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Chapter 4: Sunset Sail
Much to my surprise Ian just watches and strokes his own cock as I anxiously await his next move still on my knees as a bead of precum drips from my locked cock and Brendan is still on the bed floating in euphoria. Ian gets himself close and then steps up to my mouth and shoots his load in my mouth without me getting much time to really suck on him until he's done and orders me to clean up his cock which I gladly do swallowing all the cum I can get but I can only enjoy it so much since he pulled his cock away quickly to rush to the locker I just spent forever organizing. He rummages around a bit and then picks out 3 matching pride striped swim briefs and throws one at Brendan on the bed, one at me, and starts to pull his own on saying: "Get dressed! It's about time we take our guest out for a sail!"
Another bead of cum started dripping from my caged cock as I got excited at all the thoughts running through my head: First of all just spending more time with theses amazingly hot guys in these small super gay speedos, finally getting to sail the new boat for the first time since we owned it, and Ian as always said it all with that mischievous smirk that he has some more super sexy things in mind for us to get up to while we're out sailing. My ass was twitching at the possibility of getting fucked while out sailing and who knows what else he had in mind!
I jump up from my knees and slip on the speedo adjusting my caged junk to be comfy as I keep dripping pre cum that already starts to show through that Ian notices and comes up to embrace me with a kiss and whispers in my ear:
"Don't worry, I'll make sure you get to drain your balls once we're out sailing. Now go get everything ready to go, I'll get Brendan dressed and on deck to help toss lines then make us a snack and set things up for round two."
He gave me a teasing yet forceful spank on my ass before moving out of the embrace and then before I could walk out of the cabin to get to work, I feel another tugging on the back of my speedo. Ian has a butt plug in his hand -- a metal one with a decorative fake jewel to sit between your ass cheeks. He tucks the back of my speedo under my bubble butt and finishes lubing up the plug as I know what's coming and start to bend over as Ian uses the slightly cool metal to tease my butt with a few circles to lube it up before going in. He obviously wasn't feeling very patient today because he went all in right away. My hole tightened quickly again around the small base and I could tell I was taking a slight moment to enjoy the sight before quickly pulling the back of my speedo up to cover my ass and then gave me a good spank making sure to hit the outside of the plug to send a jolt up my insides making me even more ready to take his cock or Brendan's or both.
Speaking of- Brendan had propped himself up on the bed to watch the bit of a show while flexing his abs just about making me drool again from both my mouth and my dicklet. Watching as the plug went in my ass I could see his cock twitch and knew that the speedo he was about to put on would not hide his dick at all that wasn't going to be fully relaxed anytime soon.
I walk out of the forward cabin leaving Ian to finish cleaning up and getting Brendan's cock stuffed into that speedo and go to get the engine fired up, shore power disconnected, and lines ready to sail. I'm no stranger to butt plugs but this time still felt different. Every step was driving me crazy- the wet spot in the front of my speedo was growing quickly. At this rate I didn't know if there would be any cum left for them to fuck out of me by the time we got out of the harbor.
A few minutes later, I was back in the pilot house at the helm as Brendan came up the companionway speedo clad looking sexy as fuck and with a noticeably greater amount of confidence from the shy delivery boy that appeared on the dock a mere few hours ago. I look down at his bulge just as he had been starting at mine earlier on the dock when we first met. The attention made him stir as he was looking at my bulge again as well. Then he reached down to grope my bulge as he leaned in for a kiss as well that made me strain in my cage and the grip of his hands and his bulge grow as well.
I broke away from the kiss as we both smiled and Ian came up the campion way as well grinning at the sight of us getting along so well.
"Ok- let's get going so we can keep playing once we're out there in private!" I announced to everyone.
"So how long are we going to be out sailing?" Brendan questioned.
"As long as you want- got anywhere to be?" I replied
"Nope"
"Then let's make this really fun and anchor out overnight. We can find a nice secluded spot all to ourselves."
"Those were my thoughts exactly" Ian chimed in with a wink to both Brendan and I.
