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Cruel Delilah: Real Adventures of a Cuckoldress

By Akasha

 

  

 

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. 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.

 

**

 

Brad was obviously ten times more nervous than Jeremy (who was not nervous at all, not that Brad could tell at least), but then again, Brad had a lot more on the line than the hooker did. If he disappointed Delilah, it would be a long night. It was going to be a long night anyway, with cruel Delilah, but disappointed Delilah was an entirely different dilemma.

 

By the look on her face, Delilah was not disappointed. Brad took her all in as if seeing her for the very first time – she was simply captivating, so beautiful, so sexy, wearing a tight black dress, showing off fine toned legs with sexy five inch heels. Of course, Jeremy was gay, or at least presented himself as gay, so he probably was not as impacted – more so, he was kind of puzzled.

 

“Well, aren’t you a handsome thing,” Delilah smiled and walked over, holding out her hand to make an introduction. “Delilah,” she beamed, looking the man up and down slowly, tilting her head slightly to take a longer gaze at the visible bulge in his jeans.

 

“Jeremy,” he smiled back, then looked at Brad, curious, put his hands in his pockets, and said “So what’s going on?”

 

“The shower,” Delilah instructed, and put her hands on Jeremy’s shoulders, spinning him toward the bathroom and giving him a shove. “You’re getting cleaned up, then Brad is going to suck your dick, then you are going to fuck me.”

 

“Cool,” was Jeremy’s simple response, as Brad felt twitching in his panties, a flushing warmth in his cheeks, a familiar tension building in his frame. The plug was still nestled tightly way up into his ass cavity, and the shuddering in his bones made the plug even more uncomfortable and ever evident. He stood there, unsure of what to even do with himself, as he heard the water come on in the bathroom shower and some laughter erupting.

 

As if on cue, Delilah emerged, taking off her earrings and slipping off her shoes. It was clear she was going into the shower also. In a moment, her dress was off and she flung it at Brad and the fabric slapped over his face. When he pulled it down, her panties smacked him in the face. “Hang up my clothes, bitch,” she ordered. “Then get undressed, down to your sissy lingerie, kneel down, and wait by the bed sucking on your large dildo like it’s a pacifier. See you in twenty minutes.”

 

And that was that. Brad stood there, holding her dress, her stockings, bending over to pick up the rest of her clothes and lingerie as he watched her naked, perfect ass dart into the bathroom. She left the door wide open so he could hear everything, of course, from the moans to the laughter, the splashing of the water, and her commentary on the size and thickness of Jeremy’s perfect cock.

 

Brad, now in nothing but a too-tight pink ensemble of sissy lingerie, found himself kneeling bedside as instructed, sucking a large, thick flesh colored dildo obediently. Up and down he went, sucking, slurping, eyes closed, concentrating on it, realizing that soon he’d be deep throating the entire length of Jeremy’s perfect dick as Delilah watched. Maybe she would circle around him and give instructions, reaching over to poke at Brad’s miniature erect penis. Maybe she’d stand behind him and spank his ass with a paddle to force him to go deeper. Or, if she was in a certain mood, she’d just sit there a few feet away and masturbate with her thin vibe, cumming again and again as the well hung man came all over Brad’s face or in his mouth.

 

As usual, Brad had no idea what his fate would be. He just remained kneeling there, reaching down occasionally to shift his small package in the too-tight panties, trying to assemble some level of comfort despite the growing fear and dread mixed with anxious excitement.

 

If nothing else, his jaw was clearly now stretched out and he was ready to accommodate Jeremy’s dick after twenty five minutes of practicing. So when the man emerged from the shower, a towel wrapped around his waist and Delilah trailing behind him naked, he thought he’d be ready.

 

Truth be told, Brad was never ready. It was always like the first time again.

 

**

 

Delilah crouched down and got close to Brad’s face, and her smile illuminated his world. He could smell wet pussy, it was as if her arousal seemed to permeate her entire being when she was that hot, that full of lust. Indeed, she was full of lust – lust for Jeremy, the gorgeous, perfectly built hooker who was there for $500 an hour. $500 an hour of Brad’s money.

 

Delilah smiled her big, pleased grin and put a finger under Brad’s chin. “Is tiny dick ready to suck a real cock for me?”

 

Brad was staring at Delilah, shaking a little, barely aware of the presence of another man in the room, who was off behind him pouring some champagne or inventorying the gear that was spread out everywhere. Maybe he was admiring the tall stack of twenty dollar bills that sat on the dresser.

 

Delilah went into a nice, long, humiliating diatribe about how large Jeremy’s cock was, and how excited she got in the shower when she was able to hold it, feel it against her skin, and tease her pussy with it. Because, after all, she was rarely around such a big cock!

 

She emphasized this by reaching down and pulling Brad’s pink panties down a little, then poking his erect member with her fingernail. “Is it hard? Is that it?”

 

Jeremy was chuckling somewhere in the background, seemingly unaffected by the fact that the man who picked him up an hour earlier was kneeling with a dildo in his mouth wearing nothing but a woman’s set of pink lingerie as Delilah poked his penis with her fingernail and called him “tiny dick.”

