Group Sex The Tales of Andrea & Dean

Anyone for Cocktails?

The orange glow of the waning day faded from the rows of houses outside Andrea's bedroom window like the dying embers of a fire. Like so many times before, she stood at her floor-to-ceiling window, naked, peering out at Dean's house. Normally she would be showing off for him, teasing him, modelling her slim, toned body for him and any other curious neighbours within eyesight; but tonight she knew he was not home.

She had just come from her bathroom, her hair blow-dried and styled, her long, silky blonde locks pinned so that they fell over her right shoulder, a few loose strands framing her pretty, oval face. She gently touched her freshly shaved pussy lips, so soft and smooth, goosebumps breaking out on her thighs and arms. She felt the heat rise in her cheeks, and a tingling sensation between her legs.

Since the events of the previous week, Andrea had been in an almost constant state of arousal. Every time she let her mind wander, she recalled the dirty, thrilling words she had uttered whilst on her knees in her neighbour's office, his hard cock resting heavily across her pretty face:

"Dean, I, your neighbour Andrea, promise to be your slutty little fuck toy, and to suck and fuck this big dick whenever and wherever you want me to."

Even now, softly reciting the words to herself, which she had long since memorised, she felt a bolt of excitement rip through her body. Without even realising it, she had slipped her middle finger between her soft labia, and was slowly stroking her hard clit.

When she had arrived home that day-the day she sucked off one of Dean's potential clients until the uptight, middle-aged man had blasted his semen into her willing mouth-she had found the video he had taken waiting for her in her email inbox. She recalled nervously opening the attachment with trembling fingers, watching herself promise to be Dean's fuck toy, to do whatever he wished with her, whenever he desired, watching herself take his huge, beautiful cock all the way down her throat as she maintained eye contact with the camera, watching herself jerk his spurting cock all over her face, coating it in thick ropes of warm semen, watching Natalie lick his cum off her face, sharing it with her in long, passionate, sloppy cum-kisses.

"I want to be your good little slut that you can play with whenever you are in the mood. I will do whatever you ask and let you use me for your pleasure as long as you wish," she whispered, staring out at Dean's bedroom window, her finger rubbing her clit faster now, her other hand sliding up her firm, flat stomach to caress her perky tits.

Andrea could hardly believe how far she had come. From being a shy, unassuming girl-next-door, to committing herself to being Dean's cum slut, to use as he saw fit. She was his slut. A filthy, naughty, submissive whore, ready to do whatever Dean wished of her, no matter how depraved. A moan escaped her lips as her wetness dripped onto her thighs.

She was abruptly brought back into the present, jerking her hand away from her soaking cunt, her finger glistening with her juices. She slipped it between her lips and moaned as she tasted herself. She didn't want to spoil this night for Dean, or herself. She wanted to be horny, and excited, and ready and willing to do whatever he may ask of her. She ached to masturbate, but Dean had specifically asked her to refrain from doing so for the past three days. It was driving her crazy.

Turning away from the window, she made her way to her wardrobe and selected her clothes for the evening, quickly dressing, applying her red lipstick, and making her way downstairs. She heard the taxi's horn outside her house and had one last look in the hallway mirror. She was proud of how sexy she looked, and was sure Dean would agree.

Dean had asked Andrea to meet him at a bar near his office building. She considered it a miracle that she made it there at all, as the cab driver's eyes were mostly looking in his rear view mirror instead of the road. The driver had actually adjusted his mirror so he would have a perfect view of Andrea in the back seat. Arriving at her destination, she thanked and paid him, stepping out of the cab and feeling his eyes on her perfect ass. She smiled to herself, knowing that her outfit certainly passed the test.

She entered the bar and made her way to the second floor, where a hostess greeted her.

"Hello, my name's Andrea, I'm here for the private party. It should be under the name 'Dean'," said Andrea, holding her handbag in front of her.

"Oh yes, you're serving them tonight, right?" replied the young, dark-haired hostess, eyeing Andrea from head to toe. "He specifically requested that he have his own server. I've got no problems with it. Makes my job easier," she continued, giggling.

"Yes, he's a very particular man," Andrea replied.

"And a handsome one too. Almost makes me wish I was serving them after all," said the hostess, winking. "I'm Kelly, by the way. Here, let me take your handbag and show you where to pick up the drinks."

