And the more energy she began to feel, the more right it became to allow this stranger into her as far as he wanted to go.
Teddy reached up her skirt and pulled her thong down, until it fell to her feet. As the kissing continued to fuel the fire, Sara’s eyes closed.
Now she wanted him to do with her as he would.
With his large, muscular arms, Teddy picked up Sara, with her legs wide open, and placed her on the mahogany desk behind her. She was practically salivating for him now.
“I’m going to fuck you now, Sara,” he said. “Do you want me to fuck you?”
“Yes,” was all she could muster.
“Tell me.”
She was afraid to tell him the sheer depth of her desire. But finally, after his fingers teased her pussy with expert playfulness and a contraction of sexual bliss raced through her entire body, she couldn’t help but beg him. “I want you to fuck me.”
“Say my name, Sara.”
“Teddy, I want you inside me. Please.”
Teddy’s hard cock went into her suddenly and deeply. Sara’s pussy was beyond wet, making it easy for him to slide in and out of her, generating pleasure in every fiber of her slick entrance.
He continued to move his cock in and out of her wet lobes while maintaining the unbreakable lock that existed between them. Sweat dripped down Teddy’s forehead as he held on tight to her buttocks, working himself deeply inside her.
His member was the hardest thing she’d ever felt inside of her.
His breathing sped up. “You feel so good to me, Sara. You’re so tight.”
He thrust his penis into her somewhat faster, as he clearly was about to reach his own boiling point.
Something clicked within Sara at this moment.
As his penis worked her wet insides she could feel a switch go on deep within her; somehow, her letting this gorgeous, affluent man have his way with her made her feel more powerful than ever.
The intercourse became even faster. Teddy drove his tongue deeper into Sara’s mouth as he brought her closer and closer to the edge. She clawed at Teddy’s muscular back as he thrusted his member into her body for a few last moments.
When he was finished with her he placed his large, strong hands on the sides of her neck and began to kiss her as though she was his sexual fantasy goddess. Teddy was clearly a happy man, and as Sara melted in his arms a warm glow had come over her body bringing her a deep sense of pleasure in every sense of the word.
Just Passing Time
The two lovers lay for hours under the exotic hotel sheets. Sara was truly beginning to wonder if any of this was real, but she didn’t waste too much time questioning this experience in order to better enjoy each possible moment. The billionaire was not as straightforward a man as Sara had originally presumed; the more they spoke to one another, the more she began to see that this was a man who thought deeply about things worth pondering in this life. She had initially assumed he was a simple man with exceptional looks and an unbelievable drive to succeed- and he was indeed both of those things. But he was also a man who truly savored romance, good conversation, and the little pleasures that life had to offer such as simply lounging under the sheets of a hotel bed whilst enjoying delicate exchanges of affection and the occasional sip of the suite’s complimentary sparkling cider.
“Tell me Sara, what brought you to work for Peter Barrows?” Teddy pursued with a genuine curiosity. He went on, “I mean, I don’t want to cross the line here but I’m guessing you had never intended on embarking on a career as a cranky old business man’s schedule planner.”
Sara thought for a brief moment, just as she had thought about her life’s path countless times before. “I don’t know, I kind of fell into this. I got out of college with dreams that were larger than life, and here I am. It just…”
“Happened so fast?” the billionaire questioned before she could finish her own sentence.
Sara found herself blushing. Teddy had a way of looking at her and speaking to her that made her feel so incredibly safe and understood. Here was a man who was so exceptionally rich--not to mention so incredibly hot--but somehow he maintained a warmth and sensitivity about him that most men of his stature didn’t possess.
It wasn’t very clear to her why a guy like this, who could have so many women, would be so attracted to her. To make matters even more intriguing, he was now beginning to take an actual interest in her life. And Sara wasn’t sure why, or how she felt about it.
Was he just passing the time, or did he truly want to know more about her because he had feelings for her? But then she told herself she shouldn’t be so foolish. A man like Ted Jeffries wouldn’t want to be serious with some random executive assistant that he’d had a fling with on one of his many business trips.
But Teddy was looking at her now, looking right into her eyes as he spoke.
“I know what you mean, Sara. Life has a way of swiftly taking you in directions that you had never intended going.”
Sara thought she sensed a slight hint of his own personal regret somewhere along the line of his past.
“I think maybe you and I took different directions in life,” she said, grinning a little. They couldn’t have been from two more different worlds.
He nodded and took her hand in his. “But it’s not too late to create the kind of life you were meant to live. It starts with a healthy dose of risk-taking, kind of like the risk-taking you took today. If you’re willing to make a leap of faith every now and then, good things are bound to come your way.”
Suddenly he scooped her into his arms and held her like a delicate flower. They began to passionately kiss once again.
His fingers caressed the back of her hair while her legs entwined with his. Sara could feel herself getting wet all over again; she couldn’t remember the last time she felt this way twice in one day!
Teddy’s shaft was hard as it brushed against her thigh. His hands reached down to spread Sara’s legs and make room for his now fully erect member.
This is too much.