"Now that we're all agreed let's get those dock lines off and get the fuck out of here. Tides going out so go ahead and drop everything but the starboard forward spring." I instructed my `crew'.
Ian exited the pilothouse to the starboard deck, Brendan looked confused. I couldn't tell if he was confused by the slut boy taking charge or the boating directions.
"When it comes to the boat and sailing, I call the shots," Part of his confusion went away. "And Starboard is right, Port is left, bow is the front, stern is the back, you'll pick everything else up as we go," I said with a smile as I could see more things connecting in Brendan's mind.
By the time I got done explaining that though, Ian had already tossed everything on the port side too except for the stern lines. So, I directed Brendan there as Ian went back to the one spring line left. Once the stern was free, I put the boat in gear as Ian took in the spring and we were off on our first adventure.
Ian instructed Brendan on coiling and stowing the dock lines and fenders as I piloted us out of the cramped marina and through the channels of Biscayne Bay out to the ocean. It was now late afternoon with a nice moderate warm sea breeze and calm seas out in the ocean, a great first cruise to take down the keys that make up Biscayne National park.
Once done with the cleanup they came back through the pilot house. "How much longer until we get sailing? Enough time to get snacks ready?" Ian asked me.
"Ehh probably about 20 minutes before we turn the corner and aren't going right into the wind."
"Great," and with that Ian disappeared below.
I felt Brendan's presence behind me in the helm chair and then his hands on my shoulders as his strong hands started to give me a bit of a should rub.
"Thanks that feels so good Sexy. Are you enjoying yourself?" I asked him turning my head slightly back to try to look at his sexy body again.
"Oh most definitely, I'm glad I did call and come back. I wasn't sure at first but after that blowjob and watching you get that plug up your ass and the speedos. Like I've always been kinda interested in guys but also had some girlfriends I've enjoyed sex with, but I know I've enjoyed your and Ian's kisses and your blow job better and I can only imagine that fucking your hot ass later is going to be so much better. Not to mention, I've always loved the beach and seen boats out there always wishing I could be on one so I get this chance too!"
"Well good! I'm glad we could help you get the experiences you have always wanted. Anything else you want to try with a couple of guys other than fucking me?"
"I don't know? I've never really thought about it but I'm already trying new things and enjoying it so far so might as well try it all. What other things are there to try?"
"Glad you're being open minded- Ian and I get up to a lot of kinky things who knows what he has in mind next but now that we have the boat and private anchorage, it opens up a lot of possibilities that make me strain in my cage even more just thinking about them!"
"You seem to be straining in your cage a lot there" Brendan laughed as he looked down at my speedo and the now massive precum spot. "Doesn't it hurt?"
"Yes, yes I am straining a lot. It kinda hurts but in a fun way if that makes sense? Like yeah it's frustrating and sometimes really makes my balls ache but the benefits when living with Ian definitely outweigh the discomfort."
"And what are those benefits?"
"Well to start with, he's horny all the time so this ensures I'm always horny too! And he can last forever when he wants to for both oral and fucking me, so when I'm locked up I can last as long as he does otherwise I would cum and be done long before him. This way I can focus on his cock and his pleasure not playing with my own. It also makes me focus on all the other pleasure centers of my body and can like give me a full body orgasm that can feel so good without getting hard and makes me cum multiple times without feeling relief. Anther wonderfully frustrating feeling -- like Ian can fuck me and I cum 5 times before he cums and I'll still want more dick!"
"Wow, you are such a slut!" Brendan laughed and I joined him laughing. "But that sounds awesome, I mean I totally love my boners and want to fuck you, but maybe at some point I'll try having my ass played with and maybe even locking up. Not ruling it out, but not committing either."
"Totally fine- we're all about exploring and trying new things- never limit yourself based on labels. I mean even once in a while; Ian unlocks me and lets me fuck him. I'm always so horny and my cock so sensitive that I don't last long, but he can't take it for long either so it works out! And yes, yes I really am such a slut thinking about dicks and having them put in me every chance possible!"
