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GaySailor92
Chapter 5: Post Dinner Entertainment
I collapsed to my knees on the deck my arms held above my head still attached to the halyard exhaling a mix of emotions. Exhausted and spent from all of the action, proud to have fulfilled Ian and Brendan's desires and fantasies, somewhat fulfilled myself at least with two loads of cum in my ass, yet still horny even after shooting cum through my cage. The joys of still being locked up.
Just as my ass was starting to feel empty again, Brendan came up behind me and put his arm around my waist pulling my ass up in the air. With his other hand he takes the butt plug, the metal has cooled on deck in the evening air and shoves it back up my ass. I let out a yelp of surprise- shocked by the coldness of the smooth metal plug as it first touched my skin and started cooling down the inside of my ass and plugging in their two loads of cum. Ian started lowering the halyard to release my hands and I feel the temperature evening out in my body and the adrenaline recedes. My body starts to feel the effects of tonight's play- stinging from the paddle and whip, my shoulders from being strung up the halyard. A little painful yes, but oddly also got me starting to stiffen in my cage again already.
I hear a splash behind me- Brendan has already jumped back in the water with an abundance of energy.
"Well, that's one way to clean up- and won't track through the cabin," Ian winked at me before finishing securing the halyard and flipping over the side of the boat, his delicious cock not quite fully soft bouncing around as he entered the water.
I thought `what the hell why not?' and joined them in jumping into the water. I hit the water and immediately the salt water started stinging every hit Brendan and Ian made earlier in the night. I surfaced and let out another scream that was met by laughter from the other two at my discomfort. My body quickly adjusted to the salt as I gently rubbed over my body with one hand while treading water with the other and avoiding being dunked under water by the other two who were competing with each other. I quickly called it quits and swam around to the aft deck to use the shower in peace while I could and then get started cooking dinner.
The hot fresh water and soap felt good on my aching body. Lost in my moment I barely noticed as more hands started gently and sensually soothing my body.
"Ooh yeah that feels so good!" I said as the other two continued to work their hands.
I let them continue their work a few more minutes as I became completely relaxed until my stomach reminded me- dinner's still waiting and I could only imagine how famished the other two would be.
"Ok boys, I'll let you finish cleaning each other as I get dinner ready."
And with a final rinse and a kiss on the lips to each I grabbed a towel to start drying off. Once I was mostly dry, I fired up the grill to warm up before I went below. I first got all the plates, glasses, silverware, and place settings to the table in the pilothouse and then got the steaks searing on the grill as I watched Ian and Brendan finish their showers while still teasing at each other- Brendan with his hands always migrating to Ian's dick and Ian's hands migrating to teasing Brendan's crack. Much to my surprise, Brendan seemed to embrace it more than I expected for a theoretically straight guy. I'm guessing this might be a prelude to what's going to happen later tonight. I just got fucked hard but shit just looking a glance at either of them and I feel the blood rushing again as they toweled off their hot bodies and hung up their towels to dry in the still warm night air.
"Ok ready to help!" Brendan said still completely naked and seemed completely natural to him.
"Why don't you set the table and I'll clean up the gear we left on the deck and Trevor just keep cooking, that's smelling great!" Ian beat me to it.
"Everything is on the table," I added looking at the back of them getting to work.
I finish grilling and plating everything as Ian pours wine for all of us gathering at the table and dig in. Brendan and Ian really were as famished as I thought- hopefully I cooked enough food! Conversation was sparse at first- not due to lack of things to talk about- just hunger! But soon Ian starts the conversation getting to know Brendan better with his other interests, work, family, etc. We all chat for a while as we finish eating and then just relaxing enjoying the conversation and each other's company. Brendan fit in with Ian and I so well; it felt so natural and I could see the sparkle in Brendan's eyes that he was finally able to act on things he's never let himself want to do. I wonder if he'd want to come back sailing with us again?
