A birthday to remember
It had been almost a month since Dan and Jake’s meeting and their decision to explore things together.
Four long weeks with only a couple of quick fumbles in the back of Dan’s van to keep Jake satisfied.
Each quicky like the last, some kissing and a blow job for Dan – but Jake wanted more.
He was desperate for his boss to be the first to fuck him. Obviously, it was going to hurt given Jake’s inexperience and the married man’s huge cock, but the teen was ready.
During one of their lunch time sessions in the van, Jake floated the subject to Dan.
As Dan was pulling up his work trousers, Jake said: “You know there’s much more we could try...”
Dan cocked an eyebrow, saying: “Such as?” Jake turned around and wiggled his arse, causing his boss to laugh. “You’re not serious, little Woody,” he said.
Jake quipped: “I’m very serious, Dan. Haven’t you ever thought about it? Don’t you want to know what it would feel like to slip your big, hard cock into my tight arse.”
This caused Dan to groan as he said: “Careful, Jake. I might need round two if you keep talking like that.”
As Jake persisted, Dan cut him off. “Course I’ve thought about it, you’ve got a lovely arse and you’re always sticking it in my face when you go up the ladder. I know you do that on purpose.”
Now it was Jake’s turn to laugh. “I wondered if you noticed that,” he said.
His boss continued: “But I also know it would be your first time and I’m not letting that happen in the back of this van. So if and when the situation presents itself and we manage to get some proper time together, we’ll talk about it then.”
Jake was touched. Dan was a proper man’s man – if you ignored their relationship – and he never expected the construction worker to be so thoughtful.
Clearly reading his mind, Dan scoffed: “Why are you surprised by that? I’m a nice bloke.”
Leaning in to kiss him, Jake said: “Fit as fuck as well as nice, your wife doesn’t know how lucky she is.”
Dan huffed, returning the kiss, before saying: “Try telling her that. Right, let’s get back before they start wondering where we are.”
***
Jake’s summer break from college was fast approaching and he’d been forced to take some time off work due to the amount of studying he had.
That meant hardly seeing Dan which was torture for the teen. Dan had managed to pick him up a few evenings where they’d driven to their usual spot for some quick fun, but Jake was starting to get frustrated.
It wasn’t a case of want anymore; he needed Dan to fuck him. He’d even managed to get the stud to finger him during one of their late-night encounters but Dan was sticking to his guns when it came to fucking in a car or a van.
One day Jake was walking through the door after college when he heard his mum on the phone.
“Rachel that sounds like so much fun, we’d love to come!” his mum sang. Jake froze, knowing the only Rachel they knew was Dan’s wife.
“We’re definitely free so count us in – how exciting, and I’ll make sure Rob and Jake don’t say a word to Dan.”
After she’d ended the call, Stella realised her son was in the room. “Hi love,” she started. “That was Dan’s wife, Rachel. She’s invited us to his surprise birthday weekend; it’s in two weeks so make sure you keep it free.
“It’s at a lovely estate and she’s hired out the whole thing. That will be fun, won’t it?” Jake slowly nodded but was lost for words.
How was he going to get through an entire weekend watching Dan play happy families with his ungrateful wife?
It would be complete torture but Jake knew his mum wouldn’t let him miss it now she’d agreed on his behalf.
He just hoped there’d be enough people there for him to avoid the (un)happy couple as much as possible.
***
The next two weeks passed in a blur. Jake and Dan hadn’t managed to get together but for once the teen was happy to not see his hunky boss.
There was no way he could’ve kept his mouth shut about the weekend surprise. Despite the less-than-ideal situation, Jake decided to bring a gift for Dan – hidden deep in his bag, of course – and dropped a lot of the money he’d been saving on a bottle of his favourite aftershave.
Jake also used his Polaroid camera to snap a cheeky photo of him bum, which he included in the card. It was playing with fire, he knew that, but he couldn’t resist trying to tempt Dan in any way possible.
Before Jake knew it, he and his parents were pulling into the seriously swanky estate. He knew Rachel didn’t work, instead staying at home to look after their kids, so he couldn’t help but laugh knowing Dan was unknowingly forking out a small fortune on his own birthday surprise.
