Hotel Hook Up

So this is the first story I have written that is a request from someone who contacted me on here! They challenged me to write a messy, messed up dirty story involving a stranger hook up! I hope I achieved this! Please be aware this story contains some very strong themes and some very messy play. Please check out the tags at the end before reading if you don't like messy play! Anyway enjoy!

Twice a year her company sent her to a conference. Three days of corporate meetings, wining and dining and getting to know boring people all for the good of the company. The plus side was that it was three nights in a top rated hotel with all food paid for and swanky room with a big bed to stay in.

By the final night though Ruby had become thoroughly bored and like everyone else hit the bar for one last night of drinking. It was same usual routine twice a year listening to boring work talk. She was good at her job and always impressed at conferences but by the last night she needed a release. Every night most of the people at the conference had a drink or two at the bar but on the last night the majority let their hair down and have a big drinking session.

Some people still used this night as a way of old school networking or in the case of some macho bravado but Ruby saw the final night as something different. This was a night where she could use all of her charms and the occasion to indulge in a little fun. Her idea of a little fun wasn't the same as most peoples though. Sure lots of people at conferences hook up for a quick drunken fuck but Ruby always wanted more than that. She always wanted to indulge in her darkest desires.

A quick fuck was easy to find at these events but that never satisfied her urges. The middle management 50 plus married guys desperately lusting after her and trying to chat her up did nothing for her. She preferred to find her own man and picked her victims wisely.

She ordered a vodka and orange at the bar and scanned the room. It was starting to thin out about now as it was just gone 10pm. The only ones left in the bar were mostly the hardcore drinkers and those still hanging on for a last minute business deal. She spotted a well groomed man in his late thirties come up to the other end of the bar. She eyed him for awhile before deciding to go and speak to him.

"Good conference?" She asked him standing close to him to make him jump a little.

"Erm yes I guess." He nervously replied.

"It's always good to get to the last night and have a few drinks and unwind isn't it?" She said smiling at him.

"Erm yes it is. Do I know you?"

"No but I've seen you the last three days. I'm part of the PFS investment team." She smiled at him again.

"Ah yes I remember a very popular presentation." He replied smiling back at her.

"Is this your first conference?" She asked him.

"Yes it is. I'm new with my company, I work for..."

"Let's not talk about work!" She cut him off abruptly.

"It's the last night everyone can unwind and some of us can let out hair down. Come on let's get some more drinks."

Her confidence had shaken this man. He had no idea who she was and here she was ordering a bottle of champagne and glasses for the pair of them. She knew exactly what she was doing though. He had a nice body and kept himself neat and tidy and had a look about him that she could wrap him around her little finger. They made idle chat as they drank their way through the champagne bottle.

"This is my fifth year doing this conference, that's ten conferences in total! It gets awfully lonely spending three nights on your own in a hotel room don't you think?"

"Ermm yeh it does I guess." He replied wondering where this was leading to.

"Still it's nice to get to know new people isn't it. Especially after a few drinks."

She shifted in her chair showing more of her legs. She noticed him glance down a little longer at her legs. She moved one of her legs a little more so it just ever so briefly showing a bit of her lace stocking top. She knew he would look, they always did.

"So are you married?"

"No I'm single, what about you?" He replied desperately not trying to look at either her legs or cleavage.

"Single aswell...a coincidence eh!" She laughed. "It's good to keep some company isn't it."

She leaned in closer to him.

"I like to get to know new people." She whispered in his ear putting one hand on his thigh.

"What it is you want from me? Who are you?" He replied nervously.

"I want you. In my room. Don't worry I'm not a hooker, I'm not going to scam you!" She laughed.

"And I know you want me aswell, I've seen you looking at me cleavage and my legs. I bet you've been wondering if I'm wearing stockings aren't you?" She continued as she gave a quick look around and then let her dress slide up one leg a bit showing off the full stocking top and a bit of her bare thigh.

She had gone in for the kill, so brazen in her actions but she keep they would work. Her hand wander across his thigh to his crotch. He looked around nervously but no one was paying any attention as her hand glided over his trousers and felt his erection straining against the material.

"Everyone has fantasies you know. What are yours?" She purred into his ear.

