For the next hour or some, the pair played around in the room. Fetch, catch, even just laying around and Tyler acting like a pet. With the somewhat limited things they could do during the first session and in the room, it ended with Hiccup sitting on the floor petting Tyler lovingly. Looking at his watch, Hiccup would notice what time it was and how long they had been in there having fun. "Alright Toothless, time to get you out of there and back to your room."

Looking up at his Owner, Tyler nodded and waited for him to start removing the gear so he knew when to stop acting like a pup. Starting with the plug, Hiccup would pull it out to another moan from Tyler and set it off to the side to be cleaned. Moving forwards he would start to pull the hood off. Once it was off, Tyler sat back on his heels, expecting the collar and cage to come off next. "Go ahead and get dressed Toothless, then let's head back to your room."

"B...But what about the collar and chastity?" Tyler asked, moving to stand up but was a little wobbling and so Hiccup helped him.

"The collar shows that you are taken, and as for the chastity. Well, you need something as a reward for once you're able to take that Flint up your ass." This got Tyler to blush softly but also whine as he got his clothes and started to dress. Indeed the cage was small enough that it didn't show through his shorts and make it obvious he had one. The collar, along with the Pup tag, was very visible around his neck though. Once he was dressed, Hiccup handed the hood to him to carry. "This is yours now, best hang on to it."

"Yes, Master." Taking it, Tyler held it in his hand and followed behind Hiccup once again as they left the playroom and made their way back to Tyler's room. It was an interesting experience for Tyler, who had never worn a chastity cage before to have the weight and solid mass between his legs as he walked. Once there, Tyler scanned the door open and went in, expecting Hiccup to follow him in but when he turned around he saw him still in the doorway.

"You can come in if you want," Tyler said, which got Hiccup to nod as he stepped into the room for the first time.

"So how was it? I like to go over things after a session, especially if we do things for the first time." Hiccup told him. Tyler gestured to the bed for him to sit down on as he put the hood down on the nightstand.

"Pet Play has been something I've always wanted to do. I didn't realize it would be that good." Sitting down across from Hiccup, he would look him in the eyes. Something he was still getting used to being able to do. "Well...All of it is something I've wanted to do but never brought it up with my old Dom." Tyler looked down.

"Bad break up?"

"Ya, how could you tell?"

"I've seen it a few times before. You don't have to tell me what happened if you don't want to, but know I'm here for ya." Tyler let out a soft sigh as he lay down on the bed.

"I was dating him as well, but he violated our safe word and kept going till he was satisfied."

"I'm so sorry,"

"It's okay, I broke up with him on the spot. I'm here on the insistence of a friend who's been here before." Tyler interrupted him.

"Well then, I guess you have good friends," Hiccup chuckled softly, which caused Tyler to as well.

"Ya...I guess I do."

After a few moments of silence, Hiccup spoke up. "Well, I'll leave you to finish unpacking. Remember to get something to eat and drink, it's a good habit to get into after a session." Standing up, Hiccup would start heading for the door. "If you ever need me, my number is in your folder." Sitting up, Tyler would watch him leave and shut the door behind himself to let Tyler have some privacy. Standing up after a few moments, he would walk over and make sure the door was fully shut. There was no knowing what else Cami had packed and he didn't want anybody else walking in on him.

Stretching out and popping a few joints, he got back to unpacking. Fortunately, Cami hadn't packed anything else in his bags but the large Flint and some cumlube, also from Bad Dragon. Taking it out from the closet, he looked over it. If what Hiccup had told him was true, then he wouldn't be getting his cage off till he managed to get this up his ass. Which didn't help as he felt his cock strained against his cage. "Fuuuck."

Putting the dildo back down, he started to strip down once again. Looking down at his cage, he was able to get a much better look at it. It wouldn't be going anywhere, the padlock held the cage to the base ring while the ring was tight enough that he wouldn't be able to slide his cock out the back in, not get his balls through the gap between the ring and cage. Whining softly, he went to take a shower to try and calm himself down.

--0-0--

Tyler managed to get through that night and morning without managing to think about his caged cock, but the moment there was a knock on his door he could feel it straining against his cage already at the thought of Hiccup there to take him to his next session and maybe remove it. However, when he opened the door it wasn't Hiccup standing there.

"Hello Toothless, today I'll be your trainer for the day while Hiccup is busy," Astrid said, standing in front of him in a completely different outfit from yesterday. Today it was a riding uniform made of a mix of leather and latex which hugged her every curve. "He suggested some pony play since you deeply enjoyed your puppy play yesterday."