"Well I hope I can learn to be so open about sex and my desires like you two,"
"Hang around us long enough and you will!" Brendan then finishes up my shoulder rub by kissing my neck up to my cheek and then to my lips.
Ian appeared again from the galley carrying up the snacks he tossed together before disappearing again to grab the drinks. When he got back he distributed the martini's and proposed a toast: "to new friends, hard cocks, and lots of cum!" we all laughed as we clinked glasses and took a drink.
"Perfect timing, we're just getting to the end of the channel so we can start pulling the sails out," I commented as Brendan was already digging into the snacks.
"Great, Brendan come with me and we'll get the main up," Ian instructed pulling Brendan away with a mouth full of crackers.
It was great watching those two studs in nothing but their matching speedos in front of me hauling the halyard up showing off all their muscles and not even breaking a sweat. I was so looking forward to tonight. I wasn't exactly sure what Ian was going to do to me, but we had talked for so long about wanting a sailboat so he would have the means to tie me up on deck and all the possibilities that followed.
I was snapped out of my lustful daze by the main sail flapping in the breeze and Ian yelling back that he was ready for me to fall off the breeze- so I did as I set our course south onto a port beam reach. Once we were on the right course, Ian and Brendan came back to the genoa sheet and started pulling tension so that I could start unfurling the sail. Once it was out and trimmed, I pulled the throttle back into neutral and shut off the engine as my two studs returned to their drinks and snacks now with only the sound of the wind flowing through the pilot house with all the doors and windows open, the water on the hull, and the sight of the sun starting to set lighting the backs of our sails with a warm orange glow.
"Wow, it's so quiet now" Brendan commented in astonishment.
"That's the magic of sailing" I responded with a smile as Brendan came back up to my side at the helm. "Do you want to drive?" I asked him.
"I don't know what I'm doing but sure!" He responded as I motioned for him to take the wheel and I stepped back behind him with my hand on his on the wheel.
"So nice and gentle, you're feeling for the groove where the boat wants to sail itself," I said in a sensual way as I kept my hand on his and my cage rubbed against the side of his butt only separated by two thin layers of material. I stayed there another minute as he got the hang of it. "There you go, you've got it now- you're like a natural!"
He smiled even as I let go of his hand and moved away from him to check the charts and navigation as Ian came looking over my shoulder while his hands were caressing my ass and sending a wave of sexual energy through my body.
"How far are you planning on going?" He asked.
"I was thinking anchor here for the night and then we can figure the rest out tomorrow." I said pointing at the spot on the chart. "Should be about another hour at this rate. That'll get us anchored before dark and then we can either play and then do dinner, or dinner first."
"Or play, then dinner, then play more.." Ian added.
"I like that plan; I just hope I can keep up with your sexual appetite!" Brendan chimed in laughing.
"You know I'm always up for play time. Keep sailing this direction and don't hit anything, I'll go below and get things prepped for dinner so we can cook whenever we are ready. Anyone need anything else?" I inquired showing my submissive side again. "Yeah first, now that we're out to sea, I need everyone to strip out of your speedos, we're all naked from here on out. Secondly, I need to pee so drink up Trevor." Ian commanded to the boat.
I wasn't objecting so I turned to make sure I would show off my plugged ass to the two horny studs behind me as I bent over to strip off my speedo. When I turned around the other two were still staring at me as they just pulled their speedos below their hips and let them drop down their legs exposing their mostly hard cocks also starting to glisten with precum.
I stepped back in front of Ian and got on my knees and rested his cockhead on my tongue. His cock was barely in my mouth as he started pissing his recycled martini into my mouth and I lapped it up. Brendan was swapping between looking out the windscreen driving the boat and looking back at me drinking Ian's piss again, but this time without the gag, just straight from the tap. Ian finished up pretty quickly and I as always closed my lips around his dick to make sure I got every last drop and teased him just enough to make sure I left him rock hard before I went blow.
When I was finished with Ian, I turned to Brendan: "Do you need to piss too while I'm here?"
