2Hey there guys and gals, yes I know this isn't a new chapter for FTDATT but Vala gave me this wonderful idea and it started living in my head rent-free till I did something about it. So here we are, my first lewd story. Are ya happy now Vala?! Without any further ado, let the fun begin with my very first lewd story. Hope y'all enjoy it! P.S. No A/N's till the very end.
Warning: This chapter starts with sexual abuse
0-0-0-0-0-0-0-0-0-0-0-0-0-0-0-0-0-0
WHACK
The meaty whack of a riding crop hitting flesh echoed for a moment through the playroom, followed quickly by a moan from the man which the leather tip had struck. His body quivered slightly against the restraints of the X-cross he was bound to, leaving him stuck standing in a spread eagle position.
WHACK
This hit brought forth a yelp from the black-haired male, as the crop hit the exact same spot on his rear. The pale flesh had already turned a bright red from the multiple, rapid hits. With a smirk, the large muscular male holding the crop brought it up to trace alongside the bound man's face a moment in a loving way.
"See, that wasn't too hard was it?" Reaching forwards, the red-haired male would remove a ball gag from the others maw, allowing him to speak. "20 swats with the riding crop is letting you off easy."
"P..please Dagur, I can't take it anymore," With a soft croak, he pleaded.
"Ah Ah Ah, what did I say about calling me by my name while we are in here Ty?" With that, the crop would fly again and smack the other side of Tyler's ass. This brought out a soft scream from the smaller man.
"Sorry Master, but I need to stop," looking back as far as he could to try and look the other male in the eyes. His ass stung heavily, the swats that Dagur had laid onto his ass as punishment for some imaginary slight had been harder than ever before.
"That's not how this works love. I'm the one in charge, I decide when we stop." Reaching forwards, it was clear he was aiming to regag Tyler with the red ball gag that now hung around his neck. "And just for that, we are going to keep going till I'm happy."
"Ni..fht huphy." With a swift motion, Dagur silenced his submissive lover and boyfriend and pushed his head forwards again. The ball gag kept any coherent words from coming out of his mouth. Both protesting the rough treatment and the safe word that the pair had agreed upon, Night Fury. Tyler thought maybe Dagur hadn't heard him and kept trying to say it. "Ni ury...Nigh Ury!"
WHACK
"Silence! I heard you the first time bitch, but I'm not done yet," The well-aimed hit coming underneath his ass and just behind the bound male's balls, a threat of what was to come as Tyler eeped out in pain from the sudden and rather hard hit.
WHACK
That swing of the crop landed home, directly on the exposed balls of the poor male now stuck at the mercy of his runaway Dom. This brought a scream to his lips, the ball gag making sure it wouldn't be too loud and disturb anybody.
WHACK
Dagur would start to speed up, alternating hits between the already bright red ass and the rapidly turning red balls of the man that was bound before him. Not that he cared, Tyler was his sub. His toy to play with and he was just letting the man know that he wouldn't stand to be questioned or denied his fun.
WHACK
"You will always be mine,"
WHACK
"My.." WHACK "..Little.." WHACK "..Bondage.." WHACK "..SLUT!"
By this time, Tyler would be overwhelmed by the pain and be hanging limp from the restraints. Not that the short chains and leather cuffs would let him fall far as they held his body up and his legs apart for the continued abuse by the crop at the hand of Dagur.
WHACK!
With one final hit, the now panting Dagur lowered the crop and looked down to observe his handy work. His sub's rear end and balls were glowing red from the punishment they had just endured. In addition, the crop had left small cuts along his rear, which were leaking small amounts of blood not only down his ass but onto the crop when it hit near them.
"Let's get you down and continue our fun." He said, reaching to undo the ankle cuffs, then the wrist cuffs. Tyler however, wasn't in much of a shape to stand as he sort of slumped into Dagur's arms. He would soon remove the ball gag, the red rubber gag was soaked in slobber that had flowed down the smaller male's chest.
"Get off me," Dagur grumbled as he let go of his limp lover. Tyler sagged to the floor and gritted his teeth as part of his injured body made contact with the cold damp floor. His mind was somewhat disoriented but Tyler did reach up to undo the ball gag. The red lines on his wrists from the cuffs are visible in his purview.
