LOGINOlivia
“Have you even accepted ONE contract?” Sharon asked me as we sat on the patio, day drinking.
“Not yet,” I said as she rolled her eyes. “I will, eventually.”
“You’ve been with the company for at least 4 months now and you haven’t met with ANY one yet! Why even bother if you won’t try? I’m sure Robert would have tried at least a dozen women by now!” She quipped, gulping down her drink.
She was upset with me. She was right. Robert would have fucked each and every woman he would have come in contact with. I couldn’t explain my hesitation.
“I don’t know what is wrong with me, Sharon.” I said gulping down my entire glass of wine and pouring another.
“It’s because you’ve been faithful to your lying, cheating husband for 25 years. You need a new dick!”
I looked down into my glass and smiled. Sharon was blunt and straightforward, something I envied in her. I always wished I was more outgoing and brazen, but I was too timid and afraid. I needed to embrace my inner 'Sharon'. I would go online tonight and pick a contract.
"Don't you think I'm too old?" I asked as my mind began to wonder.
"Honey, you're in better shape than most women your age.
"Really? I have some gray hair."
"Who the fuck cares. You have great tits and a hot ass."
"I guess."
"You will find someone. The guys will love you." I smiled. "Do you want me to help you out? I could get you some names if you want." She asked.
"Oh no, I will be fine."
"Suit yourself." She said, pouring another glass of wine. "Just as long as you pick someone and do it soon."
"I will, I promise."
I went inside the house, walked upstairs, and went into my bedroom. It was a huge master suite with a king size bed, walk-in closets, and a fireplace. It also had a balcony where we would make love, or so we used to. Robert was so busy fucking others he dare not think about me. Fury began to burn in my soul. I opened my laptop and noticed I had received a new request for the contract. I didn't even look at who it was, I took the initiative and followed Sharon's advice and accepted the contract.
"Fuck!" I yelled out. I couldn’t believe I had done it.
Sharon immediately called out as I walked back out to the patio.
" What's going on?"
"I just accepted a contract without even looking at the name." I sat down in a daze.
"So what's the problem?" She asked.
"Well, I don't know who it is."
"So, open up the damn file and find out."
"I can't," I said hesitantly.
"What the hell is wrong with you?"
"I'm afraid."
"Jesus Christ, just look."
"No." I didn’t want to see who agreed to fuck me.
"Then give it to me. I'll look for you."
"Oh god, Sharon, no."
"Then stop whining and grow a pair. You signed a contract and now you have to face the consequences. Go back inside and open the file. Once you find out who the hell it is, let me know."
She was right, I had to grow a pair. I figured I would examine the file later on just before bed. I would be able to learn when my initial meet and greet would be with the mysterious contract holder. I didn't have to worry about anything because Robert wouldn't be home until the weekend.
After taking a shower and grabbing a snack of cheese, crackers, grapes and a glass of moscato, I was ready to look at the individual who sent the contract. I hesitated a bit as I opened my laptop, but I kept hearing Sharon telling me to grow a pair so I did. I opened the email and took a sip of wine as I opened the file which was sent to me. I clicked on the link of his profile picture and choked on the moscato.
I couldn’t believe who accepted the contract! I would have never thought!
I’m so glad Sharon didn’t open the file as she suggested earlier.
Tony
Training went about as good as it was going to be, I learned a lot of stuff that definitely increased my face value. I felt more refined, optimistic and confident; I engrossed myself in learning about the branding side of business and international e-commerce in order to expand our business in the future. I couldn’t believe the knowledge I had gained in just 4 months, the classes were so intensely focused and interactive which helped a lot.
“Mr. Hamilton,” Peabody called out to me as I completed my last class for the day. “Can I speak to you for a moment?”
“Of course.” My heart skipped a beat, I was intimidated and anxious thinking I had done something incorrect. “Is everything okay?” I approached him standing on the other side of the hallway.
“Yes, everything is fine. Follow me to my office.” I nodded and Peabody led the way.
I always admired Peabody, he ran this entire company. This was his dream and it worked well. Everyone respected him because even though he had a quiet demeanor, he was a caring individual. And everyone knew he cared deeply for Ms McBride.
We reached his office and I took a seat as he closed the door and sat down behind his desk. I watched as he shuffled through a few files sitting on his desk, pulling out a file from the middle of the stack and opening it in front of him.
“Mr. Hamilton, this is your last day, correct?” He flipped through the documents without looking up.
“Yes, Sir.”
“Good.” He looked up and folded his hands atop the file. “How were your classes?”
“They were good,” I adjusted in the chair wondering where he was going with this conversation. “I had no problems.”
“I see. I’ve heard you actually excelled.” He mentioned smiling slightly, easing the tension in the air. “In all of your classes.”
