This Friday night, like most of Taylor’s Friday nights, was a miserable failure.

Taylor had been traveling for work, as he seemed to do a lot of these days. He had a decently paying job, a neat and serviceable little apartment, and a relatively staid routine that normally kept him in the office fairly late even when not traveling. He didn’t mind it especially, being so busy, as it neatly distracted him from the dearth of a social life. He’d always been a bit of a recluse, until the recent pandemic had turned such hermit-like inclinations up to eleven. Ever since he’d just been unable to reacquire the habit of going out after work with colleagues or friends, maintaining hobbies, or even trying to go on dates. Normally it didn’t bother him. Normally work kept him pleasantly busy, and his mind firmly on professional matters.

But this particular trip had been different. He had made a genuine effort to connect with someone. Chatting with Rachel online via a dating app, things seemed to have been going relatively well. They had had some mutual interests in gaming and reading. Taylor had made her laugh with some of his jokes. Rachel had seemed like a thoughtful and reasonably interesting person. She had even been interested in him too! Taylor was not especially used to women finding him super attractive, but Rachel had made him feel those light-headed heart skipping moments of joy that came with that feeling. She had, overall, been a wonderful sort to encounter. The sort of person who would definitely show up for a first date.

And yet, here Taylor sat. Almost two hours after their agreed meeting time, and no trace of the delightful brunette with mischievous eyes that he had seen in his chats. No sign of anyone his age entering the hotel bar. Nothing for Taylor to do but drink, and wait, and hope. Which was mostly what he had been doing for the past two hours, remonstrating with himself about what he might have done, what small offence might have caused Rachel to reconsider and ghost him. It had to have been something on his end after all, Taylor couldn’t conceive of someone simply stringing him along, or being so rude as to change plans and not have the decency to let him know.

So there he sat, stewing in angst, failure, and the first flutterings of romantic despair. He had looked around the hotel bar, torn between heading up to his room to go to bed, or remaining in place to drink and be morose for another hour or more, when he suddenly spotted her.

Not Rachel, someone else.

A gorgeous older woman was sitting at the bar, chit-chatting with the bartender. She was dressed in an elegant green floral patterned dress, light and swirling that reached down to the mid-calf, accented by a broad brown leather belt, and soft brown leather boots. Her hair was cut in a shoulder length bob, and she was absently playing with it as Taylor watched. She wore glasses perched forward on her nose, and her lilting laugh and smile made Taylor grin a little despite himself.

Taylor felt himself swallow. A woman so far out of his league that he’d no doubt need a telescope just to see where she stood. Probably quite confident given how she was carrying herself. She’d take the lead. Perhaps picking where they would go, what they would do, what they would talk about. Taylor felt his lips quirk, his eyes and mind still lost in reverie. That actually sounded rather nice. That was the difficulty with girls his own age after all. He was meant to be the one to be forthright and decisive, when all he really wanted was someone else to do those things. Someone else to make the decisions. Someone else to make the first move. Someone like that, confident, elegant, and supremely attractive was what he longed for, but there was absolutely no way in hell she would ever…

The woman looked over. Spotted Taylor’s less than discrete stare. He began to blush…and then she arched an eyebrow, setting her drink aside to stare back at him.

God could this night get any bloody worse?

Taylor tore his eyes away, face flaming red in embarrassment, and buried himself back into his drink.

He squirmed a little further back into the padded bench of the booth he was in, trying to get out of the woman’s direct line of sight. He had been caught ogling her. He felt flushed embarrassment coursing through him, knowing he had been so boorish to be caught staring at her. Just because he was having an awful night didn’t mean he had to make someone else uncomfortable. He should go. He should go back to his room, and call this night before something even more mortifying happened.

Taylor drained the last of his nursed pint and began to shimmy towards the end of the booth, only to have a swirl of green and browns suddenly block him in.

“Leaving so soon?”

Taylor blinked, his eyes traveling up to find the woman there. Her eyes twinkling behind her glasses, an amused and knowing smirk on her face. One hand leaning on the table, the other settled on the back of the padded bench. Trapping Taylor in place. His eyes tracked up her voluptuous figure, unable to stop from clinging to her curves, her busty, fit figure, until they reached her face again. Those red lips, twisted in a slight grin, made almost mischievous by the inquiring, playful twinkle in her eye. And those eyes! Some combination of dark forest green with flecks of brown and orange. As though autumn had made a home in her head and peered out at the world from those twin portals.

