Room Service Anal Girl

Room Service Anal Girl

As floor manager for the executive suites, presenting the gift was an opportunity Sophia simply couldn't miss. All she knew was that the CEO's eldest son had recently been hired as a Director for the hotel franchise, and that a special gift was being prepared upon his arrival.

It was almost 10 pm and he had just checked in. Normally the role of gift giving for special guests was reserved for a particular member of the room service staff.

But given the magnitude of the guest, a man who in all likelihood would become CEO of the hotel chain someday, Sophia took it upon herself to make the delivery. And why not? In her mid-30's, she was definitely a head turner, and her people skills are also top notch. Besides, she was certain that, if given the chance, most people would be willing to usurp the opportunity from colleagues to kiss up to upper management. 

Isn't climbing the corporate ladder what this country is all about?

Whenever she made a personal trip to the executive suites, she always took a moment to fix herself in the bathroom. Everything looked satisfactory. Her makeup was on point. Her long hair was neatly tied. And her uniform showcased her figure, which had curves in all the right places.

It would be the perfect first impression of herself.

At 10:15, she felt it was the right time to deliver the gift, after he had settled in. He knew the gift was coming too.

The gift itself was placed on a service cart. It was a basket with a bouquet of red roses, some expensive wine, desserts, goodies, and a personalized note from the general manager.

Sophia took the cart and made her way to the suites. As always, she mentally rehearsed her canned lines. She even practiced jokes and playful banter in her head.

When she reached the floor, she wondered what kind of guy she'd be dealing with. With executive types, you never know. And as a woman in the hotel business for nearly 6 years, Sophia had heard all the pickup lines, especially when dealing with high powered men who were used to fucking anything with a pair of tits.

And each time, she knew exactly how to handle herself, using sweet talk, charm, and clever maneuvering to work her way out of anything. With that much confidence, she was fearless.

Finally, she stood in front of his suite. She took a moment to fix her posture and outfit before knocking. It wasn't long before he answered the door.

Sophia was pleasantly surprised by what she saw; a guy in his late 30's, she estimated, handsome, and his suit was half removed. He only wore his buttoned shirt, the top collar undone, and his slacks. A quick glance at his fingers showed that he was unmarried (which in Sophia's world meant that he was single, girlfriends be damned).

"Your gift, Mr. Hartford," she smiled politely, gesturing to the service cart.

His smile was equally as bright. "Thank you. And your name is?"

"Sophia, sir."

He extended a handshake. "Pleasure to meet you, Sophia. And please, call me Derek. It's too late in the night for proper formalities. Right this way."

After shaking hands, Sofia entered the room to put the gift inside somewhere. The standards of the hotel were high, and in the executive suite, it was even better. It always marveled her and grabbed her attention. She sometimes joked with her boss that she'd love to live in a hotel suite if she could pay a fair amount for rent.

She noticed that Derek's luggage was still untouched, and that his blazer and tie were folded and placed on a chair. She placed the gift items on the table. She wondered where Derek's eyes were at the moment, if he was gazing at her backside while she worked. The idea kind of turned her on. 

She also wondered if Derek would attempt to make a move on her. She hadn't figured that he'd be the type to do such a thing. She saw him as a complete gentleman, but at this hour, you never really know...

"Apparently you have a note for me," Derek said, approaching from behind.

Sophia picked out the card attached to the flowers. "Right. This is from Mr. Wymer, our general manager."

"Thank you," he said, taking the card when it was handed to him. "Judging by your outfit, I'd say you're a manager here as well."

Being called a manager always made her smile. "Yes, Derek. I'm the floor manager here."

"Hmmm...." He thought for a moment. "I heard about the kind of surprise I'd be getting. I just didn't think they'd send a manager for this."

"I wanted to bring this to you personally. I like to service certain clients myself whenever I have extra time on my hands."

He gave a suggestive look. "That's very kind."

As he took a quick glance over her body and smiled to himself, she wondered if this was the part where he'd put the moves on her. It had been a while since she had last gotten laid, and the idea kind of excited her.

But as he opened the note, Derek appeared to behave himself, so she pushed those inappropriate thoughts away and tried to be professional about this, finishing up her duty to neatly place the gifts on the table.

Right when she finished, she heard a brief laugh. She turned to see Derek utterly amused while reading the note.

"Anything good?" she asked.

"Your boss. The guy is a cheeky bastard, you know that? Well, you must know, you work with him everyday."

She joked back, "Mr. Wymer certainly has a way with words. He does have a nice sense of humor, which is a great attribute to have in a boss."

