A Puppy’s Unexpected Surprise – Miss Alyss & GoodbyeSkyHarbor

[Nine of Hartz]

It was well known throughout the kink community that there were various sites that posted ‘wanted ads’ from kinksters looking for others to share in their fun. On one of such sites, there was simple ad that didn’t stand out screaming to be acknowledged, but was rather simple and plain to the common eye. It wasn’t meant to attract just any typical sub, but a unsuspecting puppy.

-=Domme Female seeks pet puppy. Seeking to do public and private scenes at Club Thai Mi Up on weekends. Must be a submissive that enjoys the follow: being pegged and anally trained, restrained or suspended with shibari, willing to partake in a bondage lifestyle, partaking in pet play, and orally satisfying his Mistress per Her command.=-​

After careful review of multiple requests for a meet up, the woman who had posted the add had finally combed down the results to just a few candidates. She mused over them for a week, testing and taunting the respondents before agreeing to have a ‘demo session’ to test whether or not things would work. Never giving them her name, she simply texted them instructions of where and when they needed to be from a disposable pay as you go phone.

Go to Thai Me Up. Arrive promptly at 7pm and ask for the key to Room 1237 at the bar. I will be waiting.​

This evening was going to be with a ‘puppy’.

The entrance to Thai Me Up seemed to be a typical bar and restaurant. It was a well-known and established kink club within the city, but also blended in with vanilla society via the front entrance. Past the bar was a door guarded by a bouncer whom only allowed guests with antique keys to pass. Once through that door, you would enter a large room filled with various play equipment for scenes more public in nature. Past this room was a long corridor hallway with cage-like closets to the right, doors to the right that led to private rooms that could be rented. Muffled sounds could be heard within the hallway, occasional smacks and screams echoing through the vacant hallway.

Room 1237 was halfway down the hall, a good starter room for anyone who was new to the club and was empty for the ‘puppy’ to explore before She arrived. It contained a Saint Andrew’s Cross, bars for suspension, a saddle, large dresser full of gear, and lots of open space for larger activities. There was also a bed stuffed off the side, equipped with large posts with rings for various positions. It was in such a place that this evening’s festivities would transcribe.

 

[GoodbyeSkyHarbor]

Oliver sat in his room alone, staring at himself in his mirror. He wanted everything to be perfect for her, his hair had just the right amount of product in it, his nails were trimmed, his clothes were perfect. He had even considered a small amount of make up, but thankfully decided it was a little too far.

He was an adult, but at 18, he was still considered a boy to most, and seeing as how this was his first foray into the world of sex clubs and a more "adult lifestyle", he'd never felt more like a child. The woman he was going to meet seemed better educated and more experienced than he, and it was making him more nervous than when he had lost his virginity. He had read and re-read the message so many times he had it memorized, he had touched himself many many times at the thought of what was going to happen to him tonight.

Oliver arrived at the club at 6:45, he had always been a punctual person. He got out of his car and sighed deep, his hands were shaking and his heart was beating out of his chest. He was really going to go through with this, he was here, this was it, what he had been dreaming of for years. His soon to be Mistress seemed fun and trustworthy, too!

He collected himself and headed inside, walking straight to the bartender and asking for the room key. The bartender looks him up and down and reaches under the counter, pulling out a old Victorian era key and slides it across the counter.

Go through those doors

The bartender points at the double doors leading to the play area.

The bouncers won't stop you as long as you show them the key. Its the 2nd door on the right.

Oliver nods and heads to the doors, holding up the key in front of him. The bouncers nod their heads and part, letting him in. He slips past them and heads down the hall, hearing the slaps and screams only get him more worked up. He opens the door and his eyes go wide at the sight of all the equipment! But it quickly dawns on him that the room is empty, She had yet to arrive. His heart sank, what if she had decided to blow him off?

He walked over and slumped down on the bed, deciding to wait at least a bit to see if She showed up.

 

[Nine of Hartz]

After a few minutes alone in the room, the door would suddenly click as a key was inserted into the lock, twisting to force the metal gears to shift and retreat from the door jam. The door swung open slowly, the click of heels heard on the stone floor of the hallway, the clicks muffled lightly once she stepped up onto the carpet of the room. Her eyes flicked up as she entered the room, making direct eye contact with the boy that was on the bed. A smirk immediately crept across her lips as she shut the door, it automatically locking so no one from the outside could enter.

Setting the antique key on an end table, she hung her black purse up on a hanger hook on the wall, slowly letting her white coat slide off of her shoulders. Hooking the collar of the coat on a hanger, her curvy torso was exposed for Oliver to see. Her breasts were plump, probably a C cup, and her hips were wide. Her belly was trim, the muscle hidden underneath the delicate pink blouse she wore. Tucking her loose black hair behind her ears, the color of her eyes was revealed. They were such a pale blue they appeared to be lavender in color. Her skirt was black, made from a fine netting like material that covered a black silk slip. Knee high leggings came up to her thighs, her boots resting just below her knees.

