AAkasha
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This is part one. If people want part two, I will post it.
Delilah selected the posh downtown Hollywood hotel for a reason. It had a great location, a great suite with a view, and the lobby held a certain flair that appealed to her. She envisioned bringing many men there at one time in her life – but this time, it was really much more simple. There was one thing she wanted to do, and her slaveboy (well, man, really) was going to assist her with it.
This man – Brad – was a simple man, really. He was pleasant, classy, charming. He had traditional corporate good looks, a fairly decent body, but a pathetically small cock. Delilah liked to tease him relentlessly about this, and it always made her wet when he squirmed, visibly uncomfortable, as she stared and poked and laughed at his small member.
But Brad adored her and would do anything for her. That’s why they were such a good couple. Delilah was delicious, gorgeous and cruel – and Brad ate up every last bit of it, because he was a masochist and a pure whore at heart, and nothing thrilled him more than to see that delight in her eyes when she made him feel pathetic.
It was the second anniversary of their first date when she made Brad take her to the beautiful hotel. She wore an elegant sundress and sandals over her perfectly painted pretty toes, and he followed behind her a few paces with the luggage as she flirted with the bellmen and seemed to immediately have the young men drooling and watching her every move.
Brad could only watch and long for her attention. It was at times like this that he was reminded that she was the goddess and he was merely a tool for her – his devotion could only get him so far. At times like this it was like he did not exist. He was entirely forgettable. He just stood there next to the pile of luggage as two college-aged bellmen hustled around her to answer her whispers, not even acknowledging the existence of Brad.
Of course, when they realized he was with Delilah and the bags were indeed, hers, the boys climbed over each other to get to them and load them onto the cart for the ride up to her room.
“Nevermind that,” Delilah smiled behind her big sunglasses. “He’ll get my bags.”
This froze the tanned, gawking bellmen in their tracks for a moment, until Delilah added, “Oh, no. I still want you to come up. But he can carry the bags. You can open the door, dear.”
The bellmen looked at each other and pointed and chuckled, and one said, “Him or me?”
“Or both of us?”
“Him,” Delilah pointed. “You.” Her fingers touched the plastic name tag that read simple, “Jackson.”
“What a handsome name,” she smiled. Jackson blushed.
Brad pushed the cart that carried seven bags. Seven bags for an overnight stay. You could just never pack enough, Delilah would always tell him. Because she never knew what she would need.
Seven bags, and only one of them included any clothing.
Six bags, all leather, all toys, all devices. Brad held the cart as the elevator door closed, and he looked over to see Delilah smiling at Jackson, smiling at him as if he was prey. The sound in the elevator was simply the shuffling of his feet a little, the clearing of his throat, and Brad’s nervous, uncomfortable heartbeat.
**
Delilah did end up making Jackson unload the bags off the cart, telling the boy that he would need to earn his few dollars and that she wanted to watch him bend over. He blushed at the remark and kept looking awkwardly at Brad, probably wondering if the man was a driver, a lover, or a personal assistant. Brad was older than Delilah, who was older than she looked, but Brad had a forgettable quality because he’d become so good at being invisible when Delilah was prowling.
He was content to watch her, actually, because it thrilled him to see her in action, to see her start to get excited over the prospect of new prey. In no time she had the unassuming bellman in a bit of a trance, hoping to get laid, probably, but at the very least excited by the attention he was receiving from a beautiful lady.
Jackson took the handful of dollars eagerly, but really lingered in the room just to take in her figure and perhaps extend the fantasy a little. Delilah smiled at him and then told him she’d call down later to have him come up and move the furniture around. The comment made him laugh, but as he exited the room, his smile changed to a look of wonder as he realized she wasn’t joking.
After the door closed, Delilah snapped her fingers and Brad moved beside her, kneeling, absolutely on command, automatically. His eyes were shut at once.
She pulled up her dress, took him by the back of the head, and shoved his face into her pussy, pressing it tightly against the front of her panties. They were moist beyond words. He inhaled her scent.
“Jackson was nice to look at. Don’t you think?”