"Did I give you permission to remove that?" Dagur growled as the bloody riding crop smacked at the back of Tyler's palm. Tyler's gaze towards his boyfriend was anything but friendly and Dagur tisked at him before turning to a nearby table and grabbing a towel. "You know what? You're boring me tonight," Dagur stated as he threw the towel at Tyler. "Clean yourself up and get out of here."
Tyler, who had managed to undo the ballgag's buckle and toss the gag to the side, shouted "That's all you have to say?! Why didn't you stop?!"
"Why would I need to?" Dagur just shrugged as he walked to the stairs to leave the basement sex dungeon. "I wasn't done with you."
"Because I used our safeword!" Tyler yelled and then winced as he tried to stand up, being forced to use the X-cross as support to stand up and take a step after the man. "You promised me that you'd stop!"
Dagur, clearly not liking to be argued with, took his hand off the railing and walked back to Tyler, getting in his face and causing him to take a step back. His back was now against the cross as he was forced to look up at Dagur. "Listen here you little slut." Dagur growled. "You. Belong. To. Me!" He emphasized. "When we first met you were the one all over me asking me to do this to you so don't come whining now!"
"We're through Dagur!" Tyler shouted and pushed the other man off of him so he could leave. Moving as quickly as he could to the exit, he grabbed his clothing by the stairs and quickly put on his clothes, hissing as the wounds that Dagur had caused on his rear were bleeding and quite painful to put clothing over.
Dagur for his part just crossed his arms while watching Tyler get dressed. "You'll be back," He told the other as Tyler finished and went to march up the stairs. "You'll be back and you'll be begging for me to do this to you again. Let's face it. You're a painslut and you should know your place as a submissive Beneath me."
"And you're a douchebag! I can't believe I ever liked you!" Tyler yelled in tears before storming off up the stairs, making sure he slammed the door at the top as hard as he could. Walking through his now ex-master and boyfriend's home, there would be several photos of the two of them together. They would be taunting him as he started to move faster towards the front door, tears starting to form in his eyes as he barged his way out the front door and towards his car.
Opening the door, he would let out a loud hiss as he sat down in the driver's seat. Not looking forward to the drive home and about ready to break down into tears, all he knew was that he needed to go. With a turn of the key, the engine roared to life and before it even had a chance to reach idle, Tyler slammed it into drive and roared away. He wouldn't get far though, as after a few blocks it became hard to see through the tears brought on by both the physical and emotional pain. Pulling his phone out, he called the only person he could think of to help him out. As the phone rang, Tyler would set off again with his phone on speaker.
"Hey there Ty, what's up? Shouldn't you be tied up with Dagur?" The voice came out of his phone, a slight hint of concern in her voice.
"I broke up with Dagur, he crossed a line," He managed to hiss out over the pain. "I need your help once I get back to my house."
"What did that yak-brained idiot do this time?" In the background, he could hear the shuffling of feet and clanging of keys. "And why do you sound in pain?"
"Just meet me at my house, bring a first aid kit." By this point Tyler had to pull over again, yelling in pain and knocking his phone off his lap by accident. Unable to hear what the response was from who he called, he just kept driving. Every so often he would have to stop and pull over, the pain from sitting on his tender ass and balls forcing pauses. This would cause the normally ten-minute driver to take twice as long.
Pulling up to his house, he could see her car was already parked out front, but her blonde hair wasn't inside it which meant she must have been at the front door or even inside already. Pulling into his driveway would bring a hiss as he went over the curb, the pain distracting him for long enough that he almost drove into his garage door. Sitting there, he turned the car off and popped the door open as he tried to collect himself to try and get up.
"Tyler!" The voice called out as a blonde head came around the corner, all but rushing to the car to help him out. "Use my arm." While it was more of an offer, she jammed it around him and lifted him out of his car. Leaving him barely enough time to grab his keys from the ignition before he was dragged inside his own home. Taking care not to drop him on his ass, she helped him into his room.
"Strip those off or I will." She said, gesturing towards his pants not really leaving room for argument while reaching for a bottle of antibacterial gel.