He was reverting back into his shell still getting used to this type of kinky play but ended up nodding slightly. I went over to the helm and helped position him so that he could still sail the boat while I drank his load. I put his cockhead on my tongue just like I did with Ian, but Brendan was still a bit pee shy -- at least while his dick was in someone else's mouth.
"Just relax, take a deep breath and let it flow out your dick. He's ready to drink it up," Ian reassured Brendan that worked as he let out is piss into my mouth and I drank it up trying not to leak too much precum onto the floor.
I finished him off the same way I did Ian- teasing making sure he wanted more but making him wait just like I had to. I checked that we were on course again before going below to prep dinner and make sure that Ian had time to talk with Brendan about tonight's sex plans as well and see if he can extract any other deep fantasies.
The galley work went pretty quickly- just making sure we had some things seasoned up ready to throw on the grill- Steaks, potatoes, veggies- simple, yet delicious then headed back up to triple check we had everything already hooked up on the grill as well- thankfully we did! As I walked through the pilothouse past the other two, they were definitely in bro mode talking sports and this and that other BSing that I'm horrible at. Their cocks were mostly deflated again but not completely soft- particularly as I could see both sets of eyes wondering eyeing up both my cage and ass looking for that plug that was still keeping me on edge the whole time.
Before we knew it we were at the anchorage and it was time to fire up the engine again and douse the sails. I took the helm back as Brendan followed Ian around the boat and helped him furl the genoa first and then lower and flake the mainsail as I maneuvered the boat into the shallow water of the key. Thankfully as I expected we had the place to ourselves besides the wildlife. It was hard to pay attention to exactly what I was doing and deciding where to drop anchor with the two completely naked studs in front of me on the boat with their dicks hanging there making my mouth water and plugged ass quiver with what I knew was to come soon.
We finally get the boat in the right spot and I yell forward to drop the anchor, then we make sure it's set before powering down the engine. As I'm starting my anchorage to do list, I heard a splash and look up to see only Brendan left on the boat but on the side about to jump in and think- well guess Ian already went swimming. So I hurry with the rest of my list- making sure the anchor light is on, drift alarm and AIS are set, and generator functioning. Then I rush out to join in the hijinks as both them are already back up on the boat getting ready to jump in again.
A few more dives in the water by each of us and some fondling each other both in and out of the water and we were all hard and horny and ready to move onto the next portion of the evening. I in particular was ready to replace the but plug with a real dick- at least one. So we swam around the stern of the boat and climbed up onto the swim platform and used the shower to wash the salt off each other with plenty of hands all over each other with the excuse that we're just washing each other's naked bodies off. If anyone else was around, it would've been quite the show to see, but it was just us and the wildlife.
The sun was just about set now as we toweled dry on the aft deck and the glow of the cabin lights spread around the boat on the water.
"You two go up by the mast, I'm going to grab a few things and then meet you up there." Ian instructed us. Now that we're safely at anchor, I was back to the subordinate just following Ian's every instruction, so Brendan and I made our way up there and sat down on the deck admiring the sunset and beautiful surroundings. We shared a sensual moment waiting for Ian to join us with whatever he had up his sleeve.
A few minutes later as I was resting my head on Brendan's shoulder while still admiring the beauty and quiet of the surroundings Ian joined us with a bag of toys gathered from down below and sits on the other side of me to join in the quiet romantic moment before diving into what I was now sure would be an intense session. Ian puts his hand on the back of my neck and gently guides my head off Brendan's shoulder to his waiting lips as we start making out. As we are still making out Ian's hands start exploring my body and encourage both Brendan and my hands to explore all 3 bodies as well as Ian and I break lips for a moment to bring Brendan into the kissing as well and the sexual energy builds between the 3 of us. We keep going as hands are all over teasing everyone's cocks and asses, and we all swap off making out with each other after proving once again with laughter that 3 way kisses usually just end up in hitting heads!