She was making a point to him. Brad got the message loud and clear. Her grip was firm, though, and it was obvious she was going to keep his face mashed against her panties, up against the lace, until little indentations appeared on his cheeks as if he’d slept wrong on the covers all night.
“I bet Jackson has a big dick” Delilah mused.
Brad could practically feel, smell, hear her getting wetter. Her fingers tightened in his hair. They tightened until he had to bite his lip to hold back a whimper.
Delilah appeared to be contemplating something, fantasizing out loud. “I bet young Jackson could fuck for hours, simply hours, and his big dick would feel so good in my pussy. Don’t you agree, tiny dick?”
The words hit him, went through him, made him shake a little. Brad was shaking and he didn’t know why. He didn’t want to get caught up in the wonder of why such humiliating statements excited him so much, because he wanted to enjoy the moment. He resigned himself to analyze later, as he always did, but never got around to.
Delilah’s grip tightened even more, and she parted her legs a little, inhaled, and said simply, “Tongue.”
This was Brad’s order to open his mouth and use his tongue, somehow, any way, to indulge her. It didn’t matter that her dress was up over his head, that her panties were still on. These were his problems. She was busy, he knew that, busy with her own thoughts – thoughts of Jackson’s cock. So he tried as best he could to get his tongue working under the elastic of the panties, or prodding over the top, doing anything to get close to her skin, to her clit, without disrupting her thoughts too much by banging her around with his head.
This was a delicate dance he’d learned many times. When she wanted tongue, he had to figure it out, and not bother her about it. He had to just obey, to find a way, and to hope he could do so in a manner that pleased her.
Her grip loosened a little on his head, a subtle indication that he was at least going in the right direction. “Yes,” she pondered out loud, “Jackson would be a nice fuck. But I don’t really have time for that. I have other plans for tonight. Plans….for you, Brad. You and your little cock…”
Brad’s eyes were closed, tongue was busy. He could hear the words, barely, as he pursued his task, trying so hard to please her, to make her more wet, to color the fantasy she was having by adding pleasure. It didn’t matter that she was thinking about Jackson’s cock, not his. All that mattered was that she was happy, and all that he wanted to hear were her moans of pleasure. At any cost.
**
Brad was hogtied on the floor as Delilah stood in nothing but stilettos, bra and panties.
She was walking across the floor with a big wad of money in her hand, many bills she’d pulled from one of the large suitcases as she unloaded toys, lingerie, outfits and devices, some of which he had never seen before.
Delilah started stacking the dollars across the nightstand, stopping to dance suggestively now and then, as the CD player in the room was cranked up with some alternative music that he found loud and somewhat obnoxious – but incredibly erotic when her hips were moving to it.
Delilah was in her own world, not even watching him struggle anymore (oh, how she loved to watch him struggle, sometimes just sitting and playing with her pussy for hours as he writhed, wriggled and groaned uncomfortably). She was stacking up the bills in a manner that looked like something out of a gangster movie when the bad guys were counting up their dough after robbing a bank.
The bills were crisp and stacked up nicely. Brad could not tell if they were tens, twenties or even hundreds.
“This is Brad’s money,” Delilah grinned, looking back over at him and giving him a nod which indicated that she wanted to see some struggling. Brad struggled.
“This is all Brad’s cash, and it’s here for a reason. Do you want to know what it’s for, Bradley bitch?”
Brad was afraid to ask, but he wasn’t gagged, so he went ahead and spoke. “What’s it for, Delilah?”
She smiled. Delilah walked over and lifted her leg slowly and deliberately, bringing it down to press her heel on Brad’s naked, tiny cock. “Oh, careful, I might smash that tiny little dick,” she teased. “Can my heel cover the entire thing? I bet it can. Does that hurt?”
Brad winced. He was used to this game, sadly. So many times Delilah had smashed, stepped on, poked and nearly punctured his penis with her heel. She did that when she wanted him to pay close attention to what she was saying, but it always did more to distract him. And even though he was struggling, hogtied, unable to protect himself as she pressed her spiked heel into his cock and leveraged it against his thigh, he found himself getting excited.
