Yes, No, Maybe

Olivia

Tony 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 Tony’s chest. He was still sleeping, me wrapped in his arms, our naked bodies giving each other warm as the fire had died down to a smoldering ball of warmth just barely keeping our feet warm. 

We had fallen asleep after we fucked each others brains out by the fire under the stars. It was a new experience and it was absolutely exhilarating. I became so uninhibited with Tony and I enjoyed it.  I snuggled under the blanket, pulling it tighter around my neck and Tony moved as I wrapped my foot around his ankle.

“Mmmm, good morning.” He whispered, his morning voice growled in his chest and rattled in my ear.  I smiled, circling his nipple with the tip of my finger. He chuckled softly, grabbing my hand and kissed the top of my head, holding me tighter and closer to him. 

“Morning,” I adjusted, laying more on his side while his hand slid down and cupped my ass cheek. “We fell asleep out here.”  I whispered hearing the birds chirping, awakening the day. 

“Mmmm, yes we did. Beautiful way to wake up, don’t you think?”

“It is very nice waking up, naked and with you.” 

“Yes Ma’am.” Tony chuckled. “It looks like our chef has come here to prepare breakfast.”

“Someone’s here?” I nervously looked around and saw two people preparing food in the kitchen. “Are you serious?”

Tony laughed and held me close. “It’s okay, I’ll cover you so you can get dressed. I’ll make sure those goodies aren’t seen.” 

“Ok, I’ll tell you when I’m ready.” We adjusted ourselves on the chair and enjoyed the morning breeze from off the lake. 

“How are you feeling this morning?” Tony’s voice sounded so sexy and raspy as he spoke softly with his lips pressed gently against my forehead.

“I feel refreshed. This has been an amazing trip so far.” I enjoyed being with Tony and I knew he enjoyed being with me, but could we do this on a regular thing?  The thought quickly raced through my mind. 

“Good to know. You have remarkable stamina. Not many women can go as long as you do.” He touched my cheek softly with his finger tips, tracing my cheekbones down to my chin. 

I smiled because I was proud that I could hang with the best of them. I may not be the same age but I could fuck just like them, if not better. “Well you make me wanna go longer, I’ve become addicted.” I confessed. 

“You’re addicting as well. I love the way you feel, it’s magical.” Tony admitted. I snuggled closer to him, wrapping my arm around his waist, holding him tightly. 

“You make it so natural and comfortable to be with you. I didn’t expect this at all.”

“I know you didn’t expect me, but you also didn’t expect to connect with someone who may be younger than you?” He added. 

“Yeah.” I didn’t. I figured someone about a few years younger, not an entire generation. 

“Why? You’re a beautiful woman. Did you think a younger guy wouldn’t be attracted to you?”

“That too, but I didn’t think I would have anything in common or anything to talk about.”

“Why, because we’re younger?”

“Yes.” 

“Understandable, not all of us have our shit together.” Tony readjusted to face me. “But some of us have this shit planned out. Giving us the opportunity to meet wonderful women like yourself.” He tipped my chin up and kissed my lips ever so gently. 

I was falling and falling hard. I wasn’t even divorced yet and I started having feelings for Tony. My best friend’s son. I couldn’t do this to him or her and I needed to keep them in check. But I wanted more of Tony, as much as I could get.  He had awakened the kraken and she did not want to go back to slumber. 

“I like those kinds of plans,” I smirked while he grinned. He was flattered. I had no problem giving him his props because he definitely deserved it. “You said they do have long term contracts correct?”

“Are you trying to keep me all to yourself, Olivia?” Tony nuzzled me with his nose.

“For now.” I smiled. He kissed me softly and took me in. I was floating on clouds until we were interrupted by the chef. “Would you mind?” 

“Ehem, Sir,” A stoutly man interrupted us as he  stood with his hands clasped together in front of his crisp white apron. “Breakfast is ready along with some brunch items as requested. I will return for lunch. Would you like for me to bring the items out here?”

“Uh, no. No, that’s okay. You can leave everything in the kitchen.” Tony was so in control, he didn’t flinch at all. I was so confident, he amazed me. 

“As you wish, we will be leaving now, Sir. See you at lunch.” The chef nodded and returned to the kitchen. 

Tony and I watched the two of them pack up their things and leave the house. We heard in the distance, a car driving away and we were once again, all alone. 

“We can get up now, I think the coast is clear.” Tony slowly uncovered us and the cool air danced across my skin leaving goosebumps in return.

I stood up naked and shivering as Tony stood up wrapping his arms around me, his member hanging between us touching my stomach. I looked up at him, he smirked as his eyes danced with mine. I knew my hair was a mess, but I felt beautiful by the way Tony  gazed at me. I didn’t feel like I was being judged at all, he made me feel like he was connecting with me mentally and physically in a very honest manner. 

I wanted full access to him whenever I wanted and I was willing to pay the price if needed. He was something I’d been needing for the past 25 years and I wasn’t ready to give it up.

Tony

I could tell Olivia was finally relaxing and having a great time. It looked as if she finally was able to let her hair down and have fun for a change and enjoy herself. I felt she finally let go of whatever anxiety was holding her back from submitting herself fully to me. She did last night, she fucked me with such passion, she made me feel something last night that I had never felt with anyone before. So much so, it scared me. I couldn’t explain what it was, but something changed between us last night, we grew closer. We connected.