Soon the last of the bottle of wine was split between our 3 glasses and I knew once the glasses were empty, we'd have to get up again to clean up which I wasn't looking forward to. Granted, I was pretty sure after that we'd get back up to other things I'd enjoy. My suspicions were confirmed when Ian started asking Brendan more about his sexuality and sexual fantasies.
I couldn't help but also interject:
"I saw you enjoying Ian's fingering of your crack during your shower before dinner- did you enjoy that?"
"Well, I didn't hate it... never really played with my own ass before though, just a few girls and one guy. Before you that is..." He seemed slightly hesitant to admit but knew he was in a safe space to share.
"Do you want to explore it?" Ian inquired as we both looked to Brendan with as reassuring expressions as possible.
After a few silent moments of contemplation Brendan let out a sigh: "Yeah I think I do want to explore it and as long as Ian doesn't shove his monster dick in me right away at least, I think you guys are the right ones to help me."
Ian laughed at the comment but I could also see his ego grow 5 times -- I had to roll my eyes at him.
"Don't worry, Trevor will start you off slowly with fingers and toys. He's the bottom expert as you could tell. Hell, maybe I'll even let him unlock and fuck you if you can't handle my monster yet," Ian explained with a wink.
A shot of adrenaline shot through my dick at the thought of getting unlocked to fuck him -- he did have a great looking ass after all- and it was a surprise that Ian didn't want to cuckhold me into just using toys on Brendan to open him up enough for Ian to fuck him. Who knows what will actually happen though, Ian still has my keys.
Brendan let out a bit of a nervous laugh: "I like the sound of start off small and trust Trevor to help open be up- not sure about him fucking me, I don't know how big he gets since he's just been locked up the whole time."
"Don't worry I'm not that big in the first place, plus since I never get hard it doesn't always get as big. Oh, and I don't last long when I get unlocked so I wouldn't be pounding you all night." I tried to reassure Brendan with a wink.
"Then you'll get locked right back up!" Ian continued. "Trevor, why don't you and Brendan head down and get him cleaned out ready to go while I do the dishes. Just wait for me to really start ripping into him." Ian finished as he got up starting to gather dishes to take to the galley.
I got up as the but plug in me hit my prostate just right again sending a drop of cum dripping out my straining locked dick. Brendan noticed as he was sliding out of the dinette behind me. He reached out a finger to wipe up the drop of cum before it hit the floor and then licked it off his finger with a devious smile. Just like Ian would do and look.
"So you like the taste of cum too?" I asked.
"I've tried me own a time or two but never someone else's. But I'll try more." Brendan explained.
I winked back at him and then guided him in front of me with a hand on his firm round ass and followed him down the companionway and forward to the sex cabin. I started explaining to him my method for prepping for bottoming after a meal and to not overdo it with douching. Just enough to get the bits out and to not worry if it's not perfect because after all in anal sex, shit happens...
As he finished up in the head, I started pulling out the supplies for the rest of the session. We had tons of new toys that I haven't even had a chance to try on myself, but was about to use to open up a new hole which was exciting to me! Of course, I also made sure we had plenty of lube ready to go- and a towel to wipe up the lube!
I sat on the bed admiring the layout of toys and in my own thoughts as Brendan and Ian both reappeared from either side of me both sporting semi erections as they came and stood in front of me. It made my mouth water wanting to just start sucking them to get them rock hard, but that's not what we were here for- it was time to make a new bottom!
I stood up and kissed Ian and then turned to a longer kiss with Brendan and grabbed his ass in an embrace that I could feel excited him as his dick grew. I broke off the kiss and asked:
"How do you feel? Are you ready and relaxed?"
He nodded and leaned in for another kiss before laying him down on his back and pulling his legs into the air to expose his hole. I talked him through breathing to relax and started to caresses him between his taint and his hole just to get and keep him relaxed as I eased him into the idea and act of getting penetrated. I could see him relaxing into and getting even more aroused as his dick hardened. I leaned in for another sort but sensual kiss and then started kissing down the center of his body and down his dick and balls to his hole where I proceeded to start rimming him.