They checked in, made their way down to the bar where the guests were drinking and mingling, waiting for the birthday boy.
Jake couldn’t help but think the fact Dan was turning 40 made him even sexier and he so wished they were celebrating alone.
Suddenly, Rachel called for quiet and said Dan was arriving. She’d lured him there thinking they were just having dinner.
So when he rounded the corner to shouts of surprise from everyone he knew, his face dropped.
Jake was worried that once he realised the teen was there, he’d be annoyed but, when Dan eventually locked eyes with him, he gave the most subtle of winks and flashed a cheeky grin.
Still, Jake made sure to keep his distance so as not to draw any suspicion. But he couldn’t take his eyes off of Dan.
Somehow, in the two weeks since they’d seen each other, he’d got even more handsome.
His brown hair was slightly longer on top but cropped close at the sides and he’d let his stubble grow out slightly.
Making the most of the warm weather, Dan was wearing a white shirt that was probably unbuttoned one too many – revealing a flash of his hairy chest.
He’d teamed it with a pair of grey trousers that showed off his big legs, nice bum and – as always – Dan had a sizeable bulge going on.
Jake wanted nothing more than to pull him away and get him out of his clothes, but he knew he needed to control himself.
Trying to keep busy he went to the bar to order a drink, but it wasn’t long before Dan appeared at his side. “Little Woody,” he sang, slapping Jake on the shoulder before letting his big hand drift slowly downwards.
“I didn’t expect any of this and I hate surprises,” Dan said. Lowering his voice and leaning in, he added: “But having you here makes it much more bearable.”
Jake could hide his huge grin – or stop his dick from instantly hardening. Dan looked down, noticing Jake’s swelling crotch, and whispered: “Easy there, little Woody. You need to learn to keep that under control.”
He was grinning and Jake flirted back: “Easier said than done with you hanging around looking like that.”
Dan leaned in closer and actually growled in Jake’s ear. “You make me feel so good,” he said. “I know it’s my birthday but I wouldn’t mind getting to unwrap you at some point this weekend.”
Jake looked up at him, wide-eyed. “Yeah?” The sexy married man replied: “I reckon we’ll be able to find some time to put one of these many rooms to good use, don’t you?”
With that, he gave Jake’s bum a quick squeeze before picking up his drinks and walking off – looking back to give a goofy grin.
It took Jake a few minutes to process what Dan had said. Did he really mean what the teen thought he did? Was he finally going to give Jake everything he wanted?
The first night was fine enough and passed in a haze of too much alcohol and Jake and Dan stealing glances at each other whenever possible.
Jake couldn’t help but notice how Dan’s wife was hardly by his side, instead choosing to sit with her friends all night.
He thought she was mad. If he was in her position, he’d never be able to get enough of the stud.
At around midnight, Jake decided to head to bed. As he was walking to his room he heard footsteps behind him and turned to see Dan jogging to catch him up.
Checking nobody was around, he leaned in to kiss Jake and said: “Meet me in room 308 at 7 in the morning.” He slipped a key card into Jake’s hand.
Jake must have looked confused, because Dan smiled and added: “A couple of our mates didn’t show. I’m paying for the room, why not use it?”
His face clearly said it all, as Dan told Jake – with a genuine apologetic tone – that he had to go. Turning back to him, Dan said: “Don’t forget to set an alarm!”
Jake laughed and went back to his room, filled with excitement about what would happen in the morning.
***
He got to the empty room a few minutes early, unable to wait any longer, to find a very hungover-looking Dan laying on the bed. Somehow though, he still looked as sexy as ever.
Dan groaned as he leaned up to pull Jake into him for a kiss. “My head is pounding; they wouldn’t let me go to bed until 4am.”
Jake laughed. “You poor thing,” he said. “You need me to take care of you?” Dan flashed a cheeky grin as he replied: “I was hoping we could take care of each other.”
