First Date

Olivia

I decided to confront the elephant in the room so to speak and dialed Tony’s number.  I wasn’t sure of what to say, but I had to start somewhere. The phone rang twice and just as I was about to hang up, he answered.

“Hello?”  His voice even sounds young, yet sexy. 

“Hello? Anthony?” I asked, hoping I dialed the right number. 

He cleared his throat and spoke again, “Yes, this is Tony,” 

“Hello, it’s Olivia,” I blushed, saying my name. I felt like a teenager calling a boy that I liked. 

“I know who you are. I was waiting to hear from you,” he answered slowly and calmly. 

He was waiting to hear from me? My heart pounded in my chest. Thoughts raced through my mind, was I doing the right thing? Why not? Robert has done so much more, I thought. I needed to go through with this. 

“Oh,” I couldn’t get much more out. I started panicking. 

“Olivia, I was shocked when I received your contract,” 

“It’s understandable. I was shocked when you accepted it,” I smiled as I made myself a mimosa. I figured I might as well get in the mood for this conversation.

“When I saw you had become a member and opened a contract, I was curious,” he started. I took a sip of courage and let it flow through my body, and channeled my inner ‘Sharon’. I was going to do this and I was going to do it well. 

“Curious? How so?”

“I always thought you and Mr. Freemont were in a solid relationship,”

I smiled at the thought of him thinking I was happy.  “Not solid at all. It hasn’t been for a long time,” 

“I see,” he exhaled. I closed my eyes thinking about his lips against the phone. “Well, I aim to make sure you are fully satisfied,”

I inhaled quickly and held my breath. I drank the remainder of my mimosa leaving me needing to pour another. The confidence in him spewed through the phone and it awakened something deep inside me, beckoning me to see what he had to offer. 

“Well, I’m looking forward to it,”  I smiled as I threw the empty champagne bottle in the trash. “And what about your mother?”

“What about her?” A grin spread across my lips as a wish for me was finally coming through.

I was going to bed this young man and enjoy every part of doing so. 

“She does not need to know this even happened,”

“I agree,” Anthony said softly from the phone. “You know I’ve always admired you,”

“You did? How so?” I sat down on my lounge chair and continued the conversation.

“I would watch you plenty of times when you were over speaking to my mother,” he admitted. 

“Oh, why?” I remembered on several occasions I would catch Tony hanging out with his friends, Matt and another young man, glancing at me from time to time. 

The boys were always at Sharon’s house and I was there because she was the second reason I wanted to stay in this area - the house was the first, with hopes of filling it with children. With that not happening it became the house and Sharon. I fell into a slump.

“Well, you seemed happy all the time, I would have never known you to not be happy,” 

“How would you know?”

“Because my mother did the same thing. She always put on a happy face, no matter what she was going through. No one would even know,” he answered. 

He was right, Sharon went through a divorce. It was awful, she was devastated but she never showed it. She held her head high for her son and others while crying in the bedroom under the covers at night. 

“Oh,” Things had taken a turn in this conversation. It brought back feelings that I hadn’t felt in a long time. I didn’t want to rekindle that feeling again because I knew the pain Sharon was dealing with at the time as it’s a living hell when someone like me is still going through it. 

“I didn’t mean to cool off the mood,” he started. “Why don’t we do this? Why don’t we meet for a little something to eat, are you hungry?” Tony asked.

“Right now?” My stomach growled loudly putting its vote in for nourishment. I had about three mimosas, I needed to have food. “Sure, I could go for some food,”

“Great, I’ll send a car for you, I know a nice place that you’ll enjoy,” he confirmed immediately. “So about 30 minutes a car should be there to bring you to me,” his velvety voice spoke to my love nest and she quivered. It was the ‘bring you to me’ part that continuously rang in my ears. 

“I’ll be ready,” I smiled with a heightened breath. We disconnected and I froze for a minute. 

This was all so surreal!  I was extremely excited and panicked all at the same time! I wanted to tell Sharon so badly, but THIS is something that I couldn’t tell her - ever. I wouldn’t know what to say to her. I don’t even think she knows he works for the same company of which she’s a member.

I quickly jumped in the shower, washed my hair and dressed in a light and flirty summer dress all in the matter of 20 minutes. I didn’t bother putting on a pound of makeup, today was going to be a hot one and I didn’t want to melt. I put on a simple coat of an airy, hydrating foundation and sunscreen. I had great skin and was blessed with natural beauty, which allowed me to have that ‘no makeup look’ while actually wearing no makeup.  

The car arrived right on time as Tony stated, with blacked out windows and a driver that held the door open. I entered the car and there waiting for me on the seat was a rose, a gift and a card. I smiled as the driver closed the door while I opened the card.

It read: Thank you for accepting the contract, I appreciate you more than you know. I want this experience to be everlasting and my goal is to make sure that all of your sexual desires are fully gratified. There is no rush as there is no time limit, only the end result of satisfaction. 