 

Brad reminded himself that as a male hooker, Jeremy had surely seen worse. Somehow that did not make him feel less degraded and humiliated though, as Delilah turned around and addressed the gigolo, asking if he’d like his dick sucked or wanted to wait, asking if he wanted to piss on the sissy bitch in the bathtub because she looked good soaking in golden pee, or if he just wanted to fuck Delilah doggy style right there.

 

Jeremy appeared, hands on his hips, still in nothing but a towel. His hair was wet and disheveled, and the water droplets were dancing across his chest illuminated by the light in the room in a way that made him look like something out of a modeling photo session. Brad realized that the man’s features were, at worst, nearly perfection. His smile was subtle and handsome, he had perfect teeth, and his biceps were built and solid. Out from under the dim lights of the dark streets and now in perfect lighting, it was clear that Jeremy was a 10.

 

When Delilah reached up and pulled the towel down away from Jeremy’s hips, Brad realized his looks weren’t the only 10. The man’s cock had to be ten inches long, and thicker than even the monster dildo he’d been practicing on. His eyes fell on the large dick and he was entranced, intimidated, and incredibly humiliated.

 

Delilah slid her hand up and down the thick cock as she stared at it with admiration, cooing. “Isn’t that the most magnificent cock you have ever seen, Brad?”

 

He just swallowed, and managed to croak softly, meekly, “Yes…yes, Delilah.”

 

Jeremy chuckled, obviously not the least bit uncomfortable standing there naked. Then again, Brad reminded himself, if he had a body like that he wouldn’t be uncomfortable standing there naked either.

 

“Suck it,” Delilah ordered, and Brad’s train of thought was broken at once. The command, the tone of her voice, everything about her attitude snapped him into obedience like nothing else. In a flash, he had the man’s cock all the way in his mouth and was bobbing on it, choking on it, eyes shut tight and watering.

 

  

Brad focused on the pleased, content commentary Delilah was making, and tried to ignore the deep moans and feeling of the man’s hands on his head as he sucked the cock. Delilah asked Jeremy how long he could last, and he said “All night baby, all night.” Brad choked and kept sucking, his jaw already burning and aching, the drool already dripping off his chin. Precum filled his mouth a little at a time, mixed with his own spit, and he was nearly in a trance soon, listening to Delilah as she obviously pleasured herself.

 

Licking, tasting her own juices, playing with her pussy, locating her vibe, exploring her clit, playing with herself, touching and teasing her nipples, encouraging Jeremy, “Deeper, deeper, fuck his face, fuck his face hard! He’s a cunt, fuck his mouth harder!”

 

Brad’s head was spinning, his mouth stretched and sore, eyes shut tight. He felt like the center of the universe and kept reminding himself it was all for her, all for her, all for her pleasure, trying to forget that a man’s dick was in his mouth and it was throbbing, pulsing, and could explode at any time and fill him up with cum. Visions of cum dripping from his mouth, gagging him, choking him, or coating his face all haunted him for a moment but he kept sucking hard, listening to Delilah moan and coo in pleasure.

 

While his head was spinning, Brad was barely aware when Delilah pulled Jeremy off of him, away from his face, then flopped the hooker over onto the bed. Apparently, that was that. Brad just remained kneeling there in his pink lingerie, his lips throbbing, his panties tight and wet, as Delilah pounced on Jeremy and in one fluid motion crawled over him and reached into her bag for a condom.

 

The next thing Brad knew, the condom wrapper slapped him in the face and Delilah was giggling, and Jeremy walked over, his big cock glistening and bouncing right in his face.

 

“Put the condom on him,” Delilah ordered, now on her stomach on the bed, her chin in her hands, as if watching a little show. “Little bitch, put the condom on the real cock. Use your TEETH!”

 

Jeremy laughed and said something but stood there patiently as Brad fumbled with the condom wrapper and tried desperately to do as told, perhaps experiencing the largest dose of humiliation ever as he used his mouth to carefully place the condom on the large cock. The condom was too small.

 

After a few attempts, the humiliation overwhelmed him. Jeremy said, “Whose condoms are these! They are too small.”

 

Delilah laughed out loud and came over to investigate and responded, “Oh my God. These condoms are too big for Brad. That’s hysterical. Oh shit. Bitch you might have to go get some bigger condoms!”

 

Brad felt a sickness come over him, realizing he might be shopping late at night for condoms, and of course Delilah, in her current mood, now totally turned on, would surely make it a totally degrading experience.

 

“No I got some,” Jeremy said, turning and walking over to his pile of clothes. Of course, Brad realized, the man traveled with his own, large sized condoms. At least he was a safe hooker.

 

In a matter of moments he returned, but instead of taking the chance to slip the condom on himself, Jeremy shoved the wrapped in Brad’s mouth, obviously enjoying his humiliation just as much as Delilah was. Once again, he found himself fumbling with the condom, trying desperately to put it over the large, thick cock with his mouth.