The hostess led her through a curtain and down a narrow hallway to an opening in the wall that looked out behind a bar.

"You can place and pick up your orders from here. That doorway just a few steps down the hall goes into the private function room. I'll help you out in any way I can," Kelly said, glancing at her watch. "They should be ready for you now."

"Thanks," replied Andrea, smiling warmly.

Kelly looked her up and down again, smiling mischievously.

"Mmm, they are going to absolutely love you, honey," she said.

"I certainly hope so," replied Andrea, running her hands down her hips. Her palms had already begun to sweat.

Andrea made her way down the hall, and turned left through a dark doorway. She could already hear the sounds of several men's voices over the ambient house music, and her heart was beating like a jackhammer in her chest. She took a deep breath, then stepped between the curtains, which were tied back with sashes on either side.

The room was dimly lit, with old-fashioned yellowish lamps gilding the walls. It was decorated like a Victorian trophy room, with taxidermy deer heads, paintings depicting landscapes and tall ships at sea, leather-bound books in tall bookcases, wing-backed studded leather chairs and chesterfields, and mahogany tables and desks.

The moment Andrea entered, all conversation stopped, and five pairs of hungry male eyes turned her way. She was dressed in a skin-tight, black, strapless dress. It was simple, unadorned, with thin strips of fabric criss-crossed on the back, and left very little to the imagination. Her modest tits looked perky and round, and despite the lacy, strapless bra she wore, her nipples hardened, poking through the thin fabric of her dress as she looked at the men in front of her. The dress was scandalously short, barely covering her perfect ass, and her outfit was completed by a pair of black six inch heels.

She put her hands behind her back, pushing her titties out and flashed her cutest smile to the men.

"Hi gentlemen! I'm Andrea, and I'll be your server for the evening," she said cheerily.

Her eyes found Dean. He was sitting comfortably on one of the leather couches, his foot across his knee clad in handsome brown wingtips. He was dressed in a well-fitting navy suit with a blue and white checked shirt, no tie, since this was a more casual event.

Andrea's heart fluttered as Dean looked her sultry form up and down, his gaze finally settling at her eyes. Her heart fluttered as she noted the faint upturned curl at the corner of his mouth. Despite her apprehension about the evening, she knew, looking into his commanding hazel eyes, that she was ready to do anything for him. Her recorded promise was no less true now than it was when she made it: she was his slut.

Finally managing to tear her eyes away from Dean, Andrea looked about the room at the other gentlemen he had brought with him. She didn't recognise any of them, and he had told her specifically that she was not to let on that she and Dean knew each other.

Dean stood up and approached her, extending his hand.

"Hello Andrea. Pleasure to meet you. I'm Dean," he said, dropping a barely-perceptible wink.

He closed his warm fingers around her small hand, then lifted it to his lips, kissing it softly. She suppressed a shudder and felt her pussy moisten.

"Let me introduce you to my colleagues. This is our executive director Steven, board members Adam and Brian, and our CFO Derek," Dean spoke, introducing them each in turn.

Steven was the eldest, probably in his late fifties or early sixties, with white hair and carrying a little extra weight under his austere black suit. Adam was likely in his mid-forties, short and stocky, but solidly built, with short blonde hair and a striped shirt with the sleeves rolled up. Brian looked younger, maybe late thirties, a tall, lean black man dressed in a black shirt and grey blazer. Derek seemed to be around Adam's age, a slender man with slicked-back hair and glasses, wearing a slightly ill-fitting suit. Andrea wasn't surprised to learn that this somewhat nerdy-looking man ran the numbers for the company Dean worked for.

They each waved and greeted Andrea, and she enjoyed the way each of them looked at her lustfully. She felt a tremble run through her body as the thought of being with these men, these strangers, filled her with a nervous excitement. She had never been with multiple men before. The closest she had come was when Jay fucked her as Dean watched and jerked off. Am I really going to go through with this? she thought, biting her lower lip. She looked back to Dean, whose hungry stare was answer enough.

"Can I get you gentlemen something to drink?" she offered, her voice high and wavering.

The men gave her their orders and she turned around, walking slowly out of the room, swaying her hips, letting them drink in the sight of her perfect buttocks in her skin-tight dress.