"Cami!" Tyler sputtered, a blush forming on his face but he complied and started to peel his jeans off. Hissing softly, the bottom of his underwear was now red from the multiple cuts. Behind him, Cami would gasp, seeing the white underwear having turned mostly read from the blood they absorbed. Reaching out, she helped Tyler pull them off as they had started to stick to his cuts in some places before laying him down on his bed face first.
"This is embarrassing." Tyler would say, hissing softly in pain as his closest friend started to clean the multiple cuts on his ass. Dagur at least had the sense to not cause cuts on his balls but he still gave them a pounding.
"You're telling me, I didn't realize your ass was larger than mine,"
"CAMI! That's not what I meant," By this point, a blush was forming on Tyler's face to go along with the pain.
"I know, but Thor damn it. How have I never seen you in booty shorts or anything that shows off that ass? You've been holding out on me."
"I thought you were a lesbian?!" Tyler sputtered out, the burn from the antibacterial gel starting to go down.
"Oh I am, but that doesn't mean I can't admire a great ass when I see it," Came her response, which only got Tyler's face even redder. Not that she could see his face at the moment as he buried it in his pillow. "There, now that your ass is dealt with, out with it."
"Help me to the couch and I will," Tyler told her, which she reluctantly did before vanishing into the kitchen for a moment and returning with two cartons of ice cream and two spoons. For which she got a look from Tyler.
"What? Ice cream makes everything better, and I got you your favorite," She would say in an almost sing-songy way as she set down a spoon and a carton of rocky road in front of him as she sat down on a nearby chair with her own cartoon of vanilla.
"And you went with plain old vanilla?" Giving her a questioning look, Tyler would pick up his ice cream and eat a spoon full.
"Hey, you can't beat the classics. Besides, this is about you not me so out with it." Pointing her spoon at her friend, Cami would sit back and start to eat her ice cream as well.
"Fine...There's not much to tell really, I broke up with him because he's a massive jerk and it took till now to see it."
"And?" Looking away, Tyler would start to eat more of his Rocky Road. "Tyler, tell me what he did so I know just how much to hurt him."
"You wouldn't..."
"Oh but I would," came the mischievous answer from the blond sitting across from him. "I know your ass didn't get like that on its own."
"No...Dagur ignored our safe word."
"HE DID WHAT?!" Cami would shout out, clearly on the warpath now for some revenge. "Why that yak-brained idiot. Why would he do that?"
"He said that he owned me, and I was just there to serve his pleasure to his end, not mine," Tyler answered, His eyes glued to his cartoon of ice cream as he swirled his spoon in it to get small bits of the frozen sweetness. Meanwhile, Cami was taking large chunks out of hers in a vain attempt to try and calm down after being told what had happened and why. "Cami, I mean it. Don't go and try to get revenge against him for me."
"Oh come on, you know I have to." Came would pout jokingly, having already made up her mind that she was going to do something. "And it's not like you could stop me if I tried."
"You're right. Just keep it tame, I don't need him retaliating against me." Dagur was one of the local Bank managers, something he could easily use to leverage against Tyler if properly motivated.
"Oh don't worry. He won't be a problem for anybody after I'm done with him." The smirk on her face told Tyler that he should probably stop asking questions and just go back to his Rocky Road and let the ice cream wash away the pain and sadness of all those years together now being worth nothing. They would continue to eat the ice cream in silence, for a few moments before Tyler spoke up.
"So what am I supposed to do now?" He would ask, looking up from his ice cream to the multiple pictures of Dagur and him together that were strung around the house.
"Want my opinion? I know of a kink resort that you can go to." This response from Cami caused him to almost choke on his next spoon of ice cream.
"What?! You can't be serious. A Kink resort is the last place I should be right now."
"No, it's the first thing...after ice cream...that you need right now." Pointing her spoon at the male laying on the couch across from her. "Dagur treated you like crap, you deserve to see how a proper dom treats their subs. And who knows, you might find a few new kinks you didn't know you liked. I know I certainly did."
"Of course, you've been there." Tyler rolled his eyes at his friend.
"What? It's how I found out that I like to watch." Came the response as she pulled out her phone. "There, I just sent you them." Tyler's phone would ding a moment later as the text Cami sent arrived. Picking it up, he would look at, surprisingly, a URL for this kink resort she was talking about.
