“Good evening. Is this Ms. Croft I'm speaking to?”
“That's correct.”
“Wonderful to hear from you again! What can we do for you this evening?”
“I'm at the Pan Pacific Hotel in Mariana Square. Room 1612. I'd like some company for the evening.”
“Very good, Miss. Did you have something different in mind for tonight? Or the usual?”
“The usual, please.”
“A fit young man, no older than thirty nine. The rest is of no concern?”
“Yes, except...”
“Ahh, it says here you prefer someone willing to submit and engage in kinky play?”
“It's a must, for me.”
“That can certainly be arranged. Since you've used our service before, you probably already know, but that kind of entertainment invokes our premium fee of five thousand dollars.”
“That's fine.”
“Excellent! Your billing information is the same?”
“Mmmhmmm.”
“Splendid. I'll run the charge and have someone sent to your room within the hour!”
“Thank you, darling.”
* * * * *
“Hello?”
“Dan! So glad you're there! I know you're not on tonight, but please tell me you're available right now?!?”
“I was about to head out to a club, but I can work if you need me.”
“I really do! You're OK with kinky shit, right?”
“That's an awfully broad term. What kind of kinky shit?”
“You know! Women who like to domme!”
“Oh. Hell yeah! I'm down for that, as long as she's not into torture, scat or anything too extreme.”
“If she makes any unreasonable requests you can always bail, but I don't think you'll want to. This date is two thousand in your pocket.”
“DAYUM! You gotta get me gigs like this more often! Where am I going?”
“The Pan Pacific. Room 1612. The woman is a Ms. Croft. Just have them dial her from the front desk and they should bring you right up.”
“I'll leave in five minutes.”
“Good. I already burned twenty making phone calls and she wants you there in thirty. Don't keep her waiting!”
* * * * *
*DING*
“This place is crazy” Dan remarked as he stepped off the elevator, just behind the hotel concierge. “I can't imagine a stay here is cheap.”
“Our deluxe suites start at five hundred a night” the middle aged gentleman in the scarlet red jacket and brimless cap replied.
“Do you always ferry people up to the guest's room like this?”
“If our clients request it, yes.”
“Damn. First class all the way.”
After a short jaunt down the hall, they arrived at room 1612. The concierge swiped his key-card and the door opened to almost total darkness. There were faint lights radiating from distant buildings through the windows toward the back, but that was all that could be seen. The smartly dressed steward motioned for him to step inside.
Dan's brow furrowed as he peered into the dark room. “Are you sure she's here?”
“Come in, young man” a female voice called from inside. They were sultry tones spoken in a haughty British accent.
Dan stepped inside and the concierge took his leave. The pneumatic device pressed the heavy door closed and re-established its air-tight seal as he walked down the short hallway to where the room opened up.
Once through the foyer, Dan was in a dark but spacious room with a beautiful view of the city below. The night sky was lit up with other fancy hotels and office buildings casting their glow into the evening gloom. In the corner of the room he could decipher the outline of a woman sitting in a chair with a drink in her hand.
“Hi there. I'm Dan.”
“Hello Dan. Is that short for Daniel?”
“It is, but only my mother calls me that.”
The woman took a sip of her drink. “Do you mind if I call you Daniel? I despise shortened names.”
“Sure. If you like.”
“Thank you, dear. My name is Lara.”
“Lara?” Dan asked, walking a bit further into the room. “That's a lovely name. I hope I get to see the lovely face that goes with it.”
Lara emitted a low chuckle. “In time. So, you enjoy submitting to a strong woman, do you?”
“I live for it” Dan lied. He didn't mind doing it, especially when the pay was good, but it wasn't really his thing. However, he knew part of being a good escort was playing into the client's desires.
“Glad to hear it. Take off your clothes. You can leave them on the bed.”
Lara took a long sip of her drink as Dan disrobed. She savored the fine wine as she watched the outline of the young man undressing in the darkness.
“In the world of kink, it's important to be open to new experiences. Are you open to new experiences, Daniel?”