"Yes, Mistress."

"Good Boy, you won't need anything from your room so please follow me to the stable so we can get you harnessed up." Tyler nodded and made sure he had his keycard with him, shut his door behind him, and followed Astrid down the hallway and then outside. As they walked, Tyler could see they were indeed heading for a stable. One in which he could see several other people in gear with other trainers being led to and fro.

"Alright Toothless, this'll be your stall for the day," Astrid said, opening a stall door that had the number 17 stenciled on the outside. "Remember your stale number Toothless." Nodding, Tyler would walk inside to see a small pile of gear off to one side on a bench. Wondering for a moment how they seemed to always know his size, he remembered during the reservation process they asked for measurements.

"I'm guessing you want me to strip and wait for you to get me geared up?" He asked, looking over at the slightly shorter blonde.

"Correct you are, and same rules pup play. Once that hood goes on I expect you to act like a horse. Understand Toothless?" She asked, looking up at him. Even though she was shorter, she carried herself with an air of authority and dominance that made it clear she was in charge.

"Yes, Mistress." Came his response as he started to strip. Shirt, shoes, pants, and underwear till he was wearing nothing but his cage and collar.

"I see Hiccup already has you caged, so I guess I won't need to," Astrid said more to herself than him as she went off to the pile of gear and got out a solid black full-body latex catsuit. The zipper in the rear was already open as she held it out for him to start getting in. "Don't worry, we prelubed it already so it would be easy to get in and not chaff."

With that reassurance out of the way, Tyler came closer and lifted one leg after the other into the suit and slid them into the holes made for them. The suit ended above his ankles, leaving his feet free, just as the arms ended at his wrists to leave his hands free. Behind him, Astrid zipped the suit up and encased him inside.

"All good Toothless?"

"Snug, but I'm good. Green Light." Tyler answered her.

"Answer, let's get you into the harness next." Going back to the pile, Astrid pulled out a black leather harness with red accents. Sliding it over his head and around his chest, she would start to do up the buckles that would hold it in place. Around his midsection was a corset-like cover which she squeezed tight enough he felt it was there, but not tight enough to restrict his breathing, and was attached to the shoulder/chest harness. Going between his legs, she had a plate that would cover up his groin and go between his legs to connect to the back of the harnesses. On the front was a ring and hanging from the back was a tail made from what looked like fake horse hair that fell to below his knees.

Once she had everything around his chest and groin attached and tight, she went about putting on multiple cuffs on his arms and tights. They had the same black leather with red accent construction as the body harness and were equally covered in D-rings. Looking over at the pile of gear, Hiccup saw some clips, an equine hood, an equine-shaped dildo, hoof boots and gloves, latex gloves and socks, as well as some more cuffs still waiting to be put on.

"This next part will be easier if you sit down," Astrid said, gesturing to the bench all the gear was on. Nodding, Tyler moved to sit down on the bench as Astrid grabbed a pair of latex socks and the boots. "While I put these on, put on the gloves."

"Yes Mistress," He answered as Tyler grabbed the latex gloves as he felt Astrid slide the first sock onto his foot. If the goal was to completely cover every single portion of skin then it would be accomplished as once the socks and gloves were on the only thing left was his head. Soon Astrid started to slide the knee-high boots onto his legs and feet. With the hoofs at the end, they forced his feet into that of a high stiletto heel. Lacing up the front meant that they would be nice and snug against his feet and thighs so they wouldn't slide. To make sure of that, another pair of cuffs were placed at his ankles and another at the top of the boots to keep them in place.

"Hands behind your back," Astrid ordered as she walked around behind him. Doing as he was told, he felt his hands slide into the hoof gloves one at a time. There was a grip on the inside for him to grab but otherwise, his hands were curled up into a ball. The final wrist cuff was then put on to make sure the hoof cuffs would not be coming off. Before Tyler could move his arms though, Astrid had clipped the four separate pairs of arm cuffs together, effectively binding his arms behind his back.

His breathing started to get harder as his cock pulsed against its cage. Pet play was something he had always wanted to try, and seeing photos and videos of people in Ponyplay had never failed to get him hard. The only thing left was the hood, which had a flowing mane out of the back and a laced entry that went up one side to firmly hold it to his face. On the front were reins attached to a halter in order to move him around.

"Any last words Pony?" Astrid asked him as she started to prepare the hood to come on him. He could see a gag on the inside that would effectively make him silent except for what he imagined would be equine sounds.

