Tyler's third day at the resort was fun for him. Exploring the multiple different small islands that created the small atoll that the resort was on came with seeing multiple very different fetishes come to life. Obviously, there were multiple that took place behind closed doors, but those that didn't need to often had a public area where people could watch or even take part, such as the pony play. In addition, there were plenty of non-fetish activities scheduled throughout the day such as kayaking around the inside of the atoll that kept him busy. Though the fact that his cock was completely denied him did not make the day any easier and by the end of it, he was leaking small amounts of pre out of need.

While he didn't know when Hiccup would come for him, Tyler was hoping it was as soon as he wiggled on the bed out of need. Looking over at where he had put the Flint and lube, he was about to get up and grab it when there was a knock at the door. He rushed to the door eagerly, hoping it was Hiccup. Looking through the peephole he saw it indeed was Hiccup and so he rushed to get the door open.

"Hiccup!" Tyler exclaimed, surprising the auburn-haired man slightly who let out a soft chuckle.

"It's good to see you too Toothless. I'm sorry about yesterday." Hiccup started before being interrupted by Tyler.

"That's okay, can you please remove the cage?" He asked with a whine. This caused the chuckle from Hiccup to continue a bit longer, which only flustered Tyler even further.

"Oh dear Pup, I told you when I put it on that the only way it's coming back off is once that Flint fits all the way up your rear." Hiccup said, cupping Tyler's check in his hand. This caused Tyler to whine even further. "But how about this, I'll help you work towards being able to fit it and won't keep you from climaxing from the anal stretching I give you?"

"YES!" Tyler answered excitedly without a second thought, now having some way to be able to climax again, even if it was only through anal.

"Alrighty then Toothless, let's go see how much work you require." Hiccup said, grabbing the D-ring on Tyler's collar in order to pull him through the doorway and into the hallway. After double-checking that his card was still hanging from his pants, he eagerly followed behind the man. Something about being led around by him feeling right. Maybe he would have him use a leash next time. The thought of Hiccup leading him around on a lease caused his cock to try and harden once again, but ultimately fail.

"Here we go." Reaching a door labeled simply as Anal Training, Hiccup opened it and led Tyler inside. Inside was nothing but wall-to-wall dildos and lube, mostly Bad Dragon toys and cum-lube, clearly meant for use on him. In one corner was a small shower and drain with a douche kit mounted to it. "Strip, and then let's get you cleaned out."

Tyler nodded and soon had stripped out of everything, leaving him standing before Hiccup in just his cage and collar. Looking him over, Hiccup nodded and brought him over to the shower which the sit-up bench clearly meant for him to sit in while getting cleaned.

"Lay down on the bench and let's prep you for anal." Hiccup said, grabbing the nozzle and rubbing some lube on it while Tyler sat down. Turning on the water to make sure it was warm, Hiccup nuzzled the nozzle against Tyler's rear. "Ready for this?"

"Ready." Looking down at his dom, Tyler nodded his head before letting out a soft moan as the small nozzle was pushed into him. While he wasn't new to douching, it was still a strange sensation to have his rear filled with water before being told to push it all out. Not that it helped his beleaguered cock.

"Alright, go find a size you know you can take and we'll start there." Hiccup told him, to which Tyler nodded and got out of the seat in order to find something he knew he could take. Looking around the room, he found it to be well organized by size. Finding something he recognized, he picked up that dildo from the wall and turned back to Hiccup, who at this point had grabbed a bottle of cum-lube.

"Do you guys have a deal with Bad Dragon or what?" He asked, Hiccup seeing what he was in his hand and bringing a soft chuckle out.

"Something like that, and a medium Diego, good pick for a beginner. But when we are done you aren't going to be a beginner anymore." Hiccup answered, coming over to take the dildo from him and gesturing at a nearby padded bench for him to lay down on. Doing so, Hiccup took his shirt off as well before kneeling behind Tyler.

"Ready for this Toothless?" Hiccup asked, nuzzling the tip of the canine dildo against his ass.

"Please, just put it in me already!" Tyler responded, not in the mood to be teased anymore as he already felt close to a climax.

"Ah ah ah, since when does the Pup tell the Owner what to do?" Hiccup asked, smiling as he faked pulling the dildo away.

