Undoing the Shy – a cuckold story

A year ago it would have seemed odd to Jay that his brother Drew wanted to come round tonight. They had only just seen each other at the weekend after all. Georgia had made mexican food and they had all sat and watched the game together with beers and delicious over stuffed burritos. Yet Drew was asking to come round on his own tonight to Jay’s place.

Jay gave his response a second and third thought, his thumb hovering over the keypad of his phone. They were getting along much better now and he didn’t want to ruin it by blowing him off with a lame excuse.

Sure. What time? I’ll be home after seven.

I’ll swing by at half eight. Make sure you’ve got some cold ones in the fridge.

Lolz. Will do. See you then.

It was a hot one on the building site today. Jay worked himself to the bone, sweating and panting as he carried lumber and other building materials up and down the scaffolding. By the time he got home, his powerful muscles were sore and his skin slightly more than tanned as he had taken his shirt off part way through the day. When he got through the door just after seven, he flopped onto the couch immediately with a cold one in hand. He knew he smelled bad but he just could not move another inch just yet. His shower would have to wait.

Arm behind his head he sipped his beer and gazed at the spinning arms of the ceiling fan, his mind wandering aimlessly. The next thing he knew there was a knock at the door.

Shit.

He’d fallen asleep.

‘Coming!’ he cried sitting up, taking a few seconds to deal with the head rush. His beer had spilt on the couch. ‘Fuck.’

He hastily threw his shirt over it and answered the door to find Drew standing there.

‘Jeez. No need to go to any effort dude,’ chuckled his brother breezing past him into the apartment. He was holding a pizza box and a couple of boxes of sides.

A little embarrassed, Jay scrubbed his hand through his hair. ‘Yeah, sorry bout that. I fell asleep. I’ll grab you a beer and go jump in the shower. Today was a sweaty one. I’m wrecked.’

Drew watched him step into the kitchen and open the fridge. He knew nothing about construction work, since he sat behind a desk all day in an air conditioned office. He could see it was extremely physically demanding though.

‘Thanks,’ he said, cracking open the tin Jay handed him. Jay swiped the beer he’d spilt on the sofa with his shirt and retreated into the bathroom. Ten minutes later, feeling like a new man, he emerged wearing just a pair of cargo shorts and sliders. As he entered the living room his brother looked him up and down with an odd expression.

‘Eat,’ he said, nodding at the pizza. ‘It’s good fucking pie man.’

Jay didn’t need to be asked twice. He took a great big slice dripping with cheese and flicked the TV on. ‘Wanna watch anything in particular?’

‘Nah. Just whatever.’

So Jay left the Bruce Willis movie on that was playing and hoisted his bare feet onto the coffee table. Once again he felt his brother’s gaze on him. ‘That construction job is sure making you ripped dude.’

Jay chuckled. ‘I guess.’

‘The chicks must dig it.’

Jay felt a pang of unease.

‘You got a girlfriend? Getting any action?’

His unease grew. ‘No. Nothing regular. I don’t really do hook ups. You know that. Not my scene.’

Drew knew all too well his brother was shy. He looked sheepish and started to pick at the price label on his beer. ‘Good pizza huh?’

Jay nodded and took another slice.

For the next couple of hours the conversation was easy going and both the pizza and Jay’s beer supply was decimated. By this point Bruce Willis had found all the bad guys and had finished them off, so Jay flicked the channels and found them a new movie.

‘I don’t know if you’ve noticed, but Georgia isn’t quite herself lately. I’m a bit worried about her,’ Drew piped up. Jay’s heart lurched.

‘Really? She seemed fine on Saturday.’

‘Yeah, I know. She’s good at putting a face on.’

‘Okay…’

Jay really didn’t want to be playing confidante to his brother about his wife.

‘I never mentioned it before, but we’ve been trying for a baby. It’s been three years now. She got pregnant once but it didn’t hold. She lost it. Nothing has happened since. So we both went and got tested. Apparently, my swimmers aren’t too enthusiastic and there aren’t many of them. Crazy I know, a stud like me.’

He gave a wry laugh that quickly faded. ‘Anyway, she’s sort of given up this year. She’s very low about it but hides it. I find her crying sometimes. She’s gone down two dress sizes from not eating. And now she just got news her sister Maggie is pregnant with twins. It’s eating her alive. And I don’t know what to do.’