It wasn’t the pain or humiliation that excited him; it was the look on her face, the pleasure and amusement. She was glowing, electrified, excited, enraptured and he could tell her imagination was running wild with scenarios, ideas and plans that required a hotel room and seven pieces of luggage. This was unpredictable, cruel, insatiable Delilah.
He whimpered.
“The money is for tonight,” she continued, finally, now looking down on him to poke, prod, and pump her heel on and off his member, almost amused, experimenting. “I took thousands of dollars out of your account tonight because YOU – “she stopped to press deliberately hard right into the base of his cock, until he gasped. “YOU – are going to go out tonight, to Hollywood boulevard, and get me a hooker!”
Brad didn’t really hear that part, as the pain was making him shut his eyes tight, grimace, and see stars. But he felt her breath on his cheek when she crouched down, removing her heel finally, taking his chin in her hand and saying more clearly, “Brad is going to go out tonight and find me a MALE prostitute! And you are going to bring him back to the room and be a little bitch for me while I enjoy a real cock.”
Brad started to speak, and realized, half way through, that his words were a terrible mistake. “But…why don’t…why don’t you just call Jackson… he’s will –“Brad stopped and gasped in pain as he felt the familiar, ruthless grip of her fist around his balls. She gripped, squeezed, twisted and pulled.
“I don’t WANT Jackson. I want a WHORE. I want a streetwalker, with a BIG huge dick, and one that will do ANYTHING for money. Even more of a whore than you are!”
Brad got the message loud and clear, but he was still seeing stars when she rolled him over, spread his ass cheeks and started feverishly pumping her fingers in and out of his asshole – lubing it before shoving a large plug inside, then slapping his ass cheeks until they were red. Just playfully. Brad was breathing hard, his small cock fully erect to four inches, his ass pounding and his cheeks hot.
Delilah stood up and left him there on the floor as she mixed a cocktail, then stacked up the dollars into one large pile and went to the closet. “First, you will get me dressed. I want to be smoking hot for the male hooker, and while you get me ready, I’ll tell you what I want you to bring back. I don’t want to be disappointed, you see. I want your money to go to good use. And since you’ll be sucking his dick for me, I want to make sure he’s got a nice big cock. Even though everyone has a bigger cock than you!” Delilah burst out laughing.
“Untie yourself and then put on your pink teddy,” Delilah ordered. She bent over to release the one metal tie clasp that would allow him enough freedom to wriggle and writhe out of the hogtie. “Once you are dressed in your best cunt outfit, we’ll get my look together. We’re going to have such a nice evening!”
**
An hour later, Brad was playing wardrobe assistant while wearing nothing but a tight, uncomfortable, humiliating pink corset, thigh high stockings and lace panties. Delilah lounged in main part of the suite and smoked a cigarette casually, making a few phone calls to girlfriends and occasionally barking a seductive order.
Brad hustled, keenly aware of his uncomfortable erection in the panties and the too-tight feeling of the plug as he moved around the room. He heard her in the next room as he rummaged through the large closet, trying to find the boots she had described to him. He could hear her calling room service and ordering a bottle of champagne.
Next, he heard her instruct the room service staff to have Jackson bring it up, then he heard her provide explicit instructions about it, making sure they were aware of her account with the hotel, her connections with the hotel manager and her status. It did not take long for him to realize how much the wait staff was going to be hustling, which meant in no time Jackson would be knocking eagerly at the door with the room service cart.
Immediately Brad was distracted, horrified, mortified, at what he knew Delilah was up to. He sheepishly brought the boots into the next room and she shook her head. “Not those ones. You stupid bitch. Get me the leather boots. Then go answer the door. There will be a knock momentarily.”
Brad wanted to sink into a hole and disappear. “Can I put on some clothes?”
“You’re wearing clothes.”
“Delilah…please…”
Delilah laughed and put out her cigarette. “Fine then. I will answer the door. You go run off and hide in the closet then, and don’t come out until I tell you that you can. Remember, this was your choice, Brad!”
He watched as she made her way to the door. Delilah was now dressed in only smoking hot black lingerie, high heels, her make up and hair done dramatically, her body smashing. When she opened the door in that to the waiting Jackson, he’d be ready to die on the spot, sure he’d died and gone to heaven, and Brad would be curled up in a ball hiding in the closet until she was done – which could be hours.