"I'm sorry Master, please fuck me with the dildo." Changing up his response as he whined in need. Hiccup could tell how turned on he was based on how hard his cock was straining against the metal bars of its cage. Without saying another word, he started to push the tip of the silicone dildo into the man in front of him. With a little guidance, the tip went in without any problems and brought out a deep moan of pleasure from the man it was being inserted into. From there, Hiccup worked the dildo in and out of Tyler until he was able to push the knot at the base into his rear.

A deep gasp came out of Tyler's mouth as the knot was pushed into him, moans of pleasure being brought out during the whole process as his cock continued its twitching from inside its cage. With the knot now inside him, Hiccup let go of the base and let it sit there to stretch out Tyler's rear a bit.

"There, how does that feel having the whole thing in there? Should we maybe try for a bigger size since that went in too easy?" While Tyler tried to answer verbally through the gasping and moaning as his rear was filled, Hiccup used the fact that his pup's caged cock seemed to strain even harder at the thought of being filled even further as a confirmation. "I'll take that as a yes." Chuckling softly, Hiccup walked back over to the wall and grabbed the same toy, just one size up. Coming back, he gently stroked Tyler's ass causing the bound man to shudder a moment at the soft touch. Feeling regularity in the bumps, Hiccup started to trace some more and noticed a pattern that made him worried, but it was something to be brought up at a later time as he focused back on stretching out his pup's ass.

Lubing up the new dildo, he held it in one hand while using his other to start the process of pulling the old one out. With a loud moan and a wet schlop, the canine-like dildo and knot slid from Tyler's rear and it was quickly replaced with the tip of the large Diego. Hiccup could see how Tyler was reacting to the obviously larger dildo pushing against his rear. Always wanting to make sure everything was okay, Hiccup paused for a moment, "This is the next size up, are you sure you want this Toothless?"

"Yes, Master. Green Light." Was the response that Tyler gave to him, his poor tortured cock straining hard against the unyielding steel of the chastity which engulfed it helping motivate him to agree for the next size up now that his ass had been loosened by the first dildo. The silicone tip of the dire wolf dildo easily slid into his stretched and lubed ass, but as the rest of the body started to widen out and push, it became slightly more difficult for both Hiccup to push and Tyler to receive.

A loud moan escaped Tyler as the dildo was pushed further and further into him, stretching out his rear and causing him to start panting. Hiccup kept pushing slowly, the lube on the dildo and that which stayed in Hiccup from the previous one helped make sliding the large mass into Tyler much easier. Soon most of the dildo would be inside him, with just the large knot at the base to push in. Giving a push, Tyler gasped as he felt his breath get taken away from the largest thing to ever be shoved inside him as the knot slipped past his sphincter and lodged the whole length of the dildo inside him. The bound man would hiss, not only from the pain of having his rear stretched out that wide but also from how hard his cock was inside of his cage.

"Let's go ahead and hold off here," Hiccup said, leaving the dildo to rest inside his sub's rear as he recognized a body at the limit of what it could take. Tyler nodded and agreed, the dildo currently stretching out his ass was as large as he felt comfortable taking. Anything larger he knew wouldn't fit and would only cause him pain and harm. He was soon distracted though as he felt Hiccup's hand gently caressing its way up his ass, to his back, and then to his head.

"Is it too much or just right to stretch you out?" Hiccup asked the bound man gently, making sure their eyes met.

"It...hmph...Is just right to keep me stretched out but not too painful."

"Good, because I want that to stay in you for a while. So." At this point, Hiccup unzipped his pants and let his semi-hard cock flop out. "Suck me off and once you're done, if you've done a good job, I'll remove the dildo. If you don't do a good job, that dildo stays in you." Tyler looked between the cock in front of him and the face of his dom and smirked. If there was one thing he was grateful to Dagur for, it was teaching him how to give amazing blowjobs.

"If doing a good job is all, then this thing won't stay in me long."

"Carefully Toothy, a cocky pet requires punishment to keep it in line,"

"Yes Master," Tyler hung his head before blinking a moment, certain that Hiccup wouldn't do what Dagur had done, but the thought was in his head and it wouldn't go away. The still-healing welts on his ass starting to burn. Resting his head on the bench, Tyler softly said, "red light."

"What was that?" Hiccup froze, not sure if he heard that right.