"Ermm sorry what?" Was all he could nervously reply.

"Fantasies darling. Go on what would you like to do with me? Your cock tells me you want to do something with me!" She whispered in his ear squeezing his erection again.

"I want to fuck you." He finally blurted out.

"Is that all?!" She laughed, "Which hole do you want to fuck? All of them?"

"Yes all of them." He blushed.

"Even my tight arsehole?"

"Yes." Was his quiet reply.

"See I told you everyone had their fantasies! Come on let's go." She said quickly downing the last of her drink.

She grabbed him by the hand and led him from the bar to the lift. He was much taller and bigger than her but she led the way. He could easily have pushed her away or refused to go but already he was under her spell and thinking with his dick. The pair of them spilled into the lift and as the doors closed he went to kiss her.

"Ah not yet big boy!" She laughed.

"Non of that lovely dovey stuff." She continued.

She grabbed hold of his hand and shoved it up her skirt between her legs until his hot hand found her bare knickerless pussy.

"Here's what's going happening young Mr big shot. We are going to go to my room and fuck like animals ok. I like it hard and fast. I like it dirty and messy. You can back out when the lift doors open if you want but they way your cock is straining against those trousers tells me you want it that way?"

"Yes I want to fuck you hard so much." He replied rubbing his fingers against her wet pussy.

Suddenly the lift stop and then doors opened. She laughed as they fell out onto the corridor. She went dragged him over to her hotel room door and kissed him passionately. He finally grabbed hold of her and kissed her back until she pulled her head away giggling.

"I hope you are going to be more forceful than that when we get inside!" She teased.

She opened her room door and led him inside. No going back for either of them now although she knew what she wanted from him anyway.

"Cigarette?" She asked.

"Ermm no I don't smoke sorry. I didn't think you could smoke inside hotel rooms now?" He replied nervously.

"I'm not going to smoke it in here I'm going to smoke it on the balcony whilst you fuck me." She announced confidently as if it was an everyday occurrence.

"What? What if someone sees us?"

"Oh come on you do want to fuck me don't you?" She said exasperated.

"I mean you told me in the bar you were up for some kinky fun, you told me you could handle me, you fingered my pussy in the lift and I felt your cock, it was impressive and I want you to fuck me with it. And the fact that someone might see us fuck on the balcony is thrilling isn't it. So you can either fuck me or fuck off for a lonely wank back in your room and I'll find someone else to fuck with me tonight. So what's it to be? Either the best kinkiest night of your life or the door is there."

Her rant over she opened the doors to the balcony walked through to the railing and bent over lifting up her skirt revealing her bare arse and stocking tops. He finally followed, her rant had worked, he knew he wouldn't get a chance like this again as he looked at her bent over her red hair shining in the night lights.

"Here's what's gonna happen boy. You are going to fuck me whilst I smoke this cigarette. Go as hard as you like. I will feel so tight around your cock but I love it forced in me. But don't cum. If you cum then it's night over for you. Just think of this as a little warm up!"

She sparked up her cigarette and blew smoke out into the night sky.

"Come on let's do this." She said bending over a bit more.

She heard from undo his trousers and drop them to his ankles and position himself behind her. She smiled to herself as she took another drag on her cigarette, she had him now. There was no going back for him now he was going to be there all night now to fulfil her dirty sordid fantasies.

She giggled as his hands found her waist then moaned as she felt his rock hard hot cock at the entrance to her pussy. Suddenly he pushed into her pussy. It stretched and hurt her because of the size but she loved it. She knew she had chosen well cock size now she just hoped she had chosen well in terms of how kinky he could be.

She gasped as he started fucking her from behind. She knew he had been wanting to fuck her from the moment he had seen her and now she wanted to see if he could control himself enough not to cum. He grabbed hold of her boobs from behind through her dress as he started to get into a rhythm fucking her.

"Do you like my boobs?" She asked before taking another drag on her cigarette. "They cost me a fortune to get enhanced, good job I got a bonus that year!"

She moaned as he slammed in hard to her now. He was really getting into this now and she had this feeling that now she could get him to do whatever she wanted for the rest of the night.

