tagRomanceMy Sexy Boss

My Sexy Boss


John sat nervously in the lobby. This was a very important job interview and a job he desperately wanted.

John sat, eyes focused on the ground, shaking his leg anxiously, until a woman's voice called out his name.

John looked up. Standing before him was a beautiful woman.

The woman extended her arm out and said, "Hi, I'm Antonella." She had soft-spoken, yet sexy voice.

John snapped out of his daze fast enough to respond, "John Bourke. Pleasure to meet you."

John followed Antonella through the building, into the elevator, and eventually found himself seated in her office. The five-minute trip seemed a blur because he couldn't take his eyes off of her. She had long straight blonde hair. Amazing blue eyes. A beautiful face matched with a thin, tone figure. You could tell she was a frequent gym visitor. She looked very professional in her matching dark blue suit, silk blouse, nude colored stockings, and a pair of black pumps that to John's dirty mind just screamed, "Fuck me." John was taken aback immediately and wasn't sure he could focus on the interview. Antonella was polite and attempted to carry on the conversation on the way up to her office. She talked about the traffic and asked if he had a hard time finding the place, to go along with the typical greetings. John couldn't muster much of a response, other than a few "Ok's", "yes's" and "no's."

John's mind was wandering. Was the blouse on underneath a full sleeve one or the one that resembled a piece of negligee. He wondered if she would take off her suit jacket during the meeting to find out. His eyes wandered towards her silk stockings and he wondered if they were the thigh high kind and if so, did she have on the matching garters? A part of him hoped, when she sat down at her desk, her skirt would be short enough that he could find out. Finally as he walked behind her as she led the way to his office, he couldn't help but glance at her shapely behind. He could have sworn he sore the panty line. Or was it a thong?

The interview went by fast. John was sure he was too distracted by her charm and good looks that he would be rejected for the job. And he never found out the answer to what kind of blouse or stockings she had on.

It was a sleepless night for John. Did he ruin his one chance to make a good impression? Would he ever see Antonella again or would she be just another fantasy, a memory that he would remember forever and possibly ruins him for all women to follow?

At around ten the next morning, he was suddenly awaked to the sound of a ringing telephone. He reached for the phone and saw an unfamiliar phone number on the display. He answered with a groggy "Hello."

It was Michael Donovan from the Human Resources department. He had good news. Everyone was impressed with John and they wanted to extend him an offer. John was beyond excitement. Not only did he get he job he desperately wanted, but he would also get the opportunity to work with Antonella.

Work was busy, but it was what he always wanted to do. The first day, they welcomed him with a group lunch (on the company tab). As he sat down surrounded by five other women (including Antonella), the talk soon turned to marriage and babies, as one of the ladies was engaged and another was 4 months pregnant. The group of women eventually got on Antonella's case. It seems she was the only one single. Antonella had always put career first and it affected her personal life. All John could remember, other than it felt weird being left out of the conversation because he was a guy and that he did not need to hear about C-sections and wedding planning issues, was that Antonella was available, and maybe, just maybe he had a chance.

As he spent more and more time with Antonella, his crush grew to love as he grew a much greater appreciation for her. Her intelligence matched her beauty. She was hard working and a pleasure to be around. She had that effect on everyone.

John desperately wanted to say something to her. He wanted to confess his love. But all he really wanted was a date. But it didn't seem appropriate to ask out your boss. Every night, the thought of approaching her crossed his mind. They even had some brief run-ins, where he thought maybe there was something there. There was Christmas when the entire department chipped in and bought her a gift. She was so grateful that she thanked everyone, but she gave John a hug and kiss on the check when she thanked him. There was the holiday party where they shared a drink and a dance. Then there were the frequent group birthday lunches where he somehow (whether through luck or coincidence) always managed to sit next to her. Their conversations were always pleasant and there seemed to be a connection there. Maybe she felt something for him as well. But John could never tell with women. He couldn't tell if she was dropping signs or if he was simply looking for them.

At times, he would wonder if he felt love or lust for Antonella. He was very attracted to her and would want nothing more than to make love to her. Or did he just want to fuck her? Another notch on the belt? He kept telling himself that couldn't be it. He liked her as a person, not just a piece of ass. But there were definitely moments at work when he fantasized about just taking her and doing all the nastiest things to her. The problem was that Antonella definitely dressed sexy, albeit professional. She felt comfortable in her own skin and didn't mind showing off her legs and other body parts. In the summer time, she would wear skirts, dresses, and tops that fit her perfectly. In the wintertime, she would wear stockings. When she had an important meeting, she would always wear one of her sexy business suits. And she would always wear heels. She had a wide array of them. Open toed, pumps, strappy, stiletto. You name it, she wore it. And John was a sucker for a woman dressed like that.

After working there for some time, John started fantasizing about Antonella while at work. He would imagine the two of them going off on business trips together or working late together. Being alone together would provide the opportunity for John to finally seize the opportunity. But that opportunity never presented itself.