"Red Light!" Tyler said louder. With that, Hiccup got to work. His cock got put back in his pants as he started working his way around his submissive and undoing all the bindings holding him to the bench. Reaching his rear, Hiccup grasped the base of the dildo.

"I'm going to pull this out now, are you ready?" Looking up at Toothless's head for a response, all he got was a gentle nod before he started to remove the large silicone object. Tyler moaned gently at the removal but stayed still till it was removed fully. Hiccup watched as Tyler got off the bench and seemed to curl up in a nearby corner of the room with his back against the wall.

"Hey, is everything alright Toothless?" Hiccup asked, coming to sit across from the now terrified man who until a moment ago was a confident submissive.

"P..Please don't whip me." This caught Hiccup off guard, as there wasn't even a whip in the room. Huffing softly, he looked over the man in front of him before it clicked in his head. The still healing welts on Toothless's ass and his aversion to whips, which snapped into place when he had jokingly threatened punishment for being cocky.

"Oh dearie, I would never do that to you." Shifting closer, Hiccup wrapped an arm around the gently trembling man and brought him in for a hug. Toothless buried his head in the man's neck and hugged back, cuddling up to the source of comfort. He didn't care that he was still nude, but the man who had been picked to be his dom and whom he had developed feelings for was cuddling him close and it helped him to recover from a panic attack and flashback combination that he never would have been able to pull himself out of in such a short time.

Shifting the two of them so that Toothless was in his lap, Hiccup wrapped his arms tightly around him and held him close. Even after the soft shakes had gone away, he didn't loosen his grip in the slightest. Not that he would admit it to anybody, but of all the submissives that he had Dominated over the years, this was the only one who had somehow managed to worm their way into his heart. Smiling softly, he rested his chin on the top of Toothless's head and continued to hold and comfort the man, gently drawing random shapes on his bare back. The pair sat like that for the rest of the session, at which point Astrid poked her head in.

Normally Hiccup was good with the time, but he had lost track while comforting Tyler, and Astrid's face appearing in the doorway let him know just how long he had gone. Waving her away, he knew that they were at least half an hour over their scheduled time and there was a couple waiting for the room. Looking down at the black hair he saw that the young man had fallen asleep in his arms, he gently started to shake him. "Hey, Toothy. It's time to wake up."

The body in his arms refused to wake up, which caused Hiccup to sigh softly before he started to stand up. He wasn't going to try and fight the adorable sleeping form in his arms. Leaning down, he managed to grab a blanket that was kept in the room in order to cover up Toothless's nude form as he left. Walking out the door, he saw Astrid still standing there with a confused look as she saw who he was carrying.

"Grab his clothes for me please." He said softly. Astrid nodded and went into the room and grabbed the clothes and brought them out. She followed the pair as Hiccup carried Tyler to his room. The only move the sleeping man did was to curl up tighter against Hiccup's chest as he was carried to his room. Opening the door for them, Astrid stepped inside to set his clothes on a nearby chair. Smiling softly at him, she stopped on her way out.

"Is everything alright?"

"I think so, let me get him in bed and then I'll explain it." Astrid nodded as Hiccup carried Tyler over to the bed and after throwing the covers back he went to lay the man in bed. However, there was a problem. Even though Hiccup had let go of him, Tyler was not letting go of Hiccup. This was a problem, as Hiccup did have things to do but the more he tried to undo Tyler's grip the stronger the man's grip would become. With a gentle sigh he gave up and after slipping his shoes off, crawled into bed with the man he was coming to love.

"You know you have a meeting?" Astrid hissed softly at Hiccup as she watched him crawl into bed with one of his clients. Admittedly they had all done it before but it seemed like there was something else here. That and he really did have a meeting.

"He won't let me go, please move my meeting to sometime later. Or better yet do it yourself. It's just the resupply." He whispered back to her, glad he had finally accepted her offer for help and started to train her.

"Fine, but I expect a full explanation," Astrid answered before she left the room, shutting the door behind her as she went, bathing the room in blackness. With a soft sigh, Hiccup looked at what little he could see of the man holding him tightly before accepting this was where he was sleeping and got himself comfortable before falling asleep.