 

“Go ahead and suck on it a little for good measure,” Delilah ordered, now watching as she played with her pussy, her hair also disheveled, her fine body glistening with perspiration and hot sex.

 

Soon the taste of latex filled Brad’s stretched mouth, and he gagged a couple of times as Jeremy pumped his hips harder, making sure the full length of the shaft entered the slave’s mouth.

 

“Suck his balls, whore,” Delilah ordered. She clearly was now in the mood for a show, before she was going to get fucked, and that could take all night, Brad knew. So he went ahead and obeyed, taking the large heavy balls into his mouth one at a time as the man groaned and panted, complimenting the slave on what a good cocksucker he was.

 

Time became a blur and he lost track of everything, so much so that he was nearly in a different state of mind completely when Delilah once again pulled the hooker off of him and brought him to the bed. She proceeded to first fuck him by straddling him on top, but when his cock proved to be too large, they switched to missionary and finally doggy style, then back to her on top.

 

Brad just remained on the floor obediently, watching, humiliated, as the man pleasured her with his large cock over and over again. If he was indeed gay, he was quite convincing, because his hands enjoyed every inch of her beautiful body and he moved perfectly against her small frame, holding her by the hips as he penetrated her again and again.

 

When he announced that he was about to cum, Delilah encouraged him to cum inside of her. Brad was relieved, for a moment, because he had worried she’d make him cum on Brad’s face, a little trick she loved. But the hooker did cum inside of her pussy, a place Brad had not been in months. He could only fondly reflect on the memory, before she confessed to him that sex was not enjoyable because she could not feel him inside of her due to his tiny size.

 

Giggling, spent, panting, Delilah rolled over on top of Jeremy, who was panting also, and slid the condom off his cock. A huge load of white cum filled the tip and the entire condom was slick and disgusting. Brad watched, mortified, as she carried it over to him. “Want to taste my pussy, Brad?”

 

  

How could he answer such a question? It was the ultimate trick question. The question was designed to be his undoing. But he could not lie to her. “Yes, Delilah, I want to taste your pussy.”

 

“Open wide,” she ordered, holding the condom with two fingers as if totally disgusted, looking at it with a wrinkled nose but a huge smile. “Open up and get a big taste!”

 

Brad shut his eyes tight and opened his mouth obediently. Soon his tongue was heavy and he felt a big, thick glob of latex, pussy and cum in his mouth.

 

“Chew it, suck it!” she ordered, holding his chin closed. Her hands were warm and smelled like pussy, like sex. He felt cum oozing into the corners of his mouth. The taste of pussy was there, but mostly, it was all mansex and sweat, and the thick, slick taste of a large load of cum that was not his own. He started to gag.

 

“If you spit it out or throw up you are drinking a pissload!” she threatened. “You know how much I would love to see it washed down with a load of piss from him.”

 

It took all of Brad’s resolve to not throw up or spit it out. He kept his eyes closed and focused on the taste of her pussy, however faint it was. She made him sit there for quite some time until he sucked and chewed the condom. Then she threatened to make him swallow it and had him about to do it before she laughed and told him to spit it into the trash.

 

Jeremy was up and back in the shower, and Brad was not even aware of hearing him get up or go there. The clock read 4:35am. His cock was aching in the tight pink panties and his knees were sore. Delilah was flitting around the room on cloud nine, listening to music, dancing naked, then admiring Jeremy as he toweled off in the bathroom doorway.

 

For the final humiliation, Delilah came over and ordered Brad to pay the hooker. She picked up the large stack of bills, Brad’s money, and shoved it into his hands. “Crawl over and pay the prostitute and thank him for letting you suck his dick and for fucking your girlfriend the way she deserves to be fucked – by a real man!”

 

Brad looked at the stack of bills. Hundreds, thousands of dollars. He crawled over to the hooker, who was standing there naked, his thick cock erect again already. Jeremy was smiling with his arms folded over his chest, amused.

 

Jeremy looked past the kneeling man and listened to his little speech, then nodded at Delilah, “I don’t have to leave just yet, you know. You want to go again? You want to party?”

 

Delilah walked over and Brad felt her hand behind his head, her fingers twirling in his hair. “That’s ok dear. I enjoyed it, but I need a little alone time with my whore now. Even tiny little dicks need attention now and then, after all.”

 

Jeremy chuckled and took the wad of money, stuffing it into his pocket. “Your call,” he smiled. “Thanks. See you around.”

 

With that, he started to collect his clothes, and Brad found himself feeling warm, content inside. Not because of the extreme humiliation that always cleansed him and made him feel so raw and alive, but because of the nurturing feeling of her fingers in his hair, and the contentment he felt as she sent the perfectly chiseled man with the huge cock away so she could spend time alone with her slave.

 

To reward him, maybe. Maybe she would let him cum, or let him taste her, but maybe not. Still, the moment she sent the third man away was always the time he felt whole again, realizing the bond they shared. After all, Jeremy was the one pushing the button on the elevator, and Brad was the one curled up at her feet.

  

  

  

  

  

  

  

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