" .ck? They have a website?"
"It's the Internet age. Of course, they have a website," Cami uttered while rolling her eyes. "You can order sex toys and furniture off of Amazon for Thor's sake!"
"Ya ya," Tyler responded as he clicked the link, taking him to a rather well-made home page for The Kink Sanctuary. He would spend a few minutes looking around the website before Cami cleared her throat and got his attention.
"So? Have you booked your trip yet?" Cami asked, never the one for subtlety, as he was debating clicking the 'Book Now' button.
"CAMI!"
"Oh come on Ty, we both know you want to. It'll be good for you and get you out of the house and away from Dagur for a while. A good way to clear the head, both of them if ya know what I mean." That would cause Tyler to blush, still not quite used to talking about those things with her.
"Fine, fine. I'll book a trip if you promise not to follow me down there." This would draw a pout from Cami.
"Oh, you're no fun, fine." She would huff out. "But I'm helping you pack."
"Deal," Tyler said though he was sure he would regret it in one way or another.
-0-0-
"I can't believe she talked me into this," Tyler muttered to himself as he stepped off the boat that had taken him from the airport to the marina for the private islands that made up The Kink Sanctuary. The entire complex was on its own island, something that allowed it to operate as someplace where you could wander around in all forms of undress and kink gear. Truly a sanctuary for those looking to explore new kinks or simply indulge themselves in the more carnal pleasures. Standing near the front gate was a pair of blonde twins wearing identical uniforms, that of old school bellhop uniforms with green jackets, black pants, and gold buttons and accents. Something that Tyler had not expected then to look like for such a resort.
"Welcome to..." The female started.
"...The Kink Sanctuary!" The male finished, the pair in a large dramatic show then started to open the large main gate that led into the resort itself.
"In ya go, we don't want to let all the kinky out now do we?" The male twin said with a suspicious smile, prompting him to move inside the main gate and into the courtyard. In front of them was a large fountain which shocked some, as it was a large cock with water spurting out of the tip and down the shaft to pool around the balls at the base. The building behind it, however, wasn't as striking. A large Spanish-style structure that seemed to be both the main reception area and where all the rooms were. The gate shut behind him, causing Tyler to freeze as he was unwilling to take the first step forwards into what was deeply unfamiliar territory. After a few moments to take it all in, He would start heading for the front door. Opening it saw the inside look similar to a hotel, with a blond woman in what was a rather revealing outfit that left nothing to the imagination behind a reception desk.
"Welcome to the Kink Sanctuary! My name is Astrid and I'm one of the Dominatrix's here as well as your guide till you get to your room." Walking closer to the desk, he set his things down as he gulped while he did his best to look her in the eyes, a blush forming on his face. "Never been here before?"
"N...no, never. Had a friend convince me to book a stay." Tyler answered, still staring straight ahead. "The Uhm...The reservation should be under Toothless." He told her as she started to type it into the computer to find his reservation.
"It's okay to look, I don't mind at all. In fact, you might have a chance to see, touch, and taste even more if you want during your stay." Picking up something, Astrid would set a laptop down in front of Tyler. "First thing's first though, you need to fill out the checklist of kinks you wish to participate in and those you don't." Grabbing the computer, he would look down at the screen to see a questionnaire with several long pages which consisted entirely of different kinks in alphabetical order. Gulping slightly he would start with the first one 'Anal'. Standing off to the side in case somebody came in, it would take Tyler several minutes to go through every single kink on every page before he had finished the questionnaire and hit submit, and looked back up at Astrid.
"Was all that necessary?"
"Oh yes, it is required, it'll help us give you a more personal experience so we can fulfill all your needs." She would almost purr out the last bit, causing Tyler to blush deeper and shiver slightly. "Now, here is your room key. Don't lose it, it's also your ID badge for your trip." Setting a card down on the counter in front of him, it had both his name and room number on it, 'Toothless, 98'. "You'll be in room 98, it's on the first floor to the left about halfway down. A welcome packet will be waiting for you on your bed."