I worked my tongue around his hole and put pressure right at the center as he continued to relax and experience the pleasure of all the nerve endings at the entrance to his hole. I continued as Brendan started letting out soft moans of pleasure and continued to let the opening of his hole relax and tip of my tongue in. I was in my own zone eating his ass as I felt a hand on my shoulder move me away -- it was Ian saying "I want a turn." So I traded places with Ian who was obviously liking what he was watching as he was stroking his rock hard dick as I was rimming Brendan.
I watched grabbing my locked nub to try to sooth the strain of my natural reaction to the scene in front of me for a few moments before moving to Brendan's lips for to share the taste of his ass with him through a kiss. He must've enjoyed it the way he wanted to keep making out but after another minute I knew it was time to move on.
I grabbed the lube and got ready to start fingering him as Ian finished up his passionate rimming. He stood up and made out with me so we could share the taste of his ass as well amongst our mouths. Then he whispered into my ear: "I want to watch you fuck him,"
I nodded trying not to show my excitement for getting unlocked and being able to take his anal virginity. "Continue opening him up and I'll get your key, but you're not getting unlocked until right before you fuck him or you'll cum before you can penetrate him." He continued whispering in my ear as I smiled and almost laughed because I knew he was right- I'm going to burst just about right after I get unlocked.
"What are you two whispering about over there making me wait with my ass in the air?" Brendan interrupted.
"Just telling Trevor that he's going to get to fuck you but reminding him that he's only unlocked while his dick is in you. Let him free too soon and he'll cum even before he can get inside you." Ian explained as I moved back into position at Brendan's hole.
"I'm going to start by fingering you now and then work the toys in before Ian will unlock me and then you can see how small I am hard. Don't worry, you'll be able to take me no problem, I have faith." I winked at him as Ian disappeared to the back of the boat to get my key.
I knew Ian didn't keep my keys on him at all times- I mean we spend so much time naked there's no way he could! So, I knew he had to stash it somewhere in our bedroom- now stateroom on the boat and while I'm sure I could find the key and unlock myself if I needed but I don't see a need. Of course, I wanted to unlock at times when he said no but I know if I NEEDED to unlock, he would unlock me. It's this trust that makes it work for us- Ian wasn't all that into chastity until I introduced it to him. If I told him I wanted to quit it forever, that wouldn't change anything in our relationship.
Sorry, I get side tracked sometimes. I started working in my fingers into Brendan's hole with plenty of lube to his growing moans of pleasure. I make sure to work on relaxing his hole to take more fingers as well as starting to brush up against his prostate to really feel the pleasure you can get from anal sex. Soon I could fit 3 of my fingers in no problem and knew it was time to move onto one of the toys. I lubed it up and started to gently put pressure on the toy until his hole would accept it much to Brendan's pleasure.
Soon Ian returned and we smiled at each other as Brendan's eyes were closed moaning in pleasure as I worked his hole with now a moderately sized toy. Ian shook the key to my chastity cage in one hand as he was stroking his dick in the other clear that he was going to enjoy the show. He stood there another few minutes before asking:
"Are you ready for the real thing now Brendan?" Bringing him out of his trance as I slowed and then slowly pulled the toy out of his ass.
"Wow, I didn't know how good my hole could make me feel," he gasped as he laid his legs down to stretch them out. "yeah I think I am ready -- well at least to see how much dick I have to take."
"Good- your ass gets a short break as we rearrange things before I can unlock Trevor," Ian started with that devious smirk on his face.
I shot Ian a confused and slightly angered look. It was clear he had something different in mind than I had thought.