She wondered how this could all be happening to her. This time though, there wasn’t even the slightest hint of internal struggle as she let him enter her again. It was the most natural thing in the world. Teddy worked her body, a bit more gently this time, but equally as intense. He spent more time exploring her body with his hands as he moved deeper inside her.
Her inner thighs were smooth and inviting. Her breasts were large but not overwhelmingly so. And her lips, Sara had always been a good kisser, not that she had had much practice as of late.
Perhaps it was the power of a billion unleashed hormones, or perhaps it was the two of them becoming more in synch with each other’s sexual craving- regardless of the reason- Teddy came even faster the second time around as he pulled out of her body and oozed his cum onto the back of her thigh.
This was all she could take. Sara unexpectedly let out a sweet, heavenly moan- it was her first orgasm through intercourse that she could recall in years.
Both lovers were beyond content. He placed her soft hands in his and cupped them upon his dense, muscular chest, allowing only background silence to accompany their synchronized breaths while the two drifted off for a touch of sleep.
But as she was drifting, Sara had the disconcerting thought run through her mind.
This can’t last.
She knew it was true, and her bubble of bliss was temporarily popped. She opened her eyes and looked at Teddy as he lay sleeping beside her. She was struck once again by how hot he was, his muscular arms, his perfect face. With his eyes closed, he looked like a handsome angel.
For a brief moment, Sara considered getting out of bed and leaving the hotel room without even saying goodbye. It would be easier that way, she thought. But she couldn’t bear to leave the warmth and safety of this bed. She wanted it to last as long as it could, even as she knew the pain would be that much worse when it came to an end.
As the hours passed, Friday soon turned into Saturda
y. Neither of them said anything about leaving the hotel room. Rather, they exchanged beautiful smiles, enjoyed nibbles of gourmet room service meals here and there, threw back a glass or three of wine, and engaged in lengthy conversations pertaining to just about everything under the sun. Love-making was their sole form of intermission in between the spaces that occupied their world within the executive suite.
“So Sara, did old man Barrows put you up to this whole thing? He’ll do anything to squeeze a few dollars out of me. He probably commanded you to bring me to this hotel room and seduce me,” Teddy laughed at one point.
“Me seduce you?” Sara joked back. “That’s not how I remember it.”
“Okay, okay, I admit it, I was a bit forceful. But I just had to have you. And I’m glad I made the move I did. You’re pretty damn hot if you don’t mind me saying! And don’t think I’m done with you yet.”
Teddy gave her the same look of desire in his eyes that she’d grown accustomed to throughout their time together.
“Oh really?” Sara playfully resisted. “And what makes you think I would let you have me again?”
“Something tells me you can’t resist me as much as I can’t resist you”, the confident businessman responded. “Why don’t we test my theory here?” Teddy added as he began to kiss her neck sending familiar chills down her spine and throughout her entire body.
As Saturday turned into Sunday morning, and Sunday morning turned into Sunday evening, Sara knew that she had to leave at some point. She was really beginning to enjoy this whole idea of taking risks, but at some point she had to go home.
Preparations were made for the two to say farewell.
“Thank you for everything,” Teddy said as he held her tender hand in his. “Oh, and I’ll make sure to tell Barrows about all of the sightseeing adventures you took me on,” he added. “Good bye Sara.” The billionaire took her body one last time into his arms and held her close for what seemed like an eternity. With a soft kiss on her forehead, he released her and she was off.
As Sara departed the room, walked the floor’s hallway, travelled down the elevator, and exited through the main door of the hotel’s lobby, she found herself in a state of confusion. She was determined not to over-think this whole experience. Determined.
She went even further as to make a pledge to never go back to her life of mediocrity from this point forward. From now on, she would take more risks, think more highly of herself, and enjoy the many pleasures that this world had to offer, even if she never heard from Ted Jeffries again.
She would figure out a new life-plan by reinventing all of the parts that felt somewhat misplaced. She was hell bent on starting over, but hadn’t a clue where to begin.
The Aftermath
The next morning, it was life as usual for Sara Jacobs. She arrived early to work, as she always did, even though she almost never had a full day’s worth of tasks to complete at her office job. When she arrived at her desk, she felt a wave of confusion so great she nearly felt light-headed. Did her weekend with the billionaire really take place the way she was constantly choosing to replay it in her mind? In fact, as Sara began to lose her mind a bit, she began to wonder if it even happened at all.
“Sara, snap out of it!” Mr. Barrows came barking into her office. Stunned, Sara adjusted her posture and fell immediately into her role as an executive assistant.
“Sorry, I was just thinking about rescheduling your three o’clock appointment like you’d asked me to.”
“Don’t think about it—do it, Sara.” He shook his head and sipped his mug of coffee, as per usual. The slurp grated her nerves but she forced a smile.
“Of course. I’m doing it now.”
Mr. Barrows stood there and looked at her. “Soooooo…How did it go with Mr. Jeffries?”
“How did it go?” she parroted, trying to buy herself some time.
“Mr. Jeffries, Sara. How did it go? Did you show him around the city? Did you make sure he enjoyed himself? Did you make him feel at home?”
“Oh, yeah, Mr. Jeffries”, she spoke as she tried to pull herself together. “Things went well, I think. I hope. I don’t know.”
