by Jessie Dame
They had sat talking for over an hour outside Emma’s house until Jenny’s curtain twitching had become too much and Emma had to go inside to tell her all about her date. They were meeting up tomorrow to attend a charity ball run by their company. He was out of town on business today, so Emma had booked a half day off work to go meet Chad before he left Seattle.
Work dragged by and Emma squirmed in her seat all day with excitement. Finally, 1pm arrived and she made her way to Chad’s hotel. Knocking on his door, she was surprised when another man answered.
“Oh, sorry, I must have the wrong room,” she said, turning to go.
“No this is Chad’s room. I’m Roberto, his business partner. Please come in.” Roberto stood back to let Emma in and her heart sank. She had been so looking forward to her last meeting with Chad, now it looked like he was too busy with work.
Inside, Chad was sitting on the bed in his suit pants and shirt with no tie, taking off his watch.
“Ah, Emma at last,” he said, standing up and kissing her cheek. “I see you have met our partner for the afternoon."
Emma glanced at Roberto confused. He was short, maybe an inch taller than Emma and tanned with dark hair and dark eyes. What did Chad mean “our partner”?
Roberto walked over to her and kissed her softly on the lips. “No need to worry beautiful,” he said, taking her hand and walking her to the bed. “Chad has asked me to join you, for your pleasure only.”
Emma looked to Chad for an explanation as Roberto sat down beside her on the bed and began stroking her back with his thumb.
“Today Emma, you are going to tell us exactly what you would like us to do to you. Indulge your fantasies, anything you want.”
Emma thought for a moment. “I want you both to fuck me,” she said thoughtfully.
“A hole for each of us?” Roberto asked.
“No, I’m saving that for someone,” Emma said, smiling, thinking of Max. “I want you both to fuck me, and then I want you both to come on my face.”
Chad and Roberto smiled at each and they began to undress. Roberto was already hard, Emma noticed. Quickly, she stripped off and the two men began to lick and kiss her body.
“Roberto, lick my pussy,” Emma demanded, and he began to do so with gusto. He lapped at her wet pussy with his tongue as Chad watched and stroked his penis.
“Chad, in my mouth,” Emma ordered her friend and he straddled her chest and placed his cock in her mouth.
Soon, Emma needed to be penetrated. “Who wants to fuck me first?” Emma asked.
Roberto didn’t need to be asked twice. Wiping her juices from his chin, he thrust his short fat cock into her dripping pussy and began to move in and out quickly.
“Slow down there buddy,” Emma teased. “Remember what I said about coming on my face,” she reminded him.
Roberto pulled out, taking a break, and Chad flipped Emma on her knees and entered her from behind.
Emma moaned as his long cock pressed places Roberto’s hadn’t. Roberto was in front of her now, holding his throbbing penis in front of her face. Emma opened her mouth and he put it in. She could taste herself on his dick and as Chad fucked her and she sucked her own juices off Roberto’s dick, she came, hard.
When he was sure she had finished. Chad joined Roberto at her face and the two of them rubbed their cocks on her face and in and out of her mouth. Emma felt her pussy throbbing once more and she began to play with her clit.
Suddenly, Roberto began to ejaculate little drops of hot cum into her mouth. Emma drank it down like nectar and Roberto squirted over her face, rivers of cum rolled over her lips and into her mouth. Emma licked her mouth with her tongue and Chad began to squirt his ejaculate all over her lips. She opened her mouth and he blew his load into it, the sight of her cum covered face making him moan. Emma felt herself come for the second time, her body quivered until finally, exhausted, she lay on the bed panting.
When she recovered, Emma hopped in the shower. By the time she came out, Roberto was gone and Chad was packing his suitcases. Emma leaned against the door frame watching him.
“Thanks for everything this week Chad,” Emma said.
“It was my pleasure,” Chad said, flashing her his devilish grin. “But seriously Emma, you are a very sexual woman, don’t be afraid to ask for what you want.”
“I won’t, not anymore,” she said and she kissed him on the cheek and walked out the door.