Jake suddenly remembered the bag he was carrying with Dan’s present in it, taking it out to give to him. Dan looked genuinely touched and said: “You didn’t have to get me anything, little Woody.”
“Open the card first,” Jake said, desperate to see his reaction to the photo. Dan’s jaw hit the floor when the snap fell out of the card, he stared at it and said: “Tell me again why I’ve been turning this down for months?”
Jake gave a fake sigh and said: “You were trying to be a nice bloke. But nice is boring, it’s time to be naughty.”
Standing, Dan said: “I couldn’t agree more.”
This time everything was different. It had always been about Dan’s pleasure before – something Jake was more than happy with – but this time, the stud picked him up and carried him to the bed.
Dan removed his T-shirt, giving Jake a perfect view of his hairy body, and stepped out of his shorts, revealing that he was going commando.
Jake reached out for Dan’s cock, but he pushed his hand away. “Not this time, baby.” The teen’s dick jerked. Hearing Dan call him “baby” sent him wild and he let the birthday boy take control.
After removing Jake’s clothes through kisses, Dan lay on the bed and pulled him on top. He reached over to the drawer of the bedside cabinet and pulled out a small bottle of lube.
“Are you sure about this?” Dan whispered. Jake just leant in for another kiss to answer the silly question.
As they kissed, Dan lubed up his fingers, gently sliding one into Jake’s hole. After the initial sting, Jake couldn’t believe how good it felt and pushed down when Dan went to insert another.
Although he’d never been with a man before, it was clearly not Dan’s first time as he expertly explored Jake, causing the teen to moan uncontrollably.
“Yeah... you like that, baby?” Dan asked. All Jake could do was nod and whimper as a third finger entered his hole. “You ready for the real thing, little Woody?” Dan questioned seductively.
This time Jake found his words and cried: “Yes, fuck me, please.” Dan growled, pulling his fingers out and lining his thick, leaking uncut cock up with Jake’s hole.
“Here it comes, baby,” he said, as he eased the first couple of inches in. Jake wanted to scream the pain was so intense.
But Dan stopped to let him get used to it, and it wasn’t long before pleasure replaced the pain.
“Go at your pace, little Woody. We’ve got time,” Dan said as he ran his hands up and down Jake’s body.
Jake started pushing down on Dan’s girthy eight incher, before slowly pulling up again – stopping just before it came out. Dan moaned as Jake repeated this a few times before, feeling brave, attempted to take more of his cock.
Eventually he managed to get it all in, feeling Dan’s bushy pubes tickling his own balls. Dan looked like he was going to come there and then, letting out a growl before saying: “You took it all, baby.”
Feeling more turned on than he’d ever been in his life, Jake started to ride his sexy, married boss.
He picked up the pace and soon enough they were both panting wildly. Dan stopped him and for a brief minute Jake worried he was having second thoughts.
But he simply looked at him with a devilish grin and said: “Now I’m going to show you what I can do...”
Jake squealed as Dan flipped him over, so he was now on top. “You ready to get fucked, baby?”
Without waiting for an answer, Dan pulled out before slamming back into Jake’s hole. They both moaned as the stud pounded his teenage lover, sweat now pouring from him onto Jake’s body.
Jake had his legs wrapped around Dan’s waist and was screaming in pleasure while Dan’s moans were getting steadily louder.
“Fuck... so tight baby... I’m getting close. Where do you want it?” Dan managed with a growl. “Come in me, Dan. Fill me up, please,” Jake almost screamed.
Flashing a toothy smile, Dan quipped: “Whatever you say, baby.”
Then Dan did something unexpected, taking Jake’s cock in his hand as he slowly wanked it.
“I want us to come together, little Woody,” he said. “Fuck, Dan... I’m close,” Jake moaned. “Let it go, baby,” Dan replied.
Suddenly Jake started shooting ropes of come over his own stomach as Dan let out a loud growl before unloading inside of him.
As they both came down from their orgasms, Dan flopped down next to Jake and pulled him in close, with the teen resting his head on his chest.
“This might be the best birthday I’ve ever had,” Dan said, leaning in to kiss Jake with more passion than ever.