His shocked and somewhat off-balance silence allowed the still nameless woman to brush a hand briefly across his shoulder, before settling into the booth seat across from Taylor. Her demeanor radiated amused satisfaction at Taylor’s continued speechless goggling at her, and she arched that commanding eyebrow again, “I believe its customary to introduce oneself to a lady upon first meeting…especially when one has been staring at the lady in question…”

A renewed furious blush raged across Taylor’s face, and he twitched and stammered for endless moments before he managed to finally croak out his name.

“Mmmm, delighted. I…am Jillian Daylish.” She steepled her hands in front of her, leaning forward to rest her chin on them. She looked so delightfully approachable in that moment that Taylor briefly forgot for several seconds that she was only over here because he’d been caught staring. “So…Taylor. What’s a handsome fellow like you doing here staring at someone like me?”

“I’m sorry, I shouldn’t have—”

“Did I ask for an apology?” Jillian quirked her eyebrow again, “I’m asking for an explanation. I imagine you’re not the boorish type, squirreled away in this little corner booth. I don’t know you especially well, but you don’t strike me as some creep little pervert. So…”

The impetus to confess was simply too much for Taylor to resist. He found himself slumping down into the booth, his mouth unmoored from his still fractious thoughts, and spinning his tale of romantic woe to this complete stranger. How he was an introverted workaholic. How he’d been having truly rotten luck with dating girls. How his most recent date had stood him up, and why he’d been looking across the bar at Jillian in her elegant attire and confident demeanor.

For her part, Jillian accepted the entirety of the story with a sympathetic expression, “Well you did seem fairly glum when I looked over…apart from the fire truck blush you’ve got going on.”

Taylor’s face heated again, and her gentle laugh and hand pat on his arm took the potential sting out of her words, “Listen. I’ve a room here as well, and am also passing through on business. I detest eating alone. Since you’re also having a less than ideal evening, I thought it might make it up to both of us if you joined me as my evening companion…”

“Oh, uhm, I…” Taylor floundered for a moment, his evening suddenly shooting straight upwards in terms of potential. Jillian wanted to spend time with him? Hell, have a meal with him? Talk more? Spend hours yet getting to be around this amazingly empathetic and beautiful woman…it was practically a trick question. There was no way that he could turn this down. “I’d love that!”

Jillian returned his smile with a winning one of her own, stroking his hand for a few glorious moments as her eyes twinkled, “Splendid. It’s settled. You’re mine now.”

An odd way of putting it, but Taylor was loath to do or say anything that might detract from this quasi magical evening. That a woman like Jillian was talking to him was boon enough, that she had decided he was to be her compatriot for an entire evening was something else.

Taylor didn’t pay much attention to the mechanics of what came next. Jillian seemed to know her way about things, flagging down the wait staff to obtain a succession of drink orders and an array of small but tasty food dishes. As the drinks and food came and went, Jillian gracefully carried the burden of the conversational topics. Artfully shifting from one theme to another, plucking details about Taylor from him like a farmer obtaining only the best apples from her orchard. She listened as he talked about his life. She expressed delight in his hobbies, especially some of the novels he had been reading. This in turn further relaxed Taylor, and he felt it only natural to begin talking about why he liked certain aspects of those books. Why he lost himself in fantasy and science fiction so often.

“It’s not so much an escape,” he started and then grunted with a half chuckle as Jillian nudged him with her foot, “What?”

“There’s nothing wrong with escapism silly boy,” Jilian giggled, her own cheeks a trifle flushed from her wine, “Escapism is a part of the human experience. Hell, life can be plenty crappy sometimes, and I defy anyone to claim that they’ve not wanted to trot along into the woods and lose themselves in a magical adventure. The real world can be dreadfully dull on occasion…”

Taylor flushed, “Well, yes, I-I mean…” he took a breath, and then lost it in a fit of nervous coughing and giggles as Jillian oh-so-innocently ran her foot down his calf.