Nodding slowly, Tyler picked up his two suitcases and started to head toward his room. The inside was just as lewd as the outside, with multiple paintings and statues of suggestive or downright pornographic nature lining the hallways. Finding his room, he would open his door to reveal a room devoid of any sexual decoration. Kicking the door shut with his foot, he didn't notice that the door didn't fully latch shut. Though he did notice that the bed was a frame with multiple points for ropes to be tied to. Setting his bags down on the bed he had a look around. It was a well-equipped room with a single queen-sized bed, a couch, a TV, an attached bathroom, and everything one would expect from a top-tier resort and hotel. Indeed, just as Astrid had said there was a binder on the bed that had a picture of the resort under the words 'Welcome to Sanctuary!' on the front.
Deciding to read it once he had finished unpacking, Tyler set it aside so he could put his suitcases on the bed. Unpacking the first suitcase was easy as it was just casual clothes, all of which went into the dresser. In the second suitcase, he had let Cami help pack some more classy clothes in case he went to one of the many high-class dining places on the island, and not at all in case he went on a date. Reaching in he felt something hard, which when he dug slightly he was able to uncover.
"You have got to be kidding me!" Tyler called out, pulling from the suitcase a large tarnished bronze-colored dildo. "How did I not notice her packing this?" The dildo in question was a large Flint from Bad-Dragon, the largest dildo in his collection and one he had received as a joke several years prior and had never been able to get inside him. He would soon get distracted by a faint knock and the sound of the door swinging open. Standing in the doorway would be a man wearing a rather nice suit, his auburn hair down around his ears.
"I'm sorry, I didn't mean to interrupt you or anything." He started, startling Tyler even more and causing him to eep and toss the dildo aside. Well, he attempted to toss it into the closet and out of view but missed and ended up tossing it right at the feet of the man in his doorway, who casually picked it up and looked it over before taking a step inside the room.
"I'm sorry!" Tyler almost shouts as he comes closer to get the dildo from the man.
"You can take this whole thing?" The other man asked while holding it out for him. Blushing, Tyler took it back from him.
"N..no."
"Well, would you like to?" This caused the blush on Tyler's face to deepen and him to sputter even more. There was no real response from him as he stood there with the dildo still clutched in his hands. "First time here then?" The auburn-haired man asked him, having looked him over. Tyler gave a short nod and took a step back as the blush started to go away.
"Well then welcome! I'm part of the staff here, my name is Hiccup." Extending his hand for a shake, Tyler would start to shake before realizing he was extending the dildo in his hand. A soft chuckle came from Hiccup and Tyler started blushing deeply again before tossing the dildo onto the bed and shaking the other man's hand.
"Ty...Toothless...But you can call me Toothy during play." Remembering that the retreat had people using nicknames to not have to share their real names. This meant the staff would be using fake names as well, though what kind of a nickname Hiccup is wasn't really up for debate given his was Toothless.
"Pleasure to meet you Toothless, I just wanted to stop by and see how you were doing. Based on what you selected on the questionnaire the system matched you with me." Hiccup explained, pulling a tablet from his side, he opened it to look at it. "Pet play, chastity, edging, bondage and I'm adding anal training based on that dildo."
That got Tyler to blush deeply as Hiccup went over the things he had put down as what he wanted the most. Though to hear it spoken aloud by somebody else, the very person who would be doing it to him did get his imagination running and this got a reaction from down below. Noticing the growing bulge in Tyler's pants, Hiccup would speak up casually as if it was the most normal thing ever. "I see your imagination just got a hold of you, would you like to start now, or do you want more time to unpack?"
"I...Uhm..." A now sputtering and blushing Tyler would gulp as he was given the option from the handsome man standing in front of him to either step into this opportunity or shirk away from it. Hiccup would stand patiently while he waited for him to make up his mind.
"I can go and come back later if you would like."
"NO!" Tyler shouted suddenly at the thought of Hiccup leaving. "I mean...we can start now if you would like Sir." While slightly taken aback by the sudden shout, Hiccup didn't waste any time after that.