“I did?”
“Yes, you did.” He closed the folder and placed it on the desk in front of me. “This is a new contract. It will be your first. You are able to deny it, if you feel as though you will not be able to fulfill the contract.”
“Deny it? Contracts are denied?” I shrugged at the thought.
“It depends on the individuals involved. However, every contract is eventually fulfilled.”
I looked at Peabody while he sat back in his chair; It made me curious why a contract would be denied. I picked up the file and opened to see the contract owner and was absolutely floored. My dick instantly hardened at the taboo that it created. The thought had crossed my mind for a long time as I gazed at the photo of this beautiful woman.
“She has a contract with us?” I asked, still looking at the picture and flipping a few pages, reading her background.
“Yes. She opened it just around the time you came on board with us.”
“Really?” I looked at Peabody who was smiling back at me.
“I can only assume by your reaction, you know this woman. Am I correct?”
“Yes. Yes I do.”
“I figured as much. That is why I brought this to you. She has not accepted any requests since she opened her membership.”
“Seriously? Why?”
“I was hoping you may be able to find out.” Peabody looked at me as he pulled another file from the stack on his desk.
“Uh, well. Well, there’s this thing.” I stammered as I blushed at the thought of being with this woman. I’ve had numerous thoughts about her but I would have never guessed I would be in this position to send a request of that nature.
“I already know.” Peabody interrupted. “That’s why I figured maybe you could help her.”
I could help her, but how would she react to seeing me as her escort? I was intrigued which excited me more to go through with accepting the contract.
“Let’s do it. I’m interested.” I smiled and Peabody nodded.
He quickly began typing on his laptop, most likely setting up the contract between myself and the contract holder. The contract holder was someone who I had never expected to create a contact in the first place, considering she was married. I must admit I was thrown off but I had been admiring her for a long time now.
“Mr. Hamilton, do you think you will be able to keep this as discreet as possible?”
“Of course! The last thing I need is for my mother to find out.” I shook my head realizing what I had just accepted.
‘I was thinking the same thing. However, it was your mother’s idea for the client to join.”
“Really? I could see it. I’m sure she had good intentions but she surely didn’t expect her son to be matched with her best friend.” I smiled. Peabody chuckled at the thought.
“Interesting.” Peabody tapped away on his laptop and smiled. “Well Mr. Hamilton, it looks as if your request has just been accepted.” My eyes bulged out and my mouth dropped open.
She accepted the request! Excitement filled my soul as I had just realized one of my wildest dreams just presented itself to me. The opportunity of a lifetime! Suddenly, I realized she accepted me!
I wondered how long she had been thinking about being with me! I’ve always found her to be very attractive, it was just something about the way she would look at me when she would visit my mother. I’ve had a secret crush on her since I was a teenager, but I never thought I would actually be with her.
However, I knew about her husband. He’s an egotistical asshole who under-appreciated and under-valued her for so many years. I overheard her tell my mother that he was her true love; a true love that breaks her heart. She and mother have had plenty of conversations about their relationship and how he doesn’t satisfy her because he’s usually too tired after fucking someone else hours before.
She was a woman who was in her prime and I was excited she granted me the opportunity to be the one to give her an experience of absolute satisfaction. I smiled as I gazed at the picture attached. I blushed at the thought of our first meeting as client and escort; I closed my eyes and slowly shook my head.
“What’s going through your head, Mr. Hamilton?” Peabody closed his laptop again, moved from behind his desk and walked over to his mini fridge, removing two beers. “How are you feeling right now?”
Peabody was the kind of individual that was a boss and a friend at the same time. He knew I had a lot on my mind. I was filled with so many questions and feelings, I was excited and scared at the same time.
“I didn’t expect it would be someone I knew, I guess.”
“Understandable,” Peabody opened the bottles and passed one to me. We clinked the bottles and I took a long gulp. “Is this your first mature woman?” he asked.
“Yes,” I said. “I knew it would be a possibility taking this position, but I guess I thought I would be more prepared to be honest.”
“I was the same way,” Peabody uttered as he took a long swig of his drink and sat down behind his desk, crossing his feet on the desk. “When I was offered the assistant position to Ms. McBride. I was terrified”
“Really? I could imagine. She’s very intimidating.”
“Yeah, that’s because corporate America is a cutthroat atmosphere. She had to prove herself worthy of a spot at the table in a world dominated by men. She had to play the game and she learned how to master the game and bend the rules in her favor.”
“Damn.” I was mesmerized by her story.
“She hired me with no experience as she molded me to become what she needed in her life.” He smiled and drifted away, sipping on his Heineken.
“Was she your first mature woman?”