“I try to be” he replied as he removed his pants and tossed them to the edge of the bed. He was now completely nude and standing in the middle of a dark hotel room conversing with a total stranger. His previous clients had enjoyed many different forms of foreplay, but none of them had been quite so 'cloak and dagger' as this. It was already a new experience.
His pride and joy hung out in the open, a flaccid four inches. He wasn't huge, especially when soft, but Dan had never been self-conscious. He had a swimmer's body and he knew once Lara got him going, his manhood would harden to a much more impressive seven and a half. He'd been told by many women that he was the perfect size.
“Good. That's an important quality in a man-slut. Lights!”
With her command, the overhead lights blinked on. The room was cast in dim illumination. Dan's eyes went wide and his mouth dropped open.
Lara was a stunning beauty. She had lovely brunette hair that trailed down both sides of her face and sprouted into a ponytail behind her. Her eyes were cold and surrounded by dark liner that gave her a killer “femme fatale” look. Her leather top, a garment that covered her shoulders and upper arms, was the only article of clothing she wore. The shiny leather stopped where large, round, supple breasts took over, jutting out from her chest.
Her well toned stomach and surprisingly strong thighs were evidence of someone who spent time at the gym. Perhaps she was a rock climber or a fan of other “extreme” sports. Her leather boots had been cast aside and the rest of her leather outfit was strewn all over the floor.
None of this was the cause of Dan's silence. What paralyzed him from the moment the lights came on was the gigantic cock and weighty set of balls situated between her powerful legs. It was gargantuan. Probably twice Dan's length at his hardest and three times as thick. It didn't even seem possible.
The young escort stood there staring in disbelief as Lara eyed him with a devilish smile. She looked down at his soft unit before returning her gaze to his eyes. Her amusement was obvious.
“I'm... Wow. I think there's been a mistake!”
“A mistake? Whatever do you mean?”
“I don't know how to say this without sounding rude... I'm not gay.”
“That's a relief” she responded before draining her glass and setting it down on the window ledge. “I'm not gay either. If I was, I 'd have asked for a woman.”
Dan's brain blew a fuse. He had no idea how to respond to that. As he eyed her youthful body up and down, he recalled a conversation with some of his colleagues. They had encountered women whose wealth allowed them to remain vital despite their age and whose bodies had been “augmented.”
These days, there was no shortage of gene therapies, enhancement drugs and surgeries that people of great means could harness to extend their lives and improve their physique. Lara could be young, or she could be eighty years old with the mind and body of someone in her early thirties.
Trans-humanism was running rampant in this brave new age. By and large, it only existed for the wealthy. Everyone on the bottom rungs of society was still just an ordinary human living in their world and trying to get by.
“What's the matter, Daniel? Don't you like my body?” She gave her breasts a firm squeeze and then moved her right hand down to her massive cum pipe. Lara seized it and began stroking it up and down lewdly. “This isn't going to be a problem, is it?”
Dan swallowed. This was his first time encountering a woman like Lara, but it probably wouldn't be his last. If he canceled the date now, it would look bad for him at the agency. He might not get anymore high paying gigs. He'd been pegged before. This would only be slightly different. It was time to suck it up... literally and figuratively.
“No. There's no problem. And your body is amazing.”
That got another throaty chuckle from the well hung Domina. “Good. Now get over here.”
She made the 'come hither' motion with her index finger as Dan closed in on her nude, seated form. She continued stroking herself as she watched the trim, naked fuck toy approach. Lara was beginning to get the sense that submission wasn't Dan's natural leaning. That only turned her on more.
“On your knees.”
Dan lowered himself down gently between her legs. He knelt at the foot of her seat, looking up at the impossibly large club of meat standing at attention before him. He had no idea how he was going to handle that monster.
Lara didn't give him long to think about it. She brought the tip of her fat, fleshy weapon to his waiting lips. The lustful Domina reached forward with both hands and seized the back of his head. She pulled forward gently and Dan's lips parted. Her hot, pulsing member plunged into his oral cavity and ran down the length of his tongue.
Dan's first taste of cock was musky with strong hints of sweat and leather. It was obvious Lara hadn't showered before their encounter. Whatever she'd been doing earlier that day, she'd sweated in her leather attire and now he was awash in her taste and smell. She pushed and pulled on his head firmly, beginning to fuck his mouth with the first six inches of her glistening weapon.