Taking a few steps toward Oliver, she lightly crossed her arms and looked him over a few more times as if she were rating him mentally. Her fingers lightly lifted to toy with a necklace around her throat, appropriately made of little chain pieces with a heart shaped handcuff on it. Lightly parting her lips, she spoke to him in a sultry husky tone. “Oliver I presume?” she watched his response before nodding lightly. “Until we are more properly acquainted, I will refrain from giving my name. You may address me as Ma’am for the time being.”

Extending her hand out to him, she lightly motioned at his street clothes. “I understand that you desire to be a puppy to me. Like any good boy, you’re going to need a collar.” Turning to face the back wall, she dug through her purse and pulled out a black leather collar. It was simple in design, but had a silver buckle at the end. Lightly holding it in her hand, she dangled it by the buckle and wiggled it side to side before Oliver’s face. “My rules are simple, you may wear the collar but you will not have My collar until you’ve proven yourself to be a good boy. Understand?” She lifted her brow at him before pulling the collar back.

“So, what would you like our first play date to start with Oliver?” She had requested a list from him to know what he would like to do in their play sessions, but she was curious as to how he would want to start their first session. “Do you want some basic puppy play to ease into your role, or perhaps something more vanilla?”

 

[GoodbyeSkyHarbor]

Oliver had started pacing the room while waiting for Her to arrive, looking over all the toys and equipment. He paused to stare at himself in the mirror for a moment, straitening out his jacket and plain white undershirt. His jeans were rather tight, but he liked them that way, it showed off his lower features well. He sighed deeply and walked back over to the bed, sitting down on it hard.

His heart skipped a beat when he heard the door click open. His head shot up, his eyes straining to get the first glimpse of Her. His eyes locked with Hers when she entered the room, and he instantly fell in love with her. She was gorgeous, as She slipped her coat off Oliver hungrily eyed Her up and down, She was the perfect woman. Curves had never meant so much to young Oliver, the slope from Her shoulders down past Her breasts and to Her dazzling hips alone was enough to make a man mad with lust.

His eyes drifted all over Her body in seconds. Her heart shaped bottom took the most time though, She had a perfect ass, to be sure. Her boots... Oliver had always had a thing for a girl in knee highs. His breath was coming in short, shallow, almost gasp like breaths. He was almost panting at her.

Then She turned around and pushed the hair from her face.

It was as if Oliver had been hit by a bombshell. His mind was sent reeling, Her eyes were the prettiest he had ever seen! And Her face! She was so amazing attractive, he felt like he was lucky to even be in the same room as this woman.

She walked over to him and asked him if he was, indeed, Oliver. All he could do was nod at her. She told him that he wasn't going to be told Her name, he thought it was bizarre at first, considering the reason for the meeting, but he didn't argue, how could he? He was told to call Her Ma'am. He cleared his throat quietly and shook his head again. "Yes Ma'am."

He watched and listened as She retrieved the collar from her purse. He nodded as She told him he had to earn Her collar. "Yes Ma'am, I understand completely." He said, with a faint smile, he was finally starting to regain his wits.

She continued on, actually asking him what he wanted to do first. He mulled the question over for a moment before standing up and walking towards Her. He realized too late that he had quite an erection, his jeans were bulging out and making it far too obvious for Her not to notice. He stopped for a moment and considered sitting back down and trying to nonchalantly cover it up, but knew that she had to of already seen it. He mustered all he had and walked towards Her as confidently as he could, speaking in as calm a voice as could be managed.

"Well, to be completely honest Ma'am, I didn't really come here for anything vanilla."

 

[Nine of Hartz]

She couldn’t help but smirk to herself as she heard his answer about not being there for vanilla activities. That was an answer she was enthralled to hear. The pleasure to his response was very noticeable to Oliver as well, not only from the smirk but in the way her eyes almost twinkled. With a swift nod, she closed the gap between them even further by taking a few steps forward. Lifting her hand, she gently patted his sandy locks as if she were rewarding him. “Good boy.” She said praising him before dropping her hand to his jacket, taking note of his erection.

Gently tugging the zipper of his jacket halfway down, she pulled the fabric away from his neck so she could easily access it. Lifting her hand that held the collar, her warm fingers slowly traced against the skin of his neck as she pulled the leather around his throat. Tucking the end of the collar into the buckle, she pulled it through and lightly fastened it, slipping her fingers inside to make sure that she could get three of her fingers in between the leather and his throat. It was something a Top always had to do when restraining their submissive, ensure that there was enough space to not cut off circulation.

