Start Me Up

Olivia

Tony made me instantly comfortable, by attention to detail and engaging in an interesting conversation as we enjoyed our meal. I was amazed at how comfortable and in control he was. The more we talked, the more I relaxed and I began looking at him in a different light, not as Sharon’s son, but as my date. 

“What’s on your mind?” he asked, tilting his towards me to see my eyes. His hazel eyes danced with mine as I tried to find the correct words to respond.

“I was thinking you were correct when you said our connection would be better since we already know each other,” I said. “I don’t think I would feel this comfortable with anyone else.”

“Well I’m glad I can do that for you,” he smiled while caressing my back slowly with his hand. “And there is more to come,” 

My mind went wild about the things Tony would do to my body. I wanted him to take his time giving me a moment to remember. “I’m looking forward to it,” I replied and took a sip of my drink. 

The food was amazing and the cocktails were delicious. I didn’t want to return home as I didn’t want the day to end as it was still early and I wanted to spend more time with Tony. I think he felt the same way as he suggested we take a boat tour of Chicago after we visited a few museums. I felt like I was on a real date, holding his hand walking together through Millenium Park, taking pictures at the ‘Bean’ and then again at Buckingham Fountain. We sat down along the lakefront while waiting for our reservation for the Fireboat. 

“Tony this is amazing,”   I watched the waves lap against the shore while the warm summer wind blew softly around us.

“I’m glad you’re enjoying yourself,” he looked at me, tipping my chin up to see my eyes.

I blushed a bit as he gazed into my eyes. “You make me feel things when you look at me like that,” I admitted. 

“Good things I hope,” he caressed my face, his eyes never leaving mine. I was sinking deeper and deeper and I didn’t want it to stop.

“Yes,” I turned towards him, leaning in a bit to whisper. “Good and naughty things,” I replied. 

Tony smiled, “I like those types of feelings,” he leaned in slowly and softly covered my mouth with his, kissing me gently. His lips were soft, warm and full as I pulled him closer to me, kissing him deeply. 

He inhaled quickly and held my face in his hands while his tongue darted in and out my mouth. He parted slowly, planting small kisses upon my lips, stirring up my desires deep within by his luscious kisses. I didn’t want to stop. Tony was a great kisser, so much better than Robert. Kissing Tony made me want to feel more of him. I allowed my mind to wander as Tony kissed me along my neckline while holding me in his arms. 

“You’re a good kisser,” I whispered, leaning my head against his shoulder. 

“So are you,” Tony kissed the top of my head while wrapping his arms around me. 

“Do you mind if we fulfill our contract tonight?”

“I don’t mind at all. Are you sure?”

“I am. Your kisses make me want more,” I admitted shyly.  He smiled and kissed my forehead, pulling me closer to him as the breeze blew over us. 

“I’ve been wanting you since I laid eyes on you,” he whispered close to my ear. “And I have so much more to give you,”

“I’m looking forward to it,” 

Tony and I enjoyed our time at the lakefront for a few hours, grabbing a snack or two before we boarded the Fireboat for our tour of the city and fireworks. The tour was amazing as well as the fireworks, however we didn’t see much of them due to us being lip-locked for a good portion of the display. I was obsessed with kissing him, each time he made me want more and more. The idea of Tony fulfilling my sexual fantasies excited me as the night went on. 

“Before we go back to my place, I would like to take you to one more place,” 

“I’m up for anything,”

“Good. We can get a drink to finish off the night along with a rooftop movie,”

“A rooftop movie? For someone who just threw this day together, you surely have thought this through,”

“Yes, I did. I had planned to do these things with you for our date, but I figured we didn’t have to wait since we were meeting up today,”

“Good call,”

“Thanks. I wanted this to be as organic and welcoming as possible,” he said pointing between the both of us. “I wanted us to have a connection that wasn’t forced or awkward,”

“You accomplished it well, this was totally organic,”  Tony smiled as he held my hand while reaching the rooftop for a movie and drinks in the West Loop. “You’re spoiling me,”

“You deserve to be spoiled. And I plan to spoil you each and every time we are together,” 

I was impressed. Tony was not the young man that I saw grow up in front of my eyes. He had become a well groomed man who immersed himself into having the necessary knowledge and skills to reach his goals by fulfilling his needs and desires. When we grabbed our drinks and walked over to our reserved loveseat, I realized that we have been drinking off and on throughout the day; I really needed this outing. I must admit, Sharon was right. 