“I’ll wrap the blanket around you and you run for the door. I’ll grab the clothes.” I stepped out of the blanket, my dick swinging and quickly wrapped it around her. 

“Oh Tony, you’re gonna be cold!” She said. 

“Go open the door, quick!” I grabbed the clothes, holding them close to me for warmth. 

Olivia sprinted across the patio and held the door open for me as I ran barefoot across the ground and into the house. She laughed as I immediately dropped all of the clothes and stood butt ass naked in front of her with my arms open to welcome her to me. 

“The food smells delicious.” I looked at the nice layout the chef left for us. 

“It’s wonderful. Let’s eat then shower after.” She slipped on her pjs from last night and I grabbed my pants. 

“Sounds like a plan to me.” 

The breakfast was delicately made for two with a selection of fruit and breakfast pastries, as well as a carafe of Mimosas.   Olivia and I filled out plates at the edge and took a seat together on the couch.  I flicked on the television to have background noise as we enjoyed breakfast and each other. 

“I could get used to this.” Olivia blurted, taking a bite of her pastry. 

“Waking up next to a handsome stud like myself?” I joked. She playfully hit my arm. 

“That too, but waking up with a view like that and food ready when I get out of bed.”  

“I completely understand. That’s my goal.” I stabbed a few bits of scrambled egg with my fork and stuffed it in my mouth. 

“So you don’t want to do this forever?” I knew the subject would come up again. She was testing the waters. I knew she wanted me. I felt last night there was a moment that felt so good, she fell for me. 

“I want to start my business and have a place of my own,” I folded my legs on the couch and faced her, placing my plate on a pillow sitting on my lap. “That way I could sit on the patio naked if I wanted to.” I chuckled at the thought of us waking up outside. 

“I feel you. That would be nice to have everyday.”

“Well you have plenty of money, why don’t you buy a house like this?” I stretched out my hands and looked around. 

“Richard has a lot of money, I will only get a portion from the divorce.” She said looking down at her plate. I didn’t expect her to mention her husband, we hadn’t discussed him choosing to live this fairytale leaving a  little bit of reality out of it. 

“Is that what you’re planning to do? Get a divorce?” I asked, I was curious. I didn’t know she had thought the entire process of what she wanted to do.  

“Eventually. I think you’ve helped me realize that my marriage is over.” 

“Really?” I stopped eating and looked at her. She grinned, covering her mouth while she chewed the rest of her food. “I didn’t mean to be the reason.”

“You’re not. You were the satisfaction that I needed for a long time.”

“Well I aim to please.” I winked at her, making her blush and turn away. The way she looked at me was dangerous. She made me smile and my dick moved. 

“You sure as fuck do,” Olivia gazed at me, making butterflies grow in my stomach. “And you do it well.”

“Glad you approve.” I grinned. She made me blush, I felt my cheeks grow warm the longer she gazed at me. 

“Do you know how long you plan on working with the service?”

“Not really. I just started so it depends on how long it would take me to reach all of the goals I have set for myself.”

“I see.” I had a feeling that wasn’t the answer she wanted to hear. 

“Don’t worry, I’m sure I’ll be available for you, regardless if you have a contract or not.” I suggested. I gave her an option that allowed her to still have sex with me for free instead of her having to pay for it. 

“I don’t want you to stop on my behalf, I’ll pay for a contract.” Olivia took a gulp of her mimosa to wash down her food. 

“Oh I wasn’t going to stop working, I just didn’t want to take your money anymore.” I admitted. 

“My money isn’t good enough?” 

I tilted my head and smiled at her. “You’re money is damn good, I just feel bad fucking your brains out and taking your money.” I chuckled.   She covered her mouth as she blushed. 

“Oh my,” she took another sip of her drink. “Well, will you accept a long term contract?”  She wanted me for herself. 

I was flattered because I wanted to be with her as well, she’s a remarkable woman but I didn’t want to feel like I’m just her boy toy whom she pays to get laid. I want to be able to obtain skills that will help me with my business and currently I’m in a sweet spot to do so. 

“I don’t know to be honest. It depends on how long and who’s the person.” I was being honest. I knew it left her wanting a more detailed answer, but I didn’t want to get her hopes up. “I don’t want to be someone’s boy toy or somewhere on that level.”

“Oh, well that’s understandable. At least you have the option to decline.”  Olivia uttered with a little disappointment. 

“Yes, that is an option.” I watched her and saw her light dim a little. She looked concerned.

I wanted to say that her response was due to her being tired but that was definitely not the case, we just woke up. I think she reacted that way because she may have initiated her feelings for me, however I could be wrong. I just noticed her mood would slightly change when we talked about me working for the service and her questions surrounding the long term contracts. 

“But don’t worry, no one is going to snatch me up that quick.”

“What do you mean?” Olivia placed her empty plate on the table in front of us and finished off her drink.

“Long contracts and/or Intimate contracts don’t come a lot. They do come, but not as much as you would think.”

“I see.”

“And besides I’m still new, I just got placed in the pool of escorts therefore those who are looking for any type of contract, I would be at the end of the list.” I mentioned hoping she could understand the odds. 

“But you could still get a contract, correct?” Olivia asked.

“Correct.” I admitted. She showed she was  a little disappointed that I was still available to receive a contract but she shook it off quickly. 

“Ready to take that shower?” Olivia stood up and held out her hand. I placed my plate on the table, stood up and held her hand. 

“Lead the way.”