashy videos online, along with copious amounts of soda and junk food. The perfect day after crossing the most extreme line just yesterday.

Thursday, their final week of vacation was almost over. That Monday normal life would resume. And Jared wasn't happy about it. He felt like after this it should be a change. Even a small one, just not back to business as usual.

So he did what he now did best apparently. She talked to Emma. 'So I got a question.'

'Hmm?'

'If you got the chance to..you know. Sleep with my dad again. Would you do it?'

She turned him slightly surprised but not disproving. 'Hell ya I would. No doubt.'

'Good!..so wanna..'

'Organize a date again?'

'I was thinking more perhaps.'

Now she was leaning in, intrigued. 'What if we make it a regular thing? That instead of this once in a while dates you see each other on a normal bases?'

'Its a interesting idea. But I don't know yet. I feel like first we have to do this a few more times. Maybe two or three and see how it feels then.'

'Sure. Absolutely.'

'So I guess I'll call him then.'

'Ya, do it.'

She took her phone and dialed. It didn't take long for him to answer thankfully. 'Hey Jonas. Ya I loved our night together. So much so that I was hoping to do it again...yes..Yes of course he's on board...huh uh..sure that works. Ya I'll see you then. Bye!' she hung up. 'We're meeting this Saturday for lunch.'

'Fantastic!'

'So again, you sure you're ok with it?'

'I think I want as much as you really.'

'You sure about that?' She asked kinda smugly, gesturing clearly to his.."skills".

He felt some tingling in his gut upon that. If she started looking forward to it more than him, then all the better.

Neither had any idea where all this would lead. But regardless, they were eager to find out.

Six months later

It was Christmas. Snow painted the outside world in a soft white. While the sky remained dark the streets and houses were lit up in all sorts of jolly decorations. Families held their yearly traditions and businesses closed up..mostly.

Jared filled the bowls with the Christmas snacks that both Emma and Jonas spent all day yesterday preparing. Both father and son wore their finest suits, and Emma dressed in a gorgeous red dress. As per usual style since last summer she showed plenty of cleavage and the bottom half reached all the way down to her ankles but had a open slit on the side, revealing her entire leg and stopping even above her hip. Revealing her lack of underwear to those who paid attention.

The time showed 17:05, the guests should be there any minute. 'I'll just get cider before they get here.' Jonas said as he went down to his basement.

With him gone, Jared creeped up behind Emma. 'You're looking stunning. Irresistible even.' he tried to sneak his hands around her waist but while smiling she stopped him. 'You know the rules babe.' It always hurt so good whenever she rejected like that and she knew it.

The doorbell rang. 'Well, go get it.' she ordered him. Something he had gotten used to by now. He felt a unexpected light slap on his ass as he walked past her. Turning to see her mischievous grin behind him. He opened to see a group of older man, ranging anywhere from their early forties to late fifties. Some of them brought their wives of the same age but most came alone. 'Hey Jared, good to see you again!'