Stepping backward, she gave the collar a light tug by the silver ring that was affixed to it for a leash to be placed. Letting her lavender eyes meet Oliver’s brown ones, she lightly smiled at him and motioned at his clothes. “Would you like to stay in your street clothes? Or would you like to slip into something else or nothing at all?” Walking toward the counter that had an array of toys, her fingers lightly ran across the array of goodies that called out to her. Lifting a simple leather harness up, she lightly whistled for Oliver as if he were a dog to come and look at it. “Personally, less clothing is better in my opinion so I can have better access to you, but I will let you stay in your comfort zone today.” She also pulled out a pair of knee pads, setting them out in front of him. “I don’t know if you want to wear these or not, but they are available if you would like them.”

Reaching to another cabinet, she opened it and revealed an array of tails with different butt plug attachments. There were some that were smaller meant for beginners, then much larger ones. “Do you have a preference for what type of tail you wear? A little one like a small dog tail or a bunny? Or do you like longer ones like a fox or husky?” Picking a black fox tail one that had a medium sized plug on it out from the cabinet, she sat it on the counter in front of Oliver. Also grabbing one with a smaller plug and a fluffy bunny tail, she sat that down as well and glanced at Oliver letting him look at those and the rest in the cabinet. She glanced at his ass and gave it a light squeeze as he looked at the toys. “I can always work you up to the medium sized butt plugs if you’re not experienced with them.”

Reaching toward another area, she pulled out a metal chain leash with a leather handle strap at the end. She lightly smacked the leather against her hand as if she intended to use it both as a leash and a little whip. Flicking her eyes over Oliver, she stood there waiting for his feedback. She could tell that he was eager due to his erection, and she was eager to start playing with her new puppy.

 

[GoodbyeSkyHarbor]

If Oliver actually had a tail it would be wagging. He was so excited to get any kind of praise from Her. He could tell she was actually praising him, there was something about her eyes. When she patted him on the head he was practically shaking with anticipation. He thanked her when she called him a good boy. He saw her eyes flick down and his cheeks turned red, she had noticed! He was so embarrassed!

His breath shortened when she went to place the collar on him. He strained his neck a little to make sure she could easily get it on him, he stood there dutifully as she locked it around his throat and gave it a bit of an, albeit unexpected, tug.

She grabbed his collar and focused his eyes on hers and smiled lightly at him, he was really beginning to like her, she had a... softness about her. And her eyes... they were so pretty! He bet she had a wonderful name, and was hoping that he would get to hear it soon.

Then she had, in so many words, asked him to get naked in front of her. He knew this would come, but it just seemed so, clinical? That felt like the word... She had told him he could stay dressed if he wanted, but he knew that she would be happier if he was nude. She went on to tell him about knee pads, but he wasn't interested. His parents had forced him to go to church every Sunday of his life, he was used to being on his knees.

He walked over to where she had whistled for him and surveyed all the tails before him. He picked up the fox tail that she sat in front of him. He ran his hands over the bulb part of the toy, wondering if she would be able to easily get it inside of him. AS he was mulling over the idea she grabbed his behind and he jumped forward a but, bumping into the table and moving things around a bit, she had caught him completely by surprise. He looked over at her and said "I've never used anything quite this large, but this tail is... attractive. I've always found foxes to be very sexy."

He thought for a moment longer and then started to undress, he decided he might as well keep going with his confident attitude and strip all the way down. He unzipped his jacket and pulled it off, he walked over to the bed and folded it, sitting it down. Next was his shirt, he took care not to interfere with the collar as much as he could, he folded it also. He unbuckled his belt and dropped his jeans, folding them over his arm and stacking them neatly on top of his shirt. He took a deep breath and pulled down his plaid boxers, his cock sprung up so hard it almost hit him in the face. He was as hard as a diamond down there. He straightened up and folded his under garments, placing them on top of his stack, before walking back over to Her.

 

[Nine of Hartz]

Her lavender eyes flicked over the fox tail and lightly picked it up once Oliver was done with it. “Yes, they are magnificent,” she said as she stroked the fur. “They are by far my favorite.” Lightly chuckling, she glanced at him as he began to walk toward the bed to undress. “Don’t worry - I’ll work you up to the tail. You’ll be ready for it.” Lightly biting her lower lip as she pondered various activities, she opened up a different drawer and pulled out a small bottle of silicon lubricant. It proved to be slicker than water based lubricants and she wouldn’t have to use as much, which was good because she wasn’t wanting to make a large mess...yet.