Finally as the dusk was giving way to the light of the moon reflecting off the water and bathing the boat in plenty of light to still admire the form of all of our bodies, Ian silently guided me onto all fours with my ass facing him and Brendan as they both caressed my ass and played with the plug as I moaned in delight and leaked more precum onto the deck. Soon hands gave way to lips as Ian demonstrated his amazing rimming technique even while plugged and soon hand Brendan following and after a few minutes practice and guidance from Ian, he was just as good. I looked back under my legs as Brendan was working my ass to see Ian working Brendan's cock with this hands getting him nice and hard for his first time fucking a guy in the ass.
Soon the lips gave way to hands again as they started to pull the plug out. So much unlike how he put it in, Ian took his time teasing it in and out while slowly making progress towards removing it until it was finally out and for a moment my ass felt disappointingly empty after the hours I spent with it pressing against my prostate. But that meant that now it was free to be filled with the big juicy cocks of the hunks playing with my ass.
But first Ian made sure to tease me more with more rimming from both him and Brendan. It felt even more amazing getting rimmed without the plug in when they can really get into my hole. Brendan much to my surprise was really getting into it with such good feelings at my hole opening while Ian was making out with me again at the other end still with the taste of my ass on his breath, I was in heaven.
"Ok that was amazing, but now I'm so ready to fuck you," Brendan finally broke the audible pattern of moans and kisses.
"And I'm ready for you," I responded as Ian reached for the lube and made sure both Brendan's dick and my ass were adequately lubed up and then helped line everything up as Brendan slowly slid his thick juicy cock into my waiting ass.
He let out a big moan in ecstasy as he felt the tight warmth of my ass for the first time sliding in slowly all the way to his balls and then held there leaning over me in somewhat of an embrace as my ass tingled and I gave him a few squeezes and wiggles that made him twitch. Ian then moved to the other side of me to feed me his cock as he made out with Brendan in between coaching commands on how to get the most out of fucking my ass.
Soon they both picked up the pace and I was loving getting fucked in both ends at the same time by massive cocks attached to the hottest guys around in the moonlight on the deck of our boat. I had what felt like an endless series of mini orgasms as they worked me over. I didn't want it to stop but then Ian pulled out and commanded Brendan to swap places with him so I now had Ian's dick in my ass and Brendan's cock down my throat to send me on my next stream of mini orgasms making quite the puddle under me particularly now that I had the tase of my ass on Brendan's dick in my mouth. They kept going and going on me all of us enjoying every moment of it. They pounded harder and harder and I could sense their climax coming soon but Ian had other plans.
Just as I could almost taste their cum in my mouth and ass, they both pull out completely and quickly leaving me feeling so empty once again. I held in my place on all fours on the deck of the boat shivering from all the wonderful feelings I just had that were now gone. I looked up to see Ian digging into the bag he had brought up- he pulled out some rope and his still throbbing hard cock led his way back to me when he commanded me to my feet with my hands out towards him. I leapt to my feet and complied as he tied my wrists together and led me to the mast. He tied the extra line into a loop and attached the halyard to it and started hauling it until my arms are all the way up above my head and then I go up onto my toes as he ties it off there and I'm left hanging by my wrists on the mast in only my chastity cage with Ian and Brendan looking at me with matching mischievous smiles and raging hard cocks pointing at me and balls full of cum ready to burst all over me.
"So Brendan and I were talking and he already got his dick in your ass but said he also wanted to tie a guy up and give him a little torture before fully getting off. So you're going to be our good little slut and take whatever he wants as long as he wants. Got it?"
"Yes sirs, please use me as you like" I said as I stared into their eyes turned on by the control they had over me and the lust in their eyes that they were about to take out on me.
First thing Brendan grabbed was the butt plug that he reinserted into my ass while giving my balls and cage a squeeze and then slapping my ass and then gave me a face full of spit "you're my slut boy now" before spinning my face towards the mast so my ass was out towards them and I could hear them whispering and passing something else between them. Next thing I know one of them puts a blindfold over my eyes and ties it down as the rest of my senses start to heighten as well and I feel both of their presence behind me and then I get a swift firm smack across my ass -- too big to be a hand, must be the paddle. And again I get the paddle across the ass this time hitting the plug in a way the sends a jolt through my body and I let out an audible gasp of surprise, sting, and pleasure.