The Backdoor
The next evening, Emma got ready for the work party. Her stomach bubbled with the excitement of seeing Max that night.
Earlier that day, she visited the sex shop Jenny had recommended to her. She had arranged a special surprise for him. She found one of the diamond butt plugs that Viv had been wearing. It was now inserted in her ass, ready for Max to find later on.
Emma slipped her feet into her silver stilettos and studied herself in the mirror. Gone was the mousey brown and black that she had worn for years. Tonight she wore a long red fitted dress with a slit right up to her hip. Her hair was in a loose chignon and her makeup was sultry. Her taxi beeped outside and she ran out of the house, eager to meet her date.
As Emma walked into the ballroom at the hotel, she felt all eyes turn to her. Most of the other women were in muted colors, nude, white, black. The old Emma would have been mortified to be the center of attention, but using her new-found confidence, she strutted right over to the bar where Max was waiting.
“Emma, wow,” he exclaimed, “just wow.”
“Thank you,” she said, calling the bartender over to order a drink. Suddenly, she felt an arm slip around her waist from the opposite side of Max. Confused, she looked up and saw Peter Harris, another co-worker from her floor. He had obviously been drinking for quite a while, his tux was already dishevelled and she could smell alcohol.
“Well, damn, Emma!” he slurred as he peered down the neckline of her dress into her cleavage.
Emma felt Max stiffen beside her, his face was hard and he was staring at Peter.
Slipping out from under Peter’s arm, she picked up her drink from the bar and turned to leave. “Thank you, Peter,” she said evenly, “your tie is crooked, by the way.”
Emma walked off with Max close behind her. He was still shooting daggers at Peter.
“Don’t worry about it,” Emma said with a wave of her hand, “everyone knows he’s a jerk.”
They joined some of their co-workers at a table where they drank and laughed together, unable to keep their eyes off each other. As the band began to play, couples made their way out onto the dance floor.
“Would you like to dance?” Max asked her, brushing a loose piece of hair from her face.
“Sure, just let me freshen up first.”
Emma left the ballroom to search for the bathroom. She was tipsy from both the alcohol and the feeling of having Max all to herself and she felt aroused by the feeling of fullness the butt plug gave her.
Emma reached a dead-end on the corridor she had been following and cursing, she turned back. Blocking her path, was a man, draining the last of his drink from his glass. Emma’s heart sank as she realized it was lecherous Peter Harris once again.
“I know a secret about you Emma,” Peter said in a silly singsong voice.
“Congratulations?” Emma said shortly, trying to brush past him, but he quickly caught her by the waist and pushed her up against the wall.
“Peter, take your fucking hands off me, right now,” Emma shouted.
“I couldn’t get into conference room B the other day, do you know why?” Peter continued, ignoring Emma’s protests. He grabbed both of Emma’s wrists and pinned them to her side and began to rub his erection against her crotch.
“Peter you have exactly five seconds to take your hands off me,” Emma warned him, struggling under his tight grip. Peter licked her neck, the sour smell of whiskey and cigarettes pervading her nostrils.
“I couldn’t get in, Emma, because you were fucking someone inside. Can it be my
turn with Emma the dirty office whore?”
Emma had enough, as Peter moved in to kiss her, she pulled back her head and cracked him as hard as she could in the nose. Peter staggered back just as Max rounded the corner. His eyes moved from Emma to Peter and as he realized what had happened, he lunged for the pathetic figure hunched on the floor cradling his bloody nose.
Emma jumped between them. “Let’s just go home Max,” she said, “he’s not worth it.”
Max looked like he was going to ignore Emma’s plea. After a moment of hesitation, he took her hand and led her down the corridor, his breathing coming fast and quick with temper. Outside, they jumped in a taxi and headed for his house. “I should have killed that guy,” he said.
“Max, I am well able to take care of myself,” Emma said firmly, then her expression softened and she whispered in his ear, “but you can take care of me when we get to yours”
An hour later in Max’s living room, they were relaxed drinking wine, when Max remembered his surprise.