“You think? You hope? Sara, I have a meeting with Mr. Jeffries at 10:15 this morning. I have one chance to get him to buy into this new development project. Speaking of hope, I really hope you didn’t blow this one for me,“ Mr. Barrows added.
Sara began to spin off into her own world as Barrows bellowed on. She began to replay the sexually charged love making sessions that she and Teddy engaged in over the course of the weekend. She was remembering his hard manhood inside her wet entrance.
She could practically taste his skin as she recalled the way he swept her away inside that hotel room.
As Barrows took his tyrannical side-show away from her desk and into his office, Sara could feel herself heating up at the mere recollection of the sensational events that transpired with her billionaire weekend assignment.
She checked to make sure her boss was nowhere in sight, and then she began to pleasure herself, touching herself over her black lace panties.
She was so wet. She wished Teddy was with her right now, she would be so ready for him to go inside of her again and again and again.
This was not the sort of activity that Sara would have even considered partaking in prior to being taken in the hotel room by Teddy Jeffries. To be clear, she would not even so much have returned a library book past its due date before a weekend such as the one she had just experienced, and now here she was, masturbating at her desk with her cranky boss easily within throwing distance.
But she needed this, she needed the adventure; this would in fact be her first step in making the type of life changes that she had vowed to make the moment she departed from the billionaire’s hotel room. This was a good start, she thought, and as she continued to work her wet folds between her legs, the play-everything-safe voice in her head was drowned out by raw eroticism. As she climaxed at her computer monitor, a wide smile spread across her mouth. She now knew, the old Sara would not be coming back.
Sara’s Evaluation
Later that Monday afternoon, Mr. Barrows came nearly bursting into her office. “Sara, I gotta hand it to you, Mr. Jeffries said you were phenomenal, that you really made him feel at home here in the Windy City.”
Barrows practically had neon dollar signs glowing in his eyes. “Jeffries said if it wasn’t for you, he probably would have just lied around his hotel room the entire weekend. He even went on to say that he credits you with his final decision to invest with our company for our next commercial development venture.”
“That’s great Mr. Barrows,“ Sara said with a hidden smirk. All the while she was imagining how much fun Teddy must have had pulling her boss’s chain for the sake of making her laugh.
Barrows was beyond ecstatic about closing the deal with Ted Jeffries. He began to leave Sara’s office but then stopped suddenly, “Hmmm, I feel like I’m forgetting something.” Barrows searched every crevice of his aging mind. “Oh, Got it! Here Sara, Jeffries wanted me to pass along this thank you note for taking such great care of him this weekend.“ And then Barrows passed her a sealed card that had her name on it.
Sara mustered up every ounce of strength she could to not let out a happy squeal. Her mind was going haywire. As she reached to take the card from Barrows, a feeling of dizziness came over her body. Sara sat down with the card and quickly pretended to get back to more important matters in a desperate attempt to rid herself of her boss immediately.
With Barrows gone, she opened the envelope slowly. She made a promise to herself that she would not be let down by any of the card’s content; that she would in fact expect very little in terms of significance from whatever it is her former seducer had written. She was, in fact, a new woman, regardless of Ted Jeffries. She worked hard trying to convince herself that he was merely the means to her new life and was no longer essential from this point forward.
With a short pause, Sara pres
sed on and began to open the envelope. As she pulled the card out, the cover revealed itself with a simple and rather generic “Thank You” imprinted on it.
She opened the card. In it read the following:
Sara, I cannot get you out of my mind, and I don’t intend on trying anymore. Our time together was amazing, to say the least. Please consider visiting me in L.A. next weekend if you are free, and if you are willing to take another risk. With Love, Teddy
Sara couldn’t help herself as she rather loudly exclaimed, “Yes! Yes! Yes!” She began pacing in circles around her office as if she had just won the lottery, but was somehow forced to contain the joy of her victory.
Barrows came barging into her office, “What in hell is going on in here Sara?”
Sara couldn’t control her excitement any more, in fact she had been controlling herself for too many years and she was done repressing her emotions as she jumped on her boss and squeezed him like a giant stuffed animal.
A stunned Barrows stood motionless for a moment, then began to peel his assistant’s arms off him. “Sara, I’m not sure what’s gotten into to you, you may have lost your mind for all I know. But lucky for you, you are on my good side for a good chunk of time because of the work you did with Jeffries. Try not to be so loud though, will ya?”
“Sorry Mr. Barrows, it won’t happen again” she stated as she began to scream some more- only this time she kept the screaming silent in the confines of her own mind. Holy crap! Holy crap! Holy f-ing crap! Sara was beside herself with excitement.
As Mr. barrows exited her office- she didn’t waste a moment searching on her computer for flights to L.A. for the following weekend. My how quickly my life has changed! Sara began to reflect on everything that had just transpired. With good timing, a healthy dose of luck, and the willingness to stretch her own personal limits beyond the imaginable, Sara’s life was finally beginning to unfold in ways she had always wanted it to. Ways that she always knew- deep down- were possible. The irony of it all, Sara delighted, is that allowing herself to get taken turned out to be the surest way to get more back from this world.
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