-0-0-0-0-

With no alarms, it wouldn't be till mid-morning until either of them started to wake up. While neither of them knew it, it would be a very eventful morning. The first to wake up was Tyler, though wrapped up in blankets and cuddled close to Hiccup as he was, it was rather difficult for him to start waking up. After a few minutes, he would try and roll over from where he was laying, but got stopped by Hiccup's arms. Confused, the black-haired male slowly opened his eyes to see how tangled he was in the blankets that it kept him from rolling over. Instead of blankets, he found arms wrapped around his chest that were holding him still. Tracking them back around to their owner, he found Hiccup fast asleep behind him, acting as the big spoon.

"AHHHHHH!" Tyler blurted out before he could stop himself once he saw that it was Hiccup who was snuggling him against their chest, as well as trying to shift away.

"AGHHHH." Hiccup yelped as he was suddenly woken up by a scream and somebody pushing him away. "What happened?"

"We slept together!" Tyler would be on the other side of the bed, wrapping himself up in blankets and trying to hide the fact that he was nude. "While I was naked!"

"Yes... that is usually how it goes when two people sleep together," Hiccup stressed, his sass already showing this early in the day. Toothless lifted up the sheets again to see if he wasn't dreaming and indeed he wasn't. Blushing he looked at Hiccup, who was laying lazily beside him and slowly stretching like a cat. It gave Toothless a good view... a very good view.

"You good?" Hiccup asked as he looked at his new lover who was still slightly freaked out from waking up in such a strange situation.

"I freaked out okay! It's just...I..." Tyler sputters a moment as he looks away, "I like you okay! From the moment we had our first session. But you probably already have somebody and are used to turning down your client's advances."

"Hey, look at me," Hiccup reached out to gently turn his sub's head to look back at him, seeing the tears starting to form in preparation for rejection. "I like you too."

"So what exactly does that make us then?" Tyler asked, dumbfounded at the turn of events as he looked up at the hypnotizing forest-green eyes of the man sitting in front of him. With a smile, Hiccup didn't respond as he simply leaned in close to start kissing the overthinking male in front of him. This would cause Tyler to squirm a little bit but he would soon melt into the kiss, which would last for a few seconds before Hiccup broke it.

"How about boyfriends and dating?" Tyler would nod at that statement.

"I guess we should know each other's real name then, mine is Tyler. Toothless is a childhood nickname that stuck."

"Awww, that is adorable!" Hiccup exclaimed, prompting Tyler to blush once again. "Just like you."

"Mhhhmm...So what's your name?" With an ever deeper blush, Tyler tried to deflect the conversion back to what it had been to start with.

"Hiccup," This answer confused Tyler.

"No, I mean your real name."

"It really is Hiccup." Tyler would stare at his new boyfriend for several seconds, trying to figure out if he was still joking or not.

"You're not joking are you?" Hiccup would simply nod his head. "What kind of parents name their kid Hiccup?"

"Mine." Hiccup deadpanned. The two would look at each other before breaking out into laughter.

It would be a few minutes before they both settled down, Tyler moving to snuggle up to Hiccup in the bed. "How are we going to make this work? Do you work here at certain times or...?"

"I uhm...I'm actually the owner." He answers nonchalantly.

"Wait wait wait wait...run that by me again?" Tyler turned to look up at his boyfriend.

"I'm a private and eccentric billionaire who decided to open an island resort devoted to BDSM and other kink-related activities." Hiccup made it sound so super casual that Toothless had no retort for at least a minute. The other person just sat there looking at Hiccup as if he had just told the world that the sky was green.

"I...uhm...Don't usually play with the guests but...," Now Hiccup blushed. "You were just so darn cute,"

"Wait, say that again?" Toothless uttered.

"I said you were cute," Hiccup confessed. "I saw you enter the lobby and I swooned, alright!" Hiccup's cheeks were now beet red. "So I convinced Astrid to let me take over as your personal guide."

"Okay... wow," Toothless uttered. He actually felt a bit flattered that Hiccup went through all that trouble. "You know you could have just come and talked to me, right?"

"Hello, I'm Hiccup, the reclusive owner of the island. Would you terribly mind if you and I were to engage in very kinky sexual congress?" Hiccup deadpanned in such a serious tone that Toothless actually doubled over laughing and nearly slid off the bed by accident.

"Okay, the way you put that would have made it seem weird. I agree now," Toothless answered though he was grinning like a loon. "So now what?"

