If you want to get into my britches you’re gonna have to show me more than those three inches…

Bob woke cuddling with Darlene. He’d had her twice more in the grass before they’d remounted their bikes and driven back to the trailhead. He couldn’t seem to get enough of her. Aside from the sex though it was the conversation that most captivated him. The two shared so much history, and regardless of it being so long in the past after finding their way beyond all the years that had gone by they found themselves sharing the same banter that they had as teenagers. It was easy to talk to her, and growing up together they each knew of the other’s foibles and failings and were able to look beyond them to find common ground together.

While the encounter in that shaded grove in the park had been all repressed passion and forbidden desires finally unleashed what followed in the bedroom could only be described as making love. They returned to a candlelit suite with soft music playing. Air Supply of all things, though it made a sort of sense; Darlene’s mother had introduced him to the band when he was about twelve.

Their lovemaking was unhurried, gentle but deliberate. Her ass felt like it was made to hold his dick, a velvet lined sheath for his iron hard erection that eagerly swallowed him up every time he penetrated her. Her expression as he thrust into her was a beautiful combination of agony and ecstasy, and as he plumbed her depths her little cockette jerked and leaked all over both of their bellies. When he finally withdrew, the sight of her gaping with cum dripping from her ass was almost enough to make him hard again.

In the morning with her head nestled against his chest and her legs entwined with his he felt at peace. If the next few days didn’t kill him, he was pretty sure he had the desire… no, the need to take care of and protect these girls… his girls… from whatever came along, even if he lacked the means to do so.

They settled on ‘See you later’ rather than goodbye, and Bob began his morning ritual. It no longer came as a surprise that the bedroom was redecorated or his clothes laid out following his shower. But… a Hawaiian shirt?

She stood outside the door, thinking through all her strategy and research, but well aware that no plan truly survives first contact with the enemy, and what was this if not war? She’d grilled the other girls as much as she could about Bob, found out everything they were willing to pass on about his likes and dislikes. All of them had been pretty forthcoming with their knowledge, but being drawn from such a variety of times through his life there were huge gaps in his background. Aside from some anecdotal information, the time between him leaving for college at nineteen and him starting at Highwood in his late thirties were a gigantic enigma, a total cypher. Almost two decades of only sparse information during which he’d moved a thousand miles away from home and been married and divorced twice.

That was why this date was a punt.

Go big or go home. And since there’s no going home…

Morgan raised her hand and knocked.

Maui. Of all the places she could have picked for the date, she chose Maui. Which was actually fine by him; ten years prior Bob had worked for an inventory company, leading a team of counters that specialized in Home Depot. His team mainly counted the Northern Midwest, but with their record for speed and accuracy, had also been selected to count Alaska, Hawaii, and Guam, the two former hosting seven stores apiece, and the latter one, so during a fourteen day business trip he’d visited six major cities across the archipelago. Kona had been his third favorite behind Hilo and Lihue. His one regret about the trip had been that the one day of downtime he’d had was in Hilo during the rainy season and not in Kona. That was because ever since reading Fluke by Christopher Moore he’d wanted to go whale watching in Lahaina Roads.

How she’d figured this out was a mystery, but what started off as an awkward first date quickly gained positive momentum when she’d clasped his hand while watching a humpback surface and clear its blowhole. The boat was crowded and although there were forty or so other people present, from that moment on, the world only contained the two of them.

She’d figured that Hawaii was a pretty safe bet for a date that could be anywhere and any when, but she didn’t want Oahu and the insanity of Waikiki or any of the tourist trap places, so in her own mercenary effort to be ‘genuine’ she’d chosen Maui in January. She’d been there before for a conference a few years back and had wanted to take a whale watching cruise but it had been off-season for the leviathans so she’d vowed to herself to return during one of the seasonal peaks which was how she’d landed at this date and place. What she hadn’t anticipated was that she’d actually enjoy spending time with Bob.

He’d come across as cynical and a bit of a smartass during her previous interactions with him but was still impressed with how well he’d anticipated her grandmother’s needs, yet here she saw a completely different side of him. His childlike wonder as he gazed out over the water touched her in a way she hadn’t expected and she found herself looking forward to the rest of the day.

During his previous trip he’d roomed with an older man who went by the nickname‘Chief’ due to his navy career. Chief was in his 70s back then and had traveled extensively as both a Naval CPO and later with the Coast Guard, and during those travels he’d found good places to eat just about everywhere, which was how Bob knew about the little Phò shop off of a side street near the King Kamehameha Mall. He had no idea what was in the noodle soup that was plunked down in front of them, only that it was delicious. Morgan had eyed it skeptically at first, but after a taste she had wolfed hers down with the same gusto that he had.

During the meal she fired off question after question about his past, which he was more than happy to answer for the most part, telling about most of the jobs he’d held through the years including the time he’d run away to join a carnival after dropping out of college. At one point he’d let slip that in his younger years he’d gone through a phase where he’d visit goth clubs dressed all in white, which had led to her disclosing her own goth phase, which in turn had resulted in him giving her an appraising look and determining that she’d look damn fine in that particular aesthetic. He said as much, causing a blush to rise in her cheeks.

That reaction brought on a torrent of flirtation between them as both bemoaned the decline of the subculture, which only continued after she dragged him to the da Playground where they spent the next couple hours grinding on each other to EDM.

The clash between the heat of Maui in the summer and the snow covered hills of the Chalet was never quite as evident as when the limo transformed into an open sleigh and pulled up to the front door past Bob’s jalopy which still sat there. Stúfur, the chauffeur, tonight wearing a red MAGA cap, grunted in a surly manner as the two walked into the front hall, which was empty tonight. Hand in hand they entered the elevator and that was when Bob, so far a total gentleman, looked at her and announced that he was going to kiss her.

Throughout the evening she’d vacillated on how she wanted the night to end, knowing that she’d be spending it in his suite one way or the other, but it wasn’t until their lips met that she finally decided in full what it was she wanted. Aside from her need to win this competition, she found that she genuinely liked Bob and she would only be lying to herself if she said that she didn’t find him attractive. He was the perfect mix of sensitive and cynical, funny and serious, smart without being overly preachy. And he kissed like fucking Don Juan.

“Take me to bed and fuck me til I can’t remember my name.”

(Title and outro: “If You Want Me To Love You” by The Asylum Street Spankers)