She turned to watch Oliver undress, noting how neatly he folded his clothes and placed them in a pile. Lightly musing to herself, she lightly smirked thinking that this new ‘puppy’ of hers might turn out to be a fun to be a ‘house pet’ if things were to go well between them. The thought of coming home to Oliver waiting at the doorway for her on his knees made her tingle. Watching him pull off his jeans and then the boxers, she lightly smirked seeing his young toned body and how ready he was for their session. There was just something about younger men that was thrilling to her, especially if they were inexperienced or shy in temperament.

Setting the tail down on the top of the shelves, she shut the drawers and put everything away so only the lube, tail, and leash were on the counter. Turning to face Oliver, she warmly smiled at him as her fingers went down to the bottom of her pink blouse. “Well, shall we begin?” she asked before pulling her blouse up and over her shoulders, revealing a lavender corset. It was delicate but still gave the impression that she was a Domme.

Reaching her hand out, she dropped her shirt on the floor and narrowed her eyes at him. “Put that away with the other clothes,” she said in a firm tone, clearly intending for him to fold it and put it with his clothes. As soon as he bent over to grab the blouse, her hand snuck down along his back and right to his ass. Her hand was warm on his skin, her fingers tenderly rubbing between his ass cheeks then down further to lightly stroke his balls. With a smirk, she gave Oliver’s ass a light smack to urge him forward to the bed. She grabbed the little bottle of lube and the tail, following him over to the bed. Setting the tail and lube beside the pile of clothes, she watched him fold the blouse and gripped him by the leather collar once he sat it on the bed. Without hesitating, she hooked her finger into the ring of the leather collar. “Lay down boy,” she coaxed him while tugging him down face first onto the bed.

Walking behind him, she rested both of her hands on his ass and spread his cheeks wide to glance down at his ass. A smirk crept across her lips as she noted that he had cleaned himself per her instructions, gently rubbing her thumb against his asshole as she glanced down at him. The way she had pushed him down onto the bed had forced his cock underneath his hips, and she lightly frowned. Resting her hands on his hips. “Up,” she said while gently tugging up as she spoke. Reaching underneath him, she ran her soft fingers down the length of his shaft, admiring how solid it was.

“Mmm, My poor puppy. Do I need to take him out for a ‘cum’ break?” She whispered out as she pulled his cock back, pushing his hips down so it would be hanging between his legs. Getting down on her knees, she gripped his ass and spread his cheeks open again. Her tongue reached out to lightly lick at the tip of Oliver’s hardened cock. Slowly dragging her tongue up his whole length, she then ran her tongue up between his balls and across his taint before swirling it against his asshole.

Without hesitating, she pulled her tongue back into her mouth to get it wet, extending it again so she could lick at Oliver’s tight asshole. Gently probing her tongue against him, her breathing got heavier as she pulled Oliver’s ass into her face, her tongue forcing itself inside of his tight depths. Working her tongue in and out of him, her fingers lightly kneaded at his ass as she waited for his reaction, occasionally dragging her tongue up and down along his cock before resuming thrusting into his asshole greedily with her tongue.

 

[GoodbyeSkyHarbor]

Oliver had never had his ass licked. He had asked his girlfriend Chelsea, but she had scoffed at him and joked about him being a "faggot." He HATED that word, and she knew it. But now that She was doing it... her tongue was so powerful and sleek, her hands on his hips and ass were subtly commanding, leading his body. As she flicked her tongue over his asshole he let out loud, vivid groans and moans. The tip of his cock was dripping precum, his balls were already swelling up.

She shoved her tongue inside of him and he gasped and fell forward, pushing his head into the sheets and moaning loudly. He looked back between his legs and saw her tongue hungrily lapping at his tight virgin asshole, it was truly a sight to behold. He was already trying to think of other things so he didn't come too quickly. But this woman was magic, if she continued this for too much longer he was going to cum all over the satin sheets.

Oliver's cock wasn't too massive, it was average at best. But she licked up his shaft so slowly... it made it seem like he was much bigger than it was. It was the best kind of agony, he wanted to turn around and just fuck her over the side of the bed, but he knew she wouldn't tolerate that. He was here to be dominated, he was here for this stranger, this... wonderful stranger, to take control of him.

He couldn't take it anymore, he was so close to cumming. He felt like he had to tell her, but he was so embarrassed by it. He knew he shouldn't be, but he felt like he was letting her down by cumming so quickly. Still, he had to say something, surely cumming without telling her would be much worse.

"Ma'am... I... I think I'm going to cum soon, is that okay?"

He asked meekly, he lifted his head and looked over his shoulder, all he could see was the top of her head as her tongue was buried deep inside of him. He hoped she would answer soon, otherwise there would be a mess.