Once again, Derek gave her a look-over, making her wonder just what the hell was on that note.

"Would you like to know what Mr. Wymer wrote?" he asked.

Sophia tried to keep her curious nature at bay and kept herself composed. With all this build up, and the way Derek had been acting, it must have been something good. And it must have been about her in some way.

"It's a private note, but if you want to share, I'd be happy to hear it."

Derek looked at the note and read from it, "Dear Mr. Hartford, congratulations on your promotion. We're very excited to have you here. Yada... Yada... Yada... I'll spare you the boring formalities and get the point, if you don't mind."

"Of course."

Derek read again: "My room service girl is quite special. We have a unique relationship after discovering our similar interests. Since then, we've been open with many things. And we've both agreed that sharing is fun."

The letter nearly caused Sophia to choke, and she gulped hard to keep herself composed in a professional manner.

"Is everything okay?" he asked.

"Yes, I'm fine. Thank you for asking."

"Should I stop reading? We haven't gotten to the best part yet."

Sophia nearly choked again. "That's not the best part?"

"No, this guy has a real sense of humor. I'll skip straight to the main point."

This, Sophia had to hear.

"Go on," she said with a forced smile.

Derek continued reading: "Being in the hotel business means constantly having to deal with assholes. On a daily... no.... hourly basis. In all likelihood, Derek, you'll be in charge of this great hotel empire someday, and these assholes will be your problem. To blow off some steam, how about an asshole to fuck? The woman before you has the perfect body to accompany her perfect hole. Yours for the fucking."

He chuckled again at those last few words.

Never in Sophia's life had her stomach dropped so fast. She instantly realized that she made a horrible mistake stealing this room service duty away from Christine. 

Speaking of Christine, what the hell was this about? Had Christine been plotting to take over a management position by sleeping her way to the top? How nasty. How tasteless. How cunning. How so very smart of her. 

Sophia couldn't help but admire the exciting sex life and ambition of her employee Christine.

"Are you okay?" he asked with genuine concern.

Sophia forced another smile. "I'm fine. That Mr. Wymer is hilarious. He's a little old for these types of pranks, I think."

"I'll have a discussion with him about his inappropriateness. In the meantime, do you have a preference for lubrication?"

"For?" she gulped.

"Anal sex. What else?"

Her heart nearly stopped as Derek went to the gift basket. Inside some of the wrapped goodies were small containers of body lotions and lubricants, which she had come to find as he opened each one and placed them upright on the table.

It puzzled her as to why she hadn't straightened this whole mess out yet. Casual sex had never been her thing. And although Derek seemed eager to fuck, she was certain that he'd understand. He seemed like a real gentleman about sex and caring for a woman's needs.

More importantly, anal sex wasn't her thing either! It wasn't that she was afraid of it, or that her tiny opening couldn't handle it. It was more that she never trusted a guy enough to actually fuck her there, which included men she had been in love with in the past. A woman's rectum is an extremely delicate matter.

"Sophia?" he asked when the lubes were neatly arranged.

She snapped out of her self-reflection. "Oh, sorry. What do you want me to say?"

Instantly, he sensed apprehension in the room and casually approached her, while she stood her ground. He studied her eyes and facial expressions very carefully, as if he had done this sort of thing with strangers before. Sophia couldn't be certain.

"Are you really the room service girl?" he asked. "The one mentioned in the letter?"

She thought fast. At this point, admitting fault would have led to a domino effect, which would embarrass herself along with her boss and the 'real' room service girl who was supposed to be here.

Being the trooper that she was, she decided to bite the bullet. She may or may not regret it. But she was extremely aroused by him and the situation. And her pussy was extremely wet as well (which was ironic, because apparently he wouldn't be focusing on that area tonight).

"That all depends," she said, inhabiting the role.

"On?"

"How well you can handle a woman's posterior."

He laughed. "Posterior, exterior, interior. When it comes to women, let's just say that I know what I'm doing."

"I'm serious."

"You don't think I can handle a woman's anus?"

Sophia raised an eyebrow. "Can you? Do you have a lot of experience with female assholes? Literally, I mean."

In that moment, Derek seemed as confident as ever. 

"I have a lot of experience with a lot of things. It's getting late, so why don't we get started? Judging by your reaction, I'd say you're a little cautious with that region. Bad experiences?"

She shook her head. "I don't have enough experience there to even have a bad one."

"Ah, okay. Anal virgin, then."

She nodded. "I love sex as much as anyone else, but I'm careful with how I treat my body. Or maybe I'm just a little scared. Can you blame me?"