"Well then, follow me." Turning, Hiccup gestured for Tyler to follow him, which the other man did after making sure he still had his ID/access card on him. "Since this is your first session, it'll mostly be me getting to know you and us setting up our limits as well as picking gear." Nodding in response, Tyler followed behind him as they weaved their way through the building till coming to a room marked "Puppy Play Room". Using his card, Hiccup swiped open the door and changed a sign that read Vacant to Occupied. Letting Tyler go in first, Hiccup would shut the door behind them. Looking around, Tyler would notice that the room indeed was set up for pet play. The floor was padded to make walking on your hands and knees safe, as well as having bone-shaped toys and decorations all around. In one corner was a large dog cage, while on one of the walls was nothing but pup play gear. Hoods, collars, leashes, gloves, pads, tails, chastity cages, and even several different types and forms of bitch suits.
"It's a lot to take in for your first time isn't it, Toothless?" Hiccup asked him as he saw him stop just inside the doorway to take it all in. Nodding in return, Tyler would step further into the room before turning back to look at what would be his Dom and Master for the duration of his stay. "So, do you have any experience with pet play?"
"No Sir, but I've always wanted to try it out." He answers truthfully, looking down like Dagur had taught him.
"Alright, and you can look me in the eyes. I don't mind and even prefer it as it allows me to see what you're feeling." Stepping a bit closer, Hiccup still had not touched Tyler, but soon would as he raised his head. "Now, safe words. I noticed you wrote down Night Fury as yours. We take safe word usage seriously here, but also use a green, yellow, and red system. Have you heard of that before?"
"N..No I haven't," Tyler answered as he let Hiccup raise his head so they were looking at each other.
"Works like a stoplight. I'll ask you during the play how you feel. Green means you are okay and good to keep going. Yellow means to slow down and give you a moment. Red means to stop, and we'll talk about what happened. If you use your safe word that means you are done with our play and want out of any gear, bondage, or situation that you're in." Hiccup explained, Tyler nodding along as he was explained how it worked. "If you're gagged, it turns into tapping. One tap for green, two for yellow, three for red, and as fast as you can go for your safe word. Does that make sense to you Toothless?"
"That makes sense, It's more extensive than what I'm used to but it's simple."
"Good, that's what we designed it to be. Now, shall we get started?"
"Yes Sir... Or is it Master?" Tyler asked, canting his head to the side slightly as a curious dog would.
"Both work, but remember that dogs don't talk. I'll give you a pass as you aren't in any gear yet and the next part will be easier if you can answer me." Hiccup said, walking over to the wall of gear. "Now, since your favorite color is black then how about these?" Pulling a hood and collar from the wall, he showed the all-black neoprene gear to Tyler. Reaching for them, Tyler felt over both the hood and collar. Turning the hood over in his hands, he looked down at the dog-shaped neoprene that would soon cover his head.
"I think I'll look good wearing them," Came the answer as he handed the hood back, looking at the collar and the tag that hung from it. Shaped appropriately like a bone, it had a single word, Pup, engraved on one side. This caused him to blush slightly as the reality of what was about to happen dawned on him once again.
"Good, now strip. Pups don't wear clothes." Hiccup said, gesturing to the clothes that Tyler was still wearing.
"N...Now? Here?"
"Yes Pup, here and now. It'll be okay, the door is locked with the keycard so nobody else can come in." With a slightly nervous nod, Tyler would start to pull his shirt off up and over his head, revealing his rather well-toned chest and abs to Hiccup. Setting it aside, he would nervously reach for his pants and remove them as well to leave himself standing in just his underwear. Looking up at Hiccup, he saw that he had looked over his body to see what he had to work with but did not have the same predatory gaze that Dagur used to have. Taking a short deep breath, Tyler removed the rest of his clothes so that he was standing in front of his Dom for his stay in the nude. "You look good Toothless, let's get your hood and collar on shall we? Then maybe see which chastity cage you'll like and will fit you."
"Yes, Master," walking up a bit closer, Tyler would accept the collar and put it around his neck. Making sure it was nice and snug, but not tight enough to choke him, he soon reached for the hood Hiccup was also holding out for him. Looking it over once again, he started to pull it over his head.
"Remember, once the hood is on you are a puppy, so no talking and you should be on all fours." Stopping for a moment, Tyler would nod to Hiccup and then finish putting the hood on his head. Making sure it was settled in place, Tyler would get down onto his hands and knees. The padded floor meant it wouldn't be painful for extended play.