She reached the order window and breathed heavily. Her head was swimming a little, and she felt overwhelmed. Surely Dean would understand if she backed out now. She would simply pull him aside and tell him she couldn't go through with it. She could promise to let him take her home and fuck her brains out all night, but she couldn't let Dean and four strange men gang bang her in a bar.

Her body trembled again as the thought of all those hands, and eyes, and mouths on her body, groping her, kissing her, stripping her. She felt a pang of pleasure in her pussy, and an increasing wetness between her labia. She couldn't believe she was getting aroused by these filthy thoughts.

"Am I really that much of a slut?" she said quietly to herself, looking down and resting her hands against the small counter top along the bottom edge of the window.

"Um... you ok, hun?" said a voice.

Andrea's head snapped up to look at Kelly standing on the other side of the window, trying to conceal a smirk.

"Oh! Yeah...sorry, I'm fine," Andrea stammered, blushing deeply.

Kelly gave her a warm, sympathetic smile. Behind it though, Andrea thought she could sense a subtle green tinge of envy.

"Here, this will take the edge off," said Kelly, turning around and retrieving a bottle from the shelf behind her.

She poured two shots of the clear spirit and gave one to Andrea, holding the other up.

"To us sluts," Kelly said.

"To us," replied Andrea, a little embarrassed by the toast, but thankful for Kelly's support.

The shot burned pleasantly as it went down-a flavoured vodka, Andrea guessed, apple-and before she knew it, Kelly had poured a second. The girls drank again, and Andrea felt the warmth spread through her body, making her feel more at ease.

"Thanks," she said, her cheeks flushing.

"No worries, hun. Now let me take your order. Don't want to keep those thirsty men waiting too long, do we?" she said, winking.

Andrea ordered the drinks, and Kelly returned with a tray, smiling at Andrea with a naughty smirk. Andrea took the tray and returned to the private room, handing out the men's drinks as they talked among themselves.

The next while went by without incident, the men enjoying their drinks, talking business, sport, family life. They were polite and courteous to Andrea, even if their ravenous gazes told her the true, sexual desire in their hearts. Dean played along well, never giving any indication that the two of them had previous history.

After the men grew more comfortable (and a little drunk), Adam asked Andrea to stay and chat with them.

"Are you sure? You don't want more drinks?" she said, holding the tray behind her back and pushing her perky tits out.

"The drinks can wait. We would love some company," said Brian in his deep, soothing voice.

Dean was sitting on a couch next to Derek, and the men separated so that she could sit between them. She lowered herself onto the couch, her dress riding up as she crossed her legs.

"So, what's this evening all about?" she asked.

"We're celebrating Dean's success with a client we've been chasing for some time now. Somehow this slick bastard managed to convince them to sign a contract with us," said Steven, taking a sip of his scotch and soda.

"Seriously. This guy, Mr. Callahan... he's never agreed to work with us before, even though we've pitched to him so many times. Dean's a bit of a celebrity for securing that contract," added Brian.

"Oh, congratulations, Dean!" said Andrea in a cheerful voice.

Without thinking, she leaned over and kissed his cheek, then giggled.

"Thanks Andrea. No offense to these guys, but I'll take your kiss as a reward over free drinks any day," he laughed.

The other men joined him, probably all wishing it had been their cheek she had kissed.

The men gathered around her making conversation, staring at her long, toned legs, pert ass, and the soft swells of her breasts. She found herself loving the attention, and could have sworn the temperature in the room had gone up a few degrees.

"So Andrea, is there a lucky man in your life?" Adam asked, looking at her thighs instead of her face.

"Um... kinda," she said hesitantly, flicking a glance at Dean.

"So, you have a boyfriend?" said Derek, who had remained relatively quiet to that point. He was the only one, aside from Dean, who wasn't wearing a wedding band.

""Kinda" doesn't sound too convincing, sweetheart," said Steven, leering at her tits.

"Well, we have an... interesting relationship," she said enigmatically, then giggled.

"Oh? And what's interesting about it?" asked Brian.

"We're not exactly exclusive, I guess you could say," she replied, stealing another look at Dean, who remained impassive.

"How do you think he'd feel about you wearing a sexy little dress, serving drinks to five older men in a private room all by yourself?" Adam said.