“Enjoying yourself?” Tony asked as I removed my sandals, bringing my legs up onto the cushions. Tony placed his arm around me and I cuddled up next to him, I was happy.

“I am,” I looked at Tony, my eyes darting back and forth with him. “Thank you,” 

“Most welcome. Anytime.” Tony moved a few strands of hair from my forehead back behind my ears. He softly touched my cheek, caressing it with the back of his fingers. “Don’t worry, beautiful. It’s not over yet,” 

I smiled to the point in which I blushed, I buried my head into his chest covering my mouth. How is this happening? Tony chuckled and raked his fingers through my hair. I raised my head and looked at him. He gazed back at me, smiling softly.

“So, what made you want to work for the service?”

“Other than the experience and knowledge along with the skills that I have learned, it opens up a network to which I wouldn’t be able to reach had I not applied,”

“I see. Does Sharon know about you working for the service?”

“No, neither does Matt. They just think I picked up a government job,” he chuckled. “But it will help Matt and I get the capital for our online sporting goods business,”

“From what I paid, I’m sure you’ll be able to reach your goal with more contracts,”  The price of the contract wasn’t much but if he had enough of them, it would help him a lot. 

“You may be right, but I haven’t proven I’m worth it to you yet,” Tony ran his fingers up and down my arm softly, his nails gently raking my skin sending chills with every touch.

“You are well on your way Mister,” I smiled leaning forward and planting a kiss on his lips. Tony cupped the back of my head pressing his lips against mine, kissing softly. “Mmmm, each time you kiss me,” I moaned between us. “You make me want you more,”

Tony chuckled softly, his warm breath spread across my lips, “I want you to get to the point you want to ravage me,” he tapped me on my nose and pulled me closer. 

The movie started and Tony had a plan. He was determined to have me reach my boiling point out in public, luckily we were outside, at night and everyone was facing in one particular direction. He asked me to swing my legs around and across his lap, to hold me close in his arms. We laid our snacks of pretzels, assorted nuts and candy on my lap for easy access, using it as a distraction as Tony slipped his hand under my dress and between my legs. 

I froze at first, my heart beating faster than ever, fearsome we would be caught. Tony was calm and flirtatious, drawing my attention away from those around us to just him. He gazed into my eyes as he slowly spread my legs reaching my mound. I instantly felt his finger slide up and down against my nectar soaked panties. His finger slid up my crease, touching my bean at the top. 

My dress was loose enough for no one to notice his hand  between my legs unless they watched us closely. Feeling his fingertips circling my bean made me bite my lip as he was not playing fair. He didn’t take his eyes off of me as felt him pull my panties to the side and slip a finger in my cavern.

“Ahhh,” I moaned and he quickly covered my mouth with his tongue invading all around as he fucked me slow and deep with his finger.

“You’re so wet,” he mumbled between kisses. 

“Ahhh….ahhh,” I moaned softly, pressing my forehead against his. Tony slipped in another finger inside my luscious pit.

“You are so fucking wet,”  he kissed my neck  while I crossed my legs locking his hand between them. “I want you to cum in my hand,” 

My nipples instantly hardened as he moved his fingers deep inside me while rubbing my clit with the palm of his hand. “Fuck…Tony,” I mewed softly trying to avoid drawing attention to us. 

“Yes, c’mon Olivia,” he whispered slowly, pulling his slick covered fingers from my snatch and rubbing my clit vigorously. 

“Tony,” I panted. “I can’t..aaahhh…” I was going to explode which would blow our cover, even though it was feeling wonderful, I had to beg him to stop. “Please Tony, mmmmm, not here,” I grabbed his hand, hoping he would stop. 

“Ok,” he smiled, removing his hand from between my legs. I watched as he took his finger directly to his mouth, sucking my juices, lapping every drop. My mouth hung open. “Sweet,” 

“I can see you are definitely going to be worth my while,” I cupped his face. 