"Green Light." With that, Astrid nodded and pulled the hood over his face. Everything felt snug, even the bit gag in his mouth. The lenses over the eyes gave a slight tint to what he was seeing as if he was wearing a pair of sunglasses. Soon enough he felt the lacing at the back get closed and tied together. Astrid then adjusted his collar, the neck of the suit, and the neck of the hood so that they all overlapped and left absolutely no skin showing. What he couldn't see was her adding a carrot-shaped tag with Pony engraved on it to hand with his Pup tag.

"Come on Toothless, Up," Astrid would pull up on the reins as well as help him stand up from the bench. It took him a little bit to wobble on the hoofs before he found his footing. Feeling Astrid start to mess with the piece over his groin, Tyler looked down the best he could in the hood. He saw Astrid stand up and the tip of an equine dildo which he could only assume was now attached where his own caged cock was. This only caused him to strain harder against his cage. Giving a gentle tug on his reins, Astrid would be leading him towards the door to his stall. Breathing heavily, Tyler would take a few wobbly steps before starting to gain an understanding of how to walk comfortably in them

"Lift your legs, thighs parallel with the ground," Astrid said, swatting the underside of one of his legs gently with a riding crop once they had left his stall. This came as a shock to him, looking over at her as they had both stopped. "Do you understand Toothless? A proper pony walks in a high step where their thighs come up parallel with the ground, like her." Looking up to who Astrid was pointing at, he saw a female dressed in a similar outfit to him being led by a different trainer. Her legs came up with each step from a 90-degree bend at the waist and her knee. Looking back at Astrid, he stopped his foot once, indicating that he was good to keep going.

"Good boy, you remembered the nonvocal commands." She said before starting to lead him out of the stable once again. With each step, he would try to pull his legs up, but occasionally would fail and earn a gentle swat on the offending leg as a reminder. They would soon come to an empty arena, where Astrid would attach a long lead to his reins before moving to stand in the middle.

"Alright, this is going to help you learn how to walk and run in those boots and in the proper way for a Pony. Now start walking" Astrid said, Tyler having watched her walk to the middle of the area and having strung some of the lead out, meaning he was now several feet from her. Gesturing in the direction she wanted him to go, Tyler would soon start to walk in a circle around her in the area. He would stumble occasionally, still getting used to the boots and the walk, but never once did he fall. The tail behind him swayed between his legs, as did the large dildo hanging down in front of him.

"Alright, speed it up into a slow jog," Astrid called out after several minutes of Tyler not making a misstep or stumbling, starting to turn slightly faster as she expected Tyler to keep up. And keep up he would. Setting off into a slow job wasn't as easy as a walk, as he now had to perform the same motions faster. But with Astrid correcting him and giving advice, it was but a few more minutes before he was moved up to a fast jog. His breathing would increase, the gag not getting in the way though as he focused on his steps.

"Good Boy, do you feel up for a little running?" Astrid called out after several minutes of watching him jog around her. Looking over, he noticed she was further away as while he had been speeding up she was letting out buts of the lead. Letting out a whinny and nodding his head to let her know he was ready to go faster, he would focus back ahead. "Then Go!"

With that, Tyler started to run. The dildo attached to his harness flopped back and forth beneath him, his tail and mane fluttering in the wind as he transitioned into a run. Starting to pant now, Tyler would keep up his run as he followed the lead around the arena. His chest heaving against the harness and the suit, his arms bound behind his back straining against the clips. His ears would be filled with just the sounds of him panting through the mask as he ran, which sounded almost like that of a horse panting as it ran. Occasionally he would stumble in the run, after all, he was still new to wearing the boots, but for the most part, he was running just like any other pony out there.

"Woah!" Astrid would call out after almost fifteen minutes of running. "Bring it back down to a jog Toothless, let's get you starting to cool off," Glancing over at her, He almost didn't want to. Tyler had gotten into the mindset, he wanted to run, but he followed his Trainer's orders and slowed back down to a jog, and started to let his body come down from the run. Over the next few minutes, Astrid would have him slow back down to a walk while slowly reeling him back in till he was back to being a few feet away from her. Finally, she would stop him, reaching out to grab his reins.

"Good boy, you did a wonderful job with your steps. I can't wait to get you out here again. I think you might be a good show or race pony if we train you right." She told him as she started to lead him back towards the stable. This got a blush to form on Tyler's face, not that Astrid could see it. Though the idea of spending even more time in the gear did make him painfully aware of his caged cock once again. As Astrid was walking him back to the stable, they walked past a stall that had its door open and nobody but another pony inside.