"I think he'd wonder what naughty things these five men were planning to do with me," she said, giggling again.

There was a shocked silence, then she stood up quickly, taking a step forward to retrieve her tray from the coffee table, bending slowly at the waist to let the men have a glorious look at her behind. Her dress had crept up so that the bottoms of her ass cheeks were visible. She looked over her shoulder and pushed it down a little, smiling at the horny, open-mouthed men.

"More drinks?" she asked innocently.

She served them again, this time taking breaks in between orders to chat with them. It was Adam who touched her first. She was talking to Adam and Brian near the small unattended bar in the room when she felt Adam rest his hand on the small of her back. As they continued talking, he slid it lower, cupping her luscious ass.

Her heart raced as Adam squeezed her ass. Brian smiled knowingly down at her and soon his hand was groping her other buttock. She was a little surprised that the married men were the first to make a move on her, but she wasn't complaining.

She flirted with them for a little while, then moved over to sit next to Steven. The old man shuffled right next to her and immediately put his hand on her thigh, smiling lasciviously at her. Even Derek, who was the most reserved of the group, had 'accidentally' bumped his groin against her ass when she was picking up a glass from a table.

It was obvious the men were becoming more and more bold as they drank. Soon, any time she was near one of them they had a hand on her, squeezing her ass, stroking her thigh, holding her waist. No one had made a move to fondle her breasts yet, but the way things were going she was sure it wasn't far off.

Andrea, for her part, was doing her best to tease the men, bending over to pick up glasses, crossing and uncrossing her legs to flash her lacy black panties, swaying her hips and wiggling her ass, and sticking her tits out proudly, her dress creeping down dangerously low-showing the lacy edges of her bra.

After she had finished serving the latest round of drinks, Dean got Andrea's attention with a wave of his hand.

"Andrea, sweetie, you're doing such a good job for us tonight. And don't worry, I'm sure you'll get a handsome tip at the end of the evening, but I was wondering if you'd be interested in... upping your earnings, a little," he said with a mischievous grin.

"Oh. Um... maybe. What did you have in mind, sir?" she said in an innocent tone, though her heart skipped a beat, wondering what he was planning.

"Mmmm, 'sir'... I like that," murmured Steven.

Dean chuckled and reached into his suit jacket, taking out a twenty and placing it in her hand.

"Go have a drink on our tab, and when you come back, I want you be carrying your drink in one hand, and your bra in the other."

Andrea felt her cheeks flush, but her pussy tingled. She nodded.

"Yes, sir," she said, then made her exit.

"A new order already? They must be smashed," Kelly said to her when she returned to the bar.

"No... just a vodka cranberry for me. They insisted. They also had another request," Andrea replied.

She turned away from Kelly and pulled the top of her dress down, then reached back and unfastened her bra, removing it and pulling her dress back up, adjusting it across her firm, perky breasts. She turned back around, still blushing.

"How do I look?" she asked.

Kelly looked at her boobs and bit her lower lip. "They're going to love it."

She mixed Andrea's drink and gave it to her, admiring her tits once again before Andrea turned to return to what was beginning to feel like a lion's den. She entered the room with a spring in her step, making sure her titties bounced in her dress. Her nipples felt like little pebbles as she looked around at the men who were fixated on her jiggling tits and protruding nipples. She bent over in front of Dean and placed her bra on the coffee table, then pushed her tits out for the men to ogle.

"It this better, sir?" she asked proudly.

"Much better," Dean said, and she noticed a bulge forming in his snug suit pants.

She sat on a chair and chatted with the men, who were now all focused on her. The attention flattered her, and she knew she was soaking her panties as five pairs of eyes admired her. Before long, another one of the men was reaching for his wallet. It was Adam.

"Interested in another tip?" he asked, waving another twenty in the air.

"Hmmm, sure!" said Andrea. "What do you want me to do?"

Adam leaned forward and placed the twenty against her chest, then using his fingers, slid it down, tucking it into the top of her dress between her breasts, until only a small portion of the note was visible.

"Without touching it with your hands, I want you to make that note fall to the table. Then it's all yours," he gave her a self-satisfied grin, clearly proud of his creativity.

Andrea stood up and giggled, putting her hands on her hips and looking down at the note stuffed into her dress. She looked around at the men, then back to the note. The solution was obvious, of course, but Andrea decided to have a little fun with it.