"Remember not too cum. I've still got half my cigarette left!" She gasped as she held onto the balcony railings.

He grunted as he fucked her trying to last as long as possible. He had never met anyone quite like her before and probably would never meet anyone like her again. His cock pistoned in and out of her hard and fast. He couldn't believe how brazen she was and how she had got him doing this. It made him angry yet at the same time so turned on.

"Stop!"

Her word snapped him out of his thoughts as he slowed his fucking down.

"I've finished my cigarette." She announced as she flicked it away into the night sky. "You can pull out now and go inside, the fun shall begin now!"

He pulled out and quickly shot inside grabbing his underwear and trousers and sat on the bed. He watched her turn around. She looked and smiled straight at him as she slid the dress off her shoulders and down, her magnificent breasts falling out into the cool night air. She eased the dress with one full movement past her hips and let it fall to the floor. She elegantly stepped out of it and walked across her balcony back into the hotel room wearing nothing but her heels and hold up stockings.

"Do you want me to close the balcony door and curtains in case someone sees or hears us?" She laughed.

"Cos you know I find it a little more exciting that someone might be watching us don't you?"

He didn't reply, he just sat there with his erect cock giving away his true feelings.

"I guess if you didn't want a cigarette you won't want any of this?" She said to him going to the small dresser table. She reached into her bag and pulled out a small bag of white powder.

"What is it?" He quietly asked.

"It's cocaine." She replied carefully lining it up on the dresser. "You must have seen it before, don't act all innocent with me!"

"Well yes but not for me sorry."

"There's no need to apologise! All the more for me! It will make the night go with more of a bang and last longer!" She laughed as she bent down and snorted the line up her nose. A little bit was left on the dresser which she scooped up with her little finger and rubbed into her gums.

"So big boy I'm ready for the fun to really begin now!" She said walking straight up to him and kneeling down in front of him. "You must be really pissed off at me right now? You thought I was going to take you up to my room and let you fuck me and you would be in charge. But Mr Middle Management I'm in charge really! But you can still do anything you want with me! Go on be daring!"

He still stayed silent, almost hypnotized by what was happening to him. She took hold of his cock and held it up and ran her tongue over his balls making him moan. She licked all the way up to the head of his cock and swirled her tongue teasingly around the head. She dipped her head down taking his cock in her mouth and sucking hard and deep. The mixture of the hit of cocaine and how horny she was feeling was fuelling her adrenaline as the cock hit the back of her throat.

She pulled her mouth back up his hard cock and licked the head again and looked up at him lustfully.

"Fuck my mouth....you know you want to...don't hold back...please." She begged.

He looked down at her, this woman he had only met at the bar just over an hour ago was now on her knees nearly naked looking up at him lustfully wanting to be used. Finally he stood up and pushed his cock against her lips and back into her mouth. She moaned as his hard cock slipped back in her mouth. This was followed by a squeal of delight as he grabbed hold of her hair. Finally he had got the idea!

He started to fuck her throat with his cock shoving it in and out building up his pace. Her pussy got wetter the more he pushed harder into her throat. She loved a cock deep in her throat and craved a good face fucking. She pushed her head forward to get him to push his cock further down her throat. He pulled his cock out of her mouth leaving her gasping for air and drooling but with a big smile on her.

"More..make me gag I can take it." She said in a provoking manner.

He grabbed hold of her hair tightly and rammed his cock deep in her mouth. She gagged and spluttered and choked on it but it turned her on so much. Twice a year she could indulge herself like this and be perverted and push herself and whoever she was with. Her eyes watered as he pushed her head down on his cock, her mouth drooling around his cock. He pushed as far as he could and held her head in place. She breathed hard through her nose but still gagged. Her mouth filled with drool and bile around his cock and she spluttered hard as he released his cock partly from her mouth. She gasped and retched leaving a trail of spit and bile dripping from her mouth and his cock as he stood back.

"You nasty whore you was almost sick on my cock." He exclaimed.

"What did you call me?" She replied licking her lips.

"A nasty whore." He repeated.

"Ohhh fuck it turns me on to be called that!" She exclaimed as she one hand found her pussy and she started to rub her clit in front of him.