"I was hoping breakfast and perhaps I can show you my real playroom," Hiccup shot Toothless a lustful look. "Although I don't think we'll be needing a tray,"

"Huh?" Toothless questioned until he realized Hiccup was looking him up and down, intending on eating breakfast off of him.

-Two Years Later-

Stepping off the boat, Cami would have a look around the island that had claimed her friend. Behind her would be several boxes being unloaded.

"Cami! It's so great to see you again!" Astrid called out as she stepped away from the ponyboy that was hitched up to the buggy to greet the other blond. "Here for another session?"

"It's great to see you too Astrid, and not this time. Just dropping off the last of Tyler's things and coming to beat up on him for not inviting me to their wedding." Cami replied as the two women hugged on the dock. "Where is he? I thought he would meet me on the docks?"

Astrid would chuckle softly before leading them towards the buggy. "I think he knew you would do that so he is preparing himself for said beating. That's why they told me to give you a ride around the island first."

Nodding, Cami would step up into the buggy and take a seat as Astrid grabbed the reins and whip from where they had been set down and got them ready to move. With a crack of the whip against the pony's ass, he would start to walk forwards, pulling the two girls away from the dock and up the road. It would take almost a full hour for the three of them to make their trip around the small, interconnected islands. Astrid even lent the whip to Cami so that she could use it on the pony should he start to falter in his steps or obedience. Not that he would need it.

"That is one well-trained pony, good work! May I pet it?" Cami asked as they finished, knowing better than to approach a fully kitted-out pony and touch them without asking for permission from its handler.

"Absolutely! Feed him some of these as a treat for being so good" Astrid replied as they came to a stop near the back of the main building, handing Cami a small handful of white chocolate. Cami would get out and walk over to the pony, looking over the straps and gear that turned the person into a pony before standing in front of him so that he could see her due to the blinders inhibiting his sight.

"Such a good pony. Here, have a treat." Cami said, holding up her palm as she looked at what she had been given. The pony would neigh and bend over to start eating them, which allowed Cami to get a better look at a tag hanging from his collar. "TYLER!"

"And you must be Cami!" A voice called out from behind her, distracting her from the fact that her best friend had been the pony that pulled them around the islands. Turning around, she would see Hiccup come walking down the steps with arms outstretched. "It's an honor to greet the one that got Tyler off his cute little ass and to come to my island."

Before Tyler could get any closer, Cami would pull a rather large dildo out of her tiny purse and smack him across the face. "How dare you take the only interesting and polite kinky person in a fifty-mile radius away from me! That lovable ass is like family to me."

The smack would shock everybody there, with Tyler being the one to break the silence with a laugh at the situation. Soon everybody would start to chuckle at the situation as Astrid took Tyler to the stable to get him out of his pony play gear.

"Ya know, now that Tyler is living here with me you can visit for free anytime you wish right?"

"I uhm...Welcome to the family Hiccup!" Cami replies, holding the dildo up in her hand. "A late wedding present because I couldn't make it to the actual one."

Taking the dildo in his hand, Hiccup would look between the monster in his hands and the small purse it had come out of. "How did you...?"

"Oh, a woman never reveals the secrets of her handbag." Came the response from the blond as she reached in again and pulled out some cuffs and a length of rope, a smirk on her face. "Now, Wanna tag team Tyler when he gets back?"

"Hell ya!" Hiccup laughed as he patted her shoulder, leading her inside the mansion. "Ya know, I think I might just have a staff opening for you if you want it."

0-0-0-0-0-0-0-0-0-0-0-0-0-0-0-0-0-0

AN:

(Thearizona sees a cactus sipping a glass of wine)

Thearizona: "What in the.... Vala that you?!"

Vala: "Yup!"

Thearizona: "Why are you dressed as a cactus?"

Vala: "Why not? Also this onesie is super comfy!"

Thearizona: "Sooooo....."

Vala: "You are not borrowing my cactus!"

(Thearizona blushes)

Thearizona: "NOT THAT CACTUS! I didn't mean the dildo!"

Vala: (Sips wine)

Thearizona: "Whatever you do with that cactus is between you and it, I don't need to know! Did you at least enjoy the story you made me write?"

Vala: "Of course" (Sips wine)