"See Trevor's going to be restrained on the bed spread eagle, then I'll unlock him and we can see how hard he can get then you can ride his cock if you want and then when you're done, weather he cums or not, he'll stay tied until his cock deflates and is locked back up. Do you like the sound of that?"
"Oh yeah I do!" Brendan was excited and if his dick wasn't fully hard before, it definitely was now. "So like I don't have to give up being dominate while bottoming? I enjoyed laying there and what you were doing, but I also like the idea of being able to control it more."
"Then hop up and pull out the restraints from each corner and get Trevor on the bed." Ian instructed Brendan showing he was still in charge of everything.
So Brendan hopped to his feet and pushed me onto the bed and found the restraints already prepped at each corner of the bed and with Ian's help I was strung out spread eagle on the bed ready for what was to come. But they couldn't just go for it. First had to come a barrage of hands and kisses all over my body to make sure I was straining in my cage as much as possible before unlocking me and they were succeeding!
My balls were hurting the most as the cage contained my attempt at an erection when they both pulled away from me and Ian handed Brendan the key to my cage:
"Ok Brendan time to unlock your toy and see what you have to play with."
"I'm ready! But how do you work one of these things?" Brendan still needed more teaching.
So Ian guided him through where to insert the key and pull out the captive lock and how to remove the cock tube which is when my dick really started inflating to the point I wasn't sure they'd be able to get the cock ring off soon enough. Thankfully with a little lube I was finally free! Even after they took off the last of the contraption and then left me alone my dick continued to stiffen in my first full erection in I can't even remember how long.
Coached by Ian, Brendan then got back onto the bed and straddled me his ass towards my dick and once we made eye contact, never broke it as he grabbed my cock and started to gently stroke it and size up how big it was.
"Well Mr. Trevor you're not as small as you made it sound." He interrogated.
"It's been a long time since I've been fully erect, I can never remember how big it actually is," I answered as he leaned down for a kiss still with my dick in his hand and me already on edge.
He broke from the kiss and Ian was there with the bottle of lube as he helped lube up both my dick and Brendan's hole finishing with another finger to make sure that he was ready to go. Then after a few deep breaths, he lined up ass with my dick and started to sit back and take my dick into his ass with a long exhale and expression of both surprise, a little discomfort, but also a whole lot of pleasure as he slid further and further down onto my cock.
I was throbbing, heart pounding as my dick hasn't been pleasured in so long. I tried to wiggle my hips up and down to stroke my cock in his ass but he just sat on my hips to take a moment to catch his breath. I tried to be patient for his first time, but being tied up and still with the butt plug up my ass, I had so much stimulation that I could barely stand it.
After what seemed like an eternity of Brendan sitting with my cock all the way up his ass, he starts to lift himself to slowly fuck himself on my cock. I felt like I was about to burst but tried to hold on as long as possible. I looked into Brendan's eyes and could see how much he was enjoying it and how he wanted to keep it going as long as possible. I broke eye contact to look over to Ian who was licking his lips and slowly stroking his cock leaning against the bulkhead of the cabin enjoying the show.
I turned back to Brendan as he was now stroking his cock too and I could tell was dying to cum. He let go of his dick and leaned in to make out as he increased the pace of his thrusts and made sure his dick rubbed between our hard abdomens. He keeps going as my body starts to tense and tighten, I'm about to blow when he suddenly stops his thrusting on my cock and clenches his ass muscles, holds our kiss, and presses his cock against my body as I start to feel his cum sliding between our bodies. This combination of sensations set me off and my body tensed, spasmed, and I tried to thrust my hips into him as far as possible as I spewed my load up Brendan's no longer virgin ass.
Brendan broke off the kiss and laid his head next to mine still in an embrace and stuck together with his cum as Ian mounts the bed on his knees to finish stroking his cock's load out onto Brendan's back. Then he snuggled up next to us -- everyone's cocks deflating as we all caught our breath satisfied with our post dinner entertainment.
"Anyone up for some dessert?" Ian broke the silence.