"Not at all," he said with a sly smile. "Anal sex can be daunting, especially when the man is inexperienced in what he's doing, and the woman has never had anything there before."

"Why do I get the feeling that you're some kind of anal sexpert?"

"I'll show you when you take off your uniform," he said, which sounded more like a command. "It's a nice uniform and it looks great on you, but you definitely won't need it. Leave your stockings and heels on though. I like those."

It was another crossroad for Sophia. There were options, sure. She could just admit that she was the wrong girl, and maybe bring in the right girl, which would be embarrassing for everyone. She could politely decline. Or she could tell him to fuck off, and if he gave her shit, she could use some of the advanced techniques she had learned in her kickboxing fitness class at the gym.

Maybe, she could just do what he wanted and take off her hotel uniform. The idea of fucking him was still very much intriguing. As for the anal part of all this? The human body has many pleasure spots, and apparently the anus is one of them. She knew she was going to lose her anal virginity eventually. Why not with an expert? Assuming Derek was as competent as he sounded.

What swayed her decision most of all was her own arousal. She wondered if Derek could smell her aroma.

Her fingers hesitantly went to her uniform. "You won't tell anyone, will you?"

"Why would I do that?"

She pinched a button on her outfit. "Men like to brag with each other. And I've worked hard for my reputation. Honestly, I didn't sleep my way up the corporate ladder. I busted my ass working."

"No pun intended," he quipped.

She smiled, "You know what I meant."

"Look, Sophia, I'm very discreet. With my family name, the last thing I want is rumors spreading around. It's bad for business."

Derek finalized the decision for her, reaching to undo her buttons. It was a decision that Sophia thought was gutsy. At any other time, she would have thrown a knee strike to his groin, the kind her instructor would be proud of. As it just so happened, Derek's advance came at the right, perfectly timed moment when her sexual defenses were down.

He continued, "I'm very dominant. I like being in charge in the bedroom. I like taking control. And I like being the best sex a woman has ever had."

Sophia breathed a little deeper. "Those sounds like bold promises. You'll fit in as a Director for this corporation."

Her top was undone, and Derek went to her skirt.

"Work hard, play hard. That's a motto I've always lived by. And after the day I've had, it's time for some fun."

The unraveling was easy. Sophia's neatly ironed uniform had been tossed to the floor like it was nothing. In a manner of moments, Sophia went from an impeccably dressed floor manager, to a woman standing in her bra, panties, stockings, and heels. The perfect plaything.

His eyes roamed her beauty, making her even more aroused.

"You never answered my earlier question," he said. "What kind of lubrication do you like?"

She gave a soft sigh. "You're the supposedly dominant sexpert. You decide."

"You sound like you're mocking me."

"Maybe I'm challenging you to live up to those high expectations."

A mischievous grin appeared on Derek's face. This was a game he liked playing.

"On the bed," he said. "Face down. Ass up. If you want to play, we'll play."

She smiled, "Whatever you say, Mr. Hartford."

As she turned to walk to the bed, Derek suddenly put a hand on her shoulder.

"Wait. I have an idea."

He reached to the chair where his blazer and necktie laid. He grabbed his necktie and Sophia instantly knew what his game was. Being blindfolded was something she had done before. 

Sophia's face showed delight as Derek wrapped the necktie around her eyes and tied a soft knot in back, blindfolding her completely.

"This will heighten your other senses," he said. "I want your first anal fuck to be something memorable."

"This is memorable already."

He brought his lips to Sophia's ear. "Do whatever I say. Follow my lead. Trust me, this will be something new."

A shiver went down her spine. At this point, she was certain that her natural aroma was permeating the room.

"You really know what you're doing," she replied in a tone that showed her pleasure.

He began softly rubbing her butt.

"In my experience," he said. "Most people's fantasies revolve around dominance and submission. I've always enjoyed the dominant role. And I think I'm good at it because I understand women's inherent desires. As for you, you seem like the kind of woman who loves being in charge all day, so therefore I'm going to give you the opposite. I'm taking control and all you have to do is present your lovely ass to me. And it is a lovely bottom to say the least."

Without warning, he pulled her panties down to her ankles, then she stepped out of them. She was glad she'd shaved a day earlier. And she was certain the shape of her butt was up to par for his presumably high standards. She wondered how hard he gazed at her private parts. Anything less than an eye-fucking would be an insult to her.

And Derek was right, she thought. The blindfold had enhanced her other senses and she could feel his hands on her butt so acutely. When his hands moved away, she also became keenly aware of the sound of a bottle cap opening.

"What are you doing?" she asked.

"I'm going to lead you to bed by your asshole," he said, "Consider this your prep. I find that silicone lubrication works best for this."