“There we go... now start sucking.”
Dan obliged, putting his tongue and the walls of his mouth to work. Wet noises squelched from his cheeks as he began to suck her glans and weighty shaft with vigor. Lara tilted her head back and let out a long, low moan. She kept her hands on his head, guiding his motions as she slowly fed him more of her gargantuan penis.
“Mmmmmm, yes... And just like that, a cock sucker is born! I can tell this is your first time, but I bet it won't be your last. Most of the men I fuck grow to love it. I think half of them would pay me for a date, now. But that's no fun... I enjoy breaking in fresh boy pussy.”
Dan's cheeks burned with embarrassment as his lips stretched over her girth and he slurped up and down her increasingly hard cock. Her grip on his head was tightening, her mouth fucking becoming more insistent as she tried to plunge ever more of her fat dick into his sucking mouth. Her glans kept bumping into the back of his throat, eliciting gagging sounds as she established a steady face-fucking rhythm.
This went on for many minutes before Lara pulled his face off her cock. Dan coughed and retched; trails of spittle and pre-cum decorated his face and leaked from his wet lips to the floor below. Lara reached into her leather half-vest and extracted an XXXL condom. She held it out to her rented bitch-boy and eyed him sternly.
“Put it on me.”
Dan unwrapped the absurdly large condom and rolled the latex sleeve down her rock-hard length. Even through the cool latex, he could feel her shaft smoldering with lustful warmth. Her weapon now sheathed in thin rubber, Lara rose to her feet. She grabbed Dan by the hair and pulled him up with her.
Wasting no time, she half-guided, half-dragged Dan the short distance to the window and pushed him up against the glass. Dan got a dizzying view of the city below as Lara licked two of her fingers and speared them into his soft pucker. He groaned as she pressed him against the glass harshly, his anxiety skyrocketing. Only the window pane separated him from a sixteenth floor fall to oblivion.
The cock-wielding nympho spoke directly into his ear. “You said only your mother calls you Daniel, yes?”
“Yes...” he grunted through the rough thrusts of her fingers up his ass.
“Well then, I guess that makes me your mother, doesn't it?”
“Ahhhhhh!!!”
He cried out as she added a third finger, her digits sloppily thrusting in and out of his quickly expanding anus. “Say it. Call me your mum.”
“Yes, Mommy!”
Lara's libido surged and she couldn't wait any longer. She removed her slick fingers and brought the fat tip of her hot weapon to his waiting pucker. She seized his hips and shoved it in aggressively, burying herself halfway in the first thrust. Dan groaned in pain, the heat and tightness of her invasion overwhelming him. His hands clawed on the glass, finding nothing to hold onto.
Lara began bucking in and out of his soft, fleshy ring. His pucker expanded with each forceful fuck as she smacked him into the window with hungry thrusts.
“Relax, slut. It will start to feel good very soon. Then you'll be begging for my cock!”
She brought her right hand to the back of his head and seized his hair again. Her left hand remained at his side, holding him firm as she speared deeper into his ass with each powerful stroke. Her strong legs proved more than adequate to keep him pinned to the window, his face plastered against the glass as she drilled him hard.
Within minutes, the burning sensation started to fade along with Dan's pained groans. Her fucking became more steady and smooth as her latex wrapped schlong slurped in and out of his yielding hole. Dan started moaning as her girth plowed across his prostate. He'd felt this before when women fucked him with strapons, but never this full or intense. His every inhibition faded away and he began muttering like a cock-craving whore as Lara grinned and fucked him ever harder.
“Mmmmhmmm... See, Mummy knows best.”
She released his hair and moved her right hand to his stiff cock. Dan had been so focused on her anal assault that he hadn't even realized how hard he'd grown. She stroked him back and forth as her fucking became shorter and choppier, a full two thirds of her fat length jammed in his body.
“Cum for me, cock slave! Cum with my big dick in your slutty ass!”
