“Gentlemen do not sail to windward.”
Well, if “gentlemen” are anything like the ass that said that to me inn Hope Town, to windward I go.
To Barbados, in fact. As far from the “gentlemen” who haunt the cursing grounds of the Western Caribbean. Far from the tourists in The Bahamas, the ex-pat yacht clubbers in the BVIs and the trendsetters in the Turks and Caicos. TO Barbados and the most amazing surf on the East Coast of the Northern Hemisphere.
So to windward I go. Pick a weather window, get on that port tack and enjoy the ride.
I left a week ago. Awaiting me on arrival was an email from by best friend and occasional lover, Kylie. Married now, which is weird. And she wants to visit. A bit more weird. And she wants to bring her husband. Which is really fucking weird.
Not really comfortable with the whole thing, I took my usual approach when faced with something I didn’t want to deal with. I acquiesce.
“Sure!” I wrote back. “I would love to see you and finally meet Jack.”
Jesus. What was I thinking. Kyle’s sudden marriage was one of the reasons I headed south. I was finally getting my head wrapped around that fact. And really enjoying my solo surf safari through the Caribbean.
Her reply came immediately. “Awesome. But where exactly are you?”
“Barbados,” I responded. “Just arrived.”
My phone dinged a minute later. “Shit Clay. Flights are expensive. But we will be there on Tuesday.”
Damn, 4 days. Four days to get my head right. I checked the surf report…moderate swell. So at least there was that.
I hitchhiked into town to pick them up Tuesday afternoon. I stared through the chain link fence at the tarmac and watched the passengers as they left the small jet. And there she was, gorgeous as ever. Tan as always, blond hair pulled back, And following close behind, I assumed, was Jack.
Well, fuck. What a stud. I mean, like head turning, model like stud. Ok Kylie, I’ll give you a forever hall pass on this. Not that I would or even could.
We gathered their gear, including a couple of boards that apparently survived baggage handling, grabbed a taxi and headed to the marina.
“I figure we can spend tonight in town, get up early tomorrow and sail to a nice little back break. There is a protected cove we can anchor, spend a few days. The break is not too far… maybe a 15 minute paddle,” I said, raising my voice to be heard above the wind whistling through the open van windows.
“Sounds good Clay… Can’t thank you enough for having us,” Kylie said.
“Yeah, dude… We really appreciate it. I know it must be weird having me around.”
“No worries, Jack. I’m getting used to the idea. And I figured if Kylie loves you enough to marry you, you are ok in my book.”
He smiled a bit as Kylie squeezed his knee. We rode the rest of the way in silence, me staring out at the beautiful coast as the sun began to set.
Maybe this won’t be as wigged out as I thought.
After some espresso and toast the next morning, we headed out. Nice breeze, maybe 10 knots, and in the right direction. After motoring out of the channel, we set the sails and enjoyed a nice sail to the cove.
We set the anchor, had a bit of lunch and then jumped in the cool Caribbean water and paddled around the point to the break. Not much of a swell, so no one was out. We bobbed at the take off for a bit. Damn, Kylie looked so fucking hot in her board shorts and bikini top. And, fuck, Jack looked amazing, too. I took a dip in that pool once or twice back in college, after a few two many beers, but never thought of myself as “gay” or “bi”. Maybe just an opportunist.
We caught a few waves, Jack and Kylie a little rusty at first but definitely holding their own as the afternoon wore on. The swell faded as the sun began to set and an onshore breeze flattened out what was left. We paddled back to the boat, recalling the rides we caught and like all surfers, made outlandish claims about wave size and our extraordinary ability to tame the sea.
I got back to the boat first and packed up a cooler bag with some food, a few beers and a bottle of the local favorite, Mount Gay rum. Jack and Kylie arrived soon after.
“Hey… there is nice little beach in the cove here. I figured we could drop the dinghy and have a bonfire and dinner.”
“Sounds perfect,” Kylie said, drying off her hair. “Let me pack up a few things and get into some dry clothes. She and Jack disappeared into the guest stateroom as I went on deck to lower the dinghy.
Kylie and Jack came out on deck and jumped into the dingy as I started the outboard. We headed into the beach, the sun almost set behind us. We pulled the dingy on the the beach and started hunting around for driftwood. We soon has a nice little bonfire going. I got out the beers and the run and set up a grill over the fire.
We quickly downed the beers, thirsty after a day in the sun and water. I cracked open the rum and passed around the bottle as I flipped burgers for dinner. Afterwards, We sat silently watching the sun fade into the ocean silhouetting the sailboat.
“Wow,” Jack said. “I see why you do this dude.”
“For sure,” Kylie said.
Magic permeates the time just after sunset in the Caribbean and tonight was no different; we sat quietly, lost in our own thoughts.