Had that actually been in the gift basket? Sophia's knowledge of lubrication was limited. She had always been a naturally wet girl, so she left the science to the professional in the room.

He then ordered, "Spread your legs while you stand there."

With her senses still heightened, she spread her legs, just enough so that she could stand upright while he could do... whatever... to her asshole. Sure enough, she felt his slick two fingers squeeze between her butt cheeks.

"Be still," he said, holding onto Sophia's shoulder with his free hand. "Relax while I put my fingers in."

She did her best. She held still and relaxed her posterior muscles and anus while the cold, lubed fingers wiggled their way in to the tight hole. It was mildly ticklish and extremely uncomfortable when the fingers pushed past her anus and dug into her rectum. There was a lot of lubrication on his fingers, which made the process easier. The fingers pushed her rectal walls apart, causing her to gasp.

"Now walk with me," he said. "I'll guide you."

With his fingers hooked inside her rectum, he led her to the bed. It felt so strange walking like this. Her rectal muscles felt hampered and her anus felt overwhelmed. With each step, she could swear she was getting looser.

Sophia got in the position she had been ordered, while his two fingers were still buried in her asshole. She was on all fours, sideways on the bed, and she laid her face down and had her butt facing up. Her stockings covered calves and heels hung off the bed. It was the perfect prone position. 

"How do you feel?" he asked, crooking his fingers inside of her rectum.

She got comfortable with her face down and enjoyed the anal play. "Like I'm your toy."

"My fuck toy. You're a fit woman. I'm sure you can hold this pose long enough."

Derek pulled his fingers away, and suddenly Sophia felt a cold gaping feeling in her ass. She had suddenly wanted him back. Her senses were heightened alright. In this position, she wondered what Derek's eyes were doing, if he was gazing deep inside of her asshole and wet pussy.

She heard the sound of his pants being unzipped, then to her surprise, she felt his lips kissing around her bent over bottom. Then his lips kissed her wet pussy across her labia. With his two dry fingers, he slipped inside of her pussy and stroked her g-spot. Finally! The pleasure she had so longed for.

"It helps when the person on the receiving end is extremely aroused," he said. "It keeps the rectum nice and loose."

Sophia smiled at the blissful feeling of g-spot stimulation. "You really are an expert at this."

His fingers worked hard and fast, hitting her most sensitive of areas. Most women take a while to climax, and sometimes Sophia needed time, but she was so aroused and caught up in the moment that it flowed effortlessly. Derek sensed this and worked fast to bring her to cum. Her toes curled inside her heels and her face grimaced. The orgasm was quick and intense, satisfying most of her urges, but not all of them...

As her body relaxed, her mind was still curious, and her asshole had already been prepped for a fucking.

Derek's fingers pulled out of her pussy, wet with her orgasm, and she heard him rubbing himself with those very fluids.

'Smart man,' she thought. 'Kinky too.'

The idea of his cock laced with her cum was hot. And her body tensed when she felt the head of his penis against her lubed, puckered hole.

"Be still," he said. "I'm going to insert myself slowly. When you're ready, I'm going to fuck you hard."

She felt a slight panic as she laid face down with her ass pointed upwards to him. Derek used his fingers to push his cock head inside of Sophia's anus. Before this, the most she had ever taken were a few fingers by ex-boyfriends, and more recently Derek a few minutes ago.

Feeling a thick cock shoved in her asshole was something else entirely. Her feet squirmed as they hung off the bed. Her back felt uncomfortable from her own tensing. She tried to relax. She tried to keep her body calm and her anus unclenched.

With the blindfold on, her senses remained high. She felt every stretch, every push, every centimeter and inch as the hard erection slide inside of her tiny hole. Derek used his hands to guide his shaft in. 

"That's it," he said. "That's it. Take it. We're almost there."

It felt extremely uncomfortable and slightly painful in her ass. Yet the feeling was also unique and weirdly pleasurable. It stimulated nerve endings she never knew existed. And she felt a fullness inside her body she had never felt before. When the cock gently continued its journey all the way inside of her, Sophia felt as though her sexuality was pushed to a new, uncharted limit.

"How does that feel?" he asked, with his crotch now firmly pressed against her butt.

"It hurts. But..."

"But what?"

"Fuck me. Slowly."

His hands rubbed her bottom. "I'll give you what you can handle. Nothing more. Nothing less."

Derek slowly rocked his hips. With each gyration, his cock pulled back a little further, giving her a sad feeling of emptiness. With each push, he went deep, filling that tight little hole again.