“I’m sorry…” Jillian’s smile widened, her eyes sparkling, “I seem to keep interrupting you…”

Taylor swallowed, but resisted the urge to jerk his leg away and instead met Jillian’s teasing expression with what he hoped was a confident look. Her smile widened a trifle, and she murmured something softly. Taylor was sure it couldn’t have been what it sounded like “good boy” since that didn’t make much sense. But she wasn’t removing her slowly moving foot from touching his calf, so he rallied himself as best he could to continue to talk to her. Though he had by this point forgotten the angst of being stood-up by the elusive Rachel, he couldn’t help but find himself talking to Jillian about why it was that he seemed to be so ill favoured romantically.

“I really just…” he gestured with frustration, “I dunno…I wish life was like books. People always explain themselves, or just understand their love interest after a while. Yeah sometimes they go through things, but eventually circumstances, life, whatever you want to call it, bring people together who just seem made for each other…”

He flushed and took a long pull from his pint of local beer, face flushed with a combination of nerves and alcohol, “I think my life would be a lot simpler if…”

“If what?” Jillian ran another teasing foot over his leg. They both giggled as she wiggled her eyebrows at him, “sounds a bit like you want the lady to make the first move…”

Taylor flushed, opening his mouth though unsure what it was he wanted to say in response.

“That’s okay,” Jillian smiled, waving a lazy hand at herself, “For me I get rather tired of the bravado that so often accompanies males when they try to hit on me. I much prefer the shy types who understand their place…taking their lead from me, so to speak.”

She locked eyes with Taylor then. Dense though he thought himself to be when it came to women, even Taylor couldn’t fail to make the connection. He was being precisely what she wanted him to be. He was her type…and she was most definitely his.

Taylor swallowed, feeling her booted foot trace up his leg. He felt his face heat in time with the movements of her foot, as it moved past his calf. Trailing teasingly along his inner thigh…and settled firmly in between his legs. The flat toe of her boot pressing gently but firmly into his soft but rapidly stiffening cock. Taylor’s mouth parted slightly, as he gazed at her with a mixture of horror, embarrassment, and gathering arousal.

“I…you…your f-f-f…I…”

“Come now darling, we just got through quite a bit of chat, the crux of which seems to me that you enjoy when a woman takes control. You aren’t especially talented at placing yourself with your best foot forward…so here I am, placing my foot forward. No.” She wagged a finger as Taylor shifted, “No getting up. No retreating. And certainly no demands. We’re going to sit here and talk, and my foot is going to remain right where it is. I am in control remember…just the way you wanted.”

She pressed her foot a little more firmly down, and Taylor felt himself stiffen a little in response. He let out the faintest of moans through his teeth, and Jillian grinned, “Good. I rather thought that would be your response. Now, we’ve covered the basics, I want to try something with you. You’ll play along, won’t you?”

Not trusting himself to speak, Taylor nodded, his wide eyes unable to look away from her mischievous autumn gaze.

Jillian nodded, her entire being radiating confidence and control, “Splendid. Now, both hands behind your back. Cross your wrists, and press yourself back into the padding. I want your arms trapped.”

Taylor did as she asked. Ordered. As he pressed himself back, his arms now behind him, Jillian’s foot pressed more firmly into his cock. Making it quite obvious that if he tried to move forward or free his hands he’d be in for a world of discomfort. He flushed. So easily stuck. So easily, and effectively, placed under her control. It was almost…almost as if…

“Imagine your wrists are bound…” Jillian’s words seemed to pluck Taylor’s thoughts right from his head, deepening his blush, “Imagine that I’ve trapped you. Imagine you are helpless to resist…”

Taylor swallowed, his flush growing as he squirmed in his seat, made all the more embarrassing by Jillian’s knowing smile.

“How does that make you feel? That notional feeling of helplessness?”

Taylor opened his mouth, unsure of what he was going to say. He should object. He should stop this right now. Fun was fun and all, but he really had no business…

“Does it feel good?” Jillian purred, her foot alternating pressure on his twitching cock. She reached out with a hand to run light gentle fingers across his jawline, sending fierce sparks of aching need and desire racing up Taylor’s face and body, in tandem with goosebumps from the contact. Taylor twitched and moaned, making Jillian’s eyes sparkle.

“Don’t you feel better? Safely in the charge of someone who knows what they are doing?”

Taylor nodded, and felt his hips tremble as her foot gently pressed further into his hardening cock, “Y’yes…I…mmmm….hhhhhmmm…”

Jillian giggled, her eyes calmly considering the sight of Taylor blushing and squirming before her

“Oh you are going to be such a splendid companion for me tonight, my darling boy.”