"When will they learn to shut the...ooohhhh...This could be fun." Astrid said as she went to shut the door but stopped as she looked in to see why it was open. Stopping Tyler from continuing past her to his stall, she pulled him inside. Turning to look inside, he saw why they had stopped. In the middle of the stall was another pony tied to a breeding bench. Looking a bit closer he could tell that they were in fact, female.

"Come on Stallion, I've got a waiting mare ready and waiting for you as a reward for such a good job out in the area." She said leading Tyler up right behind the mare tied to the bench in front of him. Reaching for a nearby bottle of lube, she would start to lube up the dildo hanging from his groin. Huffing and panting, Tyler would stamp his hoof twice, as he wasn't what was going to happen next.

"It's okay, She is willing to take it, right girl?" Astrid asked, stroking the mare's ass, to which her hoof stomped once. "And if you're willing to give it to her, there might be an even bigger reward for you." Coming back over to stroke his pseudo-cock with lubed-up hands, She looked up at Tyler in an expecting way. "So, you ready to fuck this mare?" Looking back down at the inviting mare in front of him as she wiggled her ass, He stomped his hoof once.

"Good Boy! I'm sure you know how to use this thing," Astrid said, using the dildo as a lead to pull Tyler close enough to push the head into the mare's pussy. "Get going you Stallion, show this Mare a good time." With that, Astrid stepped back to allow Tyler to start fucking unhindered by her presence. Grunting softly as he felt his own poor trapped cock straining for its own release inside its cage underneath the suit, Tyler would start to push the equine dildo that was serving as his pseudo-cock into the accepting pussy before it.

This would bring out a moan from the mare as he started to thrust the dildo into her. Grunting from the exertion as he started to thrust more and more into her, he also whined from the fact that he was going through all the motions but not feeling anything on his own cock. In fact, his own cock was straining painfully against the cage and starting to leak pre from the situation. Not that Tyler could do anything about it except keep fucking the willing mare in front of him. She was taking the rather large dildo in stride, moaning out in pleasure as he thrust more and more in till their hips slapped together and the entire dildo was buried inside her sex.

Pulling back out slightly, Tyler would start to make long hard thrusts. Dragging the dildo almost fully out before plunging it all the way back in with each thrust. Each thrust he made got faster and harder as he got more and more in tune with the thrusts. Soon they would both be panting hard as Tyler had no other way to tell how close she was other than sound, but he kept fucking. Not that he would even climax, with his cock locked away so all he could do was thrust till the mare in front of him came. It would be a few minutes of hard thrusting from him before she finally climaxed with a loud whinny and a shudder on the breeding bench.

"Good boy Toothless, go ahead and pull out and let's get you back to your stall," Astrid said, having been just off to the side and watching it all. Huffing loudly as he started to step back, his pseudo-cock sliding out of the mare in front of him with a wet squelch. The last he would see before he was led away was her shuddering against the bondage holding her to the bench before he had to turn around and leave. It wouldn't take long for the pair to reach the stall Tyler had been given for the day.

"You did a good job there Toothless, let's get you some water." Reaching for a bottle with a long straw, Astrid held it up to his hood and through the open mouth in order to reach his mouth and spray the water inside so he could drink. After several spurts, Tyler had had enough water and pulled his head back slightly. Astrid picked up on it and pulled the bottle away. "You did a wonderful job both in the area and with that mare, I'm so proud of you boy." Reaching up, she would pet the nose of his hood like one would a horse.

"I'll let Hiccup know how much of a good boy you were today for me, but now I'm going to let you cool off a bit before lunch, and then maybe I'll see if you're any good pulling a cart." Letting the reins hang from his hood, Astrid would shut the door to the stall once she had left. "You'll be fine in here while I'm gone right? I shouldn't be gone longer than twenty minutes." She asked once she had shut the door. Tyler looked around a moment in thought before looking at her and stomping once. Hearing that, she nodded and left him alone in his stall.

Once she had left, Tyler took a good look around. The floor was lined with hay, as one would expect, a water bucket with a long straw for going through the hood was in one corner and a rather tall bench in the other. While Tyler wasn't that tall to start with, only 5'11", the hoofs he wore pushed that up to 6' 4". Trotting over to the bench like he had been taught, he would sit down and lean against the way to catch his breath. As he did you noticed once again how tight the cage was on his cock and whined softly. He hoped that once he saw Hiccup again the man would take pity and remove the cage so that he could climax. On the other side of things, he had written down he wanted to be edged so maybe this was part of that.