First, she dipped her head, trying to reach the note with her mouth, pushing her chest out and opening her mouth, trying to grasp it with her lips. Then men laughed at her futile attempts. She gave them a sarcastic frown, then ran her hands up her body to cup her breasts. She leaned over and began pushing her tits up and wiggling her torso, attempting to work the note loose from her dress. It crinkled between her breasts as she pushed them together, but rather than being extracted, it only worked its way deeper into her dress.

The men laughed and encouraged her, clapping and slapping their knees gleefully.

"Gosh, that's just made it worse," pouted Andrea, standing straight again, still cupping her tits, pushing them up to create delicious cleavage.

"Looks like your options are limited, baby girl," said Brian, an obvious bulge in the crotch of his dark jeans.

Andrea sighed and pouted again. "I guess so. Only one thing left to try," she said sweetly.

She slid her fingers across the top of her dress and pinched the fabric on either side of her breasts. She looked up and bit her lower lip, eyeing the men as she felt her pussy tingle again. She had their rapt attention as she slowly began pulling the top of her dress down over her tits. She did it slowly, diligently, exposing centimetre after centimetre of her milky bust, until the tops of her areolae were visible. Her cute nipples popped into view as she pulled her dress down across them. They hardened instantly in the open air of the room, and the men watched, mesmerised as she pulled the dress lower.

When the dress reached just below the sensuous bottom curves of her perky tits, the note fell free, drifting gracefully to the table and settling next to Andrea's discarded bra. Not one of the men were watching the note as it fell. They erupted in a chorus of cheers as Andrea proudly displayed her firm, round tits to the guests, capped by her small, hard, pink nipples, smiling widely as her cheeks and pussy burned.

"Yaay!" Andrea squeaked, jumping up and down, her arms akimbo in a celebratory gesture.

She set her perky tits in motion, bouncing and jiggling them with every little jump. The men cheered again, watching her tits bounce. Andrea looked around, seeing that now every single spectator was sporting a bulge in their pants. It turned her on to know that she had inspired these erections.

She bent over and retrieved the note, then began to lift the top of her dress back up.

"No no no, honey," Steven interjected, wagging his chubby finger at her. "You'll leave that dress just where it is."

He reached into his suit jacket and produced a fifty, standing up and slipping it down her top. She slipped the twenty in with it and giggled.

"Looks like you boys are going to have a topless server now," she said.

The truth was, at that moment she would have stripped totally naked for them had someone asked, tip or no tip.

Steven was staring at her perky tits, and his hand began to reach up to touch one as he licked his lips. Before he could make contact, Andrea moved away, picked up her drink, finishing the contents, then took another drink order and left the room.

She returned to the window and waited for Kelly to approach. She looked down at her exposed tits, feeling a mixture of shame and excitement. Here she was, serving drinks topless to a bunch of horny men. She already felt like such a slut, but she wanted more. She was so aroused she could barely keep her hand steady as she brushed a strand of hair away from her face.

When Kelly arrived, her eyes widened and she covered her mouth.

"Oh my god! Andrea! They've already got you to take your tits out?" she exclaimed, eyeing Andrea's round breasts.

Andrea shrugged, as if to say 'what can you do?' and ordered the next round. Kelly mixed the drinks and loaded the tray, then stared at Andrea's boobs and slowly shook her head.

"Honey, they are going to eat you up," she mused, leaning on the bar and putting her hand on her chin, her eyes looking at Andrea longingly.

"I certainly hope so," Andrea giggled.

For a brief moment, Andrea considered asking Kelly if she wanted to join her; to help service these horny men. However, after thinking about it, she changed her mind. She wanted these men all to herself. She wanted to be their fuck toy for the evening, and she didn't want any competition. Five men are going to use me like a filthy slut, she thought to herself, and her knees became weak. No-this was something she wanted to do on her own. She gave Kelly another saucy grin, then turned and left with the tray.

Entering the room again, Andrea saw the men all talking excitedly among themselves. She set the drinks on the table, getting ready to distribute them, but a hand grabbed her arm and pulled her down to sit on Derek's lap. She let out a squeak as she plopped down onto him, her tits jiggling. She could feel something long and hard against her ass. Derek may not have been a very bulky man, but he was certainly packing where it counted, she thought.