They stayed like that for an eternity it seemed to Taylor. He, stuck and trapped. His arms behind him and held in place by his own body, and Jillian’s artfully placed booted foot. She, supremely confident and in charge, still posing questions to him and guiding the conversation. Only now they had abandoned the ice breaking conversation of before. The talk of hobbies and interests, of life goals and travel experiences. Now Jillian wanted to know about his romantic experiences. His sexual experiences. His interests when it came to kink and fetish if any, and what sort of fantasies he dreamed of in the dark privacy of his mind.

Taylor answered as best he could, little noticing how freely he surrendered his innermost thoughts and dreams to this gorgeous, domineering older woman. She had him pinned in place, his mind and mouth an open book to her inquisitive investigations. It wasn’t until the boot suddenly disappeared from between his legs that Taylor’s mind snapped him out of the dreamy state that he’d been in as information was hoovered up by the vacuum-like questioning from Jillian. He blinked and looked up, finding her no longer in front of him, but standing next to him. The dishes had been cleared away. Everything was gone, the waitstaff having evidently come by in the middle of their conversation. The thought of them being present, seeing Taylor’s helplessness as he confessed to being excited by submission and helplessness brought a fresh blush to his face, and sent him to squirming again. Even as his eyes tracked up to find Jillian’s own.

“I have had a delightful evening.” She smiled down at him, “And still keeping those arms behind you. Such an obedient boy…” A finger curled beneath his chin, “Up now. I want you on your feet, but keep those wrists crossed behind your back.”

Taylor stood and obeyed her, keeping his eyes fixed firmly on the woman who was now definitively in charge of his evening. He didn’t dare look around to see what he assumed would be people staring at the odd posture he’d adopted. Better to concentrate on Jillian. Better to ignore the embarrassed feeling coursing through his brain, and instead revel in the sudden pleasant reversal of his evening.

Jillian allowed him to settle himself, standing quite close to him and running her hands over his shoulder and arms. Her smile was infectious, and Taylor found his heart rate slowing a little as he grinned in return, squirming slightly on his feet while keeping his wrists crossed and pressed together behind him. Jillian wordlessly tucked a finger beneath his chin again, and used it to gently turn him to follow her away and out of the hotel bar…and towards the bank of elevators. A brief wait of thirty seconds brought one down, and Jillian led him onto the elevator, one finger still crooked under Taylor’s chin. As the doors closed behind them, Jillian maneuvered Taylor to press him against the side of the elevator, pining him gently in place and locking eyes with him again.

“In a few seconds, those doors are going to open, and I am going to get off. I want you to follow me, but it is your choice. If you do follow me off…that is the last time you get to make a decision tonight. I will be in charge, and you will have to obey my orders. I’m not going to give away what is going to happen…but I can promise an experience that no girl you’ve ever tried to date would be able to give you…”

The elevator doors dinged, beginning to open. Jillian leaned forward and brushed her lips across Taylor’s in the briefest of kisses, leaving Taylor aching for another. She released his chin, letting her fingers trail down his chest, his stomach, to give the gentlest of touches to his now rock hard cock…before she turned and strolled away. Not even a backward glance. As though she knew he’d be following her, like there was no question at all that he was now hers for the evening.

And of course, there wasn’t. Not anymore. Not when Taylor’s arousal, horniness, and sheer interest had been so expertly nurtured, stoked, and fanned to a bright inferno all night long. He wanted to be with Jillian. Wanted her to guide him. Control him. Wanted to surrender to her care and experience, to propel him to the dimly glimpsed depths of kink and pleasant depravity.

Taylor was only a second behind her in exiting the elevator. Still with his wrists crossed behind him, still flushed and wide eyed. Jillian looked back from her position down the hall and smiled, “Good boy.” She flicked her hand to point at the ground, “You are going to crawl the rest of the way to my room. Hands and knees darling, now.”