“I aim to please Olivia. And I want to please you,” 

“You can please me as much as you want,” I admitted. “Let’s go,”

“No problem,” Tony pulled and straightened my dress while I placed the snacks on the floor in front of the loveseat. I quickly swung my legs around and stood up. Tony grabbed my hand and we were off in the middle of the movie. 

Tony called a driver to pick us up, taking us to his condo. I was amazed that Tony worked under Elegant Industries, they knew who to pick as employees. Located next to the office building is a luxury hotel which we entered by  a side door. Tony scanned his key card at the elevator and we rode up to his floor. He held me close, kissing me deeply as we arrived at his floor. 

Ironically the level resembled a hotel floor, all of the rooms featured the same style door with a suite number. We entered Suite 1275. Tony opened the door, turned on the lights and held the door open for me to enter. It looked like a normal hotel room yet a very expensive one.

“You live here?” I asked, looking around.

“Not exactly,” he closed and locked the door behind him. “This floor in the building is designated for contracts only,”

“Oh, do you live in this building?”

“Yes, two floors up,” he smiled. “Why do you ask? You wanna come and see me?” Tony chuckled, walking over to me with his arms open to embrace me.

I walked into his arms, feeling his member sticking against my stomach. “Do they have long term contracts?” I smiled. Tony grinned at the thought.

“I’m sure we could make some arrangements,” he pressed his lips against mine, inhaling at the same time. “Olivia, can I have you now?” 

“Yes, take me Tony,” I surrendered to his will.  He kissed me hard, his tongue making love to my mouth as he picked me up and carried me to the bedroom. 

He dropped me on the bed, raised my dress and snatched off my panties. “I’ve been waiting to taste you all night,” Tony said just before burying his face in my mound.

“Aaaaaaaahhhhhhhh!” I moaned loudly as he grabbed my ankles and spread them apart. 

Tony’s tongue lapped my slickness as he munched on my cunt. He spread my thighs as wide as they could go using his fingers to spread my satin lips open as his tongue quickly flicked my bean over and over, sucking it between his lips and humming. 

“MMmmmmm, Olivia..,” he hummed. “I want you to cum in my mouth,” 

“Aaaaah….aaaah….aaaah….aaah..” I moaned. I wasn’t going to have a choice in the matter, holding his head between my legs raising my ass to grind my snatch directly in his mouth. 

“Mmmmmm, so wet…mmmmm Olivia…..” he sucked my river of juices while I held his head steady. 

“Fuck!...ahh…ahhh..ahhh…ooooooo, yes,” I heard him slurp my nectar like a bear licking honey.

I wiggled my dress up above my head and threw it over to the side. I released my breasts and pinched my nipples while Tony continued pleasing me orally.  He kissed my inner thighs while running his hands all over my body, my garden quivered wanting more satisfaction. Tony slowly stood leaving me naked and spread out waiting for him while he undressed. 

His body was phenomenal. Ripped in all the right places, young and tender and I’m sure he had the stamina of 100 horses. He pulled out a box of condoms and placed them on the side of the table, grabbing one and rolling it on his shaft. He walked over to the bed watching me like a hawk. Tony crawled slowly on top of me, my legs open exposing my honey pot waiting for him to enter. He laid on top of me, caressing my face and kissing me all over. He lowered his head, licking circles around my nipple. 

“Mmmmmm,” I moaned softly anxiously waiting to feel him fill me up. 

“Olivia,”

“Yes, Tony?”

“Let me know if I get a little rough,” he touched my lips and kissed me softly. “I’ve been dreaming about fucking you for a long time,”

“Oh my,” I wanted to fuck him too. Robert never said anything like that to me. “Well fuck me, Tony. Fuck me good,” 

“Don’t worry, I will.”  Tony quickly slid his meaty cock deep inside my snatch, making my back arch. 

“AAAAAAHHHHhhhh!” I moaned loudly. Ecstasy filled my entire crevice as his dick spread my walls in a fashion that made me cream instantly. 

“I most definitely will.”