Once again one of them reaches around the front of me this time with a ball gag he forces into my mouth and secures around the back of my head. Next a pair of hands reach for my nipples -- both at once attaching clamps with a chain between them then quickly another paddle to my ass to make my body tremble shaking the nipple clamps and making me quiver even more as I scream out through the ball gag again a mixture of painful pleasures as they swing me halfway arounds so my side is up against the mast and they now have access to my front and back.
I feel a new type of impact across my stomach and hitting the chain between my nipple clamps. It feels like a bunch of needle stings at once- must be a whip that they brought out. A few more quick impacts between my front and back as I squirm around on my tippy toes held up by the mast. Through my moans and screams muffled by the gag I heard both Ian and Brendan laughing at how pathetic I must have looked and how much they knew I was loving it.
They must have divided up so that one had the whip one had the paddle going back and forth between sides of me as they kept working me over interspersed with spitting on me as well and keeping calling me a slut as my cock continued to leak precum all over my legs and the deck. Every time they hit my ass and the butt plug in a certain way in particular it sent waves through my body making me thrash around and globs of cum fly around.
Then there was a new sting- this time to my balls that made me let out my loudest yelp yet. They must have pulled out the small paddle at the end of a long stick to sneak between my legs to really give my balls a torture. It wasn't bad enough that my balls were overflowing with cum having been locked continuously for months now, but now they're hitting them hard with this switch. It was painful but I loved it and each impact brought more cum flinging out of my tiny locked cock.
Now alternating between 3 different types of hits between my ass, balls, and stomach, they decided it was time to take a bit of a break and as I was still on my toes, they both started to piss all over me. It was a bit of a relief to have the impacts stop even though my nipples were still clamped and every twitch sent another jolt through both of them. Their piss on me also made me have to go so I was thoroughly drenched in piss by the end of it as both of them started rubbing their hands all over my pissy body rubbing it all into my body. As they slowed their hand movements I felt the pressure relieved on my nipples as they pulled the clamps off and then the ball gag was next to come out.
"You looked like you enjoyed that a lot you little slut," Brendan's voice inquired.
"Yes sir, I am here for you to play with and for your pleasure sir." I replied as one of them also went around to my ass to remove the plug in a hurry once again leaving me feeling empty but immediately the other one grabs my ankles from the deck and puts them on his shoulders as the halyard is lowered a bit so my ass goes right onto his still throbbing hard cock for another fucking held up by my wrists still attached to the halyard. It was a wonderfully hard and fast pounding that I needed after the whipping that I just went through.
A few more hard thrusts balls deep into my ass and I could feel him explode shooting his load into me shaking from all the sensations and the last few thrusts before his cock started deflating and falling out of me. I try to hold his cum in my ass, but it's so stretched out at this point, I don't know if I can. I start to feel it dripping down my ass as my ankles are lowered back to the deck and I can stand again as I'm spun around and bent over as the second cock is thrust in my ass balls deep.
My already wet and stretched out hole takes it easily but he hits right at my g spot to make me spurt more globs of cum out my locked dicklet. He continues to pummel my ass hitting the same spot over and over again letting me finally fully drain my super full balls all over the deck. After what seemed like an eternity of hitting that same spot and a continuous prostate orgasm, I feel through my whole body his final hard thrusts as the second load of cum is sprayed up my ass.
He wrapped his arms around me in an embrace as his hard cock still plugged my ass not ready to deflate yet. We hold there lost in the moment forgetting that we still have a guest with us too watching until he bends down and makes contact with my lips as I move to stand back upright and the blindfold removed.
When I can finally see again, we all make eye contact in the moonlight, our bodies drenched in sweat, piss, cum, and lube and in unison let out a sigh: "That was amazing."
End Chapter 4