“So what is it?” he asked eagerly, taking her glass of wine. Silently, Emma stood and pulled her dress up above her waist. She had gone commando and she turned her back to Max, bending over slightly, she heard him gasp.
“I told you the other night what I want you to do to me,” Emma said.
Max stood and unzipped his pants, his cock erect and slowly he put it in her pussy.
Emma had never felt so full before. As Max worked in and out of her pussy, he spread her ass cheeks and slowly pulled out the plug.
“Oh my god, Emma!” he whispered as he circled her gaping asshole with his finger.
Emma grabbed her purse off the table and handed him a tube of lube. “Fuck my asshole,” she told him looking into his eyes as she leaned forward on his sofa.
Without a word, Max lubricated his cock and slowly began to insert it into Emma.
She gasped at the sensation. It wasn’t painful, but she could feel her puckered hole stretching around his cock. The nerve endings were tingling and she began to play with her clit as he moved in and out a little further every time.
“Oh baby, I’m going to come soon,” Max groaned as he watched his cock move in and out of her virgin hole.
Emma wasn’t listening, her own orgasm was already breaking, the sensation of her full asshole making it stronger and deeper than any she had experienced with vaginal intercourse.
Max felt her tighten around his cock and began to pump harder as he came. When he was done, he watched in awe as he pulled his dripping cock out of her ass.
“Emma,” he said as he turned her around and kissed her long and hard. “Can… I keep you?” Emma smiled to herself as he got up off the couch.
She might just keep him too.
A Promising Future
Emma fixed the seam of her suspenders and checked herself out in the mirror in Max’s bathroom. Her tiny school girl skirt just covered her naked ass and her tight white shirt was tied up under her exposed breasts. She finished her look off with a pair of heels and glasses and made her way to Max’s study door.
She knocked on the door and heard Max shuffling papers.
“Come in, he shouted, “why the hell are you knocking-” Max stopped mid-sentence and his mouth gaped open when he saw her.
“Excuse me, Mr. Principal,” she said in her best breathy, little girl voice, “Miss Henderson sent me here because I was a bad girl.”
“Well, you’re going to have to be punished, then, aren’t you,” he said gruffly, picking up a long wooden ruler off his desk. “Come, here,”
Emma walked over to the desk with her eyes to the floor. Max reached out and grabbed her by the waist, bending her over his knee.
“Have you ever been spanked before you naughty girl?” he asked.
“Just once,” Emma smiled, remembering her experience with Chad.
Max pulled back the ruler and slapped her three times across her bare ass.
“Oh, Sir, please,” Emma begged, giggling, “spank me harder.”
“Harder, you say?” Max dropped whacked her a couple more times before dropping the ruler and he began to softly rub Emma’s wet slit with his fingers.
Emma looked up at him from under her long lashes and licked her lips. “I’m going to unzip your pants now, Sir, and you’re going to fuck me. Hard.”
Emma unzipped his pants and his erection sprung out. “Oh! It’s so big!” she gasped.
She popped it in her mouth and sucked it like a lollypop, enjoying the look of pleasure on her boyfriend’s face. When she thought he was getting too close to coming, she stood up and put her hands on Max’s desk.
“Now fuck me,” she commanded, looking at him over her shoulder.
Max didn’t need to be told twice, taking his cock in his hand, he guided it to her slick opening and thrust it inside her.
Emma watched their reflections fucking in the large mirror on the wall. Her full breasts were jiggling up and down with the force of Max’s thrusts.
“Rub my clit,” she moaned and Max reached his hand around and obliged. The combination of Max’s hard dick fucking her hard and his frantic strokes on her clit was too much for Emma. She saw Max watching her in the mirror as she came, and a few seconds later, she felt the familiar squirt inside her as he climaxed.
Sweating, Emma turned and kissed her boyfriend hard on the mouth.
“Later, I want to do doctor and nurse,” told him, fixing her shirt over her breasts, “but I want to be the Doctor and you can be my male nurse.”
Max smiled. It was a date.