Until one late night at the office, both were working late on a major project. She was dressed in a simple black skirt that stopped right before her knees, black stockings, with a creamed colored thin turtleneck, and of course a pair of sling back heels. Just the kind of casual, yet sexy outfit that drove John crazy. As they left to call it a night and exited the building.

together, John was shifting back and forth on whether he should say something. As he walked her to her car, he once again chickened out. She got into her car and they said their "goodnights" as John walked away disappointed at himself. But as he walked away, he heard the rumbling sound of an engine. He turned around to see Antonella was having some car problems. He walked back to ask her if everything was ok. It was not and John was not an expert with cars, so he couldn't offer any help. So he just waited around with her as Antonella called for tow truck. But to her dismay, no tow truck could get out to her for at least a couple of hours. She was about to leave her car there for the night and just take a taxi home, when John offered her a ride home. At first, Antonella didn't want to bother John, but when she found out that a cab would be at least a 30-45 minute wait, she finally took John up on his offer.

The car ride was quiet as Antonella was visibly upset from the long day. John was playing all the scenarios in his head, as he pondered what would happen if he told her. But when the possibility of making love with her got into his head, he just couldn't get it out. He imagined sucking on her breasts. Licking her thighs up and down. Tasting her. He imagined her mouth wrapped around his manhood. And the thought of being inside her blew his mind. Before he knew it, he had a huge bulge in his pants. He tried to cover it, but it was pretty obvious. John tried to get the erotic thoughts out of his, but it didn't work. He just prayed that Antonella didn't notice.

Antonella was exhausted. She had been pulling 10-12 hour days for the past month. The last thing she needed was the hassle of having car trouble. She just wanted to go home and lie in bed. She was so thankful that John was around that night. He had been a real help on the project and she enjoyed working with him. She looked over at him to thank him. But her eyes wandered and found their way to his crotch. At first, she thought she was imagining something. But after getting another look out of the corner of her eye, she was sure that he had an enormous hard on. At first, she was appalled. She didn't know how to react. But then she felt a tingling sensation between her thighs. To her shock, she was immensely turned on and getting extremely wet.

Now she was trying to hide the fact that she was turned on. She moved around in her seat a few times. Then it occurred to her that he was turned on by her. It had been so long since she had been intimate with someone. She decided to make a move.

John was completely taken by surprise. Antonella was massaging his hard on through his pants while kissing his neck. He almost lost control of the car. Thank god they were nearing her apartment. He pulled over to the nearest parking space in front of her place and parked the car. He grabbed her as they kissed passionately. All the pent up anticipation caused him to practically suck her face off as they kissed. His hands explored her entire body. He caressed her breasts while she continued to rub his bulging hard on. He slid his hand down.

her stomach and finally slipped it up her skirt. He could feel the wetness through her thong. Antonella slowly unzipped his pants and let his manhood breath as they both moaned with passion.

They somehow managed to get into Antonella's house. Neither John nor Antonella could remember how they got out of the car and in the door. Hell, John couldn't even remember if he zipped his pants back up. They barely got past the front door before John pushed Antonella up against the front door and bent her over and started tasting her from behind. John didn't even bother taking off her clothes. He just lifted up her skirt and slid her panties down around her knees. Antonella moaned as John maneuvered his tongue in a continuous circular motion. John was amazed at how sweet and clean she tasted. Antonella hadn't felt this good in so long, and in no time, she came with a fury. Her whole body shook. Antonella then whispered that it was his turn. She stood him up and got down on her knees. She opened her mouth and sucked every inch. She stared up at him the entire time. The look on John's face made Antonella remember just how good she was at this and how much she enjoyed pleasuring a man.

John could not take it anymore and knew if he let Antonella continue, he was going to explode in her mouth. He stood her up as they kissed again, practically tasting each other's cum. Antonella hoped John had a condom, and to her luck, he always carried one in his wallet. John slid on the cover and picked Antonella up in his arms. He pushed her against the front door as he entered her. They kissed the entire time as he pumped and thrust. He started pounding away as hard as he could, throwing her body against the door, even banging her head a few times. They didn't even bother stopping. From the door, they slid down to the floor. John lifted up her turtleneck to reveal her nice breasts. He sucked on each one as she bounced up and down. Her heels dug into the hardwood floor, scratching the surface with each bounce. While still inside her, John lifted her up and carried her over to the nearest couch. He laid her on her back and stood up to gaze over her. She was still clothed, but all the right parts were revealed. Even John didn't manage to get out of his pants or shirt. He lifted her stocking covered legs and placed them on his shoulders. Each thrust shook Antonella's entire body and her legs and heels flailed in the air. She looked up at John with those beautiful blue eyes and John finally could not take it anymore. He released all his fluids inside the condom. It was the best feeling he ever felt. They both collapsed on the couch, breathing heavily.

As Antonella fell asleep in John's arms, John thought to himself sometimes, the moment is worth the wait. And by the way, she was wearing thigh high stockings and matching garters...

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