"I get even nastier than that honey! That's if you want to continue?! Remember I said I'd be the fuck of your life." She continued.

He just stood his erect cock bouncing obscenely.

"I know you want to get nasty with me, I can see it in your eyes. Now lay down on the bed."

He laid down without saying anything and she followed him on to the bed. She still had her heels on as they got caught in the end of the sheets but she didn't care, she just wanted more of his cock. She grabbed hold of his cock again and licked all around it cleaning off all the dirty spit and bile left on it. She worked down to his balls again and sucked hard on them making him squirm and moan.

She pushed his thighs further apart and ran her tongue down to his bumhole. He moaned and jumped at the sensation. She told him to lift his legs up to gain more access. She helped manoeuvre him and soon had his bumhole staring up at her. She dived in again and licked around it before pushing her tongue in deep. He groaned in delight as she tasted his dark hole. It turned her on to taste this dark, sweaty, dirty forbidden area and it excited her that he was enjoying it.

She pulled her tongue away and trailed a finger around his bumhole, her red painted long nail teasing such a sensitive area. Slowly she reached his dark opening and pushed her finger gently inside. He moaned and attempted to move but she hushed him.

"Just relax and enjoy!"

She eased her finger gently in and out of his tight hole. Her other hand took hold of his erect cock and started to wank it in time with the movement of the finger in his arse. He moaned louder as she probed her finger deeper into his tight hole. She slowly pulled it back to just the finger nail and placed a second finger at the entrance. Slowly she eased a second finger gently in but still making him cry out.

"Shhhh I won't hurt you just stretch you and find your prostrate. Remember not too cum! Let me know if you are getting close!"

She worked both fingers deeper into his arse stretching him wider and finding his prostrate. She pushed gently on it making him groan and tremble with an intense feeling he had never had before. She leaned over his cock and took it back into her mouth sucking on it hard up and down as she finger fucked his tight arse. She pushed her fingers in and out quicker now and as deep as she could pushing on his prostrate making him jerk his cock up deeper into her mouth.

"Stop! Too much!" He cried out desperately not trying to shoot his load in her mouth.

She took her mouth off his cock and slowly slid her fingers out of his bum and knelt back smiling at him.

"Oh, look what mess you have left on my fingers." She laughed as she held up her fingers to show him they were covered in wet slimy brown streaks from his arse.

Without saying another word she stuck out her tongue and put her dirty fingers in her mouth and sucked them clean. His eyes widen and mouth dropped in shock as he watched her suck her fingers without even flinching or pulling a face.

"Your arse tastes amazing." She exclaimed once she took her now clean fingers out of her mouth.

"Are you sore after my fingering of you, want me to kiss it better?"

She bent down and returned to his arse and gently kissed around the now dirty opening. Yet again she slowly worked her tongue around and inside a little rimming him clean.

She came up for air smiling but her eyes full of lust and crawled over his body to his face. Without warning she placed her lips on his and started to give him a passionate kiss. She pulled back from her kiss and stroked his forehead.

"You really are a dirty bitch." He exclaimed.

"I'm just warming up darling." She whispered in his ear.

"Now do you want me to get nastier and make you cum?"

"Yes, yes please." He groaned as she nibbled his ear.

She moved down his body and straddled his waist placing her hot wet pussy over his hard cock. She gently eased his cock inside her pussy eliciting a groan from both of them. His cock slid easily into her as she moved her body slowly down taking all of his length inside of her. She ground down on him once she had him fully inside of her. Slowly she built up a rhythm riding him getting quicker until she was slamming down on his body.

She took hold of his hands and put them on her boobs so he could grope them while she rode his cock. She could tell by looking at his face he was ready to cum but she continued riding him hard and fast.

"Go on cum for me." She said breathlessly bouncing on his cock.

A wicked smile came across her face as he groaned out loudly and jerked his body up to meet her thrusts down on his cock. His cock twitched and his pent up orgasm finally came as his cock shot his hot cum deep inside of her. She screamed in pleasure as she felt him fill her pussy with his big load of cum. This was the sign for her to release aswell but not the release of her impending orgasm but her bladder. She started to pee on him as she rode his cock, her hot piss running down his cock as it jerked it's cum inside her.