The Cafe
November 20th, 2014
Another day of studying. It is raining outside and I am in the same coffee shop that I sit in almost every night, working on another paper for another class that makes me feel like a cog in a machine. But nevertheless, I had to finish my Master’s degree to get the promotion I wanted.
What I wouldn’t give for a little excitement…
I take a moment to stop and stretch. I also notice the lack of noise in the café. I look around and I see that the room is pretty much empty. There is a young woman with some incredible tattoos, reading a magazine behind the register. I bet she and I would get along.
Across the room, a man sits quietly with a MacBook and briefcase. He looks to be in his early 40’s, with dark eyes and dark brown hair with a little bit of silver coming through on the side. Somehow, the silver suits him well. I’m seriously jealous of how men age, so gracefully. His face has soft but masculine angles and is completely smooth, not even a hint of 5 o’clock shadow and he is wearing black slacks and gray button up shirt with the top two buttons undone.
I probably wouldn’t have realized that I was staring at this guy, but for him raising his eyes and looking at me, meeting my gaze from across the room. I quickly look back down at my laptop and start typing away, feeling my face flush with embarrassment.
I sat there, staring hard at my laptop and typing away at my paper, but I wasn’t really doing anything. I was just thinking about the curve of the stranger’s jaw, the clean cut of his hair, and that momentary eye contact. I risk another glance at the man only to see him looking at me. I see his face break into a grin before I cuss at myself and look back down at my work. I can feel myself getting hot and moist so I quickly cross my legs, as if the stranger might notice my excitement.
I can hear the blood pumping in my ears and the warmth in my entire body; I want to fan myself, but I am afraid to move and embarrass myself. I think to myself that I wish he would just leave, but immediately after I think it, I feel myself hoping he wouldn’t. I imagine myself touching the smoothness of his cheek when I hear a voice that makes me jump and hit the table in front of me.
“May I join you?” The stranger asks.
I look up and he is staring down at me, holding two cups and a pot of coffee. I was so lost in my thoughts, I hadn’t even noticed he had moved.
He clears his throat and makes me realize I am just sort of looking at him with my mo
uth open. Damn, I am acting like a giddy teenager.
“Uh,” I clear my throat. “Um, yeah, sure.”
The stranger sits down and pours two cups of coffee, without asking if I wanted any. I felt like I should be indignant for his presumption, until I remembered my cold, half cup of coffee sitting in front of me. Smooth Amber, I think to myself.
“My name’s Matthew.” He says. He has a nice, friendly smile, but his eyes are fierce and piercing. This is a man who commands respect and attention. I wonder how long he had been there before I noticed him, and why it took me so long.
“I’m Amber.” I said with what I hope is a smooth recovery. “Do you come here often?”
He smiles with what appears to be approval. “No, no, I don’t usually come this close to the university. It’s too loud to work.”
“Oh yeah, it does get pretty loud. What type of work do you do?” I ask, while trying not to stare at the smoothness of his chest revealed through his unbuttoned shirt.
“I’m an investment banker. Nothing interesting, really, but it pays well and I have always enjoyed the status of success.” He says this while sipping his coffee and looking at me intently for a reaction.
I feel like I should be offended or irritated at his blatant statement of success and implication of wealth, instead I feel a sense of appreciation at his honestly and relief that he isn’t just some sophomore punk who thinks he’s God’s gift to women.
“Do you enjoy your job?” I feel like I should keep him talking because I don’t want him to leave.
“Actually, I love my job. My office is great, I’m good at what I do, and I can enjoy the peace and quiet of working from home whenever I want.” He paused for a moment before saying, “Although, meeting you makes me feel like I should come down here to work a little more often. How about you tell me what you do?”
I blushed a little, but answered quickly enough to distract myself. “I’m a part-time student, going for my Master’s degree in HR.”
“What do you plan to do with it?” He asked with apparent interest.
“I’m hoping for a promotion at work, honestly.” I glanced up at Matthew; he was watching me with polite interest. I decided to switch things up a bit. “Why did you come over to talk to me?” I asked abruptly.