"Such a good boy," Hiccup would say, leaning over slightly to pet Tyler's head softly. This would cause Tyler to yip softly and nuzzle into the petting. "Now, would you like to get a look at the chastity cages?"
Looking up at Hiccup, Tyler would give a wag of his rear to indicate he would like to get a look at them. Smiling, Hiccup would lead him to another part of the wall where he would open a drawer that held the base rings. "Rollover and let me get a look at your cock so we can get this cage on, okay pup?"
Slightly nervous, Tyler started to do as he was told by rolling onto his back and spreading his legs so that his Master could have easy access to his cock. Crouching down, Hiccup would touch Tyler's cock for the first time. Feeling his balls and slowly hardening cock in his hand, he would head back to the drawer and grab a base ring. Coming back, he would like it over his pup's cock and balls till it sat flush against his groin. Wiggling a finger between the ring and Tyler's groin, he would look up at his sub's face. "Not too tight is it pup?"
Shaking his head, Tyler let him know it wasn't too tight. It was an interesting sensation for the new pup, the ring nice and snug against his groin. Looking down at his semi-hard cock as Hiccup went to grab a cage, he would see the stainless steel ring to which the cage would attach too. Returning with a metal cage, Hiccup would show it to Tyler before heading down to his cock. It was a simple bar cage, with both horizontal and vertical bars to keep the cock inside nice and secure. Tyler would give a soft shudder from the cold steel that Hiccup was pushing onto his cock. It would soften his cock a bit, making it easier for Hiccup to get the cage onto the base ring. The single bar on the base ring going through a hole in the top of the cage. Pulling out a small padlock, he would thread it through the holes and then lock it, making sure the only person who could take it off was Hiccup who had the key.
"There ya go pup, your very first chastity cage. How does it feel?" Hiccup asked, kneeling next to Tyler, who sat up to look at his caged and locked cock. Indeed it was a strange new feeling, a metal cage keeping his cock from getting hard. Looking up at Hiccup, he would bark softly to let him know it felt good. "I'll take that as a positive, still green light?" Tyler nodded in response to that, letting his owner know he was still doing good. Reaching for a different drawer, Hiccup pulled out an anal plug that had a puppy tail attached to the end of it.
"So, how do you feel about having a tail and we can start your anal training?" Tyler would look up at the plug in Hiccup's hand. His cock would strain slightly against his cage at the thought of the plug being in his rear. Yipping softly, Tyler would move to be back on his hands and knees, turning to present his rear for Hiccup. With the hood on hiding his face, and starting to feel more comfortable in the situation, and with Hiccup, Tyler was starting to get into being a pup and being lewd with his owner. Chuckling softly, Hiccup would grab some lube and spread it over the plug. Kneeling behind Tyler, he would spread his ass cheeks to get a view of his pup's ass.
Bringing the plug in closer, he would start to rub it around Tyler's ass to spread the lube. This would bring out a soft shudder from the male, but also a moan as Hiccup started to push it into his ass properly. Tyler was no stranger to having plugs, dildos, cocks, and fists being pushed into his rear so the medium-sized plug went in without much resistance. With a gasp from Tyler, the remainder of the plug slid in so the base with the tail was the only thing sticking out. Now Tyler looked even more like a pup, with a rubber tail behind him to match the hood and collar.
Clenching his rear around the plug, Tyler looked back to see the black rubber tail sticking up from his rear. Waggling his rear, the tail would also start to wag behind him. Even when he stopped the tail would go for a little bit longer before stopping. Smiling, he would look up at Hiccup who was standing now on the other side of the room smiling. Patting his thighs, Hiccup would call from him. Barking softly, Tyler would crawl over to where he was. Kneeling as he got closer, Hiccup would allow Tyler to leap up with his hands onto Hiccup and bark happily, wagging his tail behind him.
"Such a good boy Toothless!" Hiccup said, petting his head as he looked over his pup. In his line of work, Hiccup had been the owner of many different pets, however, there was something different about this one. Somewhere deep inside he felt something welling up that he had not felt about one of his clients before. Pushing it back down to examine later, he got back to work. Unknown to him, Tyler was having similar thoughts. However, he was holding them back as Dagur had left a bad taste in his mouth and he didn't want to be burned again.