"I love anal virgins," he said, working his cock in her ass. "It makes things more enjoyable for me."

Sophia struggled to speak as her ass was being stuffed. "Is that what this is about? Oh....uh....your ego and your pleasure..."

He slapped her ass while fucking her. Then he slapped it again. He squeezed her hips and took greater control of her body. With each thrust he stretched and fucked her harder.

"We're in the same business," he said, sliding in and out of her asshole. "The customer service business. I aim to please, just like you. I can tell you're enjoying this. A beautiful, professional woman like you is just what I needed. Go on, tell me you love my cock. Tell me you love having it inside your ass."

Sophia clenched the bedsheets. "I love your cock in my asshole."

He slapped her ass again. This time, so hard it made her body jolt. He reached forward and held both of Sophia's hands, so that she had no support, and her face was buried on the bed sheet.

She cried when he fucked her asshole more aggressively. Cries of pleasure as her newfound nerve endings were being stimulated and stretched and spread in ways she never thought possible. It was intense and it filled up her body in an unparalleled way. 

"You're going to cum again," he said confidently, holding her hands tightly as he really went at it.

Sophia couldn't dispute that, but she wondered how it was possible. Sure, she had heard of anal orgasms before, but she had always assumed that she wasn't that type of girl. But as the intense pressure built inside her bottom and those hidden nerve endings were being heated, she began to wonder if she could actually cum again.

"Let it all go," he said, thrusting deep. "I want you to ruin my bed. Relax. Cum for me."

She clenched her blindfolded eyes shut. Her face grimaced and she clenched her teeth while moaning. It took several more thrusts of his hard cock in her asshole before she had her first anal orgasm. Her bottom felt a warm sensation, which was sort of like a tingle. It was an internal feeling at first, and then it was like a spark that set off a flame of divine spasms which she'd never forget. Without having her pussy touched, she trickled fluids onto the bed from her intense anal climax.

"Oh god," she whimpered, before her body nearly went limp.

Derek kept on fucking as Sophia's legs turned weak. He fucked her asshole until it was his turn to orgasm, and he grunted as he filled her asshole with hot, white cum. He pumped into her bottom until he was completely drained, then he collapsed alongside her.

She laid face down while catching her breath and regaining her wits. Her thighs were sprawled on the bed. Derek laid beside her, still marveling at her beautiful bottom.

"What do you think?" he asked, caressing her lower back.

She exhaled deeply, still blindfolded. "I think I've found a new pleasure spot. And you? What do you think about all this?"

He stroked her butt. "Best room service I've ever had."

About 20 minutes later, Sophia was in her uniform again, tidied up after fixing herself in Derek's bathroom. There was a glow on her face and she walked with perfect posture as she took the service cart back to the bottom floor. She had succeeded in hiding the fact that her asshole was sore. If no one was around, she'd certainly be walking with a limp.

When she saw Christine, the room service girl who was supposed to get her ass fucked by Derek, she gave her a small smile. The 'real' room service girl had no idea what she had just missed.

After finishing a few other errands, Sophia needed a quick bathroom break. She still felt Derek's cum leaking from her asshole and she didn't want her panties stained. This was her fault and inexperience for not cleaning herself thoroughly enough after her first anal fucking.

A fellow room service girl was in there washing her hands and checking her makeup in the mirror. They smiled at each other, said their hellos, and made brief small talk.

Before entering a stall, Sophia wetted a paper towel and brought it with her. She closed the stall door and laid a sheet on the toilet before sitting on it. When she heard the other room service girl leave, Sophia immediately went to work rubbing her clit. The aching and neediness had returned a while ago and had made doing her job difficult. She rubbed fast and hard while cum from her anus dripped into the toilet.

She thought of some of Derek's last words to her before she left his room.

Derek had told her: "Now if you'll excuse me, I'm an extremely busy man, even at this hour. And you have a duty to return to. Clean yourself, but not too much. Leave some of my cum in your asshole. It's sexier that way. If there's anything else I need tomorrow night, I'll request it from you personally."

He had planted a firm kiss on her butt before they cleaned themselves.

Sophia came again sitting on the toilet, her third time that night. Trickles of her fluids dripped into the water as she came, mixing with cum dripping from her spread anus. She used the wet paper towel to wipe the cum from her anus, this time for good, and she even pushed her finger inside her ass for maximum cleanliness (and a bit of pleasure too). With the clean side of the wet paper towel, she wiped her cum from her pussy.

She flushed the toilet when she finished, washed her hands, put a smile on her face, and went back to being the 'room service anal girl,' as Derek had so appropriately called her when she left his room earlier.

The End

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