I was thinking philosophically, as one does at such moments, when I felt a gentle kiss from Kylie, familiar and strange at the same time, as she parted my lips with her tongue and whispered, “I’ve missed you.”
“God… I miss you too,” lost in her and the memories, responding to her kiss. I hadn’t exactly forgotten about Jack but just leaned in. An opportunist again, I suppose.
I felt a hand creep up my thigh as we kissed. Doing a quick bit of geometry and anatomy in my head, I realized it was Jack, not Kylie. I opened my eyes to watch him kiss her breast through the thin gauze of her sundress as his hands worked towards my swelling crotch, staring now at the board shorts.
Well, I thought this visit was going to be weird, but this just felt right. Maybe it was the rum, maybe it was the magic of the day, maybe it was everything.
I moved my head down to Kylie’s other breast and began to kiss and lick her as she moved the shoulder strap down her arm. She stood up to remove her dress and Jack and I looked at each other, his deep blue eyes peering into me.
I couldn’t resist; I ran my hands through his thick hair as I pulled him towards me, kissing him deeply, feeling his beard stubble on my own. We kissed frantically, tongues dancing, breathing heavily into each other. Kylie stood over us her hands rubbing her pussy gently.
“Ob my god, this is so hot,” she said, falling to her knees between us. She untied Jack’s board shorts and wiggled them off. She turned to my shorts as Jack and I continued our passionate kissing.
We were both rock hard now and our cocks rubbed against each other as Kyle began to lick us both. This was almost too much and we both moaned deeply into each other. I felt my hips start to grind against him as my hand gripped his firm ass. I pulled him against me as I thrusted hard.
Jack pulled away and began to kiss my neck as he moved to my chest, sucking my nipples as he played his tongue over them. Kylie was throating me deeply, I felt her own excitement building, coming from deep within her and channeled into my cock. Jack’s mouth joined hers soon as I leaned back in enduring ecstasy. Jack and Kyle began to kiss each other, my cock in the middle. The pulled away slightly, lost in their own passion. I watched, glowing now as I began to stroke my own cock in rhythm with their kissing and movements. Jack went down on Kylie as I moved to kiss her, our tongues meeting and teasing like so many times before. Her breathing quickens as Jack brought her to the edge. He stopped, kneeled before her now, stroking his cock and lay down on her, easily entering her wet pussy. She came almost immediately, as her ecstatic sighing evolved into a guttural scream. Jack slowed his thrusts slightly but still worked Kylie, his own orgasm building. He slowed and then stopped as he came to the edge.
I was laying back now, gently stroking myself. Jack moved between my legs as Kylie brought out some lube. I didn’t know if I should be pissed, because bringing lube meant they planned this whole adventure. But I was too hot and too fucking turned on to really care.
Kylie lubed me ass, and rubbed lube on my cock and balls. Jack brought his cock to the rim as Kylie squirted it with lube. He pushed in gently. I have played with my ass and enjoy the hell out of it, but this was a first. My ass strained at first, but I soon relaxed as Jack pushed further in. I felt his cock rub by prostate as Kylie began to suck me and play with Jack’s own ass. I shivered uncontrollably as Jack’s throbbing dick massage my prostrate. Kylie pulled away from me as my cock throbbed. I felt an orgasm building, but this was unlike anything before. It rose pulling itself from my core, my very soul shooting hot liquid on to my chest as my throat exploded into a primal scream. I convulsed widely, uncontrollably, my mind and body no longer mine.
Jack’s pace increased as he watched me cum and Kylie rose to kiss him and pull him into me as she fingered his ass. Jack’s orgasm build, almost as strong as mine and Kylie thrust her fingers deep into him.
I was still had, still turned on still wanted more as Jack’s cum poured into me. Kylie pulled away from Jack and straddled my face in 69 as she began to suck me. I could not get enough of her, her wet pussy, her essence… reveling in its rich musky odor. My tongue flitted from her clit then deep within her pussy lips and back again. I brought my head up slightly to reach her ass and rimmed her as she fell heavily on my cock.
I caught sight of Jack out of the corner of my eye, his cock still hard. He stoked himself, wiped it clean and came up over me and pushed into Kylie. I wasn’t quite prepared for that but began to kiss them both, my tongue reaching out to lick his balls and back to Kylie’s clit and gorgeous pussy. He thrust harder now, as the three of us built to another orgasm. Jack came first holding his cock deep into Kylie. Feeling his balls quiver in my moth shot me over the edge and Kyle reeled back, pushing her pussy, wet with her juices and Jack’s into my face.
Holy crap, I thought to myself, wow, just wow.
We untangled and lay together on the beach blanket, glowing from the moment. I leaned up reached for the rum, almost too exhausted to do that.
“Same plan tomorrow?” Kylie said, smiling.
“Yes, yes indeed.” Jack and I said in unison as I took a swig of rum and passed the bottle down.