There were no clocks anywhere so he didn't have a concept of time, but he felt that certainly twenty minutes had passed so he stood back up from the bench with a grunt and went to the door of his stall to see if he could see Astrid returning. Leaning out the open slot in the fencing for just that, he looked up and down the stable and didn't see her. Huffing softly, he let out a loud whinny. After all, it had been twenty minutes hadn't it? Looking back and forth along the hallway he didn't see anybody else except other ponies in their stalls. After a few more minutes, some of the trainers started to filter back in. It must have been lunch. Standing at the door, he watched as Astrid came around the corner to the stable and started coming towards him with another bottle in hand. This one was filled with what looked like a protein shake.

"Settle down Toothless, it's barely been twenty minutes. Now here, I don't want you to be hungry cause you missed lunch." Astrid said, petting his nose once again before slotting the straw into his maw and letting him drink the meal. As he thought, it indeed was a chocolate protein shake mixture. It didn't take him long to suck it all down, with Astrid pulling the empty bottle away and setting it to the side. Looking directly into his eyes, Astrid made sure he knew what she said next was serious. "Now, I want you to think about this before answering. You can get out right now and relax the rest of the day, or we can keep going and you won't be out till dinner time."

Indeed, Tyler was having a wonderful time and didn't want to stop it. It's not like he could pleasure himself once he was finished anyways as the chastity cage prevented access to his cock. He also knew if he stayed it would be a bit of hard work, but he was fine with it so he looked Astrid back in the eyes and loudly stomped his hoof once. He watched as a smile spread across her face. "Such a good boy Toothless, now let's get you out of your stall and hitched up to the cart."

Opening the door, Astrid would lead Tyler to a different part of the stable where there were multiple different carts, buggies, and even carriages. Based on the yokes, they could be used with anything from single ponies to teams of eight ponies depending on the size. Astrid would pick a small single-person buggy and after placing him in the middle of the forks, started attaching the leads from them to his harness. The heavy-duty nature of it now made sense to him.

"Let's go Toothless," Astrid said, first leading him out of the area so he could get used to the sensation of pulling just the buggy. After a few minutes of that, she had him stop before sitting in the buggy and prompting him forwards. That is how Tyler spent his afternoon, pulling Astrid around the buggy track before going on one of the many different trails that snaked around the stable. While normally Tyler would object, with his body completely covered as it was there was no way to tell who he was at a glance.

The pair would get back to the stable as the light started to fade from the sky. Toothless was panting heavily from the long workout, his legs and lungs on fire but he wanted more. The pony play having woken something up deep inside him. Pulling back into the cart barn, Astrid unhooked him before leading him back to his stall.

"Alright Toothless, it's been a joy but we don't allow first-timers to stay suited up longer than a day," Astrid said as she shut the door to the stall behind them. "Otherwise I know you would want to stay in there, I could tell you really got into it." She said with a smile, helping Tyler down onto the bench so she could start the process of unbuckling and unstrapping the gear. Starting with the clips holding his arms behind his back, he would moan from the release of tension. Next was all the cuffs and the dildo before she reached up behind him to pull the hood off his head. As it came off he worked his jaw and breathed in large lungs full of air. His hair was matted down from the sweat of the day.

With the hood off, Astrid soon got his hoofs off, as well as the latex gloves and socks. From there she had him stand and started to pull his harness off. The lack of weight hanging off him, or the fact his feet were no longer forced into a point felt weird to him as he had been wearing it all day. Walking behind him, Astrid unzipped the suit and helped him free from the latex. The cool evening air on his skin brought a shiver as he stood there in the nude before his trainer. "So tell me, how was your first time as a pony?"

"It was..." Tyler struggled to find the right words to properly describe how he felt. "You're right, I didn't want it to stop. Something deep inside just...it clicked. Kinda like when I was doing pup play with Hiccup." Astrid would smile as she put the gear into a basket.

"Some people are nature submissives and will take to pet play like fish to water," She said to him, handing the man a towel and another water bottle. Wiping the sweat off his body, he would drink from the bottle, making sure to stretch out after the long confinement. Tyler would give a soft and shy chuckle at what she had said, as it had done a pretty good job of describing him.

"Now, would you like help to get dressed and to get back to the dining hall for dinner or can I trust you to make it yourself?" This question seemed to have a kernel of past experience behind it, but Tyler had already reached for his clothes and started to get dressed.