Before his brain could properly understand what she was asking, and come up with a reason to resist, he found himself already on his hands and knees. Crawling to catch up with her. He neared her legs, and felt her hand brush across his head, “Good boy. Follow along now, there’s much fun to be had…”

A few short minutes later Taylor found himself standing in Jillian’s suite, trembling in place as the woman slowly wrapped his wrists in soft corded rope. Jillian had already stripped him until he was clad only in his underwear, the last scrap of dignity he had remaining to him. He shifted and let out soft little moans as he felt his hands restrained. The rope was soft yet firm, confining yet somehow freeing. Freeing Taylor from decisions, from needing to talk, from doing anything apart from standing still and experiencing the feelings racing through him.

Jillian finished cinching the rope, and polished off the wrist bindings with an expertly knotted knot, before she spun him around to face her. She began running her hands over Taylor’s naked chest, eyes alight with amused delight as she took in his expression. She began to softly hum as she touched him, exciting him and soothing him all at the same time. Reassuring him that he was safe, even as she stoked his desire and need ever higher. Higher and higher, until she leaned forward and murmured softly, “Mine.”

Taylor nodded, a moan passing between his clenched teeth as his fingers spasmed and clenched behind him, “Mmmm….yesssss…”

He felt her hand dip down and squeeze his erection through the thin fabric of his underwear, and he moaned, his hips almost automatically thrusting his throbbing member forward into her hand. He heard her chuckle, and felt her clench more firmly around him, drawing another moan from deep in his chest.

“Such a needy boy…well that’s precisely what I wanted.” Jillian stepped up more closely, her hand leaving his cock grip the back of Taylor’s head, holding him so that he was forced to look into her eyes, “Do you know what you need, Taylor?”

“I…I…”

“You need a collar.”

Taylor groaned, shuddering at the words. At the secret fantasies that blossomed in his brain as Jillian smiled and held up a leather collar, “All my boys wear my collar. It helps remind them that they belong to someone else. That they aren’t free anymore to do as they please, but instead have to remember that they exist to serve, submit, and pleasure their Mistress. Their Mistress Jillian.” She began to wrap the collar around his neck, kissing his cheek as she leaned in to whisper into his ear, “That’s what you are now Taylor. My boy. My plaything. My pet.” She finished buckling the collar on, one hand grabbing his hair to firmly yank his head back, drawing a moan that turned into a plaintive wail of need as she finished with a throaty growl, “My slave.”

Taylor’s mouth opened, “Oh, I maeeghhhh” and had his words silenced with a large ballgag that Jillian forced into his mouth. He let out a groan of denied desire, and Jillian chuckled as she pulled him around and yanked the strap tightly into place around his head.

“You wanted someone to take charge Taylor. I told you that I would. Don’t you like it when I call you a slave? When I call you my slave?”

He nodded, another moan escaping from between his gagged lips, even as she groped and touched him. Caressing his body as he squirmed against the ropes. As every breath he sucked in reminded him of the gag, and of the collar around his neck. Of his subservient position here in Jillian’s room.

He shuddered and moaned, squirming and writhing in place as he enjoyed the why her touches made him feel. The brilliant racing electrical sensation of warmth, excitement, and pleasure all coursing through him and making him feel more alive than he’d ever felt before.

“Good boy.” Jillian hooked a finger through his collar’s d-ring and pulled him after her, marching over to the large bed and positioning him at the end of it. He felt the touch of leather, and watched as his ankles were slowly cuffed and then roped securely into place to the bed frame. Keeping his legs spread, and making him lean into the bed. He suddenly felt Jillian stand and press against him, her hips grinding into his backside as her hands once more caressed and explored his back, his butt, his stomach, and his aching, twitching cock.

“I’ve a test and challenge for you, my darling pet.” Jillian murmured, one hand reaching beneath his underwear to begin slowly stroking his shaft, “I am going to fuck you tonight. I am going to give you pleasure you never dreamed possible…but in order for you to be allowed to orgasm, you need to pass my test.”

Taylor mumbled into his gag, and then squealed as she spanked him with the hand that wasn’t stroking him.

Jillian laughed, “Hush my bashful slut. You are going to be my little fuckslut, and take my strapon.” Taylor shuddered and moaned, drawing another satisfied laugh from Jillian, “Heh, I thought you might know what that is…seems my new playmate is quite the secret kinkster. But I bet you’ve never actually been fucked before have you?”

Taylor shook his head, moaning as his face was forced deeper into the bed as Jillian ground her hips against him, one hand now griping his bound wrists while the other massaged and groped his ass.