"Derek's been far too quiet tonight," said Steven, pushing another note down Andrea's dress. "Maybe you can loosen his tongue."

Andrea smiled and put her arm around Derek's neck, brushing her hard nipple against his cheek.

"What do you say, Derek. Would you like to use your tongue on me?" she asked him.

His eyes widened as he stared at her tits, then slowly nodded. He brought his mouth to her breasts, kissing it softly. Andrea sighed and felt a shiver as goosebumps broke out on her chest. Derek took her nipple between his lips and began sucking it. A soft moan escaped Andrea's lips, and she watched Brian stuff another note down her top. Brian's hand then dropped to her thigh, sliding up the inside of it. She caressed Derek's head as he suckled her tit, and parted her legs so that Brian could reach higher. He pushed her dress up her thighs until his fingers brushed her panties.

"Ooohhh..." she moaned.

"Wow... this slut has soaked her panties," noted Brian.

Andrea felt a rush through her body, hearing her called a dirty name, but she knew it was the truth. She was a slut. She began slowly grinding her ass against Derek's hard manhood. Another hand slid up her stomach and stuffed a note into her dress. Adam moved in and ravenously sucked her other tit into his mouth as he cupped it and squeezed it. Dean and Steven watched on with interest, sipping their drinks and waiting their turn.

Unable to help herself, Andrea reached down into the laps of the men sitting next to her and began to massage the large bulges in their pants. She actually gasped as she felt Brian's hard length in the leg of his jeans.

"Fuck," she sighed.

"You like big cocks, baby girl?" he asked.

"Yes sir. I love big, thick cocks," she moaned, hardly able to believe she had said it.

The men laughed as Andrea bit her lip, the stimulation of the hands and mouths on her body bringing her close to orgasm. After a minute, Steven reached into his wallet again.

"Ok sweetie, let's not forget why we're here. Let's treat the guest of honour. Stand up and strip those panties off for Dean," he said, stuffing yet another twenty down her dress.

Dean was sitting in a chair next to the couch-the perfect chair for a strip tease. Reluctantly, she pushed the hungry men away from her tits and stood up, saliva glistening on her hard nipples. She stood in front of Dean, then turned around. She swayed to the music, putting her hands on her head and dancing for him. She lost herself in the moment, feeling the buzz from the alcohol, the warmth of the room, the rhythmic music, and the attention of five horny men. She danced and swayed, shaking her ass in his face, then lowering it to his lap.

Andrea rubbed her perfect ass against Dean's member, feeling its impressive length and thickness through his suit pants. It occurred to her that he might even give Brian a run for his money in the size department. Dean groaned and she felt his hands on her ass, caressing it as she ground against his cock.

"Take them off!" cheered the men as they watched her erotic dance.

She giggled and stood between Dean's legs, bending at the waist and pulling her dress up over her hips. She looked between her legs as she hooked her thumbs in the waistband of her tiny thong, peeling it slowly over the luscious cheeks of her perfectly toned buttocks. She felt the air caress her puckered butthole and her moist pussy lips, causing her to shiver. She let the panties fall to the floor, then picked them up with her foot, turning around and dropping them onto Dean's lap. Dean instantly picked them up and sniffed them.

"Wow, they really are soaked. I think this little slut is getting hot for us," said Dean, inhaling her musky scent.

Andrea thought she would lose her mind if she didn't have a cock in her mouth or pussy soon. Her whole body buzzed with arousal, and her eyes roamed hungrily over Dean's lean body. Facing him, she bent over and began to unbutton his shirt, running her nails over his firm chest and toned abs, then began to undo his belt.

"Look at this slut. She's so desperate for cock right now, we don't even have to tip her to get her to do stuff," commented Adam, slurring slightly as he watched Andrea open Dean's trousers.

Andrea gave Adam a saucy grin, knowing it wasn't money that was serving as her motivation to do whatever these men wanted to her, but her commitment to Dean to be his dirty plaything. And she was far too aroused to stop now. In fact, she was surprised she even considered backing out.

She fished her hand into Dean's boxers and pulled out his massive cock, gasping despite the fact that she's seen it many times before.

"You like big cocks, hmm? Well now you've got one!" laughed Brian.​