It didn't take long for her furious stroking to set him off and the young man moaned out his climax. Thick ropes of jizzum shot all over the window and dripped down on the ledge below. Once she'd milked his cock dry, Lara released his member and returned her hand to his hips. She began fucking him faster and much more aggressively. She yelled and grunted like an animal, digging her fingers into his flesh and burying her length in his welcoming walls with ferocious hunger.
“UUUUUNNNNNHHHHHHHHHHHHHHH!!!!”
She thrust her cock deeply, gritted her teeth and pushed Dan up against the glass. He could feel the warm gunk hosing into the end of the condom buried deep in his insides. Lara let out multiple loud moans as her breasts pressed against his back and she kept herself hilted in his ass for long moments. Her cock throbbed as ounce after ounce of buttery nut spat into his flesh-packed depths.
After a minute of heavy breathing with her chin on his shoulder, Lara backed up. She pulled out of his ass with a wet slurch and freed Dan from her grip. She put her hands on her hips and looked down at the large pocket of cum dangling from the end of her cock. A satisfied smile spread across her face and she let out a rapturous sigh of contentment.
“That was lovely, my dear. Move to the bed. You can have a few minutes to rest.”
Dan turned and gazed at the wicked shemale. Lara was pouring herself another glass of wine and eyeing him hungrily. It seemed hard to believe that she wouldn't be sated after what they'd just done, but her demeanor was a clear indication that the date was far from over.
He walked to the bed gingerly, his ass still aching from being stretched so roughly. He brushed his clothes aside and sat down before lying back, his cock going limp as he stretched out. Lara downed another glass of her bubbly in between strokes of her greasy pole.
She set her cup down before moving to her luggage and extracting a pair of handcuffs. Lara strolled toward the bed, reaching out with her hand and gesturing to Dan.
“Turn over. Hands behind your back.”
Dan complied and she was on top of him in no time. She clicked the cuffs into place and secured his hands behind him. Lara rolled him onto his back before grabbing him under the arms and dragging him to the end of the bed. He was now looking at the well-endowed Goddess upside down, his head hanging just over the edge.
Lara pulled the condom from her half-limp cock and examined the weighty balloon of cum.
“Five thousand dollars should buy a lot of pleasure, don't you think, Daniel?”
“Yes, Mommy.”
Lara positioned the bottom of the condom over his chin before turning it over and emptying its slimy contents all over his face. The thick, gunky gruel dribbled over his mouth, nose and eyes before running through his hair in creamy streams. She smeared the thick paste all over his face before inserting her fingers into his mouth. She didn't even need to tell him to suck. Dan knew what she wanted.
“I'm glad we understand each other. Unlike your unfortunate anatomy, mine doesn't suffer from a refractory period. As far as I'm concerned, you're on the clock for the rest of the night and I'm going to make use of every minute.”
She pulled her spit shined digits free and lined up the head of her cock with his waiting lips. Lara drove her shaft home into his hot, sucking mouth. In this position, his throat was perfectly aligned with her glistening length and Lara knew she'd be able to bury even more of her fat phallus in her cuffed oral slave. All he could taste was cum, latex and sweaty cock as she began to fuck his face in earnest.
“MMMMMM... I do love exploring warm, wet places. It's what I do, for business and pleasure.”
Dan couldn't respond as a foot of cum-slick schlong speared deep into his gullet. He felt light pain in his nipples as Lara reached down and began twisting them fiendishly. His hands yanked on the tight metal handcuffs pressed against the bed below his back. Her cock slid sloppily in and out of his sucking maw, her fat scrotum drawing ever closer to his cum spattered brow.
The young escort spluttered and gagged as his second ordeal began. Cum ran from his face as Lara plugged his throat with musty dick and extracted divine pleasure from her bound slut-boy. She gathered the sides of his head and thrust deeply, beginning the lengthy throat-fuck that would lead to a second deluge of hot jizz.
It was going to be a long night.
- - - - - - - - - -
I write a new "quickie" short story every month. Half of them will be made available here for free. The other half are only for my patrons!
If you enjoy my work, wish to support it and want to read all my latest stories, check out my Patreon! (Do an internet search for "Patreon James Bondage".)
Thanks for reading! Your votes and feedback are always appreciated!