Yours, Tony

He said, Yours. Mine. My heart skipped a beat. Mine. I opened the small gift box and it was a necklace with a  small heart covered in diamonds. It was a beautiful gesture, he made my heart sing of how it felt to feel romance again. I immediately put on the necklace and held the rose to my nose. Closing my eyes I inhaled the scent making me smile dreaming I was in a rose garden with Tony standing and waiting for me.

My heart pounded in my chest feeling like a bass drum beating in a parade. I was giddy, feeling like I was a teenager again. I couldn’t stop smiling. I wanted to see his face as if I had never seen it before. This would be on a different playing level altogether. 

Tony

Olivia was on the way and I was excited. My mother’s best friend, the person I have had many nights watching and dreaming about her, is coming to see me. I’ve jerked off at the thought of her so many times, I’ve lost count. This is so fucking surreal and I can’t tell Matt because he doesn’t know this is what I do for a living. 

Yet with Olivia, it’s something different. I don’t know how to explain it, but it is. It’s still a job, but I expect her to be a long standing customer. We’re both adults and she’s still married, but she needs some fun in her life. She needs to feel loved in her life and she needs someone to make love to her continuously in this life. 

I had the driver pick Olivia up and bring her to Kitchen + Kocktails in the River North area. It was a great brunch spot that had great food, great cocktails and a great atmosphere where we could enjoy each other’s company before we changed our original relationship. I was outside when the car pulled up with Olivia. The door opened and my heart pounded so quick as if I was about to have a heart attack; I held my hand out to assist her getting out of the car. She smiled as her hand glided across, lacing her fingers with mine. 

“Hello Olivia,” I smiled as we walked hand in hand towards the entrance. “I see you got my gift, it looks beautiful on you,” 

“Hello Tony,” she blushed. “Thank you. This feels so weird,” she was a bit unsure. I needed to make sure she understood, we were both adults and were able to make our own grown up decisions. 

“It’s different, yes and unexpected. But, I think it’s a bit easier because we’re not strangers,” she looked at me with caring eyes. She understood what I was trying to say. Olivia tilted her head, covering her beautiful smile.

“You’re right,”  she said. I took her hand away from her face.  We stopped just inside the restaurant.

“You have a beautiful smile, you shouldn’t hide it,” she smiled even greater, so much so it made me smile. I squeezed her hand and led her in for our reservation. I was able to get a last minute reservation, with the help of a friend of mine because this place was consistently booked. 

We were led over to the booth.  We scooted around to the middle which I thought was cute because she was comfortable enough, yet a bit timid to be next to me. I passed her the menu and looked over the wide variety of food. 

“I’ve never been to this place, this place is amazing,” Olivia said looking at all they had to offer. 

“It’s a great place. I just was able to squeeze in because it’s usually packed,” I looked around and almost every table was taken. 

“I see,” she smiled at me, appreciating how I was taking care of her. “Thank you, I really needed this,” 

“Well I hope you enjoy yourself, Olivia,” It sounded a bit strange calling her by her first name as if I hadn’t done it for years already. But this time was different, I didn’t see her as my mother’s best friend. I saw her as a beautiful woman who needed someone to fan the flames of her desires. 

“I hope so too,” she blushed as she glanced back at the menu. 

We decided to order a few dishes to share as well as eat, we weren’t in a rush and I wanted her to be as comfortable with me as possible. I didn’t need it getting weirder than what it already was. I kept having to tell myself, this wasn’t a dream. We ordered everything from Nashville Hot and Hot Honey chicken and waffles, to shrimp and grits, macaroni and cheese, ending with dream eggs with blackened shrimp. To top it off, the drinks were fabulous, we both decided on getting the sparkling Mimosa tower. 

“I would have never thought the two of us would end up like this,” she chuckled, covering her face, blushing from slight embarrassment. 

“I wouldn’t have ever guessed for sure,” I took a sip of my drink. “However, the thought was always there,”

“Really?” Her eyebrows raised as her eyes grew wide. “You’ve thought of being with me?”

“Very much so,” I turned slightly toward her and held her hand. “I wish you could see what I see,” I whispered softly between us gazing into her eyes. 

“I want to see what you see,” she exhaled. “It’s been so long, I don’t know how to act,” she smiled nervously. 

“I can tell,” I chuckled. She bumped playfully with her shoulder.

“How did you get so smooth?” 

“My job. At Your Service has an extensive yet valuable training program,” I grinned. She patted me on my shoulder, breaking the ice was nice, she was getting more and more comfortable with me. 

“They have trained you well,” 

“We shall see,” I said, taking and kissing the back of her hand. She stopped and watched me, her mouth slightly opened. 

I topped off her drink as the waiter brought our food and held up my glass for a toast. “To new beginnings,” I smiled. 

“Yes, to new beginnings,” Olivia clinked her glass with mine. 

“And living out our wildest dreams,” I added.