“No, but she was the only one that cared about me. She treated me as her equal and confidant. And over time, our relationship flourished to what it is now.”
“Wow.”
“Don’t overthink it. Just become what she wants and needs, if only for a moment.” he said finishing his beer.
“So just take one date at a time.” I gulped the remainder from the bottle.
“Exactly.”
TonyI called Matt on the way to the office to close out my contract with Olivia. He was thrilled to hear about the service, but he said he couldn’t do what I do. He said he would find himself becoming attached to someone.“Besides, I think I’m already stuck on the person I’m seeing.” Matt admitted.“Ah, I see. You sure it’s not just the sex?” I pushed the button for the office floor in the elevator.“I thought it was at first,” he chuckled. “Only because I figured she wasn’t serious. I’m still not positive.”“You’re not positive? Don’t you think you need to know what the expectations are before you admit you’re falling in love? That’s being vulnerable
SharonOlivia had some timing. Matt and I had just finished fucking in my bedroom when she banged on the door. Matt played it off well pretending to pick up and deliver something for Tony. We were grabbing our clothes hoping they weren’t inside out due to us snatching them off when he arrived. We normally would take a shower afterwards and go another session but that was called off due to Olivia finding Robert with two women at the house. I knew it was just a matter of time before Robert started taking advantage of the situation with Olivia being out of the house on the weekends. She’s gotten hooked up with someone that is rocking her world and I couldn’t complain, I did the same exact thing. Shit, I have Matt tapping me very well at the moment and I really didn’t expect that. I’ve seen this young man grow up and pay very close attention to the needs of a woman. Our connection is so deep it's intoxicating and I don’t want to give him up. I was going to ask him to stay the night, but
OliviaThe rest of the weekend was absolutely magical. Tony knows exactly how to please a woman. I must admit that it was the first time I had gone without underwear the entire weekend. There was no reason for me to pack them as they would have never stayed on. Tony and I fucked practically all day, three days in a row.My thighs hurt as I walked in the house from our trip. We had sex one last time early in the morning as the sun was coming up on our last day together - my contract was over. Tony had the service drive me home while he went to the office. I didn’t want it to end, I could have lived inside the fairytale with Tony for a lifetime, as long as I didn’t get older - which is inevitable. I wanted to check my bank account to see if I could afford another contract. I’m pretty sure I could but I completely understood why Sh
OliviaTony made me addicted, something that I hadn’t planned. He made me feel seen, wanted and cared for and that was a feeling I hadn’t had in a very long time. I didn’t want this feeling to leave. He opened me up and tapped directly into all of my sexual desires. If only he was older and I had met him before Richard, we could have been amazing together. What we have now is something that is uncharted for me. I was not prepared to connect with someone so young beyond it being sexual.My connection with Tony was natural because of our history, which made it so easy to grow feelings for him. I needed to keep them under control because this could go so wrong and once it gets off the rails, it’s so hard getting the rhythm back. I woke up to birds chirping in the background along with a nice cool breeze across my back as I laid on To
OliviaThe weekend was finally here and I was anticipating being exhausted the entire time. Tony arranged for another car to pick me up and I was ready and waiting. Just as I was leaving the house, I saw Sharon leaving as well.“Hey Olivia!” Sharon waved as she walked down her walkway leading towards the waiting car. “Have a fantastic weekend!” She said excitedly.“Thanks Sharon, I will!” I waved back as the driver exited the car, opening up the back door. Inside, to my surprise, Tony was waiting for me. My eyes bulged and my mouth opened as I entered, having the driver close the door behind me. “Tony, what are you doing here?”He grinned before leaning over planting a soft kiss upon my lips. “I wanted to see you. I couldn’t wait until you came to me.” Tony looked as if he wanted to devour me right there in the car. “But you’re mother?!” I uttered. “Don’t worry, she can’t see in here, the window tint is too dark. All she knows is the service has picked you up.” He smiled confidentl
OliviaI feel exhilarated! I feel as though I could run a marathon. It was a refreshing change from having had to deal with my non-existent husband. Being with Tony allow my spirit to run free as we fucked the entire night and again in the morning. With him being a younger guy, he had the stamina to ravage me relentlessly. Sharon was right, I was missing out on the younger guys. He was absolutely phenomenal and I can't even share it with her, she would kill me to know that I fucked her son. And planned to do it again over a weekend. Tony hadn't told his mother that he worked for the service she suggested I try. It was a great idea since Robert was fucking everyone else except me. He didn't need me as his wife anymore, he had found replacements. And so did I. I planned to meet up with Tony for a long weekend, enjoying having him between my legs repeatedly. I didn't imagine I would enjoy myself with Tony, but he makes me feel so comfortable.I was lounging in the backyard near