“Mmmmm, thought so. Another strapon virgin…all for me. Delightful.” Jillian giggled, “If you manage to take the fucking like a good boy, and avoid spurting, then you’ll be allowed to fuck me with your cock. I’ll ride you until you have the greatest orgasm of your life. But…if you can’t hold it in, if you insist on cuming like a bitch in heat, then I’m going to treat you like one. Instead of getting to fuck me, you’ll be locked in chastity. Instead of getting pleasured by me, you’ll be using your mouth to give me orgasm after orgasm. I’ll keep you tied up, locked and chaste, collared and helpless, until I am satisfied.”

Taylor moaned, his own hips now grinding against the bed even as Jillian pressed more forcibly against him. He felt her lie across him, her lips brushing against his ear as her words came in a sultry whisper, “And guess what slut? Either way, you’re going to have the best night of your life yet, here with me.”

Taylor groaned as she left him to squirm against the bed. He looked up towards the head of the bed, just in time to see the crumpled green floral dress arc over him to land in a heap. “Mmmrrffgh??”

“Oh yes slut, your Mistress is naked…apart from my boots and this strapon cock. I wonder if you’ll get to see this gorgeous body…or if you lack the self-control to earn that…”

Taylor groaned, squirming and struggling in place, but not daring to do more than that. This was so far beyond what he had thought he was in for, he was still caught between the heights of arousal and the uncomfortable sense of being completely out of control. He’d never felt so helpless, so unable to control the flow of events…and he couldn’t help but love it. Love that he didn’t need to make decisions. Love that someone else was in control. Of the night, and of him.

Further thought was abruptly ended as he felt the cool touch of slick gloved finger on his butt…and a swift snipping sound that heralded the destruction of his underwear. A small warbling moan was answered by three sharp spanks on his now naked rump, and then the return of those lubed up gloved fingers to probing his asshole. He arched his back and groaned loudly into the gag as he felt the first finger enter him. Enter, and then begin plunging in and out. In and out, over and over. All sorts of oddly pleasurable sensations began percolating into Taylor’s mind, making him grind harder into the bed as his stiff cock ached for release. He bit down tightly on the gag as he felt the finger swirl around again and again…before abruptly slithering free.

Taylor’s moan in response was swiftly met, silenced, and then redoubled by the feeling of rubber pressing against him. Of Jillian’s naked thighs touching his own, of her hand grasping his hip as he felt the rubber press into him. Penetrate him. Taylor threw his head back and moaned, his fingers clenched tightly into fists as he felt that first inch of hard rubber slide into his ass. It was slick with lube and made steady progress, as Jillian edged herself closer and closer to being able to touch her hips to his ass. Murmuring the whole while, soothingly little words and phrases.

“Such a good boy for me,” Jillian crooned, rocking her hips a little and pushing and then withdrawing slightly. Working it inward with each thrust and then backing out a little on the return, “My good, obedient little boy slut. You love getting your ass penetrated by your Mistress don’t you?”

Taylor moaned and nodded, the movement jerky as his body was unable to stop squirming and shivering as the rubber phallus steadily journeyed deeper into him.

“Mmmmmm…yesssssss….sssssuch a good boy. That’s it. That’s it slut, take it deeper. Let it slide into you like the good little whore you are for me. Just for me. Just for Jillian. You love being bound and dominated don’t you slut?”

“Mmmmhhhhhmmmmmmmm…” Taylor moaned and arched his back, bucking his hips as he felt the rubber cock press deeper into him.

“Mmmm, yesssss I knew it. I knew you were a needy little submissive…someone who just needed a firm hand…I’m here now boy…that’s it keep taking it…I’m here now, and you’re safe. Safe in my collar. Safe under my control. Take my cock. Take it aaaaaalll the waaaaaayyy…yes!”

With that final yes, and a final firm thrust of her hips, Jillian pressed the entire length of her rubber cock inside Taylor. Presing her hips firmly and forcibly up against him. Grinding her own hips into his as she made him feel every bit of that length, and placing both of her hands on either side of his hips.

“Ready slut?”

Taylor burbled into his gag, shuddering and shaking.

“Good.” And Jillian began to thrust. A steady, slow back and forth, drawing herself out a couple of inches before going in again. Acclimatizing Taylor to the sensation of being filled, over and over again. Making him grow used to feeling the hard rubber press up so achingly close to that spot inside of him. Making him groan, and squirm, and squeal, and moan.