He leaned forward resting his elbows on his knees. Jay almost felt sorry for him. But not quite.

‘Have you thought about that IVF business? Seems to work for some people.’

He couldn’t even believe he was saying this.

‘Yeah we have. It’s really expensive and to be honest with you, I’ve managed to rack us up a fair bit of debt over the years making stupid investments we couldn’t really afford. I think she’s mad at me about it but she never says. You know how she is.’

Jay nodded. Yep. He knew. She was meant to be his.

‘The other thing is. We don’t want some random donors baby. Hell, they could be anybody.’

Jay’s apprehension returned.

‘So that’s why I’m here. We wanted to ask if you’d maybe consider helping us.’

The pizza in Jay’s stomach fought to exit via his mouth. He jumped up off the sofa and went to the fridge. ‘Not sure I understand. Help you how?’

‘You got anything stronger than beer round here, cause I think we might need it.’

‘No I don’t Drew. I only have beer. Now tell me what’s up. Are you asking for a loan or something?’

Drew sighed. ‘I guess you could say that. But not money. Do you know what I’m saying?’

Jay wished he didn’t. He couldn’t think of anything to say. All he could think of was him and Drew camping in their late teens out in the Catskill Mountains and him spilling his guts to his older brother about how in love he was with Georgia and asking for advice on how to overcome his shyness and make a move. He felt stupid then and he sure as hell felt stupid now. So his older brother had basically been grooming him his past year to impregnate Georgia, the woman meant for him. He hadn’t really wanted to make amends at all. He hadn’t wanted to reconnect and repair the damage he’d done by stealing her. He just wanted his DNA.

‘Jay? I know this is a lot to take in. But you’re my flesh and blood. Family. And it would mean so much to Georgia.’

There. Jay had known he’d use that card. ‘It’s for Georgia.’

So he clearly knows I still care about her and that this could potentially fuck my head up royally. CHRIST he’s a prick!

‘And just how do you expect ‘this’ thing to happen? Are you seriously saying you want me to sleep with her? Your wife? Because that’s what it sounds like.’

Drew could see he was getting upset.

‘Look it would hopefully only be the one time. You don’t have to make a decision now. I’m sorry to put this on you. But I can’t do it for her. For us. You’re our only hope. You can make this happen. Make her dream come true.’

The emotions in Jay were like white water rapids. ‘Look, you’d better go now,’ he said. ‘I need some rest. It’s been a long day.’

Drew had clearly expected him to jump at the chance. That was even more distressing to Jay.

‘Sure. No worries. I’ll get out of your hair. Give you some time to think about things.’

‘The only thing I’ll be doing is getting some sleep. I’ve to be up at five.’

After Drew had gone, Jay stretched out on his bed. Sleep made a liar out of him by not showing up. All night his mind was consumed with their conversation and his brother’s request. How could he ask this of him? How could he even be ok with it? Then again, morals never were his strong suit. He’d basically swooped in and taken the love of his younger brother’s life the moment he knew how much he wanted her and loved her. It had taken him years to get over it and now in light of how he was responding to this proposition he was asking himself if he truly ever really had. But to be fair, he wasn’t sure he could do it even if he didn’t care so deeply for her. It was just weird.

The next day, work was a huge struggle. It was made worse by the fact that Tony had to leave work early as his girlfriend had gone into labour. Whilst picking up the slack, Jay overheard some of the men talking. From what they were saying he gathered that the baby wasn’t actually Tony’s. His girlfriend was a surrogate and apparently she’d done it several times before – for complete strangers. None of the men seemed to find it weird which set Jay to thinking perhaps he was not looking at things objectively when it came to Drew and Georgia.

Over the next few days, he considered it more deeply, researched it even. In the end, Georgia’s happiness won out.

When he got home Wednesday night he texted Drew.

I’ll do it.

Really?

Yeah. But just the once. And only because I know it’s so important to you guys.

The next minute his phone rang. It was Georgia.

‘Oh my God, thank you!’ she cried, clearly in tears. Drew had to take the phone off her.

‘She’s a little emotional right now. Yeah, honey, let me talk to him here, ok? Sorry bro. But thank you so much man. I can’t tell you how much this means. God this is great news.’

