Another first for Dan
They woke to the sound of Dan’s phone ringing; Jake still snuggled into him – content from his first fuck.
“Shit, what time is it?” Dan asked, jumping up to grab his phone. He answered it and put his head in his hand as he said: “Yeah, yeah... sorry. I got talking to the boys and we didn’t realise the time. Where are you?”
Dan chatted to his wife for a couple of minutes before ending the call and flopping on the bed.
“Everything ok?” Jake asked, fearful that Dan was already regretting what had happened.
He looked at Jake and smiled, saying: “All good, little Woody. Luckily for us my wife can’t handle hangovers and spends the next day in bed. She’s not even out of the room yet so no drama.”
Jake reached for Dan’s hand and attempted, unsuccessfully, to pull the beefy stud on top of him. “But I don’t think we should push our luck,” Dan laughed, getting up from the bed and pulling his clothes on.
“Rach said she’d booked a lunch for everyone today, so we need to get our arses in gear.” He swooped down to give Jake a quick kiss before heading to the door.
”Keep hold of the key,” Dan said with a wink. “Hopefully you’ll need it again.”
Jake went back to his own room, feeling completely satisfied after finally being fucked by his hunky boss.
Despite this, as he got ready for lunch, Jake couldn’t stop the niggling thought in the back of his mind: he’d agreed with Dan that things between them would be casual and purely physical.
But even though he was trying his best to stick by the rules, there was no denying it – Jake was falling for Dan, fast and hard.
Deep down, he knew the situation between him and Dan could only end in tears. Dan and his wife may not have had the best relationship, but Jake knew him well enough by now to know he’d never walk out on their kids.
Deciding to simply enjoy it while it lasted, Jake headed out to meet his parents before lunch.
Making things even more complicated was the fact that Jake’s dad Rob had decided that he and Dan didn’t spend enough time together.
They’d been mates since school but had drifted in and out of touch over the years. But after taking their seats – with Jake and his parents next to Dan and Rachel – he heard Rob making plans with his secret lover.
“We need to get a round of golf in, buddy,” His dad told Dan. “And my Sunday league team needs a new player, if you’ve still got in you, old man!”
Dan laughed and replied: “Count me in for both, mate. But don’t complain when I show you up at footie. This old man can still kick a ball.”
After lunch everyone was ushered around the back of the main building to the dock, where three boats were waiting to take them out for the afternoon.
Unsurprisingly, Rob made sure his family stayed close to Dan and Rachel which made Jake desperate to feign sickness and head back to his room.
He also noticed that Dan was avoiding his eyes and once again had a sinking feeling the married man was regretting their morning fuck.
On the boat, Jake headed for the toilet to put some distance between him and Dan. As always, his boss looked incredible in a tight-fitting black Prada T-shirt, white shorts and some black slides. He topped off the look with a pair of Ray Ban Wayfarer sunglasses, looking so sexy Jake wanted to cry.
As he opened the bathroom door to leave, Jake was pushed back inside by Dan.
“What are you doing?” Jake asked, worried they’d be seen. Dan put a finger to Jake’s lip before quickly kissing him. “Relax, little Woody. We’re good.”
Jake knew Dan had sunk more than a few beers at lunch and suspected the booze was clouding his judgement.
“It’s driving me crazy being so close to you when I can’t touch you,” Dan said, rubbing his hands up and down Jake’s body.
Jake’s cock started to respond, and a quick glance down told him Dan was reacting the same way.
“Really? You haven’t even looked at me today,” Jake replied, hating how needy he sounded.
Dan put a hand on Jake’s chin, pulling it up so their eyes were locked. “Hey... I haven’t looked at you because if I do, I won’t be able to hide my boner!”
Jake softened at this, and his boss added: “After this, Rach will want to spend a couple of hours getting ready for tonight, so I’ll sneak away and meet you in the room,” Dan whispered.
Another quick kiss and Dan was gone, leaving Jake willing his boner to go down before he went to rejoin the party.
The boat trip ended with them disembarking on a small island where they were treated to a barbecue, before they headed back to get ready for the evening.
Rachel had been telling anybody who’d listen that she had booked a top DJ and live band for their last night, so Jake was actually looking forward to it – but he was unsurprisingly more excited about spending some time alone with Dan.
He’d only been in his room for five minutes when he got a text from Dan telling him he was on his way to their empty room.
Jake wasted no time in heading over there and was pleased to find Dan waiting on the bed, already naked. “Get your kit off and get on this dick,” Dan said, laughing and pointing at his throbbing member.
Jake didn’t need telling twice and soon he was naked and in between Dan’s legs, his mouth full of the stud’s huge uncut cock. Dan moaned and said: “Oh, baby... you know just what I like. Just like that... keep going.”
Feeling bold, Jake pushed Dan’s legs back until his hairy crack was visible. After sucking on his balls for a few minutes, he slowly worked his way down the married man’s taint until his tongue was on his hole.
“Fuck, little Woody. Nobody’s ever touched me there!” Dan shouted. But he didn’t stop Jake and instead started thrusting his arse towards the teen’s tongue, saying: “You’re a naughty fucker, go on... lick my hole.”
Spurred on by Dan’s obvious pleasure, Jake replaced his probing tongue with a finger – causing him to tense up. “Easy, baby. Don’t go getting any ideas...” he said slowly.
“Don’t worry, I won’t do anything you’re not comfortable with,” Jake replied, pushing his finger in further.
As Dan moaned and panted, Jake finally found what he was looking for and added some pressure.
“Oh fuck, what is that? What are you doing, little Woody?” Dan was thrusting harder now and moaning louder than ever.
Jake’s mouth was now back on Dan’s leaking dick, one hand working it up and down while the other focused on his arse.
“Fuck, baby. You’re driving me crazy, I’m coming!” Dan shouted. And with one final thrust, he unloaded down Jake’s throat.
Jake crawled up the bed to meet Dan for a kiss and whispered: “Happy birthday, sexy.”
Dan still looked slightly wide-eyed after having his arse played with for the first time.
After catching his breath, he chucked as he said: “Turning forty really isn’t as bad as I’d thought it would be...”