It was that, or answer the door in pink lingerie with a tiny erect penis popping out of a too-tiny thong, humiliated, as Delilah laughed and pushed him aside and probably made some cruel comment.
Ironically, it was impossible for Brad to determine which scenario turned him on more.
Dejected, he retreated into the closet and closed the door, mostly because he did not want to risk offending Jackson with the sight of his large, bulging body in the pink lingerie. Instead, he found himself surrounded and assaulted with the scents of Delilah; her leather wardrobe, the various pairs of panties, many still wet, tossed inside the confines of the closet. Dirty lingerie, black shiny rubber, and an assortment of toys joined him in the cramped space. He heard the popping of the champagne bottle, the deep laughter of a bellman obviously pinching himself because he was sure he must be dreaming.
Then he heard the familiar moans of sweet Delilah being fucked; she choose the place on the floor right next to the closet, her legs probably up over her head, and by the sounds of it, Jackson did have a huge, wonderful cock.
**
Brad counted four orgasms and three positions, and it was more than 90 minutes before Jackson was allowed to leave the room. Not until she tipped him though – with Brad’s money.
“Holy shit,” he heard the young bellman exclaim. “I can’t take that.”
“Take it,” Delilah ordered. “It’s not my money, it’s my boyfriend’s.”
“I can’t take two thousand dollars! That’s not a tip, that’s -- “
“Take it.” She ordered. “I insist. I get wet when I use my man’s money that way.”
Brad shut his eyes tight. He realized he had jumped the gun – they weren’t over at all. They were just getting started. He heard the familiar sounds again, kissing, moaning, and then fucking. This time, Jackson lasted 30 more minutes.
**
Brad fell asleep in the closet but awoke with a start when Delilah opened the door. He came pouring out of the closet as he was leaning against the door, waking up when his cheek hit the ground.
She laughed out loud. Brad looked up to see her standing there, disheveled a bit but still beautiful, holding a glass of champagne. She opened her legs a little. “Cum’s dripping down my thigh. Lick it up,” she said. It was so matter-of-fact for Delilah.
Brad struggled, cramped from being in the small space, but managed to kneel upright and move his face to her leg and open his mouth, letting his tongue lap up the creamy clear-white fluid that was indeed trailing down her thigh.
“I saved some champagne for you,” she smiled, reaching to the countertop and taking the glass that was placed there.
Brad looked up, licking his lips, tasking the young man’s cum. He did expect her to have a glass of champagne, but realized all too quickly that of course that’d be too easy. Not Delilah.
No, she had a glass in her hand for him, and a smile that made her look like she’d just won the lottery – pleasantly fucked, glowing, gloating. And in her hand was a champagne flute for him.
Half full of cum.
**
Part of Brad thought maybe Delilah had “spent” enough money and got what she wanted out of Jackson and would dismiss the dreaded hooker idea, but he was mistaken. In no time, after watching him lick clean the glass of Jackson’s cum, she was ordering him to help her freshen up and providing him a list of criteria for his male gigolo-expedition.
She was explicit about what she wanted. The male prostitute had to be young, built, have a huge cock (black would be ideal, if his dick was humongous, although “Any guy looks huge next to your little pecker”), and be clean in appearance, not a junkie, no drugs, and not look or act gay. Delilah told Brad that if he came back empty handed or came back with a guy who looked like crap, was a street whore or drug addict, she’d spend the evening kneeing Brad in the nuts until he cried like a little girl. He knew she meant business.
After much begging, Delilah did allow Brad to put some clothes on over his lingerie. She was going to tell him no, after all, the transaction was going to be made from the safe confines of his car and the gigolo would not see his cute pink teddy until he got in the car anyway. And who cares – Brad was a paying customer. But he pleaded with her, and she let him put on shorts and a t-shirt that barely covered him up.
Delilah gave him a time limit of one hour and as he left she was curling her long, beautiful brown hair, sitting at the vanity in nothing but a short cami and black thong panty. Her hot outfit was on the bed, ready for her, and her shoes were lined up perfectly so she could make a selection. The stacks of twenty dollar bills were still lining the dresser table.