“Mmmmmm….such a good slut. Taking that rubber cock like a champ, my darling boytoy. Mmmmm…you’re a natural little bitch…gaaaahhh…yesssssss…”

Jillian began to pick up the pace, plunging her strapon in and out of the helpless boy she had seduced and bewitched back into her rooms. She smiled as she griped his hips, thrusting into that naked, needy hole. Reveling in his moans and squeals as she slowly and steadily made him her bitch. She slowly lost herself in the motions, the steady well-known and well-worn patterns she was using now had been crafted and perfected on so many playmates before Taylor. She could afford the luxury of mentally wandering off. Her mouth and body would remain on autopilot. Teasing him verbally with the dirty talk that seemed to drive him wild, all while her thrusting hips sent him careening ever closer to the point of no return.

There was no way at all that he was going to hold out against her. Not even the faintest hope that he was going to get to fuck her. She was far too skilled at wielding her strapon for that sort of thing to occur unless she wanted it to…and she wanted this boy in chastity. She wanted to see the look on his face when she caged his cock, and when she clicked the lock shut. She wanted him to know, and to show her that he knew, that she owned his cock and his pleasure. Jillian was going to wear his key.

She wanted him bound, and collared, and chaste, and relegated to being her helpless pleasure pet while she reclined on the bed and relaxed after a long work week. While he licked her to orgasm, she'd play with his key, and tease his caged cock. While he gave her orgasms, she would make idle chatter about how much she loved caged cocks. How much she adored boys who surrendered the timing of their orgasms and pleasure to her. She wanted to bind him up even more, and cuddle with her bondage toy as he did his best to contend with the aching need that would only worsen once he was denied, chaste, and strictly bound for sleep.

She was going to keep him like that, once he’d fully satiated her for the evening. She’d be able to drift off to sleep, secure in her dominion over her pet, and pleasantly exhausted from the work that his tongue was going to put in. After all, she needed her beauty sleep, and to replenish her energy for what was going to come next.

Taylor wasn’t going to be released tonight. He wasn’t going to be released tomorrow either. He would be woken up, or perhaps swim back to awareness, whenever she decided to rise tomorrow. He’d be set to pleasuring her again, and again, and again throughout the day. All while staying locked in chastity, and his collar. She’d take him again with her strapon, perhaps more than once. She’d make him suck it, humiliating him in her gentle way by making him show her how he wanted his own cock sucked. She’d tell him that the only way he might earn a blowjob from her, was to show her he appreciated what a perfect blowjob entailed, and demonstrating that he could give one too. She’d make him do little tasks and chores around the suite, introducing him to the latex maid uniform that she’d brought along for precisely this sort of opportunity. Then she’d take him to bed again, to fuck his tight little ass, to tease his locked cock, and to be pleasured by his desperate tongue. All before locking him away in bondage again, and falling asleep while snuggling into his struggling, squirming body.

And she would do it all again the next day. And the next. Guiding him onwards into ever deeper submission. Stringing along his desperate need to orgasm, and gradually beginning to replace it with an equally desperate need to surrender and serve. To place pleasuring her on an equal footing with his own pleasure. Convincing his body and mind that his proper place was as a desperately denied, and eternally horny slave slut. That to be locked in chastity for Jillian was to achieve a constant level of pleasure and satisfaction that a normal orgasm from normal sex would seem like spoiling the wonderful dynamic she offered.

That he would never, ever, be allowed to touch his uncaged cock again. That was Jillian's right, and hers alone. She owned his cock, and Taylor would have to learn that whatever pleasure he was allowed to feel, would now come solely from Jillian.

Such a mentality switch would take far longer than the several days she had at her disposal, but that was fine. Jillian only needed to plant the seeds of need within her boy…and he would follow her anywhere.

For when her stay was finally over, and it was time for her to return home, she would pack Taylor away into the large rolling suitcase that she had brought with her. By that point he’d be sufficiently down the path to becoming her pleasure addled, desperately horny little slave slut that she was confident he’d be pliable enough. Promising that he’d get to cum if he came home with her would be the last little temptation to get him to tamely allow her to strictly bind him and place him in that suitcase. Her own little travel gimp maid. Forever teased and denied. Forever bound. Forever helpless. Forever hers.

She’d meant what she’d said, back during their meal. He was hers now. There was no going back.

Jillian grinned, running one hand over the shuddering and squirming form of her new slave boy.

Beneath her Taylor bucked and squealed into his gag, shuddering as he felt himself reach and then surpass that terrible cliff edge moment. The moment when he knew he couldn’t hold on as much as he might try. He threw his head back with a muffled cry, feeling Jillian’s hand flash out and seize hold of his hair, yanking his head back still further as she thrust in and out of him faster and harder.

Forcing him towards his first, but far from his last, strapon induced prostate orgasm.

“Yessssss! That’s it slut! That’s it! Take my cock! Take my strapon and cum for me! Cum for your Mistress! Cum for your owner! Prove that you’re my submissive little bitch! You want this you waaaant thisssss, yes! Yessssss! Mmmmmmm….goooood boy….gooood boy…”

Jillian laughed as she felt Taylor shudder and cry out, feeling his body seize up and then jerk and shudder as he spurted onto the towel that she had discretely shoved beneath him while she was lubbing him up.

“Mmmmmm….what a good boy. What a good boy! Awwwww…” she chuckled as Taylor let out a muffled disappointed moan, “…was someone hoping to fuck me? Were you hoping to feel the wonderful warmth of my pussy around that cock? Mmmmmmmm...such a silly boy…you can’t even control yourself when you’re getting fucked. Someone like that needs some time in chastity.” Forever in chastity. Forever hers. Jillian let out a throaty growl, her eyes flashing with hunger and pleased, domineering control as her gaze roamed over the adorable body of the boy she owned now, “Let me just go get that cage slut,” she was still thrusting into him. Still plunging that rubber cock into his rear. He shook his head and moaned, making her laugh and thrust again, “Awww, does my slut want me to keep going? You don’t want to be locked up yet?”

Taylor moaned and nodded, struggling and straining against his bonds even as his mind grappled with the pleasure that was still coursing through his body after its first titanic prostate orgasm. Jillian let out another laugh, pleased and amused at how the novelty of being strapon fucked had already so altered what Taylor had wanted out of this evening. Hardly a blip of protest that sex with her was off limits. For her boy, there was only his hole and his tongue. The means of receiving pleasure, and the means of giving it. His cock, as he would come to learn, was going to treated as an implement to control him. Nothing more than the means of keeping her new slut horny, desperate, and thoroughly submissive.

“MMmmmm…my little butt slut. What a goooood boy…” Jillian’s thrusts continued as she crooned to him, “Well…I suppose I can fuck this tight little hole a while longer…but then you are going into your cock cage, and you are going to learn how to pleasure your Mistress, slut. And if you ever want to feel that glorious feeling of orgasming while I take you with my strapon…you’re going to have to be my good obedient little pleasure pet aren’t you?”

Taylor nodded, his eyes and mind glazed over. Giving himself over to sensation, as Jillian continued to fuck him. Continued to plunge her cock into his body, effectively thrusting submission into his body with each powerful movement. Removing second thoughts. Removing embarrassment. Removing shyness. Replacing it only with the burning need to feel those feelings again. To revel in his submission to this gorgeous, older woman. This heaven sent opportunity to feel connected with someone at last. To feel that someone was in charge of a relationship…and all he needed to do was obey and submit. That’s all that Jillian required of him tonight…

Jillian smiled as she heard the tell tale small moans and grunts of Taylor slipping off into subspace. Off into that gloriously heightened state of physical and mental awareness and desire that would make him hers all the more. Removing the last vestiges of his vanilla worries and cares. Leaving him only with his burning need for her, and her control. He didn’t know it yet, but his last moments as a free man had consisted of crawling into her hotel suite and allowing her to shut the door. Going forward he was going to be an owned man, a submissive slut for Jillian and addicted to her control and dominance. She was looking forward to what she might be able to sculpt this deliciously submissive shy introvert into…

Perhaps in a month or two, she’d take him back out into the public eye. Back out into the world, but at the end of her leash. Mincing along next to her in strict bondage, all encompassing latex, and still without having achieved his ardent desire to fuck his MILF Mistress. He would be her deliciously chaste, strictly bound, and delectably collared boy.

Forever.