"I think heading back to my room for a shower first would be best," He answered, standing up to pull his pants up.

"Up to you, just make sure you don't skip dinner tonight. You had a long day and need the food." Came the response from Astrid, who made sure he finished getting dressed and then walked out of the stall with him. This was something new to Tyler, who was not used to being looked after in such a way.

"I Uhm...Got it." With that they continued to walk together back to the main structure, joining a few other people coming in from the many different areas of the resort.

"If ya need me or want to do that again, stop by the stable and ask for me or my number is in your packet," Astrid said as they got inside. "I had a great time as I'm sure you did, I hope to see you again Pony." With that, she turned and headed for the dining hall, leaving Tyler standing in the hallway. After a few moments to collect himself, he turned and headed for his room in order to take a shower.

Opening the door he let off a soft sigh as he walked in and shut it behind him, leaning against it as he thought about what had happened. Not that he didn't enjoy the day, in fact, it had been a pure delight to be dressed up and run about as a pony all day. The only thing missing had been Hiccup. He wasn't sure why he had attached himself so to the man, but maybe a hot shower would help relieve some stress and tension.

Grabbing clean clothes to change into, Tyler soon took a shower. The hot water running over his body did wonders to work out some sore spots that had formed, as well as soothe his sore and exhausted legs. There was nothing he could do about how pent up he felt, his cock still locked behind the unyielding steel of the chastity cage to which Hiccup held the key. Doing his best to clean in and around the cage, he soon finished and turned off the shower to dry off. Getting dressed, he looked at himself in the mirror. The face looking back at him was his, but somehow inside he felt slightly different.

Shaking his head at the silly notion that his time here was changing him into some non-stop kinkster, something he had always had a good handle on before, Tyler left his room for the dining hall in order to get some food. In a rather large room, there was always food available as one never knew when they would get a break from any session. However, at certain times of the day, there would be proper meals where instead of being something easy and quick to eat they were full buffet-style meals. It looked like tonight was mac-n-cheese and chicken strips, along with the sides to go with them.

After loading up a tray of food, Tyler looked for an open seat somewhere with not a lot of people. Finding an empty table wasn't hard, and having grabbed a drink Tyler would make his way to the table and sit down to start enjoying his meal. Everything that the resort did was five-star, which extended to the meals as well. While he had not been here long yet, Tyler found that every single bite was full of delicious flavor.

"Mind if I sit here?" A familiar voice called out causing Tyler to gag slightly on what he was chewing. Nodding as he looked over at who had asked, he watched Hiccup sit down with a meal of his own. "I was hoping I would find you here, Astrid tells me you had quite the fun day at the stables."

This brought a slight blush to Tyler's face as he struggled to swallow his food as the man that held the key to his cock, as well as being his Dom for his stay, was sitting near him without a shirt of his own on. His toned abs and well-formed figure caused Tyler's cock to try and escape its cage.

"Y...Yes, Master. She is a wonderful trainer and I easily lost myself in the role." Hiccup nodded at that, starting to eat his own meal.

"Then I'm glad I suggested she take you for the day." With that, the two continued to eat in silence, Tyler having a hard time looking away from Hiccup as the other man sat there.

"Tomorrow I'm going to be busy with something all day so I was thinking of letting you have a free day in order to explore the island. How does that sound Toothless?" Hiccup asked as they finished eating their meals.

"Oh...Uhm, ya. I mean Yes Master, that sounds like a good idea." Tyler quickly answered, being broken out of his mental ogling of Hiccup.

"Ya know, when we aren't in a session you can just call me Hiccup."

"Are you sure Sir?"

"One hundred percent. And that goes for any of the Dom's here. If it isn't a session, no need to be so formal." Hiccup explained to him, leaning back in his chair.

"Ok... Hiccup." They sat there for another moment or two before Hiccup's watch started to vibrate. Looking down at it he sighed.

"I have to go, it seems my job is never over." Standing up and collecting both his and Tyler's trays, Hiccup would make to leave. "Have a good night and tomorrow Toothless." Before Tyler could respond or even offer to take the trays, Hiccup had left. Leaning back in his chair and running his fingers through his black hair, Tyler would let out a deep sigh.

"Ahhh, Fuck! Why does he make me feel like that?" He asked himself as he groaned from how hard his cock had gotten. It seemed that while it was caged it seemed to be easier to turn on than before. Grunting as he stood up, Tyler would head back to his room to try and mull over the raging emotional battle being waged inside him right now.