Off Brad went, horny and leaking, to scour the streets of West Hollywood in search of a young, hot, hung stud with a big cock so his lovely Delilah could pay him to get his dick sucked.
He had never been more turned on and ashamed.
**
Brad “shopped” intensely with Delilah’s instructions in mind, wanting so desperately to bring home a prize she’d be pleased with. He found himself looking at the prospects in a manner that seemed to excite and arouse him as he was thinking so much of her pleasure and satisfaction. It became surreal how much looking at these men made him hard and horny and how he found himself imagining the feel of their dicks in his mouth. But mostly he was imagining her wonderful, pleasing moans of ecstasy as she watched and participated. He felt the panties getting incredibly tight, making it uncomfortable to drive.
Nervously watching for police, Brad leaned out his window and awkwardly conducted quick interviews with the laughing, smoking male hookers, some of whom took a liking to Brad at once, probably because of his Mercedes and look of wealth. But the ones that approached him seemed too gay, and he knew Delilah didn’t want that. So he pressed on, getting more nervous and worried as time ticked by.
He imagined waiting Delilah, back in her room, legs open in the large chair at the vanity, playing with herself in the mirror. Delilah liked to masturbate in the mirror, sometimes she would make Brad watch her while she watched herself, her toes curling into the mirror as her legs were up on her own vanity at home, her pink vibe sliding in and out, deep and inside, her hips thrusting as she wailed in pleasure.
Brad stopped himself as he tensed and twitched uncomfortably, awkwardly in his car seat. He stopped at a corner and looked out, spying a younger looking, tall, dark haired man standing nearby. The man caught his glance and walked over, leaning down, smiling. “What’s your name?” he asked in a deep voice. He looked European.
“Brad,” was his response. He stared at the handsome gentleman – he knew his dark, European looks would please Delilah. “How old are you?”
“Old enough,” the man smiled. “My name is Jeremy. Can I get in?”
Brad nodded, and Jeremy came around and got into the car. He was in jeans, a leather jacket, nice shoes. He didn’t look like he was homeless. He was wearing a nice watch and some jewelry.
“You a cop?” Jeremy asked, still pleasant, smiling, very casual.
“No,” Brad responded, watching the young man put on his seatbelt.
“Then let’s go,” he said, leaning back into the seat, admiring the inside of the automobile.
Brad was excited. He could smell a little bit of cologne. Jeremy looked clean, presentable, and he had a big, thick bulge in his jeans. Brad thought about asking how big he was, just to be sure he’d meet Delilah’s satisfaction, but even the outline in his jeans told a story. Besides, he only had fifteen minutes to get back to the hotel, and he could not keep his Mistress waiting too long.
**
Brad could not find a way to explain anything to Jeremy, who occupied his time adjusting the car radio, singing a little, and then sending some text messages on his phone. Jeremy said something about five hundred dollars and condoms and Brad just nodded and said that was fine, focusing on his car speed and the urgent matter at hand.
Brad’s heart was pounding, so nervous, thinking of what Delilah would think of the prize he was bringing back to the hotel. His mind wandered to what it was going to be like when he sucked the strange man’s cock, and if Delilah would let him use a condom since the man was a whore. He wondered if she was going to fuck the hooker in front of him and make him watch, and how much she would humiliate him about his small penis and inadequate abilities in bed.
Nothing really mattered, though, except the smile she would have and her pleasure, her amusement in the evening. Brad knew that Delilah clearly was electrified by this fantasy and reality and was probably well on her way to her third self-inflicted orgasm by the time her brought Jeremy through the lobby and to the elevator.
“You in town on business?” Jeremy asked as Brad pushed the button for the 17th floor.
“Kind of,” Brad responded. When the doors closed, Jeremy reached over and put his hand on Brad’s crotch, making him jump and push his hand away. It was unexpected and uncomfortable.
“Easy, there,” Jeremy laughed. “Sorry. First time? You straight? Curious?”
The door dinged. Brad cleared his throat. He wondered at that moment if he really knew what he was getting himself into.
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