‘Well, I’d rather we didn’t talk about it too much. Just get it over and done with no offence, before I change my mind.’

‘Um, yeah. Totally. I’ll text you Georgia’s number and let you two work it out.’

‘Ok.’

‘Thanks again baby bro.’

As it turned out, Georgia had been tracking her cycles and she was due to be at peak fertility over the coming weekend, so it was arranged that she would go to Jay’s on Saturday evening while Drew was away on business in Brooklyn.

Jay had no idea what he was doing. Whether he should wine and dine her first like a date. Or just get straight to it. Whether he should dress up or just be casual. Aftershave or no aftershave. One thing he did do though was avoid wanking in the days prior. By the time Saturday rolled round he was busting. When he opened the door and discovered her standing there in a little floral mini sundress, no bra and strappy heels he felt his entire junk jolt to life in his pants.

‘Hi,’ she said, kind of girlishly. ‘Fancy meeting you here.’

He laughed awkwardly. ‘Come on in.’

‘Sit yourself down. Can I get you something, a wine cooler, a beer, tea, pepsi…?’

‘I’ll just take a water please. With ice if you have it.’

‘Coming right up.’

He clunked about in the kitchen while she fiddled with the cushions on the couch. He came in and handed her a glass and clinked his beer against it. ‘To success,’ he said.

She smiled. ‘Yes. To success.’

They sat in uneasy silence until Georgia once again thanked him profusely.

‘It’s ok. Look. I had some difficulty getting my head round it at first but I know how much you want this.’

‘So you really don’t mind? I know I’m probably not your type. And I should have really asked what you’d like me to wear.’

Jay swallowed. ‘Georgia. You look lovely. Better than lovely.’

She smiled sweetly over the top of her glass and took a timid sip. ‘So do you.’

Her eyes seemed to drop down to his broad chest and he realised she was admiring his physique. ‘Would you like me to sit beside you?’ he asked, sounding a little husky.

She nodded. He sat down close enough that his thighs touched hers. She could feel the heat seeping through the thin material. As they talked he noticed her eye contact increased and a gentle flush was beginning to build on her upper chest and throat. Georgia was feeling aroused. He remembered she was likely ovulating and that thought made his penis twitch and fill.

He set down his beer and took away her glass, using his big meaty hands to tuck a lock of hair behind her ear. ‘I don’t want that pretty smile hidden,’ he said, looking at her fulsome lips. She looked up at him through long lashes, her blue eyes beckoning. ‘We said we wouldn’t kiss,’ she murmured.

‘I know.’

‘But I want to,’ she whispered.

‘So do I.’

‘Then do it.’

He cupped her head and drifted his lips over hers, eliciting a sigh. Oh yes, she was definitely in heat. She leaned into him and he stroked his tongue just inside her mouth. ‘You’re a tease,’ she told him. He grinned and nibbled her neck and ear lobe, avoiding her parted lips. He wanted her begging for him by the time he took her. Dripping with want. The more aroused she was the better chance of conception apparently. Not that that was his only motive…

Her hand dropped to his rock hard thigh, which she squeezed unconsciously as he licked his way down her neck, kissing her clavicle, moving onto her lightly freckled shoulders. Her silken hair brushed his face and he inhaled the intoxicating scent of her. This was his woman tonight, as she should have been all along. He was going to be the one to fill her with virile seed that would travel up to her womb where it would bond with her ovum and make a son or daughter. It would be theirs biologically. Drew couldn’t take that away from him at least.

That thought fired him up to the point where he scooped her up and carried her possessively into the bedroom; she with one arm wrapped around his shoulders and the other caressing the broad expanse of his chest through his shirt. He set her gently on the bed and she looked around, a little taken aback. He’d gone to quite some lengths for a bachelor. There were lit fragranced candles by the bed and on the dressing table. He’d bottled water too, fresh linens on the bed and massage oils and tissues close to hand. The curtains were drawn and there was soft music coming from an Iphone.

Part 2 is available here totally free, no sign up needed.

https://samanthajwright.com/2022/10/31/undoing-the-shy-part-2/

Source: reddit.com/r/Erotica/comments/yj